diff --git a/.devcontainer/Dockerfile b/.devcontainer/Dockerfile
index a823829419..4e7a8d7618 100644
--- a/.devcontainer/Dockerfile
+++ b/.devcontainer/Dockerfile
@@ -1,9 +1,8 @@
 FROM mcr.microsoft.com/vscode/devcontainers/rust:1-bullseye
 
-# Install cmake and protobuf-compiler
+# Install cmake
 RUN apt-get update \
   && apt-get install -y cmake \
-  && apt-get install -y protobuf-compiler \
   && rm -rf /var/lib/apt/lists/*
 
 # Install Deno
diff --git a/.dprint.json b/.dprint.json
index 6ee3db3c5d..3b2376f786 100644
--- a/.dprint.json
+++ b/.dprint.json
@@ -65,13 +65,17 @@
     "tests/wpt/runner/expectation.json",
     "tests/wpt/runner/manifest.json",
     "tests/wpt/suite",
-    "third_party"
+    "third_party",
+    "tests/specs/run/shebang_with_json_imports_tsc",
+    "tests/specs/run/shebang_with_json_imports_swc",
+    "tests/specs/run/ext_flag_takes_precedence_over_extension",
+    "tests/specs/run/error_syntax_empty_trailing_line/error_syntax_empty_trailing_line.mjs"
   ],
   "plugins": [
-    "https://plugins.dprint.dev/typescript-0.93.0.wasm",
-    "https://plugins.dprint.dev/json-0.19.3.wasm",
+    "https://plugins.dprint.dev/typescript-0.93.2.wasm",
+    "https://plugins.dprint.dev/json-0.19.4.wasm",
     "https://plugins.dprint.dev/markdown-0.17.8.wasm",
-    "https://plugins.dprint.dev/toml-0.6.2.wasm",
+    "https://plugins.dprint.dev/toml-0.6.3.wasm",
     "https://plugins.dprint.dev/exec-0.5.0.json@8d9972eee71fa1590e04873540421f3eda7674d0f1aae3d7c788615e7b7413d0",
     "https://plugins.dprint.dev/g-plane/pretty_yaml-v0.5.0.wasm"
   ]
diff --git a/.github/workflows/cargo_publish.yml b/.github/workflows/cargo_publish.yml
index 45f075b579..3af97f4662 100644
--- a/.github/workflows/cargo_publish.yml
+++ b/.github/workflows/cargo_publish.yml
@@ -2,10 +2,15 @@ name: cargo_publish
 
 on: workflow_dispatch
 
+# Ensures only one publish is running at a time
+concurrency:
+  group: ${{ github.workflow }}
+  cancel-in-progress: true
+
 jobs:
   build:
     name: cargo publish
-    runs-on: ubuntu-20.04-xl
+    runs-on: ubuntu-24.04-xl
     timeout-minutes: 90
 
     env:
@@ -28,16 +33,10 @@ jobs:
       - uses: dsherret/rust-toolchain-file@v1
 
       - name: Install deno
-        uses: denoland/setup-deno@v1
+        uses: denoland/setup-deno@v2
         with:
           deno-version: v1.x
 
-      - name: Install protoc
-        uses: arduino/setup-protoc@v3
-        with:
-          version: '21.12'
-          repo-token: '${{ secrets.GITHUB_TOKEN }}'
-
       - name: Publish
         env:
           CARGO_REGISTRY_TOKEN: ${{ secrets.CARGO_REGISTRY_TOKEN }}
diff --git a/.github/workflows/ci.generate.ts b/.github/workflows/ci.generate.ts
index e9fcacc823..5ed02d3cde 100755
--- a/.github/workflows/ci.generate.ts
+++ b/.github/workflows/ci.generate.ts
@@ -5,16 +5,16 @@ import { stringify } from "jsr:@std/yaml@^0.221/stringify";
 // Bump this number when you want to purge the cache.
 // Note: the tools/release/01_bump_crate_versions.ts script will update this version
 // automatically via regex, so ensure that this line maintains this format.
-const cacheVersion = 15;
+const cacheVersion = 25;
 
-const ubuntuX86Runner = "ubuntu-22.04";
-const ubuntuX86XlRunner = "ubuntu-22.04-xl";
+const ubuntuX86Runner = "ubuntu-24.04";
+const ubuntuX86XlRunner = "ubuntu-24.04-xl";
 const ubuntuARMRunner = "ubicloud-standard-16-arm";
 const windowsX86Runner = "windows-2022";
 const windowsX86XlRunner = "windows-2022-xl";
 const macosX86Runner = "macos-13";
 const macosArmRunner = "macos-14";
-const macosArmXlRunner = "macos-14-xlarge";
+const selfHostedMacosArmRunner = "self-hosted";
 
 const Runners = {
   linuxX86: {
@@ -39,15 +39,10 @@ const Runners = {
     runner: macosX86Runner,
   },
   macosArm: {
-    os: "macos",
-    arch: "aarch64",
-    runner: macosArmRunner,
-  },
-  macosArmXl: {
     os: "macos",
     arch: "aarch64",
     runner:
-      `\${{ github.repository == 'denoland/deno' && '${macosArmXlRunner}' || '${macosArmRunner}' }}`,
+      `\${{ github.repository == 'denoland/deno' && startsWith(github.ref, 'refs/tags/') && '${selfHostedMacosArmRunner}' || '${macosArmRunner}' }}`,
   },
   windowsX86: {
     os: "windows",
@@ -66,7 +61,7 @@ const prCacheKeyPrefix =
   `${cacheVersion}-cargo-target-\${{ matrix.os }}-\${{ matrix.arch }}-\${{ matrix.profile }}-\${{ matrix.job }}-`;
 
 // Note that you may need to add more version to the `apt-get remove` line below if you change this
-const llvmVersion = 18;
+const llvmVersion = 19;
 const installPkgsCommand =
   `sudo apt-get install --no-install-recommends clang-${llvmVersion} lld-${llvmVersion} clang-tools-${llvmVersion} clang-format-${llvmVersion} clang-tidy-${llvmVersion}`;
 const sysRootStep = {
@@ -78,7 +73,7 @@ export DEBIAN_FRONTEND=noninteractive
 sudo apt-get -qq remove --purge -y man-db  > /dev/null 2> /dev/null
 # Remove older clang before we install
 sudo apt-get -qq remove \
-  'clang-12*' 'clang-13*' 'clang-14*' 'clang-15*' 'clang-16*' 'llvm-12*' 'llvm-13*' 'llvm-14*' 'llvm-15*' 'llvm-16*' 'lld-12*' 'lld-13*' 'lld-14*' 'lld-15*' 'lld-16*' > /dev/null 2> /dev/null
+  'clang-12*' 'clang-13*' 'clang-14*' 'clang-15*' 'clang-16*' 'clang-17*' 'clang-18*' 'llvm-12*' 'llvm-13*' 'llvm-14*' 'llvm-15*' 'llvm-16*' 'lld-12*' 'lld-13*' 'lld-14*' 'lld-15*' 'lld-16*' 'lld-17*' 'lld-18*' > /dev/null 2> /dev/null
 
 # Install clang-XXX, lld-XXX, and debootstrap.
 echo "deb http://apt.llvm.org/jammy/ llvm-toolchain-jammy-${llvmVersion} main" |
@@ -93,7 +88,7 @@ ${installPkgsCommand} || echo 'Failed. Trying again.' && sudo apt-get clean && s
 (yes '' | sudo update-alternatives --force --all) > /dev/null 2> /dev/null || true
 
 echo "Decompressing sysroot..."
-wget -q https://github.com/denoland/deno_sysroot_build/releases/download/sysroot-20240528/sysroot-\`uname -m\`.tar.xz -O /tmp/sysroot.tar.xz
+wget -q https://github.com/denoland/deno_sysroot_build/releases/download/sysroot-20241030/sysroot-\`uname -m\`.tar.xz -O /tmp/sysroot.tar.xz
 cd /
 xzcat /tmp/sysroot.tar.xz | sudo tar -x
 sudo mount --rbind /dev /sysroot/dev
@@ -198,14 +193,9 @@ const installNodeStep = {
   uses: "actions/setup-node@v4",
   with: { "node-version": 18 },
 };
-const installProtocStep = {
-  name: "Install protoc",
-  uses: "arduino/setup-protoc@v3",
-  with: { "version": "21.12", "repo-token": "${{ secrets.GITHUB_TOKEN }}" },
-};
 const installDenoStep = {
   name: "Install Deno",
-  uses: "denoland/setup-deno@v1",
+  uses: "denoland/setup-deno@v2",
   with: { "deno-version": "v1.x" },
 };
 
@@ -385,7 +375,7 @@ const ci = {
             job: "test",
             profile: "debug",
           }, {
-            ...Runners.macosArmXl,
+            ...Runners.macosArm,
             job: "test",
             profile: "release",
             skip_pr: true,
@@ -501,7 +491,6 @@ const ci = {
           if: "matrix.job == 'bench' || matrix.job == 'test'",
           ...installNodeStep,
         },
-        installProtocStep,
         {
           if: [
             "matrix.profile == 'release' &&",
@@ -765,8 +754,10 @@ const ci = {
           run: [
             "cd target/release",
             "zip -r deno-${{ matrix.arch }}-unknown-linux-gnu.zip deno",
+            "shasum -a 256 deno-${{ matrix.arch }}-unknown-linux-gnu.zip > deno-${{ matrix.arch }}-unknown-linux-gnu.zip.sha256sum",
             "strip denort",
             "zip -r denort-${{ matrix.arch }}-unknown-linux-gnu.zip denort",
+            "shasum -a 256 denort-${{ matrix.arch }}-unknown-linux-gnu.zip > denort-${{ matrix.arch }}-unknown-linux-gnu.zip.sha256sum",
             "./deno types > lib.deno.d.ts",
           ].join("\n"),
         },
@@ -791,8 +782,10 @@ const ci = {
             "--entitlements-xml-file=cli/entitlements.plist",
             "cd target/release",
             "zip -r deno-${{ matrix.arch }}-apple-darwin.zip deno",
+            "shasum -a 256 deno-${{ matrix.arch }}-apple-darwin.zip > deno-${{ matrix.arch }}-apple-darwin.zip.sha256sum",
             "strip denort",
             "zip -r denort-${{ matrix.arch }}-apple-darwin.zip denort",
+            "shasum -a 256 denort-${{ matrix.arch }}-apple-darwin.zip > denort-${{ matrix.arch }}-apple-darwin.zip.sha256sum",
           ]
             .join("\n"),
         },
@@ -807,7 +800,9 @@ const ci = {
           shell: "pwsh",
           run: [
             "Compress-Archive -CompressionLevel Optimal -Force -Path target/release/deno.exe -DestinationPath target/release/deno-${{ matrix.arch }}-pc-windows-msvc.zip",
+            "Get-FileHash target/release/deno-${{ matrix.arch }}-pc-windows-msvc.zip -Algorithm SHA256 | Format-List > target/release/deno-${{ matrix.arch }}-pc-windows-msvc.zip.sha256sum",
             "Compress-Archive -CompressionLevel Optimal -Force -Path target/release/denort.exe -DestinationPath target/release/denort-${{ matrix.arch }}-pc-windows-msvc.zip",
+            "Get-FileHash target/release/denort-${{ matrix.arch }}-pc-windows-msvc.zip -Algorithm SHA256 | Format-List > target/release/denort-${{ matrix.arch }}-pc-windows-msvc.zip.sha256sum",
           ].join("\n"),
         },
         {
@@ -820,6 +815,7 @@ const ci = {
           ].join("\n"),
           run: [
             'gsutil -h "Cache-Control: public, max-age=3600" cp ./target/release/*.zip gs://dl.deno.land/canary/$(git rev-parse HEAD)/',
+            'gsutil -h "Cache-Control: public, max-age=3600" cp ./target/release/*.sha256sum gs://dl.deno.land/canary/$(git rev-parse HEAD)/',
             "echo ${{ github.sha }} > canary-latest.txt",
             'gsutil -h "Cache-Control: no-cache" cp canary-latest.txt gs://dl.deno.land/canary-$(rustc -vV | sed -n "s|host: ||p")-latest.txt',
           ].join("\n"),
@@ -1001,8 +997,10 @@ const ci = {
             "github.repository == 'denoland/deno' &&",
             "startsWith(github.ref, 'refs/tags/')",
           ].join("\n"),
-          run:
+          run: [
             'gsutil -h "Cache-Control: public, max-age=3600" cp ./target/release/*.zip gs://dl.deno.land/release/${GITHUB_REF#refs/*/}/',
+            'gsutil -h "Cache-Control: public, max-age=3600" cp ./target/release/*.sha256sum gs://dl.deno.land/release/${GITHUB_REF#refs/*/}/',
+          ].join("\n"),
         },
         {
           name: "Upload release to dl.deno.land (windows)",
@@ -1016,8 +1014,10 @@ const ci = {
           env: {
             CLOUDSDK_PYTHON: "${{env.pythonLocation}}\\python.exe",
           },
-          run:
+          run: [
             'gsutil -h "Cache-Control: public, max-age=3600" cp ./target/release/*.zip gs://dl.deno.land/release/${GITHUB_REF#refs/*/}/',
+            'gsutil -h "Cache-Control: public, max-age=3600" cp ./target/release/*.sha256sum gs://dl.deno.land/release/${GITHUB_REF#refs/*/}/',
+          ].join("\n"),
         },
         {
           name: "Create release notes",
@@ -1047,15 +1047,25 @@ const ci = {
           with: {
             files: [
               "target/release/deno-x86_64-pc-windows-msvc.zip",
+              "target/release/deno-x86_64-pc-windows-msvc.zip.sha256sum",
               "target/release/denort-x86_64-pc-windows-msvc.zip",
+              "target/release/denort-x86_64-pc-windows-msvc.zip.sha256sum",
               "target/release/deno-x86_64-unknown-linux-gnu.zip",
+              "target/release/deno-x86_64-unknown-linux-gnu.zip.sha256sum",
               "target/release/denort-x86_64-unknown-linux-gnu.zip",
+              "target/release/denort-x86_64-unknown-linux-gnu.zip.sha256sum",
               "target/release/deno-x86_64-apple-darwin.zip",
+              "target/release/deno-x86_64-apple-darwin.zip.sha256sum",
               "target/release/denort-x86_64-apple-darwin.zip",
+              "target/release/denort-x86_64-apple-darwin.zip.sha256sum",
               "target/release/deno-aarch64-unknown-linux-gnu.zip",
+              "target/release/deno-aarch64-unknown-linux-gnu.zip.sha256sum",
               "target/release/denort-aarch64-unknown-linux-gnu.zip",
+              "target/release/denort-aarch64-unknown-linux-gnu.zip.sha256sum",
               "target/release/deno-aarch64-apple-darwin.zip",
+              "target/release/deno-aarch64-apple-darwin.zip.sha256sum",
               "target/release/denort-aarch64-apple-darwin.zip",
+              "target/release/denort-aarch64-apple-darwin.zip.sha256sum",
               "target/release/deno_src.tar.gz",
               "target/release/lib.deno.d.ts",
             ].join("\n"),
@@ -1074,6 +1084,7 @@ const ci = {
               "./target",
               "!./target/*/gn_out",
               "!./target/*/*.zip",
+              "!./target/*/*.sha256sum",
               "!./target/*/*.tar.gz",
             ].join("\n"),
             key: prCacheKeyPrefix + "${{ github.sha }}",
diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 035a4244fc..39a3afe769 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -62,18 +62,18 @@ jobs:
             profile: debug
           - os: macos
             arch: x86_64
-            runner: '${{ (!contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'')) && ''ubuntu-22.04'' || ''macos-13'' }}'
+            runner: '${{ (!contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'')) && ''ubuntu-24.04'' || ''macos-13'' }}'
             job: test
             profile: release
             skip: '${{ !contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'') }}'
           - os: macos
             arch: aarch64
-            runner: macos-14
+            runner: '${{ github.repository == ''denoland/deno'' && startsWith(github.ref, ''refs/tags/'') && ''self-hosted'' || ''macos-14'' }}'
             job: test
             profile: debug
           - os: macos
             arch: aarch64
-            runner: '${{ (!contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'')) && ''ubuntu-22.04'' || github.repository == ''denoland/deno'' && ''macos-14-xlarge'' || ''macos-14'' }}'
+            runner: '${{ (!contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'')) && ''ubuntu-24.04'' || github.repository == ''denoland/deno'' && startsWith(github.ref, ''refs/tags/'') && ''self-hosted'' || ''macos-14'' }}'
             job: test
             profile: release
             skip: '${{ !contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'') }}'
@@ -84,33 +84,33 @@ jobs:
             profile: debug
           - os: windows
             arch: x86_64
-            runner: '${{ (!contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'')) && ''ubuntu-22.04'' || github.repository == ''denoland/deno'' && ''windows-2022-xl'' || ''windows-2022'' }}'
+            runner: '${{ (!contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'')) && ''ubuntu-24.04'' || github.repository == ''denoland/deno'' && ''windows-2022-xl'' || ''windows-2022'' }}'
             job: test
             profile: release
             skip: '${{ !contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'') }}'
           - os: linux
             arch: x86_64
-            runner: '${{ github.repository == ''denoland/deno'' && ''ubuntu-22.04-xl'' || ''ubuntu-22.04'' }}'
+            runner: '${{ github.repository == ''denoland/deno'' && ''ubuntu-24.04-xl'' || ''ubuntu-24.04'' }}'
             job: test
             profile: release
             use_sysroot: true
             wpt: '${{ !startsWith(github.ref, ''refs/tags/'') }}'
           - os: linux
             arch: x86_64
-            runner: '${{ (!contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'' && !contains(github.event.pull_request.labels.*.name, ''ci-bench''))) && ''ubuntu-22.04'' || github.repository == ''denoland/deno'' && ''ubuntu-22.04-xl'' || ''ubuntu-22.04'' }}'
+            runner: '${{ (!contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'' && !contains(github.event.pull_request.labels.*.name, ''ci-bench''))) && ''ubuntu-24.04'' || github.repository == ''denoland/deno'' && ''ubuntu-24.04-xl'' || ''ubuntu-24.04'' }}'
             job: bench
             profile: release
             use_sysroot: true
             skip: '${{ !contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'' && !contains(github.event.pull_request.labels.*.name, ''ci-bench'')) }}'
           - os: linux
             arch: x86_64
-            runner: ubuntu-22.04
+            runner: ubuntu-24.04
             job: test
             profile: debug
             use_sysroot: true
           - os: linux
             arch: x86_64
-            runner: ubuntu-22.04
+            runner: ubuntu-24.04
             job: lint
             profile: debug
           - os: linux
@@ -178,7 +178,7 @@ jobs:
         if: '!(matrix.skip)'
       - if: '!(matrix.skip) && (matrix.job == ''lint'' || matrix.job == ''test'' || matrix.job == ''bench'')'
         name: Install Deno
-        uses: denoland/setup-deno@v1
+        uses: denoland/setup-deno@v2
         with:
           deno-version: v1.x
       - name: Install Python
@@ -199,12 +199,6 @@ jobs:
         uses: actions/setup-node@v4
         with:
           node-version: 18
-      - name: Install protoc
-        uses: arduino/setup-protoc@v3
-        with:
-          version: '21.12'
-          repo-token: '${{ secrets.GITHUB_TOKEN }}'
-        if: '!(matrix.skip)'
       - if: |-
           !(matrix.skip) && (matrix.profile == 'release' &&
           matrix.job == 'test' &&
@@ -258,22 +252,22 @@ jobs:
           # to complete.
           sudo apt-get -qq remove --purge -y man-db  > /dev/null 2> /dev/null
           # Remove older clang before we install
-          sudo apt-get -qq remove   'clang-12*' 'clang-13*' 'clang-14*' 'clang-15*' 'clang-16*' 'llvm-12*' 'llvm-13*' 'llvm-14*' 'llvm-15*' 'llvm-16*' 'lld-12*' 'lld-13*' 'lld-14*' 'lld-15*' 'lld-16*' > /dev/null 2> /dev/null
+          sudo apt-get -qq remove   'clang-12*' 'clang-13*' 'clang-14*' 'clang-15*' 'clang-16*' 'clang-17*' 'clang-18*' 'llvm-12*' 'llvm-13*' 'llvm-14*' 'llvm-15*' 'llvm-16*' 'lld-12*' 'lld-13*' 'lld-14*' 'lld-15*' 'lld-16*' 'lld-17*' 'lld-18*' > /dev/null 2> /dev/null
 
           # Install clang-XXX, lld-XXX, and debootstrap.
-          echo "deb http://apt.llvm.org/jammy/ llvm-toolchain-jammy-18 main" |
-            sudo dd of=/etc/apt/sources.list.d/llvm-toolchain-jammy-18.list
+          echo "deb http://apt.llvm.org/jammy/ llvm-toolchain-jammy-19 main" |
+            sudo dd of=/etc/apt/sources.list.d/llvm-toolchain-jammy-19.list
           curl https://apt.llvm.org/llvm-snapshot.gpg.key |
             gpg --dearmor                                 |
           sudo dd of=/etc/apt/trusted.gpg.d/llvm-snapshot.gpg
           sudo apt-get update
           # this was unreliable sometimes, so try again if it fails
-          sudo apt-get install --no-install-recommends clang-18 lld-18 clang-tools-18 clang-format-18 clang-tidy-18 || echo 'Failed. Trying again.' && sudo apt-get clean && sudo apt-get update && sudo apt-get install --no-install-recommends clang-18 lld-18 clang-tools-18 clang-format-18 clang-tidy-18
+          sudo apt-get install --no-install-recommends clang-19 lld-19 clang-tools-19 clang-format-19 clang-tidy-19 || echo 'Failed. Trying again.' && sudo apt-get clean && sudo apt-get update && sudo apt-get install --no-install-recommends clang-19 lld-19 clang-tools-19 clang-format-19 clang-tidy-19
           # Fix alternatives
           (yes '' | sudo update-alternatives --force --all) > /dev/null 2> /dev/null || true
 
           echo "Decompressing sysroot..."
-          wget -q https://github.com/denoland/deno_sysroot_build/releases/download/sysroot-20240528/sysroot-`uname -m`.tar.xz -O /tmp/sysroot.tar.xz
+          wget -q https://github.com/denoland/deno_sysroot_build/releases/download/sysroot-20241030/sysroot-`uname -m`.tar.xz -O /tmp/sysroot.tar.xz
           cd /
           xzcat /tmp/sysroot.tar.xz | sudo tar -x
           sudo mount --rbind /dev /sysroot/dev
@@ -305,8 +299,8 @@ jobs:
           CARGO_PROFILE_RELEASE_LTO=false
           RUSTFLAGS<<__1
             -C linker-plugin-lto=true
-            -C linker=clang-18
-            -C link-arg=-fuse-ld=lld-18
+            -C linker=clang-19
+            -C link-arg=-fuse-ld=lld-19
             -C link-arg=-ldl
             -C link-arg=-Wl,--allow-shlib-undefined
             -C link-arg=-Wl,--thinlto-cache-dir=$(pwd)/target/release/lto-cache
@@ -316,8 +310,8 @@ jobs:
           __1
           RUSTDOCFLAGS<<__1
             -C linker-plugin-lto=true
-            -C linker=clang-18
-            -C link-arg=-fuse-ld=lld-18
+            -C linker=clang-19
+            -C link-arg=-fuse-ld=lld-19
             -C link-arg=-ldl
             -C link-arg=-Wl,--allow-shlib-undefined
             -C link-arg=-Wl,--thinlto-cache-dir=$(pwd)/target/release/lto-cache
@@ -325,7 +319,7 @@ jobs:
             --cfg tokio_unstable
             $RUSTFLAGS
           __1
-          CC=/usr/bin/clang-18
+          CC=/usr/bin/clang-19
           CFLAGS=-flto=thin $CFLAGS
           " > $GITHUB_ENV
       - name: Remove macOS cURL --ipv4 flag
@@ -367,8 +361,8 @@ jobs:
           path: |-
             ~/.cargo/registry/index
             ~/.cargo/registry/cache
-          key: '15-cargo-home-${{ matrix.os }}-${{ matrix.arch }}-${{ hashFiles(''Cargo.lock'') }}'
-          restore-keys: '15-cargo-home-${{ matrix.os }}-${{ matrix.arch }}'
+          key: '25-cargo-home-${{ matrix.os }}-${{ matrix.arch }}-${{ hashFiles(''Cargo.lock'') }}'
+          restore-keys: '25-cargo-home-${{ matrix.os }}-${{ matrix.arch }}'
         if: '!(matrix.skip)'
       - name: Restore cache build output (PR)
         uses: actions/cache/restore@v4
@@ -381,7 +375,7 @@ jobs:
             !./target/*/*.zip
             !./target/*/*.tar.gz
           key: never_saved
-          restore-keys: '15-cargo-target-${{ matrix.os }}-${{ matrix.arch }}-${{ matrix.profile }}-${{ matrix.job }}-'
+          restore-keys: '25-cargo-target-${{ matrix.os }}-${{ matrix.arch }}-${{ matrix.profile }}-${{ matrix.job }}-'
       - name: Apply and update mtime cache
         if: '!(matrix.skip) && (!startsWith(github.ref, ''refs/tags/''))'
         uses: ./.github/mtime_cache
@@ -449,8 +443,10 @@ jobs:
         run: |-
           cd target/release
           zip -r deno-${{ matrix.arch }}-unknown-linux-gnu.zip deno
+          shasum -a 256 deno-${{ matrix.arch }}-unknown-linux-gnu.zip > deno-${{ matrix.arch }}-unknown-linux-gnu.zip.sha256sum
           strip denort
           zip -r denort-${{ matrix.arch }}-unknown-linux-gnu.zip denort
+          shasum -a 256 denort-${{ matrix.arch }}-unknown-linux-gnu.zip > denort-${{ matrix.arch }}-unknown-linux-gnu.zip.sha256sum
           ./deno types > lib.deno.d.ts
       - name: Pre-release (mac)
         if: |-
@@ -466,8 +462,10 @@ jobs:
           rcodesign sign target/release/deno --code-signature-flags=runtime --p12-password="$APPLE_CODESIGN_PASSWORD" --p12-file=<(echo $APPLE_CODESIGN_KEY | base64 -d) --entitlements-xml-file=cli/entitlements.plist
           cd target/release
           zip -r deno-${{ matrix.arch }}-apple-darwin.zip deno
+          shasum -a 256 deno-${{ matrix.arch }}-apple-darwin.zip > deno-${{ matrix.arch }}-apple-darwin.zip.sha256sum
           strip denort
           zip -r denort-${{ matrix.arch }}-apple-darwin.zip denort
+          shasum -a 256 denort-${{ matrix.arch }}-apple-darwin.zip > denort-${{ matrix.arch }}-apple-darwin.zip.sha256sum
       - name: Pre-release (windows)
         if: |-
           !(matrix.skip) && (matrix.os == 'windows' &&
@@ -477,7 +475,9 @@ jobs:
         shell: pwsh
         run: |-
           Compress-Archive -CompressionLevel Optimal -Force -Path target/release/deno.exe -DestinationPath target/release/deno-${{ matrix.arch }}-pc-windows-msvc.zip
+          Get-FileHash target/release/deno-${{ matrix.arch }}-pc-windows-msvc.zip -Algorithm SHA256 | Format-List > target/release/deno-${{ matrix.arch }}-pc-windows-msvc.zip.sha256sum
           Compress-Archive -CompressionLevel Optimal -Force -Path target/release/denort.exe -DestinationPath target/release/denort-${{ matrix.arch }}-pc-windows-msvc.zip
+          Get-FileHash target/release/denort-${{ matrix.arch }}-pc-windows-msvc.zip -Algorithm SHA256 | Format-List > target/release/denort-${{ matrix.arch }}-pc-windows-msvc.zip.sha256sum
       - name: Upload canary to dl.deno.land
         if: |-
           !(matrix.skip) && (matrix.job == 'test' &&
@@ -486,6 +486,7 @@ jobs:
           github.ref == 'refs/heads/main')
         run: |-
           gsutil -h "Cache-Control: public, max-age=3600" cp ./target/release/*.zip gs://dl.deno.land/canary/$(git rev-parse HEAD)/
+          gsutil -h "Cache-Control: public, max-age=3600" cp ./target/release/*.sha256sum gs://dl.deno.land/canary/$(git rev-parse HEAD)/
           echo ${{ github.sha }} > canary-latest.txt
           gsutil -h "Cache-Control: no-cache" cp canary-latest.txt gs://dl.deno.land/canary-$(rustc -vV | sed -n "s|host: ||p")-latest.txt
       - name: Autobahn testsuite
@@ -615,7 +616,9 @@ jobs:
           matrix.profile == 'release' &&
           github.repository == 'denoland/deno' &&
           startsWith(github.ref, 'refs/tags/'))
-        run: 'gsutil -h "Cache-Control: public, max-age=3600" cp ./target/release/*.zip gs://dl.deno.land/release/${GITHUB_REF#refs/*/}/'
+        run: |-
+          gsutil -h "Cache-Control: public, max-age=3600" cp ./target/release/*.zip gs://dl.deno.land/release/${GITHUB_REF#refs/*/}/
+          gsutil -h "Cache-Control: public, max-age=3600" cp ./target/release/*.sha256sum gs://dl.deno.land/release/${GITHUB_REF#refs/*/}/
       - name: Upload release to dl.deno.land (windows)
         if: |-
           !(matrix.skip) && (matrix.os == 'windows' &&
@@ -625,7 +628,9 @@ jobs:
           startsWith(github.ref, 'refs/tags/'))
         env:
           CLOUDSDK_PYTHON: '${{env.pythonLocation}}\python.exe'
-        run: 'gsutil -h "Cache-Control: public, max-age=3600" cp ./target/release/*.zip gs://dl.deno.land/release/${GITHUB_REF#refs/*/}/'
+        run: |-
+          gsutil -h "Cache-Control: public, max-age=3600" cp ./target/release/*.zip gs://dl.deno.land/release/${GITHUB_REF#refs/*/}/
+          gsutil -h "Cache-Control: public, max-age=3600" cp ./target/release/*.sha256sum gs://dl.deno.land/release/${GITHUB_REF#refs/*/}/
       - name: Create release notes
         if: |-
           !(matrix.skip) && (matrix.job == 'test' &&
@@ -647,15 +652,25 @@ jobs:
         with:
           files: |-
             target/release/deno-x86_64-pc-windows-msvc.zip
+            target/release/deno-x86_64-pc-windows-msvc.zip.sha256sum
             target/release/denort-x86_64-pc-windows-msvc.zip
+            target/release/denort-x86_64-pc-windows-msvc.zip.sha256sum
             target/release/deno-x86_64-unknown-linux-gnu.zip
+            target/release/deno-x86_64-unknown-linux-gnu.zip.sha256sum
             target/release/denort-x86_64-unknown-linux-gnu.zip
+            target/release/denort-x86_64-unknown-linux-gnu.zip.sha256sum
             target/release/deno-x86_64-apple-darwin.zip
+            target/release/deno-x86_64-apple-darwin.zip.sha256sum
             target/release/denort-x86_64-apple-darwin.zip
+            target/release/denort-x86_64-apple-darwin.zip.sha256sum
             target/release/deno-aarch64-unknown-linux-gnu.zip
+            target/release/deno-aarch64-unknown-linux-gnu.zip.sha256sum
             target/release/denort-aarch64-unknown-linux-gnu.zip
+            target/release/denort-aarch64-unknown-linux-gnu.zip.sha256sum
             target/release/deno-aarch64-apple-darwin.zip
+            target/release/deno-aarch64-apple-darwin.zip.sha256sum
             target/release/denort-aarch64-apple-darwin.zip
+            target/release/denort-aarch64-apple-darwin.zip.sha256sum
             target/release/deno_src.tar.gz
             target/release/lib.deno.d.ts
           body_path: target/release/release-notes.md
@@ -668,11 +683,12 @@ jobs:
             ./target
             !./target/*/gn_out
             !./target/*/*.zip
+            !./target/*/*.sha256sum
             !./target/*/*.tar.gz
-          key: '15-cargo-target-${{ matrix.os }}-${{ matrix.arch }}-${{ matrix.profile }}-${{ matrix.job }}-${{ github.sha }}'
+          key: '25-cargo-target-${{ matrix.os }}-${{ matrix.arch }}-${{ matrix.profile }}-${{ matrix.job }}-${{ github.sha }}'
   publish-canary:
     name: publish canary
-    runs-on: ubuntu-22.04
+    runs-on: ubuntu-24.04
     needs:
       - build
     if: github.repository == 'denoland/deno' && github.ref == 'refs/heads/main'
diff --git a/.github/workflows/post_publish.yml b/.github/workflows/post_publish.yml
index c0db0906df..dd80b3637a 100644
--- a/.github/workflows/post_publish.yml
+++ b/.github/workflows/post_publish.yml
@@ -7,7 +7,7 @@ on:
 jobs:
   update-dl-version:
     name: update dl.deno.land version
-    runs-on: ubuntu-22.04
+    runs-on: ubuntu-24.04
     if: github.repository == 'denoland/deno'
     steps:
       - name: Authenticate with Google Cloud
diff --git a/.github/workflows/promote_to_release.yml b/.github/workflows/promote_to_release.yml
index 3dc15dc730..79fefa6d6c 100644
--- a/.github/workflows/promote_to_release.yml
+++ b/.github/workflows/promote_to_release.yml
@@ -40,7 +40,7 @@ jobs:
           project_id: denoland
 
       - name: Install deno
-        uses: denoland/setup-deno@v1
+        uses: denoland/setup-deno@v2
         with:
           deno-version: v1.x
 
diff --git a/.github/workflows/start_release.yml b/.github/workflows/start_release.yml
index 392551afbe..40a44bb61a 100644
--- a/.github/workflows/start_release.yml
+++ b/.github/workflows/start_release.yml
@@ -16,7 +16,7 @@ on:
 jobs:
   build:
     name: start release
-    runs-on: ubuntu-22.04
+    runs-on: ubuntu-24.04
     timeout-minutes: 30
 
     env:
@@ -34,7 +34,7 @@ jobs:
         uses: actions/checkout@v4
 
       - name: Install deno
-        uses: denoland/setup-deno@v1
+        uses: denoland/setup-deno@v2
         with:
           deno-version: v1.x
 
diff --git a/.github/workflows/version_bump.yml b/.github/workflows/version_bump.yml
index 733abbb024..9038fe0d22 100644
--- a/.github/workflows/version_bump.yml
+++ b/.github/workflows/version_bump.yml
@@ -16,7 +16,7 @@ on:
 jobs:
   build:
     name: version bump
-    runs-on: ubuntu-22.04
+    runs-on: ubuntu-24.04
     timeout-minutes: 90
 
     env:
@@ -39,7 +39,7 @@ jobs:
       - uses: dsherret/rust-toolchain-file@v1
 
       - name: Install deno
-        uses: denoland/setup-deno@v1
+        uses: denoland/setup-deno@v2
         with:
           deno-version: v1.x
 
diff --git a/.github/workflows/wpt_epoch.yml b/.github/workflows/wpt_epoch.yml
index c3c6277b93..1d86ed5557 100644
--- a/.github/workflows/wpt_epoch.yml
+++ b/.github/workflows/wpt_epoch.yml
@@ -20,7 +20,7 @@ jobs:
       fail-fast: false
       matrix:
         deno-version: [v1.x, canary]
-        os: [ubuntu-22.04-xl]
+        os: [ubuntu-24.04-xl]
 
     steps:
       - name: Clone repository
@@ -30,7 +30,7 @@ jobs:
           persist-credentials: false
 
       - name: Setup Deno
-        uses: denoland/setup-deno@v1
+        uses: denoland/setup-deno@v2
         with:
           deno-version: ${{ matrix.deno-version }}
 
diff --git a/Cargo.lock b/Cargo.lock
index 6ef9cd2e62..87265c02d8 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -128,19 +128,6 @@ version = "0.2.18"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "5c6cb57a04249c6480766f7f7cef5467412af1490f8d1e243141daddada3264f"
 
-[[package]]
-name = "ammonia"
-version = "3.3.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "64e6d1c7838db705c9b756557ee27c384ce695a1c51a6fe528784cb1c6840170"
-dependencies = [
- "html5ever",
- "maplit",
- "once_cell",
- "tendril",
- "url",
-]
-
 [[package]]
 name = "android_system_properties"
 version = "0.1.5"
@@ -360,6 +347,53 @@ version = "1.3.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "0c4b4d0bd25bd0b74681c0ad21497610ce1b7c91b1022cd21c80c6fbdd9476b0"
 
+[[package]]
+name = "axum"
+version = "0.7.5"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "3a6c9af12842a67734c9a2e355436e5d03b22383ed60cf13cd0c18fbfe3dcbcf"
+dependencies = [
+ "async-trait",
+ "axum-core",
+ "bytes",
+ "futures-util",
+ "http 1.1.0",
+ "http-body 1.0.0",
+ "http-body-util",
+ "itoa",
+ "matchit",
+ "memchr",
+ "mime",
+ "percent-encoding",
+ "pin-project-lite",
+ "rustversion",
+ "serde",
+ "sync_wrapper",
+ "tower",
+ "tower-layer",
+ "tower-service",
+]
+
+[[package]]
+name = "axum-core"
+version = "0.4.5"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "09f2bd6146b97ae3359fa0cc6d6b376d9539582c7b4220f041a33ec24c226199"
+dependencies = [
+ "async-trait",
+ "bytes",
+ "futures-util",
+ "http 1.1.0",
+ "http-body 1.0.0",
+ "http-body-util",
+ "mime",
+ "pin-project-lite",
+ "rustversion",
+ "sync_wrapper",
+ "tower-layer",
+ "tower-service",
+]
+
 [[package]]
 name = "backtrace"
 version = "0.3.73"
@@ -450,25 +484,22 @@ dependencies = [
 
 [[package]]
 name = "bindgen"
-version = "0.69.4"
+version = "0.70.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "a00dc851838a2120612785d195287475a3ac45514741da670b735818822129a0"
+checksum = "f49d8fed880d473ea71efb9bf597651e77201bdd4893efe54c9e5d65ae04ce6f"
 dependencies = [
  "bitflags 2.6.0",
  "cexpr",
  "clang-sys",
- "itertools 0.10.5",
- "lazy_static",
- "lazycell",
+ "itertools 0.13.0",
  "log",
- "prettyplease 0.2.17",
+ "prettyplease",
  "proc-macro2",
  "quote",
  "regex",
  "rustc-hash 1.1.0",
  "shlex",
  "syn 2.0.72",
- "which 4.4.2",
 ]
 
 [[package]]
@@ -631,12 +662,13 @@ dependencies = [
 
 [[package]]
 name = "cc"
-version = "1.1.10"
+version = "1.0.106"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e9e8aabfac534be767c909e0690571677d49f41bd8465ae876fe043d52ba5292"
+checksum = "066fce287b1d4eafef758e89e09d724a24808a9196fe9756b8ca90e86d0719a2"
 dependencies = [
  "jobserver",
  "libc",
+ "once_cell",
 ]
 
 [[package]]
@@ -688,7 +720,7 @@ checksum = "0b023947811758c97c59bf9d1c188fd619ad4718dcaa767947df1cadb14f39f4"
 dependencies = [
  "glob",
  "libc",
- "libloading 0.8.3",
+ "libloading 0.8.5",
 ]
 
 [[package]]
@@ -757,11 +789,13 @@ dependencies = [
  "fastwebsockets",
  "file_test_runner",
  "flaky_test",
+ "hickory-client",
+ "hickory-server",
  "http 1.1.0",
  "http-body-util",
  "hyper 1.4.1",
  "hyper-util",
- "nix 0.26.2",
+ "nix",
  "once_cell",
  "os_pipe",
  "pretty_assertions",
@@ -770,8 +804,6 @@ dependencies = [
  "serde",
  "test_server",
  "tokio",
- "trust-dns-client",
- "trust-dns-server",
  "url",
  "uuid",
  "zeromq",
@@ -840,9 +872,9 @@ checksum = "acbf1af155f9b9ef647e42cdc158db4b64a1b61f743629225fde6f3e0be2a7c7"
 
 [[package]]
 name = "comrak"
-version = "0.26.0"
+version = "0.28.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "395ab67843c57df5a4ee29d610740828dbc928cc64ecf0f2a1d5cd0e98e107a9"
+checksum = "c93ab3577cca16b4a1d80a88c2e0cd8b6e969e51696f0bbb0d1dcb0157109832"
 dependencies = [
  "caseless",
  "derive_builder",
@@ -1040,7 +1072,7 @@ dependencies = [
  "cpufeatures",
  "curve25519-dalek-derive",
  "digest",
- "fiat-crypto",
+ "fiat-crypto 0.2.7",
  "rustc_version 0.4.0",
  "subtle",
  "zeroize",
@@ -1064,7 +1096,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "b28bfe653d79bd16c77f659305b195b82bb5ce0c0eb2a4846b82ddbd77586813"
 dependencies = [
  "bitflags 2.6.0",
- "libloading 0.8.3",
+ "libloading 0.8.5",
  "winapi",
 ]
 
@@ -1110,7 +1142,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "978747c1d849a7d2ee5e8adc0159961c48fb7e5db2f06af6723b80123bb53856"
 dependencies = [
  "cfg-if",
- "hashbrown",
+ "hashbrown 0.14.5",
  "lock_api",
  "once_cell",
  "parking_lot_core",
@@ -1146,11 +1178,10 @@ dependencies = [
 
 [[package]]
 name = "deno"
-version = "2.0.0-rc.7"
+version = "2.0.6"
 dependencies = [
  "anstream",
  "async-trait",
- "base32",
  "base64 0.21.7",
  "bincode",
  "bytes",
@@ -1174,11 +1205,14 @@ dependencies = [
  "deno_lockfile",
  "deno_npm",
  "deno_package_json",
+ "deno_path_util",
+ "deno_resolver",
  "deno_runtime",
  "deno_semver",
  "deno_task_shell",
  "deno_terminal 0.2.0",
  "deno_tower_lsp",
+ "dhat",
  "dissimilar",
  "dotenvy",
  "dprint-plugin-json",
@@ -1186,7 +1220,6 @@ dependencies = [
  "dprint-plugin-markdown",
  "dprint-plugin-typescript",
  "env_logger",
- "eszip",
  "fancy-regex",
  "faster-hex",
  "flate2",
@@ -1198,7 +1231,7 @@ dependencies = [
  "http-body-util",
  "hyper-util",
  "import_map",
- "indexmap",
+ "indexmap 2.3.0",
  "jsonc-parser",
  "junction",
  "lazy-regex",
@@ -1211,8 +1244,7 @@ dependencies = [
  "markup_fmt",
  "memmem",
  "monch",
- "napi_sym",
- "nix 0.26.2",
+ "nix",
  "node_resolver",
  "notify",
  "once_cell",
@@ -1220,7 +1252,7 @@ dependencies = [
  "p256",
  "pathdiff",
  "percent-encoding",
- "phf 0.11.2",
+ "phf",
  "pretty_assertions",
  "pretty_yaml",
  "quick-junit",
@@ -1253,7 +1285,6 @@ dependencies = [
  "which 4.4.2",
  "winapi",
  "winres",
- "yoke",
  "zeromq",
  "zip",
  "zstd",
@@ -1272,9 +1303,9 @@ dependencies = [
 
 [[package]]
 name = "deno_ast"
-version = "0.42.0"
+version = "0.43.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "3b08d11d9e4086b00d3428650e31153cf5896586411763cb88a6423ce5b18791"
+checksum = "48d00b724e06d2081a141ec1155756a0b465d413d8e2a7515221f61d482eb2ee"
 dependencies = [
  "base64 0.21.7",
  "deno_media_type",
@@ -1316,7 +1347,7 @@ dependencies = [
 
 [[package]]
 name = "deno_bench_util"
-version = "0.162.0"
+version = "0.171.0"
 dependencies = [
  "bencher",
  "deno_core",
@@ -1325,34 +1356,38 @@ dependencies = [
 
 [[package]]
 name = "deno_broadcast_channel"
-version = "0.162.0"
+version = "0.171.0"
 dependencies = [
  "async-trait",
  "deno_core",
+ "thiserror",
  "tokio",
  "uuid",
 ]
 
 [[package]]
 name = "deno_cache"
-version = "0.100.0"
+version = "0.109.0"
 dependencies = [
  "async-trait",
  "deno_core",
  "rusqlite",
  "serde",
  "sha2",
+ "thiserror",
  "tokio",
 ]
 
 [[package]]
 name = "deno_cache_dir"
-version = "0.11.1"
+version = "0.13.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "6df43311cb7703fa3242c282823a850e4c8d0c06b9527d8209b55bd695452ea5"
+checksum = "08c1f52170cd7715f8006da54cde1444863a0d6fbd9c11d037a737db2dec8e22"
 dependencies = [
+ "base32",
  "deno_media_type",
- "indexmap",
+ "deno_path_util",
+ "indexmap 2.3.0",
  "log",
  "once_cell",
  "parking_lot",
@@ -1365,31 +1400,33 @@ dependencies = [
 
 [[package]]
 name = "deno_canvas"
-version = "0.37.0"
+version = "0.46.0"
 dependencies = [
  "deno_core",
  "deno_webgpu",
  "image",
  "serde",
+ "thiserror",
 ]
 
 [[package]]
 name = "deno_config"
-version = "0.35.0"
+version = "0.38.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "105864a9e0a7fbc22f1106784b2d263f402f157be1c3e1a9905f53d182700c9f"
+checksum = "966825073480a6ac7e01977a3879d13edc8d6ea2d65ea164b37156a5fb206e9a"
 dependencies = [
  "anyhow",
  "deno_package_json",
+ "deno_path_util",
  "deno_semver",
  "glob",
  "ignore",
  "import_map",
- "indexmap",
+ "indexmap 2.3.0",
  "jsonc-parser",
  "log",
  "percent-encoding",
- "phf 0.11.2",
+ "phf",
  "serde",
  "serde_json",
  "thiserror",
@@ -1398,16 +1435,16 @@ dependencies = [
 
 [[package]]
 name = "deno_console"
-version = "0.168.0"
+version = "0.177.0"
 dependencies = [
  "deno_core",
 ]
 
 [[package]]
 name = "deno_core"
-version = "0.311.0"
+version = "0.319.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5e09bd55da542fa1fde753aff617c355b5d782e763ab2a19e4371a56d7844cac"
+checksum = "e9dbb841f9850534320d8927dce53ca8d64bafbab5576c2a98f03f9e08534215"
 dependencies = [
  "anyhow",
  "bincode",
@@ -1420,7 +1457,7 @@ dependencies = [
  "deno_unsync",
  "futures",
  "libc",
- "memoffset 0.9.1",
+ "memoffset",
  "parking_lot",
  "percent-encoding",
  "pin-project",
@@ -1437,25 +1474,26 @@ dependencies = [
 
 [[package]]
 name = "deno_core_icudata"
-version = "0.0.73"
+version = "0.74.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "a13951ea98c0a4c372f162d669193b4c9d991512de9f2381dd161027f34b26b1"
+checksum = "fe4dccb6147bb3f3ba0c7a48e993bfeb999d2c2e47a81badee80e2b370c8d695"
 
 [[package]]
 name = "deno_cron"
-version = "0.48.0"
+version = "0.57.0"
 dependencies = [
  "anyhow",
  "async-trait",
  "chrono",
  "deno_core",
  "saffron",
+ "thiserror",
  "tokio",
 ]
 
 [[package]]
 name = "deno_crypto"
-version = "0.182.0"
+version = "0.191.0"
 dependencies = [
  "aes",
  "aes-gcm",
@@ -1467,6 +1505,7 @@ dependencies = [
  "curve25519-dalek",
  "deno_core",
  "deno_web",
+ "ed448-goldilocks",
  "elliptic-curve",
  "num-traits",
  "once_cell",
@@ -1483,17 +1522,18 @@ dependencies = [
  "sha2",
  "signature",
  "spki",
+ "thiserror",
+ "tokio",
  "uuid",
  "x25519-dalek",
 ]
 
 [[package]]
 name = "deno_doc"
-version = "0.150.0"
+version = "0.156.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "c762829006b555837691b7016828eb1f93acf0a4ff344357b946898ea5b5610d"
+checksum = "2585b98d6ad76dae30bf2d7b6d71b8363cae041158b8780d14a2f4fe17590a61"
 dependencies = [
- "ammonia",
  "anyhow",
  "cfg-if",
  "comrak",
@@ -1503,7 +1543,7 @@ dependencies = [
  "handlebars",
  "html-escape",
  "import_map",
- "indexmap",
+ "indexmap 2.3.0",
  "itoa",
  "lazy_static",
  "regex",
@@ -1515,7 +1555,7 @@ dependencies = [
 
 [[package]]
 name = "deno_fetch"
-version = "0.192.0"
+version = "0.201.0"
 dependencies = [
  "base64 0.21.7",
  "bytes",
@@ -1536,6 +1576,7 @@ dependencies = [
  "rustls-webpki",
  "serde",
  "serde_json",
+ "thiserror",
  "tokio",
  "tokio-rustls",
  "tokio-socks",
@@ -1547,7 +1588,7 @@ dependencies = [
 
 [[package]]
 name = "deno_ffi"
-version = "0.155.0"
+version = "0.164.0"
 dependencies = [
  "deno_core",
  "deno_permissions",
@@ -1556,37 +1597,42 @@ dependencies = [
  "libffi",
  "libffi-sys",
  "log",
+ "num-bigint",
  "serde",
  "serde-value",
  "serde_json",
+ "thiserror",
+ "tokio",
  "winapi",
 ]
 
 [[package]]
 name = "deno_fs"
-version = "0.78.0"
+version = "0.87.0"
 dependencies = [
  "async-trait",
  "base32",
  "deno_core",
  "deno_io",
+ "deno_path_util",
  "deno_permissions",
  "filetime",
  "junction",
  "libc",
- "nix 0.26.2",
+ "nix",
  "rand",
  "rayon",
  "serde",
+ "thiserror",
  "winapi",
  "windows-sys 0.52.0",
 ]
 
 [[package]]
 name = "deno_graph"
-version = "0.82.3"
+version = "0.84.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "938ed2efa1dd9fdcceeebc169b2b7910506b8dacc992cfdcffd84aa6a3eb8db0"
+checksum = "cd4f4a14aa069087be41c2998077b0453f0191747898f96e6343f700abfc2c18"
 dependencies = [
  "anyhow",
  "async-trait",
@@ -1597,7 +1643,7 @@ dependencies = [
  "encoding_rs",
  "futures",
  "import_map",
- "indexmap",
+ "indexmap 2.3.0",
  "log",
  "monch",
  "once_cell",
@@ -1613,7 +1659,7 @@ dependencies = [
 
 [[package]]
 name = "deno_http"
-version = "0.166.0"
+version = "0.175.0"
 dependencies = [
  "async-compression",
  "async-trait",
@@ -1638,7 +1684,7 @@ dependencies = [
  "mime",
  "once_cell",
  "percent-encoding",
- "phf 0.11.2",
+ "phf",
  "pin-project",
  "rand",
  "ring",
@@ -1652,7 +1698,7 @@ dependencies = [
 
 [[package]]
 name = "deno_io"
-version = "0.78.0"
+version = "0.87.0"
 dependencies = [
  "async-trait",
  "deno_core",
@@ -1673,7 +1719,7 @@ dependencies = [
 
 [[package]]
 name = "deno_kv"
-version = "0.76.0"
+version = "0.85.0"
 dependencies = [
  "anyhow",
  "async-trait",
@@ -1682,6 +1728,7 @@ dependencies = [
  "chrono",
  "deno_core",
  "deno_fetch",
+ "deno_path_util",
  "deno_permissions",
  "deno_tls",
  "denokv_proto",
@@ -1697,14 +1744,15 @@ dependencies = [
  "rand",
  "rusqlite",
  "serde",
+ "thiserror",
  "url",
 ]
 
 [[package]]
 name = "deno_lint"
-version = "0.67.0"
+version = "0.68.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "871b60e32bfb6c110cbb9b0688dbf048f81e5d347fe4ce5a42239263de9dd938"
+checksum = "bb994e6d1b18223df0a756c7948143b35682941d615edffef60d5b38822f38ac"
 dependencies = [
  "anyhow",
  "deno_ast",
@@ -1712,7 +1760,7 @@ dependencies = [
  "if_chain",
  "log",
  "once_cell",
- "phf 0.11.2",
+ "phf",
  "regex",
  "serde",
  "serde_json",
@@ -1732,9 +1780,9 @@ dependencies = [
 
 [[package]]
 name = "deno_media_type"
-version = "0.1.4"
+version = "0.2.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "a8978229b82552bf8457a0125aa20863f023619cfc21ebb007b1e571d68fd85b"
+checksum = "7fcf552fbdedbe81c89705349d7d2485c7051382b000dfddbdbf7fc25931cf83"
 dependencies = [
  "data-url",
  "serde",
@@ -1743,11 +1791,17 @@ dependencies = [
 
 [[package]]
 name = "deno_napi"
-version = "0.99.0"
+version = "0.108.0"
 dependencies = [
  "deno_core",
  "deno_permissions",
+ "libc",
  "libloading 0.7.4",
+ "libuv-sys-lite",
+ "log",
+ "napi_sym",
+ "thiserror",
+ "windows-sys 0.52.0",
 ]
 
 [[package]]
@@ -1765,23 +1819,24 @@ dependencies = [
 
 [[package]]
 name = "deno_net"
-version = "0.160.0"
+version = "0.169.0"
 dependencies = [
  "deno_core",
  "deno_permissions",
  "deno_tls",
+ "hickory-proto",
+ "hickory-resolver",
  "pin-project",
  "rustls-tokio-stream",
  "serde",
  "socket2",
+ "thiserror",
  "tokio",
- "trust-dns-proto",
- "trust-dns-resolver",
 ]
 
 [[package]]
 name = "deno_node"
-version = "0.105.0"
+version = "0.114.0"
 dependencies = [
  "aead-gcm-stream",
  "aes",
@@ -1800,6 +1855,7 @@ dependencies = [
  "deno_media_type",
  "deno_net",
  "deno_package_json",
+ "deno_path_util",
  "deno_permissions",
  "deno_whoami",
  "der",
@@ -1819,7 +1875,7 @@ dependencies = [
  "hyper 1.4.1",
  "hyper-util",
  "idna 0.3.0",
- "indexmap",
+ "indexmap 2.3.0",
  "ipnetwork",
  "k256",
  "lazy-regex",
@@ -1870,9 +1926,9 @@ dependencies = [
 
 [[package]]
 name = "deno_npm"
-version = "0.25.2"
+version = "0.25.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "1809e2d77d8a06bc2800dc10c1d4acb664197e518e289a86e336411c1feba785"
+checksum = "e6b4dc4a9f1cff63d5638e7d93042f24f46300d1cc77b86f3caaa699a7ddccf7"
 dependencies = [
  "anyhow",
  "async-trait",
@@ -1889,9 +1945,9 @@ dependencies = [
 
 [[package]]
 name = "deno_ops"
-version = "0.187.0"
+version = "0.195.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e040fd4def8a67538fe38c9955fd970efc9f44284bd69d44f8992a456afd665d"
+checksum = "797f348c38c07a5398bf790b280077c698e13fb49252f61ca6f6c5c616060292"
 dependencies = [
  "proc-macro-rules",
  "proc-macro2",
@@ -1904,23 +1960,35 @@ dependencies = [
 
 [[package]]
 name = "deno_package_json"
-version = "0.1.1"
+version = "0.1.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "38cf6ea5cc98ea7ad58b0e84593773bea03fc0431071a296017bed4151e3dc1d"
+checksum = "6cbc4c4d3eb0960b58e8f43f9fc2d3f620fcac9a03cd85203e08db5b04e83c1f"
 dependencies = [
  "deno_semver",
- "indexmap",
+ "indexmap 2.3.0",
  "serde",
  "serde_json",
  "thiserror",
  "url",
 ]
 
+[[package]]
+name = "deno_path_util"
+version = "0.2.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "ff25f6e08e7a0214bbacdd6f7195c7f1ebcd850c87a624e4ff06326b68b42d99"
+dependencies = [
+ "percent-encoding",
+ "thiserror",
+ "url",
+]
+
 [[package]]
 name = "deno_permissions"
-version = "0.28.0"
+version = "0.37.0"
 dependencies = [
  "deno_core",
+ "deno_path_util",
  "deno_terminal 0.2.0",
  "fqdn",
  "libc",
@@ -1928,14 +1996,35 @@ dependencies = [
  "once_cell",
  "percent-encoding",
  "serde",
+ "thiserror",
  "which 4.4.2",
  "winapi",
 ]
 
 [[package]]
-name = "deno_runtime"
-version = "0.177.0"
+name = "deno_resolver"
+version = "0.9.0"
 dependencies = [
+ "anyhow",
+ "base32",
+ "dashmap",
+ "deno_config",
+ "deno_media_type",
+ "deno_package_json",
+ "deno_path_util",
+ "deno_semver",
+ "node_resolver",
+ "test_server",
+ "thiserror",
+ "url",
+]
+
+[[package]]
+name = "deno_runtime"
+version = "0.186.0"
+dependencies = [
+ "async-trait",
+ "color-print",
  "deno_ast",
  "deno_broadcast_channel",
  "deno_cache",
@@ -1953,6 +2042,7 @@ dependencies = [
  "deno_napi",
  "deno_net",
  "deno_node",
+ "deno_path_util",
  "deno_permissions",
  "deno_terminal 0.2.0",
  "deno_tls",
@@ -1974,19 +2064,27 @@ dependencies = [
  "libc",
  "log",
  "netif",
- "nix 0.26.2",
+ "nix",
  "node_resolver",
  "notify",
  "ntapi",
  "once_cell",
+ "opentelemetry",
+ "opentelemetry-http",
+ "opentelemetry-otlp",
+ "opentelemetry-semantic-conventions",
+ "opentelemetry_sdk",
  "percent-encoding",
+ "pin-project",
  "regex",
  "rustyline",
+ "same-file",
  "serde",
  "signal-hook",
  "signal-hook-registry",
  "tempfile",
  "test_server",
+ "thiserror",
  "tokio",
  "tokio-metrics",
  "twox-hash",
@@ -1998,9 +2096,9 @@ dependencies = [
 
 [[package]]
 name = "deno_semver"
-version = "0.5.13"
+version = "0.5.16"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "6657fecb9ac6a7a71f552c95e8cc492466a75f5660224577e2226bcf30db9768"
+checksum = "c957c6a57c38b7dde2315df0da0ec228911e56a74f185b108a488d0401841a67"
 dependencies = [
  "monch",
  "once_cell",
@@ -2011,9 +2109,9 @@ dependencies = [
 
 [[package]]
 name = "deno_task_shell"
-version = "0.17.0"
+version = "0.18.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "dd6413ffc1654cad015edb5c4ab574069acdc929a6efafed23bc947901bcff1a"
+checksum = "4f444918f7102c1a5a143e9d57809e499fb4d365070519bf2e8bdb16d586af2a"
 dependencies = [
  "anyhow",
  "futures",
@@ -2048,7 +2146,7 @@ dependencies = [
 
 [[package]]
 name = "deno_tls"
-version = "0.155.0"
+version = "0.164.0"
 dependencies = [
  "deno_core",
  "deno_native_certs",
@@ -2057,6 +2155,7 @@ dependencies = [
  "rustls-tokio-stream",
  "rustls-webpki",
  "serde",
+ "thiserror",
  "tokio",
  "webpki-roots",
 ]
@@ -2096,18 +2195,19 @@ dependencies = [
 
 [[package]]
 name = "deno_url"
-version = "0.168.0"
+version = "0.177.0"
 dependencies = [
  "deno_bench_util",
  "deno_console",
  "deno_core",
  "deno_webidl",
+ "thiserror",
  "urlpattern",
 ]
 
 [[package]]
 name = "deno_web"
-version = "0.199.0"
+version = "0.208.0"
 dependencies = [
  "async-trait",
  "base64-simd 0.8.0",
@@ -2122,17 +2222,19 @@ dependencies = [
  "flate2",
  "futures",
  "serde",
+ "thiserror",
  "tokio",
  "uuid",
 ]
 
 [[package]]
 name = "deno_webgpu"
-version = "0.135.0"
+version = "0.144.0"
 dependencies = [
  "deno_core",
  "raw-window-handle",
  "serde",
+ "thiserror",
  "tokio",
  "wgpu-core",
  "wgpu-types",
@@ -2140,7 +2242,7 @@ dependencies = [
 
 [[package]]
 name = "deno_webidl"
-version = "0.168.0"
+version = "0.177.0"
 dependencies = [
  "deno_bench_util",
  "deno_core",
@@ -2148,7 +2250,7 @@ dependencies = [
 
 [[package]]
 name = "deno_websocket"
-version = "0.173.0"
+version = "0.182.0"
 dependencies = [
  "bytes",
  "deno_core",
@@ -2164,16 +2266,18 @@ dependencies = [
  "once_cell",
  "rustls-tokio-stream",
  "serde",
+ "thiserror",
  "tokio",
 ]
 
 [[package]]
 name = "deno_webstorage"
-version = "0.163.0"
+version = "0.172.0"
 dependencies = [
  "deno_core",
  "deno_web",
  "rusqlite",
+ "thiserror",
 ]
 
 [[package]]
@@ -2188,9 +2292,9 @@ dependencies = [
 
 [[package]]
 name = "denokv_proto"
-version = "0.8.2"
+version = "0.8.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "f629c77d2bf59e2e2a07fd7b14bfffae352a3813fbdcb801e72205741fb7625c"
+checksum = "f7ba1f99ed11a9c11e868a8521b1f71a7e1aba785d7f42ea9ecbdc01146c89ec"
 dependencies = [
  "anyhow",
  "async-trait",
@@ -2204,9 +2308,9 @@ dependencies = [
 
 [[package]]
 name = "denokv_remote"
-version = "0.8.1"
+version = "0.8.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "d57717b5123e8d1ec5f52973a67f98e3621274d362d18b245038967b402082df"
+checksum = "08ed833073189e8f6d03155fe3b05a024e75e29d8a28a4c2e9ec3b5c925e727b"
 dependencies = [
  "anyhow",
  "async-stream",
@@ -2229,9 +2333,9 @@ dependencies = [
 
 [[package]]
 name = "denokv_sqlite"
-version = "0.8.2"
+version = "0.8.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "3c4f5719e2bf698ec4f39fe29d91b62ff06a4b4a37ee481ffb8658d140fed986"
+checksum = "9b790f01d1302d53a0c3cbd27de88a06b3abd64ec8ab8673924e490541c7c713"
 dependencies = [
  "anyhow",
  "async-stream",
@@ -2359,6 +2463,22 @@ version = "1.4.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "b6e854126756c496b8c81dec88f9a706b15b875c5849d4097a3854476b9fdf94"
 
+[[package]]
+name = "dhat"
+version = "0.3.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "98cd11d84628e233de0ce467de10b8633f4ddaecafadefc86e13b84b8739b827"
+dependencies = [
+ "backtrace",
+ "lazy_static",
+ "mintex",
+ "parking_lot",
+ "rustc-hash 1.1.0",
+ "serde",
+ "serde_json",
+ "thousands",
+]
+
 [[package]]
 name = "diff"
 version = "0.1.13"
@@ -2461,8 +2581,8 @@ checksum = "f3ab0dd2bedc109d25f0d21afb09b7d329f6c6fa83b095daf31d2d967e091548"
 dependencies = [
  "anyhow",
  "bumpalo",
- "hashbrown",
- "indexmap",
+ "hashbrown 0.14.5",
+ "indexmap 2.3.0",
  "rustc-hash 1.1.0",
  "serde",
  "unicode-width",
@@ -2480,9 +2600,9 @@ dependencies = [
 
 [[package]]
 name = "dprint-plugin-json"
-version = "0.19.3"
+version = "0.19.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "a19f4a9f2f548b2098b8ec597d7bb40af133b6e9a3187c1d3c4caa101b8c93c3"
+checksum = "57f91e594559b450b7c5d6a0ba9f3f9fe951c1ea371168f7c95973da3fdbd85a"
 dependencies = [
  "anyhow",
  "dprint-core",
@@ -2494,9 +2614,9 @@ dependencies = [
 
 [[package]]
 name = "dprint-plugin-jupyter"
-version = "0.1.3"
+version = "0.1.5"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "c67b0e54b552a4775c221b44ed33be918c400bd8041d1f044f947fbb01025cc0"
+checksum = "d0d20684e37b3824e2bc917cfcb14e2cdf88398eef507335d839cbd78172bfee"
 dependencies = [
  "anyhow",
  "dprint-core",
@@ -2522,9 +2642,9 @@ dependencies = [
 
 [[package]]
 name = "dprint-plugin-typescript"
-version = "0.93.0"
+version = "0.93.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e9308d98b923b7c0335c2ee1560199e3f2321b1be82803107b4ba4ed5dac46cc"
+checksum = "3ff29fd136541e59d51946f0d2d353fefc886776f61a799ebfb5838b06cef13b"
 dependencies = [
  "anyhow",
  "deno_ast",
@@ -2552,15 +2672,6 @@ dependencies = [
  "text_lines",
 ]
 
-[[package]]
-name = "drain"
-version = "0.1.2"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "9d105028bd2b5dfcb33318fd79a445001ead36004dd8dffef1bdd7e493d8bc1e"
-dependencies = [
- "tokio",
-]
-
 [[package]]
 name = "dsa"
 version = "0.6.3"
@@ -2658,6 +2769,18 @@ dependencies = [
  "zeroize",
 ]
 
+[[package]]
+name = "ed448-goldilocks"
+version = "0.8.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "06924531e9e90130842b012e447f85bdaf9161bc8a0f8092be8cb70b01ebe092"
+dependencies = [
+ "fiat-crypto 0.1.20",
+ "hex",
+ "subtle",
+ "zeroize",
+]
+
 [[package]]
 name = "editpe"
 version = "0.1.0"
@@ -2665,7 +2788,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "48cede2bb1b07dd598d269f973792c43e0cd92686d3b452bd6e01d7a8eb01211"
 dependencies = [
  "debug-ignore",
- "indexmap",
+ "indexmap 2.3.0",
  "log",
  "thiserror",
  "zerocopy",
@@ -2796,29 +2919,6 @@ version = "1.0.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "31ae425815400e5ed474178a7a22e275a9687086a12ca63ec793ff292d8fdae8"
 
-[[package]]
-name = "eszip"
-version = "0.78.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "d0546f00d41dbc6e90b50e922759c02559a897e59b683369c3a13519cd5108b6"
-dependencies = [
- "anyhow",
- "async-trait",
- "base64 0.21.7",
- "deno_ast",
- "deno_graph",
- "deno_npm",
- "deno_semver",
- "futures",
- "hashlink 0.8.4",
- "indexmap",
- "serde",
- "serde_json",
- "sha2",
- "thiserror",
- "url",
-]
-
 [[package]]
 name = "fallible-iterator"
 version = "0.3.0"
@@ -2920,6 +3020,12 @@ dependencies = [
  "subtle",
 ]
 
+[[package]]
+name = "fiat-crypto"
+version = "0.1.20"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "e825f6987101665dea6ec934c09ec6d721de7bc1bf92248e1d5810c8cd636b77"
+
 [[package]]
 name = "fiat-crypto"
 version = "0.2.7"
@@ -3103,16 +3209,6 @@ version = "2.0.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "e6d5a32815ae3f33302d95fdcb2ce17862f8c65363dcfd29360480ba1001fc9c"
 
-[[package]]
-name = "futf"
-version = "0.1.5"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "df420e2e84819663797d1ec6544b13c5be84629e7bb00dc960d6917db2987843"
-dependencies = [
- "mac",
- "new_debug_unreachable",
-]
-
 [[package]]
 name = "futures"
 version = "0.3.30"
@@ -3329,7 +3425,7 @@ checksum = "9c08c1f623a8d0b722b8b99f821eb0ba672a1618f0d3b16ddbee1cedd2dd8557"
 dependencies = [
  "bitflags 2.6.0",
  "gpu-descriptor-types",
- "hashbrown",
+ "hashbrown 0.14.5",
 ]
 
 [[package]]
@@ -3373,7 +3469,7 @@ dependencies = [
  "futures-sink",
  "futures-util",
  "http 0.2.12",
- "indexmap",
+ "indexmap 2.3.0",
  "slab",
  "tokio",
  "tokio-util",
@@ -3392,7 +3488,7 @@ dependencies = [
  "futures-sink",
  "futures-util",
  "http 1.1.0",
- "indexmap",
+ "indexmap 2.3.0",
  "slab",
  "tokio",
  "tokio-util",
@@ -3405,15 +3501,15 @@ version = "0.2.5"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "8588661a8607108a5ca69cab034063441a0413a0b041c13618a7dd348021ef6f"
 dependencies = [
- "hashbrown",
+ "hashbrown 0.14.5",
  "serde",
 ]
 
 [[package]]
 name = "handlebars"
-version = "5.1.2"
+version = "6.1.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "d08485b96a0e6393e9e4d1b8d48cf74ad6c063cd905eb33f42c1ce3f0377539b"
+checksum = "ce25b617d1375ef96eeb920ae717e3da34a02fc979fe632c75128350f9e1f74a"
 dependencies = [
  "heck 0.5.0",
  "log",
@@ -3424,6 +3520,12 @@ dependencies = [
  "thiserror",
 ]
 
+[[package]]
+name = "hashbrown"
+version = "0.12.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "8a9ee70c43aaf417c914396645a0fa852624801b24ebb7ae78fe8272889ac888"
+
 [[package]]
 name = "hashbrown"
 version = "0.14.5"
@@ -3434,22 +3536,13 @@ dependencies = [
  "allocator-api2",
 ]
 
-[[package]]
-name = "hashlink"
-version = "0.8.4"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e8094feaf31ff591f651a2664fb9cfd92bba7a60ce3197265e9482ebe753c8f7"
-dependencies = [
- "hashbrown",
-]
-
 [[package]]
 name = "hashlink"
 version = "0.9.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "6ba4ff7128dee98c7dc9794b6a411377e1404dba1c97deb8d1a55297bd25d8af"
 dependencies = [
- "hashbrown",
+ "hashbrown 0.14.5",
 ]
 
 [[package]]
@@ -3482,6 +3575,92 @@ version = "0.2.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "dfa686283ad6dd069f105e5ab091b04c62850d3e4cf5d67debad1933f55023df"
 
+[[package]]
+name = "hickory-client"
+version = "0.24.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "bab9683b08d8f8957a857b0236455d80e1886eaa8c6178af556aa7871fb61b55"
+dependencies = [
+ "cfg-if",
+ "data-encoding",
+ "futures-channel",
+ "futures-util",
+ "hickory-proto",
+ "once_cell",
+ "radix_trie",
+ "rand",
+ "thiserror",
+ "tokio",
+ "tracing",
+]
+
+[[package]]
+name = "hickory-proto"
+version = "0.24.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "07698b8420e2f0d6447a436ba999ec85d8fbf2a398bbd737b82cac4a2e96e512"
+dependencies = [
+ "async-trait",
+ "cfg-if",
+ "data-encoding",
+ "enum-as-inner",
+ "futures-channel",
+ "futures-io",
+ "futures-util",
+ "idna 0.4.0",
+ "ipnet",
+ "once_cell",
+ "rand",
+ "serde",
+ "thiserror",
+ "tinyvec",
+ "tokio",
+ "tracing",
+ "url",
+]
+
+[[package]]
+name = "hickory-resolver"
+version = "0.24.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "28757f23aa75c98f254cf0405e6d8c25b831b32921b050a66692427679b1f243"
+dependencies = [
+ "cfg-if",
+ "futures-util",
+ "hickory-proto",
+ "ipconfig",
+ "lru-cache",
+ "once_cell",
+ "parking_lot",
+ "rand",
+ "resolv-conf",
+ "serde",
+ "smallvec",
+ "thiserror",
+ "tokio",
+ "tracing",
+]
+
+[[package]]
+name = "hickory-server"
+version = "0.24.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "9be0e43c556b9b3fdb6c7c71a9a32153a2275d02419e3de809e520bfcfe40c37"
+dependencies = [
+ "async-trait",
+ "bytes",
+ "cfg-if",
+ "enum-as-inner",
+ "futures-util",
+ "hickory-proto",
+ "serde",
+ "thiserror",
+ "time",
+ "tokio",
+ "tokio-util",
+ "tracing",
+]
+
 [[package]]
 name = "hkdf"
 version = "0.12.4"
@@ -3526,10 +3705,10 @@ version = "0.2.9"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "5a9de2bdef6354361892492bab5e316b2d78a0ee9971db4d36da9b1eb0e11999"
 dependencies = [
- "hashbrown",
+ "hashbrown 0.14.5",
  "new_debug_unreachable",
  "once_cell",
- "phf 0.11.2",
+ "phf",
  "rustc-hash 1.1.0",
  "triomphe",
 ]
@@ -3543,20 +3722,6 @@ dependencies = [
  "utf8-width",
 ]
 
-[[package]]
-name = "html5ever"
-version = "0.26.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "bea68cab48b8459f17cf1c944c67ddc572d272d9f2b274140f223ecb1da4a3b7"
-dependencies = [
- "log",
- "mac",
- "markup5ever",
- "proc-macro2",
- "quote",
- "syn 1.0.109",
-]
-
 [[package]]
 name = "http"
 version = "0.2.12"
@@ -3694,6 +3859,19 @@ dependencies = [
  "webpki-roots",
 ]
 
+[[package]]
+name = "hyper-timeout"
+version = "0.5.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "3203a961e5c83b6f5498933e78b6b263e208c197b63e9c6c53cc82ffd3f63793"
+dependencies = [
+ "hyper 1.4.1",
+ "hyper-util",
+ "pin-project-lite",
+ "tokio",
+ "tower-service",
+]
+
 [[package]]
 name = "hyper-util"
 version = "0.1.7"
@@ -3782,7 +3960,7 @@ version = "0.20.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "351a787decc56f38d65d16d32687265045d6d6a4531b4a0e1b649def3590354e"
 dependencies = [
- "indexmap",
+ "indexmap 2.3.0",
  "log",
  "percent-encoding",
  "serde",
@@ -3791,6 +3969,16 @@ dependencies = [
  "url",
 ]
 
+[[package]]
+name = "indexmap"
+version = "1.9.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "bd070e393353796e801d209ad339e89596eb4c8d430d18ede6a1cced8fafbd99"
+dependencies = [
+ "autocfg",
+ "hashbrown 0.12.3",
+]
+
 [[package]]
 name = "indexmap"
 version = "2.3.0"
@@ -3798,7 +3986,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "de3fc2e30ba82dd1b3911c8de1ffc143c74a914a14e99514d7637e3099df5ea0"
 dependencies = [
  "equivalent",
- "hashbrown",
+ "hashbrown 0.14.5",
  "serde",
 ]
 
@@ -3957,9 +4145,9 @@ dependencies = [
 
 [[package]]
 name = "jsonc-parser"
-version = "0.23.0"
+version = "0.26.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "7725c320caac8c21d8228c1d055af27a995d371f78cc763073d3e068323641b5"
+checksum = "b558af6b49fd918e970471374e7a798b2c9bbcda624a210ffa3901ee5614bc8e"
 dependencies = [
  "serde_json",
 ]
@@ -3974,6 +4162,19 @@ dependencies = [
  "winapi",
 ]
 
+[[package]]
+name = "jupyter-serde"
+version = "0.4.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "dd71aa17c4fa65e6d7536ab2728881a41f8feb2ee5841c2240516c3c3d65d8b3"
+dependencies = [
+ "anyhow",
+ "serde",
+ "serde_json",
+ "thiserror",
+ "uuid",
+]
+
 [[package]]
 name = "k256"
 version = "0.13.3"
@@ -4004,7 +4205,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "6aae1df220ece3c0ada96b8153459b67eebe9ae9212258bb0134ae60416fdf76"
 dependencies = [
  "libc",
- "libloading 0.8.3",
+ "libloading 0.8.5",
  "pkg-config",
 ]
 
@@ -4066,12 +4267,6 @@ dependencies = [
  "spin",
 ]
 
-[[package]]
-name = "lazycell"
-version = "1.3.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "830d08ce1d1d941e6b30645f1a0eb5643013d835ce3779a5fc208261dbe10f55"
-
 [[package]]
 name = "libc"
 version = "0.2.153"
@@ -4109,9 +4304,9 @@ dependencies = [
 
 [[package]]
 name = "libloading"
-version = "0.8.3"
+version = "0.8.5"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "0c2a198fb6b0eada2a8df47933734e6d35d350665a33a3593d7164fa52c75c19"
+checksum = "4979f22fdb869068da03c9f7528f8297c6fd2606bc3a4affe42e6a823fdb8da4"
 dependencies = [
  "cfg-if",
  "windows-targets 0.52.4",
@@ -4135,9 +4330,9 @@ dependencies = [
 
 [[package]]
 name = "libsqlite3-sys"
-version = "0.30.1"
+version = "0.30.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "2e99fb7a497b1e3339bc746195567ed8d3e24945ecd636e3619d20b9de9e9149"
+checksum = "6b694a822684ddb75df4d657029161431bcb4a85c1856952f845b76912bc6fec"
 dependencies = [
  "cc",
  "pkg-config",
@@ -4146,9 +4341,9 @@ dependencies = [
 
 [[package]]
 name = "libsui"
-version = "0.3.1"
+version = "0.5.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "56e39af24eff8df7c8b9980ef56a1a1f4d2e77b34b2d5c0529f108c53ae96a7a"
+checksum = "89795977654ad6250d6c0915411b622bac22f9efb4f852af94b2e00964cab832"
 dependencies = [
  "editpe",
  "libc",
@@ -4158,10 +4353,20 @@ dependencies = [
 ]
 
 [[package]]
-name = "libz-sys"
-version = "1.1.16"
+name = "libuv-sys-lite"
+version = "1.48.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5e143b5e666b2695d28f6bca6497720813f699c9602dd7f5cac91008b8ada7f9"
+checksum = "ca8dfd1a173826d193e3b955e07c22765829890f62c677a59c4a410cb4f47c01"
+dependencies = [
+ "bindgen",
+ "libloading 0.8.5",
+]
+
+[[package]]
+name = "libz-sys"
+version = "1.1.20"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "d2d16453e800a8cf6dd2fc3eb4bc99b786a9b90c663b8559a5b1a041bf89e472"
 dependencies = [
  "cc",
  "cmake",
@@ -4229,12 +4434,6 @@ dependencies = [
  "serde_repr",
 ]
 
-[[package]]
-name = "mac"
-version = "0.1.1"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "c41e0c4fef86961ac6d6f8a82609f55f31b05e4fce149ac5710e439df7619ba4"
-
 [[package]]
 name = "malloc_buf"
 version = "0.0.6"
@@ -4246,9 +4445,9 @@ dependencies = [
 
 [[package]]
 name = "malva"
-version = "0.10.1"
+version = "0.11.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "484beda6e5d775ed06a8ec0fce79e51d39f49d834ed2a29da3f437079321804f"
+checksum = "1c67b97ed99f56b86fa3c010843441f1fcdb71884bab96b8551bb3d1e7c6d529"
 dependencies = [
  "aho-corasick",
  "itertools 0.13.0",
@@ -4257,31 +4456,11 @@ dependencies = [
  "tiny_pretty",
 ]
 
-[[package]]
-name = "maplit"
-version = "1.0.2"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "3e2e65a1a2e43cfcb47a895c4c8b10d1f4a61097f9f254f183aee60cad9c651d"
-
-[[package]]
-name = "markup5ever"
-version = "0.11.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "7a2629bb1404f3d34c2e921f21fd34ba00b206124c81f65c50b43b6aaefeb016"
-dependencies = [
- "log",
- "phf 0.10.1",
- "phf_codegen",
- "string_cache",
- "string_cache_codegen",
- "tendril",
-]
-
 [[package]]
 name = "markup_fmt"
-version = "0.13.1"
+version = "0.15.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "9dab5ae899659fbe5c8835b2c8ca8d3e357974a3e454138925b404004973361f"
+checksum = "ebae65c91eab3d42231232bf48107f351e5a8d511454927218c53aeb68bbdb6f"
 dependencies = [
  "aho-corasick",
  "css_dataset",
@@ -4296,6 +4475,12 @@ version = "0.1.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "ffbee8634e0d45d258acb448e7eaab3fce7a0a467395d4d9f228e3c1f01fb2e4"
 
+[[package]]
+name = "matchit"
+version = "0.7.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "0e7465ac9959cc2b1404e8e2367b43684a6d13790fe23056cc8c6c5a6b7bcb94"
+
 [[package]]
 name = "md-5"
 version = "0.10.6"
@@ -4336,15 +4521,6 @@ version = "0.1.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "a64a92489e2744ce060c349162be1c5f33c6969234104dbd99ddb5feb08b8c15"
 
-[[package]]
-name = "memoffset"
-version = "0.7.1"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5de893c32cde5f383baa4c04c5d6dbdd735cfd4a794b0debdb2bb1b421da5ff4"
-dependencies = [
- "autocfg",
-]
-
 [[package]]
 name = "memoffset"
 version = "0.9.1"
@@ -4391,6 +4567,12 @@ dependencies = [
  "simd-adler32",
 ]
 
+[[package]]
+name = "mintex"
+version = "0.1.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "9bec4598fddb13cc7b528819e697852653252b760f1228b7642679bf2ff2cd07"
+
 [[package]]
 name = "mio"
 version = "0.8.11"
@@ -4426,7 +4608,7 @@ dependencies = [
  "bitflags 2.6.0",
  "codespan-reporting",
  "hexf-parse",
- "indexmap",
+ "indexmap 2.3.0",
  "log",
  "num-traits",
  "rustc-hash 1.1.0",
@@ -4454,7 +4636,7 @@ dependencies = [
 
 [[package]]
 name = "napi_sym"
-version = "0.98.0"
+version = "0.107.0"
 dependencies = [
  "quote",
  "serde",
@@ -4496,20 +4678,6 @@ dependencies = [
  "smallvec",
 ]
 
-[[package]]
-name = "nix"
-version = "0.26.2"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "bfdda3d196821d6af13126e40375cdf7da646a96114af134d5f417a9a1dc8e1a"
-dependencies = [
- "bitflags 1.3.2",
- "cfg-if",
- "libc",
- "memoffset 0.7.1",
- "pin-utils",
- "static_assertions",
-]
-
 [[package]]
 name = "nix"
 version = "0.27.1"
@@ -4523,12 +4691,13 @@ dependencies = [
 
 [[package]]
 name = "node_resolver"
-version = "0.7.0"
+version = "0.16.0"
 dependencies = [
  "anyhow",
  "async-trait",
  "deno_media_type",
  "deno_package_json",
+ "deno_path_util",
  "futures",
  "lazy-regex",
  "once_cell",
@@ -4743,6 +4912,93 @@ version = "0.1.5"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "ff011a302c396a5197692431fc1948019154afc178baf7d8e37367442a4601cf"
 
+[[package]]
+name = "opentelemetry"
+version = "0.27.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "0f3cebff57f7dbd1255b44d8bddc2cebeb0ea677dbaa2e25a3070a91b318f660"
+dependencies = [
+ "futures-core",
+ "futures-sink",
+ "js-sys",
+ "once_cell",
+ "pin-project-lite",
+ "thiserror",
+]
+
+[[package]]
+name = "opentelemetry-http"
+version = "0.27.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "10a8a7f5f6ba7c1b286c2fbca0454eaba116f63bbe69ed250b642d36fbb04d80"
+dependencies = [
+ "async-trait",
+ "bytes",
+ "http 1.1.0",
+ "opentelemetry",
+]
+
+[[package]]
+name = "opentelemetry-otlp"
+version = "0.27.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "91cf61a1868dacc576bf2b2a1c3e9ab150af7272909e80085c3173384fe11f76"
+dependencies = [
+ "async-trait",
+ "futures-core",
+ "http 1.1.0",
+ "opentelemetry",
+ "opentelemetry-http",
+ "opentelemetry-proto",
+ "opentelemetry_sdk",
+ "prost",
+ "serde_json",
+ "thiserror",
+ "tokio",
+ "tonic",
+ "tracing",
+]
+
+[[package]]
+name = "opentelemetry-proto"
+version = "0.27.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "a6e05acbfada5ec79023c85368af14abd0b307c015e9064d249b2a950ef459a6"
+dependencies = [
+ "hex",
+ "opentelemetry",
+ "opentelemetry_sdk",
+ "prost",
+ "serde",
+ "tonic",
+]
+
+[[package]]
+name = "opentelemetry-semantic-conventions"
+version = "0.27.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "bc1b6902ff63b32ef6c489e8048c5e253e2e4a803ea3ea7e783914536eb15c52"
+
+[[package]]
+name = "opentelemetry_sdk"
+version = "0.27.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "27b742c1cae4693792cc564e58d75a2a0ba29421a34a85b50da92efa89ecb2bc"
+dependencies = [
+ "async-trait",
+ "futures-channel",
+ "futures-executor",
+ "futures-util",
+ "glob",
+ "once_cell",
+ "opentelemetry",
+ "percent-encoding",
+ "rand",
+ "serde_json",
+ "thiserror",
+ "tracing",
+]
+
 [[package]]
 name = "option-ext"
 version = "0.2.0"
@@ -4968,16 +5224,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "e1d3afd2628e69da2be385eb6f2fd57c8ac7977ceeff6dc166ff1657b0e386a9"
 dependencies = [
  "fixedbitset",
- "indexmap",
-]
-
-[[package]]
-name = "phf"
-version = "0.10.1"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "fabbf1ead8a5bcbc20f5f8b939ee3f5b0f6f281b6ad3468b84656b658b455259"
-dependencies = [
- "phf_shared 0.10.0",
+ "indexmap 2.3.0",
 ]
 
 [[package]]
@@ -4987,27 +5234,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "ade2d8b8f33c7333b51bcf0428d37e217e9f32192ae4772156f65063b8ce03dc"
 dependencies = [
  "phf_macros",
- "phf_shared 0.11.2",
-]
-
-[[package]]
-name = "phf_codegen"
-version = "0.10.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "4fb1c3a8bc4dd4e5cfce29b44ffc14bedd2ee294559a294e2a4d4c9e9a6a13cd"
-dependencies = [
- "phf_generator 0.10.0",
- "phf_shared 0.10.0",
-]
-
-[[package]]
-name = "phf_generator"
-version = "0.10.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5d5285893bb5eb82e6aaf5d59ee909a06a16737a8970984dd7746ba9283498d6"
-dependencies = [
- "phf_shared 0.10.0",
- "rand",
+ "phf_shared",
 ]
 
 [[package]]
@@ -5016,7 +5243,7 @@ version = "0.11.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "48e4cc64c2ad9ebe670cb8fd69dd50ae301650392e81c05f9bfcb2d5bdbc24b0"
 dependencies = [
- "phf_shared 0.11.2",
+ "phf_shared",
  "rand",
 ]
 
@@ -5026,22 +5253,13 @@ version = "0.11.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "3444646e286606587e49f3bcf1679b8cef1dc2c5ecc29ddacaffc305180d464b"
 dependencies = [
- "phf_generator 0.11.2",
- "phf_shared 0.11.2",
+ "phf_generator",
+ "phf_shared",
  "proc-macro2",
  "quote",
  "syn 2.0.72",
 ]
 
-[[package]]
-name = "phf_shared"
-version = "0.10.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b6796ad771acdc0123d2a88dc428b5e38ef24456743ddb1744ed628f9815c096"
-dependencies = [
- "siphasher",
-]
-
 [[package]]
 name = "phf_shared"
 version = "0.11.2"
@@ -5164,12 +5382,6 @@ version = "0.2.17"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "5b40af805b3121feab8a3c29f04d8ad262fa8e0561883e7653e024ae4479e6de"
 
-[[package]]
-name = "precomputed-hash"
-version = "0.1.1"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "925383efa346730478fb4838dbe9137d2a47675ad789c546d150a6e1dd4ab31c"
-
 [[package]]
 name = "pretty_assertions"
 version = "1.4.0"
@@ -5191,16 +5403,6 @@ dependencies = [
  "yaml_parser",
 ]
 
-[[package]]
-name = "prettyplease"
-version = "0.1.25"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "6c8646e95016a7a6c4adea95bafa8a16baab64b583356217f2c85db4a39d9a86"
-dependencies = [
- "proc-macro2",
- "syn 1.0.109",
-]
-
 [[package]]
 name = "prettyplease"
 version = "0.2.17"
@@ -5284,9 +5486,9 @@ checksum = "43d84d1d7a6ac92673717f9f6d1518374ef257669c24ebc5ac25d5033828be58"
 
 [[package]]
 name = "prost"
-version = "0.11.9"
+version = "0.13.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "0b82eaa1d779e9a4bc1c3217db8ffbeabaae1dca241bf70183242128d48681cd"
+checksum = "7b0487d90e047de87f984913713b85c601c05609aad5b0df4b4573fbf69aa13f"
 dependencies = [
  "bytes",
  "prost-derive",
@@ -5294,44 +5496,43 @@ dependencies = [
 
 [[package]]
 name = "prost-build"
-version = "0.11.9"
+version = "0.13.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "119533552c9a7ffacc21e099c24a0ac8bb19c2a2a3f363de84cd9b844feab270"
+checksum = "0c1318b19085f08681016926435853bbf7858f9c082d0999b80550ff5d9abe15"
 dependencies = [
  "bytes",
- "heck 0.4.1",
- "itertools 0.10.5",
- "lazy_static",
+ "heck 0.5.0",
+ "itertools 0.13.0",
  "log",
  "multimap",
+ "once_cell",
  "petgraph",
- "prettyplease 0.1.25",
+ "prettyplease",
  "prost",
  "prost-types",
  "regex",
- "syn 1.0.109",
+ "syn 2.0.72",
  "tempfile",
- "which 4.4.2",
 ]
 
 [[package]]
 name = "prost-derive"
-version = "0.11.9"
+version = "0.13.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e5d2d8d10f3c6ded6da8b05b5fb3b8a5082514344d56c9f871412d29b4e075b4"
+checksum = "e9552f850d5f0964a4e4d0bf306459ac29323ddfbae05e35a7c0d35cb0803cc5"
 dependencies = [
  "anyhow",
- "itertools 0.10.5",
+ "itertools 0.13.0",
  "proc-macro2",
  "quote",
- "syn 1.0.109",
+ "syn 2.0.72",
 ]
 
 [[package]]
 name = "prost-types"
-version = "0.11.9"
+version = "0.13.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "213622a1460818959ac1181aaeb2dc9c7f63df720db7d788b3e24eacd1983e13"
+checksum = "4759aa0d3a6232fb8dbdb97b61de2c20047c68aca932c7ed76da9d788508d670"
 dependencies = [
  "prost",
 ]
@@ -5389,7 +5590,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "d1a341ae463320e9f8f34adda49c8a85d81d4e8f34cce4397fb0350481552224"
 dependencies = [
  "chrono",
- "indexmap",
+ "indexmap 2.3.0",
  "quick-xml",
  "strip-ansi-escapes",
  "thiserror",
@@ -5751,8 +5952,8 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "32a58fa8a7ccff2aec4f39cc45bf5f985cec7125ab271cf681c279fd00192b49"
 dependencies = [
  "countme",
- "hashbrown",
- "memoffset 0.9.1",
+ "hashbrown 0.14.5",
+ "memoffset",
  "rustc-hash 1.1.0",
  "text-size",
 ]
@@ -5779,9 +5980,9 @@ dependencies = [
 
 [[package]]
 name = "runtimelib"
-version = "0.14.0"
+version = "0.19.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "0c3d817764e3971867351e6103955b17d808f5330e9ef63aaaaab55bf8c664c1"
+checksum = "fe23ba9967355bbb1be2fb9a8e51bd239ffdf9c791fad5a9b765122ee2bde2e4"
 dependencies = [
  "anyhow",
  "base64 0.22.1",
@@ -5791,6 +5992,7 @@ dependencies = [
  "dirs",
  "futures",
  "glob",
+ "jupyter-serde",
  "rand",
  "ring",
  "serde",
@@ -5803,14 +6005,14 @@ dependencies = [
 
 [[package]]
 name = "rusqlite"
-version = "0.32.1"
+version = "0.32.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "7753b721174eb8ff87a9a0e799e2d7bc3749323e773db92e0984debb00019d6e"
+checksum = "1cdbe9230a57259b37f7257d0aff38b8c9dbda3513edba2105e59b130189d82f"
 dependencies = [
  "bitflags 2.6.0",
  "fallible-iterator",
  "fallible-streaming-iterator",
- "hashlink 0.9.1",
+ "hashlink",
  "libsqlite3-sys",
  "smallvec",
 ]
@@ -5960,7 +6162,7 @@ dependencies = [
  "libc",
  "log",
  "memchr",
- "nix 0.27.1",
+ "nix",
  "radix_trie",
  "unicode-segmentation",
  "unicode-width",
@@ -6156,7 +6358,7 @@ version = "1.0.122"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "784b6203951c57ff748476b126ccb5e8e2959a5c19e5c617ab1956be3dbc68da"
 dependencies = [
- "indexmap",
+ "indexmap 2.3.0",
  "itoa",
  "memchr",
  "ryu",
@@ -6174,15 +6376,6 @@ dependencies = [
  "syn 2.0.72",
 ]
 
-[[package]]
-name = "serde_spanned"
-version = "0.6.6"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "79e674e01f999af37c49f70a6ede167a8a60b2503e56c5599532a65baa5969a0"
-dependencies = [
- "serde",
-]
-
 [[package]]
 name = "serde_urlencoded"
 version = "0.7.1"
@@ -6197,9 +6390,9 @@ dependencies = [
 
 [[package]]
 name = "serde_v8"
-version = "0.220.0"
+version = "0.228.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "6e7a65d91d79acc82aa229aeb084f4a39bda269069bc1520df40f679495388e4"
+checksum = "bfe23e75c9a167f4e9d67a90d9fcaa622d1eec9aecad526c270e99a92f6915ff"
 dependencies = [
  "num-bigint",
  "serde",
@@ -6500,32 +6693,6 @@ version = "1.1.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "a2eb9349b6444b326872e140eb1cf5e7c522154d69e7a0ffb0fb81c06b37543f"
 
-[[package]]
-name = "string_cache"
-version = "0.8.7"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "f91138e76242f575eb1d3b38b4f1362f10d3a43f47d182a5b359af488a02293b"
-dependencies = [
- "new_debug_unreachable",
- "once_cell",
- "parking_lot",
- "phf_shared 0.10.0",
- "precomputed-hash",
- "serde",
-]
-
-[[package]]
-name = "string_cache_codegen"
-version = "0.5.2"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "6bb30289b722be4ff74a408c3cc27edeaad656e06cb1fe8fa9231fa59c728988"
-dependencies = [
- "phf_generator 0.10.0",
- "phf_shared 0.10.0",
- "proc-macro2",
- "quote",
-]
-
 [[package]]
 name = "string_enum"
 version = "0.4.4"
@@ -6588,7 +6755,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "adc8bd3075d1c6964010333fae9ddcd91ad422a4f8eb8b3206a9b2b6afb4209e"
 dependencies = [
  "bumpalo",
- "hashbrown",
+ "hashbrown 0.14.5",
  "ptr_meta",
  "rustc-hash 1.1.0",
  "triomphe",
@@ -6614,7 +6781,7 @@ checksum = "c77c112c218a09635d99a45802a81b4f341d6c28c81076aa2c29ba3bcd9151a9"
 dependencies = [
  "anyhow",
  "crc",
- "indexmap",
+ "indexmap 2.3.0",
  "is-macro",
  "once_cell",
  "parking_lot",
@@ -6684,7 +6851,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "4740e53eaf68b101203c1df0937d5161a29f3c13bceed0836ddfe245b72dd000"
 dependencies = [
  "anyhow",
- "indexmap",
+ "indexmap 2.3.0",
  "serde",
  "serde_json",
  "swc_cached",
@@ -6712,7 +6879,7 @@ dependencies = [
  "bitflags 2.6.0",
  "is-macro",
  "num-bigint",
- "phf 0.11.2",
+ "phf",
  "scoped-tls",
  "serde",
  "string_enum",
@@ -6776,7 +6943,7 @@ dependencies = [
  "new_debug_unreachable",
  "num-bigint",
  "num-traits",
- "phf 0.11.2",
+ "phf",
  "serde",
  "smallvec",
  "smartstring",
@@ -6796,9 +6963,9 @@ checksum = "65f21494e75d0bd8ef42010b47cabab9caaed8f2207570e809f6f4eb51a710d1"
 dependencies = [
  "better_scoped_tls",
  "bitflags 2.6.0",
- "indexmap",
+ "indexmap 2.3.0",
  "once_cell",
- "phf 0.11.2",
+ "phf",
  "rustc-hash 1.1.0",
  "serde",
  "smallvec",
@@ -6844,7 +7011,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "98d8447ea20ef76958a8240feef95743702485a84331e6df5bdbe7e383c87838"
 dependencies = [
  "dashmap",
- "indexmap",
+ "indexmap 2.3.0",
  "once_cell",
  "petgraph",
  "rustc-hash 1.1.0",
@@ -6889,7 +7056,7 @@ checksum = "76c76d8b9792ce51401d38da0fa62158d61f6d80d16d68fe5b03ce4bf5fba383"
 dependencies = [
  "base64 0.21.7",
  "dashmap",
- "indexmap",
+ "indexmap 2.3.0",
  "once_cell",
  "serde",
  "sha1",
@@ -6929,7 +7096,7 @@ version = "0.134.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "029eec7dd485923a75b5a45befd04510288870250270292fc2c1b3a9e7547408"
 dependencies = [
- "indexmap",
+ "indexmap 2.3.0",
  "num_cpus",
  "once_cell",
  "rustc-hash 1.1.0",
@@ -6974,7 +7141,7 @@ version = "0.25.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "357e2c97bb51431d65080f25b436bc4e2fc1a7f64a643bc21a8353e478dc799f"
 dependencies = [
- "indexmap",
+ "indexmap 2.3.0",
  "petgraph",
  "rustc-hash 1.1.0",
  "swc_common",
@@ -7127,17 +7294,6 @@ dependencies = [
  "windows-sys 0.52.0",
 ]
 
-[[package]]
-name = "tendril"
-version = "0.4.3"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "d24a120c5fc464a3458240ee02c299ebcb9d67b5249c8848b09d639dca8d7bb0"
-dependencies = [
- "futf",
- "mac",
- "utf-8",
-]
-
 [[package]]
 name = "termcolor"
 version = "1.4.1"
@@ -7169,6 +7325,7 @@ dependencies = [
 name = "test_napi"
 version = "0.1.0"
 dependencies = [
+ "libuv-sys-lite",
  "napi-build",
  "napi-sys",
  "test_server",
@@ -7185,6 +7342,7 @@ dependencies = [
  "console_static_text",
  "deno_unsync",
  "denokv_proto",
+ "faster-hex",
  "fastwebsockets",
  "flate2",
  "futures",
@@ -7199,7 +7357,7 @@ dependencies = [
  "libc",
  "lsp-types",
  "monch",
- "nix 0.26.2",
+ "nix",
  "once_cell",
  "os_pipe",
  "parking_lot",
@@ -7240,24 +7398,30 @@ dependencies = [
 
 [[package]]
 name = "thiserror"
-version = "1.0.61"
+version = "1.0.64"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "c546c80d6be4bc6a00c0f01730c08df82eaa7a7a61f11d656526506112cc1709"
+checksum = "d50af8abc119fb8bb6dbabcfa89656f46f84aa0ac7688088608076ad2b459a84"
 dependencies = [
  "thiserror-impl",
 ]
 
 [[package]]
 name = "thiserror-impl"
-version = "1.0.61"
+version = "1.0.64"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "46c3384250002a6d5af4d114f2845d37b57521033f30d5c3f46c4d70e1197533"
+checksum = "08904e7672f5eb876eaaf87e0ce17857500934f4981c4a0ab2b4aa98baac7fc3"
 dependencies = [
  "proc-macro2",
  "quote",
  "syn 2.0.72",
 ]
 
+[[package]]
+name = "thousands"
+version = "0.2.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "3bf63baf9f5039dadc247375c29eb13706706cfde997d0330d05aa63a77d8820"
+
 [[package]]
 name = "thread_local"
 version = "1.1.8"
@@ -7390,9 +7554,9 @@ dependencies = [
 
 [[package]]
 name = "tokio-stream"
-version = "0.1.15"
+version = "0.1.16"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "267ac89e0bec6e691e5813911606935d77c476ff49024f98abcea3e7b15e37af"
+checksum = "4f4e6ce100d0eb49a2734f8c0812bcd324cf357d21810932c5df6b96ef2b86f1"
 dependencies = [
  "futures-core",
  "pin-project-lite",
@@ -7410,7 +7574,7 @@ dependencies = [
  "futures-io",
  "futures-sink",
  "futures-util",
- "hashbrown",
+ "hashbrown 0.14.5",
  "pin-project-lite",
  "slab",
  "tokio",
@@ -7427,37 +7591,33 @@ dependencies = [
 ]
 
 [[package]]
-name = "toml"
-version = "0.7.8"
+name = "tonic"
+version = "0.12.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "dd79e69d3b627db300ff956027cc6c3798cef26d22526befdfcd12feeb6d2257"
+checksum = "877c5b330756d856ffcc4553ab34a5684481ade925ecc54bcd1bf02b1d0d4d52"
 dependencies = [
- "serde",
- "serde_spanned",
- "toml_datetime",
- "toml_edit",
-]
-
-[[package]]
-name = "toml_datetime"
-version = "0.6.6"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "4badfd56924ae69bcc9039335b2e017639ce3f9b001c393c1b2d1ef846ce2cbf"
-dependencies = [
- "serde",
-]
-
-[[package]]
-name = "toml_edit"
-version = "0.19.15"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "1b5bb770da30e5cbfde35a2d7b9b8a2c4b8ef89548a7a6aeab5c9a576e3e7421"
-dependencies = [
- "indexmap",
- "serde",
- "serde_spanned",
- "toml_datetime",
- "winnow 0.5.40",
+ "async-stream",
+ "async-trait",
+ "axum",
+ "base64 0.22.1",
+ "bytes",
+ "h2 0.4.4",
+ "http 1.1.0",
+ "http-body 1.0.0",
+ "http-body-util",
+ "hyper 1.4.1",
+ "hyper-timeout",
+ "hyper-util",
+ "percent-encoding",
+ "pin-project",
+ "prost",
+ "socket2",
+ "tokio",
+ "tokio-stream",
+ "tower",
+ "tower-layer",
+ "tower-service",
+ "tracing",
 ]
 
 [[package]]
@@ -7468,11 +7628,16 @@ checksum = "b8fa9be0de6cf49e536ce1851f987bd21a43b771b09473c3549a6c853db37c1c"
 dependencies = [
  "futures-core",
  "futures-util",
+ "indexmap 1.9.3",
  "pin-project",
  "pin-project-lite",
+ "rand",
+ "slab",
  "tokio",
+ "tokio-util",
  "tower-layer",
  "tower-service",
+ "tracing",
 ]
 
 [[package]]
@@ -7549,95 +7714,6 @@ dependencies = [
  "stable_deref_trait",
 ]
 
-[[package]]
-name = "trust-dns-client"
-version = "0.23.2"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "14135e72c7e6d4c9b6902d4437881a8598f0145dbb2e3f86f92dbad845b61e63"
-dependencies = [
- "cfg-if",
- "data-encoding",
- "futures-channel",
- "futures-util",
- "once_cell",
- "radix_trie",
- "rand",
- "thiserror",
- "tokio",
- "tracing",
- "trust-dns-proto",
-]
-
-[[package]]
-name = "trust-dns-proto"
-version = "0.23.2"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "3119112651c157f4488931a01e586aa459736e9d6046d3bd9105ffb69352d374"
-dependencies = [
- "async-trait",
- "cfg-if",
- "data-encoding",
- "enum-as-inner",
- "futures-channel",
- "futures-io",
- "futures-util",
- "idna 0.4.0",
- "ipnet",
- "once_cell",
- "rand",
- "serde",
- "smallvec",
- "thiserror",
- "tinyvec",
- "tokio",
- "tracing",
- "url",
-]
-
-[[package]]
-name = "trust-dns-resolver"
-version = "0.23.2"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "10a3e6c3aff1718b3c73e395d1f35202ba2ffa847c6a62eea0db8fb4cfe30be6"
-dependencies = [
- "cfg-if",
- "futures-util",
- "ipconfig",
- "lru-cache",
- "once_cell",
- "parking_lot",
- "rand",
- "resolv-conf",
- "serde",
- "smallvec",
- "thiserror",
- "tokio",
- "tracing",
- "trust-dns-proto",
-]
-
-[[package]]
-name = "trust-dns-server"
-version = "0.23.2"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "c540f73c2b2ec2f6c54eabd0900e7aafb747a820224b742f556e8faabb461bc7"
-dependencies = [
- "async-trait",
- "bytes",
- "cfg-if",
- "drain",
- "enum-as-inner",
- "futures-executor",
- "futures-util",
- "serde",
- "thiserror",
- "time",
- "tokio",
- "toml 0.7.8",
- "tracing",
- "trust-dns-proto",
-]
-
 [[package]]
 name = "try-lock"
 version = "0.2.5"
@@ -7851,9 +7927,9 @@ dependencies = [
 
 [[package]]
 name = "v8"
-version = "0.106.0"
+version = "130.0.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "a381badc47c6f15acb5fe0b5b40234162349ed9d4e4fd7c83a7f5547c0fc69c5"
+checksum = "c23b5c2caff00209b03a716609b275acae94b02dd3b63c4648e7232a84a8402f"
 dependencies = [
  "bindgen",
  "bitflags 2.6.0",
@@ -7874,7 +7950,7 @@ checksum = "97599c400fc79925922b58303e98fcb8fa88f573379a08ddb652e72cbd2e70f6"
 dependencies = [
  "bitflags 2.6.0",
  "encoding_rs",
- "indexmap",
+ "indexmap 2.3.0",
  "num-bigint",
  "serde",
  "thiserror",
@@ -8083,7 +8159,7 @@ dependencies = [
  "cfg_aliases",
  "codespan-reporting",
  "document-features",
- "indexmap",
+ "indexmap 2.3.0",
  "log",
  "naga",
  "once_cell",
@@ -8122,7 +8198,7 @@ dependencies = [
  "js-sys",
  "khronos-egl",
  "libc",
- "libloading 0.8.3",
+ "libloading 0.8.5",
  "log",
  "metal",
  "naga",
@@ -8387,15 +8463,6 @@ version = "0.52.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "32b752e52a2da0ddfbdbcc6fceadfeede4c939ed16d13e648833a61dfb611ed8"
 
-[[package]]
-name = "winnow"
-version = "0.5.40"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "f593a95398737aeed53e489c785df13f3618e41dbcd6718c6addbf1395aa6876"
-dependencies = [
- "memchr",
-]
-
 [[package]]
 name = "winnow"
 version = "0.6.15"
@@ -8431,7 +8498,7 @@ version = "0.1.12"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "b68db261ef59e9e52806f688020631e987592bd83619edccda9c47d42cde4f6c"
 dependencies = [
- "toml 0.5.11",
+ "toml",
 ]
 
 [[package]]
@@ -8508,7 +8575,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "2a6a39b6b5ba0d02c910d05d7fbc366a4befb8901ea107dcde9c1c97acb8a366"
 dependencies = [
  "rowan",
- "winnow 0.6.15",
+ "winnow",
 ]
 
 [[package]]
@@ -8605,9 +8672,9 @@ dependencies = [
 
 [[package]]
 name = "zeromq"
-version = "0.4.0"
+version = "0.4.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "fb0560d00172817b7f7c2265060783519c475702ae290b154115ca75e976d4d0"
+checksum = "6a4528179201f6eecf211961a7d3276faa61554c82651ecc66387f68fc3004bd"
 dependencies = [
  "async-trait",
  "asynchronous-codec",
@@ -8641,7 +8708,7 @@ dependencies = [
  "crossbeam-utils",
  "displaydoc",
  "flate2",
- "indexmap",
+ "indexmap 2.3.0",
  "memchr",
  "thiserror",
 ]
diff --git a/Cargo.toml b/Cargo.toml
index 81cbf8b4c6..4a78e7e466 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -5,7 +5,6 @@ resolver = "2"
 members = [
   "bench_util",
   "cli",
-  "cli/napi/sym",
   "ext/broadcast_channel",
   "ext/cache",
   "ext/canvas",
@@ -19,15 +18,17 @@ members = [
   "ext/io",
   "ext/kv",
   "ext/napi",
+  "ext/napi/sym",
   "ext/net",
   "ext/node",
-  "ext/node_resolver",
   "ext/url",
   "ext/web",
   "ext/webgpu",
   "ext/webidl",
   "ext/websocket",
   "ext/webstorage",
+  "resolvers/deno",
+  "resolvers/node",
   "runtime",
   "runtime/permissions",
   "tests",
@@ -44,48 +45,54 @@ license = "MIT"
 repository = "https://github.com/denoland/deno"
 
 [workspace.dependencies]
-deno_ast = { version = "=0.42.0", features = ["transpiling"] }
-deno_core = { version = "0.311.0" }
+deno_ast = { version = "=0.43.3", features = ["transpiling"] }
+deno_core = { version = "0.319.0" }
 
-deno_bench_util = { version = "0.162.0", path = "./bench_util" }
+deno_bench_util = { version = "0.171.0", path = "./bench_util" }
+deno_config = { version = "=0.38.2", features = ["workspace", "sync"] }
 deno_lockfile = "=0.23.1"
-deno_media_type = { version = "0.1.4", features = ["module_specifier"] }
-deno_permissions = { version = "0.28.0", path = "./runtime/permissions" }
-deno_runtime = { version = "0.177.0", path = "./runtime" }
-deno_semver = "=0.5.13"
+deno_media_type = { version = "0.2.0", features = ["module_specifier"] }
+deno_npm = "=0.25.4"
+deno_path_util = "=0.2.1"
+deno_permissions = { version = "0.37.0", path = "./runtime/permissions" }
+deno_runtime = { version = "0.186.0", path = "./runtime" }
+deno_semver = "=0.5.16"
 deno_terminal = "0.2.0"
-napi_sym = { version = "0.98.0", path = "./cli/napi/sym" }
+napi_sym = { version = "0.107.0", path = "./ext/napi/sym" }
 test_util = { package = "test_server", path = "./tests/util/server" }
 
-denokv_proto = "0.8.1"
-denokv_remote = "0.8.1"
+denokv_proto = "0.8.4"
+denokv_remote = "0.8.4"
 # denokv_sqlite brings in bundled sqlite if we don't disable the default features
-denokv_sqlite = { default-features = false, version = "0.8.2" }
+denokv_sqlite = { default-features = false, version = "0.8.4" }
 
 # exts
-deno_broadcast_channel = { version = "0.162.0", path = "./ext/broadcast_channel" }
-deno_cache = { version = "0.100.0", path = "./ext/cache" }
-deno_canvas = { version = "0.37.0", path = "./ext/canvas" }
-deno_console = { version = "0.168.0", path = "./ext/console" }
-deno_cron = { version = "0.48.0", path = "./ext/cron" }
-deno_crypto = { version = "0.182.0", path = "./ext/crypto" }
-deno_fetch = { version = "0.192.0", path = "./ext/fetch" }
-deno_ffi = { version = "0.155.0", path = "./ext/ffi" }
-deno_fs = { version = "0.78.0", path = "./ext/fs" }
-deno_http = { version = "0.166.0", path = "./ext/http" }
-deno_io = { version = "0.78.0", path = "./ext/io" }
-deno_kv = { version = "0.76.0", path = "./ext/kv" }
-deno_napi = { version = "0.99.0", path = "./ext/napi" }
-deno_net = { version = "0.160.0", path = "./ext/net" }
-deno_node = { version = "0.105.0", path = "./ext/node" }
-deno_tls = { version = "0.155.0", path = "./ext/tls" }
-deno_url = { version = "0.168.0", path = "./ext/url" }
-deno_web = { version = "0.199.0", path = "./ext/web" }
-deno_webgpu = { version = "0.135.0", path = "./ext/webgpu" }
-deno_webidl = { version = "0.168.0", path = "./ext/webidl" }
-deno_websocket = { version = "0.173.0", path = "./ext/websocket" }
-deno_webstorage = { version = "0.163.0", path = "./ext/webstorage" }
-node_resolver = { version = "0.7.0", path = "./ext/node_resolver" }
+deno_broadcast_channel = { version = "0.171.0", path = "./ext/broadcast_channel" }
+deno_cache = { version = "0.109.0", path = "./ext/cache" }
+deno_canvas = { version = "0.46.0", path = "./ext/canvas" }
+deno_console = { version = "0.177.0", path = "./ext/console" }
+deno_cron = { version = "0.57.0", path = "./ext/cron" }
+deno_crypto = { version = "0.191.0", path = "./ext/crypto" }
+deno_fetch = { version = "0.201.0", path = "./ext/fetch" }
+deno_ffi = { version = "0.164.0", path = "./ext/ffi" }
+deno_fs = { version = "0.87.0", path = "./ext/fs" }
+deno_http = { version = "0.175.0", path = "./ext/http" }
+deno_io = { version = "0.87.0", path = "./ext/io" }
+deno_kv = { version = "0.85.0", path = "./ext/kv" }
+deno_napi = { version = "0.108.0", path = "./ext/napi" }
+deno_net = { version = "0.169.0", path = "./ext/net" }
+deno_node = { version = "0.114.0", path = "./ext/node" }
+deno_tls = { version = "0.164.0", path = "./ext/tls" }
+deno_url = { version = "0.177.0", path = "./ext/url" }
+deno_web = { version = "0.208.0", path = "./ext/web" }
+deno_webgpu = { version = "0.144.0", path = "./ext/webgpu" }
+deno_webidl = { version = "0.177.0", path = "./ext/webidl" }
+deno_websocket = { version = "0.182.0", path = "./ext/websocket" }
+deno_webstorage = { version = "0.172.0", path = "./ext/webstorage" }
+
+# resolvers
+deno_resolver = { version = "0.9.0", path = "./resolvers/deno" }
+node_resolver = { version = "0.16.0", path = "./resolvers/node" }
 
 aes = "=0.8.3"
 anyhow = "1.0.57"
@@ -100,11 +107,13 @@ cbc = { version = "=0.1.2", features = ["alloc"] }
 # Note: Do not use the "clock" feature of chrono, as it links us to CoreFoundation on macOS.
 #       Instead use util::time::utc_now()
 chrono = { version = "0.4", default-features = false, features = ["std", "serde"] }
+color-print = "0.3.5"
 console_static_text = "=0.8.1"
+dashmap = "5.5.3"
 data-encoding = "2.3.3"
 data-url = "=0.3.0"
-deno_cache_dir = "=0.11.1"
-deno_package_json = { version = "=0.1.1", default-features = false }
+deno_cache_dir = "=0.13.2"
+deno_package_json = { version = "0.1.2", default-features = false }
 dlopen2 = "0.6.1"
 ecb = "=0.1.2"
 elliptic-curve = { version = "0.13.4", features = ["alloc", "arithmetic", "ecdh", "std", "pem", "jwk"] }
@@ -129,11 +138,11 @@ hyper-util = { version = "=0.1.7", features = ["tokio", "client", "client-legacy
 hyper_v014 = { package = "hyper", version = "0.14.26", features = ["runtime", "http1"] }
 indexmap = { version = "2", features = ["serde"] }
 ipnet = "2.3"
-jsonc-parser = { version = "=0.23.0", features = ["serde"] }
+jsonc-parser = { version = "=0.26.2", features = ["serde"] }
 lazy-regex = "3"
 libc = "0.2.126"
-libz-sys = { version = "1.1", default-features = false }
-log = "0.4.20"
+libz-sys = { version = "1.1.20", default-features = false }
+log = { version = "0.4.20", features = ["kv"] }
 lsp-types = "=0.97.0" # used by tower-lsp and "proposed" feature is unstable in patch releases
 memmem = "0.1.1"
 monch = "=0.5.0"
@@ -149,8 +158,8 @@ percent-encoding = "2.3.0"
 phf = { version = "0.11", features = ["macros"] }
 pin-project = "1.0.11" # don't pin because they yank crates from cargo
 pretty_assertions = "=1.4.0"
-prost = "0.11"
-prost-build = "0.11"
+prost = "0.13"
+prost-build = "0.13"
 rand = "=0.8.5"
 regex = "^1.7.0"
 reqwest = { version = "=0.12.5", default-features = false, features = ["rustls-tls", "stream", "gzip", "brotli", "socks", "json", "http2"] } # pinned because of https://github.com/seanmonstar/reqwest/pull/1955
@@ -179,7 +188,7 @@ tar = "=0.4.40"
 tempfile = "3.4.0"
 termcolor = "1.1.3"
 thiserror = "1.0.61"
-tokio = { version = "=1.36.0", features = ["full"] }
+tokio = { version = "1.36.0", features = ["full"] }
 tokio-metrics = { version = "0.3.0", features = ["rt"] }
 tokio-rustls = { version = "0.26.0", default-features = false, features = ["ring", "tls12"] }
 tokio-socks = "0.5.1"
@@ -196,9 +205,15 @@ webpki-root-certs = "0.26.5"
 webpki-roots = "0.26"
 which = "4.2.5"
 yoke = { version = "0.7.4", features = ["derive"] }
-zeromq = { version = "=0.4.0", default-features = false, features = ["tcp-transport", "tokio-runtime"] }
+zeromq = { version = "=0.4.1", default-features = false, features = ["tcp-transport", "tokio-runtime"] }
 zstd = "=0.12.4"
 
+opentelemetry = "0.27.0"
+opentelemetry-http = "0.27.0"
+opentelemetry-otlp = { version = "0.27.0", features = ["logs", "http-proto", "http-json"] }
+opentelemetry-semantic-conventions = { version = "0.27.0", features = ["semconv_experimental"] }
+opentelemetry_sdk = "0.27.0"
+
 # crypto
 hkdf = "0.12.3"
 rsa = { version = "0.9.3", default-features = false, features = ["std", "pem", "hazmat"] } # hazmat needed for PrehashSigner in ext/node
@@ -213,15 +228,14 @@ quote = "1"
 syn = { version = "2", features = ["full", "extra-traits"] }
 
 # unix
-nix = "=0.26.2"
+nix = "=0.27.1"
 
 # windows deps
 junction = "=0.2.0"
 winapi = "=0.3.9"
-windows-sys = { version = "0.52.0", features = ["Win32_Foundation", "Win32_Media", "Win32_Storage_FileSystem", "Win32_System_IO", "Win32_System_WindowsProgramming", "Wdk", "Wdk_System", "Wdk_System_SystemInformation", "Win32_System_Pipes", "Wdk_Storage_FileSystem", "Win32_System_Registry"] }
+windows-sys = { version = "0.52.0", features = ["Win32_Foundation", "Win32_Media", "Win32_Storage_FileSystem", "Win32_System_IO", "Win32_System_WindowsProgramming", "Wdk", "Wdk_System", "Wdk_System_SystemInformation", "Win32_Security", "Win32_System_Pipes", "Wdk_Storage_FileSystem", "Win32_System_Registry", "Win32_System_Kernel"] }
 winres = "=0.1.12"
 
-# NB: the `bench` and `release` profiles must remain EXACTLY the same.
 [profile.release]
 codegen-units = 1
 incremental = true
@@ -239,13 +253,6 @@ inherits = "release"
 codegen-units = 128
 lto = "thin"
 
-# NB: the `bench` and `release` profiles must remain EXACTLY the same.
-[profile.bench]
-codegen-units = 1
-incremental = true
-lto = true
-opt-level = 'z' # Optimize for size
-
 # Key generation is too slow on `debug`
 [profile.dev.package.num-bigint-dig]
 opt-level = 3
@@ -254,80 +261,6 @@ opt-level = 3
 [profile.dev.package.v8]
 opt-level = 1
 
-# Optimize these packages for performance.
-# NB: the `bench` and `release` profiles must remain EXACTLY the same.
-[profile.bench.package.async-compression]
-opt-level = 3
-[profile.bench.package.base64-simd]
-opt-level = 3
-[profile.bench.package.brotli]
-opt-level = 3
-[profile.bench.package.brotli-decompressor]
-opt-level = 3
-[profile.bench.package.bytes]
-opt-level = 3
-[profile.bench.package.deno_bench_util]
-opt-level = 3
-[profile.bench.package.deno_broadcast_channel]
-opt-level = 3
-[profile.bench.package.deno_core]
-opt-level = 3
-[profile.bench.package.deno_crypto]
-opt-level = 3
-[profile.bench.package.deno_fetch]
-opt-level = 3
-[profile.bench.package.deno_ffi]
-opt-level = 3
-[profile.bench.package.deno_http]
-opt-level = 3
-[profile.bench.package.deno_napi]
-opt-level = 3
-[profile.bench.package.deno_net]
-opt-level = 3
-[profile.bench.package.deno_node]
-opt-level = 3
-[profile.bench.package.deno_runtime]
-opt-level = 3
-[profile.bench.package.deno_tls]
-opt-level = 3
-[profile.bench.package.deno_url]
-opt-level = 3
-[profile.bench.package.deno_web]
-opt-level = 3
-[profile.bench.package.deno_websocket]
-opt-level = 3
-[profile.bench.package.fastwebsockets]
-opt-level = 3
-[profile.bench.package.flate2]
-opt-level = 3
-[profile.bench.package.futures-util]
-opt-level = 3
-[profile.bench.package.hyper]
-opt-level = 3
-[profile.bench.package.miniz_oxide]
-opt-level = 3
-[profile.bench.package.num-bigint-dig]
-opt-level = 3
-[profile.bench.package.rand]
-opt-level = 3
-[profile.bench.package.serde]
-opt-level = 3
-[profile.bench.package.serde_v8]
-opt-level = 3
-[profile.bench.package.test_napi]
-opt-level = 3
-[profile.bench.package.tokio]
-opt-level = 3
-[profile.bench.package.url]
-opt-level = 3
-[profile.bench.package.v8]
-opt-level = 3
-[profile.bench.package.zstd]
-opt-level = 3
-[profile.bench.package.zstd-sys]
-opt-level = 3
-
-# NB: the `bench` and `release` profiles must remain EXACTLY the same.
 [profile.release.package.async-compression]
 opt-level = 3
 [profile.release.package.base64-simd]
@@ -386,6 +319,8 @@ opt-level = 3
 opt-level = 3
 [profile.release.package.serde_v8]
 opt-level = 3
+[profile.release.package.libsui]
+opt-level = 3
 [profile.release.package.test_napi]
 opt-level = 3
 [profile.release.package.tokio]
diff --git a/README.md b/README.md
index 102319f4f2..19d4fa8a12 100644
--- a/README.md
+++ b/README.md
@@ -46,6 +46,12 @@ brew install deno
 choco install deno
 ```
 
+[WinGet](https://winstall.app/apps/DenoLand.Deno) (Windows):
+
+```powershell
+winget install --id=DenoLand.Deno
+```
+
 ### Build and install from source
 
 Complete instructions for building Deno from source can be found in the manual
diff --git a/Releases.md b/Releases.md
index a6e4d84e7b..5ce25815bd 100644
--- a/Releases.md
+++ b/Releases.md
@@ -6,6 +6,538 @@ https://github.com/denoland/deno/releases
 We also have one-line install commands at:
 https://github.com/denoland/deno_install
 
+### 2.0.6 / 2024.11.10
+
+- feat(ext/http): abort event when request is cancelled (#26781)
+- feat(ext/http): abort signal when request is cancelled (#26761)
+- feat(lsp): auto-import completions from byonm dependencies (#26680)
+- fix(ext/cache): don't panic when creating cache (#26780)
+- fix(ext/node): better inspector support (#26471)
+- fix(fmt): don't use self-closing tags in HTML (#26754)
+- fix(install): cache jsr deps from all workspace config files (#26779)
+- fix(node:zlib): gzip & gzipSync should accept ArrayBuffer (#26762)
+- fix: performance.timeOrigin (#26787)
+
+### 2.0.5 / 2024.11.05
+
+- fix(add): better error message when adding package that only has pre-release
+  versions (#26724)
+- fix(add): only add npm deps to package.json if it's at least as close as
+  deno.json (#26683)
+- fix(cli): set `npm_config_user_agent` when running npm packages or tasks
+  (#26639)
+- fix(coverage): exclude comment lines from coverage reports (#25939)
+- fix(ext/node): add `findSourceMap` to the default export of `node:module`
+  (#26720)
+- fix(ext/node): convert errors from `fs.readFile/fs.readFileSync` to node
+  format (#26632)
+- fix(ext/node): resolve exports even if parent module filename isn't present
+  (#26553)
+- fix(ext/node): return `this` from `http.Server.ref/unref()` (#26647)
+- fix(fmt): do not panic for jsx ignore container followed by jsx text (#26723)
+- fix(fmt): fix several HTML and components issues (#26654)
+- fix(fmt): ignore file directive for YAML files (#26717)
+- fix(install): handle invalid function error, and fallback to junctions
+  regardless of the error (#26730)
+- fix(lsp): include unstable features from editor settings (#26655)
+- fix(lsp): scope attribution for lazily loaded assets (#26699)
+- fix(node): Implement `os.userInfo` properly, add missing `toPrimitive`
+  (#24702)
+- fix(serve): support serve hmr (#26078)
+- fix(types): missing `import` permission on `PermissionOptionsObject` (#26627)
+- fix(workspace): support wildcard packages (#26568)
+- fix: clamp smi in fast calls by default (#26506)
+- fix: improved support for cjs and cts modules (#26558)
+- fix: op_run_microtasks crash (#26718)
+- fix: panic_hook hangs without procfs (#26732)
+- fix: remove permission check in op_require_node_module_paths (#26645)
+- fix: surface package.json location on dep parse failure (#26665)
+- perf(lsp): don't walk coverage directory (#26715)
+
+### 2.0.4 / 2024.10.29
+
+- Revert "fix(ext/node): fix dns.lookup result ordering (#26264)" (#26621)
+- Revert "fix(ext/node): use primordials in `ext/node/polyfills/https.ts`
+  (#26323)" (#26613)
+- feat(lsp): "typescript.preferences.preferTypeOnlyAutoImports" setting (#26546)
+- fix(check): expose more globals from @types/node (#26603)
+- fix(check): ignore resolving `jsxImportSource` when jsx is not used in graph
+  (#26548)
+- fix(cli): Make --watcher CLEAR_SCREEN clear scrollback buffer as well as
+  visible screen (#25997)
+- fix(compile): regression handling redirects (#26586)
+- fix(ext/napi): export dynamic symbols list for {Free,Open}BSD (#26605)
+- fix(ext/node): add path to `fs.stat` and `fs.statSync` error (#26037)
+- fix(ext/node): compatibility with {Free,Open}BSD (#26604)
+- fix(ext/node): use primordials in
+  ext\node\polyfills\internal\crypto\_randomInt.ts (#26534)
+- fix(install): cache json exports of JSR packages (#26552)
+- fix(install): regression - do not panic when config file contains \r\n
+  newlines (#26547)
+- fix(lsp): make missing import action fix infallible (#26539)
+- fix(npm): match npm bearer token generation (#26544)
+- fix(upgrade): stop running `deno lsp` processes on windows before attempting
+  to replace executable (#26542)
+- fix(watch): don't panic on invalid file specifiers (#26577)
+- fix: do not panic when failing to write to http cache (#26591)
+- fix: provide hints in terminal errors for Node.js globals (#26610)
+- fix: report exceptions from nextTick (#26579)
+- fix: support watch flag to enable watching other files than the main module on
+  serve subcommand (#26622)
+- perf: pass transpiled module to deno_core as known string (#26555)
+
+### 2.0.3 / 2024.10.25
+
+- feat(lsp): interactive inlay hints (#26382)
+- fix: support node-api in denort (#26389)
+- fix(check): support `--frozen` on deno check (#26479)
+- fix(cli): increase size of blocking task threadpool on windows (#26465)
+- fix(config): schemas for lint rule and tag autocompletion (#26515)
+- fix(ext/console): ignore casing for named colors in css parsing (#26466)
+- fix(ext/ffi): return u64/i64 as bigints from nonblocking ffi calls (#26486)
+- fix(ext/node): cancel pending ipc writes on channel close (#26504)
+- fix(ext/node): map `ERROR_INVALID_NAME` to `ENOENT` on windows (#26475)
+- fix(ext/node): only set our end of child process pipe to nonblocking mode
+  (#26495)
+- fix(ext/node): properly map reparse point error in readlink (#26375)
+- fix(ext/node): refactor http.ServerResponse into function class (#26210)
+- fix(ext/node): stub HTTPParser internal binding (#26401)
+- fix(ext/node): use primordials in `ext/node/polyfills/https.ts` (#26323)
+- fix(fmt): --ext flag requires to pass files (#26525)
+- fix(fmt): upgrade formatters (#26469)
+- fix(help): missing package specifier (#26380)
+- fix(info): resolve workspace member mappings (#26350)
+- fix(install): better json editing (#26450)
+- fix(install): cache all exports of JSR packages listed in `deno.json` (#26501)
+- fix(install): cache type only module deps in `deno install` (#26497)
+- fix(install): don't cache json exports of JSR packages (for now) (#26530)
+- fix(install): update lockfile when using package.json (#26458)
+- fix(lsp): import-map-remap quickfix for type imports (#26454)
+- fix(node/util): support array formats in `styleText` (#26507)
+- fix(node:tls): set TLSSocket.alpnProtocol for client connections (#26476)
+- fix(npm): ensure scoped package name is encoded in URLs (#26390)
+- fix(npm): support version ranges with && or comma (#26453)
+- fix: `.npmrc` settings not being passed to install/add command (#26473)
+- fix: add 'fmt-component' to unstable features in schema file (#26526)
+- fix: share inotify fd across watchers (#26200)
+- fix: unpin tokio version (#26457)
+- perf(compile): pass module source data from binary directly to v8 (#26494)
+- perf: avoid multiple calls to runMicrotask (#26378)
+
+### 2.0.2 / 2024.10.17
+
+- fix(cli): set napi object property properly (#26344)
+- fix(ext/node): add null check for kStreamBaseField (#26368)
+- fix(install): don't attempt to cache specifiers that point to directories
+  (#26369)
+- fix(jupyter): fix panics for overslow subtraction (#26371)
+- fix(jupyter): update to the new logo (#26353)
+- fix(net): don't try to set nodelay on upgrade streams (#26342)
+- fix(node/fs): copyFile with `COPYFILE_EXCL` should not throw if the
+  destination doesn't exist (#26360)
+- fix(node/http): normalize header names in `ServerResponse` (#26339)
+- fix(runtime): send ws ping frames from inspector server (#26352)
+- fix: don't warn on ignored signals on windows (#26332)
+
+### 2.0.1 / 2024.10.16
+
+- feat(lsp): "deno/didRefreshDenoConfigurationTree" notifications (#26215)
+- feat(unstable): `--unstable-detect-cjs` for respecting explicit
+  `"type": "commonjs"` (#26149)
+- fix(add): create deno.json when running `deno add jsr:<pkg>` (#26275)
+- fix(add): exact version should not have range `^` specifier (#26302)
+- fix(child_process): map node `--no-warnings` flag to `--quiet` (#26288)
+- fix(cli): add prefix to install commands in help (#26318)
+- fix(cli): consolidate pkg parser for install & remove (#26298)
+- fix(cli): named export takes precedence over default export in doc testing
+  (#26112)
+- fix(cli): improve deno info output for npm packages (#25906)
+- fix(console/ext/repl): support using parseFloat() (#25900)
+- fix(ext/console): apply coloring for console.table (#26280)
+- fix(ext/napi): pass user context to napi_threadsafe_fn finalizers (#26229)
+- fix(ext/node): allow writing to tty columns (#26201)
+- fix(ext/node): compute pem length (upper bound) for key exports (#26231)
+- fix(ext/node): fix dns.lookup result ordering (#26264)
+- fix(ext/node): handle http2 server ending stream (#26235)
+- fix(ext/node): implement TCP.setNoDelay (#26263)
+- fix(ext/node): timingSafeEqual account for AB byteOffset (#26292)
+- fix(ext/node): use primordials in `ext/node/polyfills/internal/buffer.mjs`
+  (#24993)
+- fix(ext/webgpu): allow GL backend on Windows (#26206)
+- fix(install): duplicate dependencies in `package.json` (#26128)
+- fix(install): handle pkg with dep on self when pkg part of peer dep resolution
+  (#26277)
+- fix(install): retry downloads of registry info / tarballs (#26278)
+- fix(install): support installing npm package with alias (#26246)
+- fix(jupyter): copy kernels icons to the kernel directory (#26084)
+- fix(jupyter): keep running event loop when waiting for messages (#26049)
+- fix(lsp): relative completions for bare import-mapped specifiers (#26137)
+- fix(node): make `process.stdout.isTTY` writable (#26130)
+- fix(node/util): export `styleText` from `node:util` (#26194)
+- fix(npm): support `--allow-scripts` on `deno run` (and `deno add`,
+  `deno test`, etc) (#26075)
+- fix(repl): importing json files (#26053)
+- fix(repl): remove check flags (#26140)
+- fix(unstable/worker): ensure import permissions are passed (#26101)
+- fix: add hint for missing `document` global in terminal error (#26218)
+- fix: do not panic on wsl share file paths on windows (#26081)
+- fix: do not panic running remote cjs module (#26259)
+- fix: do not panic when using methods on classes and interfaces in deno doc
+  html output (#26100)
+- fix: improve suggestions and hints when using CommonJS modules (#26287)
+- fix: node-api function call should use preamble (#26297)
+- fix: panic in `prepare_stack_trace_callback` when global interceptor throws
+  (#26241)
+- fix: use syntect for deno doc html generation (#26322)
+- perf(http): avoid clone getting request method and url (#26250)
+- perf(http): cache webidl.converters lookups in ext/fetch/23_response.js
+  (#26256)
+- perf(http): make heap allocation for path conditional (#26289)
+- perf: use fast calls for microtask ops (#26236)
+
+### 2.0.0 / 2024.10.09
+
+Read announcement blog post at: https://deno.com/blog/v2
+
+- BREAKING: `DENO_FUTURE=1` by default, or welcome to Deno 2.0 (#25213)
+- BREAKING: disallow `new Deno.FsFile()` (#25478)
+- BREAKING: drop support for Deno.run.{clearEnv,gid,uid} (#25371)
+- BREAKING: improve types for `Deno.serve` (#25369)
+- BREAKING: improved error code accuracy (#25383)
+- BREAKING: make supported compilerOptions an allow list (#25432)
+- BREAKING: move `width` and `height` options to `UnsafeWindowSurface`
+  constructor (#24200)
+- BREAKING: remove --allow-hrtime (#25367)
+- BREAKING: remove "emit" and "map" from deno info output (#25468)
+- BREAKING: remove `--allow-none` flag (#25337)
+- BREAKING: remove `--jobs` flag (#25336)
+- BREAKING: remove `--trace-ops` (#25344)
+- BREAKING: remove `--ts` flag (#25338)
+- BREAKING: remove `--unstable` flag (#25522)
+- BREAKING: remove `deno bundle` (#25339)
+- BREAKING: remove `deno vendor` (#25343)
+- BREAKING: remove `Deno.[Tls]Listener.prototype.rid` (#25556)
+- BREAKING: remove `Deno.{Conn,TlsConn,TcpConn,UnixConn}.prototype.rid` (#25446)
+- BREAKING: remove `Deno.{Reader,Writer}[Sync]` and `Deno.Closer` (#25524)
+- BREAKING: remove `Deno.Buffer` (#25441)
+- BREAKING: remove `Deno.close()` (#25347)
+- BREAKING: remove `Deno.ConnectTlsOptions.{certChain,certFile,privateKey}` and
+  `Deno.ListenTlsOptions.certChain,certFile,keyFile}` (#25525)
+- BREAKING: remove `Deno.copy()` (#25345)
+- BREAKING: remove `Deno.customInspect` (#25348)
+- BREAKING: remove `Deno.fdatasync[Sync]()` (#25520)
+- BREAKING: remove `Deno.File` (#25447)
+- BREAKING: remove `Deno.flock[Sync]()` (#25350)
+- BREAKING: remove `Deno.FsFile.prototype.rid` (#25499)
+- BREAKING: remove `Deno.fstat[Sync]()` (#25351)
+- BREAKING: remove `Deno.FsWatcher.prototype.rid` (#25444)
+- BREAKING: remove `Deno.fsync[Sync]()` (#25448)
+- BREAKING: remove `Deno.ftruncate[Sync]()` (#25412)
+- BREAKING: remove `Deno.funlock[Sync]()` (#25442)
+- BREAKING: remove `Deno.futime[Sync]()` (#25252)
+- BREAKING: remove `Deno.iter[Sync]()` (#25346)
+- BREAKING: remove `Deno.read[Sync]()` (#25409)
+- BREAKING: remove `Deno.readAll[Sync]()` (#25386)
+- BREAKING: remove `Deno.seek[Sync]()` (#25449)
+- BREAKING: remove `Deno.Seeker[Sync]` (#25551)
+- BREAKING: remove `Deno.shutdown()` (#25253)
+- BREAKING: remove `Deno.write[Sync]()` (#25408)
+- BREAKING: remove `Deno.writeAll[Sync]()` (#25407)
+- BREAKING: remove deprecated `UnsafeFnPointer` constructor type with untyped
+  `Deno.PointerObject` parameter (#25577)
+- BREAKING: remove deprecated files config (#25535)
+- BREAKING: Remove obsoleted Temporal APIs part 2 (#25505)
+- BREAKING: remove remaining web types for compatibility (#25334)
+- BREAKING: remove support for remote import maps in deno.json (#25836)
+- BREAKING: rename "deps" remote cache folder to "remote" (#25969)
+- BREAKING: soft-remove `Deno.isatty()` (#25410)
+- BREAKING: soft-remove `Deno.run()` (#25403)
+- BREAKING: soft-remove `Deno.serveHttp()` (#25451)
+- BREAKING: undeprecate `Deno.FsWatcher.prototype.return()` (#25623)
+- feat: add `--allow-import` flag (#25469)
+- feat: Add a hint on error about 'Relative import path ... not prefixed with
+  ...' (#25430)
+- feat: Add better error messages for unstable APIs (#25519)
+- feat: Add suggestion for packages using Node-API addons (#25975)
+- feat: Allow importing .cjs files (#25426)
+- feat: default to TS for file extension and support ext flag in more scenarios
+  (#25472)
+- feat: deprecate import assertions (#25281)
+- feat: Don't warn about --allow-script when using esbuild (#25894)
+- feat: hide several --unstable-* flags (#25378)
+- feat: improve lockfile v4 to store normalized version constraints and be more
+  terse (#25247)
+- feat: improve warnings for deprecations and lifecycle script for npm packages
+  (#25694)
+- feat: include version number in all --json based outputs (#25335)
+- feat: lockfile v4 by default (#25165)
+- feat: make 'globalThis.location' a configurable property (#25812)
+- feat: print `Listening on` messages on stderr instead of stdout (#25491)
+- feat: remove `--lock-write` flag (#25214)
+- feat: require jsr prefix for `deno install` and `deno add` (#25698)
+- feat: require(esm) (#25501)
+- feat: Show hints when using `window` global (#25805)
+- feat: stabilize `Deno.createHttpClient()` (#25569)
+- feat: suggest `deno install --entrypoint` instead of `deno cache` (#25228)
+- feat: support DENO_LOG env var instead of RUST_LOG (#25356)
+- feat: TypeScript 5.6 and `npm:@types/node@22` (#25614)
+- feat: Update no-window lint rule (#25486)
+- feat: update warning message for --allow-run with no list (#25693)
+- feat: warn when using `--allow-run` with no allow list (#25215)
+- feat(add): Add npm packages to package.json if present (#25477)
+- feat(add): strip package subpath when adding a package (#25419)
+- feat(add/install): Flag to add dev dependency to package.json (#25495)
+- feat(byonm): support `deno run npm:<package>` when package is not in
+  package.json (#25981)
+- feat(check): turn on noImplicitOverride (#25695)
+- feat(check): turn on useUnknownInCatchVariables (#25465)
+- feat(cli): evaluate code snippets in JSDoc and markdown (#25220)
+- feat(cli): give access to `process` global everywhere (#25291)
+- feat(cli): use NotCapable error for permission errors (#25431)
+- feat(config): Node modules option for 2.0 (#25299)
+- feat(ext/crypto): import and export p521 keys (#25789)
+- feat(ext/crypto): X448 support (#26043)
+- feat(ext/kv): configurable limit params (#25174)
+- feat(ext/node): add abort helpers, process & streams fix (#25262)
+- feat(ext/node): add rootCertificates to node:tls (#25707)
+- feat(ext/node): buffer.transcode() (#25972)
+- feat(ext/node): export 'promises' symbol from 'node:timers' (#25589)
+- feat(ext/node): export missing constants from 'zlib' module (#25584)
+- feat(ext/node): export missing symbols from domain, puncode, repl, tls
+  (#25585)
+- feat(ext/node): export more symbols from streams and timers/promises (#25582)
+- feat(ext/node): expose ES modules for _ modules (#25588)
+- feat(flags): allow double commas to escape values in path based flags (#25453)
+- feat(flags): support user provided args in repl subcommand (#25605)
+- feat(fmt): better error on malfored HTML files (#25853)
+- feat(fmt): stabilize CSS, HTML and YAML formatters (#25753)
+- feat(fmt): support vto and njk extensions (#25831)
+- feat(fmt): upgrade markup_fmt (#25768)
+- feat(install): deno install with entrypoint (#25411)
+- feat(install): warn repeatedly about not-run lifecycle scripts on explicit
+  installs (#25878)
+- feat(lint): add `no-process-global` lint rule (#25709)
+- feat(lsp): add a message when someone runs 'deno lsp' manually (#26051)
+- feat(lsp): auto-import types with 'import type' (#25662)
+- feat(lsp): html/css/yaml file formatting (#25353)
+- feat(lsp): quick fix for @deno-types="npm:@types/*" (#25954)
+- feat(lsp): turn on useUnknownInCatchVariables (#25474)
+- feat(lsp): unstable setting as list (#25552)
+- feat(permissions): `Deno.mainModule` doesn't require permissions (#25667)
+- feat(permissions): allow importing from cdn.jsdelivr.net by default (#26013)
+- feat(serve): Support second parameter in deno serve (#25606)
+- feat(tools/doc): display subitems in symbol overviews where applicable
+  (#25885)
+- feat(uninstall): alias to 'deno remove' if -g flag missing (#25461)
+- feat(upgrade): better error message on failure (#25503)
+- feat(upgrade): print info links for Deno 2 RC releases (#25225)
+- feat(upgrade): support LTS release channel (#25123)
+- fix: add link to env var docs (#25557)
+- fix: add suggestion how to fix importing CJS module (#21764)
+- fix: add test ensuring als works across dynamic import (#25593)
+- fix: better error for Deno.UnsafeWindowSurface, correct HttpClient name,
+  cleanup unused code (#25833)
+- fix: cjs resolution cases (#25739)
+- fix: consistent with deno_config and treat `"experimentalDecorators"` as
+  deprecated (#25735)
+- fix: delete old Deno 1.x headers file when loading cache (#25283)
+- fix: do not panic running invalid file specifier (#25530)
+- fix: don't include extensionless files in file collection for lint & fmt by
+  default (#25721)
+- fix: don't prompt when using `Deno.permissions.request` with `--no-prompt`
+  (#25811)
+- fix: eagerly error for specifier with empty version constraint (#25944)
+- fix: enable `Win32_Security` feature in `windows-sys` (#26007)
+- fix: error on unsupported compiler options (#25714)
+- fix: error out if a valid flag is passed before a subcommand (#25830)
+- fix: fix jupyter display function type (#25326)
+- fix: Float16Array type (#25506)
+- fix: handle showing warnings while the progress bar is shown (#25187)
+- fix: Hide 'deno cache' from help output (#25960)
+- fix: invalid ipv6 hostname on `deno serve` (#25482)
+- fix: linux canonicalization checks (#24641)
+- fix: lock down allow-run permissions more (#25370)
+- fix: make some warnings more standard (#25324)
+- fix: no cmd prefix in help output go links (#25459)
+- fix: only enable byonm if workspace root has pkg json (#25379)
+- fix: panic when require(esm) (#25769)
+- fix: precompile preserve SVG camelCase attributes (#25945)
+- fix: reland async context (#25140)
+- fix: remove --allow-run warning when using deno without args or subcommand
+  (#25684)
+- fix: remove entrypoint hack for Deno 2.0 (#25332)
+- fix: remove recently added deno.json node_modules aliasing (#25542)
+- fix: remove the typo in the help message (#25962)
+- fix: removed unstable-htttp from deno help (#25216)
+- fix: replace `npm install` hint with `deno install` hint (#25244)
+- fix: trim space around DENO_AUTH_TOKENS (#25147)
+- fix: update deno_doc (#25290)
+- fix: Update deno_npm to fix `deno install` with crossws (#25837)
+- fix: update hint for `deno add <package>` (#25455)
+- fix: update malva in deno to support astro css comments (#25553)
+- fix: update nodeModulesDir config JSON schema (#25653)
+- fix: update patchver to 0.2 (#25952)
+- fix: update sui to 0.4 (#25942)
+- fix: upgrade deno_ast 0.42 (#25313)
+- fix: upgrade deno_core to 0.307.0 (#25287)
+- fix(add/install): default to "latest" tag for npm packages in
+  `deno add npm:pkg` (#25858)
+- fix(bench): Fix table column alignments and NO_COLOR=1 (#25190)
+- fix(BREAKING): make dns record types have consistent naming (#25357)
+- fix(byonm): resolve npm deps of jsr deps (#25399)
+- fix(check): ignore noImplicitOverrides in remote modules (#25854)
+- fix(check): move is cjs check from resolving to loading (#25597)
+- fix(check): properly surface dependency errors in types file of js file
+  (#25860)
+- fix(cli): `deno task` exit with status 0 (#25637)
+- fix(cli): Default to auto with --node-modules-dir flag (#25772)
+- fix(cli): handle edge cases around `export`s in doc tests and default export
+  (#25720)
+- fix(cli): Map error kind to `PermissionDenied` when symlinking fails due to
+  permissions (#25398)
+- fix(cli): Only set allow net flag for deno serve if not already allowed all
+  (#25743)
+- fix(cli): Warn on not-run lifecycle scripts with global cache (#25786)
+- fix(cli/tools): correct `deno init --serve` template behavior (#25318)
+- fix(compile): support 'deno compile' in RC and LTS releases (#25875)
+- fix(config): validate export names (#25436)
+- fix(coverage): ignore urls from doc testing (#25736)
+- fix(doc): surface graph errors as warnings (#25888)
+- fix(dts): stabilize `fetch` declaration for use with `Deno.HttpClient`
+  (#25683)
+- fix(ext/console): more precision in console.time (#25723)
+- fix(ext/console): prevent duplicate error printing when the cause is assigned
+  (#25327)
+- fix(ext/crypto): ensure EC public keys are exported uncompressed (#25766)
+- fix(ext/crypto): fix identity test for x25519 derive bits (#26011)
+- fix(ext/crypto): reject empty usages in SubtleCrypto#importKey (#25759)
+- fix(ext/crypto): support md4 digest algorithm (#25656)
+- fix(ext/crypto): throw DataError for invalid EC key import (#25181)
+- fix(ext/fetch): fix lowercase http_proxy classified as https (#25686)
+- fix(ext/fetch): percent decode userinfo when parsing proxies (#25229)
+- fix(ext/http): do not set localhost to hostname unnecessarily (#24777)
+- fix(ext/http): gracefully handle Response.error responses (#25712)
+- fix(ext/node): add `FileHandle#writeFile` (#25555)
+- fix(ext/node): add `vm.constants` (#25630)
+- fix(ext/node): Add missing `node:path` exports (#25567)
+- fix(ext/node): Add missing node:fs and node:constants exports (#25568)
+- fix(ext/node): add stubs for `node:trace_events` (#25628)
+- fix(ext/node): attach console stream properties (#25617)
+- fix(ext/node): avoid showing `UNKNOWN` error from TCP handle (#25550)
+- fix(ext/node): close upgraded socket when the underlying http connection is
+  closed (#25387)
+- fix(ext/node): delay accept() call 2 ticks in net.Server#listen (#25481)
+- fix(ext/node): don't throw error for unsupported signal binding on windows
+  (#25699)
+- fix(ext/node): emit `online` event after worker thread is initialized (#25243)
+- fix(ext/node): export `process.allowedNodeEnvironmentFlags` (#25629)
+- fix(ext/node): export JWK public key (#25239)
+- fix(ext/node): export request and response clases from `http2` module (#25592)
+- fix(ext/node): fix `Cipheriv#update(string, undefined)` (#25571)
+- fix(ext/node): fix Decipheriv when autoPadding disabled (#25598)
+- fix(ext/node): fix process.stdin.pause() (#25864)
+- fix(ext/node): Fix vm sandbox object panic (#24985)
+- fix(ext/node): http2session ready state (#25143)
+- fix(ext/node): Implement detached option in `child_process` (#25218)
+- fix(ext/node): import EC JWK keys (#25266)
+- fix(ext/node): import JWK octet key pairs (#25180)
+- fix(ext/node): import RSA JWK keys (#25267)
+- fix(ext/node): register `node:wasi` built-in (#25134)
+- fix(ext/node): remove unimplemented promiseHook stubs (#25979)
+- fix(ext/node): report freemem() on Linux in bytes (#25511)
+- fix(ext/node): Rewrite `node:v8` serialize/deserialize (#25439)
+- fix(ext/node): session close during stream setup (#25170)
+- fix(ext/node): Stream should be instance of EventEmitter (#25527)
+- fix(ext/node): stub `inspector/promises` (#25635)
+- fix(ext/node): stub `process.cpuUsage()` (#25462)
+- fix(ext/node): stub cpu_info() for OpenBSD (#25807)
+- fix(ext/node): support x509 certificates in `createPublicKey` (#25731)
+- fix(ext/node): throw when loading `cpu-features` module (#25257)
+- fix(ext/node): update aead-gcm-stream to 0.3 (#25261)
+- fix(ext/node): use primordials in `ext/node/polyfills/console.ts` (#25572)
+- fix(ext/node): use primordials in ext/node/polyfills/wasi.ts (#25608)
+- fix(ext/node): validate input lengths in `Cipheriv` and `Decipheriv` (#25570)
+- fix(ext/web): don't ignore capture in EventTarget.removeEventListener (#25788)
+- fix(ext/webgpu): allow to build on unsupported platforms (#25202)
+- fix(ext/webgpu): sync category comment (#25580)
+- fix(ext/webstorage): make `getOwnPropertyDescriptor` with symbol return
+  `undefined` (#13348)
+- fix(flags): --allow-all should conflict with lower permissions (#25909)
+- fix(flags): don't treat empty run command as task subcommand (#25708)
+- fix(flags): move some content from docs.deno.com into help output (#25951)
+- fix(flags): properly error out for urls (#25770)
+- fix(flags): require global flag for permission flags in install subcommand
+  (#25391)
+- fix(fmt): --check was broken for CSS, YAML and HTML (#25848)
+- fix(fmt): fix incorrect quotes in components (#25249)
+- fix(fmt): fix tabs in YAML (#25536)
+- fix(fmt/markdown): fix regression with multi-line footnotes and inline math
+  (#25222)
+- fix(info): error instead of panic for npm specifiers when using byonm (#25947)
+- fix(info): move "version" field to top of json output (#25890)
+- fix(inspector): Fix panic when re-entering runtime ops (#25537)
+- fix(install): compare versions directly to decide whether to create a child
+  node_modules dir for a workspace member (#26001)
+- fix(install): Make sure target node_modules exists when symlinking (#25494)
+- fix(install): recommend using `deno install -g` when using a single http url
+  (#25388)
+- fix(install): store tags associated with package in node_modules dir (#26000)
+- fix(install): surface package.json dependency errors (#26023)
+- fix(install): Use relative symlinks in deno install (#25164)
+- fix(installl): make bin entries executable even if not put in
+  `node_modules/.bin` (#25873)
+- fix(jupyter): allow unstable flags (#25483)
+- fix(lint): correctly handle old jsx in linter (#25902)
+- fix(lint): support linting jsr pkg without version field (#25230)
+- fix(lockfile): use loose deserialization for version constraints (#25660)
+- fix(lsp): encode url parts before parsing as uri (#25509)
+- fix(lsp): exclude missing import quick fixes with bad resolutions (#26025)
+- fix(lsp): panic on url_to_uri() (#25238)
+- fix(lsp): properly resolve jsxImportSource for caching (#25688)
+- fix(lsp): update diagnostics on npm install (#25352)
+- fix(napi): Don't run microtasks in napi_resolve_deferred (#25246)
+- fix(napi): Fix worker threads importing already-loaded NAPI addon (#25245)
+- fix(no-slow-types): better `override` handling (#25989)
+- fix(node): Don't error out if we fail to statically analyze CJS re-export
+  (#25748)
+- fix(node): fix worker_threads issues blocking Angular support (#26024)
+- fix(node): implement libuv APIs needed to support `npm:sqlite3` (#25893)
+- fix(node): Include "node" condition during CJS re-export analysis (#25785)
+- fix(node): Pass NPM_PROCESS_STATE to subprocesses via temp file instead of env
+  var (#25896)
+- fix(node/byonm): do not accidentally resolve bare node built-ins (#25543)
+- fix(node/cluster): improve stubs to make log4js work (#25146)
+- fix(npm): better error handling for remote npm deps (#25670)
+- fix(npm): root package has peer dependency on itself (#26022)
+- fix(permissions): disallow any `LD_` or `DYLD_` prefixed env var without full
+  --allow-run permissions (#25271)
+- fix(permissions): disallow launching subprocess with LD_PRELOAD env var
+  without full run permissions (#25221)
+- fix(publish): ensure provenance is spec compliant (#25200)
+- fix(regression): do not expose resolved path in Deno.Command permission denied
+  error (#25434)
+- fix(runtime): don't error `child.output()` on consumed stream (#25657)
+- fix(runtime): use more null proto objects again (#25040)
+- fix(runtime/web_worker): populate `SnapshotOptions` for `WebWorker` when
+  instantiated without snapshot (#25280)
+- fix(task): correct name for scoped npm package binaries (#25390)
+- fix(task): support tasks with colons in name in `deno run` (#25233)
+- fix(task): use current executable for deno even when not named deno (#26019)
+- fix(types): simplify mtls related types (#25658)
+- fix(upgrade): more informative information on invalid version (#25319)
+- fix(windows): Deno.Command - align binary resolution with linux and mac
+  (#25429)
+- fix(workspace): handle when config has members when specified via --config
+  (#25988)
+- perf: fast path for cached dyn imports (#25636)
+- perf: Use -O3 for sui in release builds (#26010)
+- perf(cache): single cache file for remote modules (#24983)
+- perf(cache): single cache file for typescript emit (#24994)
+- perf(ext/fetch): improve decompression throughput by upgrading `tower_http`
+  (#25806)
+- perf(ext/node): reduce some allocations in require (#25197)
+- perf(ext/web): optimize performance.measure() (#25774)
+
 ### 1.46.3 / 2024.09.04
 
 - feat(upgrade): print info links for Deno 2 RC releases (#25225)
diff --git a/bench_util/Cargo.toml b/bench_util/Cargo.toml
index 5a04ab5355..d6eefc3a5d 100644
--- a/bench_util/Cargo.toml
+++ b/bench_util/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_bench_util"
-version = "0.162.0"
+version = "0.171.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/cli/Cargo.toml b/cli/Cargo.toml
index f5a8624e1d..374f3dae5e 100644
--- a/cli/Cargo.toml
+++ b/cli/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno"
-version = "2.0.0-rc.7"
+version = "2.0.6"
 authors.workspace = true
 default-run = "deno"
 edition.workspace = true
@@ -38,6 +38,11 @@ path = "./bench/lsp_bench_standalone.rs"
 
 [features]
 default = ["upgrade", "__vendored_zlib_ng"]
+# A feature that enables heap profiling with dhat on Linux.
+# 1. Compile with `cargo build --profile=release-with-debug --features=dhat-heap`
+# 2. Run the executable. It will output a dhat-heap.json file.
+# 3. Open the json file in https://nnethercote.github.io/dh_view/dh_view.html
+dhat-heap = ["dhat"]
 # A feature that enables the upgrade subcommand and the background check for
 # available updates (of deno binary). This is typically disabled for (Linux)
 # distribution packages.
@@ -64,27 +69,26 @@ winres.workspace = true
 
 [dependencies]
 deno_ast = { workspace = true, features = ["bundler", "cjs", "codegen", "proposal", "react", "sourcemap", "transforms", "typescript", "view", "visit"] }
-deno_cache_dir = { workspace = true }
-deno_config = { version = "=0.35.0", features = ["workspace", "sync"] }
+deno_cache_dir.workspace = true
+deno_config.workspace = true
 deno_core = { workspace = true, features = ["include_js_files_for_snapshotting"] }
-deno_doc = { version = "0.150.0", features = ["html", "syntect"] }
-deno_graph = { version = "=0.82.3" }
-deno_lint = { version = "=0.67.0", features = ["docs"] }
+deno_doc = { version = "0.156.0", default-features = false, features = ["rust", "html", "syntect"] }
+deno_graph = { version = "=0.84.1" }
+deno_lint = { version = "=0.68.0", features = ["docs"] }
 deno_lockfile.workspace = true
-deno_npm = "=0.25.2"
+deno_npm.workspace = true
 deno_package_json.workspace = true
+deno_path_util.workspace = true
+deno_resolver.workspace = true
 deno_runtime = { workspace = true, features = ["include_js_files_for_snapshotting"] }
 deno_semver.workspace = true
-deno_task_shell = "=0.17.0"
+deno_task_shell = "=0.18.1"
 deno_terminal.workspace = true
-eszip = "=0.78.0"
-libsui = "0.3.1"
-napi_sym.workspace = true
+libsui = "0.5.0"
 node_resolver.workspace = true
 
 anstream = "0.6.14"
 async-trait.workspace = true
-base32.workspace = true
 base64.workspace = true
 bincode = "=1.3.3"
 bytes.workspace = true
@@ -93,16 +97,17 @@ chrono = { workspace = true, features = ["now"] }
 clap = { version = "=4.5.16", features = ["env", "string", "wrap_help", "error-context"] }
 clap_complete = "=4.5.24"
 clap_complete_fig = "=4.5.2"
-color-print = "0.3.5"
+color-print.workspace = true
 console_static_text.workspace = true
-dashmap = "5.5.3"
+dashmap.workspace = true
 data-encoding.workspace = true
+dhat = { version = "0.3.3", optional = true }
 dissimilar = "=1.0.4"
 dotenvy = "0.15.7"
-dprint-plugin-json = "=0.19.3"
-dprint-plugin-jupyter = "=0.1.3"
+dprint-plugin-json = "=0.19.4"
+dprint-plugin-jupyter = "=0.1.5"
 dprint-plugin-markdown = "=0.17.8"
-dprint-plugin-typescript = "=0.93.0"
+dprint-plugin-typescript = "=0.93.2"
 env_logger = "=0.10.0"
 fancy-regex = "=0.10.0"
 faster-hex.workspace = true
@@ -116,15 +121,15 @@ http-body-util.workspace = true
 hyper-util.workspace = true
 import_map = { version = "=0.20.1", features = ["ext"] }
 indexmap.workspace = true
-jsonc-parser.workspace = true
-jupyter_runtime = { package = "runtimelib", version = "=0.14.0" }
+jsonc-parser = { workspace = true, features = ["cst", "serde"] }
+jupyter_runtime = { package = "runtimelib", version = "=0.19.0", features = ["tokio-runtime"] }
 lazy-regex.workspace = true
 libc.workspace = true
 libz-sys.workspace = true
 log = { workspace = true, features = ["serde"] }
 lsp-types.workspace = true
-malva = "=0.10.1"
-markup_fmt = "=0.13.1"
+malva = "=0.11.0"
+markup_fmt = "=0.15.0"
 memmem.workspace = true
 monch.workspace = true
 notify.workspace = true
@@ -161,7 +166,6 @@ typed-arena = "=2.0.2"
 uuid = { workspace = true, features = ["serde"] }
 walkdir = "=2.3.2"
 which.workspace = true
-yoke.workspace = true
 zeromq.workspace = true
 zip = { version = "2.1.6", default-features = false, features = ["deflate-flate2"] }
 zstd.workspace = true
diff --git a/cli/args/flags.rs b/cli/args/flags.rs
index 9938a09552..720d8db3b0 100644
--- a/cli/args/flags.rs
+++ b/cli/args/flags.rs
@@ -29,13 +29,14 @@ use deno_config::glob::PathOrPatternSet;
 use deno_core::anyhow::bail;
 use deno_core::anyhow::Context;
 use deno_core::error::AnyError;
-use deno_core::normalize_path;
 use deno_core::resolve_url_or_path;
 use deno_core::url::Url;
 use deno_graph::GraphKind;
-use deno_runtime::deno_permissions::parse_sys_kind;
+use deno_path_util::normalize_path;
+use deno_path_util::url_to_file_path;
 use deno_runtime::deno_permissions::PermissionsOptions;
-use deno_runtime::fs_util::specifier_to_file_path;
+use deno_runtime::deno_permissions::SysDescriptor;
+use deno_runtime::ops::otel::OtelConfig;
 use log::debug;
 use log::Level;
 use serde::Deserialize;
@@ -575,11 +576,20 @@ fn parse_packages_allowed_scripts(s: &str) -> Result<String, AnyError> {
 pub struct UnstableConfig {
   // TODO(bartlomieju): remove in Deno 2.5
   pub legacy_flag_enabled: bool, // --unstable
-  pub bare_node_builtins: bool,  // --unstable-bare-node-builts
+  pub bare_node_builtins: bool,
   pub sloppy_imports: bool,
   pub features: Vec<String>, // --unstabe-kv --unstable-cron
 }
 
+#[derive(Clone, Debug, Eq, PartialEq, Default)]
+pub struct InternalFlags {
+  /// Used when the language server is configured with an
+  /// explicit cache option.
+  pub cache_path: Option<PathBuf>,
+  /// Only reads to the lockfile instead of writing to it.
+  pub lockfile_skip_write: bool,
+}
+
 #[derive(Clone, Debug, Eq, PartialEq, Default)]
 pub struct Flags {
   /// Vector of CLI arguments - these are user script arguments, all Deno
@@ -591,9 +601,6 @@ pub struct Flags {
   pub ca_stores: Option<Vec<String>>,
   pub ca_data: Option<CaData>,
   pub cache_blocklist: Vec<String>,
-  /// This is not exposed as an option in the CLI, it is used internally when
-  /// the language server is configured with an explicit cache option.
-  pub cache_path: Option<PathBuf>,
   pub cached_only: bool,
   pub type_check_mode: TypeCheckMode,
   pub config_flag: ConfigFlag,
@@ -602,6 +609,8 @@ pub struct Flags {
   pub enable_op_summary_metrics: bool,
   pub enable_testing_features: bool,
   pub ext: Option<String>,
+  /// Flags that aren't exposed in the CLI, but are used internally.
+  pub internal: InternalFlags,
   pub ignore: Vec<String>,
   pub import_map_path: Option<String>,
   pub env_file: Option<String>,
@@ -688,9 +697,10 @@ impl PermissionFlags {
       }
 
       let builtin_allowed_import_hosts = [
+        "jsr.io:443",
         "deno.land:443",
         "esm.sh:443",
-        "jsr.io:443",
+        "cdn.jsdelivr.net:443",
         "raw.githubusercontent.com:443",
         "gist.githubusercontent.com:443",
       ];
@@ -958,6 +968,24 @@ impl Flags {
     args
   }
 
+  pub fn otel_config(&self) -> Option<OtelConfig> {
+    if self
+      .unstable_config
+      .features
+      .contains(&String::from("otel"))
+    {
+      Some(OtelConfig {
+        runtime_name: Cow::Borrowed("deno"),
+        runtime_version: Cow::Borrowed(crate::version::DENO_VERSION_INFO.deno),
+        deterministic: std::env::var("DENO_UNSTABLE_OTEL_DETERMINISTIC")
+          .is_ok(),
+        ..Default::default()
+      })
+    } else {
+      None
+    }
+  }
+
   /// Extract the paths the config file should be discovered from.
   ///
   /// Returns `None` if the config file should not be auto-discovered.
@@ -1002,7 +1030,7 @@ impl Flags {
           if module_specifier.scheme() == "file"
             || module_specifier.scheme() == "npm"
           {
-            if let Ok(p) = specifier_to_file_path(&module_specifier) {
+            if let Ok(p) = url_to_file_path(&module_specifier) {
               Some(vec![p.parent().unwrap().to_path_buf()])
             } else {
               Some(vec![current_dir.to_path_buf()])
@@ -1168,15 +1196,14 @@ static DENO_HELP: &str = cstr!(
 
   <y>Dependency management:</>
     <g>add</>          Add dependencies
-                  <p(245)>deno add @std/assert  |  deno add npm:express</>
-    <g>install</>      Install script as an executable
-    <g>uninstall</>    Uninstall a script previously installed with deno install
+                  <p(245)>deno add jsr:@std/assert  |  deno add npm:express</>
+    <g>install</>      Installs dependencies either in the local project or globally to a bin directory
+    <g>uninstall</>    Uninstalls a dependency or an executable script in the installation root's bin directory
     <g>remove</>       Remove dependencies from the configuration file
 
   <y>Tooling:</>
     <g>bench</>        Run benchmarks
                   <p(245)>deno bench bench.ts</>
-    <g>cache</>        Cache the dependencies
     <g>check</>        Type-check the dependencies
     <g>clean</>        Remove the cache directory
     <g>compile</>      Compile the script into a self contained executable
@@ -1258,28 +1285,7 @@ pub fn flags_from_vec(args: Vec<OsString>) -> clap::error::Result<Flags> {
         .get_arguments()
         .any(|arg| arg.get_id().as_str() == "unstable")
     {
-      subcommand = subcommand
-        .mut_arg("unstable", |arg| {
-          let new_help = arg
-            .get_help()
-            .unwrap()
-            .to_string()
-            .split_once("\n")
-            .unwrap()
-            .0
-            .to_string();
-          arg.help_heading(UNSTABLE_HEADING).help(new_help)
-        })
-        .mut_args(|arg| {
-          // long_help here is being used as a metadata, see unstable args definition
-          if arg.get_help_heading() == Some(UNSTABLE_HEADING)
-            && arg.get_long_help().is_some()
-          {
-            arg.hide(false)
-          } else {
-            arg
-          }
-        });
+      subcommand = enable_unstable(subcommand);
     }
 
     help_parse(&mut flags, subcommand);
@@ -1355,7 +1361,7 @@ pub fn flags_from_vec(args: Vec<OsString>) -> clap::error::Result<Flags> {
     }
 
     match subcommand.as_str() {
-      "add" => add_parse(&mut flags, &mut m),
+      "add" => add_parse(&mut flags, &mut m)?,
       "remove" => remove_parse(&mut flags, &mut m),
       "bench" => bench_parse(&mut flags, &mut m)?,
       "bundle" => bundle_parse(&mut flags, &mut m),
@@ -1414,6 +1420,31 @@ pub fn flags_from_vec(args: Vec<OsString>) -> clap::error::Result<Flags> {
   Ok(flags)
 }
 
+fn enable_unstable(command: Command) -> Command {
+  command
+    .mut_arg("unstable", |arg| {
+      let new_help = arg
+        .get_help()
+        .unwrap()
+        .to_string()
+        .split_once("\n")
+        .unwrap()
+        .0
+        .to_string();
+      arg.help_heading(UNSTABLE_HEADING).help(new_help)
+    })
+    .mut_args(|arg| {
+      // long_help here is being used as a metadata, see unstable args definition
+      if arg.get_help_heading() == Some(UNSTABLE_HEADING)
+        && arg.get_long_help().is_some()
+      {
+        arg.hide(false)
+      } else {
+        arg
+      }
+    })
+}
+
 macro_rules! heading {
     ($($name:ident = $title:expr),+; $total:literal) => {
       $(const $name: &str = $title;)+
@@ -1516,7 +1547,7 @@ pub fn clap_root() -> Command {
   );
 
   run_args(Command::new("deno"), true)
-    .args(unstable_args(UnstableArgsConfig::ResolutionAndRuntime))
+    .with_unstable_args(UnstableArgsConfig::ResolutionAndRuntime)
     .next_line_help(false)
     .bin_name("deno")
     .styles(
@@ -1618,7 +1649,7 @@ fn command(
 ) -> Command {
   Command::new(name)
     .about(about)
-    .args(unstable_args(unstable_args_config))
+    .with_unstable_args(unstable_args_config)
 }
 
 fn help_subcommand(app: &Command) -> Command {
@@ -1646,10 +1677,10 @@ fn add_subcommand() -> Command {
     "add",
     cstr!(
       "Add dependencies to your configuration file.
-  <p(245)>deno add @std/path</>
+  <p(245)>deno add jsr:@std/path</>
 
 You can add multiple dependencies at once:
-  <p(245)>deno add @std/path @std/assert</>"
+  <p(245)>deno add jsr:@std/path jsr:@std/assert</>"
     ),
     UnstableArgsConfig::None,
   )
@@ -1663,6 +1694,7 @@ You can add multiple dependencies at once:
           .action(ArgAction::Append),
       )
       .arg(add_dev_arg())
+      .arg(allow_scripts_arg())
   })
 }
 
@@ -1705,7 +1737,7 @@ If you specify a directory instead of a file, the path is expanded to all contai
     UnstableArgsConfig::ResolutionAndRuntime,
   )
   .defer(|cmd| {
-    runtime_args(cmd, true, false)
+    runtime_args(cmd, true, false, true)
       .arg(check_arg(true))
       .arg(
         Arg::new("json")
@@ -1842,6 +1874,7 @@ Unless --reload is specified, this command will not re-download already cached d
             .required_unless_present("help")
             .value_hint(ValueHint::FilePath),
         )
+        .arg(frozen_lockfile_arg())
         .arg(allow_import_arg())
       }
     )
@@ -1852,11 +1885,15 @@ fn compile_subcommand() -> Command {
     "compile",
     cstr!("Compiles the given script into a self contained executable.
 
-  <p(245)>deno compile -A jsr:@std/http/file-server</>
+  <p(245)>deno compile --allow-read --allow-net jsr:@std/http/file-server</>
   <p(245)>deno compile --output file_server jsr:@std/http/file-server</>
 
 Any flags specified which affect runtime behavior will be applied to the resulting binary.
 
+This allows distribution of a Deno application to systems that do not have Deno installed.
+Under the hood, it bundles a slimmed down version of the Deno runtime along with your
+JavaScript or TypeScript code.
+
 Cross-compiling to different target architectures is supported using the <c>--target</> flag.
 On the first invocation with deno will download the proper binary and cache it in <c>$DENO_DIR</>.
 
@@ -1865,7 +1902,7 @@ On the first invocation with deno will download the proper binary and cache it i
     UnstableArgsConfig::ResolutionAndRuntime,
   )
   .defer(|cmd| {
-    runtime_args(cmd, true, false)
+    runtime_args(cmd, true, false, true)
       .arg(check_arg(true))
       .arg(
         Arg::new("include")
@@ -2186,7 +2223,7 @@ This command has implicit access to all permissions.
     UnstableArgsConfig::ResolutionAndRuntime,
   )
   .defer(|cmd| {
-    runtime_args(cmd, false, true)
+    runtime_args(cmd, false, true, true)
       .arg(check_arg(false))
       .arg(executable_ext_arg())
       .arg(
@@ -2223,6 +2260,9 @@ Supported file types which are behind corresponding unstable flags (see formatti
 Format stdin and write to stdout:
   <p(245)>cat file.ts | deno fmt -</>
 
+Check if the files are formatted:
+  <p(245)>deno fmt --check</>
+
 Ignore formatting code by preceding it with an ignore comment:
   <p(245)>// deno-fmt-ignore</>
 
@@ -2252,7 +2292,7 @@ Ignore formatting a file by adding an ignore comment at the top of the file:
             "sass", "less", "html", "svelte", "vue", "astro", "yml", "yaml",
             "ipynb",
           ])
-          .help_heading(FMT_HEADING),
+          .help_heading(FMT_HEADING).requires("files"),
       )
       .arg(
         Arg::new("ignore")
@@ -2373,7 +2413,7 @@ Ignore formatting a file by adding an ignore comment at the top of the file:
 }
 
 fn init_subcommand() -> Command {
-  command("init", "Initialize a new project", UnstableArgsConfig::None).defer(
+  command("init", "scaffolds a basic Deno project with a script, test, and configuration file", UnstableArgsConfig::None).defer(
     |cmd| {
       cmd
         .arg(Arg::new("dir").value_hint(ValueHint::DirPath))
@@ -2418,7 +2458,7 @@ The following information is shown:
       .arg(
         location_arg()
           .conflicts_with("file")
-          .help("Show files used for origin bound APIs like the Web Storage API when running a script with '--location=<HREF>'")
+          .help(cstr!("Show files used for origin bound APIs like the Web Storage API when running a script with <c>--location=<<HREF>></>"))
       )
       .arg(no_check_arg().hide(true)) // TODO(lucacasonato): remove for 2.0
       .arg(no_config_arg())
@@ -2449,7 +2489,7 @@ in the package cache. If no dependency is specified, installs all dependencies l
 If the <p(245)>--entrypoint</> flag is passed, installs the dependencies of the specified entrypoint(s).
 
   <p(245)>deno install</>
-  <p(245)>deno install @std/bytes</>
+  <p(245)>deno install jsr:@std/bytes</>
   <p(245)>deno install npm:chalk</>
   <p(245)>deno install --entrypoint entry1.ts entry2.ts</>
 
@@ -2460,7 +2500,7 @@ If the <bold>--global</> flag is set, installs a script as an executable in the
   <p(245)>deno install --global --allow-net --allow-read jsr:@std/http/file-server</>
   <p(245)>deno install -g https://examples.deno.land/color-logging.ts</>
 
-To change the executable name, use -n/--name:
+To change the executable name, use <c>-n</>/<c>--name</>:
   <p(245)>deno install -g --allow-net --allow-read -n serve jsr:@std/http/file-server</>
 
 The executable name is inferred by default:
@@ -2482,7 +2522,7 @@ The installation root is determined, in order of precedence:
 These must be added to the path manually if required."), UnstableArgsConfig::ResolutionAndRuntime)
     .visible_alias("i")
     .defer(|cmd| {
-      permission_args(runtime_args(cmd, false, true), Some("global"))
+      permission_args(runtime_args(cmd, false, true, false), Some("global"))
         .arg(check_arg(true))
         .arg(allow_scripts_arg())
         .arg(
@@ -2742,9 +2782,19 @@ To ignore linting on an entire file, you can add an ignore comment at the top of
 }
 
 fn repl_subcommand() -> Command {
-  command("repl", "Read Eval Print Loop", UnstableArgsConfig::ResolutionAndRuntime)
-    .defer(|cmd| runtime_args(cmd, true, true)
-      .arg(check_arg(false))
+  command("repl", cstr!(
+    "Starts a read-eval-print-loop, which lets you interactively build up program state in the global context.
+It is especially useful for quick prototyping and checking snippets of code.
+
+TypeScript is supported, however it is not type-checked, only transpiled."
+  ), UnstableArgsConfig::ResolutionAndRuntime)
+    .defer(|cmd| {
+      let cmd = compile_args_without_check_args(cmd);
+      let cmd = inspect_args(cmd);
+      let cmd = permission_args(cmd, None);
+      let cmd = runtime_misc_args(cmd);
+
+      cmd
       .arg(
         Arg::new("eval-file")
           .long("eval-file")
@@ -2763,7 +2813,7 @@ fn repl_subcommand() -> Command {
       .after_help(cstr!("<y>Environment variables:</>
   <g>DENO_REPL_HISTORY</>  Set REPL history file path. History file is disabled when the value is empty.
                        <p(245)>[default: $DENO_DIR/deno_history.txt]</>"))
-    )
+    })
     .arg(env_file_arg())
     .arg(
       Arg::new("args")
@@ -2775,7 +2825,7 @@ fn repl_subcommand() -> Command {
 }
 
 fn run_args(command: Command, top_level: bool) -> Command {
-  runtime_args(command, true, true)
+  runtime_args(command, true, true, true)
     .arg(check_arg(false))
     .arg(watch_arg(true))
     .arg(hmr_arg(true))
@@ -2825,19 +2875,17 @@ fn serve_subcommand() -> Command {
 
 The serve command uses the default exports of the main module to determine which servers to start.
 
-See https://docs.deno.com/runtime/manual/tools/serve for more detailed information.
-
 Start a server defined in server.ts:
   <p(245)>deno serve server.ts</>
 
 Start a server defined in server.ts, watching for changes and running on port 5050:
   <p(245)>deno serve --watch --port 5050 server.ts</>
 
-<y>Read more:</> <c>https://docs.deno.com/go/serve</>"), UnstableArgsConfig::ResolutionAndRuntime), true, true)
+<y>Read more:</> <c>https://docs.deno.com/go/serve</>"), UnstableArgsConfig::ResolutionAndRuntime), true, true, true)
     .arg(
       Arg::new("port")
         .long("port")
-        .help("The TCP port to serve on, defaulting to 8000. Pass 0 to pick a random free port")
+        .help(cstr!("The TCP port to serve on. Pass 0 to pick a random free port <p(245)>[default: 8000]</>"))
         .value_parser(value_parser!(u16)),
     )
     .arg(
@@ -2888,6 +2936,7 @@ List all available tasks:
           .help("Specify the directory to run the task in")
           .value_hint(ValueHint::DirPath),
       )
+      .arg(node_modules_dir_arg())
   })
 }
 
@@ -2906,7 +2955,7 @@ or <c>**/__tests__/**</>:
           UnstableArgsConfig::ResolutionAndRuntime
     )
     .defer(|cmd|
-      runtime_args(cmd, true, true)
+      runtime_args(cmd, true, true, true)
       .arg(check_arg(true))
       .arg(
         Arg::new("ignore")
@@ -3047,11 +3096,13 @@ fn parallel_arg(descr: &str) -> Arg {
 fn types_subcommand() -> Command {
   command(
     "types",
-    "Print runtime TypeScript declarations.
+    cstr!(
+      "Print runtime TypeScript declarations.
 
   <p(245)>deno types > lib.deno.d.ts</>
 
-The declaration file could be saved and used for typing information.",
+The declaration file could be saved and used for typing information."
+    ),
     UnstableArgsConfig::None,
   )
 }
@@ -3161,7 +3212,7 @@ See the Deno 1.x to 2.x Migration Guide for migration instructions: https://docs
 }
 
 fn publish_subcommand() -> Command {
-  command("publish", "Publish the current working directory's package or workspace", UnstableArgsConfig::ResolutionOnly)
+  command("publish", "Publish the current working directory's package or workspace to JSR", UnstableArgsConfig::ResolutionOnly)
     .defer(|cmd| {
       cmd
       .arg(
@@ -3238,7 +3289,7 @@ fn permission_args(app: Command, requires: Option<&'static str>) -> Command {
   <g>-W, --allow-write[=<<PATH>...]</>            Allow file system write access. Optionally specify allowed paths.
                                              <p(245)>--allow-write  |  --allow-write="/etc,/var/log.txt"</>
   <g>-I, --allow-import[=<<IP_OR_HOSTNAME>...]</> Allow importing from remote hosts. Optionally specify allowed IP addresses and host names, with ports as necessary.
-                                            Default value: <p(245)>deno.land:443,jsr.io:443,esm.sh:443,raw.githubusercontent.com:443,user.githubusercontent.com:443</>
+                                            Default value: <p(245)>deno.land:443,jsr.io:443,esm.sh:443,cdn.jsdelivr.net:443,raw.githubusercontent.com:443,user.githubusercontent.com:443</>
                                              <p(245)>--allow-import  |  --allow-import="example.com,github.com"</>
   <g>-N, --allow-net[=<<IP_OR_HOSTNAME>...]</>    Allow network access. Optionally specify allowed IP addresses and host names, with ports as necessary.
                                              <p(245)>--allow-net  |  --allow-net="localhost:8080,deno.land"</>
@@ -3258,7 +3309,7 @@ fn permission_args(app: Command, requires: Option<&'static str>) -> Command {
                                              <p(245)>--deny-net  |  --deny-net="localhost:8080,deno.land"</>
   <g>    --deny-env[=<<VARIABLE_NAME>...]</>      Deny access to environment variables. Optionally specify inacessible environment variables.
                                              <p(245)>--deny-env  |  --deny-env="PORT,HOME,PATH"</>
-  <g>-S, --deny-sys[=<<API_NAME>...]</>           Deny access to OS information. Optionally deny specific APIs by function name.
+  <g>    --deny-sys[=<<API_NAME>...]</>           Deny access to OS information. Optionally deny specific APIs by function name.
                                              <p(245)>--deny-sys  |  --deny-sys="systemMemoryInfo,osRelease"</>
       <g>--deny-run[=<<PROGRAM_NAME>...]</>       Deny running subprocesses. Optionally specify denied runnable program names.
                                              <p(245)>--deny-run  |  --deny-run="whoami,ps"</>
@@ -3355,8 +3406,7 @@ fn permission_args(app: Command, requires: Option<&'static str>) -> Command {
           .value_name("IP_OR_HOSTNAME")
           .help("Allow network access. Optionally specify allowed IP addresses and host names, with ports as necessary")
           .value_parser(flags_net::validator)
-          .hide(true)
-          ;
+          .hide(true);
         if let Some(requires) = requires {
           arg = arg.requires(requires)
         }
@@ -3448,7 +3498,7 @@ fn permission_args(app: Command, requires: Option<&'static str>) -> Command {
           .require_equals(true)
           .value_name("API_NAME")
           .help("Allow access to OS information. Optionally allow specific APIs by function name")
-          .value_parser(|key: &str| parse_sys_kind(key).map(ToString::to_string))
+          .value_parser(|key: &str| SysDescriptor::parse(key.to_string()).map(|s| s.into_string()))
           .hide(true)
           ;
         if let Some(requires) = requires {
@@ -3466,7 +3516,7 @@ fn permission_args(app: Command, requires: Option<&'static str>) -> Command {
           .require_equals(true)
           .value_name("API_NAME")
           .help("Deny access to OS information. Optionally deny specific APIs by function name")
-          .value_parser(|key: &str| parse_sys_kind(key).map(ToString::to_string))
+          .value_parser(|key: &str| SysDescriptor::parse(key.to_string()).map(|s| s.into_string()))
           .hide(true)
           ;
         if let Some(requires) = requires {
@@ -3550,8 +3600,7 @@ fn permission_args(app: Command, requires: Option<&'static str>) -> Command {
           .long("allow-hrtime")
           .action(ArgAction::SetTrue)
           .help("REMOVED in Deno 2.0")
-          .hide(true)
-          ;
+          .hide(true);
         if let Some(requires) = requires {
           arg = arg.requires(requires)
         }
@@ -3564,8 +3613,7 @@ fn permission_args(app: Command, requires: Option<&'static str>) -> Command {
           .long("deny-hrtime")
           .action(ArgAction::SetTrue)
           .help("REMOVED in Deno 2.0")
-          .hide(true)
-          ;
+          .hide(true);
         if let Some(requires) = requires {
           arg = arg.requires(requires)
         }
@@ -3619,6 +3667,7 @@ fn runtime_args(
   app: Command,
   include_perms: bool,
   include_inspector: bool,
+  include_allow_scripts: bool,
 ) -> Command {
   let app = compile_args(app);
   let app = if include_perms {
@@ -3631,6 +3680,15 @@ fn runtime_args(
   } else {
     app
   };
+  let app = if include_allow_scripts {
+    app.arg(allow_scripts_arg())
+  } else {
+    app
+  };
+  runtime_misc_args(app)
+}
+
+fn runtime_misc_args(app: Command) -> Command {
   app
     .arg(frozen_lockfile_arg())
     .arg(cached_only_arg())
@@ -3650,7 +3708,7 @@ fn allow_import_arg() -> Arg {
     .require_equals(true)
     .value_name("IP_OR_HOSTNAME")
     .help(cstr!(
-      "Allow importing from remote hosts. Optionally specify allowed IP addresses and host names, with ports as necessary. Default value: <p(245)>deno.land:443,jsr.io:443,esm.sh:443,raw.githubusercontent.com:443,user.githubusercontent.com:443</>"
+      "Allow importing from remote hosts. Optionally specify allowed IP addresses and host names, with ports as necessary. Default value: <p(245)>deno.land:443,jsr.io:443,esm.sh:443,cdn.jsdelivr.net:443,raw.githubusercontent.com:443,user.githubusercontent.com:443</>"
     ))
     .value_parser(flags_net::validator)
 }
@@ -3801,7 +3859,9 @@ fn location_arg() -> Arg {
       url.set_password(None).unwrap();
       Ok(url)
     })
-    .help("Value of 'globalThis.location' used by some web APIs")
+    .help(cstr!(
+      "Value of <p(245)>globalThis.location</> used by some web APIs"
+    ))
     .value_hint(ValueHint::Url)
 }
 
@@ -4110,23 +4170,29 @@ enum UnstableArgsConfig {
   ResolutionAndRuntime,
 }
 
-struct UnstableArgsIter {
-  idx: usize,
-  cfg: UnstableArgsConfig,
+trait CommandExt {
+  fn with_unstable_args(self, cfg: UnstableArgsConfig) -> Self;
 }
 
-impl Iterator for UnstableArgsIter {
-  type Item = Arg;
+impl CommandExt for Command {
+  fn with_unstable_args(self, cfg: UnstableArgsConfig) -> Self {
+    let mut next_display_order = {
+      let mut value = 1000;
+      move || {
+        value += 1;
+        value
+      }
+    };
 
-  fn next(&mut self) -> Option<Self::Item> {
-    let arg = if self.idx == 0 {
+    let mut cmd = self.arg(
       Arg::new("unstable")
-        .long("unstable")
-        .help(cstr!("Enable all unstable features and APIs. Instead of using this flag, consider enabling individual unstable features
+      .long("unstable")
+      .help(cstr!("Enable all unstable features and APIs. Instead of using this flag, consider enabling individual unstable features
   <p(245)>To view the list of individual unstable feature flags, run this command again with --help=unstable</>"))
-        .action(ArgAction::SetTrue)
-        .hide(matches!(self.cfg, UnstableArgsConfig::None))
-    } else if self.idx == 1 {
+      .action(ArgAction::SetTrue)
+      .hide(matches!(cfg, UnstableArgsConfig::None))
+      .display_order(next_display_order())
+    ).arg(
       Arg::new("unstable-bare-node-builtins")
         .long("unstable-bare-node-builtins")
         .help("Enable unstable bare node builtins feature")
@@ -4134,20 +4200,36 @@ impl Iterator for UnstableArgsIter {
         .value_parser(FalseyValueParser::new())
         .action(ArgAction::SetTrue)
         .hide(true)
-        .long_help(match self.cfg {
+        .long_help(match cfg {
           UnstableArgsConfig::None => None,
           UnstableArgsConfig::ResolutionOnly
           | UnstableArgsConfig::ResolutionAndRuntime => Some("true"),
         })
         .help_heading(UNSTABLE_HEADING)
-    } else if self.idx == 2 {
+        .display_order(next_display_order()),
+    ).arg(
+      Arg::new("unstable-detect-cjs")
+        .long("unstable-detect-cjs")
+        .help("Reads the package.json type field in a project to treat .js files as .cjs")
+        .value_parser(FalseyValueParser::new())
+        .action(ArgAction::SetTrue)
+        .hide(true)
+        .long_help(match cfg {
+          UnstableArgsConfig::None => None,
+          UnstableArgsConfig::ResolutionOnly
+          | UnstableArgsConfig::ResolutionAndRuntime => Some("true"),
+        })
+        .help_heading(UNSTABLE_HEADING)
+        .display_order(next_display_order())
+    ).arg(
       Arg::new("unstable-byonm")
         .long("unstable-byonm")
         .value_parser(FalseyValueParser::new())
         .action(ArgAction::SetTrue)
         .hide(true)
         .help_heading(UNSTABLE_HEADING)
-    } else if self.idx == 3 {
+        .display_order(next_display_order()),
+    ).arg(
       Arg::new("unstable-sloppy-imports")
       .long("unstable-sloppy-imports")
       .help("Enable unstable resolving of specifiers by extension probing, .js to .ts, and directory probing")
@@ -4155,40 +4237,39 @@ impl Iterator for UnstableArgsIter {
       .value_parser(FalseyValueParser::new())
       .action(ArgAction::SetTrue)
       .hide(true)
-      .long_help(match self.cfg {
+      .long_help(match cfg {
         UnstableArgsConfig::None => None,
         UnstableArgsConfig::ResolutionOnly | UnstableArgsConfig::ResolutionAndRuntime => Some("true")
       })
       .help_heading(UNSTABLE_HEADING)
-    } else if self.idx > 3 {
-      let granular_flag = crate::UNSTABLE_GRANULAR_FLAGS.get(self.idx - 4)?;
-      Arg::new(format!("unstable-{}", granular_flag.name))
-        .long(format!("unstable-{}", granular_flag.name))
-        .help(granular_flag.help_text)
-        .action(ArgAction::SetTrue)
-        .hide(true)
-        .help_heading(UNSTABLE_HEADING)
-        // we don't render long help, so using it here as a sort of metadata
-        .long_help(if granular_flag.show_in_help {
-          match self.cfg {
-            UnstableArgsConfig::None | UnstableArgsConfig::ResolutionOnly => {
-              None
-            }
-            UnstableArgsConfig::ResolutionAndRuntime => Some("true"),
-          }
-        } else {
-          None
-        })
-    } else {
-      return None;
-    };
-    self.idx += 1;
-    Some(arg.display_order(self.idx + 1000))
-  }
-}
+      .display_order(next_display_order())
+    );
 
-fn unstable_args(cfg: UnstableArgsConfig) -> impl IntoIterator<Item = Arg> {
-  UnstableArgsIter { idx: 0, cfg }
+    for granular_flag in crate::UNSTABLE_GRANULAR_FLAGS.iter() {
+      cmd = cmd.arg(
+        Arg::new(format!("unstable-{}", granular_flag.name))
+          .long(format!("unstable-{}", granular_flag.name))
+          .help(granular_flag.help_text)
+          .action(ArgAction::SetTrue)
+          .hide(true)
+          .help_heading(UNSTABLE_HEADING)
+          // we don't render long help, so using it here as a sort of metadata
+          .long_help(if granular_flag.show_in_help {
+            match cfg {
+              UnstableArgsConfig::None | UnstableArgsConfig::ResolutionOnly => {
+                None
+              }
+              UnstableArgsConfig::ResolutionAndRuntime => Some("true"),
+            }
+          } else {
+            None
+          })
+          .display_order(next_display_order()),
+      );
+    }
+
+    cmd
+  }
 }
 
 fn allow_scripts_arg_parse(
@@ -4210,8 +4291,13 @@ fn allow_scripts_arg_parse(
   Ok(())
 }
 
-fn add_parse(flags: &mut Flags, matches: &mut ArgMatches) {
+fn add_parse(
+  flags: &mut Flags,
+  matches: &mut ArgMatches,
+) -> clap::error::Result<()> {
+  allow_scripts_arg_parse(flags, matches)?;
   flags.subcommand = DenoSubcommand::Add(add_parse_inner(matches, None));
+  Ok(())
 }
 
 fn add_parse_inner(
@@ -4237,7 +4323,7 @@ fn bench_parse(
 ) -> clap::error::Result<()> {
   flags.type_check_mode = TypeCheckMode::Local;
 
-  runtime_args_parse(flags, matches, true, false)?;
+  runtime_args_parse(flags, matches, true, false, true)?;
   ext_arg_parse(flags, matches);
 
   // NOTE: `deno bench` always uses `--no-prompt`, tests shouldn't ever do
@@ -4305,6 +4391,7 @@ fn check_parse(
   flags.type_check_mode = TypeCheckMode::Local;
   compile_args_without_check_parse(flags, matches)?;
   unstable_args_parse(flags, matches, UnstableArgsConfig::ResolutionAndRuntime);
+  frozen_lockfile_arg_parse(flags, matches);
   let files = matches.remove_many::<String>("file").unwrap().collect();
   if matches.get_flag("all") || matches.get_flag("remote") {
     flags.type_check_mode = TypeCheckMode::All;
@@ -4327,7 +4414,7 @@ fn compile_parse(
   matches: &mut ArgMatches,
 ) -> clap::error::Result<()> {
   flags.type_check_mode = TypeCheckMode::Local;
-  runtime_args_parse(flags, matches, true, false)?;
+  runtime_args_parse(flags, matches, true, false, true)?;
 
   let mut script = matches.remove_many::<String>("script_arg").unwrap();
   let source_file = script.next().unwrap();
@@ -4502,7 +4589,7 @@ fn eval_parse(
   flags: &mut Flags,
   matches: &mut ArgMatches,
 ) -> clap::error::Result<()> {
-  runtime_args_parse(flags, matches, false, true)?;
+  runtime_args_parse(flags, matches, false, true, false)?;
   unstable_args_parse(flags, matches, UnstableArgsConfig::ResolutionAndRuntime);
   flags.allow_all();
 
@@ -4595,7 +4682,7 @@ fn install_parse(
   flags: &mut Flags,
   matches: &mut ArgMatches,
 ) -> clap::error::Result<()> {
-  runtime_args_parse(flags, matches, true, true)?;
+  runtime_args_parse(flags, matches, true, true, false)?;
 
   let global = matches.get_flag("global");
   if global {
@@ -4655,7 +4742,7 @@ fn json_reference_parse(
   app.build();
 
   fn serialize_command(
-    command: &mut Command,
+    mut command: Command,
     top_level: bool,
   ) -> deno_core::serde_json::Value {
     let args = command
@@ -4663,7 +4750,7 @@ fn json_reference_parse(
       .filter(|arg| {
         !arg.is_hide_set()
           && if top_level {
-            true
+            arg.is_global_set()
           } else {
             !arg.is_global_set()
           }
@@ -4672,40 +4759,49 @@ fn json_reference_parse(
         let name = arg.get_id().as_str();
         let short = arg.get_short();
         let long = arg.get_long();
-        let aliases = arg.get_visible_aliases();
         let required = arg.is_required_set();
-        let help = arg.get_help().map(|help| help.to_string());
+        let help = arg.get_help().map(|help| help.ansi().to_string());
+        let help_heading = arg
+          .get_help_heading()
+          .map(|help_heading| help_heading.to_string());
         let usage = arg.to_string();
 
         json!({
           "name": name,
           "short": short,
           "long": long,
-          "aliases": aliases,
           "required": required,
           "help": help,
+          "help_heading": help_heading,
           "usage": usage,
         })
       })
       .collect::<Vec<_>>();
 
     let name = command.get_name().to_string();
-    let about = command.get_about().map(|about| about.to_string());
-    let visible_aliases = command
-      .get_visible_aliases()
-      .map(|s| s.to_string())
-      .collect::<Vec<_>>();
-    let usage = command.render_usage().to_string();
+    let about = command.get_about().map(|about| about.ansi().to_string());
+    let usage = command.render_usage().ansi().to_string();
 
     let subcommands = command
-      .get_subcommands_mut()
-      .map(|command| serialize_command(command, false))
+      .get_subcommands()
+      .map(|command| {
+        serialize_command(
+          if command
+            .get_arguments()
+            .any(|arg| arg.get_id().as_str() == "unstable")
+          {
+            enable_unstable(command.clone())
+          } else {
+            command.clone()
+          },
+          false,
+        )
+      })
       .collect::<Vec<_>>();
 
     json!({
       "name": name,
       "about": about,
-      "visible_aliases": visible_aliases,
       "args": args,
       "subcommands": subcommands,
       "usage": usage,
@@ -4713,7 +4809,7 @@ fn json_reference_parse(
   }
 
   flags.subcommand = DenoSubcommand::JSONReference(JSONReferenceFlags {
-    json: serialize_command(&mut app, true),
+    json: serialize_command(app, true),
   })
 }
 
@@ -4812,8 +4908,18 @@ fn repl_parse(
   flags: &mut Flags,
   matches: &mut ArgMatches,
 ) -> clap::error::Result<()> {
-  runtime_args_parse(flags, matches, true, true)?;
-  unsafely_ignore_certificate_errors_parse(flags, matches);
+  unstable_args_parse(flags, matches, UnstableArgsConfig::ResolutionAndRuntime);
+  compile_args_without_check_parse(flags, matches)?;
+  cached_only_arg_parse(flags, matches);
+  frozen_lockfile_arg_parse(flags, matches);
+  permission_args_parse(flags, matches)?;
+  inspect_arg_parse(flags, matches);
+  location_arg_parse(flags, matches);
+  v8_flags_arg_parse(flags, matches);
+  seed_arg_parse(flags, matches);
+  enable_testing_features_arg_parse(flags, matches);
+  env_file_arg_parse(flags, matches);
+  strace_ops_parse(flags, matches);
 
   let eval_files = matches
     .remove_many::<String>("eval-file")
@@ -4845,7 +4951,7 @@ fn run_parse(
   mut app: Command,
   bare: bool,
 ) -> clap::error::Result<()> {
-  runtime_args_parse(flags, matches, true, true)?;
+  runtime_args_parse(flags, matches, true, true, true)?;
   ext_arg_parse(flags, matches);
 
   flags.code_cache_enabled = !matches.get_flag("no-code-cache");
@@ -4886,7 +4992,7 @@ fn serve_parse(
 
   let worker_count = parallel_arg_parse(matches).map(|v| v.get());
 
-  runtime_args_parse(flags, matches, true, true)?;
+  runtime_args_parse(flags, matches, true, true, true)?;
   // If the user didn't pass --allow-net, add this port to the network
   // allowlist. If the host is 0.0.0.0, we add :{port} and allow the same network perms
   // as if it was passed to --allow-net directly.
@@ -4941,6 +5047,7 @@ fn task_parse(flags: &mut Flags, matches: &mut ArgMatches) {
     .unwrap_or(ConfigFlag::Discover);
 
   unstable_args_parse(flags, matches, UnstableArgsConfig::ResolutionAndRuntime);
+  node_modules_arg_parse(flags, matches);
 
   let mut task_flags = TaskFlags {
     cwd: matches.remove_one::<String>("cwd"),
@@ -4980,7 +5087,7 @@ fn test_parse(
   matches: &mut ArgMatches,
 ) -> clap::error::Result<()> {
   flags.type_check_mode = TypeCheckMode::Local;
-  runtime_args_parse(flags, matches, true, true)?;
+  runtime_args_parse(flags, matches, true, true, true)?;
   ext_arg_parse(flags, matches);
 
   // NOTE: `deno test` always uses `--no-prompt`, tests shouldn't ever do
@@ -5345,6 +5452,7 @@ fn runtime_args_parse(
   matches: &mut ArgMatches,
   include_perms: bool,
   include_inspector: bool,
+  include_allow_scripts: bool,
 ) -> clap::error::Result<()> {
   unstable_args_parse(flags, matches, UnstableArgsConfig::ResolutionAndRuntime);
   compile_args_parse(flags, matches)?;
@@ -5356,6 +5464,9 @@ fn runtime_args_parse(
   if include_inspector {
     inspect_arg_parse(flags, matches);
   }
+  if include_allow_scripts {
+    allow_scripts_arg_parse(flags, matches)?;
+  }
   location_arg_parse(flags, matches);
   v8_flags_arg_parse(flags, matches);
   seed_arg_parse(flags, matches);
@@ -6707,6 +6818,32 @@ mod tests {
         ..Flags::default()
       }
     );
+
+    let r = flags_from_vec(svec!["deno", "fmt", "--ext", "html"]);
+    assert!(r.is_err());
+    let r = flags_from_vec(svec!["deno", "fmt", "--ext", "html", "./**"]);
+    assert_eq!(
+      r.unwrap(),
+      Flags {
+        subcommand: DenoSubcommand::Fmt(FmtFlags {
+          check: false,
+          files: FileFlags {
+            include: vec!["./**".to_string()],
+            ignore: vec![],
+          },
+          use_tabs: None,
+          line_width: None,
+          indent_width: None,
+          single_quote: None,
+          prose_wrap: None,
+          no_semicolons: None,
+          unstable_component: false,
+          watch: Default::default(),
+        }),
+        ext: Some("html".to_string()),
+        ..Flags::default()
+      }
+    );
   }
 
   #[test]
@@ -7355,7 +7492,7 @@ mod tests {
   #[test]
   fn repl_with_flags() {
     #[rustfmt::skip]
-    let r = flags_from_vec(svec!["deno", "repl", "-A", "--import-map", "import_map.json", "--no-remote", "--config", "tsconfig.json", "--no-check", "--reload", "--lock", "lock.json", "--cert", "example.crt", "--cached-only", "--location", "https:foo", "--v8-flags=--help", "--seed", "1", "--inspect=127.0.0.1:9229", "--unsafely-ignore-certificate-errors", "--env=.example.env"]);
+    let r = flags_from_vec(svec!["deno", "repl", "-A", "--import-map", "import_map.json", "--no-remote", "--config", "tsconfig.json", "--reload", "--lock", "lock.json", "--cert", "example.crt", "--cached-only", "--location", "https:foo", "--v8-flags=--help", "--seed", "1", "--inspect=127.0.0.1:9229", "--unsafely-ignore-certificate-errors", "--env=.example.env"]);
     assert_eq!(
       r.unwrap(),
       Flags {
@@ -7403,7 +7540,6 @@ mod tests {
           allow_write: Some(vec![]),
           ..Default::default()
         },
-        type_check_mode: TypeCheckMode::None,
         ..Flags::default()
       }
     );
@@ -7425,7 +7561,6 @@ mod tests {
           eval: None,
           is_default_command: false,
         }),
-        type_check_mode: TypeCheckMode::None,
         ..Flags::default()
       }
     );
@@ -8827,8 +8962,12 @@ mod tests {
 
   #[test]
   fn test_no_colon_in_value_name() {
-    let app =
-      runtime_args(Command::new("test_inspect_completion_value"), true, true);
+    let app = runtime_args(
+      Command::new("test_inspect_completion_value"),
+      true,
+      true,
+      false,
+    );
     let inspect_args = app
       .get_arguments()
       .filter(|arg| arg.get_id() == "inspect")
diff --git a/cli/args/flags_net.rs b/cli/args/flags_net.rs
index 88ffcf0e46..abfcf28382 100644
--- a/cli/args/flags_net.rs
+++ b/cli/args/flags_net.rs
@@ -51,7 +51,7 @@ pub fn parse(paths: Vec<String>) -> clap::error::Result<Vec<String>> {
       }
     } else {
       NetDescriptor::parse(&host_and_port).map_err(|e| {
-        clap::Error::raw(clap::error::ErrorKind::InvalidValue, format!("{e:?}"))
+        clap::Error::raw(clap::error::ErrorKind::InvalidValue, e.to_string())
       })?;
       out.push(host_and_port)
     }
diff --git a/cli/args/lockfile.rs b/cli/args/lockfile.rs
index 59ec7f0ef5..1805d26426 100644
--- a/cli/args/lockfile.rs
+++ b/cli/args/lockfile.rs
@@ -24,11 +24,20 @@ use crate::args::InstallKind;
 
 use deno_lockfile::Lockfile;
 
+#[derive(Debug)]
+pub struct CliLockfileReadFromPathOptions {
+  pub file_path: PathBuf,
+  pub frozen: bool,
+  /// Causes the lockfile to only be read from, but not written to.
+  pub skip_write: bool,
+}
+
 #[derive(Debug)]
 pub struct CliLockfile {
   lockfile: Mutex<Lockfile>,
   pub filename: PathBuf,
-  pub frozen: bool,
+  frozen: bool,
+  skip_write: bool,
 }
 
 pub struct Guard<'a, T> {
@@ -50,15 +59,6 @@ impl<'a, T> std::ops::DerefMut for Guard<'a, T> {
 }
 
 impl CliLockfile {
-  pub fn new(lockfile: Lockfile, frozen: bool) -> Self {
-    let filename = lockfile.filename.clone();
-    Self {
-      lockfile: Mutex::new(lockfile),
-      filename,
-      frozen,
-    }
-  }
-
   /// Get the inner deno_lockfile::Lockfile.
   pub fn lock(&self) -> Guard<Lockfile> {
     Guard {
@@ -78,6 +78,10 @@ impl CliLockfile {
   }
 
   pub fn write_if_changed(&self) -> Result<(), AnyError> {
+    if self.skip_write {
+      return Ok(());
+    }
+
     self.error_if_changed()?;
     let mut lockfile = self.lockfile.lock();
     let Some(bytes) = lockfile.resolve_write_bytes() else {
@@ -142,7 +146,7 @@ impl CliLockfile {
       return Ok(None);
     }
 
-    let filename = match flags.lock {
+    let file_path = match flags.lock {
       Some(ref lock) => PathBuf::from(lock),
       None => match workspace.resolve_lockfile_path()? {
         Some(path) => path,
@@ -160,7 +164,11 @@ impl CliLockfile {
         .unwrap_or(false)
     });
 
-    let lockfile = Self::read_from_path(filename, frozen)?;
+    let lockfile = Self::read_from_path(CliLockfileReadFromPathOptions {
+      file_path,
+      frozen,
+      skip_write: flags.internal.lockfile_skip_write,
+    })?;
 
     // initialize the lockfile with the workspace's configuration
     let root_url = workspace.root_dir();
@@ -212,25 +220,29 @@ impl CliLockfile {
   }
 
   pub fn read_from_path(
-    file_path: PathBuf,
-    frozen: bool,
+    opts: CliLockfileReadFromPathOptions,
   ) -> Result<CliLockfile, AnyError> {
-    match std::fs::read_to_string(&file_path) {
-      Ok(text) => Ok(CliLockfile::new(
-        Lockfile::new(deno_lockfile::NewLockfileOptions {
-          file_path,
-          content: &text,
-          overwrite: false,
-        })?,
-        frozen,
-      )),
-      Err(err) if err.kind() == std::io::ErrorKind::NotFound => Ok(
-        CliLockfile::new(Lockfile::new_empty(file_path, false), frozen),
-      ),
-      Err(err) => Err(err).with_context(|| {
-        format!("Failed reading lockfile '{}'", file_path.display())
-      }),
-    }
+    let lockfile = match std::fs::read_to_string(&opts.file_path) {
+      Ok(text) => Lockfile::new(deno_lockfile::NewLockfileOptions {
+        file_path: opts.file_path,
+        content: &text,
+        overwrite: false,
+      })?,
+      Err(err) if err.kind() == std::io::ErrorKind::NotFound => {
+        Lockfile::new_empty(opts.file_path, false)
+      }
+      Err(err) => {
+        return Err(err).with_context(|| {
+          format!("Failed reading lockfile '{}'", opts.file_path.display())
+        });
+      }
+    };
+    Ok(CliLockfile {
+      filename: lockfile.filename.clone(),
+      lockfile: Mutex::new(lockfile),
+      frozen: opts.frozen,
+      skip_write: opts.skip_write,
+    })
   }
 
   pub fn error_if_changed(&self) -> Result<(), AnyError> {
diff --git a/cli/args/mod.rs b/cli/args/mod.rs
index c3a4c29377..50a37b3346 100644
--- a/cli/args/mod.rs
+++ b/cli/args/mod.rs
@@ -7,6 +7,7 @@ mod import_map;
 mod lockfile;
 mod package_json;
 
+use deno_ast::MediaType;
 use deno_ast::SourceMapOption;
 use deno_config::deno_json::NodeModulesDirMode;
 use deno_config::workspace::CreateResolverOptions;
@@ -20,20 +21,20 @@ use deno_config::workspace::WorkspaceDiscoverOptions;
 use deno_config::workspace::WorkspaceDiscoverStart;
 use deno_config::workspace::WorkspaceLintConfig;
 use deno_config::workspace::WorkspaceResolver;
-use deno_core::normalize_path;
 use deno_core::resolve_url_or_path;
 use deno_graph::GraphKind;
 use deno_npm::npm_rc::NpmRc;
 use deno_npm::npm_rc::ResolvedNpmRc;
 use deno_npm::resolution::ValidSerializedNpmResolutionSnapshot;
 use deno_npm::NpmSystemInfo;
+use deno_path_util::normalize_path;
+use deno_runtime::ops::otel::OtelConfig;
 use deno_semver::npm::NpmPackageReqReference;
 use import_map::resolve_import_map_value_from_specifier;
 
 pub use deno_config::deno_json::BenchConfig;
 pub use deno_config::deno_json::ConfigFile;
 pub use deno_config::deno_json::FmtOptionsConfig;
-pub use deno_config::deno_json::JsxImportSourceConfig;
 pub use deno_config::deno_json::LintRulesConfig;
 pub use deno_config::deno_json::ProseWrap;
 pub use deno_config::deno_json::TsConfig;
@@ -44,7 +45,9 @@ pub use deno_config::glob::FilePatterns;
 pub use deno_json::check_warn_tsconfig;
 pub use flags::*;
 pub use lockfile::CliLockfile;
+pub use lockfile::CliLockfileReadFromPathOptions;
 pub use package_json::NpmInstallDepsProvider;
+pub use package_json::PackageJsonDepValueParseWithLocationError;
 
 use deno_ast::ModuleSpecifier;
 use deno_core::anyhow::bail;
@@ -199,6 +202,8 @@ pub fn ts_config_to_transpile_and_emit_options(
       precompile_jsx_dynamic_props: None,
       transform_jsx,
       var_decl_imports: false,
+      // todo(dsherret): support verbatim_module_syntax here properly
+      verbatim_module_syntax: false,
     },
     deno_ast::EmitOptions {
       inline_sources: options.inline_sources,
@@ -577,6 +582,7 @@ fn discover_npmrc(
     let resolved = npmrc
       .as_resolved(npm_registry_url())
       .context("Failed to resolve .npmrc options")?;
+    log::debug!(".npmrc found at: '{}'", path.display());
     Ok(Arc::new(resolved))
   }
 
@@ -817,18 +823,14 @@ impl CliOptions {
       };
       let msg =
         format!("DANGER: TLS certificate validation is disabled {}", domains);
-      #[allow(clippy::print_stderr)]
       {
-        // use eprintln instead of log::warn so this always gets shown
-        eprintln!("{}", colors::yellow(msg));
+        log::error!("{}", colors::yellow(msg));
       }
     }
 
-    warn_insecure_allow_run_flags(&flags);
-
     let maybe_lockfile = maybe_lockfile.filter(|_| !force_global_cache);
     let deno_dir_provider =
-      Arc::new(DenoDirProvider::new(flags.cache_path.clone()));
+      Arc::new(DenoDirProvider::new(flags.internal.cache_path.clone()));
     let maybe_node_modules_folder = resolve_node_modules_folder(
       &initial_cwd,
       &flags,
@@ -964,6 +966,9 @@ impl CliOptions {
     match self.sub_command() {
       DenoSubcommand::Cache(_) => GraphKind::All,
       DenoSubcommand::Check(_) => GraphKind::TypesOnly,
+      DenoSubcommand::Install(InstallFlags {
+        kind: InstallKind::Local(_),
+      }) => GraphKind::All,
       _ => self.type_check_mode().as_graph_kind(),
     }
   }
@@ -1123,6 +1128,10 @@ impl CliOptions {
     }
   }
 
+  pub fn otel_config(&self) -> Option<OtelConfig> {
+    self.flags.otel_config()
+  }
+
   pub fn env_file_name(&self) -> Option<&String> {
     self.flags.env_file.as_ref()
   }
@@ -1131,25 +1140,34 @@ impl CliOptions {
     self
       .main_module_cell
       .get_or_init(|| {
-        let main_module = match &self.flags.subcommand {
+        Ok(match &self.flags.subcommand {
           DenoSubcommand::Compile(compile_flags) => {
             resolve_url_or_path(&compile_flags.source_file, self.initial_cwd())?
           }
           DenoSubcommand::Eval(_) => {
-            resolve_url_or_path("./$deno$eval.ts", self.initial_cwd())?
+            resolve_url_or_path("./$deno$eval.mts", self.initial_cwd())?
           }
           DenoSubcommand::Repl(_) => {
-            resolve_url_or_path("./$deno$repl.ts", self.initial_cwd())?
+            resolve_url_or_path("./$deno$repl.mts", self.initial_cwd())?
           }
           DenoSubcommand::Run(run_flags) => {
             if run_flags.is_stdin() {
-              resolve_url_or_path("./$deno$stdin.ts", self.initial_cwd())?
-            } else if NpmPackageReqReference::from_str(&run_flags.script)
-              .is_ok()
-            {
-              ModuleSpecifier::parse(&run_flags.script)?
+              resolve_url_or_path("./$deno$stdin.mts", self.initial_cwd())?
             } else {
-              resolve_url_or_path(&run_flags.script, self.initial_cwd())?
+              let url =
+                resolve_url_or_path(&run_flags.script, self.initial_cwd())?;
+              if self.is_node_main()
+                && url.scheme() == "file"
+                && MediaType::from_specifier(&url) == MediaType::Unknown
+              {
+                try_resolve_node_binary_main_entrypoint(
+                  &run_flags.script,
+                  self.initial_cwd(),
+                )?
+                .unwrap_or(url)
+              } else {
+                url
+              }
             }
           }
           DenoSubcommand::Serve(run_flags) => {
@@ -1158,9 +1176,7 @@ impl CliOptions {
           _ => {
             bail!("No main module.")
           }
-        };
-
-        Ok(main_module)
+        })
       })
       .as_ref()
       .map_err(|err| deno_core::anyhow::anyhow!("{}", err))
@@ -1209,7 +1225,7 @@ impl CliOptions {
   // This is triggered via a secret environment variable which is used
   // for functionality like child_process.fork. Users should NOT depend
   // on this functionality.
-  pub fn is_npm_main(&self) -> bool {
+  pub fn is_node_main(&self) -> bool {
     NPM_PROCESS_STATE.is_some()
   }
 
@@ -1453,6 +1469,12 @@ impl CliOptions {
       watch: Some(WatchFlagsWithPaths { hmr, .. }),
       ..
     }) = &self.flags.subcommand
+    {
+      *hmr
+    } else if let DenoSubcommand::Serve(ServeFlags {
+      watch: Some(WatchFlagsWithPaths { hmr, .. }),
+      ..
+    }) = &self.flags.subcommand
     {
       *hmr
     } else {
@@ -1581,6 +1603,13 @@ impl CliOptions {
       || self.workspace().has_unstable("bare-node-builtins")
   }
 
+  pub fn detect_cjs(&self) -> bool {
+    // only enabled when there's a package.json in order to not have a
+    // perf penalty for non-npm Deno projects of searching for the closest
+    // package.json beside each module
+    self.workspace().package_jsons().next().is_some() || self.is_node_main()
+  }
+
   fn byonm_enabled(&self) -> bool {
     // check if enabled via unstable
     self.node_modules_dir().ok().flatten() == Some(NodeModulesDirMode::Manual)
@@ -1591,6 +1620,15 @@ impl CliOptions {
   }
 
   pub fn use_byonm(&self) -> bool {
+    if matches!(
+      self.sub_command(),
+      DenoSubcommand::Install(_)
+        | DenoSubcommand::Add(_)
+        | DenoSubcommand::Remove(_)
+    ) {
+      // For `deno install/add/remove` we want to force the managed resolver so it can set up `node_modules/` directory.
+      return false;
+    }
     if self.node_modules_dir().ok().flatten().is_none()
       && self.maybe_node_modules_folder.is_some()
       && self
@@ -1625,21 +1663,16 @@ impl CliOptions {
       });
 
     if !from_config_file.is_empty() {
-      // collect unstable granular flags
-      let mut all_valid_unstable_flags: Vec<&str> =
-        crate::UNSTABLE_GRANULAR_FLAGS
-          .iter()
-          .map(|granular_flag| granular_flag.name)
-          .collect();
-
-      let mut another_unstable_flags = Vec::from([
-        "sloppy-imports",
-        "byonm",
-        "bare-node-builtins",
-        "fmt-component",
-      ]);
-      // add more unstable flags to the same vector holding granular flags
-      all_valid_unstable_flags.append(&mut another_unstable_flags);
+      let all_valid_unstable_flags: Vec<&str> = crate::UNSTABLE_GRANULAR_FLAGS
+        .iter()
+        .map(|granular_flag| granular_flag.name)
+        .chain([
+          "sloppy-imports",
+          "byonm",
+          "bare-node-builtins",
+          "fmt-component",
+        ])
+        .collect();
 
       // check and warn if the unstable flag of config file isn't supported, by
       // iterating through the vector holding the unstable flags
@@ -1672,6 +1705,10 @@ impl CliOptions {
     if let DenoSubcommand::Run(RunFlags {
       watch: Some(WatchFlagsWithPaths { paths, .. }),
       ..
+    })
+    | DenoSubcommand::Serve(ServeFlags {
+      watch: Some(WatchFlagsWithPaths { paths, .. }),
+      ..
     }) = &self.flags.subcommand
     {
       full_paths.extend(paths.iter().map(|path| self.initial_cwd.join(path)));
@@ -1714,27 +1751,6 @@ impl CliOptions {
   }
 }
 
-/// Warns for specific uses of `--allow-run`. This function is not
-/// intended to catch every single possible insecure use of `--allow-run`,
-/// but is just an attempt to discourage some common pitfalls.
-fn warn_insecure_allow_run_flags(flags: &Flags) {
-  let permissions = &flags.permissions;
-  if permissions.allow_all {
-    return;
-  }
-  let Some(allow_run_list) = permissions.allow_run.as_ref() else {
-    return;
-  };
-
-  // discourage using --allow-run without an allow list
-  if allow_run_list.is_empty() {
-    log::warn!(
-      "{} --allow-run without an allow list is susceptible to exploits. Prefer specifying an allow list (https://docs.deno.com/runtime/fundamentals/security/#running-subprocesses)",
-      colors::yellow("Warning")
-    );
-  }
-}
-
 /// Resolves the path to use for a local node_modules folder.
 fn resolve_node_modules_folder(
   cwd: &Path,
@@ -1792,6 +1808,36 @@ fn resolve_node_modules_folder(
   Ok(Some(canonicalize_path_maybe_not_exists(&path)?))
 }
 
+fn try_resolve_node_binary_main_entrypoint(
+  specifier: &str,
+  initial_cwd: &Path,
+) -> Result<Option<Url>, AnyError> {
+  // node allows running files at paths without a `.js` extension
+  // or at directories with an index.js file
+  let path = deno_core::normalize_path(initial_cwd.join(specifier));
+  if path.is_dir() {
+    let index_file = path.join("index.js");
+    Ok(if index_file.is_file() {
+      Some(deno_path_util::url_from_file_path(&index_file)?)
+    } else {
+      None
+    })
+  } else {
+    let path = path.with_extension(
+      path
+        .extension()
+        .and_then(|s| s.to_str())
+        .map(|s| format!("{}.js", s))
+        .unwrap_or("js".to_string()),
+    );
+    if path.is_file() {
+      Ok(Some(deno_path_util::url_from_file_path(&path)?))
+    } else {
+      Ok(None)
+    }
+  }
+}
+
 fn resolve_import_map_specifier(
   maybe_import_map_path: Option<&str>,
   maybe_config_file: Option<&ConfigFile>,
diff --git a/cli/args/package_json.rs b/cli/args/package_json.rs
index 2529e54fdf..7dc75550c3 100644
--- a/cli/args/package_json.rs
+++ b/cli/args/package_json.rs
@@ -5,9 +5,12 @@ use std::sync::Arc;
 
 use deno_config::workspace::Workspace;
 use deno_core::serde_json;
+use deno_core::url::Url;
 use deno_package_json::PackageJsonDepValue;
+use deno_package_json::PackageJsonDepValueParseError;
 use deno_semver::npm::NpmPackageReqReference;
 use deno_semver::package::PackageReq;
+use thiserror::Error;
 
 #[derive(Debug)]
 pub struct InstallNpmRemotePkg {
@@ -22,10 +25,20 @@ pub struct InstallNpmWorkspacePkg {
   pub target_dir: PathBuf,
 }
 
+#[derive(Debug, Error, Clone)]
+#[error("Failed to install '{}'\n    at {}", alias, location)]
+pub struct PackageJsonDepValueParseWithLocationError {
+  pub location: Url,
+  pub alias: String,
+  #[source]
+  pub source: PackageJsonDepValueParseError,
+}
+
 #[derive(Debug, Default)]
 pub struct NpmInstallDepsProvider {
   remote_pkgs: Vec<InstallNpmRemotePkg>,
   workspace_pkgs: Vec<InstallNpmWorkspacePkg>,
+  pkg_json_dep_errors: Vec<PackageJsonDepValueParseWithLocationError>,
 }
 
 impl NpmInstallDepsProvider {
@@ -37,6 +50,7 @@ impl NpmInstallDepsProvider {
     // todo(dsherret): estimate capacity?
     let mut workspace_pkgs = Vec::new();
     let mut remote_pkgs = Vec::new();
+    let mut pkg_json_dep_errors = Vec::new();
     let workspace_npm_pkgs = workspace.npm_packages();
 
     for (_, folder) in workspace.config_folders() {
@@ -83,8 +97,18 @@ impl NpmInstallDepsProvider {
         let deps = pkg_json.resolve_local_package_json_deps();
         let mut pkg_pkgs = Vec::with_capacity(deps.len());
         for (alias, dep) in deps {
-          let Ok(dep) = dep else {
-            continue;
+          let dep = match dep {
+            Ok(dep) => dep,
+            Err(err) => {
+              pkg_json_dep_errors.push(
+                PackageJsonDepValueParseWithLocationError {
+                  location: pkg_json.specifier(),
+                  alias,
+                  source: err,
+                },
+              );
+              continue;
+            }
           };
           match dep {
             PackageJsonDepValue::Req(pkg_req) => {
@@ -131,14 +155,21 @@ impl NpmInstallDepsProvider {
     Self {
       remote_pkgs,
       workspace_pkgs,
+      pkg_json_dep_errors,
     }
   }
 
-  pub fn remote_pkgs(&self) -> &Vec<InstallNpmRemotePkg> {
+  pub fn remote_pkgs(&self) -> &[InstallNpmRemotePkg] {
     &self.remote_pkgs
   }
 
-  pub fn workspace_pkgs(&self) -> &Vec<InstallNpmWorkspacePkg> {
+  pub fn workspace_pkgs(&self) -> &[InstallNpmWorkspacePkg] {
     &self.workspace_pkgs
   }
+
+  pub fn pkg_json_dep_errors(
+    &self,
+  ) -> &[PackageJsonDepValueParseWithLocationError] {
+    &self.pkg_json_dep_errors
+  }
 }
diff --git a/cli/bench/encode_into.js b/cli/bench/encode_into.js
index 11f5a56d90..ab5e11b04d 100644
--- a/cli/bench/encode_into.js
+++ b/cli/bench/encode_into.js
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-// deno-lint-ignore-file no-console
+// deno-lint-ignore-file no-console no-process-globals
 
 let [total, count] = typeof Deno !== "undefined"
   ? Deno.args
diff --git a/cli/bench/getrandom.js b/cli/bench/getrandom.js
index 3c3ec4aa19..fe99bbcbdf 100644
--- a/cli/bench/getrandom.js
+++ b/cli/bench/getrandom.js
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-// deno-lint-ignore-file no-console
+// deno-lint-ignore-file no-console no-process-globals
 
 let [total, count] = typeof Deno !== "undefined"
   ? Deno.args
diff --git a/cli/bench/http.rs b/cli/bench/http.rs
deleted file mode 100644
index f739b76ba8..0000000000
--- a/cli/bench/http.rs
+++ /dev/null
@@ -1,167 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-use std::collections::HashMap;
-use std::net::TcpStream;
-use std::path::Path;
-use std::process::Command;
-use std::sync::atomic::AtomicU16;
-use std::sync::atomic::Ordering;
-use std::time::Duration;
-use std::time::Instant;
-
-use super::Result;
-
-pub use test_util::parse_wrk_output;
-pub use test_util::WrkOutput as HttpBenchmarkResult;
-// Some of the benchmarks in this file have been renamed. In case the history
-// somehow gets messed up:
-//   "node_http" was once called "node"
-//   "deno_tcp" was once called "deno"
-//   "deno_http" was once called "deno_net_http"
-
-const DURATION: &str = "10s";
-
-pub fn benchmark(
-  target_path: &Path,
-) -> Result<HashMap<String, HttpBenchmarkResult>> {
-  let deno_exe = test_util::deno_exe_path();
-  let deno_exe = deno_exe.to_string();
-
-  let hyper_hello_exe = target_path.join("test_server");
-  let hyper_hello_exe = hyper_hello_exe.to_str().unwrap();
-
-  let mut res = HashMap::new();
-  let manifest_dir = Path::new(env!("CARGO_MANIFEST_DIR"));
-  let http_dir = manifest_dir.join("bench").join("http");
-  for entry in std::fs::read_dir(&http_dir)? {
-    let entry = entry?;
-    let pathbuf = entry.path();
-    let path = pathbuf.to_str().unwrap();
-    if path.ends_with(".lua") {
-      continue;
-    }
-    let file_stem = pathbuf.file_stem().unwrap().to_str().unwrap();
-
-    let lua_script = http_dir.join(format!("{file_stem}.lua"));
-    let mut maybe_lua = None;
-    if lua_script.exists() {
-      maybe_lua = Some(lua_script.to_str().unwrap());
-    }
-
-    let port = get_port();
-    // deno run -A --unstable-net <path> <addr>
-    res.insert(
-      file_stem.to_string(),
-      run(
-        &[
-          deno_exe.as_str(),
-          "run",
-          "--allow-all",
-          "--unstable-net",
-          "--enable-testing-features-do-not-use",
-          path,
-          &server_addr(port),
-        ],
-        port,
-        None,
-        None,
-        maybe_lua,
-      )?,
-    );
-  }
-
-  res.insert("hyper".to_string(), hyper_http(hyper_hello_exe)?);
-
-  Ok(res)
-}
-
-fn run(
-  server_cmd: &[&str],
-  port: u16,
-  env: Option<Vec<(String, String)>>,
-  origin_cmd: Option<&[&str]>,
-  lua_script: Option<&str>,
-) -> Result<HttpBenchmarkResult> {
-  // Wait for port 4544 to become available.
-  // TODO Need to use SO_REUSEPORT with tokio::net::TcpListener.
-  std::thread::sleep(Duration::from_secs(5));
-
-  let mut origin = None;
-  if let Some(cmd) = origin_cmd {
-    let mut com = Command::new(cmd[0]);
-    com.args(&cmd[1..]);
-    if let Some(env) = env.clone() {
-      com.envs(env);
-    }
-    origin = Some(com.spawn()?);
-  };
-
-  println!("{}", server_cmd.join(" "));
-  let mut server = {
-    let mut com = Command::new(server_cmd[0]);
-    com.args(&server_cmd[1..]);
-    if let Some(env) = env {
-      com.envs(env);
-    }
-    com.spawn()?
-  };
-
-  // Wait for server to wake up.
-  let now = Instant::now();
-  let addr = format!("127.0.0.1:{port}");
-  while now.elapsed().as_secs() < 30 {
-    if TcpStream::connect(&addr).is_ok() {
-      break;
-    }
-    std::thread::sleep(Duration::from_millis(10));
-  }
-  TcpStream::connect(&addr).expect("Failed to connect to server in time");
-  println!("Server took {} ms to start", now.elapsed().as_millis());
-
-  let wrk = test_util::prebuilt_tool_path("wrk");
-  assert!(wrk.is_file());
-
-  let addr = format!("http://{addr}/");
-  let wrk = wrk.to_string();
-  let mut wrk_cmd = vec![wrk.as_str(), "-d", DURATION, "--latency", &addr];
-
-  if let Some(lua_script) = lua_script {
-    wrk_cmd.push("-s");
-    wrk_cmd.push(lua_script);
-  }
-
-  println!("{}", wrk_cmd.join(" "));
-  let output = test_util::run_collect(&wrk_cmd, None, None, None, true).0;
-
-  std::thread::sleep(Duration::from_secs(1)); // wait to capture failure. TODO racy.
-
-  println!("{output}");
-  assert!(
-    server.try_wait()?.map(|s| s.success()).unwrap_or(true),
-    "server ended with error"
-  );
-
-  server.kill()?;
-  if let Some(mut origin) = origin {
-    origin.kill()?;
-  }
-
-  Ok(parse_wrk_output(&output))
-}
-
-static NEXT_PORT: AtomicU16 = AtomicU16::new(4544);
-pub(crate) fn get_port() -> u16 {
-  let p = NEXT_PORT.load(Ordering::SeqCst);
-  NEXT_PORT.store(p.wrapping_add(1), Ordering::SeqCst);
-  p
-}
-
-fn server_addr(port: u16) -> String {
-  format!("0.0.0.0:{port}")
-}
-
-fn hyper_http(exe: &str) -> Result<HttpBenchmarkResult> {
-  let port = get_port();
-  println!("http_benchmark testing RUST hyper");
-  run(&[exe, &port.to_string()], port, None, None, None)
-}
diff --git a/cli/bench/http/deno_flash_hono_router.js b/cli/bench/http/deno_flash_hono_router.js
deleted file mode 100644
index baced0cece..0000000000
--- a/cli/bench/http/deno_flash_hono_router.js
+++ /dev/null
@@ -1,10 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-import { Hono } from "https://deno.land/x/hono@v2.0.9/mod.ts";
-
-const addr = Deno.args[0] || "127.0.0.1:4500";
-const [hostname, port] = addr.split(":");
-
-const app = new Hono();
-app.get("/", (c) => c.text("Hello, World!"));
-
-Deno.serve({ port: Number(port), hostname }, app.fetch);
diff --git a/cli/bench/http/deno_flash_send_file.js b/cli/bench/http/deno_flash_send_file.js
deleted file mode 100644
index bf8541f8b0..0000000000
--- a/cli/bench/http/deno_flash_send_file.js
+++ /dev/null
@@ -1,14 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-const addr = Deno.args[0] || "127.0.0.1:4500";
-const [hostname, port] = addr.split(":");
-const { serve } = Deno;
-
-const path = new URL("../testdata/128k.bin", import.meta.url).pathname;
-
-function handler() {
-  const file = Deno.openSync(path);
-  return new Response(file.readable);
-}
-
-serve({ hostname, port: Number(port) }, handler);
diff --git a/cli/bench/http/deno_http_read_headers.lua b/cli/bench/http/deno_http_read_headers.lua
deleted file mode 100644
index 64f1923ff3..0000000000
--- a/cli/bench/http/deno_http_read_headers.lua
+++ /dev/null
@@ -1,5 +0,0 @@
-wrk.headers["foo"] = "bar"
-wrk.headers["User-Agent"] = "Mozilla/5.0 (Macintosh; Intel Mac OS X 10_15_7) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/103.0.0.0 Safari/537.36"
-wrk.headers["Viewport-Width"] = "1920"
-wrk.headers["Accept"] = "text/html,application/xhtml+xml,application/xml;q=0.9,image/avif,image/webp,image/apng,*/*;q=0.8,application/signed-exchange;v=b3;q=0.9"
-wrk.headers["Accept-Language"] = "en,la;q=0.9"
\ No newline at end of file
diff --git a/cli/bench/http/deno_http_serve.js b/cli/bench/http/deno_http_serve.js
deleted file mode 100644
index 639982ce60..0000000000
--- a/cli/bench/http/deno_http_serve.js
+++ /dev/null
@@ -1,11 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-const addr = Deno.args[0] ?? "127.0.0.1:4500";
-const [hostname, port] = addr.split(":");
-const { serve } = Deno;
-
-function handler() {
-  return new Response("Hello World");
-}
-
-serve({ hostname, port: Number(port), reusePort: true }, handler);
diff --git a/cli/bench/http/deno_post_bin.lua b/cli/bench/http/deno_post_bin.lua
deleted file mode 100644
index c8f5d3e3f7..0000000000
--- a/cli/bench/http/deno_post_bin.lua
+++ /dev/null
@@ -1,5 +0,0 @@
-wrk.method = "POST"
-wrk.headers["Content-Type"] = "application/octet-stream"
-
-file = io.open("./cli/bench/testdata/128k.bin", "rb")
-wrk.body = file:read("*a")
\ No newline at end of file
diff --git a/cli/bench/http/deno_post_json.lua b/cli/bench/http/deno_post_json.lua
deleted file mode 100644
index cc6c4e226d..0000000000
--- a/cli/bench/http/deno_post_json.lua
+++ /dev/null
@@ -1,3 +0,0 @@
-wrk.method = "POST"
-wrk.headers["Content-Type"] = "application/json"
-wrk.body = '{"hello":"deno"}'
\ No newline at end of file
diff --git a/cli/bench/http/deno_reactdom_ssr_flash.jsx b/cli/bench/http/deno_reactdom_ssr_flash.jsx
deleted file mode 100644
index eaabf89121..0000000000
--- a/cli/bench/http/deno_reactdom_ssr_flash.jsx
+++ /dev/null
@@ -1,25 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-import { renderToReadableStream } from "https://esm.run/react-dom/server";
-import * as React from "https://esm.run/react";
-const { serve } = Deno;
-const addr = Deno.args[0] || "127.0.0.1:4500";
-const [hostname, port] = addr.split(":");
-
-const App = () => (
-  <html>
-    <body>
-      <h1>Hello World</h1>
-    </body>
-  </html>
-);
-
-const headers = {
-  headers: {
-    "Content-Type": "text/html",
-  },
-};
-
-serve({ hostname, port: Number(port) }, async () => {
-  return new Response(await renderToReadableStream(<App />), headers);
-});
diff --git a/cli/bench/http/deno_tcp.ts b/cli/bench/http/deno_tcp.ts
deleted file mode 100644
index b795910737..0000000000
--- a/cli/bench/http/deno_tcp.ts
+++ /dev/null
@@ -1,34 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-// Used for benchmarking Deno's networking.
-// TODO(bartlomieju): Replace this with a real HTTP server once
-// https://github.com/denoland/deno/issues/726 is completed.
-// Note: this is a keep-alive server.
-// deno-lint-ignore-file no-console
-const addr = Deno.args[0] || "127.0.0.1:4500";
-const [hostname, port] = addr.split(":");
-const listener = Deno.listen({ hostname, port: Number(port) });
-const response = new TextEncoder().encode(
-  "HTTP/1.1 200 OK\r\nContent-Length: 12\r\n\r\nHello World\n",
-);
-async function handle(conn: Deno.Conn): Promise<void> {
-  const buffer = new Uint8Array(1024);
-  try {
-    while (true) {
-      await conn.read(buffer);
-      await conn.write(response);
-    }
-  } catch (e) {
-    if (
-      !(e instanceof Deno.errors.BrokenPipe) &&
-      !(e instanceof Deno.errors.ConnectionReset)
-    ) {
-      throw e;
-    }
-  }
-  conn.close();
-}
-
-console.log("Listening on", addr);
-for await (const conn of listener) {
-  handle(conn);
-}
diff --git a/cli/bench/lsp.rs b/cli/bench/lsp.rs
index b088865c6b..7baaffca7e 100644
--- a/cli/bench/lsp.rs
+++ b/cli/bench/lsp.rs
@@ -150,7 +150,11 @@ fn bench_big_file_edits(deno_exe: &Path) -> Duration {
     .deno_exe(deno_exe)
     .build();
   client.initialize_default();
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
   client.change_configuration(json!({ "deno": { "enable": true } }));
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
 
   client.write_notification(
     "textDocument/didOpen",
@@ -206,6 +210,8 @@ fn bench_code_lens(deno_exe: &Path) -> Duration {
     .deno_exe(deno_exe)
     .build();
   client.initialize_default();
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
   client.change_configuration(json!({ "deno": {
     "enable": true,
     "codeLens": {
@@ -214,6 +220,8 @@ fn bench_code_lens(deno_exe: &Path) -> Duration {
       "test": true,
     },
   } }));
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
 
   client.write_notification(
     "textDocument/didOpen",
@@ -257,7 +265,11 @@ fn bench_find_replace(deno_exe: &Path) -> Duration {
     .deno_exe(deno_exe)
     .build();
   client.initialize_default();
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
   client.change_configuration(json!({ "deno": { "enable": true } }));
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
 
   for i in 0..10 {
     client.write_notification(
@@ -341,7 +353,11 @@ fn bench_startup_shutdown(deno_exe: &Path) -> Duration {
     .deno_exe(deno_exe)
     .build();
   client.initialize_default();
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
   client.change_configuration(json!({ "deno": { "enable": true } }));
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
 
   client.write_notification(
     "textDocument/didOpen",
diff --git a/cli/bench/lsp_bench_standalone.rs b/cli/bench/lsp_bench_standalone.rs
index 9c4f264ec9..3c946cfbe3 100644
--- a/cli/bench/lsp_bench_standalone.rs
+++ b/cli/bench/lsp_bench_standalone.rs
@@ -13,7 +13,11 @@ use test_util::lsp::LspClientBuilder;
 fn incremental_change_wait(bench: &mut Bencher) {
   let mut client = LspClientBuilder::new().use_diagnostic_sync(false).build();
   client.initialize_default();
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
   client.change_configuration(json!({ "deno": { "enable": true } }));
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
 
   client.write_notification(
     "textDocument/didOpen",
diff --git a/cli/bench/main.rs b/cli/bench/main.rs
index 72fa7e9636..c3c42d2488 100644
--- a/cli/bench/main.rs
+++ b/cli/bench/main.rs
@@ -17,7 +17,6 @@ use std::process::Stdio;
 use std::time::SystemTime;
 use test_util::PathRef;
 
-mod http;
 mod lsp;
 
 fn read_json(filename: &Path) -> Result<Value> {
@@ -345,9 +344,11 @@ struct BenchResult {
   binary_size: HashMap<String, i64>,
   bundle_size: HashMap<String, i64>,
   cargo_deps: usize,
+  // TODO(bartlomieju): remove
   max_latency: HashMap<String, f64>,
   max_memory: HashMap<String, i64>,
   lsp_exec_time: HashMap<String, i64>,
+  // TODO(bartlomieju): remove
   req_per_sec: HashMap<String, i64>,
   syscall_count: HashMap<String, i64>,
   thread_count: HashMap<String, i64>,
@@ -362,7 +363,6 @@ async fn main() -> Result<()> {
     "binary_size",
     "cargo_deps",
     "lsp",
-    "http",
     "strace",
     "mem_usage",
   ];
@@ -427,21 +427,6 @@ async fn main() -> Result<()> {
     new_data.lsp_exec_time = lsp_exec_times;
   }
 
-  if benchmarks.contains(&"http") && cfg!(not(target_os = "windows")) {
-    let stats = http::benchmark(target_dir.as_path())?;
-    let req_per_sec = stats
-      .iter()
-      .map(|(name, result)| (name.clone(), result.requests as i64))
-      .collect();
-    new_data.req_per_sec = req_per_sec;
-    let max_latency = stats
-      .iter()
-      .map(|(name, result)| (name.clone(), result.latency))
-      .collect();
-
-    new_data.max_latency = max_latency;
-  }
-
   if cfg!(target_os = "linux") && benchmarks.contains(&"strace") {
     use std::io::Read;
 
diff --git a/cli/bench/op_now.js b/cli/bench/op_now.js
index bcc3ea3c56..7c1427c809 100644
--- a/cli/bench/op_now.js
+++ b/cli/bench/op_now.js
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-// deno-lint-ignore-file no-console
+// deno-lint-ignore-file no-console no-process-globals
 
 const queueMicrotask = globalThis.queueMicrotask || process.nextTick;
 let [total, count] = typeof Deno !== "undefined"
diff --git a/cli/bench/secure_curves.js b/cli/bench/secure_curves.js
index 02d248b23f..912b75cccd 100644
--- a/cli/bench/secure_curves.js
+++ b/cli/bench/secure_curves.js
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-// deno-lint-ignore-file no-console
+// deno-lint-ignore-file no-console no-process-globals
 
 let [total, count] = typeof Deno !== "undefined"
   ? Deno.args
diff --git a/cli/bench/tty.js b/cli/bench/tty.js
index 248a901137..e494e76af7 100644
--- a/cli/bench/tty.js
+++ b/cli/bench/tty.js
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-// deno-lint-ignore-file no-console
+// deno-lint-ignore-file no-console no-process-globals
 
 const queueMicrotask = globalThis.queueMicrotask || process.nextTick;
 let [total, count] = typeof Deno !== "undefined"
diff --git a/cli/bench/url_parse.js b/cli/bench/url_parse.js
index 367cf73f46..9cb0045f64 100644
--- a/cli/bench/url_parse.js
+++ b/cli/bench/url_parse.js
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-// deno-lint-ignore-file no-console
+// deno-lint-ignore-file no-console no-process-globals
 
 const queueMicrotask = globalThis.queueMicrotask || process.nextTick;
 let [total, count] = typeof Deno !== "undefined"
diff --git a/cli/bench/write_file.js b/cli/bench/write_file.js
index 104a23a8db..747503ce2a 100644
--- a/cli/bench/write_file.js
+++ b/cli/bench/write_file.js
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-// deno-lint-ignore-file no-console
+// deno-lint-ignore-file no-console no-process-globals
 
 const queueMicrotask = globalThis.queueMicrotask || process.nextTick;
 let [total, count] = typeof Deno !== "undefined"
diff --git a/cli/build.rs b/cli/build.rs
index c3b6f8b045..2678a8dbb0 100644
--- a/cli/build.rs
+++ b/cli/build.rs
@@ -365,6 +365,9 @@ fn main() {
     return;
   }
 
+  deno_napi::print_linker_flags("deno");
+  deno_napi::print_linker_flags("denort");
+
   // Host snapshots won't work when cross compiling.
   let target = env::var("TARGET").unwrap();
   let host = env::var("HOST").unwrap();
@@ -374,56 +377,6 @@ fn main() {
     panic!("Cross compiling with snapshot is not supported.");
   }
 
-  let symbols_file_name = match env::consts::OS {
-    "android" | "freebsd" | "openbsd" => {
-      "generated_symbol_exports_list_linux.def".to_string()
-    }
-    os => format!("generated_symbol_exports_list_{}.def", os),
-  };
-  let symbols_path = std::path::Path::new("napi")
-    .join(symbols_file_name)
-    .canonicalize()
-    .expect(
-        "Missing symbols list! Generate using tools/napi/generate_symbols_lists.js",
-    );
-
-  #[cfg(target_os = "windows")]
-  println!(
-    "cargo:rustc-link-arg-bin=deno=/DEF:{}",
-    symbols_path.display()
-  );
-
-  #[cfg(target_os = "macos")]
-  println!(
-    "cargo:rustc-link-arg-bin=deno=-Wl,-exported_symbols_list,{}",
-    symbols_path.display()
-  );
-
-  #[cfg(target_os = "linux")]
-  {
-    // If a custom compiler is set, the glibc version is not reliable.
-    // Here, we assume that if a custom compiler is used, that it will be modern enough to support a dynamic symbol list.
-    if env::var("CC").is_err()
-      && glibc_version::get_version()
-        .map(|ver| ver.major <= 2 && ver.minor < 35)
-        .unwrap_or(false)
-    {
-      println!("cargo:warning=Compiling with all symbols exported, this will result in a larger binary. Please use glibc 2.35 or later for an optimised build.");
-      println!("cargo:rustc-link-arg-bin=deno=-rdynamic");
-    } else {
-      println!(
-        "cargo:rustc-link-arg-bin=deno=-Wl,--export-dynamic-symbol-list={}",
-        symbols_path.display()
-      );
-    }
-  }
-
-  #[cfg(target_os = "android")]
-  println!(
-    "cargo:rustc-link-arg-bin=deno=-Wl,--export-dynamic-symbol-list={}",
-    symbols_path.display()
-  );
-
   // To debug snapshot issues uncomment:
   // op_fetch_asset::trace_serializer();
 
diff --git a/cli/cache/cache_db.rs b/cli/cache/cache_db.rs
index b24078f29b..329ed2d970 100644
--- a/cli/cache/cache_db.rs
+++ b/cli/cache/cache_db.rs
@@ -57,7 +57,7 @@ impl rusqlite::types::FromSql for CacheDBHash {
 }
 
 /// What should the cache should do on failure?
-#[derive(Default)]
+#[derive(Debug, Default)]
 pub enum CacheFailure {
   /// Return errors if failure mode otherwise unspecified.
   #[default]
@@ -69,6 +69,7 @@ pub enum CacheFailure {
 }
 
 /// Configuration SQL and other parameters for a [`CacheDB`].
+#[derive(Debug)]
 pub struct CacheDBConfiguration {
   /// SQL to run for a new database.
   pub table_initializer: &'static str,
@@ -98,6 +99,7 @@ impl CacheDBConfiguration {
   }
 }
 
+#[derive(Debug)]
 enum ConnectionState {
   Connected(Connection),
   Blackhole,
@@ -106,7 +108,7 @@ enum ConnectionState {
 
 /// A cache database that eagerly initializes itself off-thread, preventing initialization operations
 /// from blocking the main thread.
-#[derive(Clone)]
+#[derive(Debug, Clone)]
 pub struct CacheDB {
   // TODO(mmastrac): We can probably simplify our thread-safe implementation here
   conn: Arc<Mutex<OnceCell<ConnectionState>>>,
diff --git a/cli/cache/deno_dir.rs b/cli/cache/deno_dir.rs
index 88d8a31c04..7b7059c224 100644
--- a/cli/cache/deno_dir.rs
+++ b/cli/cache/deno_dir.rs
@@ -126,9 +126,9 @@ impl DenoDir {
     self.root.join("registries")
   }
 
-  /// Path to the dependencies cache folder.
-  pub fn deps_folder_path(&self) -> PathBuf {
-    self.root.join("deps")
+  /// Path to the remote cache folder.
+  pub fn remote_folder_path(&self) -> PathBuf {
+    self.root.join("remote")
   }
 
   /// Path to the origin data cache folder.
diff --git a/cli/cache/emit.rs b/cli/cache/emit.rs
index 6807f06c10..3c9eecfcbd 100644
--- a/cli/cache/emit.rs
+++ b/cli/cache/emit.rs
@@ -10,6 +10,7 @@ use deno_core::unsync::sync::AtomicFlag;
 use super::DiskCache;
 
 /// The cache that stores previously emitted files.
+#[derive(Debug)]
 pub struct EmitCache {
   disk_cache: DiskCache,
   emit_failed_flag: AtomicFlag,
@@ -39,7 +40,7 @@ impl EmitCache {
     &self,
     specifier: &ModuleSpecifier,
     expected_source_hash: u64,
-  ) -> Option<Vec<u8>> {
+  ) -> Option<String> {
     let emit_filename = self.get_emit_filename(specifier)?;
     let bytes = self.disk_cache.get(&emit_filename).ok()?;
     self
@@ -91,6 +92,7 @@ impl EmitCache {
 
 const LAST_LINE_PREFIX: &str = "\n// denoCacheMetadata=";
 
+#[derive(Debug)]
 struct EmitFileSerializer {
   cli_version: &'static str,
 }
@@ -100,7 +102,7 @@ impl EmitFileSerializer {
     &self,
     mut bytes: Vec<u8>,
     expected_source_hash: u64,
-  ) -> Option<Vec<u8>> {
+  ) -> Option<String> {
     let last_newline_index = bytes.iter().rposition(|&b| b == b'\n')?;
     let (content, last_line) = bytes.split_at(last_newline_index);
     let hashes = last_line.strip_prefix(LAST_LINE_PREFIX.as_bytes())?;
@@ -120,7 +122,7 @@ impl EmitFileSerializer {
 
     // everything looks good, truncate and return it
     bytes.truncate(content.len());
-    Some(bytes)
+    String::from_utf8(bytes).ok()
   }
 
   pub fn serialize(&self, code: &[u8], source_hash: u64) -> Vec<u8> {
@@ -170,8 +172,6 @@ mod test {
       },
       emit_failed_flag: Default::default(),
     };
-    let to_string =
-      |bytes: Vec<u8>| -> String { String::from_utf8(bytes).unwrap() };
 
     let specifier1 =
       ModuleSpecifier::from_file_path(temp_dir.path().join("file1.ts"))
@@ -188,13 +188,10 @@ mod test {
     assert_eq!(cache.get_emit_code(&specifier1, 5), None);
     // providing the correct source hash
     assert_eq!(
-      cache.get_emit_code(&specifier1, 10).map(to_string),
+      cache.get_emit_code(&specifier1, 10),
       Some(emit_code1.clone()),
     );
-    assert_eq!(
-      cache.get_emit_code(&specifier2, 2).map(to_string),
-      Some(emit_code2)
-    );
+    assert_eq!(cache.get_emit_code(&specifier2, 2), Some(emit_code2));
 
     // try changing the cli version (should not load previous ones)
     let cache = EmitCache {
@@ -215,18 +212,12 @@ mod test {
       },
       emit_failed_flag: Default::default(),
     };
-    assert_eq!(
-      cache.get_emit_code(&specifier1, 5).map(to_string),
-      Some(emit_code1)
-    );
+    assert_eq!(cache.get_emit_code(&specifier1, 5), Some(emit_code1));
 
     // adding when already exists should not cause issue
     let emit_code3 = "asdf".to_string();
     cache.set_emit_code(&specifier1, 20, emit_code3.as_bytes());
     assert_eq!(cache.get_emit_code(&specifier1, 5), None);
-    assert_eq!(
-      cache.get_emit_code(&specifier1, 20).map(to_string),
-      Some(emit_code3)
-    );
+    assert_eq!(cache.get_emit_code(&specifier1, 20), Some(emit_code3));
   }
 }
diff --git a/cli/cache/mod.rs b/cli/cache/mod.rs
index 2d88137165..50fc135ddf 100644
--- a/cli/cache/mod.rs
+++ b/cli/cache/mod.rs
@@ -8,9 +8,9 @@ use crate::file_fetcher::FetchOptions;
 use crate::file_fetcher::FetchPermissionsOptionRef;
 use crate::file_fetcher::FileFetcher;
 use crate::file_fetcher::FileOrRedirect;
-use crate::npm::CliNpmResolver;
 use crate::util::fs::atomic_write_file_with_retries;
-use crate::util::path::specifier_has_extension;
+use crate::util::fs::atomic_write_file_with_retries_and_fs;
+use crate::util::fs::AtomicWriteFileFsAdapter;
 
 use deno_ast::MediaType;
 use deno_core::futures;
@@ -20,7 +20,9 @@ use deno_graph::source::CacheInfo;
 use deno_graph::source::LoadFuture;
 use deno_graph::source::LoadResponse;
 use deno_graph::source::Loader;
+use deno_runtime::deno_fs;
 use deno_runtime::deno_permissions::PermissionsContainer;
+use node_resolver::InNpmPackageChecker;
 use std::collections::HashMap;
 use std::path::Path;
 use std::path::PathBuf;
@@ -77,8 +79,12 @@ impl deno_cache_dir::DenoCacheEnv for RealDenoCacheEnv {
     atomic_write_file_with_retries(path, bytes, CACHE_PERM)
   }
 
-  fn remove_file(&self, path: &Path) -> std::io::Result<()> {
-    std::fs::remove_file(path)
+  fn canonicalize_path(&self, path: &Path) -> std::io::Result<PathBuf> {
+    crate::util::fs::canonicalize_path(path)
+  }
+
+  fn create_dir_all(&self, path: &Path) -> std::io::Result<()> {
+    std::fs::create_dir_all(path)
   }
 
   fn modified(&self, path: &Path) -> std::io::Result<Option<SystemTime>> {
@@ -100,6 +106,66 @@ impl deno_cache_dir::DenoCacheEnv for RealDenoCacheEnv {
   }
 }
 
+#[derive(Debug, Clone)]
+pub struct DenoCacheEnvFsAdapter<'a>(
+  pub &'a dyn deno_runtime::deno_fs::FileSystem,
+);
+
+impl<'a> deno_cache_dir::DenoCacheEnv for DenoCacheEnvFsAdapter<'a> {
+  fn read_file_bytes(&self, path: &Path) -> std::io::Result<Vec<u8>> {
+    self
+      .0
+      .read_file_sync(path, None)
+      .map_err(|err| err.into_io_error())
+  }
+
+  fn atomic_write_file(
+    &self,
+    path: &Path,
+    bytes: &[u8],
+  ) -> std::io::Result<()> {
+    atomic_write_file_with_retries_and_fs(
+      &AtomicWriteFileFsAdapter {
+        fs: self.0,
+        write_mode: CACHE_PERM,
+      },
+      path,
+      bytes,
+    )
+  }
+
+  fn canonicalize_path(&self, path: &Path) -> std::io::Result<PathBuf> {
+    self.0.realpath_sync(path).map_err(|e| e.into_io_error())
+  }
+
+  fn create_dir_all(&self, path: &Path) -> std::io::Result<()> {
+    self
+      .0
+      .mkdir_sync(path, true, None)
+      .map_err(|e| e.into_io_error())
+  }
+
+  fn modified(&self, path: &Path) -> std::io::Result<Option<SystemTime>> {
+    self
+      .0
+      .stat_sync(path)
+      .map(|stat| {
+        stat
+          .mtime
+          .map(|ts| SystemTime::UNIX_EPOCH + std::time::Duration::from_secs(ts))
+      })
+      .map_err(|e| e.into_io_error())
+  }
+
+  fn is_file(&self, path: &Path) -> bool {
+    self.0.is_file_sync(path)
+  }
+
+  fn time_now(&self) -> SystemTime {
+    SystemTime::now()
+  }
+}
+
 pub type GlobalHttpCache = deno_cache_dir::GlobalHttpCache<RealDenoCacheEnv>;
 pub type LocalHttpCache = deno_cache_dir::LocalHttpCache<RealDenoCacheEnv>;
 pub type LocalLspHttpCache =
@@ -116,28 +182,31 @@ pub struct FetchCacherOptions {
 /// A "wrapper" for the FileFetcher and DiskCache for the Deno CLI that provides
 /// a concise interface to the DENO_DIR when building module graphs.
 pub struct FetchCacher {
-  file_fetcher: Arc<FileFetcher>,
   pub file_header_overrides: HashMap<ModuleSpecifier, HashMap<String, String>>,
+  file_fetcher: Arc<FileFetcher>,
+  fs: Arc<dyn deno_fs::FileSystem>,
   global_http_cache: Arc<GlobalHttpCache>,
-  npm_resolver: Arc<dyn CliNpmResolver>,
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
   module_info_cache: Arc<ModuleInfoCache>,
   permissions: PermissionsContainer,
-  cache_info_enabled: bool,
   is_deno_publish: bool,
+  cache_info_enabled: bool,
 }
 
 impl FetchCacher {
   pub fn new(
     file_fetcher: Arc<FileFetcher>,
+    fs: Arc<dyn deno_fs::FileSystem>,
     global_http_cache: Arc<GlobalHttpCache>,
-    npm_resolver: Arc<dyn CliNpmResolver>,
+    in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
     module_info_cache: Arc<ModuleInfoCache>,
     options: FetchCacherOptions,
   ) -> Self {
     Self {
       file_fetcher,
+      fs,
       global_http_cache,
-      npm_resolver,
+      in_npm_pkg_checker,
       module_info_cache,
       file_header_overrides: options.file_header_overrides,
       permissions: options.permissions,
@@ -192,28 +261,21 @@ impl Loader for FetchCacher {
   ) -> LoadFuture {
     use deno_graph::source::CacheSetting as LoaderCacheSetting;
 
-    if specifier.scheme() == "file" {
-      if specifier.path().contains("/node_modules/") {
-        // The specifier might be in a completely different symlinked tree than
-        // what the node_modules url is in (ex. `/my-project-1/node_modules`
-        // symlinked to `/my-project-2/node_modules`), so first we checked if the path
-        // is in a node_modules dir to avoid needlessly canonicalizing, then now compare
-        // against the canonicalized specifier.
-        let specifier =
-          crate::node::resolve_specifier_into_node_modules(specifier);
-        if self.npm_resolver.in_npm_package(&specifier) {
-          return Box::pin(futures::future::ready(Ok(Some(
-            LoadResponse::External { specifier },
-          ))));
-        }
-      }
-
-      // make local CJS modules external to the graph
-      if specifier_has_extension(specifier, "cjs") {
+    if specifier.scheme() == "file"
+      && specifier.path().contains("/node_modules/")
+    {
+      // The specifier might be in a completely different symlinked tree than
+      // what the node_modules url is in (ex. `/my-project-1/node_modules`
+      // symlinked to `/my-project-2/node_modules`), so first we checked if the path
+      // is in a node_modules dir to avoid needlessly canonicalizing, then now compare
+      // against the canonicalized specifier.
+      let specifier = crate::node::resolve_specifier_into_node_modules(
+        specifier,
+        self.fs.as_ref(),
+      );
+      if self.in_npm_pkg_checker.in_npm_package(&specifier) {
         return Box::pin(futures::future::ready(Ok(Some(
-          LoadResponse::External {
-            specifier: specifier.clone(),
-          },
+          LoadResponse::External { specifier },
         ))));
       }
     }
@@ -259,6 +321,7 @@ impl Loader for FetchCacher {
             } else {
               FetchPermissionsOptionRef::DynamicContainer(&permissions)
             },
+            maybe_auth: None,
             maybe_accept: None,
             maybe_cache_setting: maybe_cache_setting.as_ref(),
           },
diff --git a/cli/cache/module_info.rs b/cli/cache/module_info.rs
index 4dbb01c37b..060a6f4f0c 100644
--- a/cli/cache/module_info.rs
+++ b/cli/cache/module_info.rs
@@ -44,18 +44,32 @@ pub static MODULE_INFO_CACHE_DB: CacheDBConfiguration = CacheDBConfiguration {
 /// A cache of `deno_graph::ModuleInfo` objects. Using this leads to a considerable
 /// performance improvement because when it exists we can skip parsing a module for
 /// deno_graph.
+#[derive(Debug)]
 pub struct ModuleInfoCache {
   conn: CacheDB,
+  parsed_source_cache: Arc<ParsedSourceCache>,
 }
 
 impl ModuleInfoCache {
   #[cfg(test)]
-  pub fn new_in_memory(version: &'static str) -> Self {
-    Self::new(CacheDB::in_memory(&MODULE_INFO_CACHE_DB, version))
+  pub fn new_in_memory(
+    version: &'static str,
+    parsed_source_cache: Arc<ParsedSourceCache>,
+  ) -> Self {
+    Self::new(
+      CacheDB::in_memory(&MODULE_INFO_CACHE_DB, version),
+      parsed_source_cache,
+    )
   }
 
-  pub fn new(conn: CacheDB) -> Self {
-    Self { conn }
+  pub fn new(
+    conn: CacheDB,
+    parsed_source_cache: Arc<ParsedSourceCache>,
+  ) -> Self {
+    Self {
+      conn,
+      parsed_source_cache,
+    }
   }
 
   /// Useful for testing: re-create this cache DB with a different current version.
@@ -63,6 +77,7 @@ impl ModuleInfoCache {
   pub(crate) fn recreate_with_version(self, version: &'static str) -> Self {
     Self {
       conn: self.conn.recreate_with_version(version),
+      parsed_source_cache: self.parsed_source_cache,
     }
   }
 
@@ -113,13 +128,10 @@ impl ModuleInfoCache {
     Ok(())
   }
 
-  pub fn as_module_analyzer<'a>(
-    &'a self,
-    parsed_source_cache: &'a Arc<ParsedSourceCache>,
-  ) -> ModuleInfoCacheModuleAnalyzer<'a> {
+  pub fn as_module_analyzer(&self) -> ModuleInfoCacheModuleAnalyzer {
     ModuleInfoCacheModuleAnalyzer {
       module_info_cache: self,
-      parsed_source_cache,
+      parsed_source_cache: &self.parsed_source_cache,
     }
   }
 }
@@ -129,6 +141,84 @@ pub struct ModuleInfoCacheModuleAnalyzer<'a> {
   parsed_source_cache: &'a Arc<ParsedSourceCache>,
 }
 
+impl<'a> ModuleInfoCacheModuleAnalyzer<'a> {
+  fn load_cached_module_info(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+    source_hash: CacheDBHash,
+  ) -> Option<ModuleInfo> {
+    match self.module_info_cache.get_module_info(
+      specifier,
+      media_type,
+      source_hash,
+    ) {
+      Ok(Some(info)) => Some(info),
+      Ok(None) => None,
+      Err(err) => {
+        log::debug!(
+          "Error loading module cache info for {}. {:#}",
+          specifier,
+          err
+        );
+        None
+      }
+    }
+  }
+
+  fn save_module_info_to_cache(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+    source_hash: CacheDBHash,
+    module_info: &ModuleInfo,
+  ) {
+    if let Err(err) = self.module_info_cache.set_module_info(
+      specifier,
+      media_type,
+      source_hash,
+      module_info,
+    ) {
+      log::debug!(
+        "Error saving module cache info for {}. {:#}",
+        specifier,
+        err
+      );
+    }
+  }
+
+  pub fn analyze_sync(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+    source: &Arc<str>,
+  ) -> Result<ModuleInfo, deno_ast::ParseDiagnostic> {
+    // attempt to load from the cache
+    let source_hash = CacheDBHash::from_source(source);
+    if let Some(info) =
+      self.load_cached_module_info(specifier, media_type, source_hash)
+    {
+      return Ok(info);
+    }
+
+    // otherwise, get the module info from the parsed source cache
+    let parser = self.parsed_source_cache.as_capturing_parser();
+    let analyzer = ParserModuleAnalyzer::new(&parser);
+    let module_info =
+      analyzer.analyze_sync(specifier, source.clone(), media_type)?;
+
+    // then attempt to cache it
+    self.save_module_info_to_cache(
+      specifier,
+      media_type,
+      source_hash,
+      &module_info,
+    );
+
+    Ok(module_info)
+  }
+}
+
 #[async_trait::async_trait(?Send)]
 impl<'a> deno_graph::ModuleAnalyzer for ModuleInfoCacheModuleAnalyzer<'a> {
   async fn analyze(
@@ -139,20 +229,10 @@ impl<'a> deno_graph::ModuleAnalyzer for ModuleInfoCacheModuleAnalyzer<'a> {
   ) -> Result<ModuleInfo, deno_ast::ParseDiagnostic> {
     // attempt to load from the cache
     let source_hash = CacheDBHash::from_source(&source);
-    match self.module_info_cache.get_module_info(
-      specifier,
-      media_type,
-      source_hash,
-    ) {
-      Ok(Some(info)) => return Ok(info),
-      Ok(None) => {}
-      Err(err) => {
-        log::debug!(
-          "Error loading module cache info for {}. {:#}",
-          specifier,
-          err
-        );
-      }
+    if let Some(info) =
+      self.load_cached_module_info(specifier, media_type, source_hash)
+    {
+      return Ok(info);
     }
 
     // otherwise, get the module info from the parsed source cache
@@ -169,18 +249,12 @@ impl<'a> deno_graph::ModuleAnalyzer for ModuleInfoCacheModuleAnalyzer<'a> {
     .unwrap()?;
 
     // then attempt to cache it
-    if let Err(err) = self.module_info_cache.set_module_info(
+    self.save_module_info_to_cache(
       specifier,
       media_type,
       source_hash,
       &module_info,
-    ) {
-      log::debug!(
-        "Error saving module cache info for {}. {:#}",
-        specifier,
-        err
-      );
-    }
+    );
 
     Ok(module_info)
   }
@@ -202,7 +276,7 @@ fn serialize_media_type(media_type: MediaType) -> i64 {
     Tsx => 11,
     Json => 12,
     Wasm => 13,
-    TsBuildInfo => 14,
+    Css => 14,
     SourceMap => 15,
     Unknown => 16,
   }
@@ -217,7 +291,7 @@ mod test {
 
   #[test]
   pub fn module_info_cache_general_use() {
-    let cache = ModuleInfoCache::new_in_memory("1.0.0");
+    let cache = ModuleInfoCache::new_in_memory("1.0.0", Default::default());
     let specifier1 =
       ModuleSpecifier::parse("https://localhost/mod.ts").unwrap();
     let specifier2 =
diff --git a/cli/cache/parsed_source.rs b/cli/cache/parsed_source.rs
index e956361f46..7e819ae998 100644
--- a/cli/cache/parsed_source.rs
+++ b/cli/cache/parsed_source.rs
@@ -7,9 +7,9 @@ use deno_ast::MediaType;
 use deno_ast::ModuleSpecifier;
 use deno_ast::ParsedSource;
 use deno_core::parking_lot::Mutex;
-use deno_graph::CapturingModuleParser;
-use deno_graph::DefaultModuleParser;
-use deno_graph::ModuleParser;
+use deno_graph::CapturingEsParser;
+use deno_graph::DefaultEsParser;
+use deno_graph::EsParser;
 use deno_graph::ParseOptions;
 use deno_graph::ParsedSourceStore;
 
@@ -46,7 +46,7 @@ impl<'a> LazyGraphSourceParser<'a> {
   }
 }
 
-#[derive(Default)]
+#[derive(Debug, Default)]
 pub struct ParsedSourceCache {
   sources: Mutex<HashMap<ModuleSpecifier, ParsedSource>>,
 }
@@ -57,12 +57,11 @@ impl ParsedSourceCache {
     module: &deno_graph::JsModule,
   ) -> Result<ParsedSource, deno_ast::ParseDiagnostic> {
     let parser = self.as_capturing_parser();
-    // this will conditionally parse because it's using a CapturingModuleParser
-    parser.parse_module(ParseOptions {
+    // this will conditionally parse because it's using a CapturingEsParser
+    parser.parse_program(ParseOptions {
       specifier: &module.specifier,
       source: module.source.clone(),
       media_type: module.media_type,
-      // don't bother enabling because this method is currently only used for vendoring
       scope_analysis: false,
     })
   }
@@ -86,10 +85,9 @@ impl ParsedSourceCache {
       specifier,
       source,
       media_type,
-      // don't bother enabling because this method is currently only used for emitting
       scope_analysis: false,
     };
-    DefaultModuleParser.parse_module(options)
+    DefaultEsParser.parse_program(options)
   }
 
   /// Frees the parsed source from memory.
@@ -99,8 +97,8 @@ impl ParsedSourceCache {
 
   /// Creates a parser that will reuse a ParsedSource from the store
   /// if it exists, or else parse.
-  pub fn as_capturing_parser(&self) -> CapturingModuleParser {
-    CapturingModuleParser::new(None, self)
+  pub fn as_capturing_parser(&self) -> CapturingEsParser {
+    CapturingEsParser::new(None, self)
   }
 }
 
diff --git a/cli/clippy.toml b/cli/clippy.toml
index e20c56c47a..f1c25acfb8 100644
--- a/cli/clippy.toml
+++ b/cli/clippy.toml
@@ -1,5 +1,6 @@
 disallowed-methods = [
   { path = "reqwest::Client::new", reason = "create an HttpClient via an HttpClientProvider instead" },
+  { path = "std::process::exit", reason = "use deno_runtime::exit instead" },
 ]
 disallowed-types = [
   { path = "reqwest::Client", reason = "use crate::http_util::HttpClient instead" },
diff --git a/cli/emit.rs b/cli/emit.rs
index b3f4a4477a..3cd23b7abb 100644
--- a/cli/emit.rs
+++ b/cli/emit.rs
@@ -3,24 +3,28 @@
 use crate::cache::EmitCache;
 use crate::cache::FastInsecureHasher;
 use crate::cache::ParsedSourceCache;
+use crate::resolver::CjsTracker;
 
+use deno_ast::ModuleKind;
 use deno_ast::SourceMapOption;
 use deno_ast::SourceRange;
 use deno_ast::SourceRanged;
 use deno_ast::SourceRangedForSpanned;
+use deno_ast::TranspileModuleOptions;
 use deno_ast::TranspileResult;
 use deno_core::error::AnyError;
 use deno_core::futures::stream::FuturesUnordered;
 use deno_core::futures::FutureExt;
 use deno_core::futures::StreamExt;
-use deno_core::ModuleCodeBytes;
 use deno_core::ModuleSpecifier;
 use deno_graph::MediaType;
 use deno_graph::Module;
 use deno_graph::ModuleGraph;
 use std::sync::Arc;
 
+#[derive(Debug)]
 pub struct Emitter {
+  cjs_tracker: Arc<CjsTracker>,
   emit_cache: Arc<EmitCache>,
   parsed_source_cache: Arc<ParsedSourceCache>,
   transpile_and_emit_options:
@@ -31,6 +35,7 @@ pub struct Emitter {
 
 impl Emitter {
   pub fn new(
+    cjs_tracker: Arc<CjsTracker>,
     emit_cache: Arc<EmitCache>,
     parsed_source_cache: Arc<ParsedSourceCache>,
     transpile_options: deno_ast::TranspileOptions,
@@ -43,6 +48,7 @@ impl Emitter {
       hasher.finish()
     };
     Self {
+      cjs_tracker,
       emit_cache,
       parsed_source_cache,
       transpile_and_emit_options: Arc::new((transpile_options, emit_options)),
@@ -60,20 +66,19 @@ impl Emitter {
         continue;
       };
 
-      let is_emittable = matches!(
-        module.media_type,
-        MediaType::TypeScript
-          | MediaType::Mts
-          | MediaType::Cts
-          | MediaType::Jsx
-          | MediaType::Tsx
-      );
-      if is_emittable {
+      if module.media_type.is_emittable() {
         futures.push(
           self
             .emit_parsed_source(
               &module.specifier,
               module.media_type,
+              ModuleKind::from_is_cjs(
+                self.cjs_tracker.is_cjs_with_known_is_script(
+                  &module.specifier,
+                  module.media_type,
+                  module.is_script,
+                )?,
+              ),
               &module.source,
             )
             .boxed_local(),
@@ -92,9 +97,10 @@ impl Emitter {
   pub fn maybe_cached_emit(
     &self,
     specifier: &ModuleSpecifier,
+    module_kind: deno_ast::ModuleKind,
     source: &str,
-  ) -> Option<Vec<u8>> {
-    let source_hash = self.get_source_hash(source);
+  ) -> Option<String> {
+    let source_hash = self.get_source_hash(module_kind, source);
     self.emit_cache.get_emit_code(specifier, source_hash)
   }
 
@@ -102,25 +108,27 @@ impl Emitter {
     &self,
     specifier: &ModuleSpecifier,
     media_type: MediaType,
+    module_kind: deno_ast::ModuleKind,
     source: &Arc<str>,
-  ) -> Result<ModuleCodeBytes, AnyError> {
+  ) -> Result<String, AnyError> {
     // Note: keep this in sync with the sync version below
     let helper = EmitParsedSourceHelper(self);
-    match helper.pre_emit_parsed_source(specifier, source) {
+    match helper.pre_emit_parsed_source(specifier, module_kind, source) {
       PreEmitResult::Cached(emitted_text) => Ok(emitted_text),
       PreEmitResult::NotCached { source_hash } => {
         let parsed_source_cache = self.parsed_source_cache.clone();
         let transpile_and_emit_options =
           self.transpile_and_emit_options.clone();
-        let transpile_result = deno_core::unsync::spawn_blocking({
+        let transpiled_source = deno_core::unsync::spawn_blocking({
           let specifier = specifier.clone();
           let source = source.clone();
           move || -> Result<_, AnyError> {
             EmitParsedSourceHelper::transpile(
               &parsed_source_cache,
               &specifier,
-              source.clone(),
               media_type,
+              module_kind,
+              source.clone(),
               &transpile_and_emit_options.0,
               &transpile_and_emit_options.1,
             )
@@ -128,11 +136,12 @@ impl Emitter {
         })
         .await
         .unwrap()?;
-        Ok(helper.post_emit_parsed_source(
+        helper.post_emit_parsed_source(
           specifier,
-          transpile_result,
+          &transpiled_source,
           source_hash,
-        ))
+        );
+        Ok(transpiled_source)
       }
     }
   }
@@ -141,26 +150,29 @@ impl Emitter {
     &self,
     specifier: &ModuleSpecifier,
     media_type: MediaType,
+    module_kind: deno_ast::ModuleKind,
     source: &Arc<str>,
-  ) -> Result<ModuleCodeBytes, AnyError> {
+  ) -> Result<String, AnyError> {
     // Note: keep this in sync with the async version above
     let helper = EmitParsedSourceHelper(self);
-    match helper.pre_emit_parsed_source(specifier, source) {
+    match helper.pre_emit_parsed_source(specifier, module_kind, source) {
       PreEmitResult::Cached(emitted_text) => Ok(emitted_text),
       PreEmitResult::NotCached { source_hash } => {
-        let transpile_result = EmitParsedSourceHelper::transpile(
+        let transpiled_source = EmitParsedSourceHelper::transpile(
           &self.parsed_source_cache,
           specifier,
-          source.clone(),
           media_type,
+          module_kind,
+          source.clone(),
           &self.transpile_and_emit_options.0,
           &self.transpile_and_emit_options.1,
         )?;
-        Ok(helper.post_emit_parsed_source(
+        helper.post_emit_parsed_source(
           specifier,
-          transpile_result,
+          &transpiled_source,
           source_hash,
-        ))
+        );
+        Ok(transpiled_source)
       }
     }
   }
@@ -190,10 +202,20 @@ impl Emitter {
         // this statement is probably wrong)
         let mut options = self.transpile_and_emit_options.1.clone();
         options.source_map = SourceMapOption::None;
+        let is_cjs = self.cjs_tracker.is_cjs_with_known_is_script(
+          specifier,
+          media_type,
+          parsed_source.compute_is_script(),
+        )?;
         let transpiled_source = parsed_source
-          .transpile(&self.transpile_and_emit_options.0, &options)?
-          .into_source()
-          .into_string()?;
+          .transpile(
+            &self.transpile_and_emit_options.0,
+            &deno_ast::TranspileModuleOptions {
+              module_kind: Some(ModuleKind::from_is_cjs(is_cjs)),
+            },
+            &options,
+          )?
+          .into_source();
         Ok(transpiled_source.text)
       }
       MediaType::JavaScript
@@ -204,7 +226,7 @@ impl Emitter {
       | MediaType::Dcts
       | MediaType::Json
       | MediaType::Wasm
-      | MediaType::TsBuildInfo
+      | MediaType::Css
       | MediaType::SourceMap
       | MediaType::Unknown => {
         // clear this specifier from the parsed source cache as it's now out of date
@@ -217,16 +239,17 @@ impl Emitter {
   /// A hashing function that takes the source code and uses the global emit
   /// options then generates a string hash which can be stored to
   /// determine if the cached emit is valid or not.
-  fn get_source_hash(&self, source_text: &str) -> u64 {
+  fn get_source_hash(&self, module_kind: ModuleKind, source_text: &str) -> u64 {
     FastInsecureHasher::new_without_deno_version() // stored in the transpile_and_emit_options_hash
       .write_str(source_text)
       .write_u64(self.transpile_and_emit_options_hash)
+      .write_hashable(module_kind)
       .finish()
   }
 }
 
 enum PreEmitResult {
-  Cached(ModuleCodeBytes),
+  Cached(String),
   NotCached { source_hash: u64 },
 }
 
@@ -237,14 +260,15 @@ impl<'a> EmitParsedSourceHelper<'a> {
   pub fn pre_emit_parsed_source(
     &self,
     specifier: &ModuleSpecifier,
+    module_kind: deno_ast::ModuleKind,
     source: &Arc<str>,
   ) -> PreEmitResult {
-    let source_hash = self.0.get_source_hash(source);
+    let source_hash = self.0.get_source_hash(module_kind, source);
 
     if let Some(emit_code) =
       self.0.emit_cache.get_emit_code(specifier, source_hash)
     {
-      PreEmitResult::Cached(emit_code.into_boxed_slice().into())
+      PreEmitResult::Cached(emit_code)
     } else {
       PreEmitResult::NotCached { source_hash }
     }
@@ -253,25 +277,24 @@ impl<'a> EmitParsedSourceHelper<'a> {
   pub fn transpile(
     parsed_source_cache: &ParsedSourceCache,
     specifier: &ModuleSpecifier,
-    source: Arc<str>,
     media_type: MediaType,
+    module_kind: deno_ast::ModuleKind,
+    source: Arc<str>,
     transpile_options: &deno_ast::TranspileOptions,
     emit_options: &deno_ast::EmitOptions,
-  ) -> Result<TranspileResult, AnyError> {
+  ) -> Result<String, AnyError> {
     // nothing else needs the parsed source at this point, so remove from
     // the cache in order to not transpile owned
     let parsed_source = parsed_source_cache
       .remove_or_parse_module(specifier, source, media_type)?;
     ensure_no_import_assertion(&parsed_source)?;
-    Ok(parsed_source.transpile(transpile_options, emit_options)?)
-  }
-
-  pub fn post_emit_parsed_source(
-    &self,
-    specifier: &ModuleSpecifier,
-    transpile_result: TranspileResult,
-    source_hash: u64,
-  ) -> ModuleCodeBytes {
+    let transpile_result = parsed_source.transpile(
+      transpile_options,
+      &TranspileModuleOptions {
+        module_kind: Some(module_kind),
+      },
+      emit_options,
+    )?;
     let transpiled_source = match transpile_result {
       TranspileResult::Owned(source) => source,
       TranspileResult::Cloned(source) => {
@@ -280,12 +303,20 @@ impl<'a> EmitParsedSourceHelper<'a> {
       }
     };
     debug_assert!(transpiled_source.source_map.is_none());
+    Ok(transpiled_source.text)
+  }
+
+  pub fn post_emit_parsed_source(
+    &self,
+    specifier: &ModuleSpecifier,
+    transpiled_source: &str,
+    source_hash: u64,
+  ) {
     self.0.emit_cache.set_emit_code(
       specifier,
       source_hash,
-      &transpiled_source.source,
+      transpiled_source.as_bytes(),
     );
-    transpiled_source.source.into_boxed_slice().into()
   }
 }
 
@@ -317,7 +348,7 @@ fn ensure_no_import_assertion(
     deno_core::anyhow::anyhow!("{}", msg)
   }
 
-  let Some(module) = parsed_source.program_ref().as_module() else {
+  let deno_ast::ProgramRef::Module(module) = parsed_source.program_ref() else {
     return Ok(());
   };
 
diff --git a/cli/errors.rs b/cli/errors.rs
index 25b3fc3324..b1808f7339 100644
--- a/cli/errors.rs
+++ b/cli/errors.rs
@@ -88,6 +88,10 @@ fn get_resolution_error_class(err: &ResolutionError) -> &'static str {
   }
 }
 
+fn get_try_from_int_error_class(_: &std::num::TryFromIntError) -> &'static str {
+  "TypeError"
+}
+
 pub fn get_error_class_name(e: &AnyError) -> &'static str {
   deno_runtime::errors::get_error_class_name(e)
     .or_else(|| {
@@ -106,5 +110,9 @@ pub fn get_error_class_name(e: &AnyError) -> &'static str {
       e.downcast_ref::<ResolutionError>()
         .map(get_resolution_error_class)
     })
+    .or_else(|| {
+      e.downcast_ref::<std::num::TryFromIntError>()
+        .map(get_try_from_int_error_class)
+    })
     .unwrap_or("Error")
 }
diff --git a/cli/factory.rs b/cli/factory.rs
index 8aea635d2d..7949a83a55 100644
--- a/cli/factory.rs
+++ b/cli/factory.rs
@@ -11,6 +11,7 @@ use crate::args::StorageKeyResolver;
 use crate::args::TsConfigType;
 use crate::cache::Caches;
 use crate::cache::CodeCache;
+use crate::cache::DenoCacheEnvFsAdapter;
 use crate::cache::DenoDir;
 use crate::cache::DenoDirProvider;
 use crate::cache::EmitCache;
@@ -32,22 +33,30 @@ use crate::module_loader::ModuleLoadPreparer;
 use crate::node::CliCjsCodeAnalyzer;
 use crate::node::CliNodeCodeTranslator;
 use crate::npm::create_cli_npm_resolver;
+use crate::npm::create_in_npm_pkg_checker;
+use crate::npm::CliByonmNpmResolverCreateOptions;
+use crate::npm::CliManagedInNpmPkgCheckerCreateOptions;
+use crate::npm::CliManagedNpmResolverCreateOptions;
 use crate::npm::CliNpmResolver;
-use crate::npm::CliNpmResolverByonmCreateOptions;
 use crate::npm::CliNpmResolverCreateOptions;
-use crate::npm::CliNpmResolverManagedCreateOptions;
 use crate::npm::CliNpmResolverManagedSnapshotOption;
-use crate::resolver::CjsResolutionStore;
-use crate::resolver::CliGraphResolver;
-use crate::resolver::CliGraphResolverOptions;
-use crate::resolver::CliNodeResolver;
+use crate::npm::CreateInNpmPkgCheckerOptions;
+use crate::resolver::CjsTracker;
+use crate::resolver::CliDenoResolver;
+use crate::resolver::CliDenoResolverFs;
+use crate::resolver::CliNpmReqResolver;
+use crate::resolver::CliResolver;
+use crate::resolver::CliResolverOptions;
+use crate::resolver::CliSloppyImportsResolver;
+use crate::resolver::IsCjsResolverOptions;
 use crate::resolver::NpmModuleLoader;
-use crate::resolver::SloppyImportsResolver;
+use crate::resolver::SloppyImportsCachedFs;
 use crate::standalone::DenoCompileBinaryWriter;
 use crate::tools::check::TypeChecker;
 use crate::tools::coverage::CoverageCollector;
 use crate::tools::lint::LintRuleProvider;
 use crate::tools::run::hmr::HmrRunner;
+use crate::tsc::TypeCheckingCjsTracker;
 use crate::util::file_watcher::WatcherCommunicator;
 use crate::util::fs::canonicalize_path_maybe_not_exists;
 use crate::util::progress_bar::ProgressBar;
@@ -56,15 +65,20 @@ use crate::worker::CliMainWorkerFactory;
 use crate::worker::CliMainWorkerOptions;
 use std::path::PathBuf;
 
+use deno_cache_dir::npm::NpmCacheDir;
 use deno_config::workspace::PackageJsonDepResolution;
 use deno_config::workspace::WorkspaceResolver;
 use deno_core::error::AnyError;
 use deno_core::futures::FutureExt;
 use deno_core::FeatureChecker;
 
+use deno_resolver::npm::NpmReqResolverOptions;
+use deno_resolver::DenoResolverOptions;
+use deno_resolver::NodeAndNpmReqResolver;
 use deno_runtime::deno_fs;
 use deno_runtime::deno_node::DenoFsNodeResolverEnv;
 use deno_runtime::deno_node::NodeResolver;
+use deno_runtime::deno_node::PackageJsonResolver;
 use deno_runtime::deno_permissions::Permissions;
 use deno_runtime::deno_permissions::PermissionsContainer;
 use deno_runtime::deno_tls::rustls::RootCertStore;
@@ -74,6 +88,7 @@ use deno_runtime::inspector_server::InspectorServer;
 use deno_runtime::permissions::RuntimePermissionDescriptorParser;
 use log::warn;
 use node_resolver::analyze::NodeCodeTranslator;
+use node_resolver::InNpmPackageChecker;
 use once_cell::sync::OnceCell;
 use std::future::Future;
 use std::sync::Arc;
@@ -115,7 +130,7 @@ impl RootCertStoreProvider for CliRootCertStoreProvider {
   }
 }
 
-struct Deferred<T>(once_cell::unsync::OnceCell<T>);
+pub struct Deferred<T>(once_cell::unsync::OnceCell<T>);
 
 impl<T> Default for Deferred<T> {
   fn default() -> Self {
@@ -161,38 +176,42 @@ impl<T> Deferred<T> {
 
 #[derive(Default)]
 struct CliFactoryServices {
-  cli_options: Deferred<Arc<CliOptions>>,
+  blob_store: Deferred<Arc<BlobStore>>,
   caches: Deferred<Arc<Caches>>,
+  cjs_tracker: Deferred<Arc<CjsTracker>>,
+  cli_options: Deferred<Arc<CliOptions>>,
+  code_cache: Deferred<Arc<CodeCache>>,
+  deno_resolver: Deferred<Arc<CliDenoResolver>>,
+  emit_cache: Deferred<Arc<EmitCache>>,
+  emitter: Deferred<Arc<Emitter>>,
+  feature_checker: Deferred<Arc<FeatureChecker>>,
   file_fetcher: Deferred<Arc<FileFetcher>>,
+  fs: Deferred<Arc<dyn deno_fs::FileSystem>>,
   global_http_cache: Deferred<Arc<GlobalHttpCache>>,
   http_cache: Deferred<Arc<dyn HttpCache>>,
   http_client_provider: Deferred<Arc<HttpClientProvider>>,
-  emit_cache: Deferred<Arc<EmitCache>>,
-  emitter: Deferred<Arc<Emitter>>,
-  fs: Deferred<Arc<dyn deno_fs::FileSystem>>,
+  in_npm_pkg_checker: Deferred<Arc<dyn InNpmPackageChecker>>,
   main_graph_container: Deferred<Arc<MainModuleGraphContainer>>,
-  maybe_inspector_server: Deferred<Option<Arc<InspectorServer>>>,
-  root_cert_store_provider: Deferred<Arc<dyn RootCertStoreProvider>>,
-  blob_store: Deferred<Arc<BlobStore>>,
-  module_info_cache: Deferred<Arc<ModuleInfoCache>>,
-  parsed_source_cache: Deferred<Arc<ParsedSourceCache>>,
-  resolver: Deferred<Arc<CliGraphResolver>>,
   maybe_file_watcher_reporter: Deferred<Option<FileWatcherReporter>>,
+  maybe_inspector_server: Deferred<Option<Arc<InspectorServer>>>,
   module_graph_builder: Deferred<Arc<ModuleGraphBuilder>>,
   module_graph_creator: Deferred<Arc<ModuleGraphCreator>>,
+  module_info_cache: Deferred<Arc<ModuleInfoCache>>,
   module_load_preparer: Deferred<Arc<ModuleLoadPreparer>>,
   node_code_translator: Deferred<Arc<CliNodeCodeTranslator>>,
   node_resolver: Deferred<Arc<NodeResolver>>,
+  npm_cache_dir: Deferred<Arc<NpmCacheDir>>,
+  npm_req_resolver: Deferred<Arc<CliNpmReqResolver>>,
   npm_resolver: Deferred<Arc<dyn CliNpmResolver>>,
+  parsed_source_cache: Deferred<Arc<ParsedSourceCache>>,
   permission_desc_parser: Deferred<Arc<RuntimePermissionDescriptorParser>>,
+  pkg_json_resolver: Deferred<Arc<PackageJsonResolver>>,
+  resolver: Deferred<Arc<CliResolver>>,
+  root_cert_store_provider: Deferred<Arc<dyn RootCertStoreProvider>>,
   root_permissions_container: Deferred<PermissionsContainer>,
-  sloppy_imports_resolver: Deferred<Option<Arc<SloppyImportsResolver>>>,
+  sloppy_imports_resolver: Deferred<Option<Arc<CliSloppyImportsResolver>>>,
   text_only_progress_bar: Deferred<ProgressBar>,
   type_checker: Deferred<Arc<TypeChecker>>,
-  cjs_resolutions: Deferred<Arc<CjsResolutionStore>>,
-  cli_node_resolver: Deferred<Arc<CliNodeResolver>>,
-  feature_checker: Deferred<Arc<FeatureChecker>>,
-  code_cache: Deferred<Arc<CodeCache>>,
   workspace_resolver: Deferred<Arc<WorkspaceResolver>>,
 }
 
@@ -299,7 +318,7 @@ impl CliFactory {
   pub fn global_http_cache(&self) -> Result<&Arc<GlobalHttpCache>, AnyError> {
     self.services.global_http_cache.get_or_try_init(|| {
       Ok(Arc::new(GlobalHttpCache::new(
-        self.deno_dir()?.deps_folder_path(),
+        self.deno_dir()?.remote_folder_path(),
         crate::cache::RealDenoCacheEnv,
       )))
     })
@@ -349,72 +368,127 @@ impl CliFactory {
     self.services.fs.get_or_init(|| Arc::new(deno_fs::RealFs))
   }
 
+  pub fn in_npm_pkg_checker(
+    &self,
+  ) -> Result<&Arc<dyn InNpmPackageChecker>, AnyError> {
+    self.services.in_npm_pkg_checker.get_or_try_init(|| {
+      let cli_options = self.cli_options()?;
+      let options = if cli_options.use_byonm() {
+        CreateInNpmPkgCheckerOptions::Byonm
+      } else {
+        CreateInNpmPkgCheckerOptions::Managed(
+          CliManagedInNpmPkgCheckerCreateOptions {
+            root_cache_dir_url: self.npm_cache_dir()?.root_dir_url(),
+            maybe_node_modules_path: cli_options
+              .node_modules_dir_path()
+              .map(|p| p.as_path()),
+          },
+        )
+      };
+      Ok(create_in_npm_pkg_checker(options))
+    })
+  }
+
+  pub fn npm_cache_dir(&self) -> Result<&Arc<NpmCacheDir>, AnyError> {
+    self.services.npm_cache_dir.get_or_try_init(|| {
+      let fs = self.fs();
+      let global_path = self.deno_dir()?.npm_folder_path();
+      let cli_options = self.cli_options()?;
+      Ok(Arc::new(NpmCacheDir::new(
+        &DenoCacheEnvFsAdapter(fs.as_ref()),
+        global_path,
+        cli_options.npmrc().get_all_known_registries_urls(),
+      )))
+    })
+  }
+
   pub async fn npm_resolver(
     &self,
   ) -> Result<&Arc<dyn CliNpmResolver>, AnyError> {
     self
       .services
       .npm_resolver
-      .get_or_try_init_async(async {
-        let fs = self.fs();
-        let cli_options = self.cli_options()?;
-        // For `deno install` we want to force the managed resolver so it can set up `node_modules/` directory.
-        create_cli_npm_resolver(if cli_options.use_byonm() && !matches!(cli_options.sub_command(), DenoSubcommand::Install(_) | DenoSubcommand::Add(_) | DenoSubcommand::Remove(_)) {
-          CliNpmResolverCreateOptions::Byonm(CliNpmResolverByonmCreateOptions {
-            fs: fs.clone(),
-            root_node_modules_dir: Some(match cli_options.node_modules_dir_path() {
-              Some(node_modules_path) => node_modules_path.to_path_buf(),
-              // path needs to be canonicalized for node resolution
-              // (node_modules_dir_path above is already canonicalized)
-              None => canonicalize_path_maybe_not_exists(cli_options.initial_cwd())?
-                .join("node_modules"),
-            }),
-          })
-        } else {
-          CliNpmResolverCreateOptions::Managed(CliNpmResolverManagedCreateOptions {
-            snapshot: match cli_options.resolve_npm_resolution_snapshot()? {
-              Some(snapshot) => {
-                CliNpmResolverManagedSnapshotOption::Specified(Some(snapshot))
-              }
-              None => match cli_options.maybe_lockfile() {
-                Some(lockfile) => {
-                  CliNpmResolverManagedSnapshotOption::ResolveFromLockfile(
-                    lockfile.clone(),
-                  )
-                }
-                None => CliNpmResolverManagedSnapshotOption::Specified(None),
+      .get_or_try_init_async(
+        async {
+          let fs = self.fs();
+          let cli_options = self.cli_options()?;
+          create_cli_npm_resolver(if cli_options.use_byonm() {
+            CliNpmResolverCreateOptions::Byonm(
+              CliByonmNpmResolverCreateOptions {
+                fs: CliDenoResolverFs(fs.clone()),
+                pkg_json_resolver: self.pkg_json_resolver().clone(),
+                root_node_modules_dir: Some(
+                  match cli_options.node_modules_dir_path() {
+                    Some(node_modules_path) => node_modules_path.to_path_buf(),
+                    // path needs to be canonicalized for node resolution
+                    // (node_modules_dir_path above is already canonicalized)
+                    None => canonicalize_path_maybe_not_exists(
+                      cli_options.initial_cwd(),
+                    )?
+                    .join("node_modules"),
+                  },
+                ),
               },
-            },
-            maybe_lockfile: cli_options.maybe_lockfile().cloned(),
-            fs: fs.clone(),
-            http_client_provider: self.http_client_provider().clone(),
-            npm_global_cache_dir: self.deno_dir()?.npm_folder_path(),
-            cache_setting: cli_options.cache_setting(),
-            text_only_progress_bar: self.text_only_progress_bar().clone(),
-            maybe_node_modules_path: cli_options.node_modules_dir_path().cloned(),
-            npm_install_deps_provider: Arc::new(NpmInstallDepsProvider::from_workspace(cli_options.workspace())),
-            npm_system_info: cli_options.npm_system_info(),
-            npmrc: cli_options.npmrc().clone(),
-            lifecycle_scripts: cli_options.lifecycle_scripts_config(),
+            )
+          } else {
+            CliNpmResolverCreateOptions::Managed(
+              CliManagedNpmResolverCreateOptions {
+                snapshot: match cli_options.resolve_npm_resolution_snapshot()? {
+                  Some(snapshot) => {
+                    CliNpmResolverManagedSnapshotOption::Specified(Some(
+                      snapshot,
+                    ))
+                  }
+                  None => match cli_options.maybe_lockfile() {
+                    Some(lockfile) => {
+                      CliNpmResolverManagedSnapshotOption::ResolveFromLockfile(
+                        lockfile.clone(),
+                      )
+                    }
+                    None => {
+                      CliNpmResolverManagedSnapshotOption::Specified(None)
+                    }
+                  },
+                },
+                maybe_lockfile: cli_options.maybe_lockfile().cloned(),
+                fs: fs.clone(),
+                http_client_provider: self.http_client_provider().clone(),
+                npm_cache_dir: self.npm_cache_dir()?.clone(),
+                cache_setting: cli_options.cache_setting(),
+                text_only_progress_bar: self.text_only_progress_bar().clone(),
+                maybe_node_modules_path: cli_options
+                  .node_modules_dir_path()
+                  .cloned(),
+                npm_install_deps_provider: Arc::new(
+                  NpmInstallDepsProvider::from_workspace(
+                    cli_options.workspace(),
+                  ),
+                ),
+                npm_system_info: cli_options.npm_system_info(),
+                npmrc: cli_options.npmrc().clone(),
+                lifecycle_scripts: cli_options.lifecycle_scripts_config(),
+              },
+            )
           })
-        }).await
-      }.boxed_local())
+          .await
+        }
+        .boxed_local(),
+      )
       .await
   }
 
   pub fn sloppy_imports_resolver(
     &self,
-  ) -> Result<Option<&Arc<SloppyImportsResolver>>, AnyError> {
+  ) -> Result<Option<&Arc<CliSloppyImportsResolver>>, AnyError> {
     self
       .services
       .sloppy_imports_resolver
       .get_or_try_init(|| {
-        Ok(
-          self
-            .cli_options()?
-            .unstable_sloppy_imports()
-            .then(|| Arc::new(SloppyImportsResolver::new(self.fs().clone()))),
-        )
+        Ok(self.cli_options()?.unstable_sloppy_imports().then(|| {
+          Arc::new(CliSloppyImportsResolver::new(SloppyImportsCachedFs::new(
+            self.fs().clone(),
+          )))
+        }))
       })
       .map(|maybe| maybe.as_ref())
   }
@@ -454,28 +528,47 @@ impl CliFactory {
       .await
   }
 
-  pub async fn resolver(&self) -> Result<&Arc<CliGraphResolver>, AnyError> {
+  pub async fn deno_resolver(&self) -> Result<&Arc<CliDenoResolver>, AnyError> {
+    self
+      .services
+      .deno_resolver
+      .get_or_try_init_async(async {
+        let cli_options = self.cli_options()?;
+        Ok(Arc::new(CliDenoResolver::new(DenoResolverOptions {
+          in_npm_pkg_checker: self.in_npm_pkg_checker()?.clone(),
+          node_and_req_resolver: if cli_options.no_npm() {
+            None
+          } else {
+            Some(NodeAndNpmReqResolver {
+              node_resolver: self.node_resolver().await?.clone(),
+              npm_req_resolver: self.npm_req_resolver().await?.clone(),
+            })
+          },
+          sloppy_imports_resolver: self.sloppy_imports_resolver()?.cloned(),
+          workspace_resolver: self.workspace_resolver().await?.clone(),
+          is_byonm: cli_options.use_byonm(),
+          maybe_vendor_dir: cli_options.vendor_dir_path(),
+        })))
+      })
+      .await
+  }
+
+  pub async fn resolver(&self) -> Result<&Arc<CliResolver>, AnyError> {
     self
       .services
       .resolver
       .get_or_try_init_async(
         async {
           let cli_options = self.cli_options()?;
-          Ok(Arc::new(CliGraphResolver::new(CliGraphResolverOptions {
-            sloppy_imports_resolver: self.sloppy_imports_resolver()?.cloned(),
-            node_resolver: Some(self.cli_node_resolver().await?.clone()),
+          Ok(Arc::new(CliResolver::new(CliResolverOptions {
             npm_resolver: if cli_options.no_npm() {
               None
             } else {
               Some(self.npm_resolver().await?.clone())
             },
-            workspace_resolver: self.workspace_resolver().await?.clone(),
             bare_node_builtins_enabled: cli_options
               .unstable_bare_node_builtins(),
-            maybe_jsx_import_source_config: cli_options
-              .workspace()
-              .to_maybe_jsx_import_source_config()?,
-            maybe_vendor_dir: cli_options.vendor_dir_path(),
+            deno_resolver: self.deno_resolver().await?.clone(),
           })))
         }
         .boxed_local(),
@@ -504,6 +597,7 @@ impl CliFactory {
     self.services.module_info_cache.get_or_try_init(|| {
       Ok(Arc::new(ModuleInfoCache::new(
         self.caches()?.dep_analysis_db(),
+        self.parsed_source_cache().clone(),
       )))
     })
   }
@@ -532,6 +626,7 @@ impl CliFactory {
           ts_config_result.ts_config,
         )?;
       Ok(Arc::new(Emitter::new(
+        self.cjs_tracker()?.clone(),
         self.emit_cache()?.clone(),
         self.parsed_source_cache().clone(),
         transpile_options,
@@ -555,7 +650,13 @@ impl CliFactory {
         async {
           Ok(Arc::new(NodeResolver::new(
             DenoFsNodeResolverEnv::new(self.fs().clone()),
-            self.npm_resolver().await?.clone().into_npm_resolver(),
+            self.in_npm_pkg_checker()?.clone(),
+            self
+              .npm_resolver()
+              .await?
+              .clone()
+              .into_npm_pkg_folder_resolver(),
+            self.pkg_json_resolver().clone(),
           )))
         }
         .boxed_local(),
@@ -573,23 +674,57 @@ impl CliFactory {
         let caches = self.caches()?;
         let node_analysis_cache =
           NodeAnalysisCache::new(caches.node_analysis_db());
-        let node_resolver = self.cli_node_resolver().await?.clone();
+        let node_resolver = self.node_resolver().await?.clone();
         let cjs_esm_analyzer = CliCjsCodeAnalyzer::new(
           node_analysis_cache,
+          self.cjs_tracker()?.clone(),
           self.fs().clone(),
-          node_resolver,
+          Some(self.parsed_source_cache().clone()),
         );
 
         Ok(Arc::new(NodeCodeTranslator::new(
           cjs_esm_analyzer,
           DenoFsNodeResolverEnv::new(self.fs().clone()),
-          self.node_resolver().await?.clone(),
-          self.npm_resolver().await?.clone().into_npm_resolver(),
+          self.in_npm_pkg_checker()?.clone(),
+          node_resolver,
+          self
+            .npm_resolver()
+            .await?
+            .clone()
+            .into_npm_pkg_folder_resolver(),
+          self.pkg_json_resolver().clone(),
         )))
       })
       .await
   }
 
+  pub async fn npm_req_resolver(
+    &self,
+  ) -> Result<&Arc<CliNpmReqResolver>, AnyError> {
+    self
+      .services
+      .npm_req_resolver
+      .get_or_try_init_async(async {
+        let npm_resolver = self.npm_resolver().await?;
+        Ok(Arc::new(CliNpmReqResolver::new(NpmReqResolverOptions {
+          byonm_resolver: (npm_resolver.clone()).into_maybe_byonm(),
+          fs: CliDenoResolverFs(self.fs().clone()),
+          in_npm_pkg_checker: self.in_npm_pkg_checker()?.clone(),
+          node_resolver: self.node_resolver().await?.clone(),
+          npm_req_resolver: npm_resolver.clone().into_npm_req_resolver(),
+        })))
+      })
+      .await
+  }
+
+  pub fn pkg_json_resolver(&self) -> &Arc<PackageJsonResolver> {
+    self.services.pkg_json_resolver.get_or_init(|| {
+      Arc::new(PackageJsonResolver::new(DenoFsNodeResolverEnv::new(
+        self.fs().clone(),
+      )))
+    })
+  }
+
   pub async fn type_checker(&self) -> Result<&Arc<TypeChecker>, AnyError> {
     self
       .services
@@ -598,6 +733,10 @@ impl CliFactory {
         let cli_options = self.cli_options()?;
         Ok(Arc::new(TypeChecker::new(
           self.caches()?.clone(),
+          Arc::new(TypeCheckingCjsTracker::new(
+            self.cjs_tracker()?.clone(),
+            self.module_info_cache()?.clone(),
+          )),
           cli_options.clone(),
           self.module_graph_builder().await?.clone(),
           self.node_resolver().await?.clone(),
@@ -616,17 +755,19 @@ impl CliFactory {
       .get_or_try_init_async(async {
         let cli_options = self.cli_options()?;
         Ok(Arc::new(ModuleGraphBuilder::new(
-          cli_options.clone(),
           self.caches()?.clone(),
+          self.cjs_tracker()?.clone(),
+          cli_options.clone(),
+          self.file_fetcher()?.clone(),
           self.fs().clone(),
-          self.resolver().await?.clone(),
-          self.npm_resolver().await?.clone(),
-          self.module_info_cache()?.clone(),
-          self.parsed_source_cache().clone(),
+          self.global_http_cache()?.clone(),
+          self.in_npm_pkg_checker()?.clone(),
           cli_options.maybe_lockfile().cloned(),
           self.maybe_file_watcher_reporter().clone(),
-          self.file_fetcher()?.clone(),
-          self.global_http_cache()?.clone(),
+          self.module_info_cache()?.clone(),
+          self.npm_resolver().await?.clone(),
+          self.parsed_source_cache().clone(),
+          self.resolver().await?.clone(),
           self.root_permissions_container()?.clone(),
         )))
       })
@@ -698,25 +839,18 @@ impl CliFactory {
       .await
   }
 
-  pub fn cjs_resolutions(&self) -> &Arc<CjsResolutionStore> {
-    self.services.cjs_resolutions.get_or_init(Default::default)
-  }
-
-  pub async fn cli_node_resolver(
-    &self,
-  ) -> Result<&Arc<CliNodeResolver>, AnyError> {
-    self
-      .services
-      .cli_node_resolver
-      .get_or_try_init_async(async {
-        Ok(Arc::new(CliNodeResolver::new(
-          self.cjs_resolutions().clone(),
-          self.fs().clone(),
-          self.node_resolver().await?.clone(),
-          self.npm_resolver().await?.clone(),
-        )))
-      })
-      .await
+  pub fn cjs_tracker(&self) -> Result<&Arc<CjsTracker>, AnyError> {
+    self.services.cjs_tracker.get_or_try_init(|| {
+      let options = self.cli_options()?;
+      Ok(Arc::new(CjsTracker::new(
+        self.in_npm_pkg_checker()?.clone(),
+        self.pkg_json_resolver().clone(),
+        IsCjsResolverOptions {
+          detect_cjs: options.detect_cjs(),
+          is_node_main: options.is_node_main(),
+        },
+      )))
+    })
   }
 
   pub fn permission_desc_parser(
@@ -749,7 +883,9 @@ impl CliFactory {
   ) -> Result<DenoCompileBinaryWriter, AnyError> {
     let cli_options = self.cli_options()?;
     Ok(DenoCompileBinaryWriter::new(
+      self.cjs_tracker()?,
       self.deno_dir()?,
+      self.emitter()?,
       self.file_fetcher()?,
       self.http_client_provider(),
       self.npm_resolver().await?.as_ref(),
@@ -778,15 +914,20 @@ impl CliFactory {
     &self,
   ) -> Result<CliMainWorkerFactory, AnyError> {
     let cli_options = self.cli_options()?;
+    let fs = self.fs();
     let node_resolver = self.node_resolver().await?;
     let npm_resolver = self.npm_resolver().await?;
-    let fs = self.fs();
-    let cli_node_resolver = self.cli_node_resolver().await?;
+    let cli_npm_resolver = self.npm_resolver().await?.clone();
+    let in_npm_pkg_checker = self.in_npm_pkg_checker()?;
     let maybe_file_watcher_communicator = if cli_options.has_hmr() {
       Some(self.watcher_communicator.clone().unwrap())
     } else {
       None
     };
+    let node_code_translator = self.node_code_translator().await?;
+    let cjs_tracker = self.cjs_tracker()?.clone();
+    let pkg_json_resolver = self.pkg_json_resolver().clone();
+    let npm_req_resolver = self.npm_req_resolver().await?;
 
     Ok(CliMainWorkerFactory::new(
       self.blob_store().clone(),
@@ -796,38 +937,44 @@ impl CliFactory {
         None
       },
       self.feature_checker()?.clone(),
-      self.fs().clone(),
+      fs.clone(),
       maybe_file_watcher_communicator,
       self.maybe_inspector_server()?.clone(),
       cli_options.maybe_lockfile().cloned(),
       Box::new(CliModuleLoaderFactory::new(
         cli_options,
+        cjs_tracker,
         if cli_options.code_cache_enabled() {
           Some(self.code_cache()?.clone())
         } else {
           None
         },
         self.emitter()?.clone(),
+        fs.clone(),
+        in_npm_pkg_checker.clone(),
         self.main_module_graph_container().await?.clone(),
         self.module_load_preparer().await?.clone(),
-        cli_node_resolver.clone(),
+        node_code_translator.clone(),
+        node_resolver.clone(),
+        npm_req_resolver.clone(),
+        cli_npm_resolver.clone(),
         NpmModuleLoader::new(
-          self.cjs_resolutions().clone(),
-          self.node_code_translator().await?.clone(),
+          self.cjs_tracker()?.clone(),
           fs.clone(),
-          cli_node_resolver.clone(),
+          node_code_translator.clone(),
         ),
         self.parsed_source_cache().clone(),
         self.resolver().await?.clone(),
       )),
       node_resolver.clone(),
       npm_resolver.clone(),
-      self.permission_desc_parser()?.clone(),
+      pkg_json_resolver,
       self.root_cert_store_provider().clone(),
       self.root_permissions_container()?.clone(),
       StorageKeyResolver::from_options(cli_options),
       cli_options.sub_command().clone(),
       self.create_cli_main_worker_options()?,
+      self.cli_options()?.otel_config(),
     ))
   }
 
@@ -876,7 +1023,6 @@ impl CliFactory {
       inspect_wait: cli_options.inspect_wait().is_some(),
       strace_ops: cli_options.strace_ops().clone(),
       is_inspecting: cli_options.is_inspecting(),
-      is_npm_main: cli_options.is_npm_main(),
       location: cli_options.location_flag().clone(),
       // if the user ran a binary command, we'll need to set process.argv[0]
       // to be the name of the binary command instead of deno
diff --git a/cli/file_fetcher.rs b/cli/file_fetcher.rs
index ca11449393..95d778f0bb 100644
--- a/cli/file_fetcher.rs
+++ b/cli/file_fetcher.rs
@@ -21,9 +21,10 @@ use deno_core::url::Url;
 use deno_core::ModuleSpecifier;
 use deno_graph::source::LoaderChecksum;
 
+use deno_path_util::url_to_file_path;
 use deno_runtime::deno_permissions::PermissionsContainer;
 use deno_runtime::deno_web::BlobStore;
-use deno_runtime::fs_util::specifier_to_file_path;
+use http::header;
 use log::debug;
 use std::borrow::Cow;
 use std::collections::HashMap;
@@ -136,7 +137,7 @@ impl MemoryFiles {
 
 /// Fetch a source file from the local file system.
 fn fetch_local(specifier: &ModuleSpecifier) -> Result<File, AnyError> {
-  let local = specifier_to_file_path(specifier).map_err(|_| {
+  let local = url_to_file_path(specifier).map_err(|_| {
     uri_error(format!("Invalid file path.\n  Specifier: {specifier}"))
   })?;
   // If it doesnt have a extension, we want to treat it as typescript by default
@@ -181,6 +182,7 @@ pub enum FetchPermissionsOptionRef<'a> {
 pub struct FetchOptions<'a> {
   pub specifier: &'a ModuleSpecifier,
   pub permissions: FetchPermissionsOptionRef<'a>,
+  pub maybe_auth: Option<(header::HeaderName, header::HeaderValue)>,
   pub maybe_accept: Option<&'a str>,
   pub maybe_cache_setting: Option<&'a CacheSetting>,
 }
@@ -333,7 +335,7 @@ impl FileFetcher {
         )
       })?;
 
-    let bytes = blob.read_all().await?;
+    let bytes = blob.read_all().await;
     let headers =
       HashMap::from([("content-type".to_string(), blob.media_type.clone())]);
 
@@ -350,6 +352,7 @@ impl FileFetcher {
     maybe_accept: Option<&str>,
     cache_setting: &CacheSetting,
     maybe_checksum: Option<&LoaderChecksum>,
+    maybe_auth: Option<(header::HeaderName, header::HeaderValue)>,
   ) -> Result<FileOrRedirect, AnyError> {
     debug!(
       "FileFetcher::fetch_remote_no_follow - specifier: {}",
@@ -442,6 +445,7 @@ impl FileFetcher {
             .as_ref()
             .map(|(_, etag)| etag.clone()),
           maybe_auth_token: maybe_auth_token.clone(),
+          maybe_auth: maybe_auth.clone(),
           maybe_progress_guard: maybe_progress_guard.as_ref(),
         })
         .await?
@@ -538,7 +542,18 @@ impl FileFetcher {
     specifier: &ModuleSpecifier,
   ) -> Result<File, AnyError> {
     self
-      .fetch_inner(specifier, FetchPermissionsOptionRef::AllowAll)
+      .fetch_inner(specifier, None, FetchPermissionsOptionRef::AllowAll)
+      .await
+  }
+
+  #[inline(always)]
+  pub async fn fetch_bypass_permissions_with_maybe_auth(
+    &self,
+    specifier: &ModuleSpecifier,
+    maybe_auth: Option<(header::HeaderName, header::HeaderValue)>,
+  ) -> Result<File, AnyError> {
+    self
+      .fetch_inner(specifier, maybe_auth, FetchPermissionsOptionRef::AllowAll)
       .await
   }
 
@@ -552,6 +567,7 @@ impl FileFetcher {
     self
       .fetch_inner(
         specifier,
+        None,
         FetchPermissionsOptionRef::StaticContainer(permissions),
       )
       .await
@@ -560,12 +576,14 @@ impl FileFetcher {
   async fn fetch_inner(
     &self,
     specifier: &ModuleSpecifier,
+    maybe_auth: Option<(header::HeaderName, header::HeaderValue)>,
     permissions: FetchPermissionsOptionRef<'_>,
   ) -> Result<File, AnyError> {
     self
       .fetch_with_options(FetchOptions {
         specifier,
         permissions,
+        maybe_auth,
         maybe_accept: None,
         maybe_cache_setting: None,
       })
@@ -585,12 +603,14 @@ impl FileFetcher {
     max_redirect: usize,
   ) -> Result<File, AnyError> {
     let mut specifier = Cow::Borrowed(options.specifier);
+    let mut maybe_auth = options.maybe_auth.clone();
     for _ in 0..=max_redirect {
       match self
         .fetch_no_follow_with_options(FetchNoFollowOptions {
           fetch_options: FetchOptions {
             specifier: &specifier,
             permissions: options.permissions,
+            maybe_auth: maybe_auth.clone(),
             maybe_accept: options.maybe_accept,
             maybe_cache_setting: options.maybe_cache_setting,
           },
@@ -602,6 +622,10 @@ impl FileFetcher {
           return Ok(file);
         }
         FileOrRedirect::Redirect(redirect_specifier) => {
+          // If we were redirected to another origin, don't send the auth header anymore.
+          if redirect_specifier.origin() != specifier.origin() {
+            maybe_auth = None;
+          }
           specifier = Cow::Owned(redirect_specifier);
         }
       }
@@ -666,6 +690,7 @@ impl FileFetcher {
           options.maybe_accept,
           options.maybe_cache_setting.unwrap_or(&self.cache_setting),
           maybe_checksum,
+          options.maybe_auth,
         )
         .await
     }
@@ -726,7 +751,7 @@ mod tests {
     maybe_temp_dir: Option<TempDir>,
   ) -> (FileFetcher, TempDir, Arc<BlobStore>) {
     let temp_dir = maybe_temp_dir.unwrap_or_default();
-    let location = temp_dir.path().join("deps").to_path_buf();
+    let location = temp_dir.path().join("remote").to_path_buf();
     let blob_store: Arc<BlobStore> = Default::default();
     let file_fetcher = FileFetcher::new(
       Arc::new(GlobalHttpCache::new(location, RealDenoCacheEnv)),
@@ -756,6 +781,7 @@ mod tests {
         FetchOptions {
           specifier,
           permissions: FetchPermissionsOptionRef::AllowAll,
+          maybe_auth: None,
           maybe_accept: None,
           maybe_cache_setting: Some(&file_fetcher.cache_setting),
         },
@@ -964,7 +990,7 @@ mod tests {
 
     // This creates a totally new instance, simulating another Deno process
     // invocation and indicates to "cache bust".
-    let location = temp_dir.path().join("deps").to_path_buf();
+    let location = temp_dir.path().join("remote").to_path_buf();
     let file_fetcher = FileFetcher::new(
       Arc::new(GlobalHttpCache::new(
         location,
@@ -990,7 +1016,7 @@ mod tests {
   async fn test_fetch_uses_cache() {
     let _http_server_guard = test_util::http_server();
     let temp_dir = TempDir::new();
-    let location = temp_dir.path().join("deps").to_path_buf();
+    let location = temp_dir.path().join("remote").to_path_buf();
     let specifier =
       resolve_url("http://localhost:4545/subdir/mismatch_ext.ts").unwrap();
 
@@ -1156,7 +1182,7 @@ mod tests {
   async fn test_fetch_uses_cache_with_redirects() {
     let _http_server_guard = test_util::http_server();
     let temp_dir = TempDir::new();
-    let location = temp_dir.path().join("deps").to_path_buf();
+    let location = temp_dir.path().join("remote").to_path_buf();
     let specifier =
       resolve_url("http://localhost:4548/subdir/mismatch_ext.ts").unwrap();
     let redirected_specifier =
@@ -1255,6 +1281,7 @@ mod tests {
         FetchOptions {
           specifier: &specifier,
           permissions: FetchPermissionsOptionRef::AllowAll,
+          maybe_auth: None,
           maybe_accept: None,
           maybe_cache_setting: Some(&file_fetcher.cache_setting),
         },
@@ -1268,6 +1295,7 @@ mod tests {
         FetchOptions {
           specifier: &specifier,
           permissions: FetchPermissionsOptionRef::AllowAll,
+          maybe_auth: None,
           maybe_accept: None,
           maybe_cache_setting: Some(&file_fetcher.cache_setting),
         },
@@ -1324,7 +1352,7 @@ mod tests {
   async fn test_fetch_no_remote() {
     let _http_server_guard = test_util::http_server();
     let temp_dir = TempDir::new();
-    let location = temp_dir.path().join("deps").to_path_buf();
+    let location = temp_dir.path().join("remote").to_path_buf();
     let file_fetcher = FileFetcher::new(
       Arc::new(GlobalHttpCache::new(
         location,
@@ -1350,7 +1378,7 @@ mod tests {
   async fn test_fetch_cache_only() {
     let _http_server_guard = test_util::http_server();
     let temp_dir = TempDir::new();
-    let location = temp_dir.path().join("deps").to_path_buf();
+    let location = temp_dir.path().join("remote").to_path_buf();
     let file_fetcher_01 = FileFetcher::new(
       Arc::new(GlobalHttpCache::new(location.clone(), RealDenoCacheEnv)),
       CacheSetting::Only,
diff --git a/cli/graph_util.rs b/cli/graph_util.rs
index 17f7d6739f..6ed0506dd7 100644
--- a/cli/graph_util.rs
+++ b/cli/graph_util.rs
@@ -13,14 +13,19 @@ use crate::colors;
 use crate::errors::get_error_class_name;
 use crate::file_fetcher::FileFetcher;
 use crate::npm::CliNpmResolver;
-use crate::resolver::CliGraphResolver;
-use crate::resolver::SloppyImportsResolver;
+use crate::resolver::CjsTracker;
+use crate::resolver::CliResolver;
+use crate::resolver::CliSloppyImportsResolver;
+use crate::resolver::SloppyImportsCachedFs;
 use crate::tools::check;
 use crate::tools::check::TypeChecker;
 use crate::util::file_watcher::WatcherCommunicator;
 use crate::util::fs::canonicalize_path;
+use deno_config::deno_json::JsxImportSourceConfig;
 use deno_config::workspace::JsrPackageConfig;
+use deno_core::anyhow::bail;
 use deno_graph::source::LoaderChecksum;
+use deno_graph::source::ResolutionMode;
 use deno_graph::FillFromLockfileOptions;
 use deno_graph::JsrLoadError;
 use deno_graph::ModuleLoadError;
@@ -31,7 +36,6 @@ use deno_core::error::AnyError;
 use deno_core::parking_lot::Mutex;
 use deno_core::ModuleSpecifier;
 use deno_graph::source::Loader;
-use deno_graph::source::ResolutionMode;
 use deno_graph::source::ResolveError;
 use deno_graph::GraphKind;
 use deno_graph::ModuleError;
@@ -39,13 +43,15 @@ use deno_graph::ModuleGraph;
 use deno_graph::ModuleGraphError;
 use deno_graph::ResolutionError;
 use deno_graph::SpecifierError;
+use deno_path_util::url_to_file_path;
+use deno_resolver::sloppy_imports::SloppyImportsResolutionMode;
 use deno_runtime::deno_fs::FileSystem;
 use deno_runtime::deno_node;
 use deno_runtime::deno_permissions::PermissionsContainer;
-use deno_runtime::fs_util::specifier_to_file_path;
 use deno_semver::jsr::JsrDepPackageReq;
 use deno_semver::package::PackageNv;
 use import_map::ImportMapError;
+use node_resolver::InNpmPackageChecker;
 use std::collections::HashSet;
 use std::error::Error;
 use std::ops::Deref;
@@ -182,7 +188,7 @@ pub fn graph_exit_integrity_errors(graph: &ModuleGraph) {
 fn exit_for_integrity_error(err: &ModuleError) {
   if let Some(err_message) = enhanced_integrity_error_message(err) {
     log::error!("{} {}", colors::red("error:"), err_message);
-    std::process::exit(10);
+    deno_runtime::exit(10);
   }
 }
 
@@ -375,48 +381,54 @@ pub struct BuildFastCheckGraphOptions<'a> {
 }
 
 pub struct ModuleGraphBuilder {
-  options: Arc<CliOptions>,
   caches: Arc<cache::Caches>,
+  cjs_tracker: Arc<CjsTracker>,
+  cli_options: Arc<CliOptions>,
+  file_fetcher: Arc<FileFetcher>,
   fs: Arc<dyn FileSystem>,
-  resolver: Arc<CliGraphResolver>,
-  npm_resolver: Arc<dyn CliNpmResolver>,
-  module_info_cache: Arc<ModuleInfoCache>,
-  parsed_source_cache: Arc<ParsedSourceCache>,
+  global_http_cache: Arc<GlobalHttpCache>,
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
   lockfile: Option<Arc<CliLockfile>>,
   maybe_file_watcher_reporter: Option<FileWatcherReporter>,
-  file_fetcher: Arc<FileFetcher>,
-  global_http_cache: Arc<GlobalHttpCache>,
+  module_info_cache: Arc<ModuleInfoCache>,
+  npm_resolver: Arc<dyn CliNpmResolver>,
+  parsed_source_cache: Arc<ParsedSourceCache>,
+  resolver: Arc<CliResolver>,
   root_permissions_container: PermissionsContainer,
 }
 
 impl ModuleGraphBuilder {
   #[allow(clippy::too_many_arguments)]
   pub fn new(
-    options: Arc<CliOptions>,
     caches: Arc<cache::Caches>,
+    cjs_tracker: Arc<CjsTracker>,
+    cli_options: Arc<CliOptions>,
+    file_fetcher: Arc<FileFetcher>,
     fs: Arc<dyn FileSystem>,
-    resolver: Arc<CliGraphResolver>,
-    npm_resolver: Arc<dyn CliNpmResolver>,
-    module_info_cache: Arc<ModuleInfoCache>,
-    parsed_source_cache: Arc<ParsedSourceCache>,
+    global_http_cache: Arc<GlobalHttpCache>,
+    in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
     lockfile: Option<Arc<CliLockfile>>,
     maybe_file_watcher_reporter: Option<FileWatcherReporter>,
-    file_fetcher: Arc<FileFetcher>,
-    global_http_cache: Arc<GlobalHttpCache>,
+    module_info_cache: Arc<ModuleInfoCache>,
+    npm_resolver: Arc<dyn CliNpmResolver>,
+    parsed_source_cache: Arc<ParsedSourceCache>,
+    resolver: Arc<CliResolver>,
     root_permissions_container: PermissionsContainer,
   ) -> Self {
     Self {
-      options,
       caches,
+      cjs_tracker,
+      cli_options,
+      file_fetcher,
       fs,
-      resolver,
-      npm_resolver,
-      module_info_cache,
-      parsed_source_cache,
+      global_http_cache,
+      in_npm_pkg_checker,
       lockfile,
       maybe_file_watcher_reporter,
-      file_fetcher,
-      global_http_cache,
+      module_info_cache,
+      npm_resolver,
+      parsed_source_cache,
+      resolver,
       root_permissions_container,
     }
   }
@@ -502,19 +514,17 @@ impl ModuleGraphBuilder {
     }
 
     let maybe_imports = if options.graph_kind.include_types() {
-      self.options.to_compiler_option_types()?
+      self.cli_options.to_compiler_option_types()?
     } else {
       Vec::new()
     };
-    let analyzer = self
-      .module_info_cache
-      .as_module_analyzer(&self.parsed_source_cache);
+    let analyzer = self.module_info_cache.as_module_analyzer();
     let mut loader = match options.loader {
       Some(loader) => MutLoaderRef::Borrowed(loader),
       None => MutLoaderRef::Owned(self.create_graph_loader()),
     };
     let cli_resolver = &self.resolver;
-    let graph_resolver = cli_resolver.as_graph_resolver();
+    let graph_resolver = self.create_graph_resolver()?;
     let graph_npm_resolver = cli_resolver.create_graph_npm_resolver();
     let maybe_file_watcher_reporter = self
       .maybe_file_watcher_reporter
@@ -539,7 +549,7 @@ impl ModuleGraphBuilder {
           npm_resolver: Some(&graph_npm_resolver),
           module_analyzer: &analyzer,
           reporter: maybe_file_watcher_reporter,
-          resolver: Some(graph_resolver),
+          resolver: Some(&graph_resolver),
           locker: locker.as_mut().map(|l| l as _),
         },
       )
@@ -556,7 +566,7 @@ impl ModuleGraphBuilder {
     // ensure an "npm install" is done if the user has explicitly
     // opted into using a node_modules directory
     if self
-      .options
+      .cli_options
       .node_modules_dir()?
       .map(|m| m.uses_node_modules_dir())
       .unwrap_or(false)
@@ -592,6 +602,12 @@ impl ModuleGraphBuilder {
     let initial_package_deps_len = graph.packages.package_deps_sum();
     let initial_package_mappings_len = graph.packages.mappings().len();
 
+    if roots.iter().any(|r| r.scheme() == "npm")
+      && self.npm_resolver.as_byonm().is_some()
+    {
+      bail!("Resolving npm specifier entrypoints this way is currently not supported with \"nodeModules\": \"manual\". In the meantime, try with --node-modules-dir=auto instead");
+    }
+
     graph.build(roots, loader, options).await;
 
     let has_redirects_changed = graph.redirects.len() != initial_redirects_len;
@@ -656,16 +672,16 @@ impl ModuleGraphBuilder {
     };
     let parser = self.parsed_source_cache.as_capturing_parser();
     let cli_resolver = &self.resolver;
-    let graph_resolver = cli_resolver.as_graph_resolver();
+    let graph_resolver = self.create_graph_resolver()?;
     let graph_npm_resolver = cli_resolver.create_graph_npm_resolver();
 
     graph.build_fast_check_type_graph(
       deno_graph::BuildFastCheckTypeGraphOptions {
-        jsr_url_provider: &CliJsrUrlProvider,
+        es_parser: Some(&parser),
         fast_check_cache: fast_check_cache.as_ref().map(|c| c as _),
         fast_check_dts: false,
-        module_parser: Some(&parser),
-        resolver: Some(graph_resolver),
+        jsr_url_provider: &CliJsrUrlProvider,
+        resolver: Some(&graph_resolver),
         npm_resolver: Some(&graph_npm_resolver),
         workspace_fast_check: options.workspace_fast_check,
       },
@@ -684,14 +700,15 @@ impl ModuleGraphBuilder {
   ) -> cache::FetchCacher {
     cache::FetchCacher::new(
       self.file_fetcher.clone(),
+      self.fs.clone(),
       self.global_http_cache.clone(),
-      self.npm_resolver.clone(),
+      self.in_npm_pkg_checker.clone(),
       self.module_info_cache.clone(),
       cache::FetchCacherOptions {
-        file_header_overrides: self.options.resolve_file_header_overrides(),
+        file_header_overrides: self.cli_options.resolve_file_header_overrides(),
         permissions,
         is_deno_publish: matches!(
-          self.options.sub_command(),
+          self.cli_options.sub_command(),
           crate::args::DenoSubcommand::Publish { .. }
         ),
       },
@@ -718,16 +735,28 @@ impl ModuleGraphBuilder {
       &self.fs,
       roots,
       GraphValidOptions {
-        kind: if self.options.type_check_mode().is_true() {
+        kind: if self.cli_options.type_check_mode().is_true() {
           GraphKind::All
         } else {
           GraphKind::CodeOnly
         },
-        check_js: self.options.check_js(),
+        check_js: self.cli_options.check_js(),
         exit_integrity_errors: true,
       },
     )
   }
+
+  fn create_graph_resolver(&self) -> Result<CliGraphResolver, AnyError> {
+    let jsx_import_source_config = self
+      .cli_options
+      .workspace()
+      .to_maybe_jsx_import_source_config()?;
+    Ok(CliGraphResolver {
+      cjs_tracker: &self.cjs_tracker,
+      resolver: &self.resolver,
+      jsx_import_source_config,
+    })
+  }
 }
 
 /// Adds more explanatory information to a resolution error.
@@ -765,8 +794,8 @@ fn enhanced_sloppy_imports_error_message(
   match error {
     ModuleError::LoadingErr(specifier, _, ModuleLoadError::Loader(_)) // ex. "Is a directory" error
     | ModuleError::Missing(specifier, _) => {
-      let additional_message = SloppyImportsResolver::new(fs.clone())
-        .resolve(specifier, ResolutionMode::Execution)?
+      let additional_message = CliSloppyImportsResolver::new(SloppyImportsCachedFs::new(fs.clone()))
+        .resolve(specifier, SloppyImportsResolutionMode::Execution)?
         .as_suggestion_message();
       Some(format!(
         "{} {} or run with --unstable-sloppy-imports",
@@ -948,7 +977,7 @@ pub fn has_graph_root_local_dependent_changed(
     },
   );
   while let Some((s, _)) = dependent_specifiers.next() {
-    if let Ok(path) = specifier_to_file_path(s) {
+    if let Ok(path) = url_to_file_path(s) {
       if let Ok(path) = canonicalize_path(&path) {
         if canonicalized_changed_paths.contains(&path) {
           return true;
@@ -990,7 +1019,11 @@ impl deno_graph::source::Reporter for FileWatcherReporter {
   ) {
     let mut file_paths = self.file_paths.lock();
     if specifier.scheme() == "file" {
-      file_paths.push(specifier.to_file_path().unwrap());
+      // Don't trust that the path is a valid path at this point:
+      // https://github.com/denoland/deno/issues/26209.
+      if let Ok(file_path) = specifier.to_file_path() {
+        file_paths.push(file_path);
+      }
     }
 
     if modules_done == modules_total {
@@ -1128,6 +1161,53 @@ fn format_deno_graph_error(err: &dyn Error) -> String {
   message
 }
 
+#[derive(Debug)]
+struct CliGraphResolver<'a> {
+  cjs_tracker: &'a CjsTracker,
+  resolver: &'a CliResolver,
+  jsx_import_source_config: Option<JsxImportSourceConfig>,
+}
+
+impl<'a> deno_graph::source::Resolver for CliGraphResolver<'a> {
+  fn default_jsx_import_source(&self) -> Option<String> {
+    self
+      .jsx_import_source_config
+      .as_ref()
+      .and_then(|c| c.default_specifier.clone())
+  }
+
+  fn default_jsx_import_source_types(&self) -> Option<String> {
+    self
+      .jsx_import_source_config
+      .as_ref()
+      .and_then(|c| c.default_types_specifier.clone())
+  }
+
+  fn jsx_import_source_module(&self) -> &str {
+    self
+      .jsx_import_source_config
+      .as_ref()
+      .map(|c| c.module.as_str())
+      .unwrap_or(deno_graph::source::DEFAULT_JSX_IMPORT_SOURCE_MODULE)
+  }
+
+  fn resolve(
+    &self,
+    raw_specifier: &str,
+    referrer_range: &deno_graph::Range,
+    mode: ResolutionMode,
+  ) -> Result<ModuleSpecifier, ResolveError> {
+    self.resolver.resolve(
+      raw_specifier,
+      referrer_range,
+      self
+        .cjs_tracker
+        .get_referrer_kind(&referrer_range.specifier),
+      mode,
+    )
+  }
+}
+
 #[cfg(test)]
 mod test {
   use std::sync::Arc;
diff --git a/cli/http_util.rs b/cli/http_util.rs
index cf244c525a..4b17936d68 100644
--- a/cli/http_util.rs
+++ b/cli/http_util.rs
@@ -19,6 +19,7 @@ use deno_runtime::deno_fetch;
 use deno_runtime::deno_fetch::create_http_client;
 use deno_runtime::deno_fetch::CreateHttpClientOptions;
 use deno_runtime::deno_tls::RootCertStoreProvider;
+use http::header;
 use http::header::HeaderName;
 use http::header::HeaderValue;
 use http::header::ACCEPT;
@@ -204,6 +205,7 @@ pub struct FetchOnceArgs<'a> {
   pub maybe_accept: Option<String>,
   pub maybe_etag: Option<String>,
   pub maybe_auth_token: Option<AuthToken>,
+  pub maybe_auth: Option<(header::HeaderName, header::HeaderValue)>,
   pub maybe_progress_guard: Option<&'a UpdateGuard>,
 }
 
@@ -382,6 +384,8 @@ impl HttpClient {
       request
         .headers_mut()
         .insert(AUTHORIZATION, authorization_val);
+    } else if let Some((header, value)) = args.maybe_auth {
+      request.headers_mut().insert(header, value);
     }
     if let Some(accept) = args.maybe_accept {
       let accepts_val = HeaderValue::from_str(&accept)?;
@@ -470,15 +474,23 @@ impl HttpClient {
     }
   }
 
-  pub async fn download_with_progress(
+  pub async fn download_with_progress_and_retries(
     &self,
     url: Url,
     maybe_header: Option<(HeaderName, HeaderValue)>,
     progress_guard: &UpdateGuard,
   ) -> Result<Option<Vec<u8>>, DownloadError> {
-    self
-      .download_inner(url, maybe_header, Some(progress_guard))
-      .await
+    crate::util::retry::retry(
+      || {
+        self.download_inner(
+          url.clone(),
+          maybe_header.clone(),
+          Some(progress_guard),
+        )
+      },
+      |e| matches!(e, DownloadError::BadResponse(_) | DownloadError::Fetch(_)),
+    )
+    .await
   }
 
   pub async fn get_redirected_url(
@@ -784,6 +796,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Code(body, headers)) = result {
@@ -810,6 +823,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Code(body, headers)) = result {
@@ -837,6 +851,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Code(body, headers)) = result {
@@ -858,6 +873,7 @@ mod test {
         maybe_etag: Some("33a64df551425fcc55e".to_string()),
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     assert_eq!(res.unwrap(), FetchOnceResult::NotModified);
@@ -877,6 +893,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Code(body, headers)) = result {
@@ -906,6 +923,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Code(body, _)) = result {
@@ -931,6 +949,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Redirect(url, _)) = result {
@@ -966,6 +985,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Code(body, headers)) = result {
@@ -1013,6 +1033,7 @@ mod test {
           maybe_etag: None,
           maybe_auth_token: None,
           maybe_progress_guard: None,
+          maybe_auth: None,
         })
         .await;
 
@@ -1075,6 +1096,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
 
@@ -1128,6 +1150,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Code(body, headers)) = result {
@@ -1169,6 +1192,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Code(body, headers)) = result {
@@ -1191,6 +1215,7 @@ mod test {
         maybe_etag: Some("33a64df551425fcc55e".to_string()),
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     assert_eq!(res.unwrap(), FetchOnceResult::NotModified);
@@ -1225,6 +1250,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Code(body, headers)) = result {
@@ -1254,6 +1280,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     assert!(result.is_err());
@@ -1275,6 +1302,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
 
@@ -1298,6 +1326,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
 
diff --git a/cli/lsp/analysis.rs b/cli/lsp/analysis.rs
index fee9c86cbe..044b1573b9 100644
--- a/cli/lsp/analysis.rs
+++ b/cli/lsp/analysis.rs
@@ -2,6 +2,7 @@
 
 use super::diagnostics::DenoDiagnostic;
 use super::diagnostics::DiagnosticSource;
+use super::documents::Document;
 use super::documents::Documents;
 use super::language_server;
 use super::resolver::LspResolver;
@@ -9,13 +10,17 @@ use super::tsc;
 use super::urls::url_to_uri;
 
 use crate::args::jsr_url;
+use crate::lsp::logging::lsp_warn;
+use crate::lsp::search::PackageSearchApi;
 use crate::tools::lint::CliLinter;
+use crate::util::path::relative_specifier;
+use deno_config::workspace::MappedResolution;
+use deno_graph::source::ResolutionMode;
 use deno_lint::diagnostic::LintDiagnosticRange;
 
 use deno_ast::SourceRange;
 use deno_ast::SourceRangedForSpanned;
 use deno_ast::SourceTextInfo;
-use deno_core::anyhow::anyhow;
 use deno_core::error::custom_error;
 use deno_core::error::AnyError;
 use deno_core::serde::Deserialize;
@@ -23,8 +28,8 @@ use deno_core::serde::Serialize;
 use deno_core::serde_json;
 use deno_core::serde_json::json;
 use deno_core::ModuleSpecifier;
+use deno_path_util::url_to_file_path;
 use deno_runtime::deno_node::PathClean;
-use deno_runtime::fs_util::specifier_to_file_path;
 use deno_semver::jsr::JsrPackageNvReference;
 use deno_semver::jsr::JsrPackageReqReference;
 use deno_semver::npm::NpmPackageReqReference;
@@ -34,13 +39,15 @@ use deno_semver::package::PackageReq;
 use deno_semver::package::PackageReqReference;
 use deno_semver::Version;
 use import_map::ImportMap;
-use node_resolver::NpmResolver;
+use node_resolver::NodeModuleKind;
 use once_cell::sync::Lazy;
 use regex::Regex;
+use std::borrow::Cow;
 use std::cmp::Ordering;
 use std::collections::HashMap;
 use std::collections::HashSet;
 use std::path::Path;
+use text_lines::LineAndColumnIndex;
 use tower_lsp::lsp_types as lsp;
 use tower_lsp::lsp_types::Position;
 use tower_lsp::lsp_types::Range;
@@ -225,6 +232,8 @@ pub struct TsResponseImportMapper<'a> {
   documents: &'a Documents,
   maybe_import_map: Option<&'a ImportMap>,
   resolver: &'a LspResolver,
+  tsc_specifier_map: &'a tsc::TscSpecifierMap,
+  file_referrer: ModuleSpecifier,
 }
 
 impl<'a> TsResponseImportMapper<'a> {
@@ -232,11 +241,15 @@ impl<'a> TsResponseImportMapper<'a> {
     documents: &'a Documents,
     maybe_import_map: Option<&'a ImportMap>,
     resolver: &'a LspResolver,
+    tsc_specifier_map: &'a tsc::TscSpecifierMap,
+    file_referrer: &ModuleSpecifier,
   ) -> Self {
     Self {
       documents,
       maybe_import_map,
       resolver,
+      tsc_specifier_map,
+      file_referrer: file_referrer.clone(),
     }
   }
 
@@ -257,8 +270,6 @@ impl<'a> TsResponseImportMapper<'a> {
       }
     }
 
-    let file_referrer = self.documents.get_file_referrer(referrer);
-
     if let Some(jsr_path) = specifier.as_str().strip_prefix(jsr_url().as_str())
     {
       let mut segments = jsr_path.split('/');
@@ -273,7 +284,7 @@ impl<'a> TsResponseImportMapper<'a> {
       let export = self.resolver.jsr_lookup_export_for_path(
         &nv,
         &path,
-        file_referrer.as_deref(),
+        Some(&self.file_referrer),
       )?;
       let sub_path = (export != ".").then_some(export);
       let mut req = None;
@@ -299,7 +310,7 @@ impl<'a> TsResponseImportMapper<'a> {
       req = req.or_else(|| {
         self
           .resolver
-          .jsr_lookup_req_for_nv(&nv, file_referrer.as_deref())
+          .jsr_lookup_req_for_nv(&nv, Some(&self.file_referrer))
       });
       let spec_str = if let Some(req) = req {
         let req_ref = PackageReqReference { req, sub_path };
@@ -329,9 +340,13 @@ impl<'a> TsResponseImportMapper<'a> {
 
     if let Some(npm_resolver) = self
       .resolver
-      .maybe_managed_npm_resolver(file_referrer.as_deref())
+      .maybe_managed_npm_resolver(Some(&self.file_referrer))
     {
-      if npm_resolver.in_npm_package(specifier) {
+      let in_npm_pkg = self
+        .resolver
+        .in_npm_pkg_checker(Some(&self.file_referrer))
+        .in_npm_package(specifier);
+      if in_npm_pkg {
         if let Ok(Some(pkg_id)) =
           npm_resolver.resolve_pkg_id_from_specifier(specifier)
         {
@@ -378,6 +393,11 @@ impl<'a> TsResponseImportMapper<'a> {
           }
         }
       }
+    } else if let Some(dep_name) = self
+      .resolver
+      .file_url_to_package_json_dep(specifier, Some(&self.file_referrer))
+    {
+      return Some(dep_name);
     }
 
     // check if the import map has this specifier
@@ -401,7 +421,7 @@ impl<'a> TsResponseImportMapper<'a> {
       .flatten()?;
     let root_folder = package_json.path.parent()?;
 
-    let specifier_path = specifier_to_file_path(specifier).ok()?;
+    let specifier_path = url_to_file_path(specifier).ok()?;
     let mut search_paths = vec![specifier_path.clone()];
     // TypeScript will provide a .js extension for quick fixes, so do
     // a search for the .d.ts file instead
@@ -447,24 +467,65 @@ impl<'a> TsResponseImportMapper<'a> {
     &self,
     specifier: &str,
     referrer: &ModuleSpecifier,
+    referrer_kind: NodeModuleKind,
   ) -> Option<String> {
-    if let Ok(specifier) = referrer.join(specifier) {
-      if let Some(specifier) = self.check_specifier(&specifier, referrer) {
-        return Some(specifier);
-      }
-    }
-    let specifier = specifier.strip_suffix(".js").unwrap_or(specifier);
-    for ext in SUPPORTED_EXTENSIONS {
-      let specifier_with_ext = format!("{specifier}{ext}");
-      if self
-        .documents
-        .contains_import(&specifier_with_ext, referrer)
+    let specifier_stem = specifier.strip_suffix(".js").unwrap_or(specifier);
+    let specifiers = std::iter::once(Cow::Borrowed(specifier)).chain(
+      SUPPORTED_EXTENSIONS
+        .iter()
+        .map(|ext| Cow::Owned(format!("{specifier_stem}{ext}"))),
+    );
+    for specifier in specifiers {
+      if let Some(specifier) = self
+        .resolver
+        .as_cli_resolver(Some(&self.file_referrer))
+        .resolve(
+          &specifier,
+          &deno_graph::Range {
+            specifier: referrer.clone(),
+            start: deno_graph::Position::zeroed(),
+            end: deno_graph::Position::zeroed(),
+          },
+          referrer_kind,
+          ResolutionMode::Types,
+        )
+        .ok()
+        .and_then(|s| self.tsc_specifier_map.normalize(s.as_str()).ok())
+        .filter(|s| self.documents.exists(s, Some(&self.file_referrer)))
       {
-        return Some(specifier_with_ext);
+        if let Some(specifier) = self
+          .check_specifier(&specifier, referrer)
+          .or_else(|| relative_specifier(referrer, &specifier))
+          .filter(|s| !s.contains("/node_modules/"))
+        {
+          return Some(specifier);
+        }
       }
     }
     None
   }
+
+  pub fn is_valid_import(
+    &self,
+    specifier_text: &str,
+    referrer: &ModuleSpecifier,
+    referrer_kind: NodeModuleKind,
+  ) -> bool {
+    self
+      .resolver
+      .as_cli_resolver(Some(&self.file_referrer))
+      .resolve(
+        specifier_text,
+        &deno_graph::Range {
+          specifier: referrer.clone(),
+          start: deno_graph::Position::zeroed(),
+          end: deno_graph::Position::zeroed(),
+        },
+        referrer_kind,
+        deno_graph::source::ResolutionMode::Types,
+      )
+      .is_ok()
+  }
 }
 
 fn try_reverse_map_package_json_exports(
@@ -529,9 +590,11 @@ fn try_reverse_map_package_json_exports(
 /// like an import and rewrite the import specifier to include the extension
 pub fn fix_ts_import_changes(
   referrer: &ModuleSpecifier,
+  referrer_kind: NodeModuleKind,
   changes: &[tsc::FileTextChanges],
-  import_mapper: &TsResponseImportMapper,
+  language_server: &language_server::Inner,
 ) -> Result<Vec<tsc::FileTextChanges>, AnyError> {
+  let import_mapper = language_server.get_ts_response_import_mapper(referrer);
   let mut r = Vec::new();
   for change in changes {
     let mut text_changes = Vec::new();
@@ -544,8 +607,8 @@ pub fn fix_ts_import_changes(
           if let Some(captures) = IMPORT_SPECIFIER_RE.captures(line) {
             let specifier =
               captures.iter().skip(1).find_map(|s| s).unwrap().as_str();
-            if let Some(new_specifier) =
-              import_mapper.check_unresolved_specifier(specifier, referrer)
+            if let Some(new_specifier) = import_mapper
+              .check_unresolved_specifier(specifier, referrer, referrer_kind)
             {
               line.replace(specifier, &new_specifier)
             } else {
@@ -573,66 +636,64 @@ pub fn fix_ts_import_changes(
 
 /// Fix tsc import code actions so that the module specifier is correct for
 /// resolution by Deno (includes the extension).
-fn fix_ts_import_action(
+fn fix_ts_import_action<'a>(
   referrer: &ModuleSpecifier,
-  action: &tsc::CodeFixAction,
-  import_mapper: &TsResponseImportMapper,
-) -> Result<tsc::CodeFixAction, AnyError> {
-  if matches!(
+  referrer_kind: NodeModuleKind,
+  action: &'a tsc::CodeFixAction,
+  language_server: &language_server::Inner,
+) -> Option<Cow<'a, tsc::CodeFixAction>> {
+  if !matches!(
     action.fix_name.as_str(),
     "import" | "fixMissingFunctionDeclaration"
   ) {
-    let change = action
+    return Some(Cow::Borrowed(action));
+  }
+  let specifier = (|| {
+    let text_change = action.changes.first()?.text_changes.first()?;
+    let captures = IMPORT_SPECIFIER_RE.captures(&text_change.new_text)?;
+    Some(captures.get(1)?.as_str())
+  })();
+  let Some(specifier) = specifier else {
+    return Some(Cow::Borrowed(action));
+  };
+  let import_mapper = language_server.get_ts_response_import_mapper(referrer);
+  if let Some(new_specifier) =
+    import_mapper.check_unresolved_specifier(specifier, referrer, referrer_kind)
+  {
+    let description = action.description.replace(specifier, &new_specifier);
+    let changes = action
       .changes
-      .first()
-      .ok_or_else(|| anyhow!("Unexpected action changes."))?;
-    let text_change = change
-      .text_changes
-      .first()
-      .ok_or_else(|| anyhow!("Missing text change."))?;
-    if let Some(captures) = IMPORT_SPECIFIER_RE.captures(&text_change.new_text)
-    {
-      let specifier = captures
-        .get(1)
-        .ok_or_else(|| anyhow!("Missing capture."))?
-        .as_str();
-      if let Some(new_specifier) =
-        import_mapper.check_unresolved_specifier(specifier, referrer)
-      {
-        let description = action.description.replace(specifier, &new_specifier);
-        let changes = action
-          .changes
+      .iter()
+      .map(|c| {
+        let text_changes = c
+          .text_changes
           .iter()
-          .map(|c| {
-            let text_changes = c
-              .text_changes
-              .iter()
-              .map(|tc| tsc::TextChange {
-                span: tc.span.clone(),
-                new_text: tc.new_text.replace(specifier, &new_specifier),
-              })
-              .collect();
-            tsc::FileTextChanges {
-              file_name: c.file_name.clone(),
-              text_changes,
-              is_new_file: c.is_new_file,
-            }
+          .map(|tc| tsc::TextChange {
+            span: tc.span.clone(),
+            new_text: tc.new_text.replace(specifier, &new_specifier),
           })
           .collect();
+        tsc::FileTextChanges {
+          file_name: c.file_name.clone(),
+          text_changes,
+          is_new_file: c.is_new_file,
+        }
+      })
+      .collect();
 
-        return Ok(tsc::CodeFixAction {
-          description,
-          changes,
-          commands: None,
-          fix_name: action.fix_name.clone(),
-          fix_id: None,
-          fix_all_description: None,
-        });
-      }
-    }
+    Some(Cow::Owned(tsc::CodeFixAction {
+      description,
+      changes,
+      commands: None,
+      fix_name: action.fix_name.clone(),
+      fix_id: None,
+      fix_all_description: None,
+    }))
+  } else if !import_mapper.is_valid_import(specifier, referrer, referrer_kind) {
+    None
+  } else {
+    Some(Cow::Borrowed(action))
   }
-
-  Ok(action.clone())
 }
 
 /// Determines if two TypeScript diagnostic codes are effectively equivalent.
@@ -693,8 +754,14 @@ pub fn ts_changes_to_edit(
 ) -> Result<Option<lsp::WorkspaceEdit>, AnyError> {
   let mut text_document_edits = Vec::new();
   for change in changes {
-    let text_document_edit = change.to_text_document_edit(language_server)?;
-    text_document_edits.push(text_document_edit);
+    let edit = match change.to_text_document_edit(language_server) {
+      Ok(e) => e,
+      Err(err) => {
+        lsp_warn!("Couldn't covert text document edit: {:#}", err);
+        continue;
+      }
+    };
+    text_document_edits.push(edit);
   }
   Ok(Some(lsp::WorkspaceEdit {
     changes: None,
@@ -703,7 +770,7 @@ pub fn ts_changes_to_edit(
   }))
 }
 
-#[derive(Debug, Deserialize)]
+#[derive(Debug, Deserialize, Serialize)]
 #[serde(rename_all = "camelCase")]
 pub struct CodeActionData {
   pub specifier: ModuleSpecifier,
@@ -956,6 +1023,7 @@ impl CodeActionCollection {
   pub fn add_ts_fix_action(
     &mut self,
     specifier: &ModuleSpecifier,
+    specifier_kind: NodeModuleKind,
     action: &tsc::CodeFixAction,
     diagnostic: &lsp::Diagnostic,
     language_server: &language_server::Inner,
@@ -973,11 +1041,11 @@ impl CodeActionCollection {
         "The action returned from TypeScript is unsupported.",
       ));
     }
-    let action = fix_ts_import_action(
-      specifier,
-      action,
-      &language_server.get_ts_response_import_mapper(specifier),
-    )?;
+    let Some(action) =
+      fix_ts_import_action(specifier, specifier_kind, action, language_server)
+    else {
+      return Ok(());
+    };
     let edit = ts_changes_to_edit(&action.changes, language_server)?;
     let code_action = lsp::CodeAction {
       title: action.description.clone(),
@@ -997,7 +1065,7 @@ impl CodeActionCollection {
     });
     self
       .actions
-      .push(CodeActionKind::Tsc(code_action, action.clone()));
+      .push(CodeActionKind::Tsc(code_action, action.as_ref().clone()));
 
     if let Some(fix_id) = &action.fix_id {
       if let Some(CodeActionKind::Tsc(existing_fix_all, existing_action)) =
@@ -1024,10 +1092,12 @@ impl CodeActionCollection {
     specifier: &ModuleSpecifier,
     diagnostic: &lsp::Diagnostic,
   ) {
-    let data = Some(json!({
-      "specifier": specifier,
-      "fixId": action.fix_id,
-    }));
+    let data = action.fix_id.as_ref().map(|fix_id| {
+      json!(CodeActionData {
+        specifier: specifier.clone(),
+        fix_id: fix_id.clone(),
+      })
+    });
     let title = if let Some(description) = &action.fix_all_description {
       description.clone()
     } else {
@@ -1151,6 +1221,192 @@ impl CodeActionCollection {
       ..Default::default()
     }));
   }
+
+  pub async fn add_source_actions(
+    &mut self,
+    document: &Document,
+    range: &lsp::Range,
+    language_server: &language_server::Inner,
+  ) {
+    fn import_start_from_specifier(
+      document: &Document,
+      import: &deno_graph::Import,
+    ) -> Option<LineAndColumnIndex> {
+      // find the top level statement that contains the specifier
+      let parsed_source = document.maybe_parsed_source()?.as_ref().ok()?;
+      let text_info = parsed_source.text_info_lazy();
+      let specifier_range = SourceRange::new(
+        text_info.loc_to_source_pos(LineAndColumnIndex {
+          line_index: import.specifier_range.start.line,
+          column_index: import.specifier_range.start.character,
+        }),
+        text_info.loc_to_source_pos(LineAndColumnIndex {
+          line_index: import.specifier_range.end.line,
+          column_index: import.specifier_range.end.character,
+        }),
+      );
+
+      parsed_source
+        .program_ref()
+        .body()
+        .find(|i| i.range().contains(&specifier_range))
+        .map(|i| text_info.line_and_column_index(i.range().start))
+    }
+
+    async fn deno_types_for_npm_action(
+      document: &Document,
+      range: &lsp::Range,
+      language_server: &language_server::Inner,
+    ) -> Option<lsp::CodeAction> {
+      let (dep_key, dependency, _) =
+        document.get_maybe_dependency(&range.end)?;
+      if dependency.maybe_deno_types_specifier.is_some() {
+        return None;
+      }
+      if dependency.maybe_code.maybe_specifier().is_none()
+        && dependency.maybe_type.maybe_specifier().is_none()
+      {
+        // We're using byonm and the package is not cached.
+        return None;
+      }
+      let position = deno_graph::Position::new(
+        range.end.line as usize,
+        range.end.character as usize,
+      );
+      let import_start = dependency.imports.iter().find_map(|i| {
+        if json!(i.kind) != json!("es") && json!(i.kind) != json!("tsType") {
+          return None;
+        }
+        if !i.specifier_range.includes(&position) {
+          return None;
+        }
+
+        import_start_from_specifier(document, i)
+      })?;
+      let referrer = document.specifier();
+      let referrer_kind = language_server
+        .is_cjs_resolver
+        .get_doc_module_kind(document);
+      let file_referrer = document.file_referrer();
+      let config_data = language_server
+        .config
+        .tree
+        .data_for_specifier(file_referrer?)?;
+      let workspace_resolver = config_data.resolver.clone();
+      let npm_ref = if let Ok(resolution) =
+        workspace_resolver.resolve(&dep_key, document.specifier())
+      {
+        let specifier = match resolution {
+          MappedResolution::Normal { specifier, .. }
+          | MappedResolution::ImportMap { specifier, .. } => specifier,
+          _ => {
+            return None;
+          }
+        };
+        NpmPackageReqReference::from_specifier(&specifier).ok()?
+      } else {
+        // Only resolve bare package.json deps for byonm.
+        if !config_data.byonm {
+          return None;
+        }
+        if !language_server.resolver.is_bare_package_json_dep(
+          &dep_key,
+          referrer,
+          referrer_kind,
+        ) {
+          return None;
+        }
+        NpmPackageReqReference::from_str(&format!("npm:{}", &dep_key)).ok()?
+      };
+      let package_name = &npm_ref.req().name;
+      if package_name.starts_with("@types/") {
+        return None;
+      }
+      let managed_npm_resolver = language_server
+        .resolver
+        .maybe_managed_npm_resolver(file_referrer);
+      if let Some(npm_resolver) = managed_npm_resolver {
+        if !npm_resolver.is_pkg_req_folder_cached(npm_ref.req()) {
+          return None;
+        }
+      }
+      if language_server
+        .resolver
+        .npm_to_file_url(&npm_ref, referrer, referrer_kind, file_referrer)
+        .is_some()
+      {
+        // The package import has types.
+        return None;
+      }
+      let types_package_name = format!("@types/{package_name}");
+      let types_package_version = language_server
+        .npm_search_api
+        .versions(&types_package_name)
+        .await
+        .ok()
+        .and_then(|versions| versions.first().cloned())?;
+      let types_specifier_text =
+        if let Some(npm_resolver) = managed_npm_resolver {
+          let mut specifier_text = if let Some(req) =
+            npm_resolver.top_package_req_for_name(&types_package_name)
+          {
+            format!("npm:{req}")
+          } else {
+            format!("npm:{}@^{}", &types_package_name, types_package_version)
+          };
+          let specifier = ModuleSpecifier::parse(&specifier_text).ok()?;
+          if let Some(file_referrer) = file_referrer {
+            if let Some(text) = language_server
+              .get_ts_response_import_mapper(file_referrer)
+              .check_specifier(&specifier, referrer)
+            {
+              specifier_text = text;
+            }
+          }
+          specifier_text
+        } else {
+          types_package_name.clone()
+        };
+      let uri = language_server
+        .url_map
+        .specifier_to_uri(referrer, file_referrer)
+        .ok()?;
+      let position = lsp::Position {
+        line: import_start.line_index as u32,
+        character: import_start.column_index as u32,
+      };
+      let new_text = format!(
+        "{}// @deno-types=\"{}\"\n",
+        if position.character == 0 { "" } else { "\n" },
+        &types_specifier_text
+      );
+      let text_edit = lsp::TextEdit {
+        range: lsp::Range {
+          start: position,
+          end: position,
+        },
+        new_text,
+      };
+      Some(lsp::CodeAction {
+        title: format!(
+          "Add @deno-types directive for \"{}\"",
+          &types_specifier_text
+        ),
+        kind: Some(lsp::CodeActionKind::QUICKFIX),
+        diagnostics: None,
+        edit: Some(lsp::WorkspaceEdit {
+          changes: Some([(uri, vec![text_edit])].into_iter().collect()),
+          ..Default::default()
+        }),
+        ..Default::default()
+      })
+    }
+    if let Some(action) =
+      deno_types_for_npm_action(document, range, language_server).await
+    {
+      self.actions.push(CodeActionKind::Deno(action));
+    }
+  }
 }
 
 /// Prepend the whitespace characters found at the start of line_content to content.
diff --git a/cli/lsp/cache.rs b/cli/lsp/cache.rs
index a32087842d..fbf9ea6f1b 100644
--- a/cli/lsp/cache.rs
+++ b/cli/lsp/cache.rs
@@ -10,7 +10,7 @@ use crate::lsp::logging::lsp_warn;
 
 use deno_core::url::Url;
 use deno_core::ModuleSpecifier;
-use deno_runtime::fs_util::specifier_to_file_path;
+use deno_path_util::url_to_file_path;
 use std::collections::BTreeMap;
 use std::fs;
 use std::path::Path;
@@ -24,7 +24,7 @@ pub fn calculate_fs_version(
 ) -> Option<String> {
   match specifier.scheme() {
     "npm" | "node" | "data" | "blob" => None,
-    "file" => specifier_to_file_path(specifier)
+    "file" => url_to_file_path(specifier)
       .ok()
       .and_then(|path| calculate_fs_version_at_path(&path)),
     _ => calculate_fs_version_in_cache(cache, specifier, file_referrer),
@@ -82,7 +82,7 @@ impl Default for LspCache {
 impl LspCache {
   pub fn new(global_cache_url: Option<Url>) -> Self {
     let global_cache_path = global_cache_url.and_then(|s| {
-      specifier_to_file_path(&s)
+      url_to_file_path(&s)
         .inspect(|p| {
           lsp_log!("Resolved global cache path: \"{}\"", p.to_string_lossy());
         })
@@ -94,7 +94,7 @@ impl LspCache {
     let deno_dir = DenoDir::new(global_cache_path)
       .expect("should be infallible with absolute custom root");
     let global = Arc::new(GlobalHttpCache::new(
-      deno_dir.deps_folder_path(),
+      deno_dir.remote_folder_path(),
       crate::cache::RealDenoCacheEnv,
     ));
     Self {
@@ -165,7 +165,7 @@ impl LspCache {
     &self,
     specifier: &ModuleSpecifier,
   ) -> Option<ModuleSpecifier> {
-    let path = specifier_to_file_path(specifier).ok()?;
+    let path = url_to_file_path(specifier).ok()?;
     let vendor = self
       .vendors_by_scope
       .iter()
@@ -176,7 +176,7 @@ impl LspCache {
   }
 
   pub fn is_valid_file_referrer(&self, specifier: &ModuleSpecifier) -> bool {
-    if let Ok(path) = specifier_to_file_path(specifier) {
+    if let Ok(path) = url_to_file_path(specifier) {
       if !path.starts_with(&self.deno_dir().root) {
         return true;
       }
diff --git a/cli/lsp/capabilities.rs b/cli/lsp/capabilities.rs
index e93d3b7c20..5cdb1224d8 100644
--- a/cli/lsp/capabilities.rs
+++ b/cli/lsp/capabilities.rs
@@ -147,11 +147,11 @@ pub fn server_capabilities(
     moniker_provider: None,
     experimental: Some(json!({
       "denoConfigTasks": true,
-      "testingApi":true,
+      "testingApi": true,
+      "didRefreshDenoConfigurationTreeNotifications": true,
     })),
     inlay_hint_provider: Some(OneOf::Left(true)),
     position_encoding: None,
-    // TODO(nayeemrmn): Support pull-based diagnostics.
     diagnostic_provider: None,
     inline_value_provider: None,
     inline_completion_provider: None,
diff --git a/cli/lsp/client.rs b/cli/lsp/client.rs
index b3f0d64fa6..65865d5b32 100644
--- a/cli/lsp/client.rs
+++ b/cli/lsp/client.rs
@@ -92,6 +92,19 @@ impl Client {
     });
   }
 
+  pub fn send_did_refresh_deno_configuration_tree_notification(
+    &self,
+    params: lsp_custom::DidRefreshDenoConfigurationTreeNotificationParams,
+  ) {
+    // do on a task in case the caller currently is in the lsp lock
+    let client = self.0.clone();
+    spawn(async move {
+      client
+        .send_did_refresh_deno_configuration_tree_notification(params)
+        .await;
+    });
+  }
+
   pub fn send_did_change_deno_configuration_notification(
     &self,
     params: lsp_custom::DidChangeDenoConfigurationNotificationParams,
@@ -169,6 +182,10 @@ trait ClientTrait: Send + Sync {
     params: lsp_custom::DiagnosticBatchNotificationParams,
   );
   async fn send_test_notification(&self, params: TestingNotification);
+  async fn send_did_refresh_deno_configuration_tree_notification(
+    &self,
+    params: lsp_custom::DidRefreshDenoConfigurationTreeNotificationParams,
+  );
   async fn send_did_change_deno_configuration_notification(
     &self,
     params: lsp_custom::DidChangeDenoConfigurationNotificationParams,
@@ -249,6 +266,18 @@ impl ClientTrait for TowerClient {
     }
   }
 
+  async fn send_did_refresh_deno_configuration_tree_notification(
+    &self,
+    params: lsp_custom::DidRefreshDenoConfigurationTreeNotificationParams,
+  ) {
+    self
+      .0
+      .send_notification::<lsp_custom::DidRefreshDenoConfigurationTreeNotification>(
+        params,
+      )
+      .await
+  }
+
   async fn send_did_change_deno_configuration_notification(
     &self,
     params: lsp_custom::DidChangeDenoConfigurationNotificationParams,
@@ -366,6 +395,12 @@ impl ClientTrait for ReplClient {
 
   async fn send_test_notification(&self, _params: TestingNotification) {}
 
+  async fn send_did_refresh_deno_configuration_tree_notification(
+    &self,
+    _params: lsp_custom::DidRefreshDenoConfigurationTreeNotificationParams,
+  ) {
+  }
+
   async fn send_did_change_deno_configuration_notification(
     &self,
     _params: lsp_custom::DidChangeDenoConfigurationNotificationParams,
diff --git a/cli/lsp/code_lens.rs b/cli/lsp/code_lens.rs
index e117888fba..a57ca3ac9f 100644
--- a/cli/lsp/code_lens.rs
+++ b/cli/lsp/code_lens.rs
@@ -421,7 +421,7 @@ pub fn collect_test(
 ) -> Result<Vec<lsp::CodeLens>, AnyError> {
   let mut collector =
     DenoTestCollector::new(specifier.clone(), parsed_source.clone());
-  parsed_source.module().visit_with(&mut collector);
+  parsed_source.program().visit_with(&mut collector);
   Ok(collector.take())
 }
 
@@ -581,7 +581,7 @@ mod tests {
     .unwrap();
     let mut collector =
       DenoTestCollector::new(specifier, parsed_module.clone());
-    parsed_module.module().visit_with(&mut collector);
+    parsed_module.program().visit_with(&mut collector);
     assert_eq!(
       collector.take(),
       vec![
diff --git a/cli/lsp/completions.rs b/cli/lsp/completions.rs
index b3d6fbbd04..3ee8ae93e4 100644
--- a/cli/lsp/completions.rs
+++ b/cli/lsp/completions.rs
@@ -9,6 +9,7 @@ use super::jsr::CliJsrSearchApi;
 use super::lsp_custom;
 use super::npm::CliNpmSearchApi;
 use super::registries::ModuleRegistry;
+use super::resolver::LspIsCjsResolver;
 use super::resolver::LspResolver;
 use super::search::PackageSearchApi;
 use super::tsc;
@@ -29,12 +30,13 @@ use deno_core::serde::Serialize;
 use deno_core::serde_json::json;
 use deno_core::url::Position;
 use deno_core::ModuleSpecifier;
-use deno_runtime::fs_util::specifier_to_file_path;
+use deno_path_util::url_to_file_path;
 use deno_semver::jsr::JsrPackageReqReference;
 use deno_semver::package::PackageNv;
 use import_map::ImportMap;
 use indexmap::IndexSet;
 use lsp_types::CompletionList;
+use node_resolver::NodeModuleKind;
 use once_cell::sync::Lazy;
 use regex::Regex;
 use tower_lsp::lsp_types as lsp;
@@ -159,15 +161,17 @@ pub async fn get_import_completions(
   jsr_search_api: &CliJsrSearchApi,
   npm_search_api: &CliNpmSearchApi,
   documents: &Documents,
+  is_cjs_resolver: &LspIsCjsResolver,
   resolver: &LspResolver,
   maybe_import_map: Option<&ImportMap>,
 ) -> Option<lsp::CompletionResponse> {
   let document = documents.get(specifier)?;
+  let specifier_kind = is_cjs_resolver.get_doc_module_kind(&document);
   let file_referrer = document.file_referrer();
   let (text, _, range) = document.get_maybe_dependency(position)?;
   let range = to_narrow_lsp_range(document.text_info(), &range);
   let resolved = resolver
-    .as_graph_resolver(file_referrer)
+    .as_cli_resolver(file_referrer)
     .resolve(
       &text,
       &Range {
@@ -175,6 +179,7 @@ pub async fn get_import_completions(
         start: deno_graph::Position::zeroed(),
         end: deno_graph::Position::zeroed(),
       },
+      specifier_kind,
       ResolutionMode::Execution,
     )
     .ok();
@@ -200,15 +205,11 @@ pub async fn get_import_completions(
   {
     // completions for import map specifiers
     Some(lsp::CompletionResponse::List(completion_list))
-  } else if text.starts_with("./")
-    || text.starts_with("../")
-    || text.starts_with('/')
+  } else if let Some(completion_list) =
+    get_local_completions(specifier, specifier_kind, &text, &range, resolver)
   {
     // completions for local relative modules
-    Some(lsp::CompletionResponse::List(CompletionList {
-      is_incomplete: false,
-      items: get_local_completions(specifier, &text, &range, resolver)?,
-    }))
+    Some(lsp::CompletionResponse::List(completion_list))
   } else if !text.is_empty() {
     // completion of modules from a module registry or cache
     check_auto_config_registry(
@@ -359,84 +360,86 @@ fn get_import_map_completions(
 
 /// Return local completions that are relative to the base specifier.
 fn get_local_completions(
-  base: &ModuleSpecifier,
+  referrer: &ModuleSpecifier,
+  referrer_kind: NodeModuleKind,
   text: &str,
   range: &lsp::Range,
   resolver: &LspResolver,
-) -> Option<Vec<lsp::CompletionItem>> {
-  if base.scheme() != "file" {
+) -> Option<CompletionList> {
+  if referrer.scheme() != "file" {
     return None;
   }
-  let parent = base.join(text).ok()?.join(".").ok()?;
+  let parent = &text[..text.char_indices().rfind(|(_, c)| *c == '/')?.0 + 1];
   let resolved_parent = resolver
-    .as_graph_resolver(Some(base))
+    .as_cli_resolver(Some(referrer))
     .resolve(
-      parent.as_str(),
+      parent,
       &Range {
-        specifier: base.clone(),
+        specifier: referrer.clone(),
         start: deno_graph::Position::zeroed(),
         end: deno_graph::Position::zeroed(),
       },
+      referrer_kind,
       ResolutionMode::Execution,
     )
     .ok()?;
-  let resolved_parent_path = specifier_to_file_path(&resolved_parent).ok()?;
-  let raw_parent =
-    &text[..text.char_indices().rfind(|(_, c)| *c == '/')?.0 + 1];
+  let resolved_parent_path = url_to_file_path(&resolved_parent).ok()?;
   if resolved_parent_path.is_dir() {
     let cwd = std::env::current_dir().ok()?;
-    let items = std::fs::read_dir(resolved_parent_path).ok()?;
-    Some(
-      items
-        .filter_map(|de| {
-          let de = de.ok()?;
-          let label = de.path().file_name()?.to_string_lossy().to_string();
-          let entry_specifier = resolve_path(de.path().to_str()?, &cwd).ok()?;
-          if entry_specifier == *base {
-            return None;
-          }
-          let full_text = format!("{raw_parent}{label}");
-          let text_edit = Some(lsp::CompletionTextEdit::Edit(lsp::TextEdit {
-            range: *range,
-            new_text: full_text.clone(),
-          }));
-          let filter_text = Some(full_text);
-          match de.file_type() {
-            Ok(file_type) if file_type.is_dir() => Some(lsp::CompletionItem {
-              label,
-              kind: Some(lsp::CompletionItemKind::FOLDER),
-              detail: Some("(local)".to_string()),
-              filter_text,
-              sort_text: Some("1".to_string()),
-              text_edit,
-              commit_characters: Some(
-                IMPORT_COMMIT_CHARS.iter().map(|&c| c.into()).collect(),
-              ),
-              ..Default::default()
-            }),
-            Ok(file_type) if file_type.is_file() => {
-              if is_importable_ext(&de.path()) {
-                Some(lsp::CompletionItem {
-                  label,
-                  kind: Some(lsp::CompletionItemKind::FILE),
-                  detail: Some("(local)".to_string()),
-                  filter_text,
-                  sort_text: Some("1".to_string()),
-                  text_edit,
-                  commit_characters: Some(
-                    IMPORT_COMMIT_CHARS.iter().map(|&c| c.into()).collect(),
-                  ),
-                  ..Default::default()
-                })
-              } else {
-                None
-              }
+    let entries = std::fs::read_dir(resolved_parent_path).ok()?;
+    let items = entries
+      .filter_map(|de| {
+        let de = de.ok()?;
+        let label = de.path().file_name()?.to_string_lossy().to_string();
+        let entry_specifier = resolve_path(de.path().to_str()?, &cwd).ok()?;
+        if entry_specifier == *referrer {
+          return None;
+        }
+        let full_text = format!("{parent}{label}");
+        let text_edit = Some(lsp::CompletionTextEdit::Edit(lsp::TextEdit {
+          range: *range,
+          new_text: full_text.clone(),
+        }));
+        let filter_text = Some(full_text);
+        match de.file_type() {
+          Ok(file_type) if file_type.is_dir() => Some(lsp::CompletionItem {
+            label,
+            kind: Some(lsp::CompletionItemKind::FOLDER),
+            detail: Some("(local)".to_string()),
+            filter_text,
+            sort_text: Some("1".to_string()),
+            text_edit,
+            commit_characters: Some(
+              IMPORT_COMMIT_CHARS.iter().map(|&c| c.into()).collect(),
+            ),
+            ..Default::default()
+          }),
+          Ok(file_type) if file_type.is_file() => {
+            if is_importable_ext(&de.path()) {
+              Some(lsp::CompletionItem {
+                label,
+                kind: Some(lsp::CompletionItemKind::FILE),
+                detail: Some("(local)".to_string()),
+                filter_text,
+                sort_text: Some("1".to_string()),
+                text_edit,
+                commit_characters: Some(
+                  IMPORT_COMMIT_CHARS.iter().map(|&c| c.into()).collect(),
+                ),
+                ..Default::default()
+              })
+            } else {
+              None
             }
-            _ => None,
           }
-        })
-        .collect(),
-    )
+          _ => None,
+        }
+      })
+      .collect();
+    Some(CompletionList {
+      is_incomplete: false,
+      items,
+    })
   } else {
     None
   }
@@ -909,6 +912,7 @@ mod tests {
       ModuleSpecifier::from_file_path(file_c).expect("could not create");
     let actual = get_local_completions(
       &specifier,
+      NodeModuleKind::Esm,
       "./",
       &lsp::Range {
         start: lsp::Position {
@@ -921,11 +925,11 @@ mod tests {
         },
       },
       &Default::default(),
-    );
-    assert!(actual.is_some());
-    let actual = actual.unwrap();
-    assert_eq!(actual.len(), 3);
-    for item in actual {
+    )
+    .unwrap();
+    assert!(!actual.is_incomplete);
+    assert_eq!(actual.items.len(), 3);
+    for item in actual.items {
       match item.text_edit {
         Some(lsp::CompletionTextEdit::Edit(text_edit)) => {
           assert!(["./b", "./f.mjs", "./g.json"]
diff --git a/cli/lsp/config.rs b/cli/lsp/config.rs
index e55e7b734d..ea77e36bcf 100644
--- a/cli/lsp/config.rs
+++ b/cli/lsp/config.rs
@@ -4,6 +4,7 @@ use deno_ast::MediaType;
 use deno_config::deno_json::DenoJsonCache;
 use deno_config::deno_json::FmtConfig;
 use deno_config::deno_json::FmtOptionsConfig;
+use deno_config::deno_json::JsxImportSourceConfig;
 use deno_config::deno_json::LintConfig;
 use deno_config::deno_json::NodeModulesDirMode;
 use deno_config::deno_json::TestConfig;
@@ -36,11 +37,12 @@ use deno_core::ModuleSpecifier;
 use deno_lint::linter::LintConfig as DenoLintConfig;
 use deno_npm::npm_rc::ResolvedNpmRc;
 use deno_package_json::PackageJsonCache;
+use deno_path_util::url_to_file_path;
 use deno_runtime::deno_node::PackageJson;
-use deno_runtime::fs_util::specifier_to_file_path;
 use indexmap::IndexSet;
 use lsp_types::ClientCapabilities;
 use std::collections::BTreeMap;
+use std::collections::BTreeSet;
 use std::collections::HashMap;
 use std::ops::Deref;
 use std::ops::DerefMut;
@@ -50,16 +52,20 @@ use std::sync::Arc;
 use tower_lsp::lsp_types as lsp;
 
 use super::logging::lsp_log;
+use super::lsp_custom;
+use super::urls::url_to_uri;
 use crate::args::discover_npmrc_from_workspace;
 use crate::args::has_flag_env_var;
 use crate::args::CliLockfile;
+use crate::args::CliLockfileReadFromPathOptions;
 use crate::args::ConfigFile;
 use crate::args::LintFlags;
 use crate::args::LintOptions;
 use crate::cache::FastInsecureHasher;
 use crate::file_fetcher::FileFetcher;
 use crate::lsp::logging::lsp_warn;
-use crate::resolver::SloppyImportsResolver;
+use crate::resolver::CliSloppyImportsResolver;
+use crate::resolver::SloppyImportsCachedFs;
 use crate::tools::lint::CliLinter;
 use crate::tools::lint::CliLinterOptions;
 use crate::tools::lint::LintRuleProvider;
@@ -435,6 +441,8 @@ pub struct LanguagePreferences {
   pub use_aliases_for_renames: bool,
   #[serde(default)]
   pub quote_style: QuoteStyle,
+  #[serde(default)]
+  pub prefer_type_only_auto_imports: bool,
 }
 
 impl Default for LanguagePreferences {
@@ -445,6 +453,7 @@ impl Default for LanguagePreferences {
       auto_import_file_exclude_patterns: vec![],
       use_aliases_for_renames: true,
       quote_style: Default::default(),
+      prefer_type_only_auto_imports: false,
     }
   }
 }
@@ -801,7 +810,7 @@ impl Settings {
   /// Returns `None` if the value should be deferred to the presence of a
   /// `deno.json` file.
   pub fn specifier_enabled(&self, specifier: &ModuleSpecifier) -> Option<bool> {
-    let Ok(path) = specifier_to_file_path(specifier) else {
+    let Ok(path) = url_to_file_path(specifier) else {
       // Non-file URLs are not disabled by these settings.
       return Some(true);
     };
@@ -810,7 +819,7 @@ impl Settings {
     let mut disable_paths = vec![];
     let mut enable_paths = None;
     if let Some(folder_uri) = folder_uri {
-      if let Ok(folder_path) = specifier_to_file_path(folder_uri) {
+      if let Ok(folder_path) = url_to_file_path(folder_uri) {
         disable_paths = settings
           .disable_paths
           .iter()
@@ -847,12 +856,12 @@ impl Settings {
     &self,
     specifier: &ModuleSpecifier,
   ) -> (&WorkspaceSettings, Option<&ModuleSpecifier>) {
-    let Ok(path) = specifier_to_file_path(specifier) else {
+    let Ok(path) = url_to_file_path(specifier) else {
       return (&self.unscoped, self.first_folder.as_ref());
     };
     for (folder_uri, settings) in self.by_workspace_folder.iter().rev() {
       if let Some(settings) = settings {
-        let Ok(folder_path) = specifier_to_file_path(folder_uri) else {
+        let Ok(folder_path) = url_to_file_path(folder_uri) else {
           continue;
         };
         if path.starts_with(folder_path) {
@@ -977,7 +986,7 @@ impl Config {
       | MediaType::Tsx => Some(&workspace_settings.typescript),
       MediaType::Json
       | MediaType::Wasm
-      | MediaType::TsBuildInfo
+      | MediaType::Css
       | MediaType::SourceMap
       | MediaType::Unknown => None,
     }
@@ -1181,8 +1190,9 @@ pub struct ConfigData {
   pub lockfile: Option<Arc<CliLockfile>>,
   pub npmrc: Option<Arc<ResolvedNpmRc>>,
   pub resolver: Arc<WorkspaceResolver>,
-  pub sloppy_imports_resolver: Option<Arc<SloppyImportsResolver>>,
+  pub sloppy_imports_resolver: Option<Arc<CliSloppyImportsResolver>>,
   pub import_map_from_settings: Option<ModuleSpecifier>,
+  pub unstable: BTreeSet<String>,
   watched_files: HashMap<ModuleSpecifier, ConfigWatchedFileType>,
 }
 
@@ -1580,13 +1590,22 @@ impl ConfigData {
           .join("\n")
       );
     }
+    let unstable = member_dir
+      .workspace
+      .unstable_features()
+      .iter()
+      .chain(settings.unstable.as_deref())
+      .cloned()
+      .collect::<BTreeSet<_>>();
     let unstable_sloppy_imports = std::env::var("DENO_UNSTABLE_SLOPPY_IMPORTS")
       .is_ok()
-      || member_dir.workspace.has_unstable("sloppy-imports");
+      || unstable.contains("sloppy-imports");
     let sloppy_imports_resolver = unstable_sloppy_imports.then(|| {
-      Arc::new(SloppyImportsResolver::new_without_stat_cache(Arc::new(
-        deno_runtime::deno_fs::RealFs,
-      )))
+      Arc::new(CliSloppyImportsResolver::new(
+        SloppyImportsCachedFs::new_without_stat_cache(Arc::new(
+          deno_runtime::deno_fs::RealFs,
+        )),
+      ))
     });
     let resolver = Arc::new(resolver);
     let lint_rule_provider = LintRuleProvider::new(
@@ -1621,6 +1640,7 @@ impl ConfigData {
       lockfile,
       npmrc,
       import_map_from_settings,
+      unstable,
       watched_files,
     }
   }
@@ -1635,6 +1655,17 @@ impl ConfigData {
     self.member_dir.maybe_pkg_json()
   }
 
+  pub fn maybe_jsx_import_source_config(
+    &self,
+  ) -> Option<JsxImportSourceConfig> {
+    self
+      .member_dir
+      .workspace
+      .to_maybe_jsx_import_source_config()
+      .ok()
+      .flatten()
+  }
+
   pub fn scope_contains_specifier(&self, specifier: &ModuleSpecifier) -> bool {
     specifier.as_str().starts_with(self.scope.as_str())
       || self
@@ -1712,14 +1743,14 @@ impl ConfigTree {
       .unwrap_or_else(|| Arc::new(FmtConfig::new_with_base(PathBuf::from("/"))))
   }
 
-  /// Returns (scope_uri, type).
+  /// Returns (scope_url, type).
   pub fn watched_file_type(
     &self,
     specifier: &ModuleSpecifier,
   ) -> Option<(&ModuleSpecifier, ConfigWatchedFileType)> {
-    for (scope_uri, data) in self.scopes.iter() {
+    for (scope_url, data) in self.scopes.iter() {
       if let Some(typ) = data.watched_files.get(specifier) {
-        return Some((scope_uri, *typ));
+        return Some((scope_url, *typ));
       }
     }
     None
@@ -1743,6 +1774,46 @@ impl ConfigTree {
       .any(|data| data.watched_files.contains_key(specifier))
   }
 
+  pub fn to_did_refresh_params(
+    &self,
+  ) -> lsp_custom::DidRefreshDenoConfigurationTreeNotificationParams {
+    let data = self
+      .scopes
+      .values()
+      .filter_map(|data| {
+        let workspace_root_scope_uri =
+          Some(data.member_dir.workspace.root_dir())
+            .filter(|s| *s != data.member_dir.dir_url())
+            .and_then(|s| url_to_uri(s).ok());
+        Some(lsp_custom::DenoConfigurationData {
+          scope_uri: url_to_uri(&data.scope).ok()?,
+          deno_json: data.maybe_deno_json().and_then(|c| {
+            if workspace_root_scope_uri.is_some()
+              && Some(&c.specifier)
+                == data
+                  .member_dir
+                  .workspace
+                  .root_deno_json()
+                  .map(|c| &c.specifier)
+            {
+              return None;
+            }
+            Some(lsp::TextDocumentIdentifier {
+              uri: url_to_uri(&c.specifier).ok()?,
+            })
+          }),
+          package_json: data.maybe_pkg_json().and_then(|p| {
+            Some(lsp::TextDocumentIdentifier {
+              uri: url_to_uri(&p.specifier()).ok()?,
+            })
+          }),
+          workspace_root_scope_uri,
+        })
+      })
+      .collect();
+    lsp_custom::DidRefreshDenoConfigurationTreeNotificationParams { data }
+  }
+
   pub async fn refresh(
     &mut self,
     settings: &Settings,
@@ -1767,7 +1838,7 @@ impl ConfigTree {
         let config_file_path = (|| {
           let config_setting = ws_settings.config.as_ref()?;
           let config_uri = folder_uri.join(config_setting).ok()?;
-          specifier_to_file_path(&config_uri).ok()
+          url_to_file_path(&config_uri).ok()
         })();
         if config_file_path.is_some() || ws_settings.import_map.is_some() {
           scopes.insert(
@@ -1844,7 +1915,7 @@ impl ConfigTree {
     let scope = config_file.specifier.join(".").unwrap();
     let json_text = serde_json::to_string(&config_file.json).unwrap();
     let test_fs = deno_runtime::deno_fs::InMemoryFs::default();
-    let config_path = specifier_to_file_path(&config_file.specifier).unwrap();
+    let config_path = url_to_file_path(&config_file.specifier).unwrap();
     test_fs.setup_text_files(vec![(
       config_path.to_string_lossy().to_string(),
       json_text,
@@ -1928,7 +1999,11 @@ fn resolve_lockfile_from_path(
   lockfile_path: PathBuf,
   frozen: bool,
 ) -> Option<CliLockfile> {
-  match CliLockfile::read_from_path(lockfile_path, frozen) {
+  match CliLockfile::read_from_path(CliLockfileReadFromPathOptions {
+    file_path: lockfile_path,
+    frozen,
+    skip_write: false,
+  }) {
     Ok(value) => {
       if value.filename.exists() {
         if let Ok(specifier) = ModuleSpecifier::from_file_path(&value.filename)
@@ -2201,6 +2276,7 @@ mod tests {
             auto_import_file_exclude_patterns: vec![],
             use_aliases_for_renames: true,
             quote_style: QuoteStyle::Auto,
+            prefer_type_only_auto_imports: false,
           },
           suggest: CompletionSettings {
             complete_function_calls: false,
@@ -2246,6 +2322,7 @@ mod tests {
             auto_import_file_exclude_patterns: vec![],
             use_aliases_for_renames: true,
             quote_style: QuoteStyle::Auto,
+            prefer_type_only_auto_imports: false,
           },
           suggest: CompletionSettings {
             complete_function_calls: false,
diff --git a/cli/lsp/diagnostics.rs b/cli/lsp/diagnostics.rs
index 1aebaf56fc..e4fb82e58d 100644
--- a/cli/lsp/diagnostics.rs
+++ b/cli/lsp/diagnostics.rs
@@ -19,8 +19,8 @@ use super::urls::LspUrlMap;
 use crate::graph_util;
 use crate::graph_util::enhanced_resolution_error_message;
 use crate::lsp::lsp_custom::DiagnosticBatchNotificationParams;
-use crate::resolver::SloppyImportsResolution;
-use crate::resolver::SloppyImportsResolver;
+use crate::resolver::CliSloppyImportsResolver;
+use crate::resolver::SloppyImportsCachedFs;
 use crate::tools::lint::CliLinter;
 use crate::tools::lint::CliLinterOptions;
 use crate::tools::lint::LintRuleProvider;
@@ -40,11 +40,12 @@ use deno_core::unsync::spawn_blocking;
 use deno_core::unsync::JoinHandle;
 use deno_core::url::Url;
 use deno_core::ModuleSpecifier;
-use deno_graph::source::ResolutionMode;
 use deno_graph::source::ResolveError;
 use deno_graph::Resolution;
 use deno_graph::ResolutionError;
 use deno_graph::SpecifierError;
+use deno_resolver::sloppy_imports::SloppyImportsResolution;
+use deno_resolver::sloppy_imports::SloppyImportsResolutionMode;
 use deno_runtime::deno_fs;
 use deno_runtime::deno_node;
 use deno_runtime::tokio_util::create_basic_runtime;
@@ -1263,7 +1264,9 @@ impl DenoDiagnostic {
       Self::NotInstalledJsr(pkg_req, specifier) => (lsp::DiagnosticSeverity::ERROR, format!("JSR package \"{pkg_req}\" is not installed or doesn't exist."), Some(json!({ "specifier": specifier }))),
       Self::NotInstalledNpm(pkg_req, specifier) => (lsp::DiagnosticSeverity::ERROR, format!("NPM package \"{pkg_req}\" is not installed or doesn't exist."), Some(json!({ "specifier": specifier }))),
       Self::NoLocal(specifier) => {
-        let maybe_sloppy_resolution = SloppyImportsResolver::new(Arc::new(deno_fs::RealFs)).resolve(specifier, ResolutionMode::Execution);
+        let maybe_sloppy_resolution = CliSloppyImportsResolver::new(
+          SloppyImportsCachedFs::new(Arc::new(deno_fs::RealFs))
+        ).resolve(specifier, SloppyImportsResolutionMode::Execution);
         let data = maybe_sloppy_resolution.as_ref().map(|res| {
           json!({
             "specifier": specifier,
@@ -1496,7 +1499,11 @@ fn diagnose_dependency(
     .data_for_specifier(referrer_doc.file_referrer().unwrap_or(referrer))
     .and_then(|d| d.resolver.maybe_import_map());
   if let Some(import_map) = import_map {
-    if let Resolution::Ok(resolved) = &dependency.maybe_code {
+    let resolved = dependency
+      .maybe_code
+      .ok()
+      .or_else(|| dependency.maybe_type.ok());
+    if let Some(resolved) = resolved {
       if let Some(to) = import_map.lookup(&resolved.specifier, referrer) {
         if dependency_key != to {
           diagnostics.push(
@@ -1514,17 +1521,19 @@ fn diagnose_dependency(
   let import_ranges: Vec<_> = dependency
     .imports
     .iter()
-    .map(|i| documents::to_lsp_range(&i.range))
+    .map(|i| documents::to_lsp_range(&i.specifier_range))
     .collect();
   // TODO(nayeemrmn): This is a crude way of detecting `@deno-types` which has
   // a different specifier and therefore needs a separate call to
   // `diagnose_resolution()`. It would be much cleaner if that were modelled as
   // a separate dependency: https://github.com/denoland/deno_graph/issues/247.
   let is_types_deno_types = !dependency.maybe_type.is_none()
-    && !dependency
-      .imports
-      .iter()
-      .any(|i| dependency.maybe_type.includes(&i.range.start).is_some());
+    && !dependency.imports.iter().any(|i| {
+      dependency
+        .maybe_type
+        .includes(&i.specifier_range.start)
+        .is_some()
+    });
 
   diagnostics.extend(
     diagnose_resolution(
@@ -1698,6 +1707,7 @@ mod tests {
         documents: Arc::new(documents),
         assets: Default::default(),
         config: Arc::new(config),
+        is_cjs_resolver: Default::default(),
         resolver,
       },
     )
diff --git a/cli/lsp/documents.rs b/cli/lsp/documents.rs
index e96b8831bb..b62fa85533 100644
--- a/cli/lsp/documents.rs
+++ b/cli/lsp/documents.rs
@@ -3,7 +3,9 @@
 use super::cache::calculate_fs_version;
 use super::cache::LspCache;
 use super::config::Config;
+use super::resolver::LspIsCjsResolver;
 use super::resolver::LspResolver;
+use super::resolver::SingleReferrerGraphResolver;
 use super::testing::TestCollector;
 use super::testing::TestModule;
 use super::text::LineIndex;
@@ -26,13 +28,14 @@ use deno_core::parking_lot::Mutex;
 use deno_core::ModuleSpecifier;
 use deno_graph::source::ResolutionMode;
 use deno_graph::Resolution;
+use deno_path_util::url_to_file_path;
 use deno_runtime::deno_node;
-use deno_runtime::fs_util::specifier_to_file_path;
 use deno_semver::jsr::JsrPackageReqReference;
 use deno_semver::npm::NpmPackageReqReference;
 use deno_semver::package::PackageReq;
 use indexmap::IndexMap;
 use indexmap::IndexSet;
+use node_resolver::NodeModuleKind;
 use std::borrow::Cow;
 use std::collections::BTreeMap;
 use std::collections::BTreeSet;
@@ -272,7 +275,7 @@ fn get_maybe_test_module_fut(
       parsed_source.specifier().clone(),
       parsed_source.text_info_lazy().clone(),
     );
-    parsed_source.module().visit_with(&mut collector);
+    parsed_source.program().visit_with(&mut collector);
     Arc::new(collector.take())
   })
   .map(Result::ok)
@@ -293,6 +296,8 @@ pub struct Document {
   /// Contains the last-known-good set of dependencies from parsing the module.
   config: Arc<Config>,
   dependencies: Arc<IndexMap<String, deno_graph::Dependency>>,
+  /// If this is maybe a CJS script and maybe not an ES module.
+  is_script: Option<bool>,
   // TODO(nayeemrmn): This is unused, use it for scope attribution for remote
   // modules.
   file_referrer: Option<ModuleSpecifier>,
@@ -323,6 +328,7 @@ impl Document {
     maybe_lsp_version: Option<i32>,
     maybe_language_id: Option<LanguageId>,
     maybe_headers: Option<HashMap<String, String>>,
+    is_cjs_resolver: &LspIsCjsResolver,
     resolver: Arc<LspResolver>,
     config: Arc<Config>,
     cache: &Arc<LspCache>,
@@ -332,12 +338,8 @@ impl Document {
       .filter(|s| cache.is_valid_file_referrer(s))
       .cloned()
       .or(file_referrer);
-    let media_type = resolve_media_type(
-      &specifier,
-      maybe_headers.as_ref(),
-      maybe_language_id,
-      &resolver,
-    );
+    let media_type =
+      resolve_media_type(&specifier, maybe_headers.as_ref(), maybe_language_id);
     let (maybe_parsed_source, maybe_module) =
       if media_type_is_diagnosable(media_type) {
         parse_and_analyze_module(
@@ -346,6 +348,7 @@ impl Document {
           maybe_headers.as_ref(),
           media_type,
           file_referrer.as_ref(),
+          is_cjs_resolver,
           &resolver,
         )
       } else {
@@ -371,6 +374,7 @@ impl Document {
         file_referrer.as_ref(),
       ),
       file_referrer,
+      is_script: maybe_module.as_ref().map(|m| m.is_script),
       maybe_types_dependency,
       line_index,
       maybe_language_id,
@@ -392,6 +396,7 @@ impl Document {
 
   fn with_new_config(
     &self,
+    is_cjs_resolver: &LspIsCjsResolver,
     resolver: Arc<LspResolver>,
     config: Arc<Config>,
   ) -> Arc<Self> {
@@ -399,11 +404,11 @@ impl Document {
       &self.specifier,
       self.maybe_headers.as_ref(),
       self.maybe_language_id,
-      &resolver,
     );
     let dependencies;
     let maybe_types_dependency;
     let maybe_parsed_source;
+    let is_script;
     let maybe_test_module_fut;
     if media_type != self.media_type {
       let parsed_source_result =
@@ -413,6 +418,7 @@ impl Document {
         &parsed_source_result,
         self.maybe_headers.as_ref(),
         self.file_referrer.as_ref(),
+        is_cjs_resolver,
         &resolver,
       )
       .ok();
@@ -420,6 +426,7 @@ impl Document {
         .as_ref()
         .map(|m| Arc::new(m.dependencies.clone()))
         .unwrap_or_default();
+      is_script = maybe_module.as_ref().map(|m| m.is_script);
       maybe_types_dependency = maybe_module
         .as_ref()
         .and_then(|m| Some(Arc::new(m.maybe_types_dependency.clone()?)));
@@ -427,10 +434,19 @@ impl Document {
       maybe_test_module_fut =
         get_maybe_test_module_fut(maybe_parsed_source.as_ref(), &config);
     } else {
-      let graph_resolver =
-        resolver.as_graph_resolver(self.file_referrer.as_ref());
+      let cli_resolver = resolver.as_cli_resolver(self.file_referrer.as_ref());
       let npm_resolver =
         resolver.create_graph_npm_resolver(self.file_referrer.as_ref());
+      let config_data = resolver.as_config_data(self.file_referrer.as_ref());
+      let jsx_import_source_config =
+        config_data.and_then(|d| d.maybe_jsx_import_source_config());
+      let resolver = SingleReferrerGraphResolver {
+        valid_referrer: &self.specifier,
+        referrer_kind: is_cjs_resolver
+          .get_lsp_referrer_kind(&self.specifier, self.is_script),
+        cli_resolver,
+        jsx_import_source_config: jsx_import_source_config.as_ref(),
+      };
       dependencies = Arc::new(
         self
           .dependencies
@@ -441,7 +457,7 @@ impl Document {
               d.with_new_resolver(
                 s,
                 &CliJsrUrlProvider,
-                Some(graph_resolver),
+                Some(&resolver),
                 Some(&npm_resolver),
               ),
             )
@@ -451,10 +467,11 @@ impl Document {
       maybe_types_dependency = self.maybe_types_dependency.as_ref().map(|d| {
         Arc::new(d.with_new_resolver(
           &CliJsrUrlProvider,
-          Some(graph_resolver),
+          Some(&resolver),
           Some(&npm_resolver),
         ))
       });
+      is_script = self.is_script;
       maybe_parsed_source = self.maybe_parsed_source().cloned();
       maybe_test_module_fut = self
         .maybe_test_module_fut
@@ -466,6 +483,7 @@ impl Document {
       // updated properties
       dependencies,
       file_referrer: self.file_referrer.clone(),
+      is_script,
       maybe_types_dependency,
       maybe_navigation_tree: Mutex::new(None),
       // maintain - this should all be copies/clones
@@ -490,6 +508,7 @@ impl Document {
 
   fn with_change(
     &self,
+    is_cjs_resolver: &LspIsCjsResolver,
     version: i32,
     changes: Vec<lsp::TextDocumentContentChangeEvent>,
   ) -> Result<Arc<Self>, AnyError> {
@@ -523,6 +542,7 @@ impl Document {
         self.maybe_headers.as_ref(),
         media_type,
         self.file_referrer.as_ref(),
+        is_cjs_resolver,
         self.resolver.as_ref(),
       )
     } else {
@@ -546,6 +566,7 @@ impl Document {
       get_maybe_test_module_fut(maybe_parsed_source.as_ref(), &self.config);
     Ok(Arc::new(Self {
       config: self.config.clone(),
+      is_script: maybe_module.as_ref().map(|m| m.is_script),
       specifier: self.specifier.clone(),
       file_referrer: self.file_referrer.clone(),
       maybe_fs_version: self.maybe_fs_version.clone(),
@@ -580,6 +601,7 @@ impl Document {
       ),
       maybe_language_id: self.maybe_language_id,
       dependencies: self.dependencies.clone(),
+      is_script: self.is_script,
       maybe_types_dependency: self.maybe_types_dependency.clone(),
       text: self.text.clone(),
       text_info_cell: once_cell::sync::OnceCell::new(),
@@ -607,6 +629,7 @@ impl Document {
       ),
       maybe_language_id: self.maybe_language_id,
       dependencies: self.dependencies.clone(),
+      is_script: self.is_script,
       maybe_types_dependency: self.maybe_types_dependency.clone(),
       text: self.text.clone(),
       text_info_cell: once_cell::sync::OnceCell::new(),
@@ -655,6 +678,13 @@ impl Document {
       })
   }
 
+  /// If this is maybe a CJS script and maybe not an ES module.
+  ///
+  /// Use `LspIsCjsResolver` to determine for sure.
+  pub fn is_script(&self) -> Option<bool> {
+    self.is_script
+  }
+
   pub fn line_index(&self) -> Arc<LineIndex> {
     self.line_index.clone()
   }
@@ -764,14 +794,7 @@ fn resolve_media_type(
   specifier: &ModuleSpecifier,
   maybe_headers: Option<&HashMap<String, String>>,
   maybe_language_id: Option<LanguageId>,
-  resolver: &LspResolver,
 ) -> MediaType {
-  if resolver.in_node_modules(specifier) {
-    if let Some(media_type) = resolver.node_media_type(specifier) {
-      return media_type;
-    }
-  }
-
   if let Some(language_id) = maybe_language_id {
     return MediaType::from_specifier_and_content_type(
       specifier,
@@ -809,6 +832,7 @@ impl FileSystemDocuments {
   pub fn get(
     &self,
     specifier: &ModuleSpecifier,
+    is_cjs_resolver: &LspIsCjsResolver,
     resolver: &Arc<LspResolver>,
     config: &Arc<Config>,
     cache: &Arc<LspCache>,
@@ -832,7 +856,14 @@ impl FileSystemDocuments {
     };
     if dirty {
       // attempt to update the file on the file system
-      self.refresh_document(specifier, resolver, config, cache, file_referrer)
+      self.refresh_document(
+        specifier,
+        is_cjs_resolver,
+        resolver,
+        config,
+        cache,
+        file_referrer,
+      )
     } else {
       old_doc
     }
@@ -843,13 +874,14 @@ impl FileSystemDocuments {
   fn refresh_document(
     &self,
     specifier: &ModuleSpecifier,
+    is_cjs_resolver: &LspIsCjsResolver,
     resolver: &Arc<LspResolver>,
     config: &Arc<Config>,
     cache: &Arc<LspCache>,
     file_referrer: Option<&ModuleSpecifier>,
   ) -> Option<Arc<Document>> {
     let doc = if specifier.scheme() == "file" {
-      let path = specifier_to_file_path(specifier).ok()?;
+      let path = url_to_file_path(specifier).ok()?;
       let bytes = fs::read(path).ok()?;
       let content =
         deno_graph::source::decode_owned_source(specifier, bytes, None).ok()?;
@@ -859,6 +891,7 @@ impl FileSystemDocuments {
         None,
         None,
         None,
+        is_cjs_resolver,
         resolver.clone(),
         config.clone(),
         cache,
@@ -875,6 +908,7 @@ impl FileSystemDocuments {
         None,
         None,
         None,
+        is_cjs_resolver,
         resolver.clone(),
         config.clone(),
         cache,
@@ -902,6 +936,7 @@ impl FileSystemDocuments {
         None,
         None,
         maybe_headers,
+        is_cjs_resolver,
         resolver.clone(),
         config.clone(),
         cache,
@@ -942,6 +977,11 @@ pub struct Documents {
   /// The DENO_DIR that the documents looks for non-file based modules.
   cache: Arc<LspCache>,
   config: Arc<Config>,
+  /// Resolver for detecting if a document is CJS or ESM.
+  is_cjs_resolver: Arc<LspIsCjsResolver>,
+  /// A resolver that takes into account currently loaded import map and JSX
+  /// settings.
+  resolver: Arc<LspResolver>,
   /// A flag that indicates that stated data is potentially invalid and needs to
   /// be recalculated before being considered valid.
   dirty: bool,
@@ -949,9 +989,6 @@ pub struct Documents {
   open_docs: HashMap<ModuleSpecifier, Arc<Document>>,
   /// Documents stored on the file system.
   file_system_docs: Arc<FileSystemDocuments>,
-  /// A resolver that takes into account currently loaded import map and JSX
-  /// settings.
-  resolver: Arc<LspResolver>,
   /// The npm package requirements found in npm specifiers.
   npm_reqs_by_scope:
     Arc<BTreeMap<Option<ModuleSpecifier>, BTreeSet<PackageReq>>>,
@@ -982,6 +1019,7 @@ impl Documents {
       // the cache for remote modules here in order to get the
       // x-typescript-types?
       None,
+      &self.is_cjs_resolver,
       self.resolver.clone(),
       self.config.clone(),
       &self.cache,
@@ -1016,7 +1054,7 @@ impl Documents {
         ))
       })?;
     self.dirty = true;
-    let doc = doc.with_change(version, changes)?;
+    let doc = doc.with_change(&self.is_cjs_resolver, version, changes)?;
     self.open_docs.insert(doc.specifier().clone(), doc.clone());
     Ok(doc)
   }
@@ -1071,34 +1109,6 @@ impl Documents {
     self.cache.is_valid_file_referrer(specifier)
   }
 
-  /// Return `true` if the provided specifier can be resolved to a document,
-  /// otherwise `false`.
-  pub fn contains_import(
-    &self,
-    specifier: &str,
-    referrer: &ModuleSpecifier,
-  ) -> bool {
-    let file_referrer = self.get_file_referrer(referrer);
-    let maybe_specifier = self
-      .resolver
-      .as_graph_resolver(file_referrer.as_deref())
-      .resolve(
-        specifier,
-        &deno_graph::Range {
-          specifier: referrer.clone(),
-          start: deno_graph::Position::zeroed(),
-          end: deno_graph::Position::zeroed(),
-        },
-        ResolutionMode::Types,
-      )
-      .ok();
-    if let Some(import_specifier) = maybe_specifier {
-      self.exists(&import_specifier, file_referrer.as_deref())
-    } else {
-      false
-    }
-  }
-
   pub fn resolve_document_specifier(
     &self,
     specifier: &ModuleSpecifier,
@@ -1136,7 +1146,7 @@ impl Documents {
         return true;
       }
       if specifier.scheme() == "file" {
-        return specifier_to_file_path(&specifier)
+        return url_to_file_path(&specifier)
           .map(|p| p.is_file())
           .unwrap_or(false);
       }
@@ -1173,6 +1183,7 @@ impl Documents {
       if let Some(old_doc) = old_doc {
         self.file_system_docs.get(
           specifier,
+          &self.is_cjs_resolver,
           &self.resolver,
           &self.config,
           &self.cache,
@@ -1197,6 +1208,7 @@ impl Documents {
     } else {
       self.file_system_docs.get(
         &specifier,
+        &self.is_cjs_resolver,
         &self.resolver,
         &self.config,
         &self.cache,
@@ -1255,12 +1267,15 @@ impl Documents {
     referrer: &ModuleSpecifier,
     file_referrer: Option<&ModuleSpecifier>,
   ) -> Vec<Option<(ModuleSpecifier, MediaType)>> {
-    let document = self.get(referrer);
-    let file_referrer = document
+    let referrer_doc = self.get(referrer);
+    let file_referrer = referrer_doc
       .as_ref()
       .and_then(|d| d.file_referrer())
       .or(file_referrer);
-    let dependencies = document.as_ref().map(|d| d.dependencies());
+    let dependencies = referrer_doc.as_ref().map(|d| d.dependencies());
+    let referrer_kind = self
+      .is_cjs_resolver
+      .get_maybe_doc_module_kind(referrer, referrer_doc.as_deref());
     let mut results = Vec::new();
     for raw_specifier in raw_specifiers {
       if raw_specifier.starts_with("asset:") {
@@ -1277,31 +1292,35 @@ impl Documents {
           results.push(self.resolve_dependency(
             specifier,
             referrer,
+            referrer_kind,
             file_referrer,
           ));
         } else if let Some(specifier) = dep.maybe_code.maybe_specifier() {
           results.push(self.resolve_dependency(
             specifier,
             referrer,
+            referrer_kind,
             file_referrer,
           ));
         } else {
           results.push(None);
         }
       } else if let Ok(specifier) =
-        self.resolver.as_graph_resolver(file_referrer).resolve(
+        self.resolver.as_cli_resolver(file_referrer).resolve(
           raw_specifier,
           &deno_graph::Range {
             specifier: referrer.clone(),
             start: deno_graph::Position::zeroed(),
             end: deno_graph::Position::zeroed(),
           },
+          referrer_kind,
           ResolutionMode::Types,
         )
       {
         results.push(self.resolve_dependency(
           &specifier,
           referrer,
+          referrer_kind,
           file_referrer,
         ));
       } else {
@@ -1320,12 +1339,16 @@ impl Documents {
   ) {
     self.config = Arc::new(config.clone());
     self.cache = Arc::new(cache.clone());
+    self.is_cjs_resolver = Arc::new(LspIsCjsResolver::new(cache));
     self.resolver = resolver.clone();
+
+    node_resolver::PackageJsonThreadLocalCache::clear();
+
     {
       let fs_docs = &self.file_system_docs;
       // Clean up non-existent documents.
       fs_docs.docs.retain(|specifier, _| {
-        let Ok(path) = specifier_to_file_path(specifier) else {
+        let Ok(path) = url_to_file_path(specifier) else {
           // Remove non-file schemed docs (deps). They may not be dependencies
           // anymore after updating resolvers.
           return false;
@@ -1340,14 +1363,21 @@ impl Documents {
         if !config.specifier_enabled(doc.specifier()) {
           continue;
         }
-        *doc = doc.with_new_config(self.resolver.clone(), self.config.clone());
+        *doc = doc.with_new_config(
+          &self.is_cjs_resolver,
+          self.resolver.clone(),
+          self.config.clone(),
+        );
       }
       for mut doc in self.file_system_docs.docs.iter_mut() {
         if !config.specifier_enabled(doc.specifier()) {
           continue;
         }
-        *doc.value_mut() =
-          doc.with_new_config(self.resolver.clone(), self.config.clone());
+        *doc.value_mut() = doc.with_new_config(
+          &self.is_cjs_resolver,
+          self.resolver.clone(),
+          self.config.clone(),
+        );
       }
       self.open_docs = open_docs;
       let mut preload_count = 0;
@@ -1364,6 +1394,7 @@ impl Documents {
         {
           fs_docs.refresh_document(
             specifier,
+            &self.is_cjs_resolver,
             &self.resolver,
             &self.config,
             &self.cache,
@@ -1449,6 +1480,7 @@ impl Documents {
     &self,
     specifier: &ModuleSpecifier,
     referrer: &ModuleSpecifier,
+    referrer_kind: NodeModuleKind,
     file_referrer: Option<&ModuleSpecifier>,
   ) -> Option<(ModuleSpecifier, MediaType)> {
     if let Some(module_name) = specifier.as_str().strip_prefix("node:") {
@@ -1462,10 +1494,12 @@ impl Documents {
     let mut specifier = specifier.clone();
     let mut media_type = None;
     if let Ok(npm_ref) = NpmPackageReqReference::from_specifier(&specifier) {
-      let (s, mt) =
-        self
-          .resolver
-          .npm_to_file_url(&npm_ref, referrer, file_referrer)?;
+      let (s, mt) = self.resolver.npm_to_file_url(
+        &npm_ref,
+        referrer,
+        referrer_kind,
+        file_referrer,
+      )?;
       specifier = s;
       media_type = Some(mt);
     }
@@ -1475,7 +1509,8 @@ impl Documents {
       return Some((specifier, media_type));
     };
     if let Some(types) = doc.maybe_types_dependency().maybe_specifier() {
-      self.resolve_dependency(types, &specifier, file_referrer)
+      let specifier_kind = self.is_cjs_resolver.get_doc_module_kind(&doc);
+      self.resolve_dependency(types, &specifier, specifier_kind, file_referrer)
     } else {
       Some((doc.specifier().clone(), doc.media_type()))
     }
@@ -1543,6 +1578,7 @@ fn parse_and_analyze_module(
   maybe_headers: Option<&HashMap<String, String>>,
   media_type: MediaType,
   file_referrer: Option<&ModuleSpecifier>,
+  is_cjs_resolver: &LspIsCjsResolver,
   resolver: &LspResolver,
 ) -> (Option<ParsedSourceResult>, Option<ModuleResult>) {
   let parsed_source_result = parse_source(specifier.clone(), text, media_type);
@@ -1551,6 +1587,7 @@ fn parse_and_analyze_module(
     &parsed_source_result,
     maybe_headers,
     file_referrer,
+    is_cjs_resolver,
     resolver,
   );
   (Some(parsed_source_result), Some(module_result))
@@ -1561,7 +1598,7 @@ fn parse_source(
   text: Arc<str>,
   media_type: MediaType,
 ) -> ParsedSourceResult {
-  deno_ast::parse_module(deno_ast::ParseParams {
+  deno_ast::parse_program(deno_ast::ParseParams {
     specifier,
     text,
     media_type,
@@ -1576,11 +1613,26 @@ fn analyze_module(
   parsed_source_result: &ParsedSourceResult,
   maybe_headers: Option<&HashMap<String, String>>,
   file_referrer: Option<&ModuleSpecifier>,
+  is_cjs_resolver: &LspIsCjsResolver,
   resolver: &LspResolver,
 ) -> ModuleResult {
   match parsed_source_result {
     Ok(parsed_source) => {
       let npm_resolver = resolver.create_graph_npm_resolver(file_referrer);
+      let cli_resolver = resolver.as_cli_resolver(file_referrer);
+      let config_data = resolver.as_config_data(file_referrer);
+      let valid_referrer = specifier.clone();
+      let jsx_import_source_config =
+        config_data.and_then(|d| d.maybe_jsx_import_source_config());
+      let resolver = SingleReferrerGraphResolver {
+        valid_referrer: &valid_referrer,
+        referrer_kind: is_cjs_resolver.get_lsp_referrer_kind(
+          &specifier,
+          Some(parsed_source.compute_is_script()),
+        ),
+        cli_resolver,
+        jsx_import_source_config: jsx_import_source_config.as_ref(),
+      };
       Ok(deno_graph::parse_module_from_ast(
         deno_graph::ParseModuleFromAstOptions {
           graph_kind: deno_graph::GraphKind::TypesOnly,
@@ -1591,7 +1643,7 @@ fn analyze_module(
           // dynamic imports like import(`./dir/${something}`) in the LSP
           file_system: &deno_graph::source::NullFileSystem,
           jsr_url_provider: &CliJsrUrlProvider,
-          maybe_resolver: Some(resolver.as_graph_resolver(file_referrer)),
+          maybe_resolver: Some(&resolver),
           maybe_npm_resolver: Some(&npm_resolver),
         },
       ))
diff --git a/cli/lsp/language_server.rs b/cli/lsp/language_server.rs
index 216b14de62..b2bd72416a 100644
--- a/cli/lsp/language_server.rs
+++ b/cli/lsp/language_server.rs
@@ -15,13 +15,14 @@ use deno_core::url::Url;
 use deno_core::ModuleSpecifier;
 use deno_graph::GraphKind;
 use deno_graph::Resolution;
+use deno_path_util::url_to_file_path;
 use deno_runtime::deno_tls::rustls::RootCertStore;
 use deno_runtime::deno_tls::RootCertStoreProvider;
-use deno_runtime::fs_util::specifier_to_file_path;
 use deno_semver::jsr::JsrPackageReqReference;
 use indexmap::Equivalent;
 use indexmap::IndexSet;
 use log::error;
+use node_resolver::NodeModuleKind;
 use serde::Deserialize;
 use serde_json::from_value;
 use std::collections::BTreeMap;
@@ -77,6 +78,7 @@ use super::parent_process_checker;
 use super::performance::Performance;
 use super::refactor;
 use super::registries::ModuleRegistry;
+use super::resolver::LspIsCjsResolver;
 use super::resolver::LspResolver;
 use super::testing;
 use super::text;
@@ -96,6 +98,7 @@ use crate::args::CaData;
 use crate::args::CacheSetting;
 use crate::args::CliOptions;
 use crate::args::Flags;
+use crate::args::InternalFlags;
 use crate::args::UnstableFmtOptions;
 use crate::factory::CliFactory;
 use crate::file_fetcher::FileFetcher;
@@ -143,6 +146,7 @@ pub struct StateSnapshot {
   pub project_version: usize,
   pub assets: AssetsSnapshot,
   pub config: Arc<Config>,
+  pub is_cjs_resolver: Arc<LspIsCjsResolver>,
   pub documents: Arc<Documents>,
   pub resolver: Arc<LspResolver>,
 }
@@ -202,16 +206,17 @@ pub struct Inner {
   pub documents: Documents,
   http_client_provider: Arc<HttpClientProvider>,
   initial_cwd: PathBuf,
+  pub is_cjs_resolver: Arc<LspIsCjsResolver>,
   jsr_search_api: CliJsrSearchApi,
   /// Handles module registries, which allow discovery of modules
   module_registry: ModuleRegistry,
   /// A lazily create "server" for handling test run requests.
   maybe_testing_server: Option<testing::TestServer>,
-  npm_search_api: CliNpmSearchApi,
+  pub npm_search_api: CliNpmSearchApi,
   project_version: usize,
   /// A collection of measurements which instrument that performance of the LSP.
   performance: Arc<Performance>,
-  resolver: Arc<LspResolver>,
+  pub resolver: Arc<LspResolver>,
   task_queue: LanguageServerTaskQueue,
   /// A memoized version of fixable diagnostic codes retrieved from TypeScript.
   ts_fixable_diagnostics: Vec<String>,
@@ -479,6 +484,7 @@ impl Inner {
     let initial_cwd = std::env::current_dir().unwrap_or_else(|_| {
       panic!("Could not resolve current working directory")
     });
+    let is_cjs_resolver = Arc::new(LspIsCjsResolver::new(&cache));
 
     Self {
       assets,
@@ -490,6 +496,7 @@ impl Inner {
       documents,
       http_client_provider,
       initial_cwd: initial_cwd.clone(),
+      is_cjs_resolver,
       jsr_search_api,
       project_version: 0,
       task_queue: Default::default(),
@@ -600,6 +607,7 @@ impl Inner {
       project_version: self.project_version,
       assets: self.assets.snapshot(),
       config: Arc::new(self.config.clone()),
+      is_cjs_resolver: self.is_cjs_resolver.clone(),
       documents: Arc::new(self.documents.clone()),
       resolver: self.resolver.snapshot(),
     })
@@ -621,12 +629,13 @@ impl Inner {
       }
     });
     self.cache = LspCache::new(global_cache_url);
+    self.is_cjs_resolver = Arc::new(LspIsCjsResolver::new(&self.cache));
     let deno_dir = self.cache.deno_dir();
     let workspace_settings = self.config.workspace_settings();
     let maybe_root_path = self
       .config
       .root_uri()
-      .and_then(|uri| specifier_to_file_path(uri).ok());
+      .and_then(|uri| url_to_file_path(uri).ok());
     let root_cert_store = get_root_cert_store(
       maybe_root_path,
       workspace_settings.certificate_stores.clone(),
@@ -802,7 +811,7 @@ impl Inner {
     let mut roots = config
       .workspace_folders
       .iter()
-      .filter_map(|p| specifier_to_file_path(&p.0).ok())
+      .filter_map(|p| url_to_file_path(&p.0).ok())
       .collect::<Vec<_>>();
     roots.sort();
     let roots = roots
@@ -862,7 +871,10 @@ impl Inner {
           // We ignore these directories by default because there is a
           // high likelihood they aren't relevant. Someone can opt-into
           // them by specifying one of them as an enabled path.
-          if matches!(dir_name.as_str(), "vendor" | "node_modules" | ".git") {
+          if matches!(
+            dir_name.as_str(),
+            "vendor" | "coverage" | "node_modules" | ".git"
+          ) {
             continue;
           }
           // ignore cargo target directories for anyone using Deno with Rust
@@ -903,7 +915,7 @@ impl Inner {
             | MediaType::Tsx => {}
             MediaType::Wasm
             | MediaType::SourceMap
-            | MediaType::TsBuildInfo
+            | MediaType::Css
             | MediaType::Unknown => {
               if path.extension().and_then(|s| s.to_str()) != Some("jsonc") {
                 continue;
@@ -962,6 +974,11 @@ impl Inner {
       .tree
       .refresh(&self.config.settings, &self.workspace_files, &file_fetcher)
       .await;
+    self
+      .client
+      .send_did_refresh_deno_configuration_tree_notification(
+        self.config.tree.to_did_refresh_params(),
+      );
     for config_file in self.config.tree.config_files() {
       (|| {
         let compiler_options = config_file.to_compiler_options().ok()?.options;
@@ -973,7 +990,7 @@ impl Inner {
           spawn(async move {
             let specifier = {
               let inner = ls.inner.read().await;
-              let resolver = inner.resolver.as_graph_resolver(Some(&referrer));
+              let resolver = inner.resolver.as_cli_resolver(Some(&referrer));
               let Ok(specifier) = resolver.resolve(
                 &specifier,
                 &deno_graph::Range {
@@ -981,6 +998,7 @@ impl Inner {
                   start: deno_graph::Position::zeroed(),
                   end: deno_graph::Position::zeroed(),
                 },
+                NodeModuleKind::Esm,
                 deno_graph::source::ResolutionMode::Types,
               ) else {
                 return;
@@ -1124,7 +1142,7 @@ impl Inner {
     {
       return;
     }
-    match specifier_to_file_path(&specifier) {
+    match url_to_file_path(&specifier) {
       Ok(path) if is_importable_ext(&path) => {}
       _ => return,
     }
@@ -1362,7 +1380,7 @@ impl Inner {
     {
       specifier = uri_to_url(&params.text_document.uri);
     }
-    let file_path = specifier_to_file_path(&specifier).map_err(|err| {
+    let file_path = url_to_file_path(&specifier).map_err(|err| {
       error!("{:#}", err);
       LspError::invalid_request()
     })?;
@@ -1378,14 +1396,10 @@ impl Inner {
         .clone();
       fmt_options.use_tabs = Some(!params.options.insert_spaces);
       fmt_options.indent_width = Some(params.options.tab_size as u8);
-      let maybe_workspace = self
-        .config
-        .tree
-        .data_for_specifier(&specifier)
-        .map(|d| &d.member_dir.workspace);
+      let config_data = self.config.tree.data_for_specifier(&specifier);
       let unstable_options = UnstableFmtOptions {
-        component: maybe_workspace
-          .map(|w| w.has_unstable("fmt-component"))
+        component: config_data
+          .map(|d| d.unstable.contains("fmt-component"))
           .unwrap_or(false),
       };
       let document = document.clone();
@@ -1612,11 +1626,15 @@ impl Inner {
         None => false,
       })
       .collect();
+    let mut code_actions = CodeActionCollection::default();
     if !fixable_diagnostics.is_empty() {
-      let mut code_actions = CodeActionCollection::default();
       let file_diagnostics = self
         .diagnostics_server
         .get_ts_diagnostics(&specifier, asset_or_doc.document_lsp_version());
+      let specifier_kind = asset_or_doc
+        .document()
+        .map(|d| self.is_cjs_resolver.get_doc_module_kind(d))
+        .unwrap_or(NodeModuleKind::Esm);
       let mut includes_no_cache = false;
       for diagnostic in &fixable_diagnostics {
         match diagnostic.source.as_deref() {
@@ -1655,7 +1673,13 @@ impl Inner {
               .await;
             for action in actions {
               code_actions
-                .add_ts_fix_action(&specifier, &action, diagnostic, self)
+                .add_ts_fix_action(
+                  &specifier,
+                  specifier_kind,
+                  &action,
+                  diagnostic,
+                  self,
+                )
                 .map_err(|err| {
                   error!("Unable to convert fix: {:#}", err);
                   LspError::internal_error()
@@ -1721,9 +1745,14 @@ impl Inner {
             .add_cache_all_action(&specifier, no_cache_diagnostics.to_owned());
         }
       }
-      code_actions.set_preferred_fixes();
-      all_actions.extend(code_actions.get_response());
     }
+    if let Some(document) = asset_or_doc.document() {
+      code_actions
+        .add_source_actions(document, &params.range, self)
+        .await;
+    }
+    code_actions.set_preferred_fixes();
+    all_actions.extend(code_actions.get_response());
 
     // Refactor
     let only = params
@@ -1796,10 +1825,9 @@ impl Inner {
           error!("Unable to decode code action data: {:#}", err);
           LspError::invalid_params("The CodeAction's data is invalid.")
         })?;
-      let scope = self
-        .get_asset_or_document(&code_action_data.specifier)
-        .ok()
-        .and_then(|d| d.scope().cloned());
+      let maybe_asset_or_doc =
+        self.get_asset_or_document(&code_action_data.specifier).ok();
+      let scope = maybe_asset_or_doc.as_ref().and_then(|d| d.scope().cloned());
       let combined_code_actions = self
         .ts_server
         .get_combined_code_fix(
@@ -1826,8 +1854,13 @@ impl Inner {
       let changes = if code_action_data.fix_id == "fixMissingImport" {
         fix_ts_import_changes(
           &code_action_data.specifier,
+          maybe_asset_or_doc
+            .as_ref()
+            .and_then(|d| d.document())
+            .map(|d| self.is_cjs_resolver.get_doc_module_kind(d))
+            .unwrap_or(NodeModuleKind::Esm),
           &combined_code_actions.changes,
-          &self.get_ts_response_import_mapper(&code_action_data.specifier),
+          self,
         )
         .map_err(|err| {
           error!("Unable to remap changes: {:#}", err);
@@ -1879,8 +1912,12 @@ impl Inner {
       if kind_suffix == ".rewrite.function.returnType" {
         refactor_edit_info.edits = fix_ts_import_changes(
           &action_data.specifier,
+          asset_or_doc
+            .document()
+            .map(|d| self.is_cjs_resolver.get_doc_module_kind(d))
+            .unwrap_or(NodeModuleKind::Esm),
           &refactor_edit_info.edits,
-          &self.get_ts_response_import_mapper(&action_data.specifier),
+          self,
         )
         .map_err(|err| {
           error!("Unable to remap changes: {:#}", err);
@@ -1911,7 +1948,9 @@ impl Inner {
         // todo(dsherret): this should probably just take the resolver itself
         // as the import map is an implementation detail
         .and_then(|d| d.resolver.maybe_import_map()),
-      self.resolver.as_ref(),
+      &self.resolver,
+      &self.ts_server.specifier_map,
+      file_referrer,
     )
   }
 
@@ -2226,6 +2265,7 @@ impl Inner {
         &self.jsr_search_api,
         &self.npm_search_api,
         &self.documents,
+        &self.is_cjs_resolver,
         self.resolver.as_ref(),
         self
           .config
@@ -2273,7 +2313,11 @@ impl Inner {
             .into(),
           scope.cloned(),
         )
-        .await;
+        .await
+        .unwrap_or_else(|err| {
+          error!("Unable to get completion info from TypeScript: {:#}", err);
+          None
+        });
 
       if let Some(completions) = maybe_completion_info {
         response = Some(
@@ -2508,7 +2552,7 @@ impl Inner {
     let maybe_root_path_owned = self
       .config
       .root_uri()
-      .and_then(|uri| specifier_to_file_path(uri).ok());
+      .and_then(|uri| url_to_file_path(uri).ok());
     let mut resolved_items = Vec::<CallHierarchyIncomingCall>::new();
     for item in incoming_calls.iter() {
       if let Some(resolved) = item.try_resolve_call_hierarchy_incoming_call(
@@ -2554,7 +2598,7 @@ impl Inner {
     let maybe_root_path_owned = self
       .config
       .root_uri()
-      .and_then(|uri| specifier_to_file_path(uri).ok());
+      .and_then(|uri| url_to_file_path(uri).ok());
     let mut resolved_items = Vec::<CallHierarchyOutgoingCall>::new();
     for item in outgoing_calls.iter() {
       if let Some(resolved) = item.try_resolve_call_hierarchy_outgoing_call(
@@ -2603,7 +2647,7 @@ impl Inner {
       let maybe_root_path_owned = self
         .config
         .root_uri()
-        .and_then(|uri| specifier_to_file_path(uri).ok());
+        .and_then(|uri| url_to_file_path(uri).ok());
       let mut resolved_items = Vec::<CallHierarchyItem>::new();
       match one_or_many {
         tsc::OneOrMany::One(item) => {
@@ -3600,7 +3644,10 @@ impl Inner {
     };
     let cli_options = CliOptions::new(
       Arc::new(Flags {
-        cache_path: Some(self.cache.deno_dir().root.clone()),
+        internal: InternalFlags {
+          cache_path: Some(self.cache.deno_dir().root.clone()),
+          ..Default::default()
+        },
         ca_stores: workspace_settings.certificate_stores.clone(),
         ca_data: workspace_settings.tls_certificate.clone().map(CaData::File),
         unsafely_ignore_certificate_errors: workspace_settings
@@ -3797,7 +3844,7 @@ impl Inner {
     let maybe_inlay_hints = maybe_inlay_hints.map(|hints| {
       hints
         .iter()
-        .map(|hint| hint.to_lsp(line_index.clone()))
+        .map(|hint| hint.to_lsp(line_index.clone(), self))
         .collect()
     });
     self.performance.measure(mark);
@@ -3933,7 +3980,9 @@ mod tests {
   fn test_walk_workspace() {
     let temp_dir = TempDir::new();
     temp_dir.create_dir_all("root1/vendor/");
+    temp_dir.create_dir_all("root1/coverage/");
     temp_dir.write("root1/vendor/mod.ts", ""); // no, vendor
+    temp_dir.write("root1/coverage/mod.ts", ""); // no, coverage
 
     temp_dir.create_dir_all("root1/node_modules/");
     temp_dir.write("root1/node_modules/mod.ts", ""); // no, node_modules
diff --git a/cli/lsp/lsp_custom.rs b/cli/lsp/lsp_custom.rs
index 5f485db7ac..b570b6d0e2 100644
--- a/cli/lsp/lsp_custom.rs
+++ b/cli/lsp/lsp_custom.rs
@@ -46,6 +46,30 @@ pub struct DiagnosticBatchNotificationParams {
   pub messages_len: usize,
 }
 
+#[derive(Debug, Deserialize, Serialize)]
+#[serde(rename_all = "camelCase")]
+pub struct DenoConfigurationData {
+  pub scope_uri: lsp::Uri,
+  pub workspace_root_scope_uri: Option<lsp::Uri>,
+  pub deno_json: Option<lsp::TextDocumentIdentifier>,
+  pub package_json: Option<lsp::TextDocumentIdentifier>,
+}
+
+#[derive(Debug, Deserialize, Serialize)]
+#[serde(rename_all = "camelCase")]
+pub struct DidRefreshDenoConfigurationTreeNotificationParams {
+  pub data: Vec<DenoConfigurationData>,
+}
+
+pub enum DidRefreshDenoConfigurationTreeNotification {}
+
+impl lsp::notification::Notification
+  for DidRefreshDenoConfigurationTreeNotification
+{
+  type Params = DidRefreshDenoConfigurationTreeNotificationParams;
+  const METHOD: &'static str = "deno/didRefreshDenoConfigurationTree";
+}
+
 #[derive(Debug, Eq, Hash, PartialEq, Copy, Clone, Deserialize, Serialize)]
 #[serde(rename_all = "camelCase")]
 pub enum DenoConfigurationChangeType {
@@ -88,13 +112,15 @@ pub struct DidChangeDenoConfigurationNotificationParams {
   pub changes: Vec<DenoConfigurationChangeEvent>,
 }
 
+// TODO(nayeemrmn): This is being replaced by
+// `DidRefreshDenoConfigurationTreeNotification` for Deno > v2.0.0. Remove it
+// soon.
 pub enum DidChangeDenoConfigurationNotification {}
 
 impl lsp::notification::Notification
   for DidChangeDenoConfigurationNotification
 {
   type Params = DidChangeDenoConfigurationNotificationParams;
-
   const METHOD: &'static str = "deno/didChangeDenoConfiguration";
 }
 
@@ -102,7 +128,6 @@ pub enum DidUpgradeCheckNotification {}
 
 impl lsp::notification::Notification for DidUpgradeCheckNotification {
   type Params = DidUpgradeCheckNotificationParams;
-
   const METHOD: &'static str = "deno/didUpgradeCheck";
 }
 
@@ -125,6 +150,5 @@ pub enum DiagnosticBatchNotification {}
 
 impl lsp::notification::Notification for DiagnosticBatchNotification {
   type Params = DiagnosticBatchNotificationParams;
-
   const METHOD: &'static str = "deno/internalTestDiagnosticBatch";
 }
diff --git a/cli/lsp/npm.rs b/cli/lsp/npm.rs
index 8bdeb7e7d8..2decfc3429 100644
--- a/cli/lsp/npm.rs
+++ b/cli/lsp/npm.rs
@@ -4,6 +4,7 @@ use dashmap::DashMap;
 use deno_core::anyhow::anyhow;
 use deno_core::error::AnyError;
 use deno_core::serde_json;
+use deno_npm::npm_rc::NpmRc;
 use deno_semver::package::PackageNv;
 use deno_semver::Version;
 use serde::Deserialize;
@@ -25,7 +26,10 @@ pub struct CliNpmSearchApi {
 
 impl CliNpmSearchApi {
   pub fn new(file_fetcher: Arc<FileFetcher>) -> Self {
-    let resolver = NpmFetchResolver::new(file_fetcher.clone());
+    let resolver = NpmFetchResolver::new(
+      file_fetcher.clone(),
+      Arc::new(NpmRc::default().as_resolved(npm_registry_url()).unwrap()),
+    );
     Self {
       file_fetcher,
       resolver,
diff --git a/cli/lsp/parent_process_checker.rs b/cli/lsp/parent_process_checker.rs
index e5b2b2f231..b8a42cd1a4 100644
--- a/cli/lsp/parent_process_checker.rs
+++ b/cli/lsp/parent_process_checker.rs
@@ -11,7 +11,7 @@ pub fn start(parent_process_id: u32) {
     std::thread::sleep(Duration::from_secs(10));
 
     if !is_process_active(parent_process_id) {
-      std::process::exit(1);
+      deno_runtime::exit(1);
     }
   });
 }
diff --git a/cli/lsp/registries.rs b/cli/lsp/registries.rs
index 5f7ce00823..ade353e683 100644
--- a/cli/lsp/registries.rs
+++ b/cli/lsp/registries.rs
@@ -482,6 +482,7 @@ impl ModuleRegistry {
         .fetch_with_options(FetchOptions {
           specifier: &specifier,
           permissions: FetchPermissionsOptionRef::AllowAll,
+          maybe_auth: None,
           maybe_accept: Some("application/vnd.deno.reg.v2+json, application/vnd.deno.reg.v1+json;q=0.9, application/json;q=0.8"),
           maybe_cache_setting: None,
         })
diff --git a/cli/lsp/repl.rs b/cli/lsp/repl.rs
index fa5809045e..b4aaa8cd0d 100644
--- a/cli/lsp/repl.rs
+++ b/cli/lsp/repl.rs
@@ -263,7 +263,7 @@ impl ReplLanguageServer {
   }
 
   fn get_document_uri(&self) -> Uri {
-    uri_parse_unencoded(self.cwd_uri.join("$deno$repl.ts").unwrap().as_str())
+    uri_parse_unencoded(self.cwd_uri.join("$deno$repl.mts").unwrap().as_str())
       .unwrap()
   }
 }
diff --git a/cli/lsp/resolver.rs b/cli/lsp/resolver.rs
index 2844eb6f98..399b896381 100644
--- a/cli/lsp/resolver.rs
+++ b/cli/lsp/resolver.rs
@@ -2,27 +2,35 @@
 
 use dashmap::DashMap;
 use deno_ast::MediaType;
+use deno_cache_dir::npm::NpmCacheDir;
 use deno_cache_dir::HttpCache;
+use deno_config::deno_json::JsxImportSourceConfig;
 use deno_config::workspace::PackageJsonDepResolution;
 use deno_config::workspace::WorkspaceResolver;
 use deno_core::url::Url;
-use deno_graph::source::Resolver;
+use deno_graph::source::ResolutionMode;
 use deno_graph::GraphImport;
 use deno_graph::ModuleSpecifier;
+use deno_graph::Range;
 use deno_npm::NpmSystemInfo;
+use deno_path_util::url_from_directory_path;
+use deno_path_util::url_to_file_path;
+use deno_resolver::npm::NpmReqResolverOptions;
+use deno_resolver::DenoResolverOptions;
+use deno_resolver::NodeAndNpmReqResolver;
 use deno_runtime::deno_fs;
 use deno_runtime::deno_node::NodeResolver;
 use deno_runtime::deno_node::PackageJson;
-use deno_runtime::fs_util::specifier_to_file_path;
+use deno_runtime::deno_node::PackageJsonResolver;
 use deno_semver::jsr::JsrPackageReqReference;
 use deno_semver::npm::NpmPackageReqReference;
 use deno_semver::package::PackageNv;
 use deno_semver::package::PackageReq;
 use indexmap::IndexMap;
 use node_resolver::errors::ClosestPkgJsonError;
-use node_resolver::NodeResolution;
+use node_resolver::InNpmPackageChecker;
+use node_resolver::NodeModuleKind;
 use node_resolver::NodeResolutionMode;
-use node_resolver::NpmResolver;
 use std::borrow::Cow;
 use std::collections::BTreeMap;
 use std::collections::BTreeSet;
@@ -31,51 +39,69 @@ use std::collections::HashSet;
 use std::sync::Arc;
 
 use super::cache::LspCache;
+use super::documents::Document;
 use super::jsr::JsrCacheResolver;
 use crate::args::create_default_npmrc;
 use crate::args::CacheSetting;
 use crate::args::CliLockfile;
 use crate::args::NpmInstallDepsProvider;
+use crate::cache::DenoCacheEnvFsAdapter;
+use crate::factory::Deferred;
 use crate::graph_util::CliJsrUrlProvider;
 use crate::http_util::HttpClientProvider;
 use crate::lsp::config::Config;
 use crate::lsp::config::ConfigData;
 use crate::lsp::logging::lsp_warn;
 use crate::npm::create_cli_npm_resolver_for_lsp;
+use crate::npm::CliByonmNpmResolverCreateOptions;
+use crate::npm::CliManagedInNpmPkgCheckerCreateOptions;
+use crate::npm::CliManagedNpmResolverCreateOptions;
 use crate::npm::CliNpmResolver;
-use crate::npm::CliNpmResolverByonmCreateOptions;
 use crate::npm::CliNpmResolverCreateOptions;
-use crate::npm::CliNpmResolverManagedCreateOptions;
 use crate::npm::CliNpmResolverManagedSnapshotOption;
+use crate::npm::CreateInNpmPkgCheckerOptions;
 use crate::npm::ManagedCliNpmResolver;
-use crate::resolver::CjsResolutionStore;
-use crate::resolver::CliGraphResolver;
-use crate::resolver::CliGraphResolverOptions;
-use crate::resolver::CliNodeResolver;
+use crate::resolver::CliDenoResolver;
+use crate::resolver::CliDenoResolverFs;
+use crate::resolver::CliNpmReqResolver;
+use crate::resolver::CliResolver;
+use crate::resolver::CliResolverOptions;
+use crate::resolver::IsCjsResolver;
 use crate::resolver::WorkerCliNpmGraphResolver;
+use crate::tsc::into_specifier_and_media_type;
+use crate::util::fs::canonicalize_path_maybe_not_exists;
 use crate::util::progress_bar::ProgressBar;
 use crate::util::progress_bar::ProgressBarStyle;
 
 #[derive(Debug, Clone)]
 struct LspScopeResolver {
-  graph_resolver: Arc<CliGraphResolver>,
+  resolver: Arc<CliResolver>,
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
   jsr_resolver: Option<Arc<JsrCacheResolver>>,
   npm_resolver: Option<Arc<dyn CliNpmResolver>>,
-  node_resolver: Option<Arc<CliNodeResolver>>,
+  node_resolver: Option<Arc<NodeResolver>>,
+  npm_pkg_req_resolver: Option<Arc<CliNpmReqResolver>>,
+  pkg_json_resolver: Arc<PackageJsonResolver>,
   redirect_resolver: Option<Arc<RedirectResolver>>,
   graph_imports: Arc<IndexMap<ModuleSpecifier, GraphImport>>,
+  package_json_deps_by_resolution: Arc<IndexMap<ModuleSpecifier, String>>,
   config_data: Option<Arc<ConfigData>>,
 }
 
 impl Default for LspScopeResolver {
   fn default() -> Self {
+    let factory = ResolverFactory::new(None);
     Self {
-      graph_resolver: create_graph_resolver(None, None, None),
+      resolver: factory.cli_resolver().clone(),
+      in_npm_pkg_checker: factory.in_npm_pkg_checker().clone(),
       jsr_resolver: None,
       npm_resolver: None,
       node_resolver: None,
+      npm_pkg_req_resolver: None,
+      pkg_json_resolver: factory.pkg_json_resolver().clone(),
       redirect_resolver: None,
       graph_imports: Default::default(),
+      package_json_deps_by_resolution: Default::default(),
       config_data: None,
     }
   }
@@ -87,22 +113,16 @@ impl LspScopeResolver {
     cache: &LspCache,
     http_client_provider: Option<&Arc<HttpClientProvider>>,
   ) -> Self {
-    let mut npm_resolver = None;
-    let mut node_resolver = None;
-    if let Some(http_client) = http_client_provider {
-      npm_resolver = create_npm_resolver(
-        config_data.map(|d| d.as_ref()),
-        cache,
-        http_client,
-      )
-      .await;
-      node_resolver = create_node_resolver(npm_resolver.as_ref());
+    let mut factory = ResolverFactory::new(config_data);
+    if let Some(http_client_provider) = http_client_provider {
+      factory.init_npm_resolver(http_client_provider, cache).await;
     }
-    let graph_resolver = create_graph_resolver(
-      config_data.map(|d| d.as_ref()),
-      npm_resolver.as_ref(),
-      node_resolver.as_ref(),
-    );
+    let in_npm_pkg_checker = factory.in_npm_pkg_checker().clone();
+    let npm_resolver = factory.npm_resolver().cloned();
+    let node_resolver = factory.node_resolver().cloned();
+    let npm_pkg_req_resolver = factory.npm_pkg_req_resolver().cloned();
+    let cli_resolver = factory.cli_resolver().clone();
+    let pkg_json_resolver = factory.pkg_json_resolver().clone();
     let jsr_resolver = Some(Arc::new(JsrCacheResolver::new(
       cache.for_specifier(config_data.map(|d| d.scope.as_ref())),
       config_data.map(|d| d.as_ref()),
@@ -111,7 +131,9 @@ impl LspScopeResolver {
       cache.for_specifier(config_data.map(|d| d.scope.as_ref())),
       config_data.and_then(|d| d.lockfile.clone()),
     )));
-    let npm_graph_resolver = graph_resolver.create_graph_npm_resolver();
+    let npm_graph_resolver = cli_resolver.create_graph_npm_resolver();
+    let maybe_jsx_import_source_config =
+      config_data.and_then(|d| d.maybe_jsx_import_source_config());
     let graph_imports = config_data
       .and_then(|d| d.member_dir.workspace.to_compiler_option_types().ok())
       .map(|imports| {
@@ -119,11 +141,18 @@ impl LspScopeResolver {
           imports
             .into_iter()
             .map(|(referrer, imports)| {
+              let resolver = SingleReferrerGraphResolver {
+                valid_referrer: &referrer,
+                referrer_kind: NodeModuleKind::Esm,
+                cli_resolver: &cli_resolver,
+                jsx_import_source_config: maybe_jsx_import_source_config
+                  .as_ref(),
+              };
               let graph_import = GraphImport::new(
                 &referrer,
                 imports,
                 &CliJsrUrlProvider,
-                Some(graph_resolver.as_ref()),
+                Some(&resolver),
                 Some(&npm_graph_resolver),
               );
               (referrer, graph_import)
@@ -132,33 +161,70 @@ impl LspScopeResolver {
         )
       })
       .unwrap_or_default();
+    let package_json_deps_by_resolution = (|| {
+      let npm_pkg_req_resolver = npm_pkg_req_resolver.as_ref()?;
+      let package_json = config_data?.maybe_pkg_json()?;
+      let referrer = package_json.specifier();
+      let dependencies = package_json.dependencies.as_ref()?;
+      let result = dependencies
+        .iter()
+        .flat_map(|(name, _)| {
+          let req_ref =
+            NpmPackageReqReference::from_str(&format!("npm:{name}")).ok()?;
+          let specifier = into_specifier_and_media_type(Some(
+            npm_pkg_req_resolver
+              .resolve_req_reference(
+                &req_ref,
+                &referrer,
+                // todo(dsherret): this is wrong because it doesn't consider CJS referrers
+                NodeModuleKind::Esm,
+                NodeResolutionMode::Types,
+              )
+              .ok()?,
+          ))
+          .0;
+          Some((specifier, name.clone()))
+        })
+        .collect();
+      Some(result)
+    })();
+    let package_json_deps_by_resolution =
+      Arc::new(package_json_deps_by_resolution.unwrap_or_default());
     Self {
-      graph_resolver,
+      resolver: cli_resolver,
+      in_npm_pkg_checker,
       jsr_resolver,
+      npm_pkg_req_resolver,
       npm_resolver,
       node_resolver,
+      pkg_json_resolver,
       redirect_resolver,
       graph_imports,
+      package_json_deps_by_resolution,
       config_data: config_data.cloned(),
     }
   }
 
   fn snapshot(&self) -> Arc<Self> {
+    let mut factory = ResolverFactory::new(self.config_data.as_ref());
     let npm_resolver =
       self.npm_resolver.as_ref().map(|r| r.clone_snapshotted());
-    let node_resolver = create_node_resolver(npm_resolver.as_ref());
-    let graph_resolver = create_graph_resolver(
-      self.config_data.as_deref(),
-      npm_resolver.as_ref(),
-      node_resolver.as_ref(),
-    );
+    if let Some(npm_resolver) = &npm_resolver {
+      factory.set_npm_resolver(npm_resolver.clone());
+    }
     Arc::new(Self {
-      graph_resolver,
+      resolver: factory.cli_resolver().clone(),
+      in_npm_pkg_checker: factory.in_npm_pkg_checker().clone(),
       jsr_resolver: self.jsr_resolver.clone(),
-      npm_resolver,
-      node_resolver,
+      npm_pkg_req_resolver: factory.npm_pkg_req_resolver().cloned(),
+      npm_resolver: factory.npm_resolver().cloned(),
+      node_resolver: factory.node_resolver().cloned(),
       redirect_resolver: self.redirect_resolver.clone(),
+      pkg_json_resolver: factory.pkg_json_resolver().clone(),
       graph_imports: self.graph_imports.clone(),
+      package_json_deps_by_resolution: self
+        .package_json_deps_by_resolution
+        .clone(),
       config_data: self.config_data.clone(),
     })
   }
@@ -244,12 +310,12 @@ impl LspResolver {
     }
   }
 
-  pub fn as_graph_resolver(
+  pub fn as_cli_resolver(
     &self,
     file_referrer: Option<&ModuleSpecifier>,
-  ) -> &dyn Resolver {
+  ) -> &CliResolver {
     let resolver = self.get_scope_resolver(file_referrer);
-    resolver.graph_resolver.as_ref()
+    resolver.resolver.as_ref()
   }
 
   pub fn create_graph_npm_resolver(
@@ -257,7 +323,23 @@ impl LspResolver {
     file_referrer: Option<&ModuleSpecifier>,
   ) -> WorkerCliNpmGraphResolver {
     let resolver = self.get_scope_resolver(file_referrer);
-    resolver.graph_resolver.create_graph_npm_resolver()
+    resolver.resolver.create_graph_npm_resolver()
+  }
+
+  pub fn as_config_data(
+    &self,
+    file_referrer: Option<&ModuleSpecifier>,
+  ) -> Option<&Arc<ConfigData>> {
+    let resolver = self.get_scope_resolver(file_referrer);
+    resolver.config_data.as_ref()
+  }
+
+  pub fn in_npm_pkg_checker(
+    &self,
+    file_referrer: Option<&ModuleSpecifier>,
+  ) -> &Arc<dyn InNpmPackageChecker> {
+    let resolver = self.get_scope_resolver(file_referrer);
+    &resolver.in_npm_pkg_checker
   }
 
   pub fn maybe_managed_npm_resolver(
@@ -323,15 +405,33 @@ impl LspResolver {
     &self,
     req_ref: &NpmPackageReqReference,
     referrer: &ModuleSpecifier,
+    referrer_kind: NodeModuleKind,
     file_referrer: Option<&ModuleSpecifier>,
   ) -> Option<(ModuleSpecifier, MediaType)> {
     let resolver = self.get_scope_resolver(file_referrer);
-    let node_resolver = resolver.node_resolver.as_ref()?;
-    Some(NodeResolution::into_specifier_and_media_type(
-      node_resolver
-        .resolve_req_reference(req_ref, referrer, NodeResolutionMode::Types)
-        .ok(),
-    ))
+    let npm_pkg_req_resolver = resolver.npm_pkg_req_resolver.as_ref()?;
+    Some(into_specifier_and_media_type(Some(
+      npm_pkg_req_resolver
+        .resolve_req_reference(
+          req_ref,
+          referrer,
+          referrer_kind,
+          NodeResolutionMode::Types,
+        )
+        .ok()?,
+    )))
+  }
+
+  pub fn file_url_to_package_json_dep(
+    &self,
+    specifier: &ModuleSpecifier,
+    file_referrer: Option<&ModuleSpecifier>,
+  ) -> Option<String> {
+    let resolver = self.get_scope_resolver(file_referrer);
+    resolver
+      .package_json_deps_by_resolution
+      .get(specifier)
+      .cloned()
   }
 
   pub fn in_node_modules(&self, specifier: &ModuleSpecifier) -> bool {
@@ -345,14 +445,10 @@ impl LspResolver {
           .contains("/node_modules/")
     }
 
-    let global_npm_resolver = self
-      .get_scope_resolver(Some(specifier))
-      .npm_resolver
-      .as_ref()
-      .and_then(|npm_resolver| npm_resolver.as_managed())
-      .filter(|r| r.root_node_modules_path().is_none());
-    if let Some(npm_resolver) = &global_npm_resolver {
-      if npm_resolver.in_npm_package(specifier) {
+    if let Some(node_resolver) =
+      &self.get_scope_resolver(Some(specifier)).node_resolver
+    {
+      if node_resolver.in_npm_package(specifier) {
         return true;
       }
     }
@@ -360,16 +456,27 @@ impl LspResolver {
     has_node_modules_dir(specifier)
   }
 
-  pub fn node_media_type(
+  pub fn is_bare_package_json_dep(
     &self,
-    specifier: &ModuleSpecifier,
-  ) -> Option<MediaType> {
-    let resolver = self.get_scope_resolver(Some(specifier));
-    let node_resolver = resolver.node_resolver.as_ref()?;
-    let resolution = node_resolver
-      .url_to_node_resolution(specifier.clone())
-      .ok()?;
-    Some(NodeResolution::into_specifier_and_media_type(Some(resolution)).1)
+    specifier_text: &str,
+    referrer: &ModuleSpecifier,
+    referrer_kind: NodeModuleKind,
+  ) -> bool {
+    let resolver = self.get_scope_resolver(Some(referrer));
+    let Some(npm_pkg_req_resolver) = resolver.npm_pkg_req_resolver.as_ref()
+    else {
+      return false;
+    };
+    npm_pkg_req_resolver
+      .resolve_if_for_npm_pkg(
+        specifier_text,
+        referrer,
+        referrer_kind,
+        NodeResolutionMode::Types,
+      )
+      .ok()
+      .flatten()
+      .is_some()
   }
 
   pub fn get_closest_package_json(
@@ -377,10 +484,9 @@ impl LspResolver {
     referrer: &ModuleSpecifier,
   ) -> Result<Option<Arc<PackageJson>>, ClosestPkgJsonError> {
     let resolver = self.get_scope_resolver(Some(referrer));
-    let Some(node_resolver) = resolver.node_resolver.as_ref() else {
-      return Ok(None);
-    };
-    node_resolver.get_closest_package_json(referrer)
+    resolver
+      .pkg_json_resolver
+      .get_closest_package_json(referrer)
   }
 
   pub fn resolve_redirects(
@@ -432,113 +538,206 @@ impl LspResolver {
   }
 }
 
-async fn create_npm_resolver(
-  config_data: Option<&ConfigData>,
-  cache: &LspCache,
-  http_client_provider: &Arc<HttpClientProvider>,
-) -> Option<Arc<dyn CliNpmResolver>> {
-  let enable_byonm = config_data.map(|d| d.byonm).unwrap_or(false);
-  let options = if enable_byonm {
-    CliNpmResolverCreateOptions::Byonm(CliNpmResolverByonmCreateOptions {
-      fs: Arc::new(deno_fs::RealFs),
-      root_node_modules_dir: config_data.and_then(|config_data| {
-        config_data.node_modules_dir.clone().or_else(|| {
-          specifier_to_file_path(&config_data.scope)
-            .ok()
-            .map(|p| p.join("node_modules/"))
-        })
-      }),
-    })
-  } else {
-    CliNpmResolverCreateOptions::Managed(CliNpmResolverManagedCreateOptions {
-      http_client_provider: http_client_provider.clone(),
-      snapshot: match config_data.and_then(|d| d.lockfile.as_ref()) {
-        Some(lockfile) => {
-          CliNpmResolverManagedSnapshotOption::ResolveFromLockfile(
-            lockfile.clone(),
-          )
-        }
-        None => CliNpmResolverManagedSnapshotOption::Specified(None),
-      },
-      // Don't provide the lockfile. We don't want these resolvers
-      // updating it. Only the cache request should update the lockfile.
-      maybe_lockfile: None,
-      fs: Arc::new(deno_fs::RealFs),
-      npm_global_cache_dir: cache.deno_dir().npm_folder_path(),
-      // Use an "only" cache setting in order to make the
-      // user do an explicit "cache" command and prevent
-      // the cache from being filled with lots of packages while
-      // the user is typing.
-      cache_setting: CacheSetting::Only,
-      text_only_progress_bar: ProgressBar::new(ProgressBarStyle::TextOnly),
-      maybe_node_modules_path: config_data
-        .and_then(|d| d.node_modules_dir.clone()),
-      // only used for top level install, so we can ignore this
-      npm_install_deps_provider: Arc::new(NpmInstallDepsProvider::empty()),
-      npmrc: config_data
+#[derive(Default)]
+struct ResolverFactoryServices {
+  cli_resolver: Deferred<Arc<CliResolver>>,
+  in_npm_pkg_checker: Deferred<Arc<dyn InNpmPackageChecker>>,
+  node_resolver: Deferred<Option<Arc<NodeResolver>>>,
+  npm_pkg_req_resolver: Deferred<Option<Arc<CliNpmReqResolver>>>,
+  npm_resolver: Option<Arc<dyn CliNpmResolver>>,
+}
+
+struct ResolverFactory<'a> {
+  config_data: Option<&'a Arc<ConfigData>>,
+  fs: Arc<dyn deno_fs::FileSystem>,
+  pkg_json_resolver: Arc<PackageJsonResolver>,
+  services: ResolverFactoryServices,
+}
+
+impl<'a> ResolverFactory<'a> {
+  pub fn new(config_data: Option<&'a Arc<ConfigData>>) -> Self {
+    let fs = Arc::new(deno_fs::RealFs);
+    let pkg_json_resolver = Arc::new(PackageJsonResolver::new(
+      deno_runtime::deno_node::DenoFsNodeResolverEnv::new(fs.clone()),
+    ));
+    Self {
+      config_data,
+      fs,
+      pkg_json_resolver,
+      services: Default::default(),
+    }
+  }
+
+  async fn init_npm_resolver(
+    &mut self,
+    http_client_provider: &Arc<HttpClientProvider>,
+    cache: &LspCache,
+  ) {
+    let enable_byonm = self.config_data.map(|d| d.byonm).unwrap_or(false);
+    let options = if enable_byonm {
+      CliNpmResolverCreateOptions::Byonm(CliByonmNpmResolverCreateOptions {
+        fs: CliDenoResolverFs(Arc::new(deno_fs::RealFs)),
+        pkg_json_resolver: self.pkg_json_resolver.clone(),
+        root_node_modules_dir: self.config_data.and_then(|config_data| {
+          config_data.node_modules_dir.clone().or_else(|| {
+            url_to_file_path(&config_data.scope)
+              .ok()
+              .map(|p| p.join("node_modules/"))
+          })
+        }),
+      })
+    } else {
+      let npmrc = self
+        .config_data
         .and_then(|d| d.npmrc.clone())
-        .unwrap_or_else(create_default_npmrc),
-      npm_system_info: NpmSystemInfo::default(),
-      lifecycle_scripts: Default::default(),
+        .unwrap_or_else(create_default_npmrc);
+      let npm_cache_dir = Arc::new(NpmCacheDir::new(
+        &DenoCacheEnvFsAdapter(self.fs.as_ref()),
+        cache.deno_dir().npm_folder_path(),
+        npmrc.get_all_known_registries_urls(),
+      ));
+      CliNpmResolverCreateOptions::Managed(CliManagedNpmResolverCreateOptions {
+        http_client_provider: http_client_provider.clone(),
+        snapshot: match self.config_data.and_then(|d| d.lockfile.as_ref()) {
+          Some(lockfile) => {
+            CliNpmResolverManagedSnapshotOption::ResolveFromLockfile(
+              lockfile.clone(),
+            )
+          }
+          None => CliNpmResolverManagedSnapshotOption::Specified(None),
+        },
+        // Don't provide the lockfile. We don't want these resolvers
+        // updating it. Only the cache request should update the lockfile.
+        maybe_lockfile: None,
+        fs: Arc::new(deno_fs::RealFs),
+        npm_cache_dir,
+        // Use an "only" cache setting in order to make the
+        // user do an explicit "cache" command and prevent
+        // the cache from being filled with lots of packages while
+        // the user is typing.
+        cache_setting: CacheSetting::Only,
+        text_only_progress_bar: ProgressBar::new(ProgressBarStyle::TextOnly),
+        maybe_node_modules_path: self
+          .config_data
+          .and_then(|d| d.node_modules_dir.clone()),
+        // only used for top level install, so we can ignore this
+        npm_install_deps_provider: Arc::new(NpmInstallDepsProvider::empty()),
+        npmrc,
+        npm_system_info: NpmSystemInfo::default(),
+        lifecycle_scripts: Default::default(),
+      })
+    };
+    self.set_npm_resolver(create_cli_npm_resolver_for_lsp(options).await);
+  }
+
+  pub fn set_npm_resolver(&mut self, npm_resolver: Arc<dyn CliNpmResolver>) {
+    self.services.npm_resolver = Some(npm_resolver);
+  }
+
+  pub fn npm_resolver(&self) -> Option<&Arc<dyn CliNpmResolver>> {
+    self.services.npm_resolver.as_ref()
+  }
+
+  pub fn cli_resolver(&self) -> &Arc<CliResolver> {
+    self.services.cli_resolver.get_or_init(|| {
+      let npm_req_resolver = self.npm_pkg_req_resolver().cloned();
+      let deno_resolver = Arc::new(CliDenoResolver::new(DenoResolverOptions {
+        in_npm_pkg_checker: self.in_npm_pkg_checker().clone(),
+        node_and_req_resolver: match (self.node_resolver(), npm_req_resolver) {
+          (Some(node_resolver), Some(npm_req_resolver)) => {
+            Some(NodeAndNpmReqResolver {
+              node_resolver: node_resolver.clone(),
+              npm_req_resolver,
+            })
+          }
+          _ => None,
+        },
+        sloppy_imports_resolver: self
+          .config_data
+          .and_then(|d| d.sloppy_imports_resolver.clone()),
+        workspace_resolver: self
+          .config_data
+          .map(|d| d.resolver.clone())
+          .unwrap_or_else(|| {
+            Arc::new(WorkspaceResolver::new_raw(
+              // this is fine because this is only used before initialization
+              Arc::new(ModuleSpecifier::parse("file:///").unwrap()),
+              None,
+              Vec::new(),
+              Vec::new(),
+              PackageJsonDepResolution::Disabled,
+            ))
+          }),
+        is_byonm: self.config_data.map(|d| d.byonm).unwrap_or(false),
+        maybe_vendor_dir: self.config_data.and_then(|d| d.vendor_dir.as_ref()),
+      }));
+      Arc::new(CliResolver::new(CliResolverOptions {
+        deno_resolver,
+        npm_resolver: self.npm_resolver().cloned(),
+        bare_node_builtins_enabled: self
+          .config_data
+          .is_some_and(|d| d.unstable.contains("bare-node-builtins")),
+      }))
     })
-  };
-  Some(create_cli_npm_resolver_for_lsp(options).await)
-}
+  }
 
-fn create_node_resolver(
-  npm_resolver: Option<&Arc<dyn CliNpmResolver>>,
-) -> Option<Arc<CliNodeResolver>> {
-  use once_cell::sync::Lazy;
+  pub fn pkg_json_resolver(&self) -> &Arc<PackageJsonResolver> {
+    &self.pkg_json_resolver
+  }
 
-  // it's not ideal to share this across all scopes and to
-  // never clear it, but it's fine for the time being
-  static CJS_RESOLUTIONS: Lazy<Arc<CjsResolutionStore>> =
-    Lazy::new(Default::default);
+  pub fn in_npm_pkg_checker(&self) -> &Arc<dyn InNpmPackageChecker> {
+    self.services.in_npm_pkg_checker.get_or_init(|| {
+      crate::npm::create_in_npm_pkg_checker(
+        match self.services.npm_resolver.as_ref().map(|r| r.as_inner()) {
+          Some(crate::npm::InnerCliNpmResolverRef::Byonm(_)) | None => {
+            CreateInNpmPkgCheckerOptions::Byonm
+          }
+          Some(crate::npm::InnerCliNpmResolverRef::Managed(m)) => {
+            CreateInNpmPkgCheckerOptions::Managed(
+              CliManagedInNpmPkgCheckerCreateOptions {
+                root_cache_dir_url: m.global_cache_root_url(),
+                maybe_node_modules_path: m.maybe_node_modules_path(),
+              },
+            )
+          }
+        },
+      )
+    })
+  }
 
-  let npm_resolver = npm_resolver?;
-  let fs = Arc::new(deno_fs::RealFs);
-  let node_resolver_inner = Arc::new(NodeResolver::new(
-    deno_runtime::deno_node::DenoFsNodeResolverEnv::new(fs.clone()),
-    npm_resolver.clone().into_npm_resolver(),
-  ));
-  Some(Arc::new(CliNodeResolver::new(
-    CJS_RESOLUTIONS.clone(),
-    fs,
-    node_resolver_inner,
-    npm_resolver.clone(),
-  )))
-}
+  pub fn node_resolver(&self) -> Option<&Arc<NodeResolver>> {
+    self
+      .services
+      .node_resolver
+      .get_or_init(|| {
+        let npm_resolver = self.services.npm_resolver.as_ref()?;
+        Some(Arc::new(NodeResolver::new(
+          deno_runtime::deno_node::DenoFsNodeResolverEnv::new(self.fs.clone()),
+          self.in_npm_pkg_checker().clone(),
+          npm_resolver.clone().into_npm_pkg_folder_resolver(),
+          self.pkg_json_resolver.clone(),
+        )))
+      })
+      .as_ref()
+  }
 
-fn create_graph_resolver(
-  config_data: Option<&ConfigData>,
-  npm_resolver: Option<&Arc<dyn CliNpmResolver>>,
-  node_resolver: Option<&Arc<CliNodeResolver>>,
-) -> Arc<CliGraphResolver> {
-  let workspace = config_data.map(|d| &d.member_dir.workspace);
-  Arc::new(CliGraphResolver::new(CliGraphResolverOptions {
-    node_resolver: node_resolver.cloned(),
-    npm_resolver: npm_resolver.cloned(),
-    workspace_resolver: config_data.map(|d| d.resolver.clone()).unwrap_or_else(
-      || {
-        Arc::new(WorkspaceResolver::new_raw(
-          // this is fine because this is only used before initialization
-          Arc::new(ModuleSpecifier::parse("file:///").unwrap()),
-          None,
-          Vec::new(),
-          Vec::new(),
-          PackageJsonDepResolution::Disabled,
-        ))
-      },
-    ),
-    maybe_jsx_import_source_config: workspace.and_then(|workspace| {
-      workspace.to_maybe_jsx_import_source_config().ok().flatten()
-    }),
-    maybe_vendor_dir: config_data.and_then(|d| d.vendor_dir.as_ref()),
-    bare_node_builtins_enabled: workspace
-      .is_some_and(|workspace| workspace.has_unstable("bare-node-builtins")),
-    sloppy_imports_resolver: config_data
-      .and_then(|d| d.sloppy_imports_resolver.clone()),
-  }))
+  pub fn npm_pkg_req_resolver(&self) -> Option<&Arc<CliNpmReqResolver>> {
+    self
+      .services
+      .npm_pkg_req_resolver
+      .get_or_init(|| {
+        let node_resolver = self.node_resolver()?;
+        let npm_resolver = self.npm_resolver()?;
+        Some(Arc::new(CliNpmReqResolver::new(NpmReqResolverOptions {
+          byonm_resolver: (npm_resolver.clone()).into_maybe_byonm(),
+          fs: CliDenoResolverFs(self.fs.clone()),
+          in_npm_pkg_checker: self.in_npm_pkg_checker().clone(),
+          node_resolver: node_resolver.clone(),
+          npm_req_resolver: npm_resolver.clone().into_npm_req_resolver(),
+        })))
+      })
+      .as_ref()
+  }
 }
 
 #[derive(Debug, Eq, PartialEq)]
@@ -565,6 +764,141 @@ impl std::fmt::Debug for RedirectResolver {
   }
 }
 
+#[derive(Debug)]
+pub struct LspIsCjsResolver {
+  inner: IsCjsResolver,
+}
+
+impl Default for LspIsCjsResolver {
+  fn default() -> Self {
+    LspIsCjsResolver::new(&Default::default())
+  }
+}
+
+impl LspIsCjsResolver {
+  pub fn new(cache: &LspCache) -> Self {
+    #[derive(Debug)]
+    struct LspInNpmPackageChecker {
+      global_cache_dir: ModuleSpecifier,
+    }
+
+    impl LspInNpmPackageChecker {
+      pub fn new(cache: &LspCache) -> Self {
+        let npm_folder_path = cache.deno_dir().npm_folder_path();
+        Self {
+          global_cache_dir: url_from_directory_path(
+            &canonicalize_path_maybe_not_exists(&npm_folder_path)
+              .unwrap_or(npm_folder_path),
+          )
+          .unwrap_or_else(|_| {
+            ModuleSpecifier::parse("file:///invalid/").unwrap()
+          }),
+        }
+      }
+    }
+
+    impl InNpmPackageChecker for LspInNpmPackageChecker {
+      fn in_npm_package(&self, specifier: &ModuleSpecifier) -> bool {
+        if specifier.scheme() != "file" {
+          return false;
+        }
+        if specifier
+          .as_str()
+          .starts_with(self.global_cache_dir.as_str())
+        {
+          return true;
+        }
+        specifier.as_str().contains("/node_modules/")
+      }
+    }
+
+    let fs = Arc::new(deno_fs::RealFs);
+    let pkg_json_resolver = Arc::new(PackageJsonResolver::new(
+      deno_runtime::deno_node::DenoFsNodeResolverEnv::new(fs.clone()),
+    ));
+
+    LspIsCjsResolver {
+      inner: IsCjsResolver::new(
+        Arc::new(LspInNpmPackageChecker::new(cache)),
+        pkg_json_resolver,
+        crate::resolver::IsCjsResolverOptions {
+          detect_cjs: true,
+          is_node_main: false,
+        },
+      ),
+    }
+  }
+
+  pub fn get_maybe_doc_module_kind(
+    &self,
+    specifier: &ModuleSpecifier,
+    maybe_document: Option<&Document>,
+  ) -> NodeModuleKind {
+    self.get_lsp_referrer_kind(
+      specifier,
+      maybe_document.and_then(|d| d.is_script()),
+    )
+  }
+
+  pub fn get_doc_module_kind(&self, document: &Document) -> NodeModuleKind {
+    self.get_lsp_referrer_kind(document.specifier(), document.is_script())
+  }
+
+  pub fn get_lsp_referrer_kind(
+    &self,
+    specifier: &ModuleSpecifier,
+    is_script: Option<bool>,
+  ) -> NodeModuleKind {
+    self.inner.get_lsp_referrer_kind(specifier, is_script)
+  }
+}
+
+#[derive(Debug)]
+pub struct SingleReferrerGraphResolver<'a> {
+  pub valid_referrer: &'a ModuleSpecifier,
+  pub referrer_kind: NodeModuleKind,
+  pub cli_resolver: &'a CliResolver,
+  pub jsx_import_source_config: Option<&'a JsxImportSourceConfig>,
+}
+
+impl<'a> deno_graph::source::Resolver for SingleReferrerGraphResolver<'a> {
+  fn default_jsx_import_source(&self) -> Option<String> {
+    self
+      .jsx_import_source_config
+      .and_then(|c| c.default_specifier.clone())
+  }
+
+  fn default_jsx_import_source_types(&self) -> Option<String> {
+    self
+      .jsx_import_source_config
+      .and_then(|c| c.default_types_specifier.clone())
+  }
+
+  fn jsx_import_source_module(&self) -> &str {
+    self
+      .jsx_import_source_config
+      .map(|c| c.module.as_str())
+      .unwrap_or(deno_graph::source::DEFAULT_JSX_IMPORT_SOURCE_MODULE)
+  }
+
+  fn resolve(
+    &self,
+    specifier_text: &str,
+    referrer_range: &Range,
+    mode: ResolutionMode,
+  ) -> Result<ModuleSpecifier, deno_graph::source::ResolveError> {
+    // this resolver assumes it will only be used with a single referrer
+    // with the provided referrer kind
+    debug_assert_eq!(referrer_range.specifier, *self.valid_referrer);
+    self.cli_resolver.resolve(
+      specifier_text,
+      referrer_range,
+      self.referrer_kind,
+      mode,
+    )
+  }
+}
+
 impl RedirectResolver {
   fn new(
     cache: Arc<dyn HttpCache>,
diff --git a/cli/lsp/testing/collectors.rs b/cli/lsp/testing/collectors.rs
index 2f2ddb8773..2dd7ec0d96 100644
--- a/cli/lsp/testing/collectors.rs
+++ b/cli/lsp/testing/collectors.rs
@@ -650,7 +650,7 @@ pub mod tests {
     .unwrap();
     let text_info = parsed_module.text_info_lazy().clone();
     let mut collector = TestCollector::new(specifier, text_info);
-    parsed_module.module().visit_with(&mut collector);
+    parsed_module.program().visit_with(&mut collector);
     collector.take()
   }
 
diff --git a/cli/lsp/tsc.rs b/cli/lsp/tsc.rs
index fe3708d3cb..48dcb79644 100644
--- a/cli/lsp/tsc.rs
+++ b/cli/lsp/tsc.rs
@@ -34,6 +34,7 @@ use crate::util::path::relative_specifier;
 use crate::util::path::to_percent_decoded_str;
 use crate::util::result::InfallibleResultExt;
 use crate::util::v8::convert;
+use crate::worker::create_isolate_create_params;
 use deno_core::convert::Smi;
 use deno_core::convert::ToV8;
 use deno_core::error::StdAnyError;
@@ -62,13 +63,14 @@ use deno_core::ModuleSpecifier;
 use deno_core::OpState;
 use deno_core::PollEventLoopOptions;
 use deno_core::RuntimeOptions;
-use deno_runtime::fs_util::specifier_to_file_path;
+use deno_path_util::url_to_file_path;
 use deno_runtime::inspector_server::InspectorServer;
 use deno_runtime::tokio_util::create_basic_runtime;
 use indexmap::IndexMap;
 use indexmap::IndexSet;
 use lazy_regex::lazy_regex;
 use log::error;
+use node_resolver::NodeModuleKind;
 use once_cell::sync::Lazy;
 use regex::Captures;
 use regex::Regex;
@@ -236,7 +238,7 @@ pub struct TsServer {
   performance: Arc<Performance>,
   sender: mpsc::UnboundedSender<Request>,
   receiver: Mutex<Option<mpsc::UnboundedReceiver<Request>>>,
-  specifier_map: Arc<TscSpecifierMap>,
+  pub specifier_map: Arc<TscSpecifierMap>,
   inspector_server: Mutex<Option<Arc<InspectorServer>>>,
   pending_change: Mutex<Option<PendingChange>>,
 }
@@ -882,20 +884,22 @@ impl TsServer {
     options: GetCompletionsAtPositionOptions,
     format_code_settings: FormatCodeSettings,
     scope: Option<ModuleSpecifier>,
-  ) -> Option<CompletionInfo> {
+  ) -> Result<Option<CompletionInfo>, AnyError> {
     let req = TscRequest::GetCompletionsAtPosition(Box::new((
       self.specifier_map.denormalize(&specifier),
       position,
       options,
       format_code_settings,
     )));
-    match self.request(snapshot, req, scope).await {
-      Ok(maybe_info) => maybe_info,
-      Err(err) => {
-        log::error!("Unable to get completion info from TypeScript: {:#}", err);
-        None
-      }
-    }
+    self
+      .request::<Option<CompletionInfo>>(snapshot, req, scope)
+      .await
+      .map(|mut info| {
+        if let Some(info) = &mut info {
+          info.normalize(&self.specifier_map);
+        }
+        info
+      })
   }
 
   pub async fn get_completion_details(
@@ -2182,6 +2186,50 @@ impl NavigateToItem {
   }
 }
 
+#[derive(Debug, Clone, Deserialize)]
+#[serde(rename_all = "camelCase")]
+pub struct InlayHintDisplayPart {
+  pub text: String,
+  pub span: Option<TextSpan>,
+  pub file: Option<String>,
+}
+
+impl InlayHintDisplayPart {
+  pub fn to_lsp(
+    &self,
+    language_server: &language_server::Inner,
+  ) -> lsp::InlayHintLabelPart {
+    let location = self.file.as_ref().map(|f| {
+      let specifier =
+        resolve_url(f).unwrap_or_else(|_| INVALID_SPECIFIER.clone());
+      let file_referrer =
+        language_server.documents.get_file_referrer(&specifier);
+      let uri = language_server
+        .url_map
+        .specifier_to_uri(&specifier, file_referrer.as_deref())
+        .unwrap_or_else(|_| INVALID_URI.clone());
+      let range = self
+        .span
+        .as_ref()
+        .and_then(|s| {
+          let asset_or_doc =
+            language_server.get_asset_or_document(&specifier).ok()?;
+          Some(s.to_range(asset_or_doc.line_index()))
+        })
+        .unwrap_or_else(|| {
+          lsp::Range::new(lsp::Position::new(0, 0), lsp::Position::new(0, 0))
+        });
+      lsp::Location { uri, range }
+    });
+    lsp::InlayHintLabelPart {
+      value: self.text.clone(),
+      tooltip: None,
+      location,
+      command: None,
+    }
+  }
+}
+
 #[derive(Debug, Clone, Deserialize)]
 pub enum InlayHintKind {
   Type,
@@ -2203,6 +2251,7 @@ impl InlayHintKind {
 #[serde(rename_all = "camelCase")]
 pub struct InlayHint {
   pub text: String,
+  pub display_parts: Option<Vec<InlayHintDisplayPart>>,
   pub position: u32,
   pub kind: InlayHintKind,
   pub whitespace_before: Option<bool>,
@@ -2210,10 +2259,23 @@ pub struct InlayHint {
 }
 
 impl InlayHint {
-  pub fn to_lsp(&self, line_index: Arc<LineIndex>) -> lsp::InlayHint {
+  pub fn to_lsp(
+    &self,
+    line_index: Arc<LineIndex>,
+    language_server: &language_server::Inner,
+  ) -> lsp::InlayHint {
     lsp::InlayHint {
       position: line_index.position_tsc(self.position.into()),
-      label: lsp::InlayHintLabel::String(self.text.clone()),
+      label: if let Some(display_parts) = &self.display_parts {
+        lsp::InlayHintLabel::LabelParts(
+          display_parts
+            .iter()
+            .map(|p| p.to_lsp(language_server))
+            .collect(),
+        )
+      } else {
+        lsp::InlayHintLabel::String(self.text.clone())
+      },
       kind: self.kind.to_lsp(),
       padding_left: self.whitespace_before,
       padding_right: self.whitespace_after,
@@ -3191,7 +3253,7 @@ impl CallHierarchyItem {
     let use_file_name = self.is_source_file_item();
     let maybe_file_path = if uri.scheme().is_some_and(|s| s.as_str() == "file")
     {
-      specifier_to_file_path(&uri_to_url(&uri)).ok()
+      url_to_file_path(&uri_to_url(&uri)).ok()
     } else {
       None
     };
@@ -3584,6 +3646,12 @@ pub struct CompletionInfo {
 }
 
 impl CompletionInfo {
+  fn normalize(&mut self, specifier_map: &TscSpecifierMap) {
+    for entry in &mut self.entries {
+      entry.normalize(specifier_map);
+    }
+  }
+
   pub fn as_completion_response(
     &self,
     line_index: Arc<LineIndex>,
@@ -3645,11 +3713,17 @@ pub struct CompletionItemData {
 
 #[derive(Debug, Deserialize, Serialize)]
 #[serde(rename_all = "camelCase")]
-struct CompletionEntryDataImport {
+struct CompletionEntryDataAutoImport {
   module_specifier: String,
   file_name: String,
 }
 
+#[derive(Debug)]
+pub struct CompletionNormalizedAutoImportData {
+  raw: CompletionEntryDataAutoImport,
+  normalized: ModuleSpecifier,
+}
+
 #[derive(Debug, Default, Deserialize, Serialize)]
 #[serde(rename_all = "camelCase")]
 pub struct CompletionEntry {
@@ -3682,9 +3756,28 @@ pub struct CompletionEntry {
   is_import_statement_completion: Option<bool>,
   #[serde(skip_serializing_if = "Option::is_none")]
   data: Option<Value>,
+  /// This is not from tsc, we add it for convenience during normalization.
+  /// Represents `self.data.file_name`, but normalized.
+  #[serde(skip)]
+  auto_import_data: Option<CompletionNormalizedAutoImportData>,
 }
 
 impl CompletionEntry {
+  fn normalize(&mut self, specifier_map: &TscSpecifierMap) {
+    let Some(data) = &self.data else {
+      return;
+    };
+    let Ok(raw) =
+      serde_json::from_value::<CompletionEntryDataAutoImport>(data.clone())
+    else {
+      return;
+    };
+    if let Ok(normalized) = specifier_map.normalize(&raw.file_name) {
+      self.auto_import_data =
+        Some(CompletionNormalizedAutoImportData { raw, normalized });
+    }
+  }
+
   fn get_commit_characters(
     &self,
     info: &CompletionInfo,
@@ -3833,25 +3926,24 @@ impl CompletionEntry {
 
     if let Some(source) = &self.source {
       let mut display_source = source.clone();
-      if let Some(data) = &self.data {
-        if let Ok(import_data) =
-          serde_json::from_value::<CompletionEntryDataImport>(data.clone())
+      if let Some(import_data) = &self.auto_import_data {
+        if let Some(new_module_specifier) = language_server
+          .get_ts_response_import_mapper(specifier)
+          .check_specifier(&import_data.normalized, specifier)
+          .or_else(|| relative_specifier(specifier, &import_data.normalized))
         {
-          if let Ok(import_specifier) = resolve_url(&import_data.file_name) {
-            if let Some(new_module_specifier) = language_server
-              .get_ts_response_import_mapper(specifier)
-              .check_specifier(&import_specifier, specifier)
-              .or_else(|| relative_specifier(specifier, &import_specifier))
-            {
-              display_source.clone_from(&new_module_specifier);
-              if new_module_specifier != import_data.module_specifier {
-                specifier_rewrite =
-                  Some((import_data.module_specifier, new_module_specifier));
-              }
-            } else if source.starts_with(jsr_url().as_str()) {
-              return None;
-            }
+          if new_module_specifier.contains("/node_modules/") {
+            return None;
           }
+          display_source.clone_from(&new_module_specifier);
+          if new_module_specifier != import_data.raw.module_specifier {
+            specifier_rewrite = Some((
+              import_data.raw.module_specifier.clone(),
+              new_module_specifier,
+            ));
+          }
+        } else if source.starts_with(jsr_url().as_str()) {
+          return None;
         }
       }
       // We want relative or bare (import-mapped or otherwise) specifiers to
@@ -3939,7 +4031,7 @@ pub struct OutliningSpan {
   kind: OutliningSpanKind,
 }
 
-const FOLD_END_PAIR_CHARACTERS: &[u8] = &[b'}', b']', b')', b'`'];
+const FOLD_END_PAIR_CHARACTERS: &[u8] = b"}])`";
 
 impl OutliningSpan {
   pub fn to_folding_range(
@@ -4154,6 +4246,13 @@ impl TscSpecifierMap {
       return specifier.to_string();
     }
     let mut specifier = original.to_string();
+    if specifier.contains("/node_modules/.deno/")
+      && !specifier.contains("/node_modules/@types/node/")
+    {
+      // The ts server doesn't give completions from files in
+      // `node_modules/.deno/`. We work around it like this.
+      specifier = specifier.replace("/node_modules/", "/$node_modules/");
+    }
     let media_type = MediaType::from_specifier(original);
     // If the URL-inferred media type doesn't correspond to tsc's path-inferred
     // media type, force it to be the same by appending an extension.
@@ -4271,7 +4370,7 @@ fn op_is_cancelled(state: &mut OpState) -> bool {
 fn op_is_node_file(state: &mut OpState, #[string] path: String) -> bool {
   let state = state.borrow::<State>();
   let mark = state.performance.mark("tsc.op.op_is_node_file");
-  let r = match ModuleSpecifier::parse(&path) {
+  let r = match state.specifier_map.normalize(path) {
     Ok(specifier) => state.state_snapshot.resolver.in_node_modules(&specifier),
     Err(_) => false,
   };
@@ -4308,10 +4407,11 @@ fn op_load<'s>(
         data: doc.text(),
         script_kind: crate::tsc::as_ts_script_kind(doc.media_type()),
         version: state.script_version(&specifier),
-        is_cjs: matches!(
-          doc.media_type(),
-          MediaType::Cjs | MediaType::Cts | MediaType::Dcts
-        ),
+        is_cjs: doc
+          .document()
+          .map(|d| state.state_snapshot.is_cjs_resolver.get_doc_module_kind(d))
+          .unwrap_or(NodeModuleKind::Esm)
+          == NodeModuleKind::Cjs,
       })
     };
 
@@ -4540,7 +4640,10 @@ fn op_script_names(state: &mut OpState) -> ScriptNames {
   for doc in &docs {
     let specifier = doc.specifier();
     let is_open = doc.is_open();
-    if is_open || specifier.scheme() == "file" {
+    if is_open
+      || (specifier.scheme() == "file"
+        && !state.state_snapshot.resolver.in_node_modules(specifier))
+    {
       let script_names = doc
         .scope()
         .and_then(|s| result.by_scope.get_mut(s))
@@ -4551,6 +4654,10 @@ fn op_script_names(state: &mut OpState) -> ScriptNames {
         let (types, _) = documents.resolve_dependency(
           types,
           specifier,
+          state
+            .state_snapshot
+            .is_cjs_resolver
+            .get_doc_module_kind(doc),
           doc.file_referrer(),
         )?;
         let types_doc = documents.get_or_load(&types, doc.file_referrer())?;
@@ -4654,6 +4761,7 @@ fn run_tsc_thread(
       specifier_map,
       request_rx,
     )],
+    create_params: create_isolate_create_params(),
     startup_snapshot: Some(tsc::compiler_snapshot()),
     inspector: has_inspector_server,
     ..Default::default()
@@ -4892,6 +5000,10 @@ pub struct UserPreferences {
   pub allow_rename_of_import_path: Option<bool>,
   #[serde(skip_serializing_if = "Option::is_none")]
   pub auto_import_file_exclude_patterns: Option<Vec<String>>,
+  #[serde(skip_serializing_if = "Option::is_none")]
+  pub interactive_inlay_hints: Option<bool>,
+  #[serde(skip_serializing_if = "Option::is_none")]
+  pub prefer_type_only_auto_imports: Option<bool>,
 }
 
 impl UserPreferences {
@@ -4909,6 +5021,7 @@ impl UserPreferences {
       include_completions_with_snippet_text: Some(
         config.snippet_support_capable(),
       ),
+      interactive_inlay_hints: Some(true),
       provide_refactor_not_applicable_reason: Some(true),
       quote_preference: Some(fmt_config.into()),
       use_label_details_in_completion_entries: Some(true),
@@ -5013,6 +5126,9 @@ impl UserPreferences {
       } else {
         Some(language_settings.preferences.quote_style)
       },
+      prefer_type_only_auto_imports: Some(
+        language_settings.preferences.prefer_type_only_auto_imports,
+      ),
       ..base_preferences
     }
   }
@@ -5425,6 +5541,7 @@ mod tests {
       documents: Arc::new(documents),
       assets: Default::default(),
       config: Arc::new(config),
+      is_cjs_resolver: Default::default(),
       resolver,
     });
     let performance = Arc::new(Performance::default());
@@ -5958,6 +6075,7 @@ mod tests {
         Some(temp_dir.url()),
       )
       .await
+      .unwrap()
       .unwrap();
     assert_eq!(info.entries.len(), 22);
     let details = ts_server
@@ -6117,6 +6235,7 @@ mod tests {
         Some(temp_dir.url()),
       )
       .await
+      .unwrap()
       .unwrap();
     let entry = info
       .entries
@@ -6154,7 +6273,7 @@ mod tests {
     let change = changes.text_changes.first().unwrap();
     assert_eq!(
       change.new_text,
-      "import type { someLongVariable } from './b.ts'\n"
+      "import { someLongVariable } from './b.ts'\n"
     );
   }
 
diff --git a/cli/main.rs b/cli/main.rs
index c0eccab5df..7d3ef0e6a0 100644
--- a/cli/main.rs
+++ b/cli/main.rs
@@ -15,7 +15,6 @@ mod js;
 mod jsr;
 mod lsp;
 mod module_loader;
-mod napi;
 mod node;
 mod npm;
 mod ops;
@@ -37,6 +36,8 @@ use crate::util::v8::get_v8_flags_from_env;
 use crate::util::v8::init_v8_flags;
 
 use args::TaskFlags;
+use deno_resolver::npm::ByonmResolvePkgFolderFromDenoReqError;
+use deno_resolver::npm::ResolvePkgFolderFromDenoReqError;
 use deno_runtime::WorkerExecutionMode;
 pub use deno_runtime::UNSTABLE_GRANULAR_FLAGS;
 
@@ -46,8 +47,7 @@ use deno_core::error::JsError;
 use deno_core::futures::FutureExt;
 use deno_core::unsync::JoinHandle;
 use deno_npm::resolution::SnapshotFromLockfileError;
-use deno_runtime::fmt_errors::format_js_error_with_suggestions;
-use deno_runtime::fmt_errors::FixSuggestion;
+use deno_runtime::fmt_errors::format_js_error;
 use deno_runtime::tokio_util::create_and_run_current_thread_with_maybe_metrics;
 use deno_terminal::colors;
 use factory::CliFactory;
@@ -55,10 +55,15 @@ use standalone::MODULE_NOT_FOUND;
 use standalone::UNSUPPORTED_SCHEME;
 use std::env;
 use std::future::Future;
+use std::io::IsTerminal;
 use std::ops::Deref;
 use std::path::PathBuf;
 use std::sync::Arc;
 
+#[cfg(feature = "dhat-heap")]
+#[global_allocator]
+static ALLOC: dhat::Alloc = dhat::Alloc;
+
 /// Ensures that all subcommands return an i32 exit code and an [`AnyError`] error type.
 trait SubcommandOutput {
   fn output(self) -> Result<i32, AnyError>;
@@ -130,7 +135,7 @@ async fn run_subcommand(flags: Arc<Flags>) -> Result<i32, AnyError> {
       tools::compile::compile(flags, compile_flags).await
     }),
     DenoSubcommand::Coverage(coverage_flags) => spawn_subcommand(async {
-      tools::coverage::cover_files(flags, coverage_flags).await
+      tools::coverage::cover_files(flags, coverage_flags)
     }),
     DenoSubcommand::Fmt(fmt_flags) => {
       spawn_subcommand(
@@ -159,7 +164,19 @@ async fn run_subcommand(flags: Arc<Flags>) -> Result<i32, AnyError> {
     DenoSubcommand::Uninstall(uninstall_flags) => spawn_subcommand(async {
       tools::installer::uninstall(flags, uninstall_flags).await
     }),
-    DenoSubcommand::Lsp => spawn_subcommand(async { lsp::start().await }),
+    DenoSubcommand::Lsp => spawn_subcommand(async {
+      if std::io::stderr().is_terminal() {
+        log::warn!(
+          "{} command is intended to be run by text editors and IDEs and shouldn't be run manually.
+
+  Visit https://docs.deno.com/runtime/getting_started/setup_your_environment/ for instruction
+  how to setup your favorite text editor.
+
+  Press Ctrl+C to exit.
+        ", colors::cyan("deno lsp"));
+      }
+      lsp::start().await
+    }),
     DenoSubcommand::Lint(lint_flags) => spawn_subcommand(async {
       if lint_flags.rules {
         tools::lint::print_rules_list(
@@ -182,6 +199,21 @@ async fn run_subcommand(flags: Arc<Flags>) -> Result<i32, AnyError> {
         match result {
           Ok(v) => Ok(v),
           Err(script_err) => {
+            if let Some(ResolvePkgFolderFromDenoReqError::Byonm(ByonmResolvePkgFolderFromDenoReqError::UnmatchedReq(_))) = script_err.downcast_ref::<ResolvePkgFolderFromDenoReqError>() {
+              if flags.node_modules_dir.is_none() {
+                let mut flags = flags.deref().clone();
+                let watch = match &flags.subcommand {
+                  DenoSubcommand::Run(run_flags) => run_flags.watch.clone(),
+                  _ => unreachable!(),
+                };
+                flags.node_modules_dir = Some(deno_config::deno_json::NodeModulesDirMode::None);
+                // use the current lockfile, but don't write it out
+                if flags.frozen_lockfile.is_none() {
+                  flags.internal.lockfile_skip_write = true;
+                }
+                return tools::run::run_script(WorkerExecutionMode::Run, Arc::new(flags), watch).await;
+              }
+            }
             let script_err_msg = script_err.to_string();
             if script_err_msg.starts_with(MODULE_NOT_FOUND) || script_err_msg.starts_with(UNSUPPORTED_SCHEME) {
               if run_flags.bare {
@@ -318,84 +350,17 @@ fn setup_panic_hook() {
     eprintln!("Args: {:?}", env::args().collect::<Vec<_>>());
     eprintln!();
     orig_hook(panic_info);
-    std::process::exit(1);
+    deno_runtime::exit(1);
   }));
 }
 
-#[allow(clippy::print_stderr)]
 fn exit_with_message(message: &str, code: i32) -> ! {
-  eprintln!(
+  log::error!(
     "{}: {}",
     colors::red_bold("error"),
     message.trim_start_matches("error: ")
   );
-  std::process::exit(code);
-}
-
-fn get_suggestions_for_terminal_errors(e: &JsError) -> Vec<FixSuggestion> {
-  if let Some(msg) = &e.message {
-    if msg.contains("module is not defined")
-      || msg.contains("exports is not defined")
-    {
-      return vec![
-        FixSuggestion::info(
-          "Deno does not support CommonJS modules without `.cjs` extension.",
-        ),
-        FixSuggestion::hint(
-          "Rewrite this module to ESM or change the file extension to `.cjs`.",
-        ),
-      ];
-    } else if msg.contains("openKv is not a function") {
-      return vec![
-        FixSuggestion::info("Deno.openKv() is an unstable API."),
-        FixSuggestion::hint(
-          "Run again with `--unstable-kv` flag to enable this API.",
-        ),
-      ];
-    } else if msg.contains("cron is not a function") {
-      return vec![
-        FixSuggestion::info("Deno.cron() is an unstable API."),
-        FixSuggestion::hint(
-          "Run again with `--unstable-cron` flag to enable this API.",
-        ),
-      ];
-    } else if msg.contains("WebSocketStream is not defined") {
-      return vec![
-        FixSuggestion::info("new WebSocketStream() is an unstable API."),
-        FixSuggestion::hint(
-          "Run again with `--unstable-net` flag to enable this API.",
-        ),
-      ];
-    } else if msg.contains("Temporal is not defined") {
-      return vec![
-        FixSuggestion::info("Temporal is an unstable API."),
-        FixSuggestion::hint(
-          "Run again with `--unstable-temporal` flag to enable this API.",
-        ),
-      ];
-    } else if msg.contains("BroadcastChannel is not defined") {
-      return vec![
-        FixSuggestion::info("BroadcastChannel is an unstable API."),
-        FixSuggestion::hint(
-          "Run again with `--unstable-broadcast-channel` flag to enable this API.",
-        ),
-      ];
-    } else if msg.contains("window is not defined") {
-      return vec![
-        FixSuggestion::info("window global is not available in Deno 2."),
-        FixSuggestion::hint("Replace `window` with `globalThis`."),
-      ];
-    } else if msg.contains("UnsafeWindowSurface is not a constructor") {
-      return vec![
-        FixSuggestion::info("Deno.UnsafeWindowSurface is an unstable API."),
-        FixSuggestion::hint(
-          "Run again with `--unstable-webgpu` flag to enable this API.",
-        ),
-      ];
-    }
-  }
-
-  vec![]
+  deno_runtime::exit(code);
 }
 
 fn exit_for_error(error: AnyError) -> ! {
@@ -403,8 +368,7 @@ fn exit_for_error(error: AnyError) -> ! {
   let mut error_code = 1;
 
   if let Some(e) = error.downcast_ref::<JsError>() {
-    let suggestions = get_suggestions_for_terminal_errors(e);
-    error_string = format_js_error_with_suggestions(e, suggestions);
+    error_string = format_js_error(e);
   } else if let Some(SnapshotFromLockfileError::IntegrityCheckFailed(e)) =
     error.downcast_ref::<SnapshotFromLockfileError>()
   {
@@ -415,16 +379,18 @@ fn exit_for_error(error: AnyError) -> ! {
   exit_with_message(&error_string, error_code);
 }
 
-#[allow(clippy::print_stderr)]
 pub(crate) fn unstable_exit_cb(feature: &str, api_name: &str) {
-  eprintln!(
+  log::error!(
     "Unstable API '{api_name}'. The `--unstable-{}` flag must be provided.",
     feature
   );
-  std::process::exit(70);
+  deno_runtime::exit(70);
 }
 
 pub fn main() {
+  #[cfg(feature = "dhat-heap")]
+  let profiler = dhat::Profiler::new_heap();
+
   setup_panic_hook();
 
   util::unix::raise_fd_limit();
@@ -445,8 +411,13 @@ pub fn main() {
     run_subcommand(Arc::new(flags)).await
   };
 
-  match create_and_run_current_thread_with_maybe_metrics(future) {
-    Ok(exit_code) => std::process::exit(exit_code),
+  let result = create_and_run_current_thread_with_maybe_metrics(future);
+
+  #[cfg(feature = "dhat-heap")]
+  drop(profiler);
+
+  match result {
+    Ok(exit_code) => deno_runtime::exit(exit_code),
     Err(err) => exit_for_error(err),
   }
 }
@@ -460,12 +431,21 @@ fn resolve_flags_and_init(
       if err.kind() == clap::error::ErrorKind::DisplayVersion =>
     {
       // Ignore results to avoid BrokenPipe errors.
+      util::logger::init(None);
       let _ = err.print();
-      std::process::exit(0);
+      deno_runtime::exit(0);
+    }
+    Err(err) => {
+      util::logger::init(None);
+      exit_for_error(AnyError::from(err))
     }
-    Err(err) => exit_for_error(AnyError::from(err)),
   };
 
+  if let Some(otel_config) = flags.otel_config() {
+    deno_runtime::ops::otel::init(otel_config)?;
+  }
+  util::logger::init(flags.log_level);
+
   // TODO(bartlomieju): remove in Deno v2.5 and hard error then.
   if flags.unstable_config.legacy_flag_enabled {
     log::warn!(
@@ -494,7 +474,6 @@ fn resolve_flags_and_init(
   deno_core::JsRuntime::init_platform(
     None, /* import assertions enabled */ false,
   );
-  util::logger::init(flags.log_level);
 
   Ok(flags)
 }
diff --git a/cli/mainrt.rs b/cli/mainrt.rs
index 02d58fcee1..2951aa711a 100644
--- a/cli/mainrt.rs
+++ b/cli/mainrt.rs
@@ -40,23 +40,21 @@ use std::env::current_exe;
 
 use crate::args::Flags;
 
-#[allow(clippy::print_stderr)]
 pub(crate) fn unstable_exit_cb(feature: &str, api_name: &str) {
-  eprintln!(
+  log::error!(
     "Unstable API '{api_name}'. The `--unstable-{}` flag must be provided.",
     feature
   );
-  std::process::exit(70);
+  deno_runtime::exit(70);
 }
 
-#[allow(clippy::print_stderr)]
 fn exit_with_message(message: &str, code: i32) -> ! {
-  eprintln!(
+  log::error!(
     "{}: {}",
     colors::red_bold("error"),
     message.trim_start_matches("error: ")
   );
-  std::process::exit(code);
+  deno_runtime::exit(code);
 }
 
 fn unwrap_or_exit<T>(result: Result<T, AnyError>) -> T {
@@ -88,15 +86,20 @@ fn main() {
   let standalone = standalone::extract_standalone(Cow::Owned(args));
   let future = async move {
     match standalone {
-      Ok(Some(future)) => {
-        let (metadata, eszip) = future.await?;
-        util::logger::init(metadata.log_level);
-        load_env_vars(&metadata.env_vars_from_env_file);
-        let exit_code = standalone::run(eszip, metadata).await?;
-        std::process::exit(exit_code);
+      Ok(Some(data)) => {
+        if let Some(otel_config) = data.metadata.otel_config.clone() {
+          deno_runtime::ops::otel::init(otel_config)?;
+        }
+        util::logger::init(data.metadata.log_level);
+        load_env_vars(&data.metadata.env_vars_from_env_file);
+        let exit_code = standalone::run(data).await?;
+        deno_runtime::exit(exit_code);
       }
       Ok(None) => Ok(()),
-      Err(err) => Err(err),
+      Err(err) => {
+        util::logger::init(None);
+        Err(err)
+      }
     }
   };
 
diff --git a/cli/module_loader.rs b/cli/module_loader.rs
index f4e219bea1..b9adfe642c 100644
--- a/cli/module_loader.rs
+++ b/cli/module_loader.rs
@@ -2,6 +2,7 @@
 
 use std::borrow::Cow;
 use std::cell::RefCell;
+use std::path::Path;
 use std::path::PathBuf;
 use std::pin::Pin;
 use std::rc::Rc;
@@ -23,18 +24,23 @@ use crate::graph_container::ModuleGraphUpdatePermit;
 use crate::graph_util::CreateGraphOptions;
 use crate::graph_util::ModuleGraphBuilder;
 use crate::node;
-use crate::resolver::CliGraphResolver;
-use crate::resolver::CliNodeResolver;
+use crate::node::CliNodeCodeTranslator;
+use crate::npm::CliNpmResolver;
+use crate::resolver::CjsTracker;
+use crate::resolver::CliNpmReqResolver;
+use crate::resolver::CliResolver;
 use crate::resolver::ModuleCodeStringSource;
+use crate::resolver::NotSupportedKindInNpmError;
 use crate::resolver::NpmModuleLoader;
 use crate::tools::check;
 use crate::tools::check::TypeChecker;
 use crate::util::progress_bar::ProgressBar;
 use crate::util::text_encoding::code_without_source_map;
 use crate::util::text_encoding::source_map_from_code;
-use crate::worker::ModuleLoaderAndSourceMapGetter;
+use crate::worker::CreateModuleLoaderResult;
 use crate::worker::ModuleLoaderFactory;
 use deno_ast::MediaType;
+use deno_ast::ModuleKind;
 use deno_core::anyhow::anyhow;
 use deno_core::anyhow::bail;
 use deno_core::anyhow::Context;
@@ -54,7 +60,6 @@ use deno_core::RequestedModuleType;
 use deno_core::ResolutionKind;
 use deno_core::SourceCodeCacheInfo;
 use deno_graph::source::ResolutionMode;
-use deno_graph::source::Resolver;
 use deno_graph::GraphKind;
 use deno_graph::JsModule;
 use deno_graph::JsonModule;
@@ -62,9 +67,14 @@ use deno_graph::Module;
 use deno_graph::ModuleGraph;
 use deno_graph::Resolution;
 use deno_runtime::code_cache;
+use deno_runtime::deno_fs::FileSystem;
 use deno_runtime::deno_node::create_host_defined_options;
+use deno_runtime::deno_node::NodeRequireLoader;
+use deno_runtime::deno_node::NodeResolver;
 use deno_runtime::deno_permissions::PermissionsContainer;
 use deno_semver::npm::NpmPackageReqReference;
+use node_resolver::errors::ClosestPkgJsonError;
+use node_resolver::InNpmPackageChecker;
 use node_resolver::NodeResolutionMode;
 
 pub struct ModuleLoadPreparer {
@@ -198,14 +208,20 @@ struct SharedCliModuleLoaderState {
   initial_cwd: PathBuf,
   is_inspecting: bool,
   is_repl: bool,
+  cjs_tracker: Arc<CjsTracker>,
   code_cache: Option<Arc<CodeCache>>,
   emitter: Arc<Emitter>,
+  fs: Arc<dyn FileSystem>,
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
   main_module_graph_container: Arc<MainModuleGraphContainer>,
   module_load_preparer: Arc<ModuleLoadPreparer>,
-  node_resolver: Arc<CliNodeResolver>,
+  node_code_translator: Arc<CliNodeCodeTranslator>,
+  node_resolver: Arc<NodeResolver>,
+  npm_req_resolver: Arc<CliNpmReqResolver>,
+  npm_resolver: Arc<dyn CliNpmResolver>,
   npm_module_loader: NpmModuleLoader,
   parsed_source_cache: Arc<ParsedSourceCache>,
-  resolver: Arc<CliGraphResolver>,
+  resolver: Arc<CliResolver>,
 }
 
 pub struct CliModuleLoaderFactory {
@@ -216,14 +232,20 @@ impl CliModuleLoaderFactory {
   #[allow(clippy::too_many_arguments)]
   pub fn new(
     options: &CliOptions,
+    cjs_tracker: Arc<CjsTracker>,
     code_cache: Option<Arc<CodeCache>>,
     emitter: Arc<Emitter>,
+    fs: Arc<dyn FileSystem>,
+    in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
     main_module_graph_container: Arc<MainModuleGraphContainer>,
     module_load_preparer: Arc<ModuleLoadPreparer>,
-    node_resolver: Arc<CliNodeResolver>,
+    node_code_translator: Arc<CliNodeCodeTranslator>,
+    node_resolver: Arc<NodeResolver>,
+    npm_req_resolver: Arc<CliNpmReqResolver>,
+    npm_resolver: Arc<dyn CliNpmResolver>,
     npm_module_loader: NpmModuleLoader,
     parsed_source_cache: Arc<ParsedSourceCache>,
-    resolver: Arc<CliGraphResolver>,
+    resolver: Arc<CliResolver>,
   ) -> Self {
     Self {
       shared: Arc::new(SharedCliModuleLoaderState {
@@ -236,11 +258,17 @@ impl CliModuleLoaderFactory {
           options.sub_command(),
           DenoSubcommand::Repl(_) | DenoSubcommand::Jupyter(_)
         ),
+        cjs_tracker,
         code_cache,
         emitter,
+        fs,
+        in_npm_pkg_checker,
         main_module_graph_container,
         module_load_preparer,
+        node_code_translator,
         node_resolver,
+        npm_req_resolver,
+        npm_resolver,
         npm_module_loader,
         parsed_source_cache,
         resolver,
@@ -255,19 +283,30 @@ impl CliModuleLoaderFactory {
     is_worker: bool,
     parent_permissions: PermissionsContainer,
     permissions: PermissionsContainer,
-  ) -> ModuleLoaderAndSourceMapGetter {
-    let loader = Rc::new(CliModuleLoader(Rc::new(CliModuleLoaderInner {
-      lib,
-      is_worker,
-      parent_permissions,
-      permissions,
-      graph_container,
+  ) -> CreateModuleLoaderResult {
+    let module_loader =
+      Rc::new(CliModuleLoader(Rc::new(CliModuleLoaderInner {
+        lib,
+        is_worker,
+        parent_permissions,
+        permissions,
+        graph_container: graph_container.clone(),
+        node_code_translator: self.shared.node_code_translator.clone(),
+        emitter: self.shared.emitter.clone(),
+        parsed_source_cache: self.shared.parsed_source_cache.clone(),
+        shared: self.shared.clone(),
+      })));
+    let node_require_loader = Rc::new(CliNodeRequireLoader {
+      cjs_tracker: self.shared.cjs_tracker.clone(),
       emitter: self.shared.emitter.clone(),
-      parsed_source_cache: self.shared.parsed_source_cache.clone(),
-      shared: self.shared.clone(),
-    })));
-    ModuleLoaderAndSourceMapGetter {
-      module_loader: loader,
+      fs: self.shared.fs.clone(),
+      graph_container,
+      in_npm_pkg_checker: self.shared.in_npm_pkg_checker.clone(),
+      npm_resolver: self.shared.npm_resolver.clone(),
+    });
+    CreateModuleLoaderResult {
+      module_loader,
+      node_require_loader,
     }
   }
 }
@@ -276,7 +315,7 @@ impl ModuleLoaderFactory for CliModuleLoaderFactory {
   fn create_for_main(
     &self,
     root_permissions: PermissionsContainer,
-  ) -> ModuleLoaderAndSourceMapGetter {
+  ) -> CreateModuleLoaderResult {
     self.create_with_lib(
       (*self.shared.main_module_graph_container).clone(),
       self.shared.lib_window,
@@ -290,7 +329,7 @@ impl ModuleLoaderFactory for CliModuleLoaderFactory {
     &self,
     parent_permissions: PermissionsContainer,
     permissions: PermissionsContainer,
-  ) -> ModuleLoaderAndSourceMapGetter {
+  ) -> CreateModuleLoaderResult {
     self.create_with_lib(
       // create a fresh module graph for the worker
       WorkerModuleGraphContainer::new(Arc::new(ModuleGraph::new(
@@ -314,6 +353,7 @@ struct CliModuleLoaderInner<TGraphContainer: ModuleGraphContainer> {
   permissions: PermissionsContainer,
   shared: Arc<SharedCliModuleLoaderState>,
   emitter: Arc<Emitter>,
+  node_code_translator: Arc<CliNodeCodeTranslator>,
   parsed_source_cache: Arc<ParsedSourceCache>,
   graph_container: TGraphContainer,
 }
@@ -327,16 +367,7 @@ impl<TGraphContainer: ModuleGraphContainer>
     maybe_referrer: Option<&ModuleSpecifier>,
     requested_module_type: RequestedModuleType,
   ) -> Result<ModuleSource, AnyError> {
-    let code_source = if let Some(result) = self
-      .shared
-      .npm_module_loader
-      .load_if_in_npm_package(specifier, maybe_referrer)
-      .await
-    {
-      result?
-    } else {
-      self.load_prepared_module(specifier, maybe_referrer).await?
-    };
+    let code_source = self.load_code_source(specifier, maybe_referrer).await?;
     let code = if self.shared.is_inspecting {
       // we need the code with the source map in order for
       // it to work with --inspect or --inspect-brk
@@ -390,6 +421,29 @@ impl<TGraphContainer: ModuleGraphContainer>
     ))
   }
 
+  async fn load_code_source(
+    &self,
+    specifier: &ModuleSpecifier,
+    maybe_referrer: Option<&ModuleSpecifier>,
+  ) -> Result<ModuleCodeStringSource, AnyError> {
+    if let Some(code_source) = self.load_prepared_module(specifier).await? {
+      return Ok(code_source);
+    }
+    if self.shared.in_npm_pkg_checker.in_npm_package(specifier) {
+      return self
+        .shared
+        .npm_module_loader
+        .load(specifier, maybe_referrer)
+        .await;
+    }
+
+    let mut msg = format!("Loading unprepared module: {specifier}");
+    if let Some(referrer) = maybe_referrer {
+      msg = format!("{}, imported from: {}", msg, referrer.as_str());
+    }
+    Err(anyhow!(msg))
+  }
+
   fn resolve_referrer(
     &self,
     referrer: &str,
@@ -397,7 +451,7 @@ impl<TGraphContainer: ModuleGraphContainer>
     let referrer = if referrer.is_empty() && self.shared.is_repl {
       // FIXME(bartlomieju): this is a hacky way to provide compatibility with REPL
       // and `Deno.core.evalContext` API. Ideally we should always have a referrer filled
-      "./$deno$repl.ts"
+      "./$deno$repl.mts"
     } else {
       referrer
     };
@@ -420,12 +474,17 @@ impl<TGraphContainer: ModuleGraphContainer>
     raw_specifier: &str,
     referrer: &ModuleSpecifier,
   ) -> Result<ModuleSpecifier, AnyError> {
-    if self.shared.node_resolver.in_npm_package(referrer) {
+    if self.shared.in_npm_pkg_checker.in_npm_package(referrer) {
       return Ok(
         self
           .shared
           .node_resolver
-          .resolve(raw_specifier, referrer, NodeResolutionMode::Execution)?
+          .resolve(
+            raw_specifier,
+            referrer,
+            self.shared.cjs_tracker.get_referrer_kind(referrer),
+            NodeResolutionMode::Execution,
+          )?
           .into_url(),
       );
     }
@@ -455,6 +514,7 @@ impl<TGraphContainer: ModuleGraphContainer>
           start: deno_graph::Position::zeroed(),
           end: deno_graph::Position::zeroed(),
         },
+        self.shared.cjs_tracker.get_referrer_kind(referrer),
         ResolutionMode::Execution,
       )?),
     };
@@ -464,13 +524,14 @@ impl<TGraphContainer: ModuleGraphContainer>
       {
         return self
           .shared
-          .node_resolver
+          .npm_req_resolver
           .resolve_req_reference(
             &reference,
             referrer,
+            self.shared.cjs_tracker.get_referrer_kind(referrer),
             NodeResolutionMode::Execution,
           )
-          .map(|res| res.into_url());
+          .map_err(AnyError::from);
       }
     }
 
@@ -478,7 +539,6 @@ impl<TGraphContainer: ModuleGraphContainer>
       Some(Module::Npm(module)) => {
         let package_folder = self
           .shared
-          .node_resolver
           .npm_resolver
           .as_managed()
           .unwrap() // byonm won't create a Module::Npm
@@ -486,22 +546,25 @@ impl<TGraphContainer: ModuleGraphContainer>
         self
           .shared
           .node_resolver
-          .resolve_package_sub_path_from_deno_module(
+          .resolve_package_subpath_from_deno_module(
             &package_folder,
             module.nv_reference.sub_path(),
             Some(referrer),
+            self.shared.cjs_tracker.get_referrer_kind(referrer),
             NodeResolutionMode::Execution,
           )
           .with_context(|| {
             format!("Could not resolve '{}'.", module.nv_reference)
           })?
-          .into_url()
       }
       Some(Module::Node(module)) => module.specifier.clone(),
       Some(Module::Js(module)) => module.specifier.clone(),
       Some(Module::Json(module)) => module.specifier.clone(),
       Some(Module::External(module)) => {
-        node::resolve_specifier_into_node_modules(&module.specifier)
+        node::resolve_specifier_into_node_modules(
+          &module.specifier,
+          self.shared.fs.as_ref(),
+        )
       }
       None => specifier.into_owned(),
     };
@@ -511,71 +574,82 @@ impl<TGraphContainer: ModuleGraphContainer>
   async fn load_prepared_module(
     &self,
     specifier: &ModuleSpecifier,
-    maybe_referrer: Option<&ModuleSpecifier>,
-  ) -> Result<ModuleCodeStringSource, AnyError> {
+  ) -> Result<Option<ModuleCodeStringSource>, AnyError> {
     // Note: keep this in sync with the sync version below
     let graph = self.graph_container.graph();
-    match self.load_prepared_module_or_defer_emit(
-      &graph,
-      specifier,
-      maybe_referrer,
-    ) {
-      Ok(CodeOrDeferredEmit::Code(code_source)) => Ok(code_source),
-      Ok(CodeOrDeferredEmit::DeferredEmit {
+    match self.load_prepared_module_or_defer_emit(&graph, specifier)? {
+      Some(CodeOrDeferredEmit::Code(code_source)) => Ok(Some(code_source)),
+      Some(CodeOrDeferredEmit::DeferredEmit {
         specifier,
         media_type,
         source,
       }) => {
         let transpile_result = self
           .emitter
-          .emit_parsed_source(specifier, media_type, source)
+          .emit_parsed_source(specifier, media_type, ModuleKind::Esm, source)
           .await?;
 
         // at this point, we no longer need the parsed source in memory, so free it
         self.parsed_source_cache.free(specifier);
 
-        Ok(ModuleCodeStringSource {
-          code: ModuleSourceCode::Bytes(transpile_result),
+        Ok(Some(ModuleCodeStringSource {
+          // note: it's faster to provide a string if we know it's a string
+          code: ModuleSourceCode::String(transpile_result.into()),
           found_url: specifier.clone(),
           media_type,
-        })
+        }))
       }
-      Err(err) => Err(err),
+      Some(CodeOrDeferredEmit::Cjs {
+        specifier,
+        media_type,
+        source,
+      }) => self
+        .load_maybe_cjs(specifier, media_type, source)
+        .await
+        .map(Some),
+      None => Ok(None),
     }
   }
 
-  fn load_prepared_module_sync(
+  fn load_prepared_module_for_source_map_sync(
     &self,
     specifier: &ModuleSpecifier,
-    maybe_referrer: Option<&ModuleSpecifier>,
-  ) -> Result<ModuleCodeStringSource, AnyError> {
+  ) -> Result<Option<ModuleCodeStringSource>, AnyError> {
     // Note: keep this in sync with the async version above
     let graph = self.graph_container.graph();
-    match self.load_prepared_module_or_defer_emit(
-      &graph,
-      specifier,
-      maybe_referrer,
-    ) {
-      Ok(CodeOrDeferredEmit::Code(code_source)) => Ok(code_source),
-      Ok(CodeOrDeferredEmit::DeferredEmit {
+    match self.load_prepared_module_or_defer_emit(&graph, specifier)? {
+      Some(CodeOrDeferredEmit::Code(code_source)) => Ok(Some(code_source)),
+      Some(CodeOrDeferredEmit::DeferredEmit {
         specifier,
         media_type,
         source,
       }) => {
-        let transpile_result = self
-          .emitter
-          .emit_parsed_source_sync(specifier, media_type, source)?;
+        let transpile_result = self.emitter.emit_parsed_source_sync(
+          specifier,
+          media_type,
+          ModuleKind::Esm,
+          source,
+        )?;
 
         // at this point, we no longer need the parsed source in memory, so free it
         self.parsed_source_cache.free(specifier);
 
-        Ok(ModuleCodeStringSource {
-          code: ModuleSourceCode::Bytes(transpile_result),
+        Ok(Some(ModuleCodeStringSource {
+          // note: it's faster to provide a string if we know it's a string
+          code: ModuleSourceCode::String(transpile_result.into()),
           found_url: specifier.clone(),
           media_type,
-        })
+        }))
       }
-      Err(err) => Err(err),
+      Some(CodeOrDeferredEmit::Cjs { .. }) => {
+        self.parsed_source_cache.free(specifier);
+
+        // todo(dsherret): to make this work, we should probably just
+        // rely on the CJS export cache. At the moment this is hard because
+        // cjs export analysis is only async
+        Ok(None)
+      }
+      None => Ok(None),
     }
   }
 
@@ -583,8 +657,7 @@ impl<TGraphContainer: ModuleGraphContainer>
     &self,
     graph: &'graph ModuleGraph,
     specifier: &ModuleSpecifier,
-    maybe_referrer: Option<&ModuleSpecifier>,
-  ) -> Result<CodeOrDeferredEmit<'graph>, AnyError> {
+  ) -> Result<Option<CodeOrDeferredEmit<'graph>>, AnyError> {
     if specifier.scheme() == "node" {
       // Node built-in modules should be handled internally.
       unreachable!("Deno bug. {} was misconfigured internally.", specifier);
@@ -596,38 +669,55 @@ impl<TGraphContainer: ModuleGraphContainer>
         media_type,
         specifier,
         ..
-      })) => Ok(CodeOrDeferredEmit::Code(ModuleCodeStringSource {
+      })) => Ok(Some(CodeOrDeferredEmit::Code(ModuleCodeStringSource {
         code: ModuleSourceCode::String(source.clone().into()),
         found_url: specifier.clone(),
         media_type: *media_type,
-      })),
+      }))),
       Some(deno_graph::Module::Js(JsModule {
         source,
         media_type,
         specifier,
+        is_script,
         ..
       })) => {
+        if self.shared.cjs_tracker.is_cjs_with_known_is_script(
+          specifier,
+          *media_type,
+          *is_script,
+        )? {
+          return Ok(Some(CodeOrDeferredEmit::Cjs {
+            specifier,
+            media_type: *media_type,
+            source,
+          }));
+        }
         let code: ModuleCodeString = match media_type {
           MediaType::JavaScript
           | MediaType::Unknown
-          | MediaType::Cjs
           | MediaType::Mjs
           | MediaType::Json => source.clone().into(),
           MediaType::Dts | MediaType::Dcts | MediaType::Dmts => {
             Default::default()
           }
-          MediaType::TypeScript
-          | MediaType::Mts
-          | MediaType::Cts
-          | MediaType::Jsx
-          | MediaType::Tsx => {
-            return Ok(CodeOrDeferredEmit::DeferredEmit {
+          MediaType::Cjs | MediaType::Cts => {
+            return Ok(Some(CodeOrDeferredEmit::Cjs {
               specifier,
               media_type: *media_type,
               source,
-            });
+            }));
           }
-          MediaType::TsBuildInfo | MediaType::Wasm | MediaType::SourceMap => {
+          MediaType::TypeScript
+          | MediaType::Mts
+          | MediaType::Jsx
+          | MediaType::Tsx => {
+            return Ok(Some(CodeOrDeferredEmit::DeferredEmit {
+              specifier,
+              media_type: *media_type,
+              source,
+            }));
+          }
+          MediaType::Css | MediaType::Wasm | MediaType::SourceMap => {
             panic!("Unexpected media type {media_type} for {specifier}")
           }
         };
@@ -635,26 +725,62 @@ impl<TGraphContainer: ModuleGraphContainer>
         // at this point, we no longer need the parsed source in memory, so free it
         self.parsed_source_cache.free(specifier);
 
-        Ok(CodeOrDeferredEmit::Code(ModuleCodeStringSource {
+        Ok(Some(CodeOrDeferredEmit::Code(ModuleCodeStringSource {
           code: ModuleSourceCode::String(code),
           found_url: specifier.clone(),
           media_type: *media_type,
-        }))
+        })))
       }
       Some(
         deno_graph::Module::External(_)
         | deno_graph::Module::Node(_)
         | deno_graph::Module::Npm(_),
       )
-      | None => {
-        let mut msg = format!("Loading unprepared module: {specifier}");
-        if let Some(referrer) = maybe_referrer {
-          msg = format!("{}, imported from: {}", msg, referrer.as_str());
-        }
-        Err(anyhow!(msg))
-      }
+      | None => Ok(None),
     }
   }
+
+  async fn load_maybe_cjs(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+    original_source: &Arc<str>,
+  ) -> Result<ModuleCodeStringSource, AnyError> {
+    let js_source = if media_type.is_emittable() {
+      Cow::Owned(
+        self
+          .emitter
+          .emit_parsed_source(
+            specifier,
+            media_type,
+            ModuleKind::Cjs,
+            original_source,
+          )
+          .await?,
+      )
+    } else {
+      Cow::Borrowed(original_source.as_ref())
+    };
+    let text = self
+      .node_code_translator
+      .translate_cjs_to_esm(specifier, Some(js_source))
+      .await?;
+    // at this point, we no longer need the parsed source in memory, so free it
+    self.parsed_source_cache.free(specifier);
+    Ok(ModuleCodeStringSource {
+      code: match text {
+        // perf: if the text is borrowed, that means it didn't make any changes
+        // to the original source, so we can just provide that instead of cloning
+        // the borrowed text
+        Cow::Borrowed(_) => {
+          ModuleSourceCode::String(original_source.clone().into())
+        }
+        Cow::Owned(text) => ModuleSourceCode::String(text.into()),
+      },
+      found_url: specifier.clone(),
+      media_type,
+    })
+  }
 }
 
 enum CodeOrDeferredEmit<'a> {
@@ -664,6 +790,11 @@ enum CodeOrDeferredEmit<'a> {
     media_type: MediaType,
     source: &'a Arc<str>,
   },
+  Cjs {
+    specifier: &'a ModuleSpecifier,
+    media_type: MediaType,
+    source: &'a Arc<str>,
+  },
 }
 
 // todo(dsherret): this double Rc boxing is not ideal
@@ -705,7 +836,7 @@ impl<TGraphContainer: ModuleGraphContainer> ModuleLoader
     name: &str,
   ) -> Option<deno_core::v8::Local<'s, deno_core::v8::Data>> {
     let name = deno_core::ModuleSpecifier::parse(name).ok()?;
-    if self.0.shared.node_resolver.in_npm_package(&name) {
+    if self.0.shared.in_npm_pkg_checker.in_npm_package(&name) {
       Some(create_host_defined_options(scope))
     } else {
       None
@@ -742,7 +873,7 @@ impl<TGraphContainer: ModuleGraphContainer> ModuleLoader
     _maybe_referrer: Option<String>,
     is_dynamic: bool,
   ) -> Pin<Box<dyn Future<Output = Result<(), AnyError>>>> {
-    if self.0.shared.node_resolver.in_npm_package(specifier) {
+    if self.0.shared.in_npm_pkg_checker.in_npm_package(specifier) {
       return Box::pin(deno_core::futures::future::ready(Ok(())));
     }
 
@@ -825,7 +956,10 @@ impl<TGraphContainer: ModuleGraphContainer> ModuleLoader
       "wasm" | "file" | "http" | "https" | "data" | "blob" => (),
       _ => return None,
     }
-    let source = self.0.load_prepared_module_sync(&specifier, None).ok()?;
+    let source = self
+      .0
+      .load_prepared_module_for_source_map_sync(&specifier)
+      .ok()??;
     source_map_from_code(source.code.as_bytes())
   }
 
@@ -904,3 +1038,68 @@ impl ModuleGraphUpdatePermit for WorkerModuleGraphUpdatePermit {
     drop(self.permit); // explicit drop for clarity
   }
 }
+
+#[derive(Debug)]
+struct CliNodeRequireLoader<TGraphContainer: ModuleGraphContainer> {
+  cjs_tracker: Arc<CjsTracker>,
+  emitter: Arc<Emitter>,
+  fs: Arc<dyn FileSystem>,
+  graph_container: TGraphContainer,
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+  npm_resolver: Arc<dyn CliNpmResolver>,
+}
+
+impl<TGraphContainer: ModuleGraphContainer> NodeRequireLoader
+  for CliNodeRequireLoader<TGraphContainer>
+{
+  fn ensure_read_permission<'a>(
+    &self,
+    permissions: &mut dyn deno_runtime::deno_node::NodePermissions,
+    path: &'a Path,
+  ) -> Result<std::borrow::Cow<'a, Path>, AnyError> {
+    if let Ok(url) = deno_path_util::url_from_file_path(path) {
+      // allow reading if it's in the module graph
+      if self.graph_container.graph().get(&url).is_some() {
+        return Ok(std::borrow::Cow::Borrowed(path));
+      }
+    }
+    self.npm_resolver.ensure_read_permission(permissions, path)
+  }
+
+  fn load_text_file_lossy(&self, path: &Path) -> Result<String, AnyError> {
+    // todo(dsherret): use the preloaded module from the graph if available?
+    let media_type = MediaType::from_path(path);
+    let text = self.fs.read_text_file_lossy_sync(path, None)?;
+    if media_type.is_emittable() {
+      let specifier = deno_path_util::url_from_file_path(path)?;
+      if self.in_npm_pkg_checker.in_npm_package(&specifier) {
+        return Err(
+          NotSupportedKindInNpmError {
+            media_type,
+            specifier,
+          }
+          .into(),
+        );
+      }
+      self.emitter.emit_parsed_source_sync(
+        &specifier,
+        media_type,
+        // this is probably not super accurate due to require esm, but probably ok.
+        // If we find this causes a lot of churn in the emit cache then we should
+        // investigate how we can make this better
+        ModuleKind::Cjs,
+        &text.into(),
+      )
+    } else {
+      Ok(text)
+    }
+  }
+
+  fn is_maybe_cjs(
+    &self,
+    specifier: &ModuleSpecifier,
+  ) -> Result<bool, ClosestPkgJsonError> {
+    let media_type = MediaType::from_specifier(specifier);
+    self.cjs_tracker.is_maybe_cjs(specifier, media_type)
+  }
+}
diff --git a/cli/napi/README.md b/cli/napi/README.md
deleted file mode 100644
index 7b359ac6ec..0000000000
--- a/cli/napi/README.md
+++ /dev/null
@@ -1,114 +0,0 @@
-# napi
-
-This directory contains source for Deno's Node-API implementation. It depends on
-`napi_sym` and `deno_napi`.
-
-Files are generally organized the same as in Node.js's implementation to ease in
-ensuring compatibility.
-
-## Adding a new function
-
-Add the symbol name to
-[`cli/napi_sym/symbol_exports.json`](../napi_sym/symbol_exports.json).
-
-```diff
-{
-  "symbols": [
-    ...
-    "napi_get_undefined",
--   "napi_get_null"
-+   "napi_get_null",
-+   "napi_get_boolean"
-  ]
-}
-```
-
-Determine where to place the implementation. `napi_get_boolean` is related to JS
-values so we will place it in `js_native_api.rs`. If something is not clear,
-just create a new file module.
-
-See [`napi_sym`](../napi_sym/) for writing the implementation:
-
-```rust
-#[napi_sym::napi_sym]
-pub fn napi_get_boolean(
-  env: *mut Env,
-  value: bool,
-  result: *mut napi_value,
-) -> Result {
-  // ...
-  Ok(())
-}
-```
-
-Update the generated symbol lists using the script:
-
-```
-deno run --allow-write tools/napi/generate_symbols_lists.js
-```
-
-Add a test in [`/tests/napi`](../../tests/napi/). You can also refer to Node.js
-test suite for Node-API.
-
-```js
-// tests/napi/boolean_test.js
-import { assertEquals, loadTestLibrary } from "./common.js";
-const lib = loadTestLibrary();
-Deno.test("napi get boolean", function () {
-  assertEquals(lib.test_get_boolean(true), true);
-  assertEquals(lib.test_get_boolean(false), false);
-});
-```
-
-```rust
-// tests/napi/src/boolean.rs
-
-use napi_sys::Status::napi_ok;
-use napi_sys::ValueType::napi_boolean;
-use napi_sys::*;
-
-extern "C" fn test_boolean(
-  env: napi_env,
-  info: napi_callback_info,
-) -> napi_value {
-  let (args, argc, _) = crate::get_callback_info!(env, info, 1);
-  assert_eq!(argc, 1);
-
-  let mut ty = -1;
-  assert!(unsafe { napi_typeof(env, args[0], &mut ty) } == napi_ok);
-  assert_eq!(ty, napi_boolean);
-
-  // Use napi_get_boolean here...
-
-  value
-}
-
-pub fn init(env: napi_env, exports: napi_value) {
-  let properties = &[crate::new_property!(env, "test_boolean\0", test_boolean)];
-
-  unsafe {
-    napi_define_properties(env, exports, properties.len(), properties.as_ptr())
-  };
-}
-```
-
-```diff
-// tests/napi/src/lib.rs
-
-+ mod boolean;
-
-...
-
-#[no_mangle]
-unsafe extern "C" fn napi_register_module_v1(
-  env: napi_env,
-  exports: napi_value,
-) -> napi_value {
-  ...
-+ boolean::init(env, exports);
-
-  exports
-}
-```
-
-Run the test using `cargo test -p tests/napi`.
diff --git a/cli/napi/mod.rs b/cli/napi/mod.rs
deleted file mode 100644
index 122d2ff060..0000000000
--- a/cli/napi/mod.rs
+++ /dev/null
@@ -1,20 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-#![allow(unused_mut)]
-#![allow(non_camel_case_types)]
-#![allow(clippy::undocumented_unsafe_blocks)]
-
-//! Symbols to be exported are now defined in this JSON file.
-//! The `#[napi_sym]` macro checks for missing entries and panics.
-//!
-//! `./tools/napi/generate_symbols_list.js` is used to generate the LINK `cli/exports.def` on Windows,
-//! which is also checked into git.
-//!
-//! To add a new napi function:
-//! 1. Place `#[napi_sym]` on top of your implementation.
-//! 2. Add the function's identifier to this JSON list.
-//! 3. Finally, run `tools/napi/generate_symbols_list.js` to update `cli/napi/generated_symbol_exports_list_*.def`.
-
-pub mod js_native_api;
-pub mod node_api;
-pub mod util;
diff --git a/cli/node.rs b/cli/node.rs
index a3cee8ddee..bc39cdbde9 100644
--- a/cli/node.rs
+++ b/cli/node.rs
@@ -1,10 +1,12 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
+use std::borrow::Cow;
 use std::sync::Arc;
 
 use deno_ast::MediaType;
 use deno_ast::ModuleSpecifier;
 use deno_core::error::AnyError;
+use deno_graph::ParsedSourceStore;
 use deno_runtime::deno_fs;
 use deno_runtime::deno_node::DenoFsNodeResolverEnv;
 use node_resolver::analyze::CjsAnalysis as ExtNodeCjsAnalysis;
@@ -16,8 +18,8 @@ use serde::Serialize;
 
 use crate::cache::CacheDBHash;
 use crate::cache::NodeAnalysisCache;
-use crate::resolver::CliNodeResolver;
-use crate::util::fs::canonicalize_path_maybe_not_exists;
+use crate::cache::ParsedSourceCache;
+use crate::resolver::CjsTracker;
 
 pub type CliNodeCodeTranslator =
   NodeCodeTranslator<CliCjsCodeAnalyzer, DenoFsNodeResolverEnv>;
@@ -30,15 +32,11 @@ pub type CliNodeCodeTranslator =
 /// because the node_modules folder might not exist at that time.
 pub fn resolve_specifier_into_node_modules(
   specifier: &ModuleSpecifier,
+  fs: &dyn deno_fs::FileSystem,
 ) -> ModuleSpecifier {
-  specifier
-    .to_file_path()
-    .ok()
-    // this path might not exist at the time the graph is being created
-    // because the node_modules folder might not yet exist
-    .and_then(|path| canonicalize_path_maybe_not_exists(&path).ok())
-    .and_then(|path| ModuleSpecifier::from_file_path(path).ok())
-    .unwrap_or_else(|| specifier.clone())
+  node_resolver::resolve_specifier_into_node_modules(specifier, &|path| {
+    fs.realpath_sync(path).map_err(|err| err.into_io_error())
+  })
 }
 
 #[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
@@ -54,20 +52,23 @@ pub enum CliCjsAnalysis {
 
 pub struct CliCjsCodeAnalyzer {
   cache: NodeAnalysisCache,
+  cjs_tracker: Arc<CjsTracker>,
   fs: deno_fs::FileSystemRc,
-  node_resolver: Arc<CliNodeResolver>,
+  parsed_source_cache: Option<Arc<ParsedSourceCache>>,
 }
 
 impl CliCjsCodeAnalyzer {
   pub fn new(
     cache: NodeAnalysisCache,
+    cjs_tracker: Arc<CjsTracker>,
     fs: deno_fs::FileSystemRc,
-    node_resolver: Arc<CliNodeResolver>,
+    parsed_source_cache: Option<Arc<ParsedSourceCache>>,
   ) -> Self {
     Self {
       cache,
+      cjs_tracker,
       fs,
-      node_resolver,
+      parsed_source_cache,
     }
   }
 
@@ -83,7 +84,7 @@ impl CliCjsCodeAnalyzer {
       return Ok(analysis);
     }
 
-    let mut media_type = MediaType::from_specifier(specifier);
+    let media_type = MediaType::from_specifier(specifier);
     if media_type == MediaType::Json {
       return Ok(CliCjsAnalysis::Cjs {
         exports: vec![],
@@ -91,54 +92,51 @@ impl CliCjsCodeAnalyzer {
       });
     }
 
-    if media_type == MediaType::JavaScript {
-      if let Some(package_json) =
-        self.node_resolver.get_closest_package_json(specifier)?
-      {
-        match package_json.typ.as_str() {
-          "commonjs" => {
-            media_type = MediaType::Cjs;
-          }
-          "module" => {
-            media_type = MediaType::Mjs;
-          }
-          _ => {}
-        }
-      }
-    }
+    let cjs_tracker = self.cjs_tracker.clone();
+    let is_maybe_cjs = cjs_tracker.is_maybe_cjs(specifier, media_type)?;
+    let analysis = if is_maybe_cjs {
+      let maybe_parsed_source = self
+        .parsed_source_cache
+        .as_ref()
+        .and_then(|c| c.remove_parsed_source(specifier));
 
-    let analysis = deno_core::unsync::spawn_blocking({
-      let specifier = specifier.clone();
-      let source: Arc<str> = source.into();
-      move || -> Result<_, deno_ast::ParseDiagnostic> {
-        let parsed_source = deno_ast::parse_program(deno_ast::ParseParams {
-          specifier,
-          text: source,
-          media_type,
-          capture_tokens: true,
-          scope_analysis: false,
-          maybe_syntax: None,
-        })?;
-        if parsed_source.is_script() {
-          let analysis = parsed_source.analyze_cjs();
-          Ok(CliCjsAnalysis::Cjs {
-            exports: analysis.exports,
-            reexports: analysis.reexports,
-          })
-        } else if media_type == MediaType::Cjs {
-          // FIXME: `deno_ast` should internally handle MediaType::Cjs implying that
-          // the result must never be Esm
-          Ok(CliCjsAnalysis::Cjs {
-            exports: vec![],
-            reexports: vec![],
-          })
-        } else {
-          Ok(CliCjsAnalysis::Esm)
+      deno_core::unsync::spawn_blocking({
+        let specifier = specifier.clone();
+        let source: Arc<str> = source.into();
+        move || -> Result<_, AnyError> {
+          let parsed_source =
+            maybe_parsed_source.map(Ok).unwrap_or_else(|| {
+              deno_ast::parse_program(deno_ast::ParseParams {
+                specifier,
+                text: source,
+                media_type,
+                capture_tokens: true,
+                scope_analysis: false,
+                maybe_syntax: None,
+              })
+            })?;
+          let is_script = parsed_source.compute_is_script();
+          let is_cjs = cjs_tracker.is_cjs_with_known_is_script(
+            parsed_source.specifier(),
+            media_type,
+            is_script,
+          )?;
+          if is_cjs {
+            let analysis = parsed_source.analyze_cjs();
+            Ok(CliCjsAnalysis::Cjs {
+              exports: analysis.exports,
+              reexports: analysis.reexports,
+            })
+          } else {
+            Ok(CliCjsAnalysis::Esm)
+          }
         }
-      }
-    })
-    .await
-    .unwrap()?;
+      })
+      .await
+      .unwrap()?
+    } else {
+      CliCjsAnalysis::Esm
+    };
 
     self
       .cache
@@ -150,11 +148,11 @@ impl CliCjsCodeAnalyzer {
 
 #[async_trait::async_trait(?Send)]
 impl CjsCodeAnalyzer for CliCjsCodeAnalyzer {
-  async fn analyze_cjs(
+  async fn analyze_cjs<'a>(
     &self,
     specifier: &ModuleSpecifier,
-    source: Option<String>,
-  ) -> Result<ExtNodeCjsAnalysis, AnyError> {
+    source: Option<Cow<'a, str>>,
+  ) -> Result<ExtNodeCjsAnalysis<'a>, AnyError> {
     let source = match source {
       Some(source) => source,
       None => {
@@ -162,7 +160,7 @@ impl CjsCodeAnalyzer for CliCjsCodeAnalyzer {
           if let Ok(source_from_file) =
             self.fs.read_text_file_lossy_async(path, None).await
           {
-            source_from_file
+            Cow::Owned(source_from_file)
           } else {
             return Ok(ExtNodeCjsAnalysis::Cjs(CjsAnalysisExports {
               exports: vec![],
diff --git a/cli/npm/byonm.rs b/cli/npm/byonm.rs
index 4c8bbd3948..eca399251b 100644
--- a/cli/npm/byonm.rs
+++ b/cli/npm/byonm.rs
@@ -2,393 +2,92 @@
 
 use std::borrow::Cow;
 use std::path::Path;
-use std::path::PathBuf;
 use std::sync::Arc;
 
-use deno_ast::ModuleSpecifier;
-use deno_core::anyhow::bail;
 use deno_core::error::AnyError;
 use deno_core::serde_json;
-use deno_package_json::PackageJsonDepValue;
-use deno_runtime::deno_fs::FileSystem;
-use deno_runtime::deno_node::DenoPkgJsonFsAdapter;
+use deno_resolver::npm::ByonmNpmResolver;
+use deno_resolver::npm::ByonmNpmResolverCreateOptions;
+use deno_resolver::npm::CliNpmReqResolver;
+use deno_runtime::deno_node::DenoFsNodeResolverEnv;
 use deno_runtime::deno_node::NodePermissions;
-use deno_runtime::deno_node::NodeRequireResolver;
-use deno_runtime::deno_node::PackageJson;
-use deno_runtime::fs_util::specifier_to_file_path;
 use deno_runtime::ops::process::NpmProcessStateProvider;
-use deno_semver::package::PackageReq;
-use deno_semver::Version;
-use node_resolver::errors::PackageFolderResolveError;
-use node_resolver::errors::PackageFolderResolveIoError;
-use node_resolver::errors::PackageJsonLoadError;
-use node_resolver::errors::PackageNotFoundError;
-use node_resolver::load_pkg_json;
-use node_resolver::NpmResolver;
+use node_resolver::NpmPackageFolderResolver;
 
 use crate::args::NpmProcessState;
 use crate::args::NpmProcessStateKind;
-use crate::util::fs::canonicalize_path_maybe_not_exists_with_fs;
+use crate::resolver::CliDenoResolverFs;
 
-use super::managed::normalize_pkg_name_for_node_modules_deno_folder;
 use super::CliNpmResolver;
 use super::InnerCliNpmResolverRef;
 
-pub struct CliNpmResolverByonmCreateOptions {
-  pub fs: Arc<dyn FileSystem>,
-  // todo(dsherret): investigate removing this
-  pub root_node_modules_dir: Option<PathBuf>,
-}
-
-pub fn create_byonm_npm_resolver(
-  options: CliNpmResolverByonmCreateOptions,
-) -> Arc<dyn CliNpmResolver> {
-  Arc::new(ByonmCliNpmResolver {
-    fs: options.fs,
-    root_node_modules_dir: options.root_node_modules_dir,
-  })
-}
+pub type CliByonmNpmResolverCreateOptions =
+  ByonmNpmResolverCreateOptions<CliDenoResolverFs, DenoFsNodeResolverEnv>;
+pub type CliByonmNpmResolver =
+  ByonmNpmResolver<CliDenoResolverFs, DenoFsNodeResolverEnv>;
 
+// todo(dsherret): the services hanging off `CliNpmResolver` doesn't seem ideal. We should probably decouple.
 #[derive(Debug)]
-pub struct ByonmCliNpmResolver {
-  fs: Arc<dyn FileSystem>,
-  root_node_modules_dir: Option<PathBuf>,
-}
+struct CliByonmWrapper(Arc<CliByonmNpmResolver>);
 
-impl ByonmCliNpmResolver {
-  fn load_pkg_json(
-    &self,
-    path: &Path,
-  ) -> Result<Option<Arc<PackageJson>>, PackageJsonLoadError> {
-    load_pkg_json(&DenoPkgJsonFsAdapter(self.fs.as_ref()), path)
-  }
-
-  /// Finds the ancestor package.json that contains the specified dependency.
-  pub fn find_ancestor_package_json_with_dep(
-    &self,
-    dep_name: &str,
-    referrer: &ModuleSpecifier,
-  ) -> Option<Arc<PackageJson>> {
-    let referrer_path = referrer.to_file_path().ok()?;
-    let mut current_folder = referrer_path.parent()?;
-    loop {
-      let pkg_json_path = current_folder.join("package.json");
-      if let Ok(Some(pkg_json)) = self.load_pkg_json(&pkg_json_path) {
-        if let Some(deps) = &pkg_json.dependencies {
-          if deps.contains_key(dep_name) {
-            return Some(pkg_json);
-          }
-        }
-        if let Some(deps) = &pkg_json.dev_dependencies {
-          if deps.contains_key(dep_name) {
-            return Some(pkg_json);
-          }
-        }
-      }
-
-      if let Some(parent) = current_folder.parent() {
-        current_folder = parent;
-      } else {
-        return None;
-      }
-    }
-  }
-
-  fn resolve_pkg_json_and_alias_for_req(
-    &self,
-    req: &PackageReq,
-    referrer: &ModuleSpecifier,
-  ) -> Result<Option<(Arc<PackageJson>, String)>, AnyError> {
-    fn resolve_alias_from_pkg_json(
-      req: &PackageReq,
-      pkg_json: &PackageJson,
-    ) -> Option<String> {
-      let deps = pkg_json.resolve_local_package_json_deps();
-      for (key, value) in deps {
-        if let Ok(value) = value {
-          match value {
-            PackageJsonDepValue::Req(dep_req) => {
-              if dep_req.name == req.name
-                && dep_req.version_req.intersects(&req.version_req)
-              {
-                return Some(key);
-              }
-            }
-            PackageJsonDepValue::Workspace(_workspace) => {
-              if key == req.name && req.version_req.tag() == Some("workspace") {
-                return Some(key);
-              }
-            }
-          }
-        }
-      }
-      None
-    }
-
-    // attempt to resolve the npm specifier from the referrer's package.json,
-    if let Ok(file_path) = specifier_to_file_path(referrer) {
-      let mut current_path = file_path.as_path();
-      while let Some(dir_path) = current_path.parent() {
-        let package_json_path = dir_path.join("package.json");
-        if let Some(pkg_json) = self.load_pkg_json(&package_json_path)? {
-          if let Some(alias) =
-            resolve_alias_from_pkg_json(req, pkg_json.as_ref())
-          {
-            return Ok(Some((pkg_json, alias)));
-          }
-        }
-        current_path = dir_path;
-      }
-    }
-
-    // otherwise, fall fallback to the project's package.json
-    if let Some(root_node_modules_dir) = &self.root_node_modules_dir {
-      let root_pkg_json_path =
-        root_node_modules_dir.parent().unwrap().join("package.json");
-      if let Some(pkg_json) = self.load_pkg_json(&root_pkg_json_path)? {
-        if let Some(alias) = resolve_alias_from_pkg_json(req, pkg_json.as_ref())
-        {
-          return Ok(Some((pkg_json, alias)));
-        }
-      }
-    }
-
-    Ok(None)
-  }
-
-  fn resolve_folder_in_root_node_modules(
-    &self,
-    req: &PackageReq,
-  ) -> Option<PathBuf> {
-    // now check if node_modules/.deno/ matches this constraint
-    let root_node_modules_dir = self.root_node_modules_dir.as_ref()?;
-    let node_modules_deno_dir = root_node_modules_dir.join(".deno");
-    let Ok(entries) = self.fs.read_dir_sync(&node_modules_deno_dir) else {
-      return None;
-    };
-    let search_prefix = format!(
-      "{}@",
-      normalize_pkg_name_for_node_modules_deno_folder(&req.name)
-    );
-    let mut best_version = None;
-
-    // example entries:
-    // - @denotest+add@1.0.0
-    // - @denotest+add@1.0.0_1
-    for entry in entries {
-      if !entry.is_directory {
-        continue;
-      }
-      let Some(version_and_copy_idx) = entry.name.strip_prefix(&search_prefix)
-      else {
-        continue;
-      };
-      let version = version_and_copy_idx
-        .rsplit_once('_')
-        .map(|(v, _)| v)
-        .unwrap_or(version_and_copy_idx);
-      let Ok(version) = Version::parse_from_npm(version) else {
-        continue;
-      };
-      if req.version_req.matches(&version) {
-        if let Some((best_version_version, _)) = &best_version {
-          if version > *best_version_version {
-            best_version = Some((version, entry.name));
-          }
-        } else {
-          best_version = Some((version, entry.name));
-        }
-      }
-    }
-
-    best_version.map(|(_version, entry_name)| {
-      join_package_name(
-        &node_modules_deno_dir.join(entry_name).join("node_modules"),
-        &req.name,
-      )
-    })
-  }
-}
-
-impl NpmResolver for ByonmCliNpmResolver {
-  fn resolve_package_folder_from_package(
-    &self,
-    name: &str,
-    referrer: &ModuleSpecifier,
-  ) -> Result<PathBuf, PackageFolderResolveError> {
-    fn inner(
-      fs: &dyn FileSystem,
-      name: &str,
-      referrer: &ModuleSpecifier,
-    ) -> Result<PathBuf, PackageFolderResolveError> {
-      let maybe_referrer_file = specifier_to_file_path(referrer).ok();
-      let maybe_start_folder =
-        maybe_referrer_file.as_ref().and_then(|f| f.parent());
-      if let Some(start_folder) = maybe_start_folder {
-        for current_folder in start_folder.ancestors() {
-          let node_modules_folder = if current_folder.ends_with("node_modules")
-          {
-            Cow::Borrowed(current_folder)
-          } else {
-            Cow::Owned(current_folder.join("node_modules"))
-          };
-
-          let sub_dir = join_package_name(&node_modules_folder, name);
-          if fs.is_dir_sync(&sub_dir) {
-            return Ok(sub_dir);
-          }
-        }
-      }
-
-      Err(
-        PackageNotFoundError {
-          package_name: name.to_string(),
-          referrer: referrer.clone(),
-          referrer_extra: None,
-        }
-        .into(),
-      )
-    }
-
-    let path = inner(&*self.fs, name, referrer)?;
-    self.fs.realpath_sync(&path).map_err(|err| {
-      PackageFolderResolveIoError {
-        package_name: name.to_string(),
-        referrer: referrer.clone(),
-        source: err.into_io_error(),
-      }
-      .into()
-    })
-  }
-
-  fn in_npm_package(&self, specifier: &ModuleSpecifier) -> bool {
-    specifier.scheme() == "file"
-      && specifier
-        .path()
-        .to_ascii_lowercase()
-        .contains("/node_modules/")
-  }
-}
-
-impl NodeRequireResolver for ByonmCliNpmResolver {
-  fn ensure_read_permission(
-    &self,
-    permissions: &mut dyn NodePermissions,
-    path: &Path,
-  ) -> Result<(), AnyError> {
-    if !path
-      .components()
-      .any(|c| c.as_os_str().to_ascii_lowercase() == "node_modules")
-    {
-      _ = permissions.check_read_path(path)?;
-    }
-    Ok(())
-  }
-}
-
-impl NpmProcessStateProvider for ByonmCliNpmResolver {
+impl NpmProcessStateProvider for CliByonmWrapper {
   fn get_npm_process_state(&self) -> String {
     serde_json::to_string(&NpmProcessState {
       kind: NpmProcessStateKind::Byonm,
       local_node_modules_path: self
-        .root_node_modules_dir
-        .as_ref()
+        .0
+        .root_node_modules_dir()
         .map(|p| p.to_string_lossy().to_string()),
     })
     .unwrap()
   }
 }
 
-impl CliNpmResolver for ByonmCliNpmResolver {
-  fn into_npm_resolver(self: Arc<Self>) -> Arc<dyn NpmResolver> {
+impl CliNpmResolver for CliByonmNpmResolver {
+  fn into_npm_pkg_folder_resolver(
+    self: Arc<Self>,
+  ) -> Arc<dyn NpmPackageFolderResolver> {
     self
   }
 
-  fn into_require_resolver(self: Arc<Self>) -> Arc<dyn NodeRequireResolver> {
+  fn into_npm_req_resolver(self: Arc<Self>) -> Arc<dyn CliNpmReqResolver> {
     self
   }
 
   fn into_process_state_provider(
     self: Arc<Self>,
   ) -> Arc<dyn NpmProcessStateProvider> {
-    self
+    Arc::new(CliByonmWrapper(self))
+  }
+
+  fn into_maybe_byonm(self: Arc<Self>) -> Option<Arc<CliByonmNpmResolver>> {
+    Some(self)
   }
 
   fn clone_snapshotted(&self) -> Arc<dyn CliNpmResolver> {
-    Arc::new(Self {
-      fs: self.fs.clone(),
-      root_node_modules_dir: self.root_node_modules_dir.clone(),
-    })
+    Arc::new(self.clone())
   }
 
   fn as_inner(&self) -> InnerCliNpmResolverRef {
     InnerCliNpmResolverRef::Byonm(self)
   }
 
-  fn root_node_modules_path(&self) -> Option<&PathBuf> {
-    self.root_node_modules_dir.as_ref()
+  fn root_node_modules_path(&self) -> Option<&Path> {
+    self.root_node_modules_dir()
   }
 
-  fn resolve_pkg_folder_from_deno_module_req(
+  fn ensure_read_permission<'a>(
     &self,
-    req: &PackageReq,
-    referrer: &ModuleSpecifier,
-  ) -> Result<PathBuf, AnyError> {
-    fn node_resolve_dir(
-      fs: &dyn FileSystem,
-      alias: &str,
-      start_dir: &Path,
-    ) -> Result<Option<PathBuf>, AnyError> {
-      for ancestor in start_dir.ancestors() {
-        let node_modules_folder = ancestor.join("node_modules");
-        let sub_dir = join_package_name(&node_modules_folder, alias);
-        if fs.is_dir_sync(&sub_dir) {
-          return Ok(Some(canonicalize_path_maybe_not_exists_with_fs(
-            &sub_dir, fs,
-          )?));
-        }
-      }
-      Ok(None)
-    }
-
-    // now attempt to resolve if it's found in any package.json
-    let maybe_pkg_json_and_alias =
-      self.resolve_pkg_json_and_alias_for_req(req, referrer)?;
-    match maybe_pkg_json_and_alias {
-      Some((pkg_json, alias)) => {
-        // now try node resolution
-        if let Some(resolved) =
-          node_resolve_dir(self.fs.as_ref(), &alias, pkg_json.dir_path())?
-        {
-          return Ok(resolved);
-        }
-
-        bail!(
-          concat!(
-            "Could not find \"{}\" in a node_modules folder. ",
-            "Deno expects the node_modules/ directory to be up to date. ",
-            "Did you forget to run `deno install`?"
-          ),
-          alias,
-        );
-      }
-      None => {
-        // now check if node_modules/.deno/ matches this constraint
-        if let Some(folder) = self.resolve_folder_in_root_node_modules(req) {
-          return Ok(folder);
-        }
-
-        bail!(
-          concat!(
-            "Could not find a matching package for 'npm:{}' in the node_modules ",
-            "directory. Ensure you have all your JSR and npm dependencies listed ",
-            "in your deno.json or package.json, then run `deno install`. Alternatively, ",
-            r#"turn on auto-install by specifying `"nodeModulesDir": "auto"` in your "#,
-            "deno.json file."
-          ),
-          req,
-        );
-      }
+    permissions: &mut dyn NodePermissions,
+    path: &'a Path,
+  ) -> Result<Cow<'a, Path>, AnyError> {
+    if !path
+      .components()
+      .any(|c| c.as_os_str().to_ascii_lowercase() == "node_modules")
+    {
+      permissions.check_read_path(path).map_err(Into::into)
+    } else {
+      Ok(Cow::Borrowed(path))
     }
   }
 
@@ -398,12 +97,3 @@ impl CliNpmResolver for ByonmCliNpmResolver {
     None
   }
 }
-
-fn join_package_name(path: &Path, package_name: &str) -> PathBuf {
-  let mut path = path.to_path_buf();
-  // ensure backslashes are used on windows
-  for part in package_name.split('/') {
-    path = path.join(part);
-  }
-  path
-}
diff --git a/cli/npm/cache_dir.rs b/cli/npm/cache_dir.rs
deleted file mode 100644
index 4467d685ec..0000000000
--- a/cli/npm/cache_dir.rs
+++ /dev/null
@@ -1,295 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-use std::path::Path;
-use std::path::PathBuf;
-
-use deno_ast::ModuleSpecifier;
-use deno_core::anyhow::Context;
-use deno_core::error::AnyError;
-use deno_core::url::Url;
-use deno_npm::NpmPackageCacheFolderId;
-use deno_semver::package::PackageNv;
-use deno_semver::Version;
-
-use crate::util::fs::canonicalize_path;
-use crate::util::path::root_url_to_safe_local_dirname;
-
-/// The global cache directory of npm packages.
-#[derive(Clone, Debug)]
-pub struct NpmCacheDir {
-  root_dir: PathBuf,
-  // cached url representation of the root directory
-  root_dir_url: Url,
-  // A list of all registry that were discovered via `.npmrc` files
-  // turned into a safe directory names.
-  known_registries_dirnames: Vec<String>,
-}
-
-impl NpmCacheDir {
-  pub fn new(root_dir: PathBuf, known_registries_urls: Vec<Url>) -> Self {
-    fn try_get_canonicalized_root_dir(
-      root_dir: &Path,
-    ) -> Result<PathBuf, AnyError> {
-      if !root_dir.exists() {
-        std::fs::create_dir_all(root_dir)
-          .with_context(|| format!("Error creating {}", root_dir.display()))?;
-      }
-      Ok(canonicalize_path(root_dir)?)
-    }
-
-    // this may fail on readonly file systems, so just ignore if so
-    let root_dir =
-      try_get_canonicalized_root_dir(&root_dir).unwrap_or(root_dir);
-    let root_dir_url = Url::from_directory_path(&root_dir).unwrap();
-
-    let known_registries_dirnames: Vec<_> = known_registries_urls
-      .into_iter()
-      .map(|url| {
-        root_url_to_safe_local_dirname(&url)
-          .to_string_lossy()
-          .replace('\\', "/")
-      })
-      .collect();
-
-    Self {
-      root_dir,
-      root_dir_url,
-      known_registries_dirnames,
-    }
-  }
-
-  pub fn root_dir(&self) -> &Path {
-    &self.root_dir
-  }
-
-  pub fn root_dir_url(&self) -> &Url {
-    &self.root_dir_url
-  }
-
-  pub fn package_folder_for_id(
-    &self,
-    folder_id: &NpmPackageCacheFolderId,
-    registry_url: &Url,
-  ) -> PathBuf {
-    if folder_id.copy_index == 0 {
-      self.package_folder_for_nv(&folder_id.nv, registry_url)
-    } else {
-      self
-        .package_name_folder(&folder_id.nv.name, registry_url)
-        .join(format!("{}_{}", folder_id.nv.version, folder_id.copy_index))
-    }
-  }
-
-  pub fn package_folder_for_nv(
-    &self,
-    package: &PackageNv,
-    registry_url: &Url,
-  ) -> PathBuf {
-    self
-      .package_name_folder(&package.name, registry_url)
-      .join(package.version.to_string())
-  }
-
-  pub fn package_name_folder(&self, name: &str, registry_url: &Url) -> PathBuf {
-    let mut dir = self.registry_folder(registry_url);
-    if name.to_lowercase() != name {
-      let encoded_name = mixed_case_package_name_encode(name);
-      // Using the encoded directory may have a collision with an actual package name
-      // so prefix it with an underscore since npm packages can't start with that
-      dir.join(format!("_{encoded_name}"))
-    } else {
-      // ensure backslashes are used on windows
-      for part in name.split('/') {
-        dir = dir.join(part);
-      }
-      dir
-    }
-  }
-
-  fn registry_folder(&self, registry_url: &Url) -> PathBuf {
-    self
-      .root_dir
-      .join(root_url_to_safe_local_dirname(registry_url))
-  }
-
-  pub fn resolve_package_folder_id_from_specifier(
-    &self,
-    specifier: &ModuleSpecifier,
-  ) -> Option<NpmPackageCacheFolderId> {
-    let mut maybe_relative_url = None;
-
-    // Iterate through known registries and try to get a match.
-    for registry_dirname in &self.known_registries_dirnames {
-      let registry_root_dir = self
-        .root_dir_url
-        .join(&format!("{}/", registry_dirname))
-        // this not succeeding indicates a fatal issue, so unwrap
-        .unwrap();
-
-      let Some(relative_url) = registry_root_dir.make_relative(specifier)
-      else {
-        continue;
-      };
-
-      if relative_url.starts_with("../") {
-        continue;
-      }
-
-      maybe_relative_url = Some(relative_url);
-      break;
-    }
-
-    let mut relative_url = maybe_relative_url?;
-
-    // base32 decode the url if it starts with an underscore
-    // * Ex. _{base32(package_name)}/
-    if let Some(end_url) = relative_url.strip_prefix('_') {
-      let mut parts = end_url
-        .split('/')
-        .map(ToOwned::to_owned)
-        .collect::<Vec<_>>();
-      match mixed_case_package_name_decode(&parts[0]) {
-        Some(part) => {
-          parts[0] = part;
-        }
-        None => return None,
-      }
-      relative_url = parts.join("/");
-    }
-
-    // examples:
-    // * chalk/5.0.1/
-    // * @types/chalk/5.0.1/
-    // * some-package/5.0.1_1/ -- where the `_1` (/_\d+/) is a copy of the folder for peer deps
-    let is_scoped_package = relative_url.starts_with('@');
-    let mut parts = relative_url
-      .split('/')
-      .enumerate()
-      .take(if is_scoped_package { 3 } else { 2 })
-      .map(|(_, part)| part)
-      .collect::<Vec<_>>();
-    if parts.len() < 2 {
-      return None;
-    }
-    let version_part = parts.pop().unwrap();
-    let name = parts.join("/");
-    let (version, copy_index) =
-      if let Some((version, copy_count)) = version_part.split_once('_') {
-        (version, copy_count.parse::<u8>().ok()?)
-      } else {
-        (version_part, 0)
-      };
-    Some(NpmPackageCacheFolderId {
-      nv: PackageNv {
-        name,
-        version: Version::parse_from_npm(version).ok()?,
-      },
-      copy_index,
-    })
-  }
-
-  pub fn get_cache_location(&self) -> PathBuf {
-    self.root_dir.clone()
-  }
-}
-
-pub fn mixed_case_package_name_encode(name: &str) -> String {
-  // use base32 encoding because it's reversible and the character set
-  // only includes the characters within 0-9 and A-Z so it can be lower cased
-  base32::encode(
-    base32::Alphabet::Rfc4648Lower { padding: false },
-    name.as_bytes(),
-  )
-  .to_lowercase()
-}
-
-pub fn mixed_case_package_name_decode(name: &str) -> Option<String> {
-  base32::decode(base32::Alphabet::Rfc4648Lower { padding: false }, name)
-    .and_then(|b| String::from_utf8(b).ok())
-}
-
-#[cfg(test)]
-mod test {
-  use deno_core::url::Url;
-  use deno_semver::package::PackageNv;
-  use deno_semver::Version;
-
-  use super::NpmCacheDir;
-  use crate::npm::cache_dir::NpmPackageCacheFolderId;
-
-  #[test]
-  fn should_get_package_folder() {
-    let deno_dir = crate::cache::DenoDir::new(None).unwrap();
-    let root_dir = deno_dir.npm_folder_path();
-    let registry_url = Url::parse("https://registry.npmjs.org/").unwrap();
-    let cache = NpmCacheDir::new(root_dir.clone(), vec![registry_url.clone()]);
-
-    assert_eq!(
-      cache.package_folder_for_id(
-        &NpmPackageCacheFolderId {
-          nv: PackageNv {
-            name: "json".to_string(),
-            version: Version::parse_from_npm("1.2.5").unwrap(),
-          },
-          copy_index: 0,
-        },
-        &registry_url,
-      ),
-      root_dir
-        .join("registry.npmjs.org")
-        .join("json")
-        .join("1.2.5"),
-    );
-
-    assert_eq!(
-      cache.package_folder_for_id(
-        &NpmPackageCacheFolderId {
-          nv: PackageNv {
-            name: "json".to_string(),
-            version: Version::parse_from_npm("1.2.5").unwrap(),
-          },
-          copy_index: 1,
-        },
-        &registry_url,
-      ),
-      root_dir
-        .join("registry.npmjs.org")
-        .join("json")
-        .join("1.2.5_1"),
-    );
-
-    assert_eq!(
-      cache.package_folder_for_id(
-        &NpmPackageCacheFolderId {
-          nv: PackageNv {
-            name: "JSON".to_string(),
-            version: Version::parse_from_npm("2.1.5").unwrap(),
-          },
-          copy_index: 0,
-        },
-        &registry_url,
-      ),
-      root_dir
-        .join("registry.npmjs.org")
-        .join("_jjju6tq")
-        .join("2.1.5"),
-    );
-
-    assert_eq!(
-      cache.package_folder_for_id(
-        &NpmPackageCacheFolderId {
-          nv: PackageNv {
-            name: "@types/JSON".to_string(),
-            version: Version::parse_from_npm("2.1.5").unwrap(),
-          },
-          copy_index: 0,
-        },
-        &registry_url,
-      ),
-      root_dir
-        .join("registry.npmjs.org")
-        .join("_ib2hs4dfomxuuu2pjy")
-        .join("2.1.5"),
-    );
-  }
-}
diff --git a/cli/npm/common.rs b/cli/npm/common.rs
index a3a828e745..55f1bc086d 100644
--- a/cli/npm/common.rs
+++ b/cli/npm/common.rs
@@ -3,6 +3,7 @@
 use base64::prelude::BASE64_STANDARD;
 use base64::Engine;
 use deno_core::anyhow::bail;
+use deno_core::anyhow::Context;
 use deno_core::error::AnyError;
 use deno_npm::npm_rc::RegistryConfig;
 use http::header;
@@ -36,17 +37,21 @@ pub fn maybe_auth_header_for_npm_registry(
   }
 
   if username.is_some() && password.is_some() {
+    // The npm client does some double encoding when generating the
+    // bearer token value, see
+    // https://github.com/npm/cli/blob/780afc50e3a345feb1871a28e33fa48235bc3bd5/workspaces/config/lib/index.js#L846-L851
+    let pw_base64 = BASE64_STANDARD
+      .decode(password.unwrap())
+      .with_context(|| "The password in npmrc is an invalid base64 string")?;
+    let bearer = BASE64_STANDARD.encode(format!(
+      "{}:{}",
+      username.unwrap(),
+      String::from_utf8_lossy(&pw_base64)
+    ));
+
     return Ok(Some((
       header::AUTHORIZATION,
-      header::HeaderValue::from_str(&format!(
-        "Basic {}",
-        BASE64_STANDARD.encode(&format!(
-          "{}:{}",
-          username.unwrap(),
-          password.unwrap()
-        ))
-      ))
-      .unwrap(),
+      header::HeaderValue::from_str(&format!("Basic {}", bearer)).unwrap(),
     )));
   }
 
diff --git a/cli/npm/managed/cache/mod.rs b/cli/npm/managed/cache/mod.rs
index f409744b98..8ae99f41e0 100644
--- a/cli/npm/managed/cache/mod.rs
+++ b/cli/npm/managed/cache/mod.rs
@@ -8,6 +8,7 @@ use std::path::PathBuf;
 use std::sync::Arc;
 
 use deno_ast::ModuleSpecifier;
+use deno_cache_dir::npm::NpmCacheDir;
 use deno_core::anyhow::bail;
 use deno_core::anyhow::Context;
 use deno_core::error::AnyError;
@@ -18,14 +19,14 @@ use deno_npm::npm_rc::ResolvedNpmRc;
 use deno_npm::registry::NpmPackageInfo;
 use deno_npm::NpmPackageCacheFolderId;
 use deno_semver::package::PackageNv;
+use deno_semver::Version;
 
 use crate::args::CacheSetting;
 use crate::cache::CACHE_PERM;
-use crate::npm::NpmCacheDir;
 use crate::util::fs::atomic_write_file_with_retries;
 use crate::util::fs::hard_link_dir_recursive;
 
-mod registry_info;
+pub mod registry_info;
 mod tarball;
 mod tarball_extract;
 
@@ -35,7 +36,7 @@ pub use tarball::TarballCache;
 /// Stores a single copy of npm packages in a cache.
 #[derive(Debug)]
 pub struct NpmCache {
-  cache_dir: NpmCacheDir,
+  cache_dir: Arc<NpmCacheDir>,
   cache_setting: CacheSetting,
   npmrc: Arc<ResolvedNpmRc>,
   /// ensures a package is only downloaded once per run
@@ -44,7 +45,7 @@ pub struct NpmCache {
 
 impl NpmCache {
   pub fn new(
-    cache_dir: NpmCacheDir,
+    cache_dir: Arc<NpmCacheDir>,
     cache_setting: CacheSetting,
     npmrc: Arc<ResolvedNpmRc>,
   ) -> Self {
@@ -60,6 +61,10 @@ impl NpmCache {
     &self.cache_setting
   }
 
+  pub fn root_dir_path(&self) -> &Path {
+    self.cache_dir.root_dir()
+  }
+
   pub fn root_dir_url(&self) -> &Url {
     self.cache_dir.root_dir_url()
   }
@@ -87,9 +92,12 @@ impl NpmCache {
   ) -> Result<(), AnyError> {
     let registry_url = self.npmrc.get_registry_url(&folder_id.nv.name);
     assert_ne!(folder_id.copy_index, 0);
-    let package_folder = self
-      .cache_dir
-      .package_folder_for_id(folder_id, registry_url);
+    let package_folder = self.cache_dir.package_folder_for_id(
+      &folder_id.nv.name,
+      &folder_id.nv.version.to_string(),
+      folder_id.copy_index,
+      registry_url,
+    );
 
     if package_folder.exists()
       // if this file exists, then the package didn't successfully initialize
@@ -100,9 +108,12 @@ impl NpmCache {
       return Ok(());
     }
 
-    let original_package_folder = self
-      .cache_dir
-      .package_folder_for_nv(&folder_id.nv, registry_url);
+    let original_package_folder = self.cache_dir.package_folder_for_id(
+      &folder_id.nv.name,
+      &folder_id.nv.version.to_string(),
+      0, // original copy index
+      registry_url,
+    );
 
     // it seems Windows does an "AccessDenied" error when moving a
     // directory with hard links, so that's why this solution is done
@@ -114,7 +125,12 @@ impl NpmCache {
 
   pub fn package_folder_for_id(&self, id: &NpmPackageCacheFolderId) -> PathBuf {
     let registry_url = self.npmrc.get_registry_url(&id.nv.name);
-    self.cache_dir.package_folder_for_id(id, registry_url)
+    self.cache_dir.package_folder_for_id(
+      &id.nv.name,
+      &id.nv.version.to_string(),
+      id.copy_index,
+      registry_url,
+    )
   }
 
   pub fn package_folder_for_nv(&self, package: &PackageNv) -> PathBuf {
@@ -127,7 +143,12 @@ impl NpmCache {
     package: &PackageNv,
     registry_url: &Url,
   ) -> PathBuf {
-    self.cache_dir.package_folder_for_nv(package, registry_url)
+    self.cache_dir.package_folder_for_id(
+      &package.name,
+      &package.version.to_string(),
+      0, // original copy_index
+      registry_url,
+    )
   }
 
   pub fn package_name_folder(&self, name: &str) -> PathBuf {
@@ -135,10 +156,6 @@ impl NpmCache {
     self.cache_dir.package_name_folder(name, registry_url)
   }
 
-  pub fn root_folder(&self) -> PathBuf {
-    self.cache_dir.root_dir().to_owned()
-  }
-
   pub fn resolve_package_folder_id_from_specifier(
     &self,
     specifier: &ModuleSpecifier,
@@ -146,6 +163,15 @@ impl NpmCache {
     self
       .cache_dir
       .resolve_package_folder_id_from_specifier(specifier)
+      .and_then(|cache_id| {
+        Some(NpmPackageCacheFolderId {
+          nv: PackageNv {
+            name: cache_id.name,
+            version: Version::parse_from_npm(&cache_id.version).ok()?,
+          },
+          copy_index: cache_id.copy_index,
+        })
+      })
   }
 
   pub fn load_package_info(
diff --git a/cli/npm/managed/cache/registry_info.rs b/cli/npm/managed/cache/registry_info.rs
index 28b19373e9..6d39d3c13f 100644
--- a/cli/npm/managed/cache/registry_info.rs
+++ b/cli/npm/managed/cache/registry_info.rs
@@ -84,7 +84,7 @@ impl RegistryInfoDownloader {
     self.load_package_info_inner(name).await.with_context(|| {
       format!(
         "Error getting response at {} for package \"{}\"",
-        self.get_package_url(name),
+        get_package_url(&self.npmrc, name),
         name
       )
     })
@@ -190,7 +190,7 @@ impl RegistryInfoDownloader {
 
   fn create_load_future(self: &Arc<Self>, name: &str) -> LoadFuture {
     let downloader = self.clone();
-    let package_url = self.get_package_url(name);
+    let package_url = get_package_url(&self.npmrc, name);
     let registry_config = self.npmrc.get_registry_config(name);
     let maybe_auth_header =
       match maybe_auth_header_for_npm_registry(registry_config) {
@@ -202,10 +202,13 @@ impl RegistryInfoDownloader {
     let guard = self.progress_bar.update(package_url.as_str());
     let name = name.to_string();
     async move {
-      let maybe_bytes = downloader
-        .http_client_provider
-        .get_or_create()?
-        .download_with_progress(package_url, maybe_auth_header, &guard)
+      let client = downloader.http_client_provider.get_or_create()?;
+      let maybe_bytes = client
+        .download_with_progress_and_retries(
+          package_url,
+          maybe_auth_header,
+          &guard,
+        )
         .await?;
       match maybe_bytes {
         Some(bytes) => {
@@ -236,25 +239,36 @@ impl RegistryInfoDownloader {
     .map(|r| r.map_err(Arc::new))
     .boxed_local()
   }
-
-  fn get_package_url(&self, name: &str) -> Url {
-    let registry_url = self.npmrc.get_registry_url(name);
-    // list of all characters used in npm packages:
-    //  !, ', (, ), *, -, ., /, [0-9], @, [A-Za-z], _, ~
-    const ASCII_SET: percent_encoding::AsciiSet =
-      percent_encoding::NON_ALPHANUMERIC
-        .remove(b'!')
-        .remove(b'\'')
-        .remove(b'(')
-        .remove(b')')
-        .remove(b'*')
-        .remove(b'-')
-        .remove(b'.')
-        .remove(b'/')
-        .remove(b'@')
-        .remove(b'_')
-        .remove(b'~');
-    let name = percent_encoding::utf8_percent_encode(name, &ASCII_SET);
-    registry_url.join(&name.to_string()).unwrap()
-  }
+}
+
+pub fn get_package_url(npmrc: &ResolvedNpmRc, name: &str) -> Url {
+  let registry_url = npmrc.get_registry_url(name);
+  // The '/' character in scoped package names "@scope/name" must be
+  // encoded for older third party registries. Newer registries and
+  // npm itself support both ways
+  //   - encoded: https://registry.npmjs.org/@rollup%2fplugin-json
+  //   - non-ecoded: https://registry.npmjs.org/@rollup/plugin-json
+  // To support as many third party registries as possible we'll
+  // always encode the '/' character.
+
+  // list of all characters used in npm packages:
+  //  !, ', (, ), *, -, ., /, [0-9], @, [A-Za-z], _, ~
+  const ASCII_SET: percent_encoding::AsciiSet =
+    percent_encoding::NON_ALPHANUMERIC
+      .remove(b'!')
+      .remove(b'\'')
+      .remove(b'(')
+      .remove(b')')
+      .remove(b'*')
+      .remove(b'-')
+      .remove(b'.')
+      .remove(b'@')
+      .remove(b'_')
+      .remove(b'~');
+  let name = percent_encoding::utf8_percent_encode(name, &ASCII_SET);
+  registry_url
+    // Ensure that scoped package name percent encoding is lower cased
+    // to match npm.
+    .join(&name.to_string().replace("%2F", "%2f"))
+    .unwrap()
 }
diff --git a/cli/npm/managed/cache/tarball.rs b/cli/npm/managed/cache/tarball.rs
index 4bcee38ea8..7cf88d6d64 100644
--- a/cli/npm/managed/cache/tarball.rs
+++ b/cli/npm/managed/cache/tarball.rs
@@ -172,7 +172,7 @@ impl TarballCache {
       let guard = tarball_cache.progress_bar.update(&dist.tarball);
       let result = tarball_cache.http_client_provider
         .get_or_create()?
-        .download_with_progress(tarball_uri, maybe_auth_header, &guard)
+        .download_with_progress_and_retries(tarball_uri, maybe_auth_header, &guard)
         .await;
       let maybe_bytes = match result {
         Ok(maybe_bytes) => maybe_bytes,
diff --git a/cli/npm/managed/mod.rs b/cli/npm/managed/mod.rs
index 40c92cd46c..2e64f5f188 100644
--- a/cli/npm/managed/mod.rs
+++ b/cli/npm/managed/mod.rs
@@ -1,5 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
+use std::borrow::Cow;
 use std::path::Path;
 use std::path::PathBuf;
 use std::sync::Arc;
@@ -7,9 +8,11 @@ use std::sync::Arc;
 use cache::RegistryInfoDownloader;
 use cache::TarballCache;
 use deno_ast::ModuleSpecifier;
+use deno_cache_dir::npm::NpmCacheDir;
 use deno_core::anyhow::Context;
 use deno_core::error::AnyError;
 use deno_core::serde_json;
+use deno_core::url::Url;
 use deno_npm::npm_rc::ResolvedNpmRc;
 use deno_npm::registry::NpmPackageInfo;
 use deno_npm::registry::NpmRegistryApi;
@@ -19,15 +22,17 @@ use deno_npm::resolution::ValidSerializedNpmResolutionSnapshot;
 use deno_npm::NpmPackageId;
 use deno_npm::NpmResolutionPackage;
 use deno_npm::NpmSystemInfo;
+use deno_resolver::npm::CliNpmReqResolver;
+use deno_runtime::colors;
 use deno_runtime::deno_fs::FileSystem;
 use deno_runtime::deno_node::NodePermissions;
-use deno_runtime::deno_node::NodeRequireResolver;
 use deno_runtime::ops::process::NpmProcessStateProvider;
 use deno_semver::package::PackageNv;
 use deno_semver::package::PackageReq;
 use node_resolver::errors::PackageFolderResolveError;
 use node_resolver::errors::PackageFolderResolveIoError;
-use node_resolver::NpmResolver;
+use node_resolver::InNpmPackageChecker;
+use node_resolver::NpmPackageFolderResolver;
 use resolution::AddPkgReqsResult;
 
 use crate::args::CliLockfile;
@@ -35,6 +40,7 @@ use crate::args::LifecycleScriptsConfig;
 use crate::args::NpmInstallDepsProvider;
 use crate::args::NpmProcessState;
 use crate::args::NpmProcessStateKind;
+use crate::args::PackageJsonDepValueParseWithLocationError;
 use crate::cache::FastInsecureHasher;
 use crate::http_util::HttpClientProvider;
 use crate::util::fs::canonicalize_path_maybe_not_exists_with_fs;
@@ -45,14 +51,13 @@ use self::cache::NpmCache;
 use self::registry::CliNpmRegistryApi;
 use self::resolution::NpmResolution;
 use self::resolvers::create_npm_fs_resolver;
-pub use self::resolvers::normalize_pkg_name_for_node_modules_deno_folder;
 use self::resolvers::NpmPackageFsResolver;
 
 use super::CliNpmResolver;
 use super::InnerCliNpmResolverRef;
-use super::NpmCacheDir;
+use super::ResolvePkgFolderFromDenoReqError;
 
-mod cache;
+pub mod cache;
 mod registry;
 mod resolution;
 mod resolvers;
@@ -62,12 +67,12 @@ pub enum CliNpmResolverManagedSnapshotOption {
   Specified(Option<ValidSerializedNpmResolutionSnapshot>),
 }
 
-pub struct CliNpmResolverManagedCreateOptions {
+pub struct CliManagedNpmResolverCreateOptions {
   pub snapshot: CliNpmResolverManagedSnapshotOption,
   pub maybe_lockfile: Option<Arc<CliLockfile>>,
   pub fs: Arc<dyn deno_runtime::deno_fs::FileSystem>,
   pub http_client_provider: Arc<crate::http_util::HttpClientProvider>,
-  pub npm_global_cache_dir: PathBuf,
+  pub npm_cache_dir: Arc<NpmCacheDir>,
   pub cache_setting: crate::args::CacheSetting,
   pub text_only_progress_bar: crate::util::progress_bar::ProgressBar,
   pub maybe_node_modules_path: Option<PathBuf>,
@@ -78,7 +83,7 @@ pub struct CliNpmResolverManagedCreateOptions {
 }
 
 pub async fn create_managed_npm_resolver_for_lsp(
-  options: CliNpmResolverManagedCreateOptions,
+  options: CliManagedNpmResolverCreateOptions,
 ) -> Arc<dyn CliNpmResolver> {
   let npm_cache = create_cache(&options);
   let npm_api = create_api(&options, npm_cache.clone());
@@ -111,7 +116,7 @@ pub async fn create_managed_npm_resolver_for_lsp(
 }
 
 pub async fn create_managed_npm_resolver(
-  options: CliNpmResolverManagedCreateOptions,
+  options: CliManagedNpmResolverCreateOptions,
 ) -> Result<Arc<dyn CliNpmResolver>, AnyError> {
   let npm_cache = create_cache(&options);
   let npm_api = create_api(&options, npm_cache.clone());
@@ -185,19 +190,16 @@ fn create_inner(
   ))
 }
 
-fn create_cache(options: &CliNpmResolverManagedCreateOptions) -> Arc<NpmCache> {
+fn create_cache(options: &CliManagedNpmResolverCreateOptions) -> Arc<NpmCache> {
   Arc::new(NpmCache::new(
-    NpmCacheDir::new(
-      options.npm_global_cache_dir.clone(),
-      options.npmrc.get_all_known_registries_urls(),
-    ),
+    options.npm_cache_dir.clone(),
     options.cache_setting.clone(),
     options.npmrc.clone(),
   ))
 }
 
 fn create_api(
-  options: &CliNpmResolverManagedCreateOptions,
+  options: &CliManagedNpmResolverCreateOptions,
   npm_cache: Arc<NpmCache>,
 ) -> Arc<CliNpmRegistryApi> {
   Arc::new(CliNpmRegistryApi::new(
@@ -254,6 +256,35 @@ async fn snapshot_from_lockfile(
   Ok(snapshot)
 }
 
+#[derive(Debug)]
+struct ManagedInNpmPackageChecker {
+  root_dir: Url,
+}
+
+impl InNpmPackageChecker for ManagedInNpmPackageChecker {
+  fn in_npm_package(&self, specifier: &Url) -> bool {
+    specifier.as_ref().starts_with(self.root_dir.as_str())
+  }
+}
+
+pub struct CliManagedInNpmPkgCheckerCreateOptions<'a> {
+  pub root_cache_dir_url: &'a Url,
+  pub maybe_node_modules_path: Option<&'a Path>,
+}
+
+pub fn create_managed_in_npm_pkg_checker(
+  options: CliManagedInNpmPkgCheckerCreateOptions,
+) -> Arc<dyn InNpmPackageChecker> {
+  let root_dir = match options.maybe_node_modules_path {
+    Some(node_modules_folder) => {
+      deno_path_util::url_from_directory_path(node_modules_folder).unwrap()
+    }
+    None => options.root_cache_dir_url.clone(),
+  };
+  debug_assert!(root_dir.as_str().ends_with('/'));
+  Arc::new(ManagedInNpmPackageChecker { root_dir })
+}
+
 /// An npm resolver where the resolution is managed by Deno rather than
 /// the user bringing their own node_modules (BYONM) on the file system.
 pub struct ManagedCliNpmResolver {
@@ -427,6 +458,16 @@ impl ManagedCliNpmResolver {
     self.resolution.snapshot()
   }
 
+  pub fn top_package_req_for_name(&self, name: &str) -> Option<PackageReq> {
+    let package_reqs = self.resolution.package_reqs();
+    let mut entries = package_reqs
+      .iter()
+      .filter(|(_, nv)| nv.name == name)
+      .collect::<Vec<_>>();
+    entries.sort_by_key(|(_, nv)| &nv.version);
+    Some(entries.last()?.0.clone())
+  }
+
   pub fn serialized_valid_snapshot_for_system(
     &self,
     system_info: &NpmSystemInfo,
@@ -466,6 +507,30 @@ impl ManagedCliNpmResolver {
     self.resolution.resolve_pkg_id_from_pkg_req(req)
   }
 
+  pub fn ensure_no_pkg_json_dep_errors(
+    &self,
+  ) -> Result<(), Box<PackageJsonDepValueParseWithLocationError>> {
+    for err in self.npm_install_deps_provider.pkg_json_dep_errors() {
+      match &err.source {
+        deno_package_json::PackageJsonDepValueParseError::VersionReq(_) => {
+          return Err(Box::new(err.clone()));
+        }
+        deno_package_json::PackageJsonDepValueParseError::Unsupported {
+          ..
+        } => {
+          // only warn for this one
+          log::warn!(
+            "{} {}\n    at {}",
+            colors::yellow("Warning"),
+            err.source,
+            err.location,
+          )
+        }
+      }
+    }
+    Ok(())
+  }
+
   /// Ensures that the top level `package.json` dependencies are installed.
   /// This may set up the `node_modules` directory.
   ///
@@ -477,6 +542,7 @@ impl ManagedCliNpmResolver {
     if !self.top_level_install_flag.raise() {
       return Ok(false); // already did this
     }
+
     let pkg_json_remote_pkgs = self.npm_install_deps_provider.remote_pkgs();
     if pkg_json_remote_pkgs.is_empty() {
       return Ok(false);
@@ -515,8 +581,16 @@ impl ManagedCliNpmResolver {
       .map_err(|err| err.into())
   }
 
-  pub fn global_cache_root_folder(&self) -> PathBuf {
-    self.npm_cache.root_folder()
+  pub fn maybe_node_modules_path(&self) -> Option<&Path> {
+    self.fs_resolver.node_modules_path()
+  }
+
+  pub fn global_cache_root_path(&self) -> &Path {
+    self.npm_cache.root_dir_path()
+  }
+
+  pub fn global_cache_root_url(&self) -> &Url {
+    self.npm_cache.root_dir_url()
   }
 }
 
@@ -532,7 +606,7 @@ fn npm_process_state(
   .unwrap()
 }
 
-impl NpmResolver for ManagedCliNpmResolver {
+impl NpmPackageFolderResolver for ManagedCliNpmResolver {
   fn resolve_package_folder_from_package(
     &self,
     name: &str,
@@ -551,39 +625,40 @@ impl NpmResolver for ManagedCliNpmResolver {
     log::debug!("Resolved {} from {} to {}", name, referrer, path.display());
     Ok(path)
   }
-
-  fn in_npm_package(&self, specifier: &ModuleSpecifier) -> bool {
-    let root_dir_url = self.fs_resolver.root_dir_url();
-    debug_assert!(root_dir_url.as_str().ends_with('/'));
-    specifier.as_ref().starts_with(root_dir_url.as_str())
-  }
-}
-
-impl NodeRequireResolver for ManagedCliNpmResolver {
-  fn ensure_read_permission(
-    &self,
-    permissions: &mut dyn NodePermissions,
-    path: &Path,
-  ) -> Result<(), AnyError> {
-    self.fs_resolver.ensure_read_permission(permissions, path)
-  }
 }
 
 impl NpmProcessStateProvider for ManagedCliNpmResolver {
   fn get_npm_process_state(&self) -> String {
     npm_process_state(
       self.resolution.serialized_valid_snapshot(),
-      self.fs_resolver.node_modules_path().map(|p| p.as_path()),
+      self.fs_resolver.node_modules_path(),
     )
   }
 }
 
+impl CliNpmReqResolver for ManagedCliNpmResolver {
+  fn resolve_pkg_folder_from_deno_module_req(
+    &self,
+    req: &PackageReq,
+    _referrer: &ModuleSpecifier,
+  ) -> Result<PathBuf, ResolvePkgFolderFromDenoReqError> {
+    let pkg_id = self
+      .resolve_pkg_id_from_pkg_req(req)
+      .map_err(|err| ResolvePkgFolderFromDenoReqError::Managed(err.into()))?;
+    self
+      .resolve_pkg_folder_from_pkg_id(&pkg_id)
+      .map_err(ResolvePkgFolderFromDenoReqError::Managed)
+  }
+}
+
 impl CliNpmResolver for ManagedCliNpmResolver {
-  fn into_npm_resolver(self: Arc<Self>) -> Arc<dyn NpmResolver> {
+  fn into_npm_pkg_folder_resolver(
+    self: Arc<Self>,
+  ) -> Arc<dyn NpmPackageFolderResolver> {
     self
   }
 
-  fn into_require_resolver(self: Arc<Self>) -> Arc<dyn NodeRequireResolver> {
+  fn into_npm_req_resolver(self: Arc<Self>) -> Arc<dyn CliNpmReqResolver> {
     self
   }
 
@@ -630,17 +705,16 @@ impl CliNpmResolver for ManagedCliNpmResolver {
     InnerCliNpmResolverRef::Managed(self)
   }
 
-  fn root_node_modules_path(&self) -> Option<&PathBuf> {
+  fn root_node_modules_path(&self) -> Option<&Path> {
     self.fs_resolver.node_modules_path()
   }
 
-  fn resolve_pkg_folder_from_deno_module_req(
+  fn ensure_read_permission<'a>(
     &self,
-    req: &PackageReq,
-    _referrer: &ModuleSpecifier,
-  ) -> Result<PathBuf, AnyError> {
-    let pkg_id = self.resolve_pkg_id_from_pkg_req(req)?;
-    self.resolve_pkg_folder_from_pkg_id(&pkg_id)
+    permissions: &mut dyn NodePermissions,
+    path: &'a Path,
+  ) -> Result<Cow<'a, Path>, AnyError> {
+    self.fs_resolver.ensure_read_permission(permissions, path)
   }
 
   fn check_state_hash(&self) -> Option<u64> {
diff --git a/cli/npm/managed/resolvers/common.rs b/cli/npm/managed/resolvers/common.rs
index 620daf4b30..eee11c7604 100644
--- a/cli/npm/managed/resolvers/common.rs
+++ b/cli/npm/managed/resolvers/common.rs
@@ -3,6 +3,7 @@
 pub mod bin_entries;
 pub mod lifecycle_scripts;
 
+use std::borrow::Cow;
 use std::collections::HashMap;
 use std::io::ErrorKind;
 use std::path::Path;
@@ -16,7 +17,6 @@ use deno_core::anyhow::Context;
 use deno_core::error::AnyError;
 use deno_core::futures;
 use deno_core::futures::StreamExt;
-use deno_core::url::Url;
 use deno_npm::NpmPackageCacheFolderId;
 use deno_npm::NpmPackageId;
 use deno_npm::NpmResolutionPackage;
@@ -29,11 +29,8 @@ use crate::npm::managed::cache::TarballCache;
 /// Part of the resolution that interacts with the file system.
 #[async_trait(?Send)]
 pub trait NpmPackageFsResolver: Send + Sync {
-  /// Specifier for the root directory.
-  fn root_dir_url(&self) -> &Url;
-
   /// The local node_modules folder if it is applicable to the implementation.
-  fn node_modules_path(&self) -> Option<&PathBuf>;
+  fn node_modules_path(&self) -> Option<&Path>;
 
   fn maybe_package_folder(&self, package_id: &NpmPackageId) -> Option<PathBuf>;
 
@@ -62,11 +59,12 @@ pub trait NpmPackageFsResolver: Send + Sync {
 
   async fn cache_packages(&self) -> Result<(), AnyError>;
 
-  fn ensure_read_permission(
+  #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
+  fn ensure_read_permission<'a>(
     &self,
     permissions: &mut dyn NodePermissions,
-    path: &Path,
-  ) -> Result<(), AnyError>;
+    path: &'a Path,
+  ) -> Result<Cow<'a, Path>, AnyError>;
 }
 
 #[derive(Debug)]
@@ -85,11 +83,15 @@ impl RegistryReadPermissionChecker {
     }
   }
 
-  pub fn ensure_registry_read_permission(
+  pub fn ensure_registry_read_permission<'a>(
     &self,
     permissions: &mut dyn NodePermissions,
-    path: &Path,
-  ) -> Result<(), AnyError> {
+    path: &'a Path,
+  ) -> Result<Cow<'a, Path>, AnyError> {
+    if permissions.query_read_all() {
+      return Ok(Cow::Borrowed(path)); // skip permissions checks below
+    }
+
     // allow reading if it's in the node_modules
     let is_path_in_node_modules = path.starts_with(&self.registry_path)
       && path
@@ -118,20 +120,20 @@ impl RegistryReadPermissionChecker {
             },
           }
         };
-      let Some(registry_path_canon) = canonicalize(&self.registry_path)? else {
-        return Ok(()); // not exists, allow reading
-      };
-      let Some(path_canon) = canonicalize(path)? else {
-        return Ok(()); // not exists, allow reading
-      };
-
-      if path_canon.starts_with(registry_path_canon) {
-        return Ok(());
+      if let Some(registry_path_canon) = canonicalize(&self.registry_path)? {
+        if let Some(path_canon) = canonicalize(path)? {
+          if path_canon.starts_with(registry_path_canon) {
+            return Ok(Cow::Owned(path_canon));
+          }
+        } else if path.starts_with(registry_path_canon)
+          || path.starts_with(&self.registry_path)
+        {
+          return Ok(Cow::Borrowed(path));
+        }
       }
     }
 
-    _ = permissions.check_read_path(path)?;
-    Ok(())
+    permissions.check_read_path(path).map_err(Into::into)
   }
 }
 
diff --git a/cli/npm/managed/resolvers/common/bin_entries.rs b/cli/npm/managed/resolvers/common/bin_entries.rs
index 4524ce8326..e4a1845689 100644
--- a/cli/npm/managed/resolvers/common/bin_entries.rs
+++ b/cli/npm/managed/resolvers/common/bin_entries.rs
@@ -18,6 +18,7 @@ pub struct BinEntries<'a> {
   seen_names: HashMap<&'a str, &'a NpmPackageId>,
   /// The bin entries
   entries: Vec<(&'a NpmResolutionPackage, PathBuf)>,
+  sorted: bool,
 }
 
 /// Returns the name of the default binary for the given package.
@@ -31,6 +32,20 @@ fn default_bin_name(package: &NpmResolutionPackage) -> &str {
     .map_or(package.id.nv.name.as_str(), |(_, name)| name)
 }
 
+pub fn warn_missing_entrypoint(
+  bin_name: &str,
+  package_path: &Path,
+  entrypoint: &Path,
+) {
+  log::warn!(
+    "{} Trying to set up '{}' bin for \"{}\", but the entry point \"{}\" doesn't exist.",
+    deno_terminal::colors::yellow("Warning"),
+    bin_name,
+    package_path.display(),
+    entrypoint.display()
+  );
+}
+
 impl<'a> BinEntries<'a> {
   pub fn new() -> Self {
     Self::default()
@@ -42,6 +57,7 @@ impl<'a> BinEntries<'a> {
     package: &'a NpmResolutionPackage,
     package_path: PathBuf,
   ) {
+    self.sorted = false;
     // check for a new collision, if we haven't already
     // found one
     match package.bin.as_ref().unwrap() {
@@ -79,16 +95,21 @@ impl<'a> BinEntries<'a> {
       &str, // bin name
       &str, // bin script
     ) -> Result<(), AnyError>,
+    mut filter: impl FnMut(&NpmResolutionPackage) -> bool,
   ) -> Result<(), AnyError> {
-    if !self.collisions.is_empty() {
+    if !self.collisions.is_empty() && !self.sorted {
       // walking the dependency tree to find out the depth of each package
       // is sort of expensive, so we only do it if there's a collision
       sort_by_depth(snapshot, &mut self.entries, &mut self.collisions);
+      self.sorted = true;
     }
 
     let mut seen = HashSet::new();
 
     for (package, package_path) in &self.entries {
+      if !filter(package) {
+        continue;
+      }
       if let Some(bin_entries) = &package.bin {
         match bin_entries {
           deno_npm::registry::NpmPackageVersionBinEntry::String(script) => {
@@ -118,8 +139,8 @@ impl<'a> BinEntries<'a> {
   }
 
   /// Collect the bin entries into a vec of (name, script path)
-  pub fn into_bin_files(
-    mut self,
+  pub fn collect_bin_files(
+    &mut self,
     snapshot: &NpmResolutionSnapshot,
   ) -> Vec<(String, PathBuf)> {
     let mut bins = Vec::new();
@@ -131,17 +152,18 @@ impl<'a> BinEntries<'a> {
           bins.push((name.to_string(), package_path.join(script)));
           Ok(())
         },
+        |_| true,
       )
       .unwrap();
     bins
   }
 
-  /// Finish setting up the bin entries, writing the necessary files
-  /// to disk.
-  pub fn finish(
+  fn set_up_entries_filtered(
     mut self,
     snapshot: &NpmResolutionSnapshot,
     bin_node_modules_dir_path: &Path,
+    filter: impl FnMut(&NpmResolutionPackage) -> bool,
+    mut handler: impl FnMut(&EntrySetupOutcome<'_>),
   ) -> Result<(), AnyError> {
     if !self.entries.is_empty() && !bin_node_modules_dir_path.exists() {
       std::fs::create_dir_all(bin_node_modules_dir_path).with_context(
@@ -160,18 +182,54 @@ impl<'a> BinEntries<'a> {
         Ok(())
       },
       |package, package_path, name, script| {
-        set_up_bin_entry(
+        let outcome = set_up_bin_entry(
           package,
           name,
           script,
           package_path,
           bin_node_modules_dir_path,
-        )
+        )?;
+        handler(&outcome);
+        Ok(())
       },
+      filter,
     )?;
 
     Ok(())
   }
+
+  /// Finish setting up the bin entries, writing the necessary files
+  /// to disk.
+  pub fn finish(
+    self,
+    snapshot: &NpmResolutionSnapshot,
+    bin_node_modules_dir_path: &Path,
+    handler: impl FnMut(&EntrySetupOutcome<'_>),
+  ) -> Result<(), AnyError> {
+    self.set_up_entries_filtered(
+      snapshot,
+      bin_node_modules_dir_path,
+      |_| true,
+      handler,
+    )
+  }
+
+  /// Finish setting up the bin entries, writing the necessary files
+  /// to disk.
+  pub fn finish_only(
+    self,
+    snapshot: &NpmResolutionSnapshot,
+    bin_node_modules_dir_path: &Path,
+    handler: impl FnMut(&EntrySetupOutcome<'_>),
+    only: &HashSet<&NpmPackageId>,
+  ) -> Result<(), AnyError> {
+    self.set_up_entries_filtered(
+      snapshot,
+      bin_node_modules_dir_path,
+      |package| only.contains(&package.id),
+      handler,
+    )
+  }
 }
 
 // walk the dependency tree to find out the depth of each package
@@ -233,16 +291,17 @@ fn sort_by_depth(
   });
 }
 
-pub fn set_up_bin_entry(
-  package: &NpmResolutionPackage,
-  bin_name: &str,
+pub fn set_up_bin_entry<'a>(
+  package: &'a NpmResolutionPackage,
+  bin_name: &'a str,
   #[allow(unused_variables)] bin_script: &str,
-  #[allow(unused_variables)] package_path: &Path,
+  #[allow(unused_variables)] package_path: &'a Path,
   bin_node_modules_dir_path: &Path,
-) -> Result<(), AnyError> {
+) -> Result<EntrySetupOutcome<'a>, AnyError> {
   #[cfg(windows)]
   {
     set_up_bin_shim(package, bin_name, bin_node_modules_dir_path)?;
+    Ok(EntrySetupOutcome::Success)
   }
   #[cfg(unix)]
   {
@@ -252,9 +311,8 @@ pub fn set_up_bin_entry(
       bin_script,
       package_path,
       bin_node_modules_dir_path,
-    )?;
+    )
   }
-  Ok(())
 }
 
 #[cfg(windows)]
@@ -301,14 +359,39 @@ fn make_executable_if_exists(path: &Path) -> Result<bool, AnyError> {
   Ok(true)
 }
 
+pub enum EntrySetupOutcome<'a> {
+  #[cfg_attr(windows, allow(dead_code))]
+  MissingEntrypoint {
+    bin_name: &'a str,
+    package_path: &'a Path,
+    entrypoint: PathBuf,
+    package: &'a NpmResolutionPackage,
+  },
+  Success,
+}
+
+impl<'a> EntrySetupOutcome<'a> {
+  pub fn warn_if_failed(&self) {
+    match self {
+      EntrySetupOutcome::MissingEntrypoint {
+        bin_name,
+        package_path,
+        entrypoint,
+        ..
+      } => warn_missing_entrypoint(bin_name, package_path, entrypoint),
+      EntrySetupOutcome::Success => {}
+    }
+  }
+}
+
 #[cfg(unix)]
-fn symlink_bin_entry(
-  _package: &NpmResolutionPackage,
-  bin_name: &str,
+fn symlink_bin_entry<'a>(
+  package: &'a NpmResolutionPackage,
+  bin_name: &'a str,
   bin_script: &str,
-  package_path: &Path,
+  package_path: &'a Path,
   bin_node_modules_dir_path: &Path,
-) -> Result<(), AnyError> {
+) -> Result<EntrySetupOutcome<'a>, AnyError> {
   use std::io;
   use std::os::unix::fs::symlink;
   let link = bin_node_modules_dir_path.join(bin_name);
@@ -318,14 +401,12 @@ fn symlink_bin_entry(
     format!("Can't set up '{}' bin at {}", bin_name, original.display())
   })?;
   if !found {
-    log::warn!(
-      "{} Trying to set up '{}' bin for \"{}\", but the entry point \"{}\" doesn't exist.",
-      deno_terminal::colors::yellow("Warning"),
+    return Ok(EntrySetupOutcome::MissingEntrypoint {
       bin_name,
-      package_path.display(),
-      original.display()
-    );
-    return Ok(());
+      package_path,
+      entrypoint: original,
+      package,
+    });
   }
 
   let original_relative =
@@ -348,7 +429,7 @@ fn symlink_bin_entry(
           original_relative.display()
         )
       })?;
-      return Ok(());
+      return Ok(EntrySetupOutcome::Success);
     }
     return Err(err).with_context(|| {
       format!(
@@ -359,5 +440,5 @@ fn symlink_bin_entry(
     });
   }
 
-  Ok(())
+  Ok(EntrySetupOutcome::Success)
 }
diff --git a/cli/npm/managed/resolvers/common/lifecycle_scripts.rs b/cli/npm/managed/resolvers/common/lifecycle_scripts.rs
index b358c35856..5c5755c819 100644
--- a/cli/npm/managed/resolvers/common/lifecycle_scripts.rs
+++ b/cli/npm/managed/resolvers/common/lifecycle_scripts.rs
@@ -2,12 +2,15 @@
 
 use super::bin_entries::BinEntries;
 use crate::args::LifecycleScriptsConfig;
+use crate::task_runner::TaskStdio;
+use crate::util::progress_bar::ProgressBar;
 use deno_core::anyhow::Context;
 use deno_npm::resolution::NpmResolutionSnapshot;
 use deno_runtime::deno_io::FromRawIoHandle;
 use deno_semver::package::PackageNv;
 use deno_semver::Version;
 use std::borrow::Cow;
+use std::collections::HashSet;
 use std::rc::Rc;
 
 use std::path::Path;
@@ -59,7 +62,7 @@ impl<'a> LifecycleScripts<'a> {
   }
 }
 
-fn has_lifecycle_scripts(
+pub fn has_lifecycle_scripts(
   package: &NpmResolutionPackage,
   package_path: &Path,
 ) -> bool {
@@ -81,7 +84,7 @@ fn is_broken_default_install_script(script: &str, package_path: &Path) -> bool {
 }
 
 impl<'a> LifecycleScripts<'a> {
-  fn can_run_scripts(&self, package_nv: &PackageNv) -> bool {
+  pub fn can_run_scripts(&self, package_nv: &PackageNv) -> bool {
     if !self.strategy.can_run_scripts() {
       return false;
     }
@@ -96,6 +99,9 @@ impl<'a> LifecycleScripts<'a> {
       PackagesAllowedScripts::None => false,
     }
   }
+  pub fn has_run_scripts(&self, package: &NpmResolutionPackage) -> bool {
+    self.strategy.has_run(package)
+  }
   /// Register a package for running lifecycle scripts, if applicable.
   ///
   /// `package_path` is the path containing the package's code (its root dir).
@@ -108,12 +114,12 @@ impl<'a> LifecycleScripts<'a> {
   ) {
     if has_lifecycle_scripts(package, &package_path) {
       if self.can_run_scripts(&package.id.nv) {
-        if !self.strategy.has_run(package) {
+        if !self.has_run_scripts(package) {
           self
             .packages_with_scripts
             .push((package, package_path.into_owned()));
         }
-      } else if !self.strategy.has_run(package)
+      } else if !self.has_run_scripts(package)
         && (self.config.explicit_install || !self.strategy.has_warned(package))
       {
         // Skip adding `esbuild` as it is known that it can work properly without lifecycle script
@@ -147,21 +153,32 @@ impl<'a> LifecycleScripts<'a> {
     self,
     snapshot: &NpmResolutionSnapshot,
     packages: &[NpmResolutionPackage],
-    root_node_modules_dir_path: Option<&Path>,
+    root_node_modules_dir_path: &Path,
+    progress_bar: &ProgressBar,
   ) -> Result<(), AnyError> {
     self.warn_not_run_scripts()?;
     let get_package_path =
       |p: &NpmResolutionPackage| self.strategy.package_path(p);
     let mut failed_packages = Vec::new();
+    let mut bin_entries = BinEntries::new();
     if !self.packages_with_scripts.is_empty() {
+      let package_ids = self
+        .packages_with_scripts
+        .iter()
+        .map(|(p, _)| &p.id)
+        .collect::<HashSet<_>>();
       // get custom commands for each bin available in the node_modules dir (essentially
       // the scripts that are in `node_modules/.bin`)
-      let base =
-        resolve_baseline_custom_commands(snapshot, packages, get_package_path)?;
+      let base = resolve_baseline_custom_commands(
+        &mut bin_entries,
+        snapshot,
+        packages,
+        get_package_path,
+      )?;
       let init_cwd = &self.config.initial_cwd;
       let process_state = crate::npm::managed::npm_process_state(
         snapshot.as_valid_serialized(),
-        root_node_modules_dir_path,
+        Some(root_node_modules_dir_path),
       );
 
       let mut env_vars = crate::task_runner::real_env_vars();
@@ -201,7 +218,15 @@ impl<'a> LifecycleScripts<'a> {
             {
               continue;
             }
-            let exit_code = crate::task_runner::run_task(
+            let _guard = progress_bar.update_with_prompt(
+              crate::util::progress_bar::ProgressMessagePrompt::Initialize,
+              &format!("{}: running '{script_name}' script", package.id.nv),
+            );
+            let crate::task_runner::TaskResult {
+              exit_code,
+              stderr,
+              stdout,
+            } = crate::task_runner::run_task(
               crate::task_runner::RunTaskOptions {
                 task_name: script_name,
                 script,
@@ -210,16 +235,38 @@ impl<'a> LifecycleScripts<'a> {
                 custom_commands: custom_commands.clone(),
                 init_cwd,
                 argv: &[],
-                root_node_modules_dir: root_node_modules_dir_path,
+                root_node_modules_dir: Some(root_node_modules_dir_path),
+                stdio: Some(crate::task_runner::TaskIo {
+                  stderr: TaskStdio::piped(),
+                  stdout: TaskStdio::piped(),
+                }),
               },
             )
             .await?;
+            let stdout = stdout.unwrap();
+            let stderr = stderr.unwrap();
             if exit_code != 0 {
               log::warn!(
-                "error: script '{}' in '{}' failed with exit code {}",
+                "error: script '{}' in '{}' failed with exit code {}{}{}",
                 script_name,
                 package.id.nv,
                 exit_code,
+                if !stdout.trim_ascii().is_empty() {
+                  format!(
+                    "\nstdout:\n{}\n",
+                    String::from_utf8_lossy(&stdout).trim()
+                  )
+                } else {
+                  String::new()
+                },
+                if !stderr.trim_ascii().is_empty() {
+                  format!(
+                    "\nstderr:\n{}\n",
+                    String::from_utf8_lossy(&stderr).trim()
+                  )
+                } else {
+                  String::new()
+                },
               );
               failed_packages.push(&package.id.nv);
               // assume if earlier script fails, later ones will fail too
@@ -229,6 +276,17 @@ impl<'a> LifecycleScripts<'a> {
         }
         self.strategy.did_run_scripts(package)?;
       }
+
+      // re-set up bin entries for the packages which we've run scripts for.
+      // lifecycle scripts can create files that are linked to by bin entries,
+      // and the only reliable way to handle this is to re-link bin entries
+      // (this is what PNPM does as well)
+      bin_entries.finish_only(
+        snapshot,
+        &root_node_modules_dir_path.join(".bin"),
+        |outcome| outcome.warn_if_failed(),
+        &package_ids,
+      )?;
     }
     if failed_packages.is_empty() {
       Ok(())
@@ -248,9 +306,10 @@ impl<'a> LifecycleScripts<'a> {
 // take in all (non copy) packages from snapshot,
 // and resolve the set of available binaries to create
 // custom commands available to the task runner
-fn resolve_baseline_custom_commands(
-  snapshot: &NpmResolutionSnapshot,
-  packages: &[NpmResolutionPackage],
+fn resolve_baseline_custom_commands<'a>(
+  bin_entries: &mut BinEntries<'a>,
+  snapshot: &'a NpmResolutionSnapshot,
+  packages: &'a [NpmResolutionPackage],
   get_package_path: impl Fn(&NpmResolutionPackage) -> PathBuf,
 ) -> Result<crate::task_runner::TaskCustomCommands, AnyError> {
   let mut custom_commands = crate::task_runner::TaskCustomCommands::new();
@@ -273,6 +332,7 @@ fn resolve_baseline_custom_commands(
   // doing it for packages that are set up already.
   // realistically, scripts won't be run very often so it probably isn't too big of an issue.
   resolve_custom_commands_from_packages(
+    bin_entries,
     custom_commands,
     snapshot,
     packages,
@@ -287,12 +347,12 @@ fn resolve_custom_commands_from_packages<
   'a,
   P: IntoIterator<Item = &'a NpmResolutionPackage>,
 >(
+  bin_entries: &mut BinEntries<'a>,
   mut commands: crate::task_runner::TaskCustomCommands,
   snapshot: &'a NpmResolutionSnapshot,
   packages: P,
   get_package_path: impl Fn(&'a NpmResolutionPackage) -> PathBuf,
 ) -> Result<crate::task_runner::TaskCustomCommands, AnyError> {
-  let mut bin_entries = BinEntries::new();
   for package in packages {
     let package_path = get_package_path(package);
 
@@ -300,7 +360,7 @@ fn resolve_custom_commands_from_packages<
       bin_entries.add(package, package_path);
     }
   }
-  let bins = bin_entries.into_bin_files(snapshot);
+  let bins: Vec<(String, PathBuf)> = bin_entries.collect_bin_files(snapshot);
   for (bin_name, script_path) in bins {
     commands.insert(
       bin_name.clone(),
@@ -323,7 +383,9 @@ fn resolve_custom_commands_from_deps(
   snapshot: &NpmResolutionSnapshot,
   get_package_path: impl Fn(&NpmResolutionPackage) -> PathBuf,
 ) -> Result<crate::task_runner::TaskCustomCommands, AnyError> {
+  let mut bin_entries = BinEntries::new();
   resolve_custom_commands_from_packages(
+    &mut bin_entries,
     baseline,
     snapshot,
     package
diff --git a/cli/npm/managed/resolvers/global.rs b/cli/npm/managed/resolvers/global.rs
index 187e6b2774..f0193e78e9 100644
--- a/cli/npm/managed/resolvers/global.rs
+++ b/cli/npm/managed/resolvers/global.rs
@@ -11,7 +11,6 @@ use crate::colors;
 use async_trait::async_trait;
 use deno_ast::ModuleSpecifier;
 use deno_core::error::AnyError;
-use deno_core::url::Url;
 use deno_npm::NpmPackageCacheFolderId;
 use deno_npm::NpmPackageId;
 use deno_npm::NpmResolutionPackage;
@@ -56,7 +55,7 @@ impl GlobalNpmPackageResolver {
     Self {
       registry_read_permission_checker: RegistryReadPermissionChecker::new(
         fs,
-        cache.root_folder(),
+        cache.root_dir_path().to_path_buf(),
       ),
       cache,
       tarball_cache,
@@ -69,11 +68,7 @@ impl GlobalNpmPackageResolver {
 
 #[async_trait(?Send)]
 impl NpmPackageFsResolver for GlobalNpmPackageResolver {
-  fn root_dir_url(&self) -> &Url {
-    self.cache.root_dir_url()
-  }
-
-  fn node_modules_path(&self) -> Option<&PathBuf> {
+  fn node_modules_path(&self) -> Option<&Path> {
     None
   }
 
@@ -183,11 +178,11 @@ impl NpmPackageFsResolver for GlobalNpmPackageResolver {
     Ok(())
   }
 
-  fn ensure_read_permission(
+  fn ensure_read_permission<'a>(
     &self,
     permissions: &mut dyn NodePermissions,
-    path: &Path,
-  ) -> Result<(), AnyError> {
+    path: &'a Path,
+  ) -> Result<Cow<'a, Path>, AnyError> {
     self
       .registry_read_permission_checker
       .ensure_registry_read_permission(permissions, path)
diff --git a/cli/npm/managed/resolvers/local.rs b/cli/npm/managed/resolvers/local.rs
index 5a90f252de..50c5bd2689 100644
--- a/cli/npm/managed/resolvers/local.rs
+++ b/cli/npm/managed/resolvers/local.rs
@@ -19,6 +19,7 @@ use crate::args::LifecycleScriptsConfig;
 use crate::colors;
 use async_trait::async_trait;
 use deno_ast::ModuleSpecifier;
+use deno_cache_dir::npm::mixed_case_package_name_decode;
 use deno_core::anyhow::Context;
 use deno_core::error::AnyError;
 use deno_core::futures::stream::FuturesUnordered;
@@ -30,6 +31,7 @@ use deno_npm::NpmPackageCacheFolderId;
 use deno_npm::NpmPackageId;
 use deno_npm::NpmResolutionPackage;
 use deno_npm::NpmSystemInfo;
+use deno_resolver::npm::normalize_pkg_name_for_node_modules_deno_folder;
 use deno_runtime::deno_fs;
 use deno_runtime::deno_node::NodePermissions;
 use deno_semver::package::PackageNv;
@@ -42,8 +44,6 @@ use serde::Serialize;
 
 use crate::args::NpmInstallDepsProvider;
 use crate::cache::CACHE_PERM;
-use crate::npm::cache_dir::mixed_case_package_name_decode;
-use crate::npm::cache_dir::mixed_case_package_name_encode;
 use crate::util::fs::atomic_write_file_with_retries;
 use crate::util::fs::canonicalize_path_maybe_not_exists_with_fs;
 use crate::util::fs::clone_dir_recursive;
@@ -55,6 +55,7 @@ use crate::util::progress_bar::ProgressMessagePrompt;
 use super::super::cache::NpmCache;
 use super::super::cache::TarballCache;
 use super::super::resolution::NpmResolution;
+use super::common::bin_entries;
 use super::common::NpmPackageFsResolver;
 use super::common::RegistryReadPermissionChecker;
 
@@ -155,12 +156,8 @@ impl LocalNpmPackageResolver {
 
 #[async_trait(?Send)]
 impl NpmPackageFsResolver for LocalNpmPackageResolver {
-  fn root_dir_url(&self) -> &Url {
-    &self.root_node_modules_url
-  }
-
-  fn node_modules_path(&self) -> Option<&PathBuf> {
-    Some(&self.root_node_modules_path)
+  fn node_modules_path(&self) -> Option<&Path> {
+    Some(self.root_node_modules_path.as_ref())
   }
 
   fn maybe_package_folder(&self, id: &NpmPackageId) -> Option<PathBuf> {
@@ -257,11 +254,11 @@ impl NpmPackageFsResolver for LocalNpmPackageResolver {
     .await
   }
 
-  fn ensure_read_permission(
+  fn ensure_read_permission<'a>(
     &self,
     permissions: &mut dyn NodePermissions,
-    path: &Path,
-  ) -> Result<(), AnyError> {
+    path: &'a Path,
+  ) -> Result<Cow<'a, Path>, AnyError> {
     self
       .registry_read_permission_checker
       .ensure_registry_read_permission(permissions, path)
@@ -333,8 +330,7 @@ async fn sync_resolution_with_fs(
   let mut cache_futures = FuturesUnordered::new();
   let mut newest_packages_by_name: HashMap<&String, &NpmResolutionPackage> =
     HashMap::with_capacity(package_partitions.packages.len());
-  let bin_entries =
-    Rc::new(RefCell::new(super::common::bin_entries::BinEntries::new()));
+  let bin_entries = Rc::new(RefCell::new(bin_entries::BinEntries::new()));
   let mut lifecycle_scripts =
     super::common::lifecycle_scripts::LifecycleScripts::new(
       lifecycle_scripts,
@@ -343,6 +339,14 @@ async fn sync_resolution_with_fs(
       },
     );
   let packages_with_deprecation_warnings = Arc::new(Mutex::new(Vec::new()));
+
+  let mut package_tags: HashMap<&PackageNv, Vec<&str>> = HashMap::new();
+  for (package_req, package_nv) in snapshot.package_reqs() {
+    if let Some(tag) = package_req.version_req.tag() {
+      package_tags.entry(package_nv).or_default().push(tag);
+    }
+  }
+
   for package in &package_partitions.packages {
     if let Some(current_pkg) =
       newest_packages_by_name.get_mut(&package.id.nv.name)
@@ -357,11 +361,29 @@ async fn sync_resolution_with_fs(
     let package_folder_name =
       get_package_folder_id_folder_name(&package.get_package_cache_folder_id());
     let folder_path = deno_local_registry_dir.join(&package_folder_name);
+    let tags = package_tags
+      .get(&package.id.nv)
+      .map(|tags| tags.join(","))
+      .unwrap_or_default();
+    enum PackageFolderState {
+      UpToDate,
+      Uninitialized,
+      TagsOutdated,
+    }
     let initialized_file = folder_path.join(".initialized");
+    let package_state = std::fs::read_to_string(&initialized_file)
+      .map(|s| {
+        if s != tags {
+          PackageFolderState::TagsOutdated
+        } else {
+          PackageFolderState::UpToDate
+        }
+      })
+      .unwrap_or(PackageFolderState::Uninitialized);
     if !cache
       .cache_setting()
       .should_use_for_npm_package(&package.id.nv.name)
-      || !initialized_file.exists()
+      || matches!(package_state, PackageFolderState::Uninitialized)
     {
       // cache bust the dep from the dep setup cache so the symlinks
       // are forced to be recreated
@@ -371,6 +393,7 @@ async fn sync_resolution_with_fs(
       let bin_entries_to_setup = bin_entries.clone();
       let packages_with_deprecation_warnings =
         packages_with_deprecation_warnings.clone();
+
       cache_futures.push(async move {
         tarball_cache
           .ensure_package(&package.id.nv, &package.dist)
@@ -389,7 +412,7 @@ async fn sync_resolution_with_fs(
           move || {
             clone_dir_recursive(&cache_folder, &package_path)?;
             // write out a file that indicates this folder has been initialized
-            fs::write(initialized_file, "")?;
+            fs::write(initialized_file, tags)?;
 
             Ok::<_, AnyError>(())
           }
@@ -410,6 +433,8 @@ async fn sync_resolution_with_fs(
         drop(pb_guard); // explicit for clarity
         Ok::<_, AnyError>(())
       });
+    } else if matches!(package_state, PackageFolderState::TagsOutdated) {
+      fs::write(initialized_file, tags)?;
     }
 
     let sub_node_modules = folder_path.join("node_modules");
@@ -518,9 +543,9 @@ async fn sync_resolution_with_fs(
         // linked into the root
         match found_names.entry(remote_alias) {
           Entry::Occupied(nv) => {
-            alias_clashes
-              || remote.req.name != nv.get().name // alias to a different package (in case of duplicate aliases)
-              || !remote.req.version_req.matches(&nv.get().version) // incompatible version
+            // alias to a different package (in case of duplicate aliases)
+            // or the version doesn't match the version in the root node_modules
+            alias_clashes || &remote_pkg.id.nv != *nv.get()
           }
           Entry::Vacant(entry) => {
             entry.insert(&remote_pkg.id.nv);
@@ -633,7 +658,28 @@ async fn sync_resolution_with_fs(
   // 7. Set up `node_modules/.bin` entries for packages that need it.
   {
     let bin_entries = std::mem::take(&mut *bin_entries.borrow_mut());
-    bin_entries.finish(snapshot, &bin_node_modules_dir_path)?;
+    bin_entries.finish(
+      snapshot,
+      &bin_node_modules_dir_path,
+      |setup_outcome| {
+        match setup_outcome {
+          bin_entries::EntrySetupOutcome::MissingEntrypoint {
+            package,
+            package_path,
+            ..
+          } if super::common::lifecycle_scripts::has_lifecycle_scripts(
+            package,
+            package_path,
+          ) && lifecycle_scripts.can_run_scripts(&package.id.nv)
+            && !lifecycle_scripts.has_run_scripts(package) =>
+          {
+            // ignore, it might get fixed when the lifecycle scripts run.
+            // if not, we'll warn then
+          }
+          outcome => outcome.warn_if_failed(),
+        }
+      },
+    )?;
   }
 
   // 8. Create symlinks for the workspace packages
@@ -683,7 +729,8 @@ async fn sync_resolution_with_fs(
     .finish(
       snapshot,
       &package_partitions.packages,
-      Some(root_node_modules_dir_path),
+      root_node_modules_dir_path,
+      progress_bar,
     )
     .await?;
 
@@ -920,20 +967,6 @@ impl SetupCache {
   }
 }
 
-/// Normalizes a package name for use at `node_modules/.deno/<pkg-name>@<version>[_<copy_index>]`
-pub fn normalize_pkg_name_for_node_modules_deno_folder(name: &str) -> Cow<str> {
-  let name = if name.to_lowercase() == name {
-    Cow::Borrowed(name)
-  } else {
-    Cow::Owned(format!("_{}", mixed_case_package_name_encode(name)))
-  };
-  if name.starts_with('@') {
-    name.replace('/', "+").into()
-  } else {
-    name
-  }
-}
-
 fn get_package_folder_id_folder_name(
   folder_id: &NpmPackageCacheFolderId,
 ) -> String {
@@ -1023,12 +1056,18 @@ fn junction_or_symlink_dir(
       if symlink_err.kind() == std::io::ErrorKind::PermissionDenied =>
     {
       USE_JUNCTIONS.store(true, std::sync::atomic::Ordering::Relaxed);
-      junction::create(old_path, new_path).map_err(Into::into)
+      junction::create(old_path, new_path)
+        .context("Failed creating junction in node_modules folder")
+    }
+    Err(symlink_err) => {
+      log::warn!(
+        "{} Unexpected error symlinking node_modules: {symlink_err}",
+        colors::yellow("Warning")
+      );
+      USE_JUNCTIONS.store(true, std::sync::atomic::Ordering::Relaxed);
+      junction::create(old_path, new_path)
+        .context("Failed creating junction in node_modules folder")
     }
-    Err(symlink_err) => Err(
-      AnyError::from(symlink_err)
-        .context("Failed creating symlink in node_modules folder"),
-    ),
   }
 }
 
diff --git a/cli/npm/managed/resolvers/mod.rs b/cli/npm/managed/resolvers/mod.rs
index 234a6e4dba..36d795ee7e 100644
--- a/cli/npm/managed/resolvers/mod.rs
+++ b/cli/npm/managed/resolvers/mod.rs
@@ -15,7 +15,6 @@ use crate::args::NpmInstallDepsProvider;
 use crate::util::progress_bar::ProgressBar;
 
 pub use self::common::NpmPackageFsResolver;
-pub use self::local::normalize_pkg_name_for_node_modules_deno_folder;
 
 use self::global::GlobalNpmPackageResolver;
 use self::local::LocalNpmPackageResolver;
diff --git a/cli/npm/mod.rs b/cli/npm/mod.rs
index 15ac8ebb28..0e955ac5b4 100644
--- a/cli/npm/mod.rs
+++ b/cli/npm/mod.rs
@@ -1,37 +1,44 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 mod byonm;
-mod cache_dir;
 mod common;
 mod managed;
 
-use std::path::PathBuf;
+use std::borrow::Cow;
+use std::path::Path;
 use std::sync::Arc;
 
+use common::maybe_auth_header_for_npm_registry;
 use dashmap::DashMap;
-use deno_ast::ModuleSpecifier;
 use deno_core::error::AnyError;
 use deno_core::serde_json;
+use deno_npm::npm_rc::ResolvedNpmRc;
 use deno_npm::registry::NpmPackageInfo;
-use deno_runtime::deno_node::NodeRequireResolver;
+use deno_resolver::npm::ByonmInNpmPackageChecker;
+use deno_resolver::npm::ByonmNpmResolver;
+use deno_resolver::npm::CliNpmReqResolver;
+use deno_resolver::npm::ResolvePkgFolderFromDenoReqError;
+use deno_runtime::deno_node::NodePermissions;
 use deno_runtime::ops::process::NpmProcessStateProvider;
 use deno_semver::package::PackageNv;
 use deno_semver::package::PackageReq;
-use node_resolver::NpmResolver;
+use managed::cache::registry_info::get_package_url;
+use managed::create_managed_in_npm_pkg_checker;
+use node_resolver::InNpmPackageChecker;
+use node_resolver::NpmPackageFolderResolver;
 
-use crate::args::npm_registry_url;
 use crate::file_fetcher::FileFetcher;
 
-pub use self::byonm::ByonmCliNpmResolver;
-pub use self::byonm::CliNpmResolverByonmCreateOptions;
-pub use self::cache_dir::NpmCacheDir;
-pub use self::managed::CliNpmResolverManagedCreateOptions;
+pub use self::byonm::CliByonmNpmResolver;
+pub use self::byonm::CliByonmNpmResolverCreateOptions;
+pub use self::managed::CliManagedInNpmPkgCheckerCreateOptions;
+pub use self::managed::CliManagedNpmResolverCreateOptions;
 pub use self::managed::CliNpmResolverManagedSnapshotOption;
 pub use self::managed::ManagedCliNpmResolver;
 
 pub enum CliNpmResolverCreateOptions {
-  Managed(CliNpmResolverManagedCreateOptions),
-  Byonm(CliNpmResolverByonmCreateOptions),
+  Managed(CliManagedNpmResolverCreateOptions),
+  Byonm(CliByonmNpmResolverCreateOptions),
 }
 
 pub async fn create_cli_npm_resolver_for_lsp(
@@ -42,7 +49,7 @@ pub async fn create_cli_npm_resolver_for_lsp(
     Managed(options) => {
       managed::create_managed_npm_resolver_for_lsp(options).await
     }
-    Byonm(options) => byonm::create_byonm_npm_resolver(options),
+    Byonm(options) => Arc::new(ByonmNpmResolver::new(options)),
   }
 }
 
@@ -52,22 +59,43 @@ pub async fn create_cli_npm_resolver(
   use CliNpmResolverCreateOptions::*;
   match options {
     Managed(options) => managed::create_managed_npm_resolver(options).await,
-    Byonm(options) => Ok(byonm::create_byonm_npm_resolver(options)),
+    Byonm(options) => Ok(Arc::new(ByonmNpmResolver::new(options))),
+  }
+}
+
+pub enum CreateInNpmPkgCheckerOptions<'a> {
+  Managed(CliManagedInNpmPkgCheckerCreateOptions<'a>),
+  Byonm,
+}
+
+pub fn create_in_npm_pkg_checker(
+  options: CreateInNpmPkgCheckerOptions,
+) -> Arc<dyn InNpmPackageChecker> {
+  match options {
+    CreateInNpmPkgCheckerOptions::Managed(options) => {
+      create_managed_in_npm_pkg_checker(options)
+    }
+    CreateInNpmPkgCheckerOptions::Byonm => Arc::new(ByonmInNpmPackageChecker),
   }
 }
 
 pub enum InnerCliNpmResolverRef<'a> {
   Managed(&'a ManagedCliNpmResolver),
   #[allow(dead_code)]
-  Byonm(&'a ByonmCliNpmResolver),
+  Byonm(&'a CliByonmNpmResolver),
 }
 
-pub trait CliNpmResolver: NpmResolver {
-  fn into_npm_resolver(self: Arc<Self>) -> Arc<dyn NpmResolver>;
-  fn into_require_resolver(self: Arc<Self>) -> Arc<dyn NodeRequireResolver>;
+pub trait CliNpmResolver: NpmPackageFolderResolver + CliNpmReqResolver {
+  fn into_npm_pkg_folder_resolver(
+    self: Arc<Self>,
+  ) -> Arc<dyn NpmPackageFolderResolver>;
+  fn into_npm_req_resolver(self: Arc<Self>) -> Arc<dyn CliNpmReqResolver>;
   fn into_process_state_provider(
     self: Arc<Self>,
   ) -> Arc<dyn NpmProcessStateProvider>;
+  fn into_maybe_byonm(self: Arc<Self>) -> Option<Arc<CliByonmNpmResolver>> {
+    None
+  }
 
   fn clone_snapshotted(&self) -> Arc<dyn CliNpmResolver>;
 
@@ -80,20 +108,20 @@ pub trait CliNpmResolver: NpmResolver {
     }
   }
 
-  fn as_byonm(&self) -> Option<&ByonmCliNpmResolver> {
+  fn as_byonm(&self) -> Option<&CliByonmNpmResolver> {
     match self.as_inner() {
       InnerCliNpmResolverRef::Managed(_) => None,
       InnerCliNpmResolverRef::Byonm(inner) => Some(inner),
     }
   }
 
-  fn root_node_modules_path(&self) -> Option<&PathBuf>;
+  fn root_node_modules_path(&self) -> Option<&Path>;
 
-  fn resolve_pkg_folder_from_deno_module_req(
+  fn ensure_read_permission<'a>(
     &self,
-    req: &PackageReq,
-    referrer: &ModuleSpecifier,
-  ) -> Result<PathBuf, AnyError>;
+    permissions: &mut dyn NodePermissions,
+    path: &'a Path,
+  ) -> Result<Cow<'a, Path>, AnyError>;
 
   /// Returns a hash returning the state of the npm resolver
   /// or `None` if the state currently can't be determined.
@@ -105,14 +133,19 @@ pub struct NpmFetchResolver {
   nv_by_req: DashMap<PackageReq, Option<PackageNv>>,
   info_by_name: DashMap<String, Option<Arc<NpmPackageInfo>>>,
   file_fetcher: Arc<FileFetcher>,
+  npmrc: Arc<ResolvedNpmRc>,
 }
 
 impl NpmFetchResolver {
-  pub fn new(file_fetcher: Arc<FileFetcher>) -> Self {
+  pub fn new(
+    file_fetcher: Arc<FileFetcher>,
+    npmrc: Arc<ResolvedNpmRc>,
+  ) -> Self {
     Self {
       nv_by_req: Default::default(),
       info_by_name: Default::default(),
       file_fetcher,
+      npmrc,
     }
   }
 
@@ -147,11 +180,21 @@ impl NpmFetchResolver {
       return info.value().clone();
     }
     let fetch_package_info = || async {
-      let info_url = npm_registry_url().join(name).ok()?;
+      let info_url = get_package_url(&self.npmrc, name);
       let file_fetcher = self.file_fetcher.clone();
+      let registry_config = self.npmrc.get_registry_config(name);
+      // TODO(bartlomieju): this should error out, not use `.ok()`.
+      let maybe_auth_header =
+        maybe_auth_header_for_npm_registry(registry_config).ok()?;
       // spawn due to the lsp's `Send` requirement
       let file = deno_core::unsync::spawn(async move {
-        file_fetcher.fetch_bypass_permissions(&info_url).await.ok()
+        file_fetcher
+          .fetch_bypass_permissions_with_maybe_auth(
+            &info_url,
+            maybe_auth_header,
+          )
+          .await
+          .ok()
       })
       .await
       .ok()??;
@@ -162,3 +205,15 @@ impl NpmFetchResolver {
     info
   }
 }
+
+pub const NPM_CONFIG_USER_AGENT_ENV_VAR: &str = "npm_config_user_agent";
+
+pub fn get_npm_config_user_agent() -> String {
+  format!(
+    "deno/{} npm/? deno/{} {} {}",
+    env!("CARGO_PKG_VERSION"),
+    env!("CARGO_PKG_VERSION"),
+    std::env::consts::OS,
+    std::env::consts::ARCH
+  )
+}
diff --git a/cli/ops/bench.rs b/cli/ops/bench.rs
index edd8c118ca..1f4a4bd9b5 100644
--- a/cli/ops/bench.rs
+++ b/cli/ops/bench.rs
@@ -2,8 +2,6 @@
 
 use std::sync::atomic::AtomicUsize;
 use std::sync::atomic::Ordering;
-use std::sync::Arc;
-use std::time;
 
 use deno_core::error::generic_error;
 use deno_core::error::type_error;
@@ -12,10 +10,9 @@ use deno_core::op2;
 use deno_core::v8;
 use deno_core::ModuleSpecifier;
 use deno_core::OpState;
-use deno_runtime::deno_permissions::create_child_permissions;
 use deno_runtime::deno_permissions::ChildPermissionsArg;
-use deno_runtime::deno_permissions::PermissionDescriptorParser;
 use deno_runtime::deno_permissions::PermissionsContainer;
+use deno_runtime::deno_web::StartTime;
 use tokio::sync::mpsc::UnboundedSender;
 use uuid::Uuid;
 
@@ -59,21 +56,10 @@ struct PermissionsHolder(Uuid, PermissionsContainer);
 pub fn op_pledge_test_permissions(
   state: &mut OpState,
   #[serde] args: ChildPermissionsArg,
-) -> Result<Uuid, AnyError> {
+) -> Result<Uuid, deno_runtime::deno_permissions::ChildPermissionError> {
   let token = Uuid::new_v4();
-  let permission_desc_parser = state
-    .borrow::<Arc<dyn PermissionDescriptorParser>>()
-    .clone();
   let parent_permissions = state.borrow_mut::<PermissionsContainer>();
-  let worker_permissions = {
-    let mut parent_permissions = parent_permissions.inner.lock();
-    let perms = create_child_permissions(
-      permission_desc_parser.as_ref(),
-      &mut parent_permissions,
-      args,
-    )?;
-    PermissionsContainer::new(permission_desc_parser, perms)
-  };
+  let worker_permissions = parent_permissions.create_child_permissions(args)?;
   let parent_permissions = parent_permissions.clone();
 
   if state.try_take::<PermissionsHolder>().is_some() {
@@ -83,7 +69,6 @@ pub fn op_pledge_test_permissions(
   state.put::<PermissionsHolder>(PermissionsHolder(token, parent_permissions));
 
   // NOTE: This call overrides current permission set for the worker
-  state.put(worker_permissions.inner.clone());
   state.put::<PermissionsContainer>(worker_permissions);
 
   Ok(token)
@@ -100,7 +85,6 @@ pub fn op_restore_test_permissions(
     }
 
     let permissions = permissions_holder.1;
-    state.put(permissions.inner.clone());
     state.put::<PermissionsContainer>(permissions);
     Ok(())
   } else {
@@ -163,8 +147,8 @@ fn op_dispatch_bench_event(state: &mut OpState, #[serde] event: BenchEvent) {
 
 #[op2(fast)]
 #[number]
-fn op_bench_now(state: &mut OpState) -> Result<u64, AnyError> {
-  let ns = state.borrow::<time::Instant>().elapsed().as_nanos();
+fn op_bench_now(state: &mut OpState) -> Result<u64, std::num::TryFromIntError> {
+  let ns = state.borrow::<StartTime>().elapsed().as_nanos();
   let ns_u64 = u64::try_from(ns)?;
   Ok(ns_u64)
 }
diff --git a/cli/ops/jupyter.rs b/cli/ops/jupyter.rs
index f7f006d9bd..5bdf97e60f 100644
--- a/cli/ops/jupyter.rs
+++ b/cli/ops/jupyter.rs
@@ -46,7 +46,7 @@ pub fn op_jupyter_input(
   state: &mut OpState,
   #[string] prompt: String,
   is_password: bool,
-) -> Result<Option<String>, AnyError> {
+) -> Option<String> {
   let (last_execution_request, stdin_connection_proxy) = {
     (
       state.borrow::<Arc<Mutex<Option<JupyterMessage>>>>().clone(),
@@ -58,11 +58,11 @@ pub fn op_jupyter_input(
   if let Some(last_request) = maybe_last_request {
     let JupyterMessageContent::ExecuteRequest(msg) = &last_request.content
     else {
-      return Ok(None);
+      return None;
     };
 
     if !msg.allow_stdin {
-      return Ok(None);
+      return None;
     }
 
     let content = InputRequest {
@@ -73,7 +73,7 @@ pub fn op_jupyter_input(
     let msg = JupyterMessage::new(content, Some(&last_request));
 
     let Ok(()) = stdin_connection_proxy.lock().tx.send(msg) else {
-      return Ok(None);
+      return None;
     };
 
     // Need to spawn a separate thread here, because `blocking_recv()` can't
@@ -82,17 +82,25 @@ pub fn op_jupyter_input(
       stdin_connection_proxy.lock().rx.blocking_recv()
     });
     let Ok(Some(response)) = join_handle.join() else {
-      return Ok(None);
+      return None;
     };
 
     let JupyterMessageContent::InputReply(msg) = response.content else {
-      return Ok(None);
+      return None;
     };
 
-    return Ok(Some(msg.value));
+    return Some(msg.value);
   }
 
-  Ok(None)
+  None
+}
+
+#[derive(Debug, thiserror::Error)]
+pub enum JupyterBroadcastError {
+  #[error(transparent)]
+  SerdeJson(serde_json::Error),
+  #[error(transparent)]
+  ZeroMq(AnyError),
 }
 
 #[op2(async)]
@@ -102,7 +110,7 @@ pub async fn op_jupyter_broadcast(
   #[serde] content: serde_json::Value,
   #[serde] metadata: serde_json::Value,
   #[serde] buffers: Vec<deno_core::JsBuffer>,
-) -> Result<(), AnyError> {
+) -> Result<(), JupyterBroadcastError> {
   let (iopub_connection, last_execution_request) = {
     let s = state.borrow();
 
@@ -125,36 +133,35 @@ pub async fn op_jupyter_broadcast(
           content,
           err
       );
-      err
+      JupyterBroadcastError::SerdeJson(err)
     })?;
 
     let jupyter_message = JupyterMessage::new(content, Some(&last_request))
       .with_metadata(metadata)
       .with_buffers(buffers.into_iter().map(|b| b.to_vec().into()).collect());
 
-    iopub_connection.lock().send(jupyter_message).await?;
+    iopub_connection
+      .lock()
+      .send(jupyter_message)
+      .await
+      .map_err(JupyterBroadcastError::ZeroMq)?;
   }
 
   Ok(())
 }
 
 #[op2(fast)]
-pub fn op_print(
-  state: &mut OpState,
-  #[string] msg: &str,
-  is_err: bool,
-) -> Result<(), AnyError> {
+pub fn op_print(state: &mut OpState, #[string] msg: &str, is_err: bool) {
   let sender = state.borrow_mut::<mpsc::UnboundedSender<StreamContent>>();
 
   if is_err {
     if let Err(err) = sender.send(StreamContent::stderr(msg)) {
       log::error!("Failed to send stderr message: {}", err);
     }
-    return Ok(());
+    return;
   }
 
   if let Err(err) = sender.send(StreamContent::stdout(msg)) {
     log::error!("Failed to send stdout message: {}", err);
   }
-  Ok(())
 }
diff --git a/cli/ops/testing.rs b/cli/ops/testing.rs
index 6a8d310062..00aafb8286 100644
--- a/cli/ops/testing.rs
+++ b/cli/ops/testing.rs
@@ -16,13 +16,10 @@ use deno_core::op2;
 use deno_core::v8;
 use deno_core::ModuleSpecifier;
 use deno_core::OpState;
-use deno_runtime::deno_permissions::create_child_permissions;
 use deno_runtime::deno_permissions::ChildPermissionsArg;
-use deno_runtime::deno_permissions::PermissionDescriptorParser;
 use deno_runtime::deno_permissions::PermissionsContainer;
 use std::sync::atomic::AtomicUsize;
 use std::sync::atomic::Ordering;
-use std::sync::Arc;
 use uuid::Uuid;
 
 deno_core::extension!(deno_test,
@@ -54,21 +51,10 @@ struct PermissionsHolder(Uuid, PermissionsContainer);
 pub fn op_pledge_test_permissions(
   state: &mut OpState,
   #[serde] args: ChildPermissionsArg,
-) -> Result<Uuid, AnyError> {
+) -> Result<Uuid, deno_runtime::deno_permissions::ChildPermissionError> {
   let token = Uuid::new_v4();
-  let permission_desc_parser = state
-    .borrow::<Arc<dyn PermissionDescriptorParser>>()
-    .clone();
   let parent_permissions = state.borrow_mut::<PermissionsContainer>();
-  let worker_permissions = {
-    let mut parent_permissions = parent_permissions.inner.lock();
-    let perms = create_child_permissions(
-      permission_desc_parser.as_ref(),
-      &mut parent_permissions,
-      args,
-    )?;
-    PermissionsContainer::new(permission_desc_parser, perms)
-  };
+  let worker_permissions = parent_permissions.create_child_permissions(args)?;
   let parent_permissions = parent_permissions.clone();
 
   if state.try_take::<PermissionsHolder>().is_some() {
@@ -77,7 +63,6 @@ pub fn op_pledge_test_permissions(
   state.put::<PermissionsHolder>(PermissionsHolder(token, parent_permissions));
 
   // NOTE: This call overrides current permission set for the worker
-  state.put(worker_permissions.inner.clone());
   state.put::<PermissionsContainer>(worker_permissions);
 
   Ok(token)
@@ -94,7 +79,6 @@ pub fn op_restore_test_permissions(
     }
 
     let permissions = permissions_holder.1;
-    state.put(permissions.inner.clone());
     state.put::<PermissionsContainer>(permissions);
     Ok(())
   } else {
@@ -166,7 +150,7 @@ fn op_register_test_step(
   #[smi] parent_id: usize,
   #[smi] root_id: usize,
   #[string] root_name: String,
-) -> Result<usize, AnyError> {
+) -> usize {
   let id = NEXT_ID.fetch_add(1, Ordering::SeqCst);
   let origin = state.borrow::<ModuleSpecifier>().to_string();
   let description = TestStepDescription {
@@ -185,7 +169,7 @@ fn op_register_test_step(
   };
   let sender = state.borrow_mut::<TestEventSender>();
   sender.send(TestEvent::StepRegister(description)).ok();
-  Ok(id)
+  id
 }
 
 #[op2(fast)]
diff --git a/cli/resolver.rs b/cli/resolver.rs
index 07cb6931df..a2dd47430f 100644
--- a/cli/resolver.rs
+++ b/cli/resolver.rs
@@ -4,55 +4,55 @@ use async_trait::async_trait;
 use dashmap::DashMap;
 use dashmap::DashSet;
 use deno_ast::MediaType;
-use deno_config::workspace::MappedResolution;
 use deno_config::workspace::MappedResolutionDiagnostic;
 use deno_config::workspace::MappedResolutionError;
-use deno_config::workspace::WorkspaceResolver;
 use deno_core::anyhow::anyhow;
 use deno_core::anyhow::Context;
 use deno_core::error::AnyError;
+use deno_core::url::Url;
 use deno_core::ModuleSourceCode;
 use deno_core::ModuleSpecifier;
 use deno_graph::source::ResolutionMode;
 use deno_graph::source::ResolveError;
-use deno_graph::source::Resolver;
 use deno_graph::source::UnknownBuiltInNodeModuleError;
-use deno_graph::source::DEFAULT_JSX_IMPORT_SOURCE_MODULE;
 use deno_graph::NpmLoadError;
 use deno_graph::NpmResolvePkgReqsResult;
 use deno_npm::resolution::NpmResolutionError;
-use deno_package_json::PackageJsonDepValue;
+use deno_resolver::sloppy_imports::SloppyImportsResolver;
 use deno_runtime::colors;
 use deno_runtime::deno_fs;
 use deno_runtime::deno_fs::FileSystem;
 use deno_runtime::deno_node::is_builtin_node_module;
-use deno_runtime::deno_node::NodeResolver;
-use deno_runtime::fs_util::specifier_to_file_path;
-use deno_semver::npm::NpmPackageReqReference;
+use deno_runtime::deno_node::DenoFsNodeResolverEnv;
 use deno_semver::package::PackageReq;
-use node_resolver::errors::ClosestPkgJsonError;
-use node_resolver::errors::NodeResolveError;
-use node_resolver::errors::NodeResolveErrorKind;
-use node_resolver::errors::PackageFolderResolveErrorKind;
-use node_resolver::errors::PackageFolderResolveIoError;
-use node_resolver::errors::PackageNotFoundError;
-use node_resolver::errors::PackageResolveErrorKind;
-use node_resolver::errors::UrlToNodeResolutionError;
 use node_resolver::NodeModuleKind;
-use node_resolver::NodeResolution;
 use node_resolver::NodeResolutionMode;
-use node_resolver::PackageJson;
 use std::borrow::Cow;
 use std::path::Path;
 use std::path::PathBuf;
 use std::sync::Arc;
+use thiserror::Error;
 
-use crate::args::JsxImportSourceConfig;
 use crate::args::DENO_DISABLE_PEDANTIC_NODE_WARNINGS;
 use crate::node::CliNodeCodeTranslator;
 use crate::npm::CliNpmResolver;
 use crate::npm::InnerCliNpmResolverRef;
 use crate::util::sync::AtomicFlag;
+use crate::util::text_encoding::from_utf8_lossy_owned;
+
+pub type CjsTracker = deno_resolver::cjs::CjsTracker<DenoFsNodeResolverEnv>;
+pub type IsCjsResolver =
+  deno_resolver::cjs::IsCjsResolver<DenoFsNodeResolverEnv>;
+pub type IsCjsResolverOptions = deno_resolver::cjs::IsCjsResolverOptions;
+pub type CliSloppyImportsResolver =
+  SloppyImportsResolver<SloppyImportsCachedFs>;
+pub type CliDenoResolver = deno_resolver::DenoResolver<
+  CliDenoResolverFs,
+  DenoFsNodeResolverEnv,
+  SloppyImportsCachedFs,
+>;
+pub type CliNpmReqResolver =
+  deno_resolver::npm::NpmReqResolver<CliDenoResolverFs, DenoFsNodeResolverEnv>;
 
 pub struct ModuleCodeStringSource {
   pub code: ModuleSourceCode,
@@ -60,279 +60,75 @@ pub struct ModuleCodeStringSource {
   pub media_type: MediaType,
 }
 
-#[derive(Debug)]
-pub struct CliNodeResolver {
-  cjs_resolutions: Arc<CjsResolutionStore>,
-  fs: Arc<dyn deno_fs::FileSystem>,
-  node_resolver: Arc<NodeResolver>,
-  // todo(dsherret): remove this pub(crate)
-  pub(crate) npm_resolver: Arc<dyn CliNpmResolver>,
-}
+#[derive(Debug, Clone)]
+pub struct CliDenoResolverFs(pub Arc<dyn FileSystem>);
 
-impl CliNodeResolver {
-  pub fn new(
-    cjs_resolutions: Arc<CjsResolutionStore>,
-    fs: Arc<dyn deno_fs::FileSystem>,
-    node_resolver: Arc<NodeResolver>,
-    npm_resolver: Arc<dyn CliNpmResolver>,
-  ) -> Self {
-    Self {
-      cjs_resolutions,
-      fs,
-      node_resolver,
-      npm_resolver,
-    }
+impl deno_resolver::fs::DenoResolverFs for CliDenoResolverFs {
+  fn read_to_string_lossy(&self, path: &Path) -> std::io::Result<String> {
+    self
+      .0
+      .read_text_file_lossy_sync(path, None)
+      .map_err(|e| e.into_io_error())
   }
 
-  pub fn in_npm_package(&self, specifier: &ModuleSpecifier) -> bool {
-    self.npm_resolver.in_npm_package(specifier)
+  fn realpath_sync(&self, path: &Path) -> std::io::Result<PathBuf> {
+    self.0.realpath_sync(path).map_err(|e| e.into_io_error())
   }
 
-  pub fn get_closest_package_json(
+  fn exists_sync(&self, path: &Path) -> bool {
+    self.0.exists_sync(path)
+  }
+
+  fn is_dir_sync(&self, path: &Path) -> bool {
+    self.0.is_dir_sync(path)
+  }
+
+  fn read_dir_sync(
     &self,
-    referrer: &ModuleSpecifier,
-  ) -> Result<Option<Arc<PackageJson>>, ClosestPkgJsonError> {
-    self.node_resolver.get_closest_package_json(referrer)
-  }
-
-  pub fn resolve_if_for_npm_pkg(
-    &self,
-    specifier: &str,
-    referrer: &ModuleSpecifier,
-    mode: NodeResolutionMode,
-  ) -> Result<Option<NodeResolution>, AnyError> {
-    let resolution_result = self.resolve(specifier, referrer, mode);
-    match resolution_result {
-      Ok(res) => Ok(Some(res)),
-      Err(err) => {
-        let err = err.into_kind();
-        match err {
-          NodeResolveErrorKind::RelativeJoin(_)
-          | NodeResolveErrorKind::PackageImportsResolve(_)
-          | NodeResolveErrorKind::UnsupportedEsmUrlScheme(_)
-          | NodeResolveErrorKind::DataUrlReferrer(_)
-          | NodeResolveErrorKind::TypesNotFound(_)
-          | NodeResolveErrorKind::FinalizeResolution(_)
-          | NodeResolveErrorKind::UrlToNodeResolution(_) => Err(err.into()),
-          NodeResolveErrorKind::PackageResolve(err) => {
-            let err = err.into_kind();
-            match err {
-              PackageResolveErrorKind::ClosestPkgJson(_)
-              | PackageResolveErrorKind::InvalidModuleSpecifier(_)
-              | PackageResolveErrorKind::ExportsResolve(_)
-              | PackageResolveErrorKind::SubpathResolve(_) => Err(err.into()),
-              PackageResolveErrorKind::PackageFolderResolve(err) => {
-                match err.as_kind() {
-                  PackageFolderResolveErrorKind::Io(
-                    PackageFolderResolveIoError { package_name, .. },
-                  )
-                  | PackageFolderResolveErrorKind::PackageNotFound(
-                    PackageNotFoundError { package_name, .. },
-                  ) => {
-                    if self.in_npm_package(referrer) {
-                      return Err(err.into());
-                    }
-                    if let Some(byonm_npm_resolver) =
-                      self.npm_resolver.as_byonm()
-                    {
-                      if byonm_npm_resolver
-                        .find_ancestor_package_json_with_dep(
-                          package_name,
-                          referrer,
-                        )
-                        .is_some()
-                      {
-                        return Err(anyhow!(
-                        concat!(
-                        "Could not resolve \"{}\", but found it in a package.json. ",
-                        "Deno expects the node_modules/ directory to be up to date. ",
-                        "Did you forget to run `deno install`?"
-                      ),
-                        specifier
-                      ));
-                      }
-                    }
-                    Ok(None)
-                  }
-                  PackageFolderResolveErrorKind::ReferrerNotFound(_) => {
-                    if self.in_npm_package(referrer) {
-                      return Err(err.into());
-                    }
-                    Ok(None)
-                  }
-                }
-              }
-            }
-          }
-        }
-      }
-    }
-  }
-
-  pub fn resolve(
-    &self,
-    specifier: &str,
-    referrer: &ModuleSpecifier,
-    mode: NodeResolutionMode,
-  ) -> Result<NodeResolution, NodeResolveError> {
-    let referrer_kind = if self.cjs_resolutions.contains(referrer) {
-      NodeModuleKind::Cjs
-    } else {
-      NodeModuleKind::Esm
-    };
-
-    let res =
-      self
-        .node_resolver
-        .resolve(specifier, referrer, referrer_kind, mode)?;
-    Ok(self.handle_node_resolution(res))
-  }
-
-  pub fn resolve_req_reference(
-    &self,
-    req_ref: &NpmPackageReqReference,
-    referrer: &ModuleSpecifier,
-    mode: NodeResolutionMode,
-  ) -> Result<NodeResolution, AnyError> {
-    self.resolve_req_with_sub_path(
-      req_ref.req(),
-      req_ref.sub_path(),
-      referrer,
-      mode,
-    )
-  }
-
-  pub fn resolve_req_with_sub_path(
-    &self,
-    req: &PackageReq,
-    sub_path: Option<&str>,
-    referrer: &ModuleSpecifier,
-    mode: NodeResolutionMode,
-  ) -> Result<NodeResolution, AnyError> {
-    let package_folder = self
-      .npm_resolver
-      .resolve_pkg_folder_from_deno_module_req(req, referrer)?;
-    let resolution_result = self.resolve_package_sub_path_from_deno_module(
-      &package_folder,
-      sub_path,
-      Some(referrer),
-      mode,
-    );
-    match resolution_result {
-      Ok(resolution) => Ok(resolution),
-      Err(err) => {
-        if self.npm_resolver.as_byonm().is_some() {
-          let package_json_path = package_folder.join("package.json");
-          if !self.fs.exists_sync(&package_json_path) {
-            return Err(anyhow!(
-              "Could not find '{}'. Deno expects the node_modules/ directory to be up to date. Did you forget to run `deno install`?",
-              package_json_path.display(),
-            ));
-          }
-        }
-        Err(err)
-      }
-    }
-  }
-
-  pub fn resolve_package_sub_path_from_deno_module(
-    &self,
-    package_folder: &Path,
-    sub_path: Option<&str>,
-    maybe_referrer: Option<&ModuleSpecifier>,
-    mode: NodeResolutionMode,
-  ) -> Result<NodeResolution, AnyError> {
-    let res = self
-      .node_resolver
-      .resolve_package_subpath_from_deno_module(
-        package_folder,
-        sub_path,
-        maybe_referrer,
-        mode,
-      )?;
-    Ok(self.handle_node_resolution(res))
-  }
-
-  pub fn handle_if_in_node_modules(
-    &self,
-    specifier: &ModuleSpecifier,
-  ) -> Result<Option<ModuleSpecifier>, AnyError> {
-    // skip canonicalizing if we definitely know it's unnecessary
-    if specifier.scheme() == "file"
-      && specifier.path().contains("/node_modules/")
-    {
-      // Specifiers in the node_modules directory are canonicalized
-      // so canoncalize then check if it's in the node_modules directory.
-      // If so, check if we need to store this specifier as being a CJS
-      // resolution.
-      let specifier =
-        crate::node::resolve_specifier_into_node_modules(specifier);
-      if self.in_npm_package(&specifier) {
-        let resolution =
-          self.node_resolver.url_to_node_resolution(specifier)?;
-        if let NodeResolution::CommonJs(specifier) = &resolution {
-          self.cjs_resolutions.insert(specifier.clone());
-        }
-        return Ok(Some(resolution.into_url()));
-      }
-    }
-
-    Ok(None)
-  }
-
-  pub fn url_to_node_resolution(
-    &self,
-    specifier: ModuleSpecifier,
-  ) -> Result<NodeResolution, UrlToNodeResolutionError> {
-    self.node_resolver.url_to_node_resolution(specifier)
-  }
-
-  fn handle_node_resolution(
-    &self,
-    resolution: NodeResolution,
-  ) -> NodeResolution {
-    if let NodeResolution::CommonJs(specifier) = &resolution {
-      // remember that this was a common js resolution
-      self.cjs_resolutions.insert(specifier.clone());
-    }
-    resolution
+    dir_path: &Path,
+  ) -> std::io::Result<Vec<deno_resolver::fs::DirEntry>> {
+    self
+      .0
+      .read_dir_sync(dir_path)
+      .map(|entries| {
+        entries
+          .into_iter()
+          .map(|e| deno_resolver::fs::DirEntry {
+            name: e.name,
+            is_file: e.is_file,
+            is_directory: e.is_directory,
+          })
+          .collect::<Vec<_>>()
+      })
+      .map_err(|err| err.into_io_error())
   }
 }
 
+#[derive(Debug, Error)]
+#[error("{media_type} files are not supported in npm packages: {specifier}")]
+pub struct NotSupportedKindInNpmError {
+  pub media_type: MediaType,
+  pub specifier: Url,
+}
+
+// todo(dsherret): move to module_loader.rs (it seems to be here due to use in standalone)
 #[derive(Clone)]
 pub struct NpmModuleLoader {
-  cjs_resolutions: Arc<CjsResolutionStore>,
-  node_code_translator: Arc<CliNodeCodeTranslator>,
+  cjs_tracker: Arc<CjsTracker>,
   fs: Arc<dyn deno_fs::FileSystem>,
-  node_resolver: Arc<CliNodeResolver>,
+  node_code_translator: Arc<CliNodeCodeTranslator>,
 }
 
 impl NpmModuleLoader {
   pub fn new(
-    cjs_resolutions: Arc<CjsResolutionStore>,
-    node_code_translator: Arc<CliNodeCodeTranslator>,
+    cjs_tracker: Arc<CjsTracker>,
     fs: Arc<dyn deno_fs::FileSystem>,
-    node_resolver: Arc<CliNodeResolver>,
+    node_code_translator: Arc<CliNodeCodeTranslator>,
   ) -> Self {
     Self {
-      cjs_resolutions,
+      cjs_tracker,
       node_code_translator,
       fs,
-      node_resolver,
-    }
-  }
-
-  pub async fn load_if_in_npm_package(
-    &self,
-    specifier: &ModuleSpecifier,
-    maybe_referrer: Option<&ModuleSpecifier>,
-  ) -> Option<Result<ModuleCodeStringSource, AnyError>> {
-    if self.node_resolver.in_npm_package(specifier)
-      || (specifier.scheme() == "file" && specifier.path().ends_with(".cjs"))
-    {
-      Some(self.load(specifier, maybe_referrer).await)
-    } else {
-      None
     }
   }
 
@@ -378,27 +174,30 @@ impl NpmModuleLoader {
         }
       })?;
 
-    let code = if self.cjs_resolutions.contains(specifier)
-      || (specifier.scheme() == "file" && specifier.path().ends_with(".cjs"))
-    {
+    let media_type = MediaType::from_specifier(specifier);
+    if media_type.is_emittable() {
+      return Err(AnyError::from(NotSupportedKindInNpmError {
+        media_type,
+        specifier: specifier.clone(),
+      }));
+    }
+
+    let code = if self.cjs_tracker.is_maybe_cjs(specifier, media_type)? {
       // translate cjs to esm if it's cjs and inject node globals
-      let code = match String::from_utf8_lossy(&code) {
-        Cow::Owned(code) => code,
-        // SAFETY: `String::from_utf8_lossy` guarantees that the result is valid
-        // UTF-8 if `Cow::Borrowed` is returned.
-        Cow::Borrowed(_) => unsafe { String::from_utf8_unchecked(code) },
-      };
+      let code = from_utf8_lossy_owned(code);
       ModuleSourceCode::String(
         self
           .node_code_translator
-          .translate_cjs_to_esm(specifier, Some(code))
+          .translate_cjs_to_esm(specifier, Some(Cow::Owned(code)))
           .await?
+          .into_owned()
           .into(),
       )
     } else {
       // esm and json code is untouched
       ModuleSourceCode::Bytes(code.into_boxed_slice().into())
     };
+
     Ok(ModuleCodeStringSource {
       code,
       found_url: specifier.clone(),
@@ -407,78 +206,36 @@ impl NpmModuleLoader {
   }
 }
 
-/// Keeps track of what module specifiers were resolved as CJS.
-#[derive(Debug, Default)]
-pub struct CjsResolutionStore(DashSet<ModuleSpecifier>);
-
-impl CjsResolutionStore {
-  pub fn contains(&self, specifier: &ModuleSpecifier) -> bool {
-    self.0.contains(specifier)
-  }
-
-  pub fn insert(&self, specifier: ModuleSpecifier) {
-    self.0.insert(specifier);
-  }
+pub struct CliResolverOptions {
+  pub deno_resolver: Arc<CliDenoResolver>,
+  pub npm_resolver: Option<Arc<dyn CliNpmResolver>>,
+  pub bare_node_builtins_enabled: bool,
 }
 
 /// A resolver that takes care of resolution, taking into account loaded
 /// import map, JSX settings.
 #[derive(Debug)]
-pub struct CliGraphResolver {
-  node_resolver: Option<Arc<CliNodeResolver>>,
+pub struct CliResolver {
+  deno_resolver: Arc<CliDenoResolver>,
   npm_resolver: Option<Arc<dyn CliNpmResolver>>,
-  sloppy_imports_resolver: Option<Arc<SloppyImportsResolver>>,
-  workspace_resolver: Arc<WorkspaceResolver>,
-  maybe_default_jsx_import_source: Option<String>,
-  maybe_default_jsx_import_source_types: Option<String>,
-  maybe_jsx_import_source_module: Option<String>,
-  maybe_vendor_specifier: Option<ModuleSpecifier>,
   found_package_json_dep_flag: AtomicFlag,
   bare_node_builtins_enabled: bool,
   warned_pkgs: DashSet<PackageReq>,
 }
 
-pub struct CliGraphResolverOptions<'a> {
-  pub node_resolver: Option<Arc<CliNodeResolver>>,
-  pub npm_resolver: Option<Arc<dyn CliNpmResolver>>,
-  pub sloppy_imports_resolver: Option<Arc<SloppyImportsResolver>>,
-  pub workspace_resolver: Arc<WorkspaceResolver>,
-  pub bare_node_builtins_enabled: bool,
-  pub maybe_jsx_import_source_config: Option<JsxImportSourceConfig>,
-  pub maybe_vendor_dir: Option<&'a PathBuf>,
-}
-
-impl CliGraphResolver {
-  pub fn new(options: CliGraphResolverOptions) -> Self {
+impl CliResolver {
+  pub fn new(options: CliResolverOptions) -> Self {
     Self {
-      node_resolver: options.node_resolver,
+      deno_resolver: options.deno_resolver,
       npm_resolver: options.npm_resolver,
-      sloppy_imports_resolver: options.sloppy_imports_resolver,
-      workspace_resolver: options.workspace_resolver,
-      maybe_default_jsx_import_source: options
-        .maybe_jsx_import_source_config
-        .as_ref()
-        .and_then(|c| c.default_specifier.clone()),
-      maybe_default_jsx_import_source_types: options
-        .maybe_jsx_import_source_config
-        .as_ref()
-        .and_then(|c| c.default_types_specifier.clone()),
-      maybe_jsx_import_source_module: options
-        .maybe_jsx_import_source_config
-        .map(|c| c.module),
-      maybe_vendor_specifier: options
-        .maybe_vendor_dir
-        .and_then(|v| ModuleSpecifier::from_directory_path(v).ok()),
       found_package_json_dep_flag: Default::default(),
       bare_node_builtins_enabled: options.bare_node_builtins_enabled,
       warned_pkgs: Default::default(),
     }
   }
 
-  pub fn as_graph_resolver(&self) -> &dyn Resolver {
-    self
-  }
-
+  // todo(dsherret): move this off CliResolver as CliResolver is acting
+  // like a factory by doing this (it's beyond its responsibility)
   pub fn create_graph_npm_resolver(&self) -> WorkerCliNpmGraphResolver {
     WorkerCliNpmGraphResolver {
       npm_resolver: self.npm_resolver.as_ref(),
@@ -486,28 +243,12 @@ impl CliGraphResolver {
       bare_node_builtins_enabled: self.bare_node_builtins_enabled,
     }
   }
-}
 
-impl Resolver for CliGraphResolver {
-  fn default_jsx_import_source(&self) -> Option<String> {
-    self.maybe_default_jsx_import_source.clone()
-  }
-
-  fn default_jsx_import_source_types(&self) -> Option<String> {
-    self.maybe_default_jsx_import_source_types.clone()
-  }
-
-  fn jsx_import_source_module(&self) -> &str {
-    self
-      .maybe_jsx_import_source_module
-      .as_deref()
-      .unwrap_or(DEFAULT_JSX_IMPORT_SOURCE_MODULE)
-  }
-
-  fn resolve(
+  pub fn resolve(
     &self,
     raw_specifier: &str,
     referrer_range: &deno_graph::Range,
+    referrer_kind: NodeModuleKind,
     mode: ResolutionMode,
   ) -> Result<ModuleSpecifier, ResolveError> {
     fn to_node_mode(mode: ResolutionMode) -> NodeResolutionMode {
@@ -517,210 +258,50 @@ impl Resolver for CliGraphResolver {
       }
     }
 
-    let referrer = &referrer_range.specifier;
+    let resolution = self
+      .deno_resolver
+      .resolve(
+        raw_specifier,
+        &referrer_range.specifier,
+        referrer_kind,
+        to_node_mode(mode),
+      )
+      .map_err(|err| match err.into_kind() {
+        deno_resolver::DenoResolveErrorKind::MappedResolution(
+          mapped_resolution_error,
+        ) => match mapped_resolution_error {
+          MappedResolutionError::Specifier(e) => ResolveError::Specifier(e),
+          // deno_graph checks specifically for an ImportMapError
+          MappedResolutionError::ImportMap(e) => ResolveError::Other(e.into()),
+          err => ResolveError::Other(err.into()),
+        },
+        err => ResolveError::Other(err.into()),
+      })?;
 
-    // Use node resolution if we're in an npm package
-    if let Some(node_resolver) = self.node_resolver.as_ref() {
-      if referrer.scheme() == "file" && node_resolver.in_npm_package(referrer) {
-        return node_resolver
-          .resolve(raw_specifier, referrer, to_node_mode(mode))
-          .map(|res| res.into_url())
-          .map_err(|e| ResolveError::Other(e.into()));
-      }
+    if resolution.found_package_json_dep {
+      // mark that we need to do an "npm install" later
+      self.found_package_json_dep_flag.raise();
     }
 
-    // Attempt to resolve with the workspace resolver
-    let result: Result<_, ResolveError> = self
-      .workspace_resolver
-      .resolve(raw_specifier, referrer)
-      .map_err(|err| match err {
-        MappedResolutionError::Specifier(err) => ResolveError::Specifier(err),
-        MappedResolutionError::ImportMap(err) => {
-          ResolveError::Other(err.into())
-        }
-        MappedResolutionError::Workspace(err) => {
-          ResolveError::Other(err.into())
-        }
-      });
-    let result = match result {
-      Ok(resolution) => match resolution {
-        MappedResolution::Normal {
-          specifier,
-          maybe_diagnostic,
-        }
-        | MappedResolution::ImportMap {
-          specifier,
-          maybe_diagnostic,
-        } => {
-          if let Some(diagnostic) = maybe_diagnostic {
-            match &*diagnostic {
-              MappedResolutionDiagnostic::ConstraintNotMatchedLocalVersion { reference, .. } => {
-                if self.warned_pkgs.insert(reference.req().clone()) {
-                  log::warn!("{} {}\n    at {}", colors::yellow("Warning"), diagnostic, referrer_range);
-                }
-              }
-            }
-          }
-          // do sloppy imports resolution if enabled
-          if let Some(sloppy_imports_resolver) = &self.sloppy_imports_resolver {
-            Ok(
-              sloppy_imports_resolver
-                .resolve(&specifier, mode)
-                .map(|s| s.into_specifier())
-                .unwrap_or(specifier),
-            )
-          } else {
-            Ok(specifier)
-          }
-        }
-        MappedResolution::WorkspaceJsrPackage { specifier, .. } => {
-          Ok(specifier)
-        }
-        MappedResolution::WorkspaceNpmPackage {
-          target_pkg_json: pkg_json,
-          sub_path,
-          ..
-        } => self
-          .node_resolver
-          .as_ref()
-          .unwrap()
-          .resolve_package_sub_path_from_deno_module(
-            pkg_json.dir_path(),
-            sub_path.as_deref(),
-            Some(referrer),
-            to_node_mode(mode),
-          )
-          .map_err(ResolveError::Other)
-          .map(|res| res.into_url()),
-        MappedResolution::PackageJson {
-          dep_result,
-          alias,
-          sub_path,
+    if let Some(diagnostic) = resolution.maybe_diagnostic {
+      match &*diagnostic {
+        MappedResolutionDiagnostic::ConstraintNotMatchedLocalVersion {
+          reference,
           ..
         } => {
-          // found a specifier in the package.json, so mark that
-          // we need to do an "npm install" later
-          self.found_package_json_dep_flag.raise();
-
-          dep_result
-            .as_ref()
-            .map_err(|e| ResolveError::Other(e.clone().into()))
-            .and_then(|dep| match dep {
-              PackageJsonDepValue::Req(req) => {
-                ModuleSpecifier::parse(&format!(
-                  "npm:{}{}",
-                  req,
-                  sub_path.map(|s| format!("/{}", s)).unwrap_or_default()
-                ))
-                .map_err(|e| ResolveError::Other(e.into()))
-              }
-              PackageJsonDepValue::Workspace(version_req) => self
-                .workspace_resolver
-                .resolve_workspace_pkg_json_folder_for_pkg_json_dep(
-                  alias,
-                  version_req,
-                )
-                .map_err(|e| ResolveError::Other(e.into()))
-                .and_then(|pkg_folder| {
-                  Ok(
-                    self
-                      .node_resolver
-                      .as_ref()
-                      .unwrap()
-                      .resolve_package_sub_path_from_deno_module(
-                        pkg_folder,
-                        sub_path.as_deref(),
-                        Some(referrer),
-                        to_node_mode(mode),
-                      )?
-                      .into_url(),
-                  )
-                }),
-            })
-        }
-      },
-      Err(err) => Err(err),
-    };
-
-    // When the user is vendoring, don't allow them to import directly from the vendor/ directory
-    // as it might cause them confusion or duplicate dependencies. Additionally, this folder has
-    // special treatment in the language server so it will definitely cause issues/confusion there
-    // if they do this.
-    if let Some(vendor_specifier) = &self.maybe_vendor_specifier {
-      if let Ok(specifier) = &result {
-        if specifier.as_str().starts_with(vendor_specifier.as_str()) {
-          return Err(ResolveError::Other(anyhow!("Importing from the vendor directory is not permitted. Use a remote specifier instead or disable vendoring.")));
-        }
-      }
-    }
-
-    let Some(node_resolver) = &self.node_resolver else {
-      return result;
-    };
-
-    let is_byonm = self
-      .npm_resolver
-      .as_ref()
-      .is_some_and(|r| r.as_byonm().is_some());
-    match result {
-      Ok(specifier) => {
-        if let Ok(npm_req_ref) =
-          NpmPackageReqReference::from_specifier(&specifier)
-        {
-          // check if the npm specifier resolves to a workspace member
-          if let Some(pkg_folder) = self
-            .workspace_resolver
-            .resolve_workspace_pkg_json_folder_for_npm_specifier(
-              npm_req_ref.req(),
-            )
-          {
-            return Ok(
-              node_resolver
-                .resolve_package_sub_path_from_deno_module(
-                  pkg_folder,
-                  npm_req_ref.sub_path(),
-                  Some(referrer),
-                  to_node_mode(mode),
-                )?
-                .into_url(),
+          if self.warned_pkgs.insert(reference.req().clone()) {
+            log::warn!(
+              "{} {}\n    at {}",
+              colors::yellow("Warning"),
+              diagnostic,
+              referrer_range
             );
           }
-
-          // do npm resolution for byonm
-          if is_byonm {
-            return node_resolver
-              .resolve_req_reference(&npm_req_ref, referrer, to_node_mode(mode))
-              .map(|res| res.into_url())
-              .map_err(|err| err.into());
-          }
         }
-
-        Ok(match node_resolver.handle_if_in_node_modules(&specifier)? {
-          Some(specifier) => specifier,
-          None => specifier,
-        })
-      }
-      Err(err) => {
-        // If byonm, check if the bare specifier resolves to an npm package
-        if is_byonm && referrer.scheme() == "file" {
-          let maybe_resolution = node_resolver
-            .resolve_if_for_npm_pkg(raw_specifier, referrer, to_node_mode(mode))
-            .map_err(ResolveError::Other)?;
-          if let Some(res) = maybe_resolution {
-            match res {
-              NodeResolution::Esm(url) | NodeResolution::CommonJs(url) => {
-                return Ok(url)
-              }
-              NodeResolution::BuiltIn(_) => {
-                // don't resolve bare specifiers for built-in modules via node resolution
-              }
-            }
-          }
-        }
-
-        Err(err)
       }
     }
+
+    Ok(resolution.url)
   }
 }
 
@@ -847,96 +428,18 @@ impl<'a> deno_graph::source::NpmResolver for WorkerCliNpmGraphResolver<'a> {
   }
 }
 
-#[derive(Debug, Clone, Copy, PartialEq, Eq)]
-pub enum SloppyImportsFsEntry {
-  File,
-  Dir,
-}
-
-impl SloppyImportsFsEntry {
-  pub fn from_fs_stat(
-    stat: &deno_runtime::deno_io::fs::FsStat,
-  ) -> Option<SloppyImportsFsEntry> {
-    if stat.is_file {
-      Some(SloppyImportsFsEntry::File)
-    } else if stat.is_directory {
-      Some(SloppyImportsFsEntry::Dir)
-    } else {
-      None
-    }
-  }
-}
-
-#[derive(Debug, Clone, PartialEq, Eq)]
-pub enum SloppyImportsResolution {
-  /// Ex. `./file.js` to `./file.ts`
-  JsToTs(ModuleSpecifier),
-  /// Ex. `./file` to `./file.ts`
-  NoExtension(ModuleSpecifier),
-  /// Ex. `./dir` to `./dir/index.ts`
-  Directory(ModuleSpecifier),
-}
-
-impl SloppyImportsResolution {
-  pub fn as_specifier(&self) -> &ModuleSpecifier {
-    match self {
-      Self::JsToTs(specifier) => specifier,
-      Self::NoExtension(specifier) => specifier,
-      Self::Directory(specifier) => specifier,
-    }
-  }
-
-  pub fn into_specifier(self) -> ModuleSpecifier {
-    match self {
-      Self::JsToTs(specifier) => specifier,
-      Self::NoExtension(specifier) => specifier,
-      Self::Directory(specifier) => specifier,
-    }
-  }
-
-  pub fn as_suggestion_message(&self) -> String {
-    format!("Maybe {}", self.as_base_message())
-  }
-
-  pub fn as_quick_fix_message(&self) -> String {
-    let message = self.as_base_message();
-    let mut chars = message.chars();
-    format!(
-      "{}{}.",
-      chars.next().unwrap().to_uppercase(),
-      chars.as_str()
-    )
-  }
-
-  fn as_base_message(&self) -> String {
-    match self {
-      SloppyImportsResolution::JsToTs(specifier) => {
-        let media_type = MediaType::from_specifier(specifier);
-        format!("change the extension to '{}'", media_type.as_ts_extension())
-      }
-      SloppyImportsResolution::NoExtension(specifier) => {
-        let media_type = MediaType::from_specifier(specifier);
-        format!("add a '{}' extension", media_type.as_ts_extension())
-      }
-      SloppyImportsResolution::Directory(specifier) => {
-        let file_name = specifier
-          .path()
-          .rsplit_once('/')
-          .map(|(_, file_name)| file_name)
-          .unwrap_or(specifier.path());
-        format!("specify path to '{}' file in directory instead", file_name)
-      }
-    }
-  }
-}
-
 #[derive(Debug)]
-pub struct SloppyImportsResolver {
-  fs: Arc<dyn FileSystem>,
-  cache: Option<DashMap<PathBuf, Option<SloppyImportsFsEntry>>>,
+pub struct SloppyImportsCachedFs {
+  fs: Arc<dyn deno_fs::FileSystem>,
+  cache: Option<
+    DashMap<
+      PathBuf,
+      Option<deno_resolver::sloppy_imports::SloppyImportsFsEntry>,
+    >,
+  >,
 }
 
-impl SloppyImportsResolver {
+impl SloppyImportsCachedFs {
   pub fn new(fs: Arc<dyn FileSystem>) -> Self {
     Self {
       fs,
@@ -947,409 +450,34 @@ impl SloppyImportsResolver {
   pub fn new_without_stat_cache(fs: Arc<dyn FileSystem>) -> Self {
     Self { fs, cache: None }
   }
+}
 
-  pub fn resolve(
+impl deno_resolver::sloppy_imports::SloppyImportResolverFs
+  for SloppyImportsCachedFs
+{
+  fn stat_sync(
     &self,
-    specifier: &ModuleSpecifier,
-    mode: ResolutionMode,
-  ) -> Option<SloppyImportsResolution> {
-    fn path_without_ext(
-      path: &Path,
-      media_type: MediaType,
-    ) -> Option<Cow<str>> {
-      let old_path_str = path.to_string_lossy();
-      match media_type {
-        MediaType::Unknown => Some(old_path_str),
-        _ => old_path_str
-          .strip_suffix(media_type.as_ts_extension())
-          .map(|s| Cow::Owned(s.to_string())),
-      }
-    }
-
-    fn media_types_to_paths(
-      path_no_ext: &str,
-      original_media_type: MediaType,
-      probe_media_type_types: Vec<MediaType>,
-      reason: SloppyImportsResolutionReason,
-    ) -> Vec<(PathBuf, SloppyImportsResolutionReason)> {
-      probe_media_type_types
-        .into_iter()
-        .filter(|media_type| *media_type != original_media_type)
-        .map(|media_type| {
-          (
-            PathBuf::from(format!(
-              "{}{}",
-              path_no_ext,
-              media_type.as_ts_extension()
-            )),
-            reason,
-          )
-        })
-        .collect::<Vec<_>>()
-    }
-
-    if specifier.scheme() != "file" {
-      return None;
-    }
-
-    let path = specifier_to_file_path(specifier).ok()?;
-
-    #[derive(Clone, Copy)]
-    enum SloppyImportsResolutionReason {
-      JsToTs,
-      NoExtension,
-      Directory,
-    }
-
-    let probe_paths: Vec<(PathBuf, SloppyImportsResolutionReason)> =
-      match self.stat_sync(&path) {
-        Some(SloppyImportsFsEntry::File) => {
-          if mode.is_types() {
-            let media_type = MediaType::from_specifier(specifier);
-            // attempt to resolve the .d.ts file before the .js file
-            let probe_media_type_types = match media_type {
-              MediaType::JavaScript => {
-                vec![(MediaType::Dts), MediaType::JavaScript]
-              }
-              MediaType::Mjs => {
-                vec![MediaType::Dmts, MediaType::Dts, MediaType::Mjs]
-              }
-              MediaType::Cjs => {
-                vec![MediaType::Dcts, MediaType::Dts, MediaType::Cjs]
-              }
-              _ => return None,
-            };
-            let path_no_ext = path_without_ext(&path, media_type)?;
-            media_types_to_paths(
-              &path_no_ext,
-              media_type,
-              probe_media_type_types,
-              SloppyImportsResolutionReason::JsToTs,
-            )
-          } else {
-            return None;
-          }
-        }
-        entry @ None | entry @ Some(SloppyImportsFsEntry::Dir) => {
-          let media_type = MediaType::from_specifier(specifier);
-          let probe_media_type_types = match media_type {
-            MediaType::JavaScript => (
-              if mode.is_types() {
-                vec![MediaType::TypeScript, MediaType::Tsx, MediaType::Dts]
-              } else {
-                vec![MediaType::TypeScript, MediaType::Tsx]
-              },
-              SloppyImportsResolutionReason::JsToTs,
-            ),
-            MediaType::Jsx => {
-              (vec![MediaType::Tsx], SloppyImportsResolutionReason::JsToTs)
-            }
-            MediaType::Mjs => (
-              if mode.is_types() {
-                vec![MediaType::Mts, MediaType::Dmts, MediaType::Dts]
-              } else {
-                vec![MediaType::Mts]
-              },
-              SloppyImportsResolutionReason::JsToTs,
-            ),
-            MediaType::Cjs => (
-              if mode.is_types() {
-                vec![MediaType::Cts, MediaType::Dcts, MediaType::Dts]
-              } else {
-                vec![MediaType::Cts]
-              },
-              SloppyImportsResolutionReason::JsToTs,
-            ),
-            MediaType::TypeScript
-            | MediaType::Mts
-            | MediaType::Cts
-            | MediaType::Dts
-            | MediaType::Dmts
-            | MediaType::Dcts
-            | MediaType::Tsx
-            | MediaType::Json
-            | MediaType::Wasm
-            | MediaType::TsBuildInfo
-            | MediaType::SourceMap => {
-              return None;
-            }
-            MediaType::Unknown => (
-              if mode.is_types() {
-                vec![
-                  MediaType::TypeScript,
-                  MediaType::Tsx,
-                  MediaType::Mts,
-                  MediaType::Dts,
-                  MediaType::Dmts,
-                  MediaType::Dcts,
-                  MediaType::JavaScript,
-                  MediaType::Jsx,
-                  MediaType::Mjs,
-                ]
-              } else {
-                vec![
-                  MediaType::TypeScript,
-                  MediaType::JavaScript,
-                  MediaType::Tsx,
-                  MediaType::Jsx,
-                  MediaType::Mts,
-                  MediaType::Mjs,
-                ]
-              },
-              SloppyImportsResolutionReason::NoExtension,
-            ),
-          };
-          let mut probe_paths = match path_without_ext(&path, media_type) {
-            Some(path_no_ext) => media_types_to_paths(
-              &path_no_ext,
-              media_type,
-              probe_media_type_types.0,
-              probe_media_type_types.1,
-            ),
-            None => vec![],
-          };
-
-          if matches!(entry, Some(SloppyImportsFsEntry::Dir)) {
-            // try to resolve at the index file
-            if mode.is_types() {
-              probe_paths.push((
-                path.join("index.ts"),
-                SloppyImportsResolutionReason::Directory,
-              ));
-
-              probe_paths.push((
-                path.join("index.mts"),
-                SloppyImportsResolutionReason::Directory,
-              ));
-              probe_paths.push((
-                path.join("index.d.ts"),
-                SloppyImportsResolutionReason::Directory,
-              ));
-              probe_paths.push((
-                path.join("index.d.mts"),
-                SloppyImportsResolutionReason::Directory,
-              ));
-              probe_paths.push((
-                path.join("index.js"),
-                SloppyImportsResolutionReason::Directory,
-              ));
-              probe_paths.push((
-                path.join("index.mjs"),
-                SloppyImportsResolutionReason::Directory,
-              ));
-              probe_paths.push((
-                path.join("index.tsx"),
-                SloppyImportsResolutionReason::Directory,
-              ));
-              probe_paths.push((
-                path.join("index.jsx"),
-                SloppyImportsResolutionReason::Directory,
-              ));
-            } else {
-              probe_paths.push((
-                path.join("index.ts"),
-                SloppyImportsResolutionReason::Directory,
-              ));
-              probe_paths.push((
-                path.join("index.mts"),
-                SloppyImportsResolutionReason::Directory,
-              ));
-              probe_paths.push((
-                path.join("index.tsx"),
-                SloppyImportsResolutionReason::Directory,
-              ));
-              probe_paths.push((
-                path.join("index.js"),
-                SloppyImportsResolutionReason::Directory,
-              ));
-              probe_paths.push((
-                path.join("index.mjs"),
-                SloppyImportsResolutionReason::Directory,
-              ));
-              probe_paths.push((
-                path.join("index.jsx"),
-                SloppyImportsResolutionReason::Directory,
-              ));
-            }
-          }
-          if probe_paths.is_empty() {
-            return None;
-          }
-          probe_paths
-        }
-      };
-
-    for (probe_path, reason) in probe_paths {
-      if self.stat_sync(&probe_path) == Some(SloppyImportsFsEntry::File) {
-        if let Ok(specifier) = ModuleSpecifier::from_file_path(probe_path) {
-          match reason {
-            SloppyImportsResolutionReason::JsToTs => {
-              return Some(SloppyImportsResolution::JsToTs(specifier));
-            }
-            SloppyImportsResolutionReason::NoExtension => {
-              return Some(SloppyImportsResolution::NoExtension(specifier));
-            }
-            SloppyImportsResolutionReason::Directory => {
-              return Some(SloppyImportsResolution::Directory(specifier));
-            }
-          }
-        }
-      }
-    }
-
-    None
-  }
-
-  fn stat_sync(&self, path: &Path) -> Option<SloppyImportsFsEntry> {
+    path: &Path,
+  ) -> Option<deno_resolver::sloppy_imports::SloppyImportsFsEntry> {
     if let Some(cache) = &self.cache {
       if let Some(entry) = cache.get(path) {
         return *entry;
       }
     }
 
-    let entry = self
-      .fs
-      .stat_sync(path)
-      .ok()
-      .and_then(|stat| SloppyImportsFsEntry::from_fs_stat(&stat));
+    let entry = self.fs.stat_sync(path).ok().and_then(|stat| {
+      if stat.is_file {
+        Some(deno_resolver::sloppy_imports::SloppyImportsFsEntry::File)
+      } else if stat.is_directory {
+        Some(deno_resolver::sloppy_imports::SloppyImportsFsEntry::Dir)
+      } else {
+        None
+      }
+    });
+
     if let Some(cache) = &self.cache {
       cache.insert(path.to_owned(), entry);
     }
     entry
   }
 }
-
-#[cfg(test)]
-mod test {
-  use test_util::TestContext;
-
-  use super::*;
-
-  #[test]
-  fn test_unstable_sloppy_imports() {
-    fn resolve(specifier: &ModuleSpecifier) -> Option<SloppyImportsResolution> {
-      resolve_with_mode(specifier, ResolutionMode::Execution)
-    }
-
-    fn resolve_types(
-      specifier: &ModuleSpecifier,
-    ) -> Option<SloppyImportsResolution> {
-      resolve_with_mode(specifier, ResolutionMode::Types)
-    }
-
-    fn resolve_with_mode(
-      specifier: &ModuleSpecifier,
-      mode: ResolutionMode,
-    ) -> Option<SloppyImportsResolution> {
-      SloppyImportsResolver::new(Arc::new(deno_fs::RealFs))
-        .resolve(specifier, mode)
-    }
-
-    let context = TestContext::default();
-    let temp_dir = context.temp_dir().path();
-
-    // scenarios like resolving ./example.js to ./example.ts
-    for (ext_from, ext_to) in [("js", "ts"), ("js", "tsx"), ("mjs", "mts")] {
-      let ts_file = temp_dir.join(format!("file.{}", ext_to));
-      ts_file.write("");
-      assert_eq!(resolve(&ts_file.url_file()), None);
-      assert_eq!(
-        resolve(
-          &temp_dir
-            .url_dir()
-            .join(&format!("file.{}", ext_from))
-            .unwrap()
-        ),
-        Some(SloppyImportsResolution::JsToTs(ts_file.url_file())),
-      );
-      ts_file.remove_file();
-    }
-
-    // no extension scenarios
-    for ext in ["js", "ts", "js", "tsx", "jsx", "mjs", "mts"] {
-      let file = temp_dir.join(format!("file.{}", ext));
-      file.write("");
-      assert_eq!(
-        resolve(
-          &temp_dir
-            .url_dir()
-            .join("file") // no ext
-            .unwrap()
-        ),
-        Some(SloppyImportsResolution::NoExtension(file.url_file()))
-      );
-      file.remove_file();
-    }
-
-    // .ts and .js exists, .js specified (goes to specified)
-    {
-      let ts_file = temp_dir.join("file.ts");
-      ts_file.write("");
-      let js_file = temp_dir.join("file.js");
-      js_file.write("");
-      assert_eq!(resolve(&js_file.url_file()), None);
-    }
-
-    // only js exists, .js specified
-    {
-      let js_only_file = temp_dir.join("js_only.js");
-      js_only_file.write("");
-      assert_eq!(resolve(&js_only_file.url_file()), None);
-      assert_eq!(resolve_types(&js_only_file.url_file()), None);
-    }
-
-    // resolving a directory to an index file
-    {
-      let routes_dir = temp_dir.join("routes");
-      routes_dir.create_dir_all();
-      let index_file = routes_dir.join("index.ts");
-      index_file.write("");
-      assert_eq!(
-        resolve(&routes_dir.url_file()),
-        Some(SloppyImportsResolution::Directory(index_file.url_file())),
-      );
-    }
-
-    // both a directory and a file with specifier is present
-    {
-      let api_dir = temp_dir.join("api");
-      api_dir.create_dir_all();
-      let bar_file = api_dir.join("bar.ts");
-      bar_file.write("");
-      let api_file = temp_dir.join("api.ts");
-      api_file.write("");
-      assert_eq!(
-        resolve(&api_dir.url_file()),
-        Some(SloppyImportsResolution::NoExtension(api_file.url_file())),
-      );
-    }
-  }
-
-  #[test]
-  fn test_sloppy_import_resolution_suggestion_message() {
-    // directory
-    assert_eq!(
-      SloppyImportsResolution::Directory(
-        ModuleSpecifier::parse("file:///dir/index.js").unwrap()
-      )
-      .as_suggestion_message(),
-      "Maybe specify path to 'index.js' file in directory instead"
-    );
-    // no ext
-    assert_eq!(
-      SloppyImportsResolution::NoExtension(
-        ModuleSpecifier::parse("file:///dir/index.mjs").unwrap()
-      )
-      .as_suggestion_message(),
-      "Maybe add a '.mjs' extension"
-    );
-    // js to ts
-    assert_eq!(
-      SloppyImportsResolution::JsToTs(
-        ModuleSpecifier::parse("file:///dir/index.mts").unwrap()
-      )
-      .as_suggestion_message(),
-      "Maybe change the extension to '.mts'"
-    );
-  }
-}
diff --git a/cli/schemas/config-file.v1.json b/cli/schemas/config-file.v1.json
index af18e6f21c..9f4737fa0a 100644
--- a/cli/schemas/config-file.v1.json
+++ b/cli/schemas/config-file.v1.json
@@ -291,7 +291,7 @@
               "type": "array",
               "description": "List of tag names that will be run. Empty list disables all tags and will only use rules from `include`.",
               "items": {
-                "type": "string"
+                "$ref": "https://raw.githubusercontent.com/denoland/deno_lint/main/schemas/tags.v1.json"
               },
               "minItems": 0,
               "uniqueItems": true
@@ -300,7 +300,7 @@
               "type": "array",
               "description": "List of rule names that will be excluded from configured tag sets. If the same rule is in `include` it will be run.",
               "items": {
-                "type": "string"
+                "$ref": "https://raw.githubusercontent.com/denoland/deno_lint/main/schemas/rules.v1.json"
               },
               "minItems": 0,
               "uniqueItems": true
@@ -309,7 +309,7 @@
               "type": "array",
               "description": "List of rule names that will be run. Even if the same rule is in `exclude` it will be run.",
               "items": {
-                "type": "string"
+                "$ref": "https://raw.githubusercontent.com/denoland/deno_lint/main/schemas/rules.v1.json"
               },
               "minItems": 0,
               "uniqueItems": true
@@ -530,9 +530,11 @@
           "cron",
           "ffi",
           "fs",
+          "fmt-component",
           "http",
           "kv",
           "net",
+          "node-globals",
           "sloppy-imports",
           "temporal",
           "unsafe-proto",
diff --git a/cli/standalone/binary.rs b/cli/standalone/binary.rs
index 1290a238f3..ebcbf3ee62 100644
--- a/cli/standalone/binary.rs
+++ b/cli/standalone/binary.rs
@@ -9,14 +9,19 @@ use std::ffi::OsString;
 use std::fs;
 use std::fs::File;
 use std::future::Future;
+use std::io::ErrorKind;
 use std::io::Read;
 use std::io::Seek;
 use std::io::SeekFrom;
 use std::io::Write;
+use std::ops::Range;
 use std::path::Path;
 use std::path::PathBuf;
 use std::process::Command;
+use std::sync::Arc;
 
+use deno_ast::MediaType;
+use deno_ast::ModuleKind;
 use deno_ast::ModuleSpecifier;
 use deno_config::workspace::PackageJsonDepResolution;
 use deno_config::workspace::ResolverWorkspaceJsrPackage;
@@ -30,13 +35,23 @@ use deno_core::futures::AsyncReadExt;
 use deno_core::futures::AsyncSeekExt;
 use deno_core::serde_json;
 use deno_core::url::Url;
+use deno_graph::source::RealFileSystem;
+use deno_graph::ModuleGraph;
+use deno_npm::resolution::SerializedNpmResolutionSnapshot;
+use deno_npm::resolution::SerializedNpmResolutionSnapshotPackage;
+use deno_npm::resolution::ValidSerializedNpmResolutionSnapshot;
+use deno_npm::NpmPackageId;
 use deno_npm::NpmSystemInfo;
+use deno_runtime::deno_fs;
+use deno_runtime::deno_fs::FileSystem;
+use deno_runtime::deno_fs::RealFs;
+use deno_runtime::deno_io::fs::FsError;
 use deno_runtime::deno_node::PackageJson;
+use deno_runtime::ops::otel::OtelConfig;
 use deno_semver::npm::NpmVersionReqParseError;
 use deno_semver::package::PackageReq;
 use deno_semver::Version;
 use deno_semver::VersionReqSpecifierParseError;
-use eszip::EszipRelativeFileBaseUrl;
 use indexmap::IndexMap;
 use log::Level;
 use serde::Deserialize;
@@ -49,10 +64,12 @@ use crate::args::NpmInstallDepsProvider;
 use crate::args::PermissionFlags;
 use crate::args::UnstableConfig;
 use crate::cache::DenoDir;
+use crate::emit::Emitter;
 use crate::file_fetcher::FileFetcher;
 use crate::http_util::HttpClientProvider;
 use crate::npm::CliNpmResolver;
 use crate::npm::InnerCliNpmResolverRef;
+use crate::resolver::CjsTracker;
 use crate::shared::ReleaseChannel;
 use crate::standalone::virtual_fs::VfsEntry;
 use crate::util::archive;
@@ -60,12 +77,63 @@ use crate::util::fs::canonicalize_path_maybe_not_exists;
 use crate::util::progress_bar::ProgressBar;
 use crate::util::progress_bar::ProgressBarStyle;
 
+use super::file_system::DenoCompileFileSystem;
+use super::serialization::deserialize_binary_data_section;
+use super::serialization::serialize_binary_data_section;
+use super::serialization::DenoCompileModuleData;
+use super::serialization::DeserializedDataSection;
+use super::serialization::RemoteModulesStore;
+use super::serialization::RemoteModulesStoreBuilder;
 use super::virtual_fs::FileBackedVfs;
 use super::virtual_fs::VfsBuilder;
 use super::virtual_fs::VfsRoot;
 use super::virtual_fs::VirtualDirectory;
 
-const MAGIC_TRAILER: &[u8; 8] = b"d3n0l4nd";
+/// A URL that can be designated as the base for relative URLs.
+///
+/// After creation, this URL may be used to get the key for a
+/// module in the binary.
+#[derive(Debug, Clone, Copy, PartialEq, Eq, Hash)]
+pub struct StandaloneRelativeFileBaseUrl<'a>(&'a Url);
+
+impl<'a> From<&'a Url> for StandaloneRelativeFileBaseUrl<'a> {
+  fn from(url: &'a Url) -> Self {
+    Self(url)
+  }
+}
+
+impl<'a> StandaloneRelativeFileBaseUrl<'a> {
+  pub fn new(url: &'a Url) -> Self {
+    debug_assert_eq!(url.scheme(), "file");
+    Self(url)
+  }
+
+  /// Gets the module map key of the provided specifier.
+  ///
+  /// * Descendant file specifiers will be made relative to the base.
+  /// * Non-descendant file specifiers will stay as-is (absolute).
+  /// * Non-file specifiers will stay as-is.
+  pub fn specifier_key<'b>(&self, target: &'b Url) -> Cow<'b, str> {
+    if target.scheme() != "file" {
+      return Cow::Borrowed(target.as_str());
+    }
+
+    match self.0.make_relative(target) {
+      Some(relative) => {
+        if relative.starts_with("../") {
+          Cow::Borrowed(target.as_str())
+        } else {
+          Cow::Owned(relative)
+        }
+      }
+      None => Cow::Borrowed(target.as_str()),
+    }
+  }
+
+  pub fn inner(&self) -> &Url {
+    self.0
+  }
+}
 
 #[derive(Deserialize, Serialize)]
 pub enum NodeModules {
@@ -118,80 +186,26 @@ pub struct Metadata {
   pub entrypoint_key: String,
   pub node_modules: Option<NodeModules>,
   pub unstable_config: UnstableConfig,
-}
-
-pub fn load_npm_vfs(root_dir_path: PathBuf) -> Result<FileBackedVfs, AnyError> {
-  let data = libsui::find_section("d3n0l4nd").unwrap();
-
-  // We do the first part sync so it can complete quickly
-  let trailer: [u8; TRAILER_SIZE] = data[0..TRAILER_SIZE].try_into().unwrap();
-  let trailer = match Trailer::parse(&trailer)? {
-    None => panic!("Could not find trailer"),
-    Some(trailer) => trailer,
-  };
-  let data = &data[TRAILER_SIZE..];
-
-  let vfs_data =
-    &data[trailer.npm_vfs_pos as usize..trailer.npm_files_pos as usize];
-  let mut dir: VirtualDirectory = serde_json::from_slice(vfs_data)?;
-
-  // align the name of the directory with the root dir
-  dir.name = root_dir_path
-    .file_name()
-    .unwrap()
-    .to_string_lossy()
-    .to_string();
-
-  let fs_root = VfsRoot {
-    dir,
-    root_path: root_dir_path,
-    start_file_offset: trailer.npm_files_pos,
-  };
-  Ok(FileBackedVfs::new(data.to_vec(), fs_root))
+  pub otel_config: Option<OtelConfig>, // None means disabled.
 }
 
 fn write_binary_bytes(
   mut file_writer: File,
   original_bin: Vec<u8>,
   metadata: &Metadata,
-  eszip: eszip::EszipV2,
-  npm_vfs: Option<&VirtualDirectory>,
-  npm_files: &Vec<Vec<u8>>,
+  npm_snapshot: Option<SerializedNpmResolutionSnapshot>,
+  remote_modules: &RemoteModulesStoreBuilder,
+  vfs: VfsBuilder,
   compile_flags: &CompileFlags,
 ) -> Result<(), AnyError> {
-  let metadata = serde_json::to_string(metadata)?.as_bytes().to_vec();
-  let npm_vfs = serde_json::to_string(&npm_vfs)?.as_bytes().to_vec();
-  let eszip_archive = eszip.into_bytes();
-
-  let mut writer = Vec::new();
-
-  // write the trailer, which includes the positions
-  // of the data blocks in the file
-  writer.write_all(&{
-    let metadata_pos = eszip_archive.len() as u64;
-    let npm_vfs_pos = metadata_pos + (metadata.len() as u64);
-    let npm_files_pos = npm_vfs_pos + (npm_vfs.len() as u64);
-    Trailer {
-      eszip_pos: 0,
-      metadata_pos,
-      npm_vfs_pos,
-      npm_files_pos,
-    }
-    .as_bytes()
-  })?;
-
-  writer.write_all(&eszip_archive)?;
-  writer.write_all(&metadata)?;
-  writer.write_all(&npm_vfs)?;
-  for file in npm_files {
-    writer.write_all(file)?;
-  }
+  let data_section_bytes =
+    serialize_binary_data_section(metadata, npm_snapshot, remote_modules, vfs)?;
 
   let target = compile_flags.resolve_target();
   if target.contains("linux") {
     libsui::Elf::new(&original_bin).append(
       "d3n0l4nd",
-      &writer,
+      &data_section_bytes,
       &mut file_writer,
     )?;
   } else if target.contains("windows") {
@@ -201,11 +215,11 @@ fn write_binary_bytes(
       pe = pe.set_icon(&icon)?;
     }
 
-    pe.write_resource("d3n0l4nd", writer)?
+    pe.write_resource("d3n0l4nd", data_section_bytes)?
       .build(&mut file_writer)?;
   } else if target.contains("darwin") {
     libsui::Macho::from(original_bin)?
-      .write_section("d3n0l4nd", writer)?
+      .write_section("d3n0l4nd", data_section_bytes)?
       .build_and_sign(&mut file_writer)?;
   }
   Ok(())
@@ -221,6 +235,67 @@ pub fn is_standalone_binary(exe_path: &Path) -> bool {
     || libsui::utils::is_macho(&data)
 }
 
+pub struct StandaloneData {
+  pub fs: Arc<dyn deno_fs::FileSystem>,
+  pub metadata: Metadata,
+  pub modules: StandaloneModules,
+  pub npm_snapshot: Option<ValidSerializedNpmResolutionSnapshot>,
+  pub root_path: PathBuf,
+  pub vfs: Arc<FileBackedVfs>,
+}
+
+pub struct StandaloneModules {
+  remote_modules: RemoteModulesStore,
+  vfs: Arc<FileBackedVfs>,
+}
+
+impl StandaloneModules {
+  pub fn resolve_specifier<'a>(
+    &'a self,
+    specifier: &'a ModuleSpecifier,
+  ) -> Result<Option<&'a ModuleSpecifier>, AnyError> {
+    if specifier.scheme() == "file" {
+      Ok(Some(specifier))
+    } else {
+      self.remote_modules.resolve_specifier(specifier)
+    }
+  }
+
+  pub fn has_file(&self, path: &Path) -> bool {
+    self.vfs.file_entry(path).is_ok()
+  }
+
+  pub fn read<'a>(
+    &'a self,
+    specifier: &'a ModuleSpecifier,
+  ) -> Result<Option<DenoCompileModuleData<'a>>, AnyError> {
+    if specifier.scheme() == "file" {
+      let path = deno_path_util::url_to_file_path(specifier)?;
+      let bytes = match self.vfs.file_entry(&path) {
+        Ok(entry) => self.vfs.read_file_all(entry)?,
+        Err(err) if err.kind() == ErrorKind::NotFound => {
+          let bytes = match RealFs.read_file_sync(&path, None) {
+            Ok(bytes) => bytes,
+            Err(FsError::Io(err)) if err.kind() == ErrorKind::NotFound => {
+              return Ok(None)
+            }
+            Err(err) => return Err(err.into()),
+          };
+          Cow::Owned(bytes)
+        }
+        Err(err) => return Err(err.into()),
+      };
+      Ok(Some(DenoCompileModuleData {
+        media_type: MediaType::from_specifier(specifier),
+        specifier,
+        data: bytes,
+      }))
+    } else {
+      self.remote_modules.read(specifier)
+    }
+  }
+}
+
 /// This function will try to run this binary as a standalone binary
 /// produced by `deno compile`. It determines if this is a standalone
 /// binary by skipping over the trailer width at the end of the file,
@@ -228,110 +303,67 @@ pub fn is_standalone_binary(exe_path: &Path) -> bool {
 /// the bundle is executed. If not, this function exits with `Ok(None)`.
 pub fn extract_standalone(
   cli_args: Cow<Vec<OsString>>,
-) -> Result<
-  Option<impl Future<Output = Result<(Metadata, eszip::EszipV2), AnyError>>>,
-  AnyError,
-> {
+) -> Result<Option<StandaloneData>, AnyError> {
   let Some(data) = libsui::find_section("d3n0l4nd") else {
     return Ok(None);
   };
 
-  // We do the first part sync so it can complete quickly
-  let trailer = match Trailer::parse(&data[0..TRAILER_SIZE])? {
+  let DeserializedDataSection {
+    mut metadata,
+    npm_snapshot,
+    remote_modules,
+    mut vfs_dir,
+    vfs_files_data,
+  } = match deserialize_binary_data_section(data)? {
+    Some(data_section) => data_section,
     None => return Ok(None),
-    Some(trailer) => trailer,
   };
 
+  let root_path = {
+    let maybe_current_exe = std::env::current_exe().ok();
+    let current_exe_name = maybe_current_exe
+      .as_ref()
+      .and_then(|p| p.file_name())
+      .map(|p| p.to_string_lossy())
+      // should never happen
+      .unwrap_or_else(|| Cow::Borrowed("binary"));
+    std::env::temp_dir().join(format!("deno-compile-{}", current_exe_name))
+  };
   let cli_args = cli_args.into_owned();
-  // If we have an eszip, read it out
-  Ok(Some(async move {
-    let bufreader =
-      deno_core::futures::io::BufReader::new(&data[TRAILER_SIZE..]);
+  metadata.argv.reserve(cli_args.len() - 1);
+  for arg in cli_args.into_iter().skip(1) {
+    metadata.argv.push(arg.into_string().unwrap());
+  }
+  let vfs = {
+    // align the name of the directory with the root dir
+    vfs_dir.name = root_path.file_name().unwrap().to_string_lossy().to_string();
 
-    let (eszip, loader) = eszip::EszipV2::parse(bufreader)
-      .await
-      .context("Failed to parse eszip header")?;
-
-    let bufreader = loader.await.context("Failed to parse eszip archive")?;
-
-    let mut metadata = String::new();
-
-    bufreader
-      .take(trailer.metadata_len())
-      .read_to_string(&mut metadata)
-      .await
-      .context("Failed to read metadata from the current executable")?;
-
-    let mut metadata: Metadata = serde_json::from_str(&metadata).unwrap();
-    metadata.argv.reserve(cli_args.len() - 1);
-    for arg in cli_args.into_iter().skip(1) {
-      metadata.argv.push(arg.into_string().unwrap());
-    }
-
-    Ok((metadata, eszip))
+    let fs_root = VfsRoot {
+      dir: vfs_dir,
+      root_path: root_path.clone(),
+      start_file_offset: 0,
+    };
+    Arc::new(FileBackedVfs::new(Cow::Borrowed(vfs_files_data), fs_root))
+  };
+  let fs: Arc<dyn deno_fs::FileSystem> =
+    Arc::new(DenoCompileFileSystem::new(vfs.clone()));
+  Ok(Some(StandaloneData {
+    fs,
+    metadata,
+    modules: StandaloneModules {
+      remote_modules,
+      vfs: vfs.clone(),
+    },
+    npm_snapshot,
+    root_path,
+    vfs,
   }))
 }
 
-const TRAILER_SIZE: usize = std::mem::size_of::<Trailer>() + 8; // 8 bytes for the magic trailer string
-
-struct Trailer {
-  eszip_pos: u64,
-  metadata_pos: u64,
-  npm_vfs_pos: u64,
-  npm_files_pos: u64,
-}
-
-impl Trailer {
-  pub fn parse(trailer: &[u8]) -> Result<Option<Trailer>, AnyError> {
-    let (magic_trailer, rest) = trailer.split_at(8);
-    if magic_trailer != MAGIC_TRAILER {
-      return Ok(None);
-    }
-
-    let (eszip_archive_pos, rest) = rest.split_at(8);
-    let (metadata_pos, rest) = rest.split_at(8);
-    let (npm_vfs_pos, npm_files_pos) = rest.split_at(8);
-    let eszip_archive_pos = u64_from_bytes(eszip_archive_pos)?;
-    let metadata_pos = u64_from_bytes(metadata_pos)?;
-    let npm_vfs_pos = u64_from_bytes(npm_vfs_pos)?;
-    let npm_files_pos = u64_from_bytes(npm_files_pos)?;
-    Ok(Some(Trailer {
-      eszip_pos: eszip_archive_pos,
-      metadata_pos,
-      npm_vfs_pos,
-      npm_files_pos,
-    }))
-  }
-
-  pub fn metadata_len(&self) -> u64 {
-    self.npm_vfs_pos - self.metadata_pos
-  }
-
-  pub fn npm_vfs_len(&self) -> u64 {
-    self.npm_files_pos - self.npm_vfs_pos
-  }
-
-  pub fn as_bytes(&self) -> Vec<u8> {
-    let mut trailer = MAGIC_TRAILER.to_vec();
-    trailer.write_all(&self.eszip_pos.to_be_bytes()).unwrap();
-    trailer.write_all(&self.metadata_pos.to_be_bytes()).unwrap();
-    trailer.write_all(&self.npm_vfs_pos.to_be_bytes()).unwrap();
-    trailer
-      .write_all(&self.npm_files_pos.to_be_bytes())
-      .unwrap();
-    trailer
-  }
-}
-
-fn u64_from_bytes(arr: &[u8]) -> Result<u64, AnyError> {
-  let fixed_arr: &[u8; 8] = arr
-    .try_into()
-    .context("Failed to convert the buffer into a fixed-size array")?;
-  Ok(u64::from_be_bytes(*fixed_arr))
-}
-
 pub struct DenoCompileBinaryWriter<'a> {
+  cjs_tracker: &'a CjsTracker,
   deno_dir: &'a DenoDir,
+  emitter: &'a Emitter,
   file_fetcher: &'a FileFetcher,
   http_client_provider: &'a HttpClientProvider,
   npm_resolver: &'a dyn CliNpmResolver,
@@ -342,7 +374,9 @@ pub struct DenoCompileBinaryWriter<'a> {
 impl<'a> DenoCompileBinaryWriter<'a> {
   #[allow(clippy::too_many_arguments)]
   pub fn new(
+    cjs_tracker: &'a CjsTracker,
     deno_dir: &'a DenoDir,
+    emitter: &'a Emitter,
     file_fetcher: &'a FileFetcher,
     http_client_provider: &'a HttpClientProvider,
     npm_resolver: &'a dyn CliNpmResolver,
@@ -350,7 +384,9 @@ impl<'a> DenoCompileBinaryWriter<'a> {
     npm_system_info: NpmSystemInfo,
   ) -> Self {
     Self {
+      cjs_tracker,
       deno_dir,
+      emitter,
       file_fetcher,
       http_client_provider,
       npm_resolver,
@@ -362,8 +398,8 @@ impl<'a> DenoCompileBinaryWriter<'a> {
   pub async fn write_bin(
     &self,
     writer: File,
-    eszip: eszip::EszipV2,
-    root_dir_url: EszipRelativeFileBaseUrl<'_>,
+    graph: &ModuleGraph,
+    root_dir_url: StandaloneRelativeFileBaseUrl<'_>,
     entrypoint: &ModuleSpecifier,
     compile_flags: &CompileFlags,
     cli_options: &CliOptions,
@@ -390,15 +426,17 @@ impl<'a> DenoCompileBinaryWriter<'a> {
         )
       }
     }
-    self.write_standalone_binary(
-      writer,
-      original_binary,
-      eszip,
-      root_dir_url,
-      entrypoint,
-      cli_options,
-      compile_flags,
-    )
+    self
+      .write_standalone_binary(
+        writer,
+        original_binary,
+        graph,
+        root_dir_url,
+        entrypoint,
+        cli_options,
+        compile_flags,
+      )
+      .await
   }
 
   async fn get_base_binary(
@@ -468,14 +506,18 @@ impl<'a> DenoCompileBinaryWriter<'a> {
       self
         .http_client_provider
         .get_or_create()?
-        .download_with_progress(download_url.parse()?, None, &progress)
+        .download_with_progress_and_retries(
+          download_url.parse()?,
+          None,
+          &progress,
+        )
         .await?
     };
     let bytes = match maybe_bytes {
       Some(bytes) => bytes,
       None => {
         log::info!("Download could not be found, aborting");
-        std::process::exit(1)
+        deno_runtime::exit(1);
       }
     };
 
@@ -489,12 +531,12 @@ impl<'a> DenoCompileBinaryWriter<'a> {
   /// This functions creates a standalone deno binary by appending a bundle
   /// and magic trailer to the currently executing binary.
   #[allow(clippy::too_many_arguments)]
-  fn write_standalone_binary(
+  async fn write_standalone_binary(
     &self,
     writer: File,
     original_bin: Vec<u8>,
-    mut eszip: eszip::EszipV2,
-    root_dir_url: EszipRelativeFileBaseUrl<'_>,
+    graph: &ModuleGraph,
+    root_dir_url: StandaloneRelativeFileBaseUrl<'_>,
     entrypoint: &ModuleSpecifier,
     cli_options: &CliOptions,
     compile_flags: &CompileFlags,
@@ -508,19 +550,17 @@ impl<'a> DenoCompileBinaryWriter<'a> {
       None => None,
     };
     let root_path = root_dir_url.inner().to_file_path().unwrap();
-    let (npm_vfs, npm_files, node_modules) = match self.npm_resolver.as_inner()
+    let (maybe_npm_vfs, node_modules, npm_snapshot) = match self
+      .npm_resolver
+      .as_inner()
     {
       InnerCliNpmResolverRef::Managed(managed) => {
         let snapshot =
           managed.serialized_valid_snapshot_for_system(&self.npm_system_info);
         if !snapshot.as_serialized().packages.is_empty() {
-          let (root_dir, files) = self
-            .build_vfs(&root_path, cli_options)?
-            .into_dir_and_files();
-          eszip.add_npm_snapshot(snapshot);
+          let npm_vfs_builder = self.build_npm_vfs(&root_path, cli_options)?;
           (
-            Some(root_dir),
-            files,
+            Some(npm_vfs_builder),
             Some(NodeModules::Managed {
               node_modules_dir: self.npm_resolver.root_node_modules_path().map(
                 |path| {
@@ -532,18 +572,16 @@ impl<'a> DenoCompileBinaryWriter<'a> {
                 },
               ),
             }),
+            Some(snapshot),
           )
         } else {
-          (None, Vec::new(), None)
+          (None, None, None)
         }
       }
       InnerCliNpmResolverRef::Byonm(resolver) => {
-        let (root_dir, files) = self
-          .build_vfs(&root_path, cli_options)?
-          .into_dir_and_files();
+        let npm_vfs_builder = self.build_npm_vfs(&root_path, cli_options)?;
         (
-          Some(root_dir),
-          files,
+          Some(npm_vfs_builder),
           Some(NodeModules::Byonm {
             root_node_modules_dir: resolver.root_node_modules_path().map(
               |node_modules_dir| {
@@ -556,9 +594,69 @@ impl<'a> DenoCompileBinaryWriter<'a> {
               },
             ),
           }),
+          None,
         )
       }
     };
+    let mut vfs = if let Some(npm_vfs) = maybe_npm_vfs {
+      npm_vfs
+    } else {
+      VfsBuilder::new(root_path.clone())?
+    };
+    let mut remote_modules_store = RemoteModulesStoreBuilder::default();
+    for module in graph.modules() {
+      if module.specifier().scheme() == "data" {
+        continue; // don't store data urls as an entry as they're in the code
+      }
+      let (maybe_source, media_type) = match module {
+        deno_graph::Module::Js(m) => {
+          let source = if m.media_type.is_emittable() {
+            let is_cjs = self.cjs_tracker.is_cjs_with_known_is_script(
+              &m.specifier,
+              m.media_type,
+              m.is_script,
+            )?;
+            let module_kind = ModuleKind::from_is_cjs(is_cjs);
+            let source = self
+              .emitter
+              .emit_parsed_source(
+                &m.specifier,
+                m.media_type,
+                module_kind,
+                &m.source,
+              )
+              .await?;
+            source.into_bytes()
+          } else {
+            m.source.as_bytes().to_vec()
+          };
+          (Some(source), m.media_type)
+        }
+        deno_graph::Module::Json(m) => {
+          (Some(m.source.as_bytes().to_vec()), m.media_type)
+        }
+        deno_graph::Module::Npm(_)
+        | deno_graph::Module::Node(_)
+        | deno_graph::Module::External(_) => (None, MediaType::Unknown),
+      };
+      if module.specifier().scheme() == "file" {
+        let file_path = deno_path_util::url_to_file_path(module.specifier())?;
+        vfs
+          .add_file_with_data(
+            &file_path,
+            match maybe_source {
+              Some(source) => source,
+              None => RealFs.read_file_sync(&file_path, None)?,
+            },
+          )
+          .with_context(|| {
+            format!("Failed adding '{}'", file_path.display())
+          })?;
+      } else if let Some(source) = maybe_source {
+        remote_modules_store.add(module.specifier(), media_type, source);
+      }
+    }
+    remote_modules_store.add_redirects(&graph.redirects);
 
     let env_vars_from_env_file = match cli_options.env_file_name() {
       Some(env_filename) => {
@@ -625,20 +723,21 @@ impl<'a> DenoCompileBinaryWriter<'a> {
         sloppy_imports: cli_options.unstable_sloppy_imports(),
         features: cli_options.unstable_features(),
       },
+      otel_config: cli_options.otel_config(),
     };
 
     write_binary_bytes(
       writer,
       original_bin,
       &metadata,
-      eszip,
-      npm_vfs.as_ref(),
-      &npm_files,
+      npm_snapshot.map(|s| s.into_serialized()),
+      &remote_modules_store,
+      vfs,
       compile_flags,
     )
   }
 
-  fn build_vfs(
+  fn build_npm_vfs(
     &self,
     root_path: &Path,
     cli_options: &CliOptions,
@@ -659,8 +758,9 @@ impl<'a> DenoCompileBinaryWriter<'a> {
         } else {
           // DO NOT include the user's registry url as it may contain credentials,
           // but also don't make this dependent on the registry url
-          let root_path = npm_resolver.global_cache_root_folder();
-          let mut builder = VfsBuilder::new(root_path)?;
+          let global_cache_root_path = npm_resolver.global_cache_root_path();
+          let mut builder =
+            VfsBuilder::new(global_cache_root_path.to_path_buf())?;
           let mut packages =
             npm_resolver.all_system_packages(&self.npm_system_info);
           packages.sort_by(|a, b| a.id.cmp(&b.id)); // determinism
@@ -670,12 +770,12 @@ impl<'a> DenoCompileBinaryWriter<'a> {
             builder.add_dir_recursive(&folder)?;
           }
 
-          // Flatten all the registries folders into a single "node_modules/localhost" folder
+          // Flatten all the registries folders into a single ".deno_compile_node_modules/localhost" folder
           // that will be used by denort when loading the npm cache. This avoids us exposing
           // the user's private registry information and means we don't have to bother
           // serializing all the different registry config into the binary.
           builder.with_root_dir(|root_dir| {
-            root_dir.name = "node_modules".to_string();
+            root_dir.name = ".deno_compile_node_modules".to_string();
             let mut new_entries = Vec::with_capacity(root_dir.entries.len());
             let mut localhost_entries = IndexMap::new();
             for entry in std::mem::take(&mut root_dir.entries) {
@@ -710,6 +810,8 @@ impl<'a> DenoCompileBinaryWriter<'a> {
             root_dir.entries = new_entries;
           });
 
+          builder.set_new_root_path(root_path.to_path_buf())?;
+
           Ok(builder)
         }
       }
diff --git a/cli/standalone/file_system.rs b/cli/standalone/file_system.rs
index 536b17f277..712c6ee918 100644
--- a/cli/standalone/file_system.rs
+++ b/cli/standalone/file_system.rs
@@ -22,8 +22,8 @@ use super::virtual_fs::FileBackedVfs;
 pub struct DenoCompileFileSystem(Arc<FileBackedVfs>);
 
 impl DenoCompileFileSystem {
-  pub fn new(vfs: FileBackedVfs) -> Self {
-    Self(Arc::new(vfs))
+  pub fn new(vfs: Arc<FileBackedVfs>) -> Self {
+    Self(vfs)
   }
 
   fn error_if_in_vfs(&self, path: &Path) -> FsResult<()> {
@@ -102,7 +102,7 @@ impl FileSystem for DenoCompileFileSystem {
     &self,
     path: &Path,
     recursive: bool,
-    mode: u32,
+    mode: Option<u32>,
   ) -> FsResult<()> {
     self.error_if_in_vfs(path)?;
     RealFs.mkdir_sync(path, recursive, mode)
@@ -111,7 +111,7 @@ impl FileSystem for DenoCompileFileSystem {
     &self,
     path: PathBuf,
     recursive: bool,
-    mode: u32,
+    mode: Option<u32>,
   ) -> FsResult<()> {
     self.error_if_in_vfs(&path)?;
     RealFs.mkdir_async(path, recursive, mode).await
diff --git a/cli/standalone/mod.rs b/cli/standalone/mod.rs
index c501d2d6bc..e3449c1520 100644
--- a/cli/standalone/mod.rs
+++ b/cli/standalone/mod.rs
@@ -5,7 +5,10 @@
 #![allow(dead_code)]
 #![allow(unused_imports)]
 
+use binary::StandaloneData;
+use binary::StandaloneModules;
 use deno_ast::MediaType;
+use deno_cache_dir::npm::NpmCacheDir;
 use deno_config::workspace::MappedResolution;
 use deno_config::workspace::MappedResolutionError;
 use deno_config::workspace::ResolverWorkspaceJsrPackage;
@@ -16,6 +19,7 @@ use deno_core::error::type_error;
 use deno_core::error::AnyError;
 use deno_core::futures::FutureExt;
 use deno_core::v8_set_flags;
+use deno_core::FastString;
 use deno_core::FeatureChecker;
 use deno_core::ModuleLoader;
 use deno_core::ModuleSourceCode;
@@ -25,9 +29,12 @@ use deno_core::RequestedModuleType;
 use deno_core::ResolutionKind;
 use deno_npm::npm_rc::ResolvedNpmRc;
 use deno_package_json::PackageJsonDepValue;
+use deno_resolver::npm::NpmReqResolverOptions;
 use deno_runtime::deno_fs;
 use deno_runtime::deno_node::create_host_defined_options;
+use deno_runtime::deno_node::NodeRequireLoader;
 use deno_runtime::deno_node::NodeResolver;
+use deno_runtime::deno_node::PackageJsonResolver;
 use deno_runtime::deno_permissions::Permissions;
 use deno_runtime::deno_permissions::PermissionsContainer;
 use deno_runtime::deno_tls::rustls::RootCertStore;
@@ -37,10 +44,12 @@ use deno_runtime::permissions::RuntimePermissionDescriptorParser;
 use deno_runtime::WorkerExecutionMode;
 use deno_runtime::WorkerLogLevel;
 use deno_semver::npm::NpmPackageReqReference;
-use eszip::EszipRelativeFileBaseUrl;
 use import_map::parse_from_json;
 use node_resolver::analyze::NodeCodeTranslator;
+use node_resolver::errors::ClosestPkgJsonError;
+use node_resolver::NodeModuleKind;
 use node_resolver::NodeResolutionMode;
+use serialization::DenoCompileModuleSource;
 use std::borrow::Cow;
 use std::rc::Rc;
 use std::sync::Arc;
@@ -53,78 +62,57 @@ use crate::args::CacheSetting;
 use crate::args::NpmInstallDepsProvider;
 use crate::args::StorageKeyResolver;
 use crate::cache::Caches;
+use crate::cache::DenoCacheEnvFsAdapter;
 use crate::cache::DenoDirProvider;
 use crate::cache::NodeAnalysisCache;
+use crate::cache::RealDenoCacheEnv;
 use crate::http_util::HttpClientProvider;
 use crate::node::CliCjsCodeAnalyzer;
+use crate::node::CliNodeCodeTranslator;
 use crate::npm::create_cli_npm_resolver;
-use crate::npm::CliNpmResolverByonmCreateOptions;
+use crate::npm::create_in_npm_pkg_checker;
+use crate::npm::CliByonmNpmResolverCreateOptions;
+use crate::npm::CliManagedInNpmPkgCheckerCreateOptions;
+use crate::npm::CliManagedNpmResolverCreateOptions;
+use crate::npm::CliNpmResolver;
 use crate::npm::CliNpmResolverCreateOptions;
-use crate::npm::CliNpmResolverManagedCreateOptions;
 use crate::npm::CliNpmResolverManagedSnapshotOption;
-use crate::npm::NpmCacheDir;
-use crate::resolver::CjsResolutionStore;
-use crate::resolver::CliNodeResolver;
+use crate::npm::CreateInNpmPkgCheckerOptions;
+use crate::resolver::CjsTracker;
+use crate::resolver::CliDenoResolverFs;
+use crate::resolver::CliNpmReqResolver;
+use crate::resolver::IsCjsResolverOptions;
 use crate::resolver::NpmModuleLoader;
 use crate::util::progress_bar::ProgressBar;
 use crate::util::progress_bar::ProgressBarStyle;
 use crate::util::v8::construct_v8_flags;
 use crate::worker::CliMainWorkerFactory;
 use crate::worker::CliMainWorkerOptions;
-use crate::worker::ModuleLoaderAndSourceMapGetter;
+use crate::worker::CreateModuleLoaderResult;
 use crate::worker::ModuleLoaderFactory;
 
 pub mod binary;
 mod file_system;
+mod serialization;
 mod virtual_fs;
 
 pub use binary::extract_standalone;
 pub use binary::is_standalone_binary;
 pub use binary::DenoCompileBinaryWriter;
 
-use self::binary::load_npm_vfs;
 use self::binary::Metadata;
 use self::file_system::DenoCompileFileSystem;
 
-struct WorkspaceEszipModule {
-  specifier: ModuleSpecifier,
-  inner: eszip::Module,
-}
-
-struct WorkspaceEszip {
-  eszip: eszip::EszipV2,
-  root_dir_url: Arc<ModuleSpecifier>,
-}
-
-impl WorkspaceEszip {
-  pub fn get_module(
-    &self,
-    specifier: &ModuleSpecifier,
-  ) -> Option<WorkspaceEszipModule> {
-    if specifier.scheme() == "file" {
-      let specifier_key = EszipRelativeFileBaseUrl::new(&self.root_dir_url)
-        .specifier_key(specifier);
-      let module = self.eszip.get_module(&specifier_key)?;
-      let specifier = self.root_dir_url.join(&module.specifier).unwrap();
-      Some(WorkspaceEszipModule {
-        specifier,
-        inner: module,
-      })
-    } else {
-      let module = self.eszip.get_module(specifier.as_str())?;
-      Some(WorkspaceEszipModule {
-        specifier: ModuleSpecifier::parse(&module.specifier).unwrap(),
-        inner: module,
-      })
-    }
-  }
-}
-
 struct SharedModuleLoaderState {
-  eszip: WorkspaceEszip,
-  workspace_resolver: WorkspaceResolver,
-  node_resolver: Arc<CliNodeResolver>,
+  cjs_tracker: Arc<CjsTracker>,
+  fs: Arc<dyn deno_fs::FileSystem>,
+  modules: StandaloneModules,
+  node_code_translator: Arc<CliNodeCodeTranslator>,
+  node_resolver: Arc<NodeResolver>,
   npm_module_loader: Arc<NpmModuleLoader>,
+  npm_req_resolver: Arc<CliNpmReqResolver>,
+  npm_resolver: Arc<dyn CliNpmResolver>,
+  workspace_resolver: WorkspaceResolver,
 }
 
 #[derive(Clone)]
@@ -132,6 +120,12 @@ struct EmbeddedModuleLoader {
   shared: Arc<SharedModuleLoaderState>,
 }
 
+impl std::fmt::Debug for EmbeddedModuleLoader {
+  fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+    f.debug_struct("EmbeddedModuleLoader").finish()
+  }
+}
+
 pub const MODULE_NOT_FOUND: &str = "Module not found";
 pub const UNSUPPORTED_SCHEME: &str = "Unsupported scheme";
 
@@ -156,13 +150,27 @@ impl ModuleLoader for EmbeddedModuleLoader {
         type_error(format!("Referrer uses invalid specifier: {}", err))
       })?
     };
+    let referrer_kind = if self
+      .shared
+      .cjs_tracker
+      .is_maybe_cjs(&referrer, MediaType::from_specifier(&referrer))?
+    {
+      NodeModuleKind::Cjs
+    } else {
+      NodeModuleKind::Esm
+    };
 
     if self.shared.node_resolver.in_npm_package(&referrer) {
       return Ok(
         self
           .shared
           .node_resolver
-          .resolve(raw_specifier, &referrer, NodeResolutionMode::Execution)?
+          .resolve(
+            raw_specifier,
+            &referrer,
+            referrer_kind,
+            NodeResolutionMode::Execution,
+          )?
           .into_url(),
       );
     }
@@ -184,13 +192,13 @@ impl ModuleLoader for EmbeddedModuleLoader {
         self
           .shared
           .node_resolver
-          .resolve_package_sub_path_from_deno_module(
+          .resolve_package_subpath_from_deno_module(
             pkg_json.dir_path(),
             sub_path.as_deref(),
             Some(&referrer),
+            referrer_kind,
             NodeResolutionMode::Execution,
-          )?
-          .into_url(),
+          )?,
       ),
       Ok(MappedResolution::PackageJson {
         dep_result,
@@ -200,14 +208,15 @@ impl ModuleLoader for EmbeddedModuleLoader {
       }) => match dep_result.as_ref().map_err(|e| AnyError::from(e.clone()))? {
         PackageJsonDepValue::Req(req) => self
           .shared
-          .node_resolver
+          .npm_req_resolver
           .resolve_req_with_sub_path(
             req,
             sub_path.as_deref(),
             &referrer,
+            referrer_kind,
             NodeResolutionMode::Execution,
           )
-          .map(|res| res.into_url()),
+          .map_err(AnyError::from),
         PackageJsonDepValue::Workspace(version_req) => {
           let pkg_folder = self
             .shared
@@ -220,13 +229,13 @@ impl ModuleLoader for EmbeddedModuleLoader {
             self
               .shared
               .node_resolver
-              .resolve_package_sub_path_from_deno_module(
+              .resolve_package_subpath_from_deno_module(
                 pkg_folder,
                 sub_path.as_deref(),
                 Some(&referrer),
+                referrer_kind,
                 NodeResolutionMode::Execution,
-              )?
-              .into_url(),
+              )?,
           )
         }
       },
@@ -235,20 +244,19 @@ impl ModuleLoader for EmbeddedModuleLoader {
         if let Ok(reference) =
           NpmPackageReqReference::from_specifier(&specifier)
         {
-          return self
-            .shared
-            .node_resolver
-            .resolve_req_reference(
-              &reference,
-              &referrer,
-              NodeResolutionMode::Execution,
-            )
-            .map(|res| res.into_url());
+          return Ok(self.shared.npm_req_resolver.resolve_req_reference(
+            &reference,
+            &referrer,
+            referrer_kind,
+            NodeResolutionMode::Execution,
+          )?);
         }
 
         if specifier.scheme() == "jsr" {
-          if let Some(module) = self.shared.eszip.get_module(&specifier) {
-            return Ok(module.specifier);
+          if let Some(specifier) =
+            self.shared.modules.resolve_specifier(&specifier)?
+          {
+            return Ok(specifier.clone());
           }
         }
 
@@ -256,16 +264,17 @@ impl ModuleLoader for EmbeddedModuleLoader {
           self
             .shared
             .node_resolver
-            .handle_if_in_node_modules(&specifier)?
+            .handle_if_in_node_modules(&specifier)
             .unwrap_or(specifier),
         )
       }
       Err(err)
         if err.is_unmapped_bare_specifier() && referrer.scheme() == "file" =>
       {
-        let maybe_res = self.shared.node_resolver.resolve_if_for_npm_pkg(
+        let maybe_res = self.shared.npm_req_resolver.resolve_if_for_npm_pkg(
           raw_specifier,
           &referrer,
+          referrer_kind,
           NodeResolutionMode::Execution,
         )?;
         if let Some(res) = maybe_res {
@@ -343,82 +352,148 @@ impl ModuleLoader for EmbeddedModuleLoader {
       );
     }
 
-    let Some(module) = self.shared.eszip.get_module(original_specifier) else {
-      return deno_core::ModuleLoadResponse::Sync(Err(type_error(format!(
-        "{MODULE_NOT_FOUND}: {}",
-        original_specifier
-      ))));
-    };
-    let original_specifier = original_specifier.clone();
-
-    deno_core::ModuleLoadResponse::Async(
-      async move {
-        let code = module.inner.source().await.ok_or_else(|| {
-          type_error(format!("Module not found: {}", original_specifier))
-        })?;
-        let code = arc_u8_to_arc_str(code)
-          .map_err(|_| type_error("Module source is not utf-8"))?;
-        Ok(deno_core::ModuleSource::new_with_redirect(
-          match module.inner.kind {
-            eszip::ModuleKind::JavaScript => ModuleType::JavaScript,
-            eszip::ModuleKind::Json => ModuleType::Json,
-            eszip::ModuleKind::Jsonc => {
-              return Err(type_error("jsonc modules not supported"))
+    match self.shared.modules.read(original_specifier) {
+      Ok(Some(module)) => {
+        let media_type = module.media_type;
+        let (module_specifier, module_type, module_source) =
+          module.into_parts();
+        let is_maybe_cjs = match self
+          .shared
+          .cjs_tracker
+          .is_maybe_cjs(original_specifier, media_type)
+        {
+          Ok(is_maybe_cjs) => is_maybe_cjs,
+          Err(err) => {
+            return deno_core::ModuleLoadResponse::Sync(Err(type_error(
+              format!("{:?}", err),
+            )));
+          }
+        };
+        if is_maybe_cjs {
+          let original_specifier = original_specifier.clone();
+          let module_specifier = module_specifier.clone();
+          let shared = self.shared.clone();
+          deno_core::ModuleLoadResponse::Async(
+            async move {
+              let source = match module_source {
+                DenoCompileModuleSource::String(string) => {
+                  Cow::Borrowed(string)
+                }
+                DenoCompileModuleSource::Bytes(module_code_bytes) => {
+                  match module_code_bytes {
+                    Cow::Owned(bytes) => Cow::Owned(
+                      crate::util::text_encoding::from_utf8_lossy_owned(bytes),
+                    ),
+                    Cow::Borrowed(bytes) => String::from_utf8_lossy(bytes),
+                  }
+                }
+              };
+              let source = shared
+                .node_code_translator
+                .translate_cjs_to_esm(&module_specifier, Some(source))
+                .await?;
+              let module_source = match source {
+                Cow::Owned(source) => ModuleSourceCode::String(source.into()),
+                Cow::Borrowed(source) => {
+                  ModuleSourceCode::String(FastString::from_static(source))
+                }
+              };
+              Ok(deno_core::ModuleSource::new_with_redirect(
+                module_type,
+                module_source,
+                &original_specifier,
+                &module_specifier,
+                None,
+              ))
             }
-            eszip::ModuleKind::OpaqueData => {
-              unreachable!();
-            }
-          },
-          ModuleSourceCode::String(code.into()),
-          &original_specifier,
-          &module.specifier,
-          None,
-        ))
+            .boxed_local(),
+          )
+        } else {
+          let module_source = module_source.into_for_v8();
+          deno_core::ModuleLoadResponse::Sync(Ok(
+            deno_core::ModuleSource::new_with_redirect(
+              module_type,
+              module_source,
+              original_specifier,
+              module_specifier,
+              None,
+            ),
+          ))
+        }
       }
-      .boxed_local(),
-    )
+      Ok(None) => deno_core::ModuleLoadResponse::Sync(Err(type_error(
+        format!("{MODULE_NOT_FOUND}: {}", original_specifier),
+      ))),
+      Err(err) => deno_core::ModuleLoadResponse::Sync(Err(type_error(
+        format!("{:?}", err),
+      ))),
+    }
   }
 }
 
-fn arc_u8_to_arc_str(
-  arc_u8: Arc<[u8]>,
-) -> Result<Arc<str>, std::str::Utf8Error> {
-  // Check that the string is valid UTF-8.
-  std::str::from_utf8(&arc_u8)?;
-  // SAFETY: the string is valid UTF-8, and the layout Arc<[u8]> is the same as
-  // Arc<str>. This is proven by the From<Arc<str>> impl for Arc<[u8]> from the
-  // standard library.
-  Ok(unsafe {
-    std::mem::transmute::<std::sync::Arc<[u8]>, std::sync::Arc<str>>(arc_u8)
-  })
+impl NodeRequireLoader for EmbeddedModuleLoader {
+  fn ensure_read_permission<'a>(
+    &self,
+    permissions: &mut dyn deno_runtime::deno_node::NodePermissions,
+    path: &'a std::path::Path,
+  ) -> Result<Cow<'a, std::path::Path>, AnyError> {
+    if self.shared.modules.has_file(path) {
+      // allow reading if the file is in the snapshot
+      return Ok(Cow::Borrowed(path));
+    }
+
+    self
+      .shared
+      .npm_resolver
+      .ensure_read_permission(permissions, path)
+  }
+
+  fn load_text_file_lossy(
+    &self,
+    path: &std::path::Path,
+  ) -> Result<String, AnyError> {
+    Ok(self.shared.fs.read_text_file_lossy_sync(path, None)?)
+  }
+
+  fn is_maybe_cjs(
+    &self,
+    specifier: &ModuleSpecifier,
+  ) -> Result<bool, ClosestPkgJsonError> {
+    let media_type = MediaType::from_specifier(specifier);
+    self.shared.cjs_tracker.is_maybe_cjs(specifier, media_type)
+  }
 }
 
 struct StandaloneModuleLoaderFactory {
   shared: Arc<SharedModuleLoaderState>,
 }
 
+impl StandaloneModuleLoaderFactory {
+  pub fn create_result(&self) -> CreateModuleLoaderResult {
+    let loader = Rc::new(EmbeddedModuleLoader {
+      shared: self.shared.clone(),
+    });
+    CreateModuleLoaderResult {
+      module_loader: loader.clone(),
+      node_require_loader: loader,
+    }
+  }
+}
+
 impl ModuleLoaderFactory for StandaloneModuleLoaderFactory {
   fn create_for_main(
     &self,
     _root_permissions: PermissionsContainer,
-  ) -> ModuleLoaderAndSourceMapGetter {
-    ModuleLoaderAndSourceMapGetter {
-      module_loader: Rc::new(EmbeddedModuleLoader {
-        shared: self.shared.clone(),
-      }),
-    }
+  ) -> CreateModuleLoaderResult {
+    self.create_result()
   }
 
   fn create_for_worker(
     &self,
     _parent_permissions: PermissionsContainer,
     _permissions: PermissionsContainer,
-  ) -> ModuleLoaderAndSourceMapGetter {
-    ModuleLoaderAndSourceMapGetter {
-      module_loader: Rc::new(EmbeddedModuleLoader {
-        shared: self.shared.clone(),
-      }),
-    }
+  ) -> CreateModuleLoaderResult {
+    self.create_result()
   }
 }
 
@@ -437,13 +512,15 @@ impl RootCertStoreProvider for StandaloneRootCertStoreProvider {
   }
 }
 
-pub async fn run(
-  mut eszip: eszip::EszipV2,
-  metadata: Metadata,
-) -> Result<i32, AnyError> {
-  let current_exe_path = std::env::current_exe().unwrap();
-  let current_exe_name =
-    current_exe_path.file_name().unwrap().to_string_lossy();
+pub async fn run(data: StandaloneData) -> Result<i32, AnyError> {
+  let StandaloneData {
+    fs,
+    metadata,
+    modules,
+    npm_snapshot,
+    root_path,
+    vfs,
+  } = data;
   let deno_dir_provider = Arc::new(DenoDirProvider::new(None));
   let root_cert_store_provider = Arc::new(StandaloneRootCertStoreProvider {
     ca_stores: metadata.ca_stores,
@@ -457,43 +534,50 @@ pub async fn run(
   ));
   // use a dummy npm registry url
   let npm_registry_url = ModuleSpecifier::parse("https://localhost/").unwrap();
-  let root_path =
-    std::env::temp_dir().join(format!("deno-compile-{}", current_exe_name));
   let root_dir_url =
     Arc::new(ModuleSpecifier::from_directory_path(&root_path).unwrap());
   let main_module = root_dir_url.join(&metadata.entrypoint_key).unwrap();
-  let root_node_modules_path = root_path.join("node_modules");
-  let npm_cache_dir = NpmCacheDir::new(
-    root_node_modules_path.clone(),
-    vec![npm_registry_url.clone()],
-  );
-  let npm_global_cache_dir = npm_cache_dir.get_cache_location();
+  let npm_global_cache_dir = root_path.join(".deno_compile_node_modules");
   let cache_setting = CacheSetting::Only;
-  let (fs, npm_resolver, maybe_vfs_root) = match metadata.node_modules {
+  let pkg_json_resolver = Arc::new(PackageJsonResolver::new(
+    deno_runtime::deno_node::DenoFsNodeResolverEnv::new(fs.clone()),
+  ));
+  let (in_npm_pkg_checker, npm_resolver) = match metadata.node_modules {
     Some(binary::NodeModules::Managed { node_modules_dir }) => {
-      // this will always have a snapshot
-      let snapshot = eszip.take_npm_snapshot().unwrap();
-      let vfs_root_dir_path = if node_modules_dir.is_some() {
-        root_path.clone()
-      } else {
-        npm_cache_dir.root_dir().to_owned()
-      };
-      let vfs = load_npm_vfs(vfs_root_dir_path.clone())
-        .context("Failed to load npm vfs.")?;
+      // create an npmrc that uses the fake npm_registry_url to resolve packages
+      let npmrc = Arc::new(ResolvedNpmRc {
+        default_config: deno_npm::npm_rc::RegistryConfigWithUrl {
+          registry_url: npm_registry_url.clone(),
+          config: Default::default(),
+        },
+        scopes: Default::default(),
+        registry_configs: Default::default(),
+      });
+      let npm_cache_dir = Arc::new(NpmCacheDir::new(
+        &DenoCacheEnvFsAdapter(fs.as_ref()),
+        npm_global_cache_dir,
+        npmrc.get_all_known_registries_urls(),
+      ));
+      let snapshot = npm_snapshot.unwrap();
       let maybe_node_modules_path = node_modules_dir
-        .map(|node_modules_dir| vfs_root_dir_path.join(node_modules_dir));
-      let fs = Arc::new(DenoCompileFileSystem::new(vfs))
-        as Arc<dyn deno_fs::FileSystem>;
+        .map(|node_modules_dir| root_path.join(node_modules_dir));
+      let in_npm_pkg_checker =
+        create_in_npm_pkg_checker(CreateInNpmPkgCheckerOptions::Managed(
+          CliManagedInNpmPkgCheckerCreateOptions {
+            root_cache_dir_url: npm_cache_dir.root_dir_url(),
+            maybe_node_modules_path: maybe_node_modules_path.as_deref(),
+          },
+        ));
       let npm_resolver =
         create_cli_npm_resolver(CliNpmResolverCreateOptions::Managed(
-          CliNpmResolverManagedCreateOptions {
+          CliManagedNpmResolverCreateOptions {
             snapshot: CliNpmResolverManagedSnapshotOption::Specified(Some(
               snapshot,
             )),
             maybe_lockfile: None,
             fs: fs.clone(),
             http_client_provider: http_client_provider.clone(),
-            npm_global_cache_dir,
+            npm_cache_dir,
             cache_setting,
             text_only_progress_bar: progress_bar,
             maybe_node_modules_path,
@@ -502,50 +586,54 @@ pub async fn run(
               // this is only used for installing packages, which isn't necessary with deno compile
               NpmInstallDepsProvider::empty(),
             ),
-            // create an npmrc that uses the fake npm_registry_url to resolve packages
-            npmrc: Arc::new(ResolvedNpmRc {
-              default_config: deno_npm::npm_rc::RegistryConfigWithUrl {
-                registry_url: npm_registry_url.clone(),
-                config: Default::default(),
-              },
-              scopes: Default::default(),
-              registry_configs: Default::default(),
-            }),
+            npmrc,
             lifecycle_scripts: Default::default(),
           },
         ))
         .await?;
-      (fs, npm_resolver, Some(vfs_root_dir_path))
+      (in_npm_pkg_checker, npm_resolver)
     }
     Some(binary::NodeModules::Byonm {
       root_node_modules_dir,
     }) => {
-      let vfs_root_dir_path = root_path.clone();
-      let vfs = load_npm_vfs(vfs_root_dir_path.clone())
-        .context("Failed to load vfs.")?;
       let root_node_modules_dir =
         root_node_modules_dir.map(|p| vfs.root().join(p));
-      let fs = Arc::new(DenoCompileFileSystem::new(vfs))
-        as Arc<dyn deno_fs::FileSystem>;
+      let in_npm_pkg_checker =
+        create_in_npm_pkg_checker(CreateInNpmPkgCheckerOptions::Byonm);
       let npm_resolver = create_cli_npm_resolver(
-        CliNpmResolverCreateOptions::Byonm(CliNpmResolverByonmCreateOptions {
-          fs: fs.clone(),
+        CliNpmResolverCreateOptions::Byonm(CliByonmNpmResolverCreateOptions {
+          fs: CliDenoResolverFs(fs.clone()),
+          pkg_json_resolver: pkg_json_resolver.clone(),
           root_node_modules_dir,
         }),
       )
       .await?;
-      (fs, npm_resolver, Some(vfs_root_dir_path))
+      (in_npm_pkg_checker, npm_resolver)
     }
     None => {
-      let fs = Arc::new(deno_fs::RealFs) as Arc<dyn deno_fs::FileSystem>;
+      // Packages from different registries are already inlined in the binary,
+      // so no need to create actual `.npmrc` configuration.
+      let npmrc = create_default_npmrc();
+      let npm_cache_dir = Arc::new(NpmCacheDir::new(
+        &DenoCacheEnvFsAdapter(fs.as_ref()),
+        npm_global_cache_dir,
+        npmrc.get_all_known_registries_urls(),
+      ));
+      let in_npm_pkg_checker =
+        create_in_npm_pkg_checker(CreateInNpmPkgCheckerOptions::Managed(
+          CliManagedInNpmPkgCheckerCreateOptions {
+            root_cache_dir_url: npm_cache_dir.root_dir_url(),
+            maybe_node_modules_path: None,
+          },
+        ));
       let npm_resolver =
         create_cli_npm_resolver(CliNpmResolverCreateOptions::Managed(
-          CliNpmResolverManagedCreateOptions {
+          CliManagedNpmResolverCreateOptions {
             snapshot: CliNpmResolverManagedSnapshotOption::Specified(None),
             maybe_lockfile: None,
             fs: fs.clone(),
             http_client_provider: http_client_provider.clone(),
-            npm_global_cache_dir,
+            npm_cache_dir,
             cache_setting,
             text_only_progress_bar: progress_bar,
             maybe_node_modules_path: None,
@@ -554,41 +642,53 @@ pub async fn run(
               // this is only used for installing packages, which isn't necessary with deno compile
               NpmInstallDepsProvider::empty(),
             ),
-            // Packages from different registries are already inlined in the ESZip,
-            // so no need to create actual `.npmrc` configuration.
             npmrc: create_default_npmrc(),
             lifecycle_scripts: Default::default(),
           },
         ))
         .await?;
-      (fs, npm_resolver, None)
+      (in_npm_pkg_checker, npm_resolver)
     }
   };
 
   let has_node_modules_dir = npm_resolver.root_node_modules_path().is_some();
   let node_resolver = Arc::new(NodeResolver::new(
     deno_runtime::deno_node::DenoFsNodeResolverEnv::new(fs.clone()),
-    npm_resolver.clone().into_npm_resolver(),
+    in_npm_pkg_checker.clone(),
+    npm_resolver.clone().into_npm_pkg_folder_resolver(),
+    pkg_json_resolver.clone(),
+  ));
+  let cjs_tracker = Arc::new(CjsTracker::new(
+    in_npm_pkg_checker.clone(),
+    pkg_json_resolver.clone(),
+    IsCjsResolverOptions {
+      detect_cjs: !metadata.workspace_resolver.package_jsons.is_empty(),
+      is_node_main: false,
+    },
   ));
-  let cjs_resolutions = Arc::new(CjsResolutionStore::default());
   let cache_db = Caches::new(deno_dir_provider.clone());
   let node_analysis_cache = NodeAnalysisCache::new(cache_db.node_analysis_db());
-  let cli_node_resolver = Arc::new(CliNodeResolver::new(
-    cjs_resolutions.clone(),
-    fs.clone(),
-    node_resolver.clone(),
-    npm_resolver.clone(),
-  ));
+  let npm_req_resolver =
+    Arc::new(CliNpmReqResolver::new(NpmReqResolverOptions {
+      byonm_resolver: (npm_resolver.clone()).into_maybe_byonm(),
+      fs: CliDenoResolverFs(fs.clone()),
+      in_npm_pkg_checker: in_npm_pkg_checker.clone(),
+      node_resolver: node_resolver.clone(),
+      npm_req_resolver: npm_resolver.clone().into_npm_req_resolver(),
+    }));
   let cjs_esm_code_analyzer = CliCjsCodeAnalyzer::new(
     node_analysis_cache,
+    cjs_tracker.clone(),
     fs.clone(),
-    cli_node_resolver.clone(),
+    None,
   );
   let node_code_translator = Arc::new(NodeCodeTranslator::new(
     cjs_esm_code_analyzer,
     deno_runtime::deno_node::DenoFsNodeResolverEnv::new(fs.clone()),
+    in_npm_pkg_checker,
     node_resolver.clone(),
-    npm_resolver.clone().into_npm_resolver(),
+    npm_resolver.clone().into_npm_pkg_folder_resolver(),
+    pkg_json_resolver.clone(),
   ));
   let workspace_resolver = {
     let import_map = match metadata.workspace_resolver.import_map {
@@ -641,37 +741,36 @@ pub async fn run(
   };
   let module_loader_factory = StandaloneModuleLoaderFactory {
     shared: Arc::new(SharedModuleLoaderState {
-      eszip: WorkspaceEszip {
-        eszip,
-        root_dir_url,
-      },
-      workspace_resolver,
-      node_resolver: cli_node_resolver.clone(),
+      cjs_tracker: cjs_tracker.clone(),
+      fs: fs.clone(),
+      modules,
+      node_code_translator: node_code_translator.clone(),
+      node_resolver: node_resolver.clone(),
       npm_module_loader: Arc::new(NpmModuleLoader::new(
-        cjs_resolutions,
-        node_code_translator,
+        cjs_tracker.clone(),
         fs.clone(),
-        cli_node_resolver,
+        node_code_translator,
       )),
+      npm_resolver: npm_resolver.clone(),
+      workspace_resolver,
+      npm_req_resolver,
     }),
   };
 
   let permissions = {
     let mut permissions =
       metadata.permissions.to_options(/* cli_arg_urls */ &[]);
-    // if running with an npm vfs, grant read access to it
-    if let Some(vfs_root) = maybe_vfs_root {
-      match &mut permissions.allow_read {
-        Some(vec) if vec.is_empty() => {
-          // do nothing, already granted
-        }
-        Some(vec) => {
-          vec.push(vfs_root.to_string_lossy().to_string());
-        }
-        None => {
-          permissions.allow_read =
-            Some(vec![vfs_root.to_string_lossy().to_string()]);
-        }
+    // grant read access to the vfs
+    match &mut permissions.allow_read {
+      Some(vec) if vec.is_empty() => {
+        // do nothing, already granted
+      }
+      Some(vec) => {
+        vec.push(root_path.to_string_lossy().to_string());
+      }
+      None => {
+        permissions.allow_read =
+          Some(vec![root_path.to_string_lossy().to_string()]);
       }
     }
 
@@ -691,8 +790,6 @@ pub async fn run(
     }
     checker
   });
-  let permission_desc_parser =
-    Arc::new(RuntimePermissionDescriptorParser::new(fs.clone()));
   let worker_factory = CliMainWorkerFactory::new(
     Arc::new(BlobStore::default()),
     // Code cache is not supported for standalone binary yet.
@@ -705,7 +802,7 @@ pub async fn run(
     Box::new(module_loader_factory),
     node_resolver,
     npm_resolver,
-    permission_desc_parser,
+    pkg_json_resolver,
     root_cert_store_provider,
     permissions,
     StorageKeyResolver::empty(),
@@ -721,7 +818,6 @@ pub async fn run(
       inspect_wait: false,
       strace_ops: None,
       is_inspecting: false,
-      is_npm_main: main_module.scheme() == "npm",
       skip_op_registration: true,
       location: metadata.location,
       argv0: NpmPackageReqReference::from_specifier(&main_module)
@@ -739,6 +835,7 @@ pub async fn run(
       serve_port: None,
       serve_host: None,
     },
+    metadata.otel_config,
   );
 
   // Initialize v8 once from the main thread.
diff --git a/cli/standalone/serialization.rs b/cli/standalone/serialization.rs
new file mode 100644
index 0000000000..a5eb649bfd
--- /dev/null
+++ b/cli/standalone/serialization.rs
@@ -0,0 +1,661 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+use std::borrow::Cow;
+use std::collections::BTreeMap;
+use std::collections::HashMap;
+use std::io::Write;
+
+use deno_ast::MediaType;
+use deno_core::anyhow::bail;
+use deno_core::anyhow::Context;
+use deno_core::error::AnyError;
+use deno_core::serde_json;
+use deno_core::url::Url;
+use deno_core::FastString;
+use deno_core::ModuleSourceCode;
+use deno_core::ModuleType;
+use deno_npm::resolution::SerializedNpmResolutionSnapshot;
+use deno_npm::resolution::SerializedNpmResolutionSnapshotPackage;
+use deno_npm::resolution::ValidSerializedNpmResolutionSnapshot;
+use deno_npm::NpmPackageId;
+use deno_semver::package::PackageReq;
+
+use crate::standalone::virtual_fs::VirtualDirectory;
+
+use super::binary::Metadata;
+use super::virtual_fs::VfsBuilder;
+
+const MAGIC_BYTES: &[u8; 8] = b"d3n0l4nd";
+
+/// Binary format:
+/// * d3n0l4nd
+/// * <metadata_len><metadata>
+/// * <npm_snapshot_len><npm_snapshot>
+/// * <remote_modules_len><remote_modules>
+/// * <vfs_headers_len><vfs_headers>
+/// * <vfs_file_data_len><vfs_file_data>
+/// * d3n0l4nd
+pub fn serialize_binary_data_section(
+  metadata: &Metadata,
+  npm_snapshot: Option<SerializedNpmResolutionSnapshot>,
+  remote_modules: &RemoteModulesStoreBuilder,
+  vfs: VfsBuilder,
+) -> Result<Vec<u8>, AnyError> {
+  fn write_bytes_with_len(bytes: &mut Vec<u8>, data: &[u8]) {
+    bytes.extend_from_slice(&(data.len() as u64).to_le_bytes());
+    bytes.extend_from_slice(data);
+  }
+
+  let mut bytes = Vec::new();
+  bytes.extend_from_slice(MAGIC_BYTES);
+
+  // 1. Metadata
+  {
+    let metadata = serde_json::to_string(metadata)?;
+    write_bytes_with_len(&mut bytes, metadata.as_bytes());
+  }
+  // 2. Npm snapshot
+  {
+    let npm_snapshot =
+      npm_snapshot.map(serialize_npm_snapshot).unwrap_or_default();
+    write_bytes_with_len(&mut bytes, &npm_snapshot);
+  }
+  // 3. Remote modules
+  {
+    let update_index = bytes.len();
+    bytes.extend_from_slice(&(0_u64).to_le_bytes());
+    let start_index = bytes.len();
+    remote_modules.write(&mut bytes)?;
+    let length = bytes.len() - start_index;
+    let length_bytes = (length as u64).to_le_bytes();
+    bytes[update_index..update_index + length_bytes.len()]
+      .copy_from_slice(&length_bytes);
+  }
+  // 4. VFS
+  {
+    let (vfs, vfs_files) = vfs.into_dir_and_files();
+    let vfs = serde_json::to_string(&vfs)?;
+    write_bytes_with_len(&mut bytes, vfs.as_bytes());
+    let vfs_bytes_len = vfs_files.iter().map(|f| f.len() as u64).sum::<u64>();
+    bytes.extend_from_slice(&vfs_bytes_len.to_le_bytes());
+    for file in &vfs_files {
+      bytes.extend_from_slice(file);
+    }
+  }
+
+  // write the magic bytes at the end so we can use it
+  // to make sure we've deserialized correctly
+  bytes.extend_from_slice(MAGIC_BYTES);
+
+  Ok(bytes)
+}
+
+pub struct DeserializedDataSection {
+  pub metadata: Metadata,
+  pub npm_snapshot: Option<ValidSerializedNpmResolutionSnapshot>,
+  pub remote_modules: RemoteModulesStore,
+  pub vfs_dir: VirtualDirectory,
+  pub vfs_files_data: &'static [u8],
+}
+
+pub fn deserialize_binary_data_section(
+  data: &'static [u8],
+) -> Result<Option<DeserializedDataSection>, AnyError> {
+  fn read_bytes_with_len(input: &[u8]) -> Result<(&[u8], &[u8]), AnyError> {
+    let (input, len) = read_u64(input)?;
+    let (input, data) = read_bytes(input, len as usize)?;
+    Ok((input, data))
+  }
+
+  fn read_magic_bytes(input: &[u8]) -> Result<(&[u8], bool), AnyError> {
+    if input.len() < MAGIC_BYTES.len() {
+      bail!("Unexpected end of data. Could not find magic bytes.");
+    }
+    let (magic_bytes, input) = input.split_at(MAGIC_BYTES.len());
+    if magic_bytes != MAGIC_BYTES {
+      return Ok((input, false));
+    }
+    Ok((input, true))
+  }
+
+  let (input, found) = read_magic_bytes(data)?;
+  if !found {
+    return Ok(None);
+  }
+
+  // 1. Metadata
+  let (input, data) = read_bytes_with_len(input).context("reading metadata")?;
+  let metadata: Metadata =
+    serde_json::from_slice(data).context("deserializing metadata")?;
+  // 2. Npm snapshot
+  let (input, data) =
+    read_bytes_with_len(input).context("reading npm snapshot")?;
+  let npm_snapshot = if data.is_empty() {
+    None
+  } else {
+    Some(deserialize_npm_snapshot(data).context("deserializing npm snapshot")?)
+  };
+  // 3. Remote modules
+  let (input, data) =
+    read_bytes_with_len(input).context("reading remote modules data")?;
+  let remote_modules =
+    RemoteModulesStore::build(data).context("deserializing remote modules")?;
+  // 4. VFS
+  let (input, data) = read_bytes_with_len(input).context("vfs")?;
+  let vfs_dir: VirtualDirectory =
+    serde_json::from_slice(data).context("deserializing vfs data")?;
+  let (input, vfs_files_data) =
+    read_bytes_with_len(input).context("reading vfs files data")?;
+
+  // finally ensure we read the magic bytes at the end
+  let (_input, found) = read_magic_bytes(input)?;
+  if !found {
+    bail!("Could not find magic bytes at the end of the data.");
+  }
+
+  Ok(Some(DeserializedDataSection {
+    metadata,
+    npm_snapshot,
+    remote_modules,
+    vfs_dir,
+    vfs_files_data,
+  }))
+}
+
+#[derive(Default)]
+pub struct RemoteModulesStoreBuilder {
+  specifiers: Vec<(String, u64)>,
+  data: Vec<(MediaType, Vec<u8>)>,
+  data_byte_len: u64,
+  redirects: Vec<(String, String)>,
+  redirects_len: u64,
+}
+
+impl RemoteModulesStoreBuilder {
+  pub fn add(&mut self, specifier: &Url, media_type: MediaType, data: Vec<u8>) {
+    log::debug!("Adding '{}' ({})", specifier, media_type);
+    let specifier = specifier.to_string();
+    self.specifiers.push((specifier, self.data_byte_len));
+    self.data_byte_len += 1 + 8 + data.len() as u64; // media type (1 byte), data length (8 bytes), data
+    self.data.push((media_type, data));
+  }
+
+  pub fn add_redirects(&mut self, redirects: &BTreeMap<Url, Url>) {
+    self.redirects.reserve(redirects.len());
+    for (from, to) in redirects {
+      log::debug!("Adding redirect '{}' -> '{}'", from, to);
+      let from = from.to_string();
+      let to = to.to_string();
+      self.redirects_len += (4 + from.len() + 4 + to.len()) as u64;
+      self.redirects.push((from, to));
+    }
+  }
+
+  fn write(&self, writer: &mut dyn Write) -> Result<(), AnyError> {
+    writer.write_all(&(self.specifiers.len() as u32).to_le_bytes())?;
+    writer.write_all(&(self.redirects.len() as u32).to_le_bytes())?;
+    for (specifier, offset) in &self.specifiers {
+      writer.write_all(&(specifier.len() as u32).to_le_bytes())?;
+      writer.write_all(specifier.as_bytes())?;
+      writer.write_all(&offset.to_le_bytes())?;
+    }
+    for (from, to) in &self.redirects {
+      writer.write_all(&(from.len() as u32).to_le_bytes())?;
+      writer.write_all(from.as_bytes())?;
+      writer.write_all(&(to.len() as u32).to_le_bytes())?;
+      writer.write_all(to.as_bytes())?;
+    }
+    for (media_type, data) in &self.data {
+      writer.write_all(&[serialize_media_type(*media_type)])?;
+      writer.write_all(&(data.len() as u64).to_le_bytes())?;
+      writer.write_all(data)?;
+    }
+    Ok(())
+  }
+}
+
+pub enum DenoCompileModuleSource {
+  String(&'static str),
+  Bytes(Cow<'static, [u8]>),
+}
+
+impl DenoCompileModuleSource {
+  pub fn into_for_v8(self) -> ModuleSourceCode {
+    fn into_bytes(data: Cow<'static, [u8]>) -> ModuleSourceCode {
+      ModuleSourceCode::Bytes(match data {
+        Cow::Borrowed(d) => d.into(),
+        Cow::Owned(d) => d.into_boxed_slice().into(),
+      })
+    }
+
+    match self {
+      // todo(https://github.com/denoland/deno_core/pull/943): store whether
+      // the string is ascii or not ahead of time so we can avoid the is_ascii()
+      // check in FastString::from_static
+      Self::String(s) => ModuleSourceCode::String(FastString::from_static(s)),
+      Self::Bytes(b) => into_bytes(b),
+    }
+  }
+}
+
+pub struct DenoCompileModuleData<'a> {
+  pub specifier: &'a Url,
+  pub media_type: MediaType,
+  pub data: Cow<'static, [u8]>,
+}
+
+impl<'a> DenoCompileModuleData<'a> {
+  pub fn into_parts(self) -> (&'a Url, ModuleType, DenoCompileModuleSource) {
+    fn into_string_unsafe(data: Cow<'static, [u8]>) -> DenoCompileModuleSource {
+      match data {
+        Cow::Borrowed(d) => DenoCompileModuleSource::String(
+          // SAFETY: we know this is a valid utf8 string
+          unsafe { std::str::from_utf8_unchecked(d) },
+        ),
+        Cow::Owned(d) => DenoCompileModuleSource::Bytes(Cow::Owned(d)),
+      }
+    }
+
+    let (media_type, source) = match self.media_type {
+      MediaType::JavaScript
+      | MediaType::Jsx
+      | MediaType::Mjs
+      | MediaType::Cjs
+      | MediaType::TypeScript
+      | MediaType::Mts
+      | MediaType::Cts
+      | MediaType::Dts
+      | MediaType::Dmts
+      | MediaType::Dcts
+      | MediaType::Tsx => {
+        (ModuleType::JavaScript, into_string_unsafe(self.data))
+      }
+      MediaType::Json => (ModuleType::Json, into_string_unsafe(self.data)),
+      MediaType::Wasm => {
+        (ModuleType::Wasm, DenoCompileModuleSource::Bytes(self.data))
+      }
+      // just assume javascript if we made it here
+      MediaType::Css | MediaType::SourceMap | MediaType::Unknown => (
+        ModuleType::JavaScript,
+        DenoCompileModuleSource::Bytes(self.data),
+      ),
+    };
+    (self.specifier, media_type, source)
+  }
+}
+
+enum RemoteModulesStoreSpecifierValue {
+  Data(usize),
+  Redirect(Url),
+}
+
+pub struct RemoteModulesStore {
+  specifiers: HashMap<Url, RemoteModulesStoreSpecifierValue>,
+  files_data: &'static [u8],
+}
+
+impl RemoteModulesStore {
+  fn build(data: &'static [u8]) -> Result<Self, AnyError> {
+    fn read_specifier(input: &[u8]) -> Result<(&[u8], (Url, u64)), AnyError> {
+      let (input, specifier) = read_string_lossy(input)?;
+      let specifier = Url::parse(&specifier)?;
+      let (input, offset) = read_u64(input)?;
+      Ok((input, (specifier, offset)))
+    }
+
+    fn read_redirect(input: &[u8]) -> Result<(&[u8], (Url, Url)), AnyError> {
+      let (input, from) = read_string_lossy(input)?;
+      let from = Url::parse(&from)?;
+      let (input, to) = read_string_lossy(input)?;
+      let to = Url::parse(&to)?;
+      Ok((input, (from, to)))
+    }
+
+    fn read_headers(
+      input: &[u8],
+    ) -> Result<(&[u8], HashMap<Url, RemoteModulesStoreSpecifierValue>), AnyError>
+    {
+      let (input, specifiers_len) = read_u32_as_usize(input)?;
+      let (mut input, redirects_len) = read_u32_as_usize(input)?;
+      let mut specifiers =
+        HashMap::with_capacity(specifiers_len + redirects_len);
+      for _ in 0..specifiers_len {
+        let (current_input, (specifier, offset)) =
+          read_specifier(input).context("reading specifier")?;
+        input = current_input;
+        specifiers.insert(
+          specifier,
+          RemoteModulesStoreSpecifierValue::Data(offset as usize),
+        );
+      }
+
+      for _ in 0..redirects_len {
+        let (current_input, (from, to)) = read_redirect(input)?;
+        input = current_input;
+        specifiers.insert(from, RemoteModulesStoreSpecifierValue::Redirect(to));
+      }
+
+      Ok((input, specifiers))
+    }
+
+    let (files_data, specifiers) = read_headers(data)?;
+
+    Ok(Self {
+      specifiers,
+      files_data,
+    })
+  }
+
+  pub fn resolve_specifier<'a>(
+    &'a self,
+    specifier: &'a Url,
+  ) -> Result<Option<&'a Url>, AnyError> {
+    let mut count = 0;
+    let mut current = specifier;
+    loop {
+      if count > 10 {
+        bail!("Too many redirects resolving '{}'", specifier);
+      }
+      match self.specifiers.get(current) {
+        Some(RemoteModulesStoreSpecifierValue::Redirect(to)) => {
+          current = to;
+          count += 1;
+        }
+        Some(RemoteModulesStoreSpecifierValue::Data(_)) => {
+          return Ok(Some(current));
+        }
+        None => {
+          return Ok(None);
+        }
+      }
+    }
+  }
+
+  pub fn read<'a>(
+    &'a self,
+    original_specifier: &'a Url,
+  ) -> Result<Option<DenoCompileModuleData<'a>>, AnyError> {
+    let mut count = 0;
+    let mut specifier = original_specifier;
+    loop {
+      if count > 10 {
+        bail!("Too many redirects resolving '{}'", original_specifier);
+      }
+      match self.specifiers.get(specifier) {
+        Some(RemoteModulesStoreSpecifierValue::Redirect(to)) => {
+          specifier = to;
+          count += 1;
+        }
+        Some(RemoteModulesStoreSpecifierValue::Data(offset)) => {
+          let input = &self.files_data[*offset..];
+          let (input, media_type_byte) = read_bytes(input, 1)?;
+          let media_type = deserialize_media_type(media_type_byte[0])?;
+          let (input, len) = read_u64(input)?;
+          let (_input, data) = read_bytes(input, len as usize)?;
+          return Ok(Some(DenoCompileModuleData {
+            specifier,
+            media_type,
+            data: Cow::Borrowed(data),
+          }));
+        }
+        None => {
+          return Ok(None);
+        }
+      }
+    }
+  }
+}
+
+fn serialize_npm_snapshot(
+  mut snapshot: SerializedNpmResolutionSnapshot,
+) -> Vec<u8> {
+  fn append_string(bytes: &mut Vec<u8>, string: &str) {
+    let len = string.len() as u32;
+    bytes.extend_from_slice(&len.to_le_bytes());
+    bytes.extend_from_slice(string.as_bytes());
+  }
+
+  snapshot.packages.sort_by(|a, b| a.id.cmp(&b.id)); // determinism
+  let ids_to_stored_ids = snapshot
+    .packages
+    .iter()
+    .enumerate()
+    .map(|(i, pkg)| (&pkg.id, i as u32))
+    .collect::<HashMap<_, _>>();
+
+  let mut root_packages: Vec<_> = snapshot.root_packages.iter().collect();
+  root_packages.sort();
+  let mut bytes = Vec::new();
+
+  bytes.extend_from_slice(&(snapshot.packages.len() as u32).to_le_bytes());
+  for pkg in &snapshot.packages {
+    append_string(&mut bytes, &pkg.id.as_serialized());
+  }
+
+  bytes.extend_from_slice(&(root_packages.len() as u32).to_le_bytes());
+  for (req, id) in root_packages {
+    append_string(&mut bytes, &req.to_string());
+    let id = ids_to_stored_ids.get(&id).unwrap();
+    bytes.extend_from_slice(&id.to_le_bytes());
+  }
+
+  for pkg in &snapshot.packages {
+    let deps_len = pkg.dependencies.len() as u32;
+    bytes.extend_from_slice(&deps_len.to_le_bytes());
+    let mut deps: Vec<_> = pkg.dependencies.iter().collect();
+    deps.sort();
+    for (req, id) in deps {
+      append_string(&mut bytes, req);
+      let id = ids_to_stored_ids.get(&id).unwrap();
+      bytes.extend_from_slice(&id.to_le_bytes());
+    }
+  }
+
+  bytes
+}
+
+fn deserialize_npm_snapshot(
+  input: &[u8],
+) -> Result<ValidSerializedNpmResolutionSnapshot, AnyError> {
+  fn parse_id(input: &[u8]) -> Result<(&[u8], NpmPackageId), AnyError> {
+    let (input, id) = read_string_lossy(input)?;
+    let id = NpmPackageId::from_serialized(&id)?;
+    Ok((input, id))
+  }
+
+  #[allow(clippy::needless_lifetimes)] // clippy bug
+  fn parse_root_package<'a>(
+    id_to_npm_id: &'a impl Fn(usize) -> Result<NpmPackageId, AnyError>,
+  ) -> impl Fn(&[u8]) -> Result<(&[u8], (PackageReq, NpmPackageId)), AnyError> + 'a
+  {
+    |input| {
+      let (input, req) = read_string_lossy(input)?;
+      let req = PackageReq::from_str(&req)?;
+      let (input, id) = read_u32_as_usize(input)?;
+      Ok((input, (req, id_to_npm_id(id)?)))
+    }
+  }
+
+  #[allow(clippy::needless_lifetimes)] // clippy bug
+  fn parse_package_dep<'a>(
+    id_to_npm_id: &'a impl Fn(usize) -> Result<NpmPackageId, AnyError>,
+  ) -> impl Fn(&[u8]) -> Result<(&[u8], (String, NpmPackageId)), AnyError> + 'a
+  {
+    |input| {
+      let (input, req) = read_string_lossy(input)?;
+      let (input, id) = read_u32_as_usize(input)?;
+      Ok((input, (req.into_owned(), id_to_npm_id(id)?)))
+    }
+  }
+
+  fn parse_package<'a>(
+    input: &'a [u8],
+    id: NpmPackageId,
+    id_to_npm_id: &impl Fn(usize) -> Result<NpmPackageId, AnyError>,
+  ) -> Result<(&'a [u8], SerializedNpmResolutionSnapshotPackage), AnyError> {
+    let (input, deps_len) = read_u32_as_usize(input)?;
+    let (input, dependencies) =
+      parse_hashmap_n_times(input, deps_len, parse_package_dep(id_to_npm_id))?;
+    Ok((
+      input,
+      SerializedNpmResolutionSnapshotPackage {
+        id,
+        system: Default::default(),
+        dist: Default::default(),
+        dependencies,
+        optional_dependencies: Default::default(),
+        bin: None,
+        scripts: Default::default(),
+        deprecated: Default::default(),
+      },
+    ))
+  }
+
+  let (input, packages_len) = read_u32_as_usize(input)?;
+
+  // get a hashmap of all the npm package ids to their serialized ids
+  let (input, data_ids_to_npm_ids) =
+    parse_vec_n_times(input, packages_len, parse_id)
+      .context("deserializing id")?;
+  let data_id_to_npm_id = |id: usize| {
+    data_ids_to_npm_ids
+      .get(id)
+      .cloned()
+      .ok_or_else(|| deno_core::anyhow::anyhow!("Invalid npm package id"))
+  };
+
+  let (input, root_packages_len) = read_u32_as_usize(input)?;
+  let (input, root_packages) = parse_hashmap_n_times(
+    input,
+    root_packages_len,
+    parse_root_package(&data_id_to_npm_id),
+  )
+  .context("deserializing root package")?;
+  let (input, packages) =
+    parse_vec_n_times_with_index(input, packages_len, |input, index| {
+      parse_package(input, data_id_to_npm_id(index)?, &data_id_to_npm_id)
+    })
+    .context("deserializing package")?;
+
+  if !input.is_empty() {
+    bail!("Unexpected data left over");
+  }
+
+  Ok(
+    SerializedNpmResolutionSnapshot {
+      packages,
+      root_packages,
+    }
+    // this is ok because we have already verified that all the
+    // identifiers found in the snapshot are valid via the
+    // npm package id -> npm package id mapping
+    .into_valid_unsafe(),
+  )
+}
+
+fn serialize_media_type(media_type: MediaType) -> u8 {
+  match media_type {
+    MediaType::JavaScript => 0,
+    MediaType::Jsx => 1,
+    MediaType::Mjs => 2,
+    MediaType::Cjs => 3,
+    MediaType::TypeScript => 4,
+    MediaType::Mts => 5,
+    MediaType::Cts => 6,
+    MediaType::Dts => 7,
+    MediaType::Dmts => 8,
+    MediaType::Dcts => 9,
+    MediaType::Tsx => 10,
+    MediaType::Json => 11,
+    MediaType::Wasm => 12,
+    MediaType::Css => 13,
+    MediaType::SourceMap => 14,
+    MediaType::Unknown => 15,
+  }
+}
+
+fn deserialize_media_type(value: u8) -> Result<MediaType, AnyError> {
+  match value {
+    0 => Ok(MediaType::JavaScript),
+    1 => Ok(MediaType::Jsx),
+    2 => Ok(MediaType::Mjs),
+    3 => Ok(MediaType::Cjs),
+    4 => Ok(MediaType::TypeScript),
+    5 => Ok(MediaType::Mts),
+    6 => Ok(MediaType::Cts),
+    7 => Ok(MediaType::Dts),
+    8 => Ok(MediaType::Dmts),
+    9 => Ok(MediaType::Dcts),
+    10 => Ok(MediaType::Tsx),
+    11 => Ok(MediaType::Json),
+    12 => Ok(MediaType::Wasm),
+    13 => Ok(MediaType::Css),
+    14 => Ok(MediaType::SourceMap),
+    15 => Ok(MediaType::Unknown),
+    _ => bail!("Unknown media type value: {}", value),
+  }
+}
+
+fn parse_hashmap_n_times<TKey: std::cmp::Eq + std::hash::Hash, TValue>(
+  mut input: &[u8],
+  times: usize,
+  parse: impl Fn(&[u8]) -> Result<(&[u8], (TKey, TValue)), AnyError>,
+) -> Result<(&[u8], HashMap<TKey, TValue>), AnyError> {
+  let mut results = HashMap::with_capacity(times);
+  for _ in 0..times {
+    let result = parse(input);
+    let (new_input, (key, value)) = result?;
+    results.insert(key, value);
+    input = new_input;
+  }
+  Ok((input, results))
+}
+
+fn parse_vec_n_times<TResult>(
+  input: &[u8],
+  times: usize,
+  parse: impl Fn(&[u8]) -> Result<(&[u8], TResult), AnyError>,
+) -> Result<(&[u8], Vec<TResult>), AnyError> {
+  parse_vec_n_times_with_index(input, times, |input, _index| parse(input))
+}
+
+fn parse_vec_n_times_with_index<TResult>(
+  mut input: &[u8],
+  times: usize,
+  parse: impl Fn(&[u8], usize) -> Result<(&[u8], TResult), AnyError>,
+) -> Result<(&[u8], Vec<TResult>), AnyError> {
+  let mut results = Vec::with_capacity(times);
+  for i in 0..times {
+    let result = parse(input, i);
+    let (new_input, result) = result?;
+    results.push(result);
+    input = new_input;
+  }
+  Ok((input, results))
+}
+
+fn read_bytes(input: &[u8], len: usize) -> Result<(&[u8], &[u8]), AnyError> {
+  if input.len() < len {
+    bail!("Unexpected end of data.",);
+  }
+  let (len_bytes, input) = input.split_at(len);
+  Ok((input, len_bytes))
+}
+
+fn read_string_lossy(input: &[u8]) -> Result<(&[u8], Cow<str>), AnyError> {
+  let (input, str_len) = read_u32_as_usize(input)?;
+  let (input, data_bytes) = read_bytes(input, str_len)?;
+  Ok((input, String::from_utf8_lossy(data_bytes)))
+}
+
+fn read_u32_as_usize(input: &[u8]) -> Result<(&[u8], usize), AnyError> {
+  let (input, len_bytes) = read_bytes(input, 4)?;
+  let len = u32::from_le_bytes(len_bytes.try_into()?);
+  Ok((input, len as usize))
+}
+
+fn read_u64(input: &[u8]) -> Result<(&[u8], u64), AnyError> {
+  let (input, len_bytes) = read_bytes(input, 8)?;
+  let len = u64::from_le_bytes(len_bytes.try_into()?);
+  Ok((input, len))
+}
diff --git a/cli/standalone/virtual_fs.rs b/cli/standalone/virtual_fs.rs
index 53d045b625..26bb0db75f 100644
--- a/cli/standalone/virtual_fs.rs
+++ b/cli/standalone/virtual_fs.rs
@@ -7,6 +7,7 @@ use std::fs::File;
 use std::io::Read;
 use std::io::Seek;
 use std::io::SeekFrom;
+use std::ops::Range;
 use std::path::Path;
 use std::path::PathBuf;
 use std::rc::Rc;
@@ -67,6 +68,26 @@ impl VfsBuilder {
     })
   }
 
+  pub fn set_new_root_path(
+    &mut self,
+    root_path: PathBuf,
+  ) -> Result<(), AnyError> {
+    let root_path = canonicalize_path(&root_path)?;
+    self.root_path = root_path;
+    self.root_dir = VirtualDirectory {
+      name: self
+        .root_path
+        .file_stem()
+        .map(|s| s.to_string_lossy().into_owned())
+        .unwrap_or("root".to_string()),
+      entries: vec![VfsEntry::Dir(VirtualDirectory {
+        name: std::mem::take(&mut self.root_dir.name),
+        entries: std::mem::take(&mut self.root_dir.entries),
+      })],
+    };
+    Ok(())
+  }
+
   pub fn with_root_dir<R>(
     &mut self,
     with_root: impl FnOnce(&mut VirtualDirectory) -> R,
@@ -119,7 +140,7 @@ impl VfsBuilder {
                 // inline the symlink and make the target file
                 let file_bytes = std::fs::read(&target)
                   .with_context(|| format!("Reading {}", path.display()))?;
-                self.add_file(&path, file_bytes)?;
+                self.add_file_with_data_inner(&path, file_bytes)?;
               } else {
                 log::warn!(
                   "{} Symlink target is outside '{}'. Excluding symlink at '{}' with target '{}'.",
@@ -191,16 +212,32 @@ impl VfsBuilder {
     self.add_file_at_path_not_symlink(&target_path)
   }
 
-  pub fn add_file_at_path_not_symlink(
+  fn add_file_at_path_not_symlink(
     &mut self,
     path: &Path,
   ) -> Result<(), AnyError> {
     let file_bytes = std::fs::read(path)
       .with_context(|| format!("Reading {}", path.display()))?;
-    self.add_file(path, file_bytes)
+    self.add_file_with_data_inner(path, file_bytes)
   }
 
-  fn add_file(&mut self, path: &Path, data: Vec<u8>) -> Result<(), AnyError> {
+  pub fn add_file_with_data(
+    &mut self,
+    path: &Path,
+    data: Vec<u8>,
+  ) -> Result<(), AnyError> {
+    let target_path = canonicalize_path(path)?;
+    if target_path != path {
+      self.add_symlink(path, &target_path)?;
+    }
+    self.add_file_with_data_inner(&target_path, data)
+  }
+
+  fn add_file_with_data_inner(
+    &mut self,
+    path: &Path,
+    data: Vec<u8>,
+  ) -> Result<(), AnyError> {
     log::debug!("Adding file '{}'", path.display());
     let checksum = util::checksum::gen(&[&data]);
     let offset = if let Some(offset) = self.file_offsets.get(&checksum) {
@@ -249,8 +286,15 @@ impl VfsBuilder {
       path.display(),
       target.display()
     );
-    let dest = self.path_relative_root(target)?;
-    if dest == self.path_relative_root(path)? {
+    let relative_target = self.path_relative_root(target)?;
+    let relative_path = match self.path_relative_root(path) {
+      Ok(path) => path,
+      Err(StripRootError { .. }) => {
+        // ignore if the original path is outside the root directory
+        return Ok(());
+      }
+    };
+    if relative_target == relative_path {
       // it's the same, ignore
       return Ok(());
     }
@@ -263,7 +307,7 @@ impl VfsBuilder {
           insert_index,
           VfsEntry::Symlink(VirtualSymlink {
             name: name.to_string(),
-            dest_parts: dest
+            dest_parts: relative_target
               .components()
               .map(|c| c.as_os_str().to_string_lossy().to_string())
               .collect::<Vec<_>>(),
@@ -306,6 +350,7 @@ impl<'a> VfsEntryRef<'a> {
         atime: None,
         birthtime: None,
         mtime: None,
+        ctime: None,
         blksize: 0,
         size: 0,
         dev: 0,
@@ -328,6 +373,7 @@ impl<'a> VfsEntryRef<'a> {
         atime: None,
         birthtime: None,
         mtime: None,
+        ctime: None,
         blksize: 0,
         size: file.len,
         dev: 0,
@@ -350,6 +396,7 @@ impl<'a> VfsEntryRef<'a> {
         atime: None,
         birthtime: None,
         mtime: None,
+        ctime: None,
         blksize: 0,
         size: 0,
         dev: 0,
@@ -751,14 +798,14 @@ impl deno_io::fs::File for FileBackedVfsFile {
 
 #[derive(Debug)]
 pub struct FileBackedVfs {
-  file: Mutex<Vec<u8>>,
+  vfs_data: Cow<'static, [u8]>,
   fs_root: VfsRoot,
 }
 
 impl FileBackedVfs {
-  pub fn new(file: Vec<u8>, fs_root: VfsRoot) -> Self {
+  pub fn new(data: Cow<'static, [u8]>, fs_root: VfsRoot) -> Self {
     Self {
-      file: Mutex::new(file),
+      vfs_data: data,
       fs_root,
     }
   }
@@ -827,10 +874,15 @@ impl FileBackedVfs {
     Ok(path)
   }
 
-  pub fn read_file_all(&self, file: &VirtualFile) -> std::io::Result<Vec<u8>> {
-    let mut buf = vec![0; file.len as usize];
-    self.read_file(file, 0, &mut buf)?;
-    Ok(buf)
+  pub fn read_file_all(
+    &self,
+    file: &VirtualFile,
+  ) -> std::io::Result<Cow<'static, [u8]>> {
+    let read_range = self.get_read_range(file, 0, file.len)?;
+    match &self.vfs_data {
+      Cow::Borrowed(data) => Ok(Cow::Borrowed(&data[read_range])),
+      Cow::Owned(data) => Ok(Cow::Owned(data[read_range].to_vec())),
+    }
   }
 
   pub fn read_file(
@@ -839,18 +891,27 @@ impl FileBackedVfs {
     pos: u64,
     buf: &mut [u8],
   ) -> std::io::Result<usize> {
-    let data = self.file.lock();
+    let read_range = self.get_read_range(file, pos, buf.len() as u64)?;
+    buf.copy_from_slice(&self.vfs_data[read_range]);
+    Ok(buf.len())
+  }
+
+  fn get_read_range(
+    &self,
+    file: &VirtualFile,
+    pos: u64,
+    len: u64,
+  ) -> std::io::Result<Range<usize>> {
+    let data = &self.vfs_data;
     let start = self.fs_root.start_file_offset + file.offset + pos;
-    let end = start + buf.len() as u64;
+    let end = start + len;
     if end > data.len() as u64 {
       return Err(std::io::Error::new(
         std::io::ErrorKind::UnexpectedEof,
         "unexpected EOF",
       ));
     }
-
-    buf.copy_from_slice(&data[start as usize..end as usize]);
-    Ok(buf.len())
+    Ok(start as usize..end as usize)
   }
 
   pub fn dir_entry(&self, path: &Path) -> std::io::Result<&VirtualDirectory> {
@@ -888,7 +949,7 @@ mod test {
   #[track_caller]
   fn read_file(vfs: &FileBackedVfs, path: &Path) -> String {
     let file = vfs.file_entry(path).unwrap();
-    String::from_utf8(vfs.read_file_all(file).unwrap()).unwrap()
+    String::from_utf8(vfs.read_file_all(file).unwrap().into_owned()).unwrap()
   }
 
   #[test]
@@ -901,20 +962,23 @@ mod test {
     let src_path = src_path.to_path_buf();
     let mut builder = VfsBuilder::new(src_path.clone()).unwrap();
     builder
-      .add_file(&src_path.join("a.txt"), "data".into())
+      .add_file_with_data_inner(&src_path.join("a.txt"), "data".into())
       .unwrap();
     builder
-      .add_file(&src_path.join("b.txt"), "data".into())
+      .add_file_with_data_inner(&src_path.join("b.txt"), "data".into())
       .unwrap();
     assert_eq!(builder.files.len(), 1); // because duplicate data
     builder
-      .add_file(&src_path.join("c.txt"), "c".into())
+      .add_file_with_data_inner(&src_path.join("c.txt"), "c".into())
       .unwrap();
     builder
-      .add_file(&src_path.join("sub_dir").join("d.txt"), "d".into())
+      .add_file_with_data_inner(
+        &src_path.join("sub_dir").join("d.txt"),
+        "d".into(),
+      )
       .unwrap();
     builder
-      .add_file(&src_path.join("e.txt"), "e".into())
+      .add_file_with_data_inner(&src_path.join("e.txt"), "e".into())
       .unwrap();
     builder
       .add_symlink(
@@ -1031,7 +1095,7 @@ mod test {
     (
       dest_path.to_path_buf(),
       FileBackedVfs::new(
-        data,
+        Cow::Owned(data),
         VfsRoot {
           dir: root_dir,
           root_path: dest_path.to_path_buf(),
@@ -1082,7 +1146,7 @@ mod test {
     let temp_path = temp_dir.path().canonicalize();
     let mut builder = VfsBuilder::new(temp_path.to_path_buf()).unwrap();
     builder
-      .add_file(
+      .add_file_with_data_inner(
         temp_path.join("a.txt").as_path(),
         "0123456789".to_string().into_bytes(),
       )
diff --git a/cli/task_runner.rs b/cli/task_runner.rs
index ab7163bc93..43840e868d 100644
--- a/cli/task_runner.rs
+++ b/cli/task_runner.rs
@@ -16,8 +16,11 @@ use deno_task_shell::ExecutableCommand;
 use deno_task_shell::ExecuteResult;
 use deno_task_shell::ShellCommand;
 use deno_task_shell::ShellCommandContext;
+use deno_task_shell::ShellPipeReader;
+use deno_task_shell::ShellPipeWriter;
 use lazy_regex::Lazy;
 use regex::Regex;
+use tokio::task::JoinHandle;
 use tokio::task::LocalSet;
 
 use crate::npm::CliNpmResolver;
@@ -36,6 +39,35 @@ pub fn get_script_with_args(script: &str, argv: &[String]) -> String {
   script.trim().to_owned()
 }
 
+pub struct TaskStdio(Option<ShellPipeReader>, ShellPipeWriter);
+
+impl TaskStdio {
+  pub fn stdout() -> Self {
+    Self(None, ShellPipeWriter::stdout())
+  }
+  pub fn stderr() -> Self {
+    Self(None, ShellPipeWriter::stderr())
+  }
+  pub fn piped() -> Self {
+    let (r, w) = deno_task_shell::pipe();
+    Self(Some(r), w)
+  }
+}
+
+pub struct TaskIo {
+  pub stdout: TaskStdio,
+  pub stderr: TaskStdio,
+}
+
+impl Default for TaskIo {
+  fn default() -> Self {
+    Self {
+      stderr: TaskStdio::stderr(),
+      stdout: TaskStdio::stdout(),
+    }
+  }
+}
+
 pub struct RunTaskOptions<'a> {
   pub task_name: &'a str,
   pub script: &'a str,
@@ -45,24 +77,69 @@ pub struct RunTaskOptions<'a> {
   pub argv: &'a [String],
   pub custom_commands: HashMap<String, Rc<dyn ShellCommand>>,
   pub root_node_modules_dir: Option<&'a Path>,
+  pub stdio: Option<TaskIo>,
 }
 
 pub type TaskCustomCommands = HashMap<String, Rc<dyn ShellCommand>>;
 
-pub async fn run_task(opts: RunTaskOptions<'_>) -> Result<i32, AnyError> {
+pub struct TaskResult {
+  pub exit_code: i32,
+  pub stdout: Option<Vec<u8>>,
+  pub stderr: Option<Vec<u8>>,
+}
+
+pub async fn run_task(
+  opts: RunTaskOptions<'_>,
+) -> Result<TaskResult, AnyError> {
   let script = get_script_with_args(opts.script, opts.argv);
   let seq_list = deno_task_shell::parser::parse(&script)
     .with_context(|| format!("Error parsing script '{}'.", opts.task_name))?;
   let env_vars =
     prepare_env_vars(opts.env_vars, opts.init_cwd, opts.root_node_modules_dir);
+  let state =
+    deno_task_shell::ShellState::new(env_vars, opts.cwd, opts.custom_commands);
+  let stdio = opts.stdio.unwrap_or_default();
+  let (
+    TaskStdio(stdout_read, stdout_write),
+    TaskStdio(stderr_read, stderr_write),
+  ) = (stdio.stdout, stdio.stderr);
+
+  fn read(reader: ShellPipeReader) -> JoinHandle<Result<Vec<u8>, AnyError>> {
+    tokio::task::spawn_blocking(move || {
+      let mut buf = Vec::new();
+      reader.pipe_to(&mut buf)?;
+      Ok(buf)
+    })
+  }
+
+  let stdout = stdout_read.map(read);
+  let stderr = stderr_read.map(read);
+
   let local = LocalSet::new();
-  let future = deno_task_shell::execute(
-    seq_list,
-    env_vars,
-    opts.cwd,
-    opts.custom_commands,
-  );
-  Ok(local.run_until(future).await)
+  let future = async move {
+    let exit_code = deno_task_shell::execute_with_pipes(
+      seq_list,
+      state,
+      ShellPipeReader::stdin(),
+      stdout_write,
+      stderr_write,
+    )
+    .await;
+    Ok::<_, AnyError>(TaskResult {
+      exit_code,
+      stdout: if let Some(stdout) = stdout {
+        Some(stdout.await??)
+      } else {
+        None
+      },
+      stderr: if let Some(stderr) = stderr {
+        Some(stderr.await??)
+      } else {
+        None
+      },
+    })
+  };
+  local.run_until(future).await
 }
 
 fn prepare_env_vars(
@@ -78,6 +155,12 @@ fn prepare_env_vars(
       initial_cwd.to_string_lossy().to_string(),
     );
   }
+  if !env_vars.contains_key(crate::npm::NPM_CONFIG_USER_AGENT_ENV_VAR) {
+    env_vars.insert(
+      crate::npm::NPM_CONFIG_USER_AGENT_ENV_VAR.into(),
+      crate::npm::get_npm_config_user_agent(),
+    );
+  }
   if let Some(node_modules_dir) = node_modules_dir {
     prepend_to_path(
       &mut env_vars,
@@ -127,7 +210,7 @@ impl ShellCommand for NpmCommand {
     mut context: ShellCommandContext,
   ) -> LocalBoxFuture<'static, ExecuteResult> {
     if context.args.first().map(|s| s.as_str()) == Some("run")
-      && context.args.len() > 2
+      && context.args.len() >= 2
       // for now, don't run any npm scripts that have a flag because
       // we don't handle stuff like `--workspaces` properly
       && !context.args.iter().any(|s| s.starts_with('-'))
@@ -190,10 +273,12 @@ impl ShellCommand for NodeCommand {
       )
       .execute(context);
     }
+
     args.extend(["run", "-A"].into_iter().map(|s| s.to_string()));
     args.extend(context.args.iter().cloned());
 
     let mut state = context.state;
+
     state.apply_env_var(USE_PKG_JSON_HIDDEN_ENV_VAR_NAME, "1");
     ExecutableCommand::new("deno".to_string(), std::env::current_exe().unwrap())
       .execute(ShellCommandContext {
diff --git a/cli/tools/bench/mod.rs b/cli/tools/bench/mod.rs
index be5d0ad0e1..272d063355 100644
--- a/cli/tools/bench/mod.rs
+++ b/cli/tools/bench/mod.rs
@@ -193,7 +193,7 @@ async fn bench_specifier_inner(
     .await?;
 
   // We execute the main module as a side module so that import.meta.main is not set.
-  worker.execute_side_module_possibly_with_npm().await?;
+  worker.execute_side_module().await?;
 
   let mut worker = worker.into_main_worker();
 
diff --git a/cli/tools/check.rs b/cli/tools/check.rs
index 7edb392d48..d880278884 100644
--- a/cli/tools/check.rs
+++ b/cli/tools/check.rs
@@ -32,6 +32,7 @@ use crate::graph_util::ModuleGraphBuilder;
 use crate::npm::CliNpmResolver;
 use crate::tsc;
 use crate::tsc::Diagnostics;
+use crate::tsc::TypeCheckingCjsTracker;
 use crate::util::extract;
 use crate::util::path::to_percent_decoded_str;
 
@@ -99,6 +100,7 @@ pub struct CheckOptions {
 
 pub struct TypeChecker {
   caches: Arc<Caches>,
+  cjs_tracker: Arc<TypeCheckingCjsTracker>,
   cli_options: Arc<CliOptions>,
   module_graph_builder: Arc<ModuleGraphBuilder>,
   node_resolver: Arc<NodeResolver>,
@@ -108,6 +110,7 @@ pub struct TypeChecker {
 impl TypeChecker {
   pub fn new(
     caches: Arc<Caches>,
+    cjs_tracker: Arc<TypeCheckingCjsTracker>,
     cli_options: Arc<CliOptions>,
     module_graph_builder: Arc<ModuleGraphBuilder>,
     node_resolver: Arc<NodeResolver>,
@@ -115,6 +118,7 @@ impl TypeChecker {
   ) -> Self {
     Self {
       caches,
+      cjs_tracker,
       cli_options,
       module_graph_builder,
       node_resolver,
@@ -244,6 +248,7 @@ impl TypeChecker {
       graph: graph.clone(),
       hash_data,
       maybe_npm: Some(tsc::RequestNpmState {
+        cjs_tracker: self.cjs_tracker.clone(),
         node_resolver: self.node_resolver.clone(),
         npm_resolver: self.npm_resolver.clone(),
       }),
@@ -346,7 +351,7 @@ fn get_check_hash(
             }
           }
           MediaType::Json
-          | MediaType::TsBuildInfo
+          | MediaType::Css
           | MediaType::SourceMap
           | MediaType::Wasm
           | MediaType::Unknown => continue,
@@ -428,7 +433,7 @@ fn get_tsc_roots(
         }
         MediaType::Json
         | MediaType::Wasm
-        | MediaType::TsBuildInfo
+        | MediaType::Css
         | MediaType::SourceMap
         | MediaType::Unknown => None,
       },
@@ -536,7 +541,7 @@ fn has_ts_check(media_type: MediaType, file_text: &str) -> bool {
     | MediaType::Tsx
     | MediaType::Json
     | MediaType::Wasm
-    | MediaType::TsBuildInfo
+    | MediaType::Css
     | MediaType::SourceMap
     | MediaType::Unknown => false,
   }
diff --git a/cli/tools/compile.rs b/cli/tools/compile.rs
index c1f98bc08a..b3e9993379 100644
--- a/cli/tools/compile.rs
+++ b/cli/tools/compile.rs
@@ -5,6 +5,7 @@ use crate::args::CompileFlags;
 use crate::args::Flags;
 use crate::factory::CliFactory;
 use crate::http_util::HttpClientProvider;
+use crate::standalone::binary::StandaloneRelativeFileBaseUrl;
 use crate::standalone::is_standalone_binary;
 use deno_ast::ModuleSpecifier;
 use deno_core::anyhow::bail;
@@ -14,7 +15,6 @@ use deno_core::error::AnyError;
 use deno_core::resolve_url_or_path;
 use deno_graph::GraphKind;
 use deno_terminal::colors;
-use eszip::EszipRelativeFileBaseUrl;
 use rand::Rng;
 use std::path::Path;
 use std::path::PathBuf;
@@ -29,7 +29,6 @@ pub async fn compile(
   let factory = CliFactory::from_flags(flags);
   let cli_options = factory.cli_options()?;
   let module_graph_creator = factory.module_graph_creator().await?;
-  let parsed_source_cache = factory.parsed_source_cache();
   let binary_writer = factory.create_compile_binary_writer().await?;
   let http_client = factory.http_client_provider();
   let module_specifier = cli_options.resolve_main_module()?;
@@ -70,7 +69,7 @@ pub async fn compile(
   let graph = if cli_options.type_check_mode().is_true() {
     // In this case, the previous graph creation did type checking, which will
     // create a module graph with types information in it. We don't want to
-    // store that in the eszip so create a code only module graph from scratch.
+    // store that in the binary so create a code only module graph from scratch.
     module_graph_creator
       .create_graph(GraphKind::CodeOnly, module_roots)
       .await?
@@ -81,11 +80,6 @@ pub async fn compile(
   let ts_config_for_emit = cli_options
     .resolve_ts_config_for_emit(deno_config::deno_json::TsConfigType::Emit)?;
   check_warn_tsconfig(&ts_config_for_emit);
-  let (transpile_options, emit_options) =
-    crate::args::ts_config_to_transpile_and_emit_options(
-      ts_config_for_emit.ts_config,
-    )?;
-  let parser = parsed_source_cache.as_capturing_parser();
   let root_dir_url = resolve_root_dir_from_specifiers(
     cli_options.workspace().root_dir(),
     graph.specifiers().map(|(s, _)| s).chain(
@@ -96,17 +90,6 @@ pub async fn compile(
     ),
   );
   log::debug!("Binary root dir: {}", root_dir_url);
-  let root_dir_url = EszipRelativeFileBaseUrl::new(&root_dir_url);
-  let eszip = eszip::EszipV2::from_graph(eszip::FromGraphOptions {
-    graph,
-    parser,
-    transpile_options,
-    emit_options,
-    // make all the modules relative to the root folder
-    relative_file_base: Some(root_dir_url),
-    npm_packages: None,
-  })?;
-
   log::info!(
     "{} {} to {}",
     colors::green("Compile"),
@@ -133,15 +116,18 @@ pub async fn compile(
   let write_result = binary_writer
     .write_bin(
       file,
-      eszip,
-      root_dir_url,
+      &graph,
+      StandaloneRelativeFileBaseUrl::from(&root_dir_url),
       module_specifier,
       &compile_flags,
       cli_options,
     )
     .await
     .with_context(|| {
-      format!("Writing temporary file '{}'", temp_path.display())
+      format!(
+        "Writing deno compile executable to temporary file '{}'",
+        temp_path.display()
+      )
     });
 
   // set it as executable
diff --git a/cli/tools/coverage/mod.rs b/cli/tools/coverage/mod.rs
index 260c0c8424..2a554c1335 100644
--- a/cli/tools/coverage/mod.rs
+++ b/cli/tools/coverage/mod.rs
@@ -6,12 +6,12 @@ use crate::args::FileFlags;
 use crate::args::Flags;
 use crate::cdp;
 use crate::factory::CliFactory;
-use crate::npm::CliNpmResolver;
 use crate::tools::fmt::format_json;
 use crate::tools::test::is_supported_test_path;
 use crate::util::text_encoding::source_map_from_code;
 
 use deno_ast::MediaType;
+use deno_ast::ModuleKind;
 use deno_ast::ModuleSpecifier;
 use deno_config::glob::FileCollector;
 use deno_config::glob::FilePatterns;
@@ -25,6 +25,7 @@ use deno_core::serde_json;
 use deno_core::sourcemap::SourceMap;
 use deno_core::url::Url;
 use deno_core::LocalInspectorSession;
+use node_resolver::InNpmPackageChecker;
 use regex::Regex;
 use std::fs;
 use std::fs::File;
@@ -327,6 +328,7 @@ fn generate_coverage_report(
 
   coverage_report.found_lines =
     if let Some(source_map) = maybe_source_map.as_ref() {
+      let script_source_lines = script_source.lines().collect::<Vec<_>>();
       let mut found_lines = line_counts
         .iter()
         .enumerate()
@@ -334,7 +336,23 @@ fn generate_coverage_report(
           // get all the mappings from this destination line to a different src line
           let mut results = source_map
             .tokens()
-            .filter(move |token| token.get_dst_line() as usize == index)
+            .filter(|token| {
+              let dst_line = token.get_dst_line() as usize;
+              dst_line == index && {
+                let dst_col = token.get_dst_col() as usize;
+                let content = script_source_lines
+                  .get(dst_line)
+                  .and_then(|line| {
+                    line.get(dst_col..std::cmp::min(dst_col + 2, line.len()))
+                  })
+                  .unwrap_or("");
+
+                !content.is_empty()
+                  && content != "/*"
+                  && content != "*/"
+                  && content != "//"
+              }
+            })
             .map(move |token| (token.get_src_line() as usize, *count))
             .collect::<Vec<_>>();
           // only keep the results that point at different src lines
@@ -444,7 +462,7 @@ fn filter_coverages(
   coverages: Vec<cdp::ScriptCoverage>,
   include: Vec<String>,
   exclude: Vec<String>,
-  npm_resolver: &dyn CliNpmResolver,
+  in_npm_pkg_checker: &dyn InNpmPackageChecker,
 ) -> Vec<cdp::ScriptCoverage> {
   let include: Vec<Regex> =
     include.iter().map(|e| Regex::new(e).unwrap()).collect();
@@ -462,13 +480,13 @@ fn filter_coverages(
     .filter(|e| {
       let is_internal = e.url.starts_with("ext:")
         || e.url.ends_with("__anonymous__")
-        || e.url.ends_with("$deno$test.js")
+        || e.url.ends_with("$deno$test.mjs")
         || e.url.ends_with(".snap")
         || is_supported_test_path(Path::new(e.url.as_str()))
         || doc_test_re.is_match(e.url.as_str())
         || Url::parse(&e.url)
           .ok()
-          .map(|url| npm_resolver.in_npm_package(&url))
+          .map(|url| in_npm_pkg_checker.in_npm_package(&url))
           .unwrap_or(false);
 
       let is_included = include.iter().any(|p| p.is_match(&e.url));
@@ -479,7 +497,7 @@ fn filter_coverages(
     .collect::<Vec<cdp::ScriptCoverage>>()
 }
 
-pub async fn cover_files(
+pub fn cover_files(
   flags: Arc<Flags>,
   coverage_flags: CoverageFlags,
 ) -> Result<(), AnyError> {
@@ -489,9 +507,10 @@ pub async fn cover_files(
 
   let factory = CliFactory::from_flags(flags);
   let cli_options = factory.cli_options()?;
-  let npm_resolver = factory.npm_resolver().await?;
+  let in_npm_pkg_checker = factory.in_npm_pkg_checker()?;
   let file_fetcher = factory.file_fetcher()?;
   let emitter = factory.emitter()?;
+  let cjs_tracker = factory.cjs_tracker()?;
 
   assert!(!coverage_flags.files.include.is_empty());
 
@@ -511,7 +530,7 @@ pub async fn cover_files(
     script_coverages,
     coverage_flags.include,
     coverage_flags.exclude,
-    npm_resolver.as_ref(),
+    in_npm_pkg_checker.as_ref(),
   );
   if script_coverages.is_empty() {
     return Err(generic_error("No covered files included in the report"));
@@ -568,16 +587,21 @@ pub async fn cover_files(
     let transpiled_code = match file.media_type {
       MediaType::JavaScript
       | MediaType::Unknown
+      | MediaType::Css
+      | MediaType::Wasm
       | MediaType::Cjs
       | MediaType::Mjs
       | MediaType::Json => None,
-      MediaType::Dts | MediaType::Dmts | MediaType::Dcts => Some(Vec::new()),
+      MediaType::Dts | MediaType::Dmts | MediaType::Dcts => Some(String::new()),
       MediaType::TypeScript
       | MediaType::Jsx
       | MediaType::Mts
       | MediaType::Cts
       | MediaType::Tsx => {
-        Some(match emitter.maybe_cached_emit(&file.specifier, &file.source) {
+        let module_kind = ModuleKind::from_is_cjs(
+          cjs_tracker.is_maybe_cjs(&file.specifier, file.media_type)?,
+        );
+        Some(match emitter.maybe_cached_emit(&file.specifier, module_kind, &file.source) {
           Some(code) => code,
           None => {
             return Err(anyhow!(
@@ -588,13 +612,12 @@ pub async fn cover_files(
           }
         })
       }
-      MediaType::Wasm | MediaType::TsBuildInfo | MediaType::SourceMap => {
+      MediaType::SourceMap => {
         unreachable!()
       }
     };
     let runtime_code: String = match transpiled_code {
-      Some(code) => String::from_utf8(code)
-        .with_context(|| format!("Failed decoding {}", file.specifier))?,
+      Some(code) => code,
       None => original_source.to_string(),
     };
 
diff --git a/cli/tools/doc.rs b/cli/tools/doc.rs
index 8f37632c84..e33da4efb2 100644
--- a/cli/tools/doc.rs
+++ b/cli/tools/doc.rs
@@ -22,9 +22,9 @@ use deno_core::serde_json;
 use deno_doc as doc;
 use deno_doc::html::UrlResolveKind;
 use deno_graph::source::NullFileSystem;
+use deno_graph::EsParser;
 use deno_graph::GraphKind;
 use deno_graph::ModuleAnalyzer;
-use deno_graph::ModuleParser;
 use deno_graph::ModuleSpecifier;
 use doc::html::ShortPath;
 use doc::DocDiagnostic;
@@ -37,7 +37,7 @@ const JSON_SCHEMA_VERSION: u8 = 1;
 
 async fn generate_doc_nodes_for_builtin_types(
   doc_flags: DocFlags,
-  parser: &dyn ModuleParser,
+  parser: &dyn EsParser,
   analyzer: &dyn ModuleAnalyzer,
 ) -> Result<IndexMap<ModuleSpecifier, Vec<doc::DocNode>>, AnyError> {
   let source_file_specifier =
@@ -96,7 +96,7 @@ pub async fn doc(
   let module_info_cache = factory.module_info_cache()?;
   let parsed_source_cache = factory.parsed_source_cache();
   let capturing_parser = parsed_source_cache.as_capturing_parser();
-  let analyzer = module_info_cache.as_module_analyzer(parsed_source_cache);
+  let analyzer = module_info_cache.as_module_analyzer();
 
   let doc_nodes_by_url = match doc_flags.source_files {
     DocSourceFileFlag::Builtin => {
@@ -195,7 +195,7 @@ pub async fn doc(
             kind_with_drilldown:
               deno_doc::html::DocNodeKindWithDrilldown::Other(node.kind()),
             inner: Rc::new(node),
-            drilldown_parent_kind: None,
+            drilldown_name: None,
             parent: None,
           })
           .collect::<Vec<_>>(),
@@ -262,7 +262,7 @@ pub async fn doc(
 }
 
 struct DocResolver {
-  deno_ns: std::collections::HashSet<Vec<String>>,
+  deno_ns: std::collections::HashMap<Vec<String>, Option<Rc<ShortPath>>>,
   strip_trailing_html: bool,
 }
 
@@ -286,7 +286,7 @@ impl deno_doc::html::HrefResolver for DocResolver {
   }
 
   fn resolve_global_symbol(&self, symbol: &[String]) -> Option<String> {
-    if self.deno_ns.contains(symbol) {
+    if self.deno_ns.contains_key(symbol) {
       Some(format!(
         "https://deno.land/api@v{}?s={}",
         env!("CARGO_PKG_VERSION"),
@@ -455,7 +455,7 @@ impl deno_doc::html::HrefResolver for NodeDocResolver {
 fn generate_docs_directory(
   doc_nodes_by_url: IndexMap<ModuleSpecifier, Vec<doc::DocNode>>,
   html_options: &DocHtmlFlag,
-  deno_ns: std::collections::HashSet<Vec<String>>,
+  deno_ns: std::collections::HashMap<Vec<String>, Option<Rc<ShortPath>>>,
   rewrite_map: Option<IndexMap<ModuleSpecifier, String>>,
 ) -> Result<(), AnyError> {
   let cwd = std::env::current_dir().context("Failed to get CWD")?;
@@ -513,7 +513,6 @@ fn generate_docs_directory(
     rewrite_map,
     href_resolver,
     usage_composer: None,
-    composable_output: false,
     category_docs,
     disable_search: internal_env.is_some(),
     symbol_redirect_map,
diff --git a/cli/tools/fmt.rs b/cli/tools/fmt.rs
index 8a4bc4e6c8..56b1632cfb 100644
--- a/cli/tools/fmt.rs
+++ b/cli/tools/fmt.rs
@@ -353,6 +353,21 @@ fn format_yaml(
   file_text: &str,
   fmt_options: &FmtOptionsConfig,
 ) -> Result<Option<String>, AnyError> {
+  let ignore_file = file_text
+    .lines()
+    .take_while(|line| line.starts_with('#'))
+    .any(|line| {
+      line
+        .strip_prefix('#')
+        .unwrap()
+        .trim()
+        .starts_with("deno-fmt-ignore-file")
+    });
+
+  if ignore_file {
+    return Ok(None);
+  }
+
   let formatted_str =
     pretty_yaml::format_text(file_text, &get_resolved_yaml_config(fmt_options))
       .map_err(AnyError::from)?;
@@ -775,28 +790,26 @@ fn format_ensure_stable(
             return Ok(Some(current_text));
           }
           Err(err) => {
-            panic!(
+            bail!(
               concat!(
                 "Formatting succeeded initially, but failed when ensuring a ",
                 "stable format. This indicates a bug in the formatter where ",
                 "the text it produces is not syntactically correct. As a temporary ",
-                "workaround you can ignore this file ({}).\n\n{:#}"
+                "workaround you can ignore this file.\n\n{:#}"
               ),
-              file_path.display(),
               err,
             )
           }
         }
         count += 1;
         if count == 5 {
-          panic!(
+          bail!(
             concat!(
               "Formatting not stable. Bailed after {} tries. This indicates a bug ",
-              "in the formatter where it formats the file ({}) differently each time. As a ",
+              "in the formatter where it formats the file differently each time. As a ",
               "temporary workaround you can ignore this file."
             ),
             count,
-            file_path.display(),
           )
         }
       }
@@ -978,6 +991,7 @@ fn get_resolved_malva_config(
     single_line_top_level_declarations: false,
     selector_override_comment_directive: "deno-fmt-selector-override".into(),
     ignore_comment_directive: "deno-fmt-ignore".into(),
+    ignore_file_comment_directive: "deno-fmt-ignore-file".into(),
   };
 
   FormatOptions {
@@ -1016,7 +1030,7 @@ fn get_resolved_markup_fmt_config(
     max_attrs_per_line: None,
     prefer_attrs_single_line: false,
     html_normal_self_closing: None,
-    html_void_self_closing: Some(true),
+    html_void_self_closing: None,
     component_self_closing: None,
     svg_self_closing: None,
     mathml_self_closing: None,
@@ -1036,6 +1050,7 @@ fn get_resolved_markup_fmt_config(
     svelte_directive_shorthand: Some(true),
     astro_attr_shorthand: Some(true),
     ignore_comment_directive: "deno-fmt-ignore".into(),
+    ignore_file_comment_directive: "deno-fmt-ignore-file".into(),
   };
 
   FormatOptions {
@@ -1198,6 +1213,8 @@ fn is_supported_ext_fmt(path: &Path) -> bool {
 
 #[cfg(test)]
 mod test {
+  use test_util::assert_starts_with;
+
   use super::*;
 
   #[test]
@@ -1253,12 +1270,16 @@ mod test {
   }
 
   #[test]
-  #[should_panic(expected = "Formatting not stable. Bailed after 5 tries.")]
   fn test_format_ensure_stable_unstable_format() {
-    format_ensure_stable(&PathBuf::from("mod.ts"), "1", |_, file_text| {
-      Ok(Some(format!("1{file_text}")))
-    })
-    .unwrap();
+    let err =
+      format_ensure_stable(&PathBuf::from("mod.ts"), "1", |_, file_text| {
+        Ok(Some(format!("1{file_text}")))
+      })
+      .unwrap_err();
+    assert_starts_with!(
+      err.to_string(),
+      "Formatting not stable. Bailed after 5 tries."
+    );
   }
 
   #[test]
@@ -1272,16 +1293,20 @@ mod test {
   }
 
   #[test]
-  #[should_panic(expected = "Formatting succeeded initially, but failed when")]
   fn test_format_ensure_stable_error_second() {
-    format_ensure_stable(&PathBuf::from("mod.ts"), "1", |_, file_text| {
-      if file_text == "1" {
-        Ok(Some("11".to_string()))
-      } else {
-        bail!("Error formatting.")
-      }
-    })
-    .unwrap();
+    let err =
+      format_ensure_stable(&PathBuf::from("mod.ts"), "1", |_, file_text| {
+        if file_text == "1" {
+          Ok(Some("11".to_string()))
+        } else {
+          bail!("Error formatting.")
+        }
+      })
+      .unwrap_err();
+    assert_starts_with!(
+      err.to_string(),
+      "Formatting succeeded initially, but failed when"
+    );
   }
 
   #[test]
diff --git a/cli/tools/info.rs b/cli/tools/info.rs
index 1c83abe3bb..c2f5a8cb8d 100644
--- a/cli/tools/info.rs
+++ b/cli/tools/info.rs
@@ -11,12 +11,14 @@ use deno_core::anyhow::bail;
 use deno_core::error::AnyError;
 use deno_core::resolve_url_or_path;
 use deno_core::serde_json;
+use deno_core::url;
 use deno_graph::Dependency;
 use deno_graph::GraphKind;
 use deno_graph::Module;
 use deno_graph::ModuleError;
 use deno_graph::ModuleGraph;
 use deno_graph::Resolution;
+use deno_npm::npm_rc::ResolvedNpmRc;
 use deno_npm::resolution::NpmResolutionSnapshot;
 use deno_npm::NpmPackageId;
 use deno_npm::NpmResolutionPackage;
@@ -47,20 +49,23 @@ pub async fn info(
     let module_graph_creator = factory.module_graph_creator().await?;
     let npm_resolver = factory.npm_resolver().await?;
     let maybe_lockfile = cli_options.maybe_lockfile();
+    let npmrc = cli_options.npmrc();
     let resolver = factory.workspace_resolver().await?;
 
-    let maybe_import_specifier =
-      if let Some(import_map) = resolver.maybe_import_map() {
-        if let Ok(imports_specifier) =
-          import_map.resolve(&specifier, import_map.base_url())
-        {
-          Some(imports_specifier)
-        } else {
-          None
-        }
+    let cwd_url =
+      url::Url::from_directory_path(cli_options.initial_cwd()).unwrap();
+
+    let maybe_import_specifier = if let Some(import_map) =
+      resolver.maybe_import_map()
+    {
+      if let Ok(imports_specifier) = import_map.resolve(&specifier, &cwd_url) {
+        Some(imports_specifier)
       } else {
         None
-      };
+      }
+    } else {
+      None
+    };
 
     let specifier = match maybe_import_specifier {
       Some(specifier) => specifier,
@@ -88,7 +93,8 @@ pub async fn info(
           JSON_SCHEMA_VERSION.into(),
         );
       }
-      add_npm_packages_to_json(&mut json_graph, npm_resolver.as_ref());
+
+      add_npm_packages_to_json(&mut json_graph, npm_resolver.as_ref(), npmrc);
       display::write_json_to_stdout(&json_graph)?;
     } else {
       let mut output = String::new();
@@ -185,6 +191,7 @@ fn print_cache_info(
 fn add_npm_packages_to_json(
   json: &mut serde_json::Value,
   npm_resolver: &dyn CliNpmResolver,
+  npmrc: &ResolvedNpmRc,
 ) {
   let Some(npm_resolver) = npm_resolver.as_managed() else {
     return; // does not include byonm to deno info's output
@@ -195,45 +202,28 @@ fn add_npm_packages_to_json(
   let json = json.as_object_mut().unwrap();
   let modules = json.get_mut("modules").and_then(|m| m.as_array_mut());
   if let Some(modules) = modules {
-    if modules.len() == 1
-      && modules[0].get("kind").and_then(|k| k.as_str()) == Some("npm")
-    {
-      // If there is only one module and it's "external", then that means
-      // someone provided an npm specifier as a cli argument. In this case,
-      // we want to show which npm package the cli argument resolved to.
-      let module = &mut modules[0];
-      let maybe_package = module
-        .get("specifier")
-        .and_then(|k| k.as_str())
-        .and_then(|specifier| NpmPackageNvReference::from_str(specifier).ok())
-        .and_then(|package_ref| {
-          snapshot
-            .resolve_package_from_deno_module(package_ref.nv())
-            .ok()
-        });
-      if let Some(pkg) = maybe_package {
-        if let Some(module) = module.as_object_mut() {
-          module
-            .insert("npmPackage".to_string(), pkg.id.as_serialized().into());
-        }
-      }
-    } else {
-      // Filter out npm package references from the modules and instead
-      // have them only listed as dependencies. This is done because various
-      // npm specifiers modules in the graph are really just unresolved
-      // references. So there could be listed multiple npm specifiers
-      // that would resolve to a single npm package.
-      for i in (0..modules.len()).rev() {
-        if matches!(
-          modules[i].get("kind").and_then(|k| k.as_str()),
-          Some("npm") | Some("external")
-        ) {
-          modules.remove(i);
-        }
-      }
-    }
-
     for module in modules.iter_mut() {
+      if matches!(module.get("kind").and_then(|k| k.as_str()), Some("npm")) {
+        // If there is only one module and it's "external", then that means
+        // someone provided an npm specifier as a cli argument. In this case,
+        // we want to show which npm package the cli argument resolved to.
+        let maybe_package = module
+          .get("specifier")
+          .and_then(|k| k.as_str())
+          .and_then(|specifier| NpmPackageNvReference::from_str(specifier).ok())
+          .and_then(|package_ref| {
+            snapshot
+              .resolve_package_from_deno_module(package_ref.nv())
+              .ok()
+          });
+        if let Some(pkg) = maybe_package {
+          if let Some(module) = module.as_object_mut() {
+            module
+              .insert("npmPackage".to_string(), pkg.id.as_serialized().into());
+          }
+        }
+      }
+
       let dependencies = module
         .get_mut("dependencies")
         .and_then(|d| d.as_array_mut());
@@ -265,7 +255,7 @@ fn add_npm_packages_to_json(
   let mut json_packages = serde_json::Map::with_capacity(sorted_packages.len());
   for pkg in sorted_packages {
     let mut kv = serde_json::Map::new();
-    kv.insert("name".to_string(), pkg.id.nv.name.to_string().into());
+    kv.insert("name".to_string(), pkg.id.nv.name.clone().into());
     kv.insert("version".to_string(), pkg.id.nv.version.to_string().into());
     let mut deps = pkg.dependencies.values().collect::<Vec<_>>();
     deps.sort();
@@ -274,6 +264,8 @@ fn add_npm_packages_to_json(
       .map(|id| serde_json::Value::String(id.as_serialized()))
       .collect::<Vec<_>>();
     kv.insert("dependencies".to_string(), deps.into());
+    let registry_url = npmrc.get_registry_url(&pkg.id.nv.name);
+    kv.insert("registryUrl".to_string(), registry_url.to_string().into());
 
     json_packages.insert(pkg.id.as_serialized(), kv.into());
   }
@@ -538,7 +530,7 @@ impl<'a> GraphDisplayContext<'a> {
 
   fn build_module_info(&mut self, module: &Module, type_dep: bool) -> TreeNode {
     enum PackageOrSpecifier {
-      Package(NpmResolutionPackage),
+      Package(Box<NpmResolutionPackage>),
       Specifier(ModuleSpecifier),
     }
 
@@ -546,7 +538,7 @@ impl<'a> GraphDisplayContext<'a> {
 
     let package_or_specifier = match module.npm() {
       Some(npm) => match self.npm_info.resolve_package(npm.nv_reference.nv()) {
-        Some(package) => Package(package.clone()),
+        Some(package) => Package(Box::new(package.clone())),
         None => Specifier(module.specifier().clone()), // should never happen
       },
       None => Specifier(module.specifier().clone()),
@@ -653,10 +645,12 @@ impl<'a> GraphDisplayContext<'a> {
         let message = match err {
           HttpsChecksumIntegrity(_) => "(checksum integrity error)",
           Decode(_) => "(loading decode error)",
-          Loader(err) => match deno_core::error::get_custom_error_class(err) {
-            Some("NotCapable") => "(not capable, requires --allow-import)",
-            _ => "(loading error)",
-          },
+          Loader(err) => {
+            match deno_runtime::errors::get_error_class_name(err) {
+              Some("NotCapable") => "(not capable, requires --allow-import)",
+              _ => "(loading error)",
+            }
+          }
           Jsr(_) => "(loading error)",
           NodeUnknownBuiltinModule(_) => "(unknown node built-in error)",
           Npm(_) => "(npm loading error)",
diff --git a/cli/tools/init/mod.rs b/cli/tools/init/mod.rs
index 2d6a894e13..4e4a686c5f 100644
--- a/cli/tools/init/mod.rs
+++ b/cli/tools/init/mod.rs
@@ -24,32 +24,29 @@ pub fn init_project(init_flags: InitFlags) -> Result<(), AnyError> {
     create_file(
       &dir,
       "main.ts",
-      r#"import { type Route, route, serveDir } from "@std/http";
+      r#"import { serveDir } from "@std/http";
 
-const routes: Route[] = [
-  {
-    pattern: new URLPattern({ pathname: "/" }),
-    handler: () => new Response("Home page"),
-  },
-  {
-    pattern: new URLPattern({ pathname: "/users/:id" }),
-    handler: (_req, _info, params) => new Response(params?.pathname.groups.id),
-  },
-  {
-    pattern: new URLPattern({ pathname: "/static/*" }),
-    handler: (req) => serveDir(req),
-  },
-];
-
-function defaultHandler(_req: Request) {
-  return new Response("Not found", { status: 404 });
-}
-
-const handler = route(routes, defaultHandler);
+const userPagePattern = new URLPattern({ pathname: "/users/:id" });
+const staticPathPattern = new URLPattern({ pathname: "/static/*" });
 
 export default {
   fetch(req) {
-    return handler(req);
+    const url = new URL(req.url);
+
+    if (url.pathname === "/") {
+      return new Response("Home page");
+    }
+
+    const userPageMatch = userPagePattern.exec(url);
+    if (userPageMatch) {
+      return new Response(userPageMatch.pathname.groups.id);
+    }
+
+    if (staticPathPattern.test(url)) {
+      return serveDir(req);
+    }
+
+    return new Response("Not found", { status: 404 });
   },
 } satisfies Deno.ServeDefaultExport;
 "#,
diff --git a/cli/tools/installer.rs b/cli/tools/installer.rs
index bc8769de1c..1655f0a322 100644
--- a/cli/tools/installer.rs
+++ b/cli/tools/installer.rs
@@ -298,6 +298,10 @@ async fn install_local(
     }
     InstallFlagsLocal::TopLevel => {
       let factory = CliFactory::from_flags(flags);
+      // surface any errors in the package.json
+      if let Some(npm_resolver) = factory.npm_resolver().await?.as_managed() {
+        npm_resolver.ensure_no_pkg_json_dep_errors()?;
+      }
       crate::tools::registry::cache_top_level_deps(&factory, None).await?;
 
       if let Some(lockfile) = factory.cli_options()?.maybe_lockfile() {
@@ -1392,6 +1396,7 @@ mod tests {
       .env_clear()
       // use the deno binary in the target directory
       .env("PATH", test_util::target_dir())
+      .env("RUST_BACKTRACE", "1")
       .spawn()
       .unwrap()
       .wait()
diff --git a/cli/tools/jupyter/install.rs b/cli/tools/jupyter/install.rs
index b0ddc948d6..aeff89ccf4 100644
--- a/cli/tools/jupyter/install.rs
+++ b/cli/tools/jupyter/install.rs
@@ -58,9 +58,9 @@ pub fn install() -> Result<(), AnyError> {
 
   let f = std::fs::File::create(kernel_json_path)?;
   serde_json::to_writer_pretty(f, &json_data)?;
-  install_icon(&user_data_dir, "logo-32x32.png", DENO_ICON_32)?;
-  install_icon(&user_data_dir, "logo-64x64.png", DENO_ICON_64)?;
-  install_icon(&user_data_dir, "logo-svg.svg", DENO_ICON_SVG)?;
+  install_icon(&kernel_dir, "logo-32x32.png", DENO_ICON_32)?;
+  install_icon(&kernel_dir, "logo-64x64.png", DENO_ICON_64)?;
+  install_icon(&kernel_dir, "logo-svg.svg", DENO_ICON_SVG)?;
 
   log::info!("✅ Deno kernelspec installed successfully.");
   Ok(())
diff --git a/cli/tools/jupyter/mod.rs b/cli/tools/jupyter/mod.rs
index 71e947dddb..732f95c49f 100644
--- a/cli/tools/jupyter/mod.rs
+++ b/cli/tools/jupyter/mod.rs
@@ -61,7 +61,7 @@ pub async fn kernel(
   let factory = CliFactory::from_flags(flags);
   let cli_options = factory.cli_options()?;
   let main_module =
-    resolve_url_or_path("./$deno$jupyter.ts", cli_options.initial_cwd())
+    resolve_url_or_path("./$deno$jupyter.mts", cli_options.initial_cwd())
       .unwrap();
   // TODO(bartlomieju): should we run with all permissions?
   let permissions =
@@ -357,56 +357,74 @@ pub struct JupyterReplSession {
 
 impl JupyterReplSession {
   pub async fn start(&mut self) {
+    let mut poll_worker = true;
     loop {
-      let Some(msg) = self.rx.recv().await else {
-        break;
-      };
-      let resp = match msg {
-        JupyterReplRequest::LspCompletions {
-          line_text,
-          position,
-        } => JupyterReplResponse::LspCompletions(
-          self.lsp_completions(&line_text, position).await,
-        ),
-        JupyterReplRequest::JsGetProperties { object_id } => {
-          JupyterReplResponse::JsGetProperties(
-            self.get_properties(object_id).await,
-          )
-        }
-        JupyterReplRequest::JsEvaluate { expr } => {
-          JupyterReplResponse::JsEvaluate(self.evaluate(expr).await)
-        }
-        JupyterReplRequest::JsGlobalLexicalScopeNames => {
-          JupyterReplResponse::JsGlobalLexicalScopeNames(
-            self.global_lexical_scope_names().await,
-          )
-        }
-        JupyterReplRequest::JsEvaluateLineWithObjectWrapping { line } => {
-          JupyterReplResponse::JsEvaluateLineWithObjectWrapping(
-            self.evaluate_line_with_object_wrapping(&line).await,
-          )
-        }
-        JupyterReplRequest::JsCallFunctionOnArgs {
-          function_declaration,
-          args,
-        } => JupyterReplResponse::JsCallFunctionOnArgs(
-          self
-            .call_function_on_args(function_declaration, &args)
-            .await,
-        ),
-        JupyterReplRequest::JsCallFunctionOn { arg0, arg1 } => {
-          JupyterReplResponse::JsCallFunctionOn(
-            self.call_function_on(arg0, arg1).await,
-          )
-        }
-      };
+      tokio::select! {
+        biased;
 
-      let Ok(()) = self.tx.send(resp) else {
-        break;
-      };
+        maybe_message = self.rx.recv() => {
+          let Some(msg) = maybe_message else {
+            break;
+          };
+          if self.handle_message(msg).await.is_err() {
+            break;
+          }
+          poll_worker = true;
+        },
+        _ = self.repl_session.run_event_loop(), if poll_worker => {
+          poll_worker = false;
+        }
+      }
     }
   }
 
+  async fn handle_message(
+    &mut self,
+    msg: JupyterReplRequest,
+  ) -> Result<(), AnyError> {
+    let resp = match msg {
+      JupyterReplRequest::LspCompletions {
+        line_text,
+        position,
+      } => JupyterReplResponse::LspCompletions(
+        self.lsp_completions(&line_text, position).await,
+      ),
+      JupyterReplRequest::JsGetProperties { object_id } => {
+        JupyterReplResponse::JsGetProperties(
+          self.get_properties(object_id).await,
+        )
+      }
+      JupyterReplRequest::JsEvaluate { expr } => {
+        JupyterReplResponse::JsEvaluate(self.evaluate(expr).await)
+      }
+      JupyterReplRequest::JsGlobalLexicalScopeNames => {
+        JupyterReplResponse::JsGlobalLexicalScopeNames(
+          self.global_lexical_scope_names().await,
+        )
+      }
+      JupyterReplRequest::JsEvaluateLineWithObjectWrapping { line } => {
+        JupyterReplResponse::JsEvaluateLineWithObjectWrapping(
+          self.evaluate_line_with_object_wrapping(&line).await,
+        )
+      }
+      JupyterReplRequest::JsCallFunctionOnArgs {
+        function_declaration,
+        args,
+      } => JupyterReplResponse::JsCallFunctionOnArgs(
+        self
+          .call_function_on_args(function_declaration, &args)
+          .await,
+      ),
+      JupyterReplRequest::JsCallFunctionOn { arg0, arg1 } => {
+        JupyterReplResponse::JsCallFunctionOn(
+          self.call_function_on(arg0, arg1).await,
+        )
+      }
+    };
+
+    self.tx.send(resp).map_err(|e| e.into())
+  }
+
   pub async fn lsp_completions(
     &mut self,
     line_text: &str,
diff --git a/cli/tools/jupyter/resources/deno-logo-32x32.png b/cli/tools/jupyter/resources/deno-logo-32x32.png
index 97871a02ee..d59f251a24 100644
Binary files a/cli/tools/jupyter/resources/deno-logo-32x32.png and b/cli/tools/jupyter/resources/deno-logo-32x32.png differ
diff --git a/cli/tools/jupyter/resources/deno-logo-64x64.png b/cli/tools/jupyter/resources/deno-logo-64x64.png
index 1b9444ef63..37e98abafd 100644
Binary files a/cli/tools/jupyter/resources/deno-logo-64x64.png and b/cli/tools/jupyter/resources/deno-logo-64x64.png differ
diff --git a/cli/tools/jupyter/resources/deno-logo-svg.svg b/cli/tools/jupyter/resources/deno-logo-svg.svg
index d7bb9ef804..fbc22cd910 100644
--- a/cli/tools/jupyter/resources/deno-logo-svg.svg
+++ b/cli/tools/jupyter/resources/deno-logo-svg.svg
@@ -1 +1,17 @@
-<svg viewBox="0 0 30 30" fill="none" xmlns="http://www.w3.org/2000/svg"><g clip-path="url(#clip0_29_599)"><path d="M15 0C23.2843 0 30 6.71572 30 15C30 23.2843 23.2843 30 15 30C6.71572 30 0 23.2843 0 15C0 6.71572 6.71572 0 15 0Z" fill="currentColor"></path><path d="M14.6635 22.3394C14.2788 22.2357 13.8831 22.4584 13.7705 22.8381L13.7655 22.8558L12.7694 26.5472L12.7649 26.565C12.6711 26.9498 12.9011 27.3414 13.2858 27.4451C13.6704 27.549 14.0661 27.3263 14.1787 26.9465L14.1837 26.9289L15.1797 23.2375L15.1843 23.2196C15.1911 23.1919 15.1962 23.164 15.1997 23.1362L15.2026 23.1084L15.179 22.9888L15.1445 22.8166L15.1227 22.7091C15.076 22.619 15.0111 22.5396 14.932 22.4759C14.853 22.4123 14.7615 22.3658 14.6635 22.3394ZM7.7224 18.5379C7.70424 18.5741 7.68883 18.6123 7.67658 18.6522L7.66967 18.6763L6.67358 22.3677L6.669 22.3856C6.57525 22.7704 6.80524 23.1619 7.1899 23.2657C7.57451 23.3695 7.97026 23.1469 8.08287 22.7671L8.08779 22.7494L8.99096 19.4023C8.51793 19.1518 8.09336 18.8628 7.7224 18.5379ZM5.34707 14.2929C4.9624 14.1891 4.56666 14.4117 4.4541 14.7915L4.44912 14.8092L3.45303 18.5006L3.44846 18.5184C3.35471 18.9032 3.58469 19.2947 3.96936 19.3985C4.35397 19.5023 4.74971 19.2797 4.86232 18.8999L4.86725 18.8822L5.86334 15.1908L5.86791 15.173C5.96166 14.7882 5.73174 14.3967 5.34707 14.2929ZM27.682 13.4546C27.2973 13.3508 26.9015 13.5734 26.789 13.9532L26.784 13.9709L25.7879 17.6623L25.7833 17.6801C25.6896 18.0649 25.9196 18.4564 26.3042 18.5602C26.6889 18.664 27.0846 18.4414 27.1972 18.0616L27.2021 18.0439L28.1982 14.3525L28.2028 14.3347C28.2965 13.9499 28.0666 13.5584 27.682 13.4546ZM3.17781 8.52527C2.34361 10.0444 1.81243 11.7112 1.61377 13.4329C1.7088 13.5412 1.83381 13.619 1.97301 13.6563C2.35768 13.7602 2.75342 13.5375 2.86598 13.1577L2.87096 13.1401L3.86705 9.44865L3.87162 9.43084C3.96537 9.04599 3.73539 8.65447 3.35072 8.5507C3.2943 8.53547 3.23623 8.52694 3.17781 8.52527ZM25.159 8.5507C24.7744 8.44687 24.3786 8.66953 24.266 9.04933L24.2611 9.06697L23.265 12.7584L23.2604 12.7762C23.1667 13.161 23.3966 13.5526 23.7813 13.6563C24.1659 13.7602 24.5617 13.5375 24.6743 13.1577L24.6792 13.1401L25.6753 9.44865L25.6799 9.43084C25.7736 9.04599 25.5436 8.65447 25.159 8.5507Z" fill="white"></path><path d="M7.51285 5.04065C7.12824 4.93682 6.73249 5.15948 6.61988 5.53929L6.61495 5.55692L5.61886 9.24833L5.61429 9.26614C5.52054 9.65098 5.75052 10.0425 6.13519 10.1463C6.5198 10.2501 6.91554 10.0274 7.02816 9.64764L7.03308 9.63001L8.02917 5.9386L8.03374 5.92079C8.12749 5.53595 7.89751 5.14442 7.51285 5.04065ZM20.3116 5.73845C19.9269 5.63462 19.5312 5.85727 19.4186 6.23708L19.4136 6.25471L18.7443 8.73499C19.1779 8.94915 19.5917 9.20126 19.9809 9.48839L20.0453 9.53643L20.8279 6.63639L20.8324 6.61858C20.9262 6.23374 20.6963 5.84221 20.3116 5.73845ZM13.7968 1.57642C13.3296 1.61771 12.8647 1.68338 12.4043 1.77317L12.3066 1.79263L11.3782 5.23419L11.3736 5.252C11.2799 5.63684 11.5099 6.02837 11.8945 6.13214C12.2792 6.23596 12.6749 6.01331 12.7875 5.6335L12.7924 5.61587L13.7885 1.92446L13.7931 1.90665C13.8196 1.79831 13.8209 1.68533 13.7968 1.57642ZM22.9626 4.1263L22.7669 4.85169L22.7623 4.86944C22.6686 5.25429 22.8986 5.64581 23.2832 5.74958C23.6678 5.85341 24.0636 5.63075 24.1762 5.25095L24.1811 5.23331L24.2025 5.15462C23.8362 4.81205 23.4511 4.49009 23.0491 4.19022L22.9626 4.1263ZM17.1672 1.69677L16.8139 3.00593L16.8094 3.02374C16.7156 3.40858 16.9456 3.80011 17.3303 3.90388C17.7149 4.0077 18.1106 3.78505 18.2233 3.40524L18.2282 3.38761L18.6 2.00966C18.1624 1.88867 17.719 1.79001 17.2714 1.71405L17.1672 1.69677Z" fill="white"></path><path d="M9.69085 24.6253C9.80341 24.2455 10.1992 24.0229 10.5838 24.1266C10.9685 24.2303 11.1984 24.6219 11.1047 25.0068L11.1001 25.0246L10.3872 27.6664L10.2876 27.6297C9.85836 27.4694 9.43765 27.2873 9.0271 27.0839L9.68587 24.6429L9.69085 24.6253Z" fill="white"></path><path d="M14.4141 8.49082C10.0522 8.49082 6.65918 11.2368 6.65918 14.6517C6.65918 17.8769 9.78123 19.9362 14.6211 19.8331C15.0327 19.8243 15.1517 20.1008 15.2856 20.4734C15.4196 20.846 15.7796 22.8097 16.0665 24.3117C16.3233 25.656 16.5842 27.0052 16.7834 28.3596C19.9439 27.9418 22.8663 26.3807 25.0076 24.0261L22.7237 15.5088C22.1544 13.4518 21.489 11.5564 19.7283 10.1794C18.3118 9.07166 16.5122 8.49082 14.4141 8.49082Z" fill="white"></path><path d="M15.3516 10.957C15.8694 10.957 16.2891 11.3767 16.2891 11.8945C16.2891 12.4123 15.8694 12.832 15.3516 12.832C14.8338 12.832 14.4141 12.4123 14.4141 11.8945C14.4141 11.3767 14.8338 10.957 15.3516 10.957Z" fill="currentColor"></path></g><defs><clipPath id="clip0_29_599"><rect width="30" height="30" fill="white"></rect></clipPath></defs></svg>
+<svg width="100%" height="100%" viewBox="0 0 441 441" version="1.1" xmlns="http://www.w3.org/2000/svg"
+  xmlns:xlink="http://www.w3.org/1999/xlink" xml:space="preserve" xmlns:serif="http://www.serif.com/"
+  style="fill-rule:evenodd;clip-rule:evenodd;stroke-linejoin:round;stroke-miterlimit:2;">
+  <g transform="matrix(1.02631,-2.08167e-17,2.08167e-17,1.02631,-0.525826,-0.525138)">
+    <path
+      d="M37.965,296.635C26.441,271.766 20.009,244.065 20.009,214.873C20.009,207.318 20.439,199.863 21.278,192.531C22.129,185.123 23.39,177.852 25.036,170.742C34.286,130.852 55.801,95.64 85.384,69.301C110.233,47.207 140.674,31.444 174.043,24.299C187.212,21.486 200.872,20.006 214.875,20.006C219.783,20.011 224.727,20.2 229.701,20.579C253.285,22.38 275.571,28.317 295.904,37.625C312.305,45.143 327.486,54.87 341.064,66.426C375.17,95.48 398.957,135.953 406.867,181.369C408.757,192.255 409.742,203.45 409.742,214.873C409.738,219.789 409.548,224.74 409.168,229.721C407.731,248.545 403.659,266.542 397.34,283.379C388.521,306.83 375.308,328.136 358.706,346.294C337.113,368.342 309.673,378.152 286.755,377.744C270.09,377.447 253.784,370.816 242.516,361.114C226.42,347.253 219.918,331.409 217.69,313.729C217.136,309.334 217.461,297.358 219.748,289.066C221.453,282.885 225.777,270.948 232.1,265.727C224.703,262.541 215.183,255.604 212.182,252.274C211.445,251.455 211.54,250.174 212.2,249.292C212.861,248.41 214.02,248.062 215.057,248.435C221.416,250.618 229.161,252.771 237.327,254.137C248.067,255.932 261.424,258.194 274.955,258.859C307.946,260.479 342.407,245.67 353.103,216.207C363.798,186.744 359.649,157.602 321.279,140.121C282.909,122.64 265.185,101.856 234.183,89.32C213.934,81.131 191.396,85.992 168.257,98.78C105.931,133.223 50.092,242.048 75.833,342.873C76.201,344.252 75.58,345.705 74.328,346.392C73.156,347.036 71.713,346.852 70.741,345.962C63.25,337.731 56.454,328.857 50.445,319.433C45.796,312.139 41.623,304.524 37.965,296.635Z" />
+  </g>
+  <g transform="matrix(0.0920293,0.00428099,-0.00428099,0.0920293,-28.1272,-500.301)">
+    <path
+      d="M3053.7,5296.9C4371.65,5296.9 5441.66,6366.91 5441.66,7684.86C5441.66,9002.81 4371.65,10072.8 3053.7,10072.8C1735.75,10072.8 665.74,9002.81 665.74,7684.86C665.74,6366.91 1735.75,5296.9 3053.7,5296.9ZM3745.03,8143.22C3594.12,8142.82 3444.31,8124.57 3323.87,8110.15C3232.29,8099.18 3144.99,8079.23 3073.1,8058.23C3061.36,8054.62 3048.65,8059.09 3041.75,8069.24C3034.86,8079.4 3034.46,8093.71 3043.09,8102.44C3078.21,8137.94 3187.74,8210.21 3271.7,8241.83C3204.04,8303.2 3162.1,8438.28 3146.33,8507.94C3125.17,8601.4 3127.75,8734.83 3136.19,8783.45C3170.14,8979.04 3250.69,9151.99 3436.99,9297.9C3567.4,9400.03 3752.28,9465.38 3937.88,9460.06C4194.01,9452.71 4495.48,9328.51 4724.65,9070.17C5023.25,8710.58 5208.52,8252.45 5223.47,7749.5C5259.08,6551.9 4315.7,5550.69 3118.1,5515.08C1920.51,5479.47 919.301,6422.86 883.689,7620.45C865.246,8240.66 1109.37,8808.21 1515.43,9216.2C1526.73,9227.39 1544.21,9229.43 1557.78,9221.14C1571.35,9212.85 1577.51,9196.36 1572.7,9181.2C1234.07,8072.55 1799.11,6832.64 2474.84,6417.1C2725.71,6262.82 2973.99,6197.06 3203.56,6277.7C3555.04,6401.15 3763.03,6623.26 4199.06,6797.93C4635.09,6972.59 4696.35,7294.74 4592.58,7628.14C4488.81,7961.54 4113,8144.17 3745.03,8143.22ZM2917.17,6442.51C2777.75,6459.97 2693.93,6637.44 2687.08,6749.42C2680.18,6861.39 2744.03,7042.7 2926.19,7030.63C3139.52,7016.49 3195.89,6830.7 3164.24,6654.94C3140.48,6522.94 3033.73,6427.9 2917.17,6442.51Z"
+      style="fill:white;" />
+  </g>
+  <g transform="matrix(7.12289,0.543899,-0.543899,7.12289,-4867.49,-1040.55)">
+    <path
+      d="M721.316,105.751C722.813,105.518 724.225,106.703 724.582,108.395C725.058,110.649 724.402,113.065 721.658,113.329C719.314,113.555 718.422,111.242 718.468,109.796C718.513,108.35 719.525,106.03 721.316,105.751Z" />
+  </g>
+</svg>
diff --git a/cli/tools/jupyter/server.rs b/cli/tools/jupyter/server.rs
index 0cd80f7ddd..5680ed4c13 100644
--- a/cli/tools/jupyter/server.rs
+++ b/cli/tools/jupyter/server.rs
@@ -329,7 +329,12 @@ impl JupyterServer {
             })
             .collect();
 
-            (candidates, cursor_pos - prop_name.len())
+            if prop_name.len() > cursor_pos {
+              // TODO(bartlomieju): most likely not correct, but better than panicking because of sub with overflow
+              (candidates, cursor_pos)
+            } else {
+              (candidates, cursor_pos - prop_name.len())
+            }
           } else {
             // combine results of declarations and globalThis properties
             let mut candidates = get_expression_property_names(
@@ -349,7 +354,12 @@ impl JupyterServer {
             candidates.sort();
             candidates.dedup(); // make sure to sort first
 
-            (candidates, cursor_pos - expr.len())
+            if expr.len() > cursor_pos {
+              // TODO(bartlomieju): most likely not correct, but better than panicking because of sub with overflow
+              (candidates, cursor_pos)
+            } else {
+              (candidates, cursor_pos - expr.len())
+            }
           };
 
           connection
diff --git a/cli/tools/lint/mod.rs b/cli/tools/lint/mod.rs
index e096b486ef..36f1cc0491 100644
--- a/cli/tools/lint/mod.rs
+++ b/cli/tools/lint/mod.rs
@@ -63,7 +63,7 @@ pub use rules::LintRuleProvider;
 
 const JSON_SCHEMA_VERSION: u8 = 1;
 
-static STDIN_FILE_NAME: &str = "$deno$stdin.ts";
+static STDIN_FILE_NAME: &str = "$deno$stdin.mts";
 
 pub async fn lint(
   flags: Arc<Flags>,
@@ -191,7 +191,7 @@ pub async fn lint(
       linter.finish()
     };
     if !success {
-      std::process::exit(1);
+      deno_runtime::exit(1);
     }
   }
 
diff --git a/cli/tools/lint/rules/mod.rs b/cli/tools/lint/rules/mod.rs
index 2669ffda15..dd723ad159 100644
--- a/cli/tools/lint/rules/mod.rs
+++ b/cli/tools/lint/rules/mod.rs
@@ -14,7 +14,7 @@ use deno_graph::ModuleGraph;
 use deno_lint::diagnostic::LintDiagnostic;
 use deno_lint::rules::LintRule;
 
-use crate::resolver::SloppyImportsResolver;
+use crate::resolver::CliSloppyImportsResolver;
 
 mod no_sloppy_imports;
 mod no_slow_types;
@@ -144,13 +144,13 @@ impl ConfiguredRules {
 }
 
 pub struct LintRuleProvider {
-  sloppy_imports_resolver: Option<Arc<SloppyImportsResolver>>,
+  sloppy_imports_resolver: Option<Arc<CliSloppyImportsResolver>>,
   workspace_resolver: Option<Arc<WorkspaceResolver>>,
 }
 
 impl LintRuleProvider {
   pub fn new(
-    sloppy_imports_resolver: Option<Arc<SloppyImportsResolver>>,
+    sloppy_imports_resolver: Option<Arc<CliSloppyImportsResolver>>,
     workspace_resolver: Option<Arc<WorkspaceResolver>>,
   ) -> Self {
     Self {
diff --git a/cli/tools/lint/rules/no_sloppy_imports.rs b/cli/tools/lint/rules/no_sloppy_imports.rs
index 4180be5be1..94bf9a7c67 100644
--- a/cli/tools/lint/rules/no_sloppy_imports.rs
+++ b/cli/tools/lint/rules/no_sloppy_imports.rs
@@ -16,24 +16,25 @@ use deno_lint::diagnostic::LintDiagnosticRange;
 use deno_lint::diagnostic::LintFix;
 use deno_lint::diagnostic::LintFixChange;
 use deno_lint::rules::LintRule;
+use deno_resolver::sloppy_imports::SloppyImportsResolution;
+use deno_resolver::sloppy_imports::SloppyImportsResolutionMode;
 use text_lines::LineAndColumnIndex;
 
 use crate::graph_util::CliJsrUrlProvider;
-use crate::resolver::SloppyImportsResolution;
-use crate::resolver::SloppyImportsResolver;
+use crate::resolver::CliSloppyImportsResolver;
 
 use super::ExtendedLintRule;
 
 #[derive(Debug)]
 pub struct NoSloppyImportsRule {
-  sloppy_imports_resolver: Option<Arc<SloppyImportsResolver>>,
+  sloppy_imports_resolver: Option<Arc<CliSloppyImportsResolver>>,
   // None for making printing out the lint rules easy
   workspace_resolver: Option<Arc<WorkspaceResolver>>,
 }
 
 impl NoSloppyImportsRule {
   pub fn new(
-    sloppy_imports_resolver: Option<Arc<SloppyImportsResolver>>,
+    sloppy_imports_resolver: Option<Arc<CliSloppyImportsResolver>>,
     workspace_resolver: Option<Arc<WorkspaceResolver>>,
   ) -> Self {
     NoSloppyImportsRule {
@@ -86,6 +87,7 @@ impl LintRule for NoSloppyImportsRule {
       captures: Default::default(),
     };
 
+    // fill this and capture the sloppy imports in the resolver
     deno_graph::parse_module_from_ast(deno_graph::ParseModuleFromAstOptions {
       graph_kind: deno_graph::GraphKind::All,
       specifier: context.specifier().clone(),
@@ -172,7 +174,7 @@ impl LintRule for NoSloppyImportsRule {
 #[derive(Debug)]
 struct SloppyImportCaptureResolver<'a> {
   workspace_resolver: &'a WorkspaceResolver,
-  sloppy_imports_resolver: &'a SloppyImportsResolver,
+  sloppy_imports_resolver: &'a CliSloppyImportsResolver,
   captures: RefCell<HashMap<Range, SloppyImportsResolution>>,
 }
 
@@ -194,7 +196,13 @@ impl<'a> deno_graph::source::Resolver for SloppyImportCaptureResolver<'a> {
       }
       | deno_config::workspace::MappedResolution::ImportMap {
         specifier, ..
-      } => match self.sloppy_imports_resolver.resolve(&specifier, mode) {
+      } => match self.sloppy_imports_resolver.resolve(
+        &specifier,
+        match mode {
+          ResolutionMode::Execution => SloppyImportsResolutionMode::Execution,
+          ResolutionMode::Types => SloppyImportsResolutionMode::Types,
+        },
+      ) {
         Some(res) => {
           self
             .captures
diff --git a/cli/tools/registry/mod.rs b/cli/tools/registry/mod.rs
index 941514b045..4098d62e37 100644
--- a/cli/tools/registry/mod.rs
+++ b/cli/tools/registry/mod.rs
@@ -43,7 +43,8 @@ use crate::cache::ParsedSourceCache;
 use crate::factory::CliFactory;
 use crate::graph_util::ModuleGraphCreator;
 use crate::http_util::HttpClient;
-use crate::resolver::SloppyImportsResolver;
+use crate::resolver::CliSloppyImportsResolver;
+use crate::resolver::SloppyImportsCachedFs;
 use crate::tools::check::CheckOptions;
 use crate::tools::lint::collect_no_slow_type_diagnostics;
 use crate::tools::registry::diagnostics::PublishDiagnostic;
@@ -108,7 +109,9 @@ pub async fn publish(
   }
   let specifier_unfurler = Arc::new(SpecifierUnfurler::new(
     if cli_options.unstable_sloppy_imports() {
-      Some(SloppyImportsResolver::new(cli_factory.fs().clone()))
+      Some(CliSloppyImportsResolver::new(SloppyImportsCachedFs::new(
+        cli_factory.fs().clone(),
+      )))
     } else {
       None
     },
diff --git a/cli/tools/registry/pm.rs b/cli/tools/registry/pm.rs
index c92710f460..68913e2591 100644
--- a/cli/tools/registry/pm.rs
+++ b/cli/tools/registry/pm.rs
@@ -1,32 +1,25 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-mod cache_deps;
-
-pub use cache_deps::cache_top_level_deps;
-use deno_semver::jsr::JsrPackageReqReference;
-use deno_semver::npm::NpmPackageReqReference;
-use deno_semver::VersionReq;
-
-use std::borrow::Cow;
+use std::path::Path;
 use std::path::PathBuf;
 use std::sync::Arc;
 
-use deno_ast::TextChange;
-use deno_config::deno_json::FmtOptionsConfig;
-use deno_core::anyhow::anyhow;
 use deno_core::anyhow::bail;
 use deno_core::anyhow::Context;
 use deno_core::error::AnyError;
 use deno_core::futures::FutureExt;
 use deno_core::futures::StreamExt;
-use deno_core::serde_json;
-use deno_core::ModuleSpecifier;
-use deno_runtime::deno_node;
+use deno_path_util::url_to_file_path;
+use deno_semver::jsr::JsrPackageReqReference;
+use deno_semver::npm::NpmPackageReqReference;
+use deno_semver::package::PackageNv;
 use deno_semver::package::PackageReq;
-use indexmap::IndexMap;
-use jsonc_parser::ast::ObjectProp;
-use jsonc_parser::ast::Value;
-use yoke::Yoke;
+use deno_semver::Version;
+use deno_semver::VersionReq;
+use jsonc_parser::cst::CstObject;
+use jsonc_parser::cst::CstObjectProp;
+use jsonc_parser::cst::CstRootNode;
+use jsonc_parser::json;
 
 use crate::args::AddFlags;
 use crate::args::CacheSetting;
@@ -38,234 +31,181 @@ use crate::file_fetcher::FileFetcher;
 use crate::jsr::JsrFetchResolver;
 use crate::npm::NpmFetchResolver;
 
-enum DenoConfigFormat {
-  Json,
-  Jsonc,
+mod cache_deps;
+
+pub use cache_deps::cache_top_level_deps;
+
+#[derive(Debug, Copy, Clone)]
+enum ConfigKind {
+  DenoJson,
+  PackageJson,
 }
 
-impl DenoConfigFormat {
-  fn from_specifier(spec: &ModuleSpecifier) -> Result<Self, AnyError> {
-    let file_name = spec
-      .path_segments()
-      .ok_or_else(|| anyhow!("Empty path in deno config specifier: {spec}"))?
-      .last()
-      .unwrap();
-    match file_name {
-      "deno.json" => Ok(Self::Json),
-      "deno.jsonc" => Ok(Self::Jsonc),
-      _ => bail!("Unsupported deno config file: {file_name}"),
-    }
-  }
-}
-
-struct DenoConfig {
-  config: Arc<deno_config::deno_json::ConfigFile>,
-  format: DenoConfigFormat,
-  imports: IndexMap<String, String>,
-}
-
-fn deno_json_imports(
-  config: &deno_config::deno_json::ConfigFile,
-) -> Result<IndexMap<String, String>, AnyError> {
-  Ok(
-    config
-      .json
-      .imports
-      .clone()
-      .map(|imports| {
-        serde_json::from_value(imports)
-          .map_err(|err| anyhow!("Malformed \"imports\" configuration: {err}"))
-      })
-      .transpose()?
-      .unwrap_or_default(),
-  )
-}
-impl DenoConfig {
-  fn from_options(options: &CliOptions) -> Result<Option<Self>, AnyError> {
-    let start_dir = &options.start_dir;
-    if let Some(config) = start_dir.maybe_deno_json() {
-      Ok(Some(Self {
-        imports: deno_json_imports(config)?,
-        config: config.clone(),
-        format: DenoConfigFormat::from_specifier(&config.specifier)?,
-      }))
-    } else {
-      Ok(None)
-    }
-  }
-
-  fn add(&mut self, selected: SelectedPackage) {
-    self.imports.insert(
-      selected.import_name,
-      format!("{}@{}", selected.package_name, selected.version_req),
-    );
-  }
-
-  fn remove(&mut self, package: &str) -> bool {
-    self.imports.shift_remove(package).is_some()
-  }
-
-  fn take_import_fields(
-    &mut self,
-  ) -> Vec<(&'static str, IndexMap<String, String>)> {
-    vec![("imports", std::mem::take(&mut self.imports))]
-  }
-}
-
-impl NpmConfig {
-  fn from_options(options: &CliOptions) -> Result<Option<Self>, AnyError> {
-    let start_dir = &options.start_dir;
-    if let Some(pkg_json) = start_dir.maybe_pkg_json() {
-      Ok(Some(Self {
-        dependencies: pkg_json.dependencies.clone().unwrap_or_default(),
-        dev_dependencies: pkg_json.dev_dependencies.clone().unwrap_or_default(),
-        config: pkg_json.clone(),
-        fmt_options: None,
-      }))
-    } else {
-      Ok(None)
-    }
-  }
-
-  fn add(&mut self, selected: SelectedPackage, dev: bool) {
-    let (name, version) = package_json_dependency_entry(selected);
-    if dev {
-      self.dev_dependencies.insert(name, version);
-    } else {
-      self.dependencies.insert(name, version);
-    }
-  }
-
-  fn remove(&mut self, package: &str) -> bool {
-    let in_deps = self.dependencies.shift_remove(package).is_some();
-    let in_dev_deps = self.dev_dependencies.shift_remove(package).is_some();
-    in_deps || in_dev_deps
-  }
-
-  fn take_import_fields(
-    &mut self,
-  ) -> Vec<(&'static str, IndexMap<String, String>)> {
-    vec![
-      ("dependencies", std::mem::take(&mut self.dependencies)),
-      (
-        "devDependencies",
-        std::mem::take(&mut self.dev_dependencies),
-      ),
-    ]
-  }
-}
-
-struct NpmConfig {
-  config: Arc<deno_node::PackageJson>,
-  fmt_options: Option<FmtOptionsConfig>,
-  dependencies: IndexMap<String, String>,
-  dev_dependencies: IndexMap<String, String>,
-}
-
-enum DenoOrPackageJson {
-  Deno(DenoConfig),
-  Npm(NpmConfig),
-}
-
-impl From<DenoConfig> for DenoOrPackageJson {
-  fn from(config: DenoConfig) -> Self {
-    Self::Deno(config)
-  }
-}
-
-impl From<NpmConfig> for DenoOrPackageJson {
-  fn from(config: NpmConfig) -> Self {
-    Self::Npm(config)
-  }
-}
-
-/// Wrapper around `jsonc_parser::ast::Object` that can be stored in a `Yoke`
-#[derive(yoke::Yokeable)]
-struct JsoncObjectView<'a>(jsonc_parser::ast::Object<'a>);
-
 struct ConfigUpdater {
-  config: DenoOrPackageJson,
-  // the `Yoke` is so we can carry the parsed object (which borrows from
-  // the source) along with the source itself
-  ast: Yoke<JsoncObjectView<'static>, String>,
+  kind: ConfigKind,
+  cst: CstRootNode,
+  root_object: CstObject,
   path: PathBuf,
   modified: bool,
 }
 
 impl ConfigUpdater {
-  fn obj(&self) -> &jsonc_parser::ast::Object<'_> {
-    &self.ast.get().0
-  }
-  fn contents(&self) -> &str {
-    self.ast.backing_cart()
-  }
-  async fn maybe_new(
-    config: Option<impl Into<DenoOrPackageJson>>,
-  ) -> Result<Option<Self>, AnyError> {
-    if let Some(config) = config {
-      Ok(Some(Self::new(config.into()).await?))
-    } else {
-      Ok(None)
-    }
-  }
-  async fn new(config: DenoOrPackageJson) -> Result<Self, AnyError> {
-    let specifier = config.specifier();
-    if specifier.scheme() != "file" {
-      bail!("Can't update a remote configuration file");
-    }
-    let config_file_path = specifier.to_file_path().map_err(|_| {
-      anyhow!("Specifier {specifier:?} is an invalid file path")
-    })?;
-    let config_file_contents = {
-      let contents = tokio::fs::read_to_string(&config_file_path)
-        .await
-        .with_context(|| {
-          format!("Reading config file at: {}", config_file_path.display())
-        })?;
-      if contents.trim().is_empty() {
-        "{}\n".into()
-      } else {
-        contents
-      }
-    };
-    let ast = Yoke::try_attach_to_cart(config_file_contents, |contents| {
-      let ast = jsonc_parser::parse_to_ast(
-        contents,
-        &Default::default(),
-        &Default::default(),
-      )
+  fn new(
+    kind: ConfigKind,
+    config_file_path: PathBuf,
+  ) -> Result<Self, AnyError> {
+    let config_file_contents = std::fs::read_to_string(&config_file_path)
       .with_context(|| {
-        format!("Failed to parse config file at {}", specifier)
+        format!("Reading config file '{}'", config_file_path.display())
       })?;
-      let obj = match ast.value {
-        Some(Value::Object(obj)) => obj,
-        _ => bail!(
-          "Failed to update config file at {}, expected an object",
-          specifier
-        ),
-      };
-      Ok(JsoncObjectView(obj))
-    })?;
+    let cst = CstRootNode::parse(&config_file_contents, &Default::default())
+      .with_context(|| {
+        format!("Parsing config file '{}'", config_file_path.display())
+      })?;
+    let root_object = cst.object_value_or_set();
     Ok(Self {
-      config,
-      ast,
+      kind,
+      cst,
+      root_object,
       path: config_file_path,
       modified: false,
     })
   }
 
+  fn display_path(&self) -> String {
+    deno_path_util::url_from_file_path(&self.path)
+      .map(|u| u.to_string())
+      .unwrap_or_else(|_| self.path.display().to_string())
+  }
+
+  fn obj(&self) -> &CstObject {
+    &self.root_object
+  }
+
+  fn contents(&self) -> String {
+    self.cst.to_string()
+  }
+
   fn add(&mut self, selected: SelectedPackage, dev: bool) {
-    match &mut self.config {
-      DenoOrPackageJson::Deno(deno) => deno.add(selected),
-      DenoOrPackageJson::Npm(npm) => npm.add(selected, dev),
+    fn insert_index(object: &CstObject, searching_name: &str) -> usize {
+      object
+        .properties()
+        .into_iter()
+        .take_while(|prop| {
+          let prop_name =
+            prop.name().and_then(|name| name.decoded_value().ok());
+          match prop_name {
+            Some(current_name) => {
+              searching_name.cmp(&current_name) == std::cmp::Ordering::Greater
+            }
+            None => true,
+          }
+        })
+        .count()
     }
+
+    match self.kind {
+      ConfigKind::DenoJson => {
+        let imports = self.root_object.object_value_or_set("imports");
+        let value =
+          format!("{}@{}", selected.package_name, selected.version_req);
+        if let Some(prop) = imports.get(&selected.import_name) {
+          prop.set_value(json!(value));
+        } else {
+          let index = insert_index(&imports, &selected.import_name);
+          imports.insert(index, &selected.import_name, json!(value));
+        }
+      }
+      ConfigKind::PackageJson => {
+        let deps_prop = self.root_object.get("dependencies");
+        let dev_deps_prop = self.root_object.get("devDependencies");
+
+        let dependencies = if dev {
+          self
+            .root_object
+            .object_value("devDependencies")
+            .unwrap_or_else(|| {
+              let index = deps_prop
+                .as_ref()
+                .map(|p| p.property_index() + 1)
+                .unwrap_or_else(|| self.root_object.properties().len());
+              self
+                .root_object
+                .insert(index, "devDependencies", json!({}))
+                .object_value_or_set()
+            })
+        } else {
+          self
+            .root_object
+            .object_value("dependencies")
+            .unwrap_or_else(|| {
+              let index = dev_deps_prop
+                .as_ref()
+                .map(|p| p.property_index())
+                .unwrap_or_else(|| self.root_object.properties().len());
+              self
+                .root_object
+                .insert(index, "dependencies", json!({}))
+                .object_value_or_set()
+            })
+        };
+        let other_dependencies = if dev {
+          deps_prop.and_then(|p| p.value().and_then(|v| v.as_object()))
+        } else {
+          dev_deps_prop.and_then(|p| p.value().and_then(|v| v.as_object()))
+        };
+
+        let (alias, value) = package_json_dependency_entry(selected);
+
+        if let Some(other) = other_dependencies {
+          if let Some(prop) = other.get(&alias) {
+            remove_prop_and_maybe_parent_prop(prop);
+          }
+        }
+
+        if let Some(prop) = dependencies.get(&alias) {
+          prop.set_value(json!(value));
+        } else {
+          let index = insert_index(&dependencies, &alias);
+          dependencies.insert(index, &alias, json!(value));
+        }
+      }
+    }
+
     self.modified = true;
   }
 
   fn remove(&mut self, package: &str) -> bool {
-    let removed = match &mut self.config {
-      DenoOrPackageJson::Deno(deno) => deno.remove(package),
-      DenoOrPackageJson::Npm(npm) => npm.remove(package),
+    let removed = match self.kind {
+      ConfigKind::DenoJson => {
+        if let Some(prop) = self
+          .root_object
+          .object_value("imports")
+          .and_then(|i| i.get(package))
+        {
+          remove_prop_and_maybe_parent_prop(prop);
+          true
+        } else {
+          false
+        }
+      }
+      ConfigKind::PackageJson => {
+        let deps = [
+          self
+            .root_object
+            .object_value("dependencies")
+            .and_then(|deps| deps.get(package)),
+          self
+            .root_object
+            .object_value("devDependencies")
+            .and_then(|deps| deps.get(package)),
+        ];
+        let removed = deps.iter().any(|d| d.is_some());
+        for dep in deps.into_iter().flatten() {
+          remove_prop_and_maybe_parent_prop(dep);
+        }
+        removed
+      }
     };
     if removed {
       self.modified = true;
@@ -273,76 +213,28 @@ impl ConfigUpdater {
     removed
   }
 
-  async fn commit(mut self) -> Result<(), AnyError> {
+  fn commit(&self) -> Result<(), AnyError> {
     if !self.modified {
       return Ok(());
     }
 
-    let import_fields = self.config.take_import_fields();
-
-    let fmt_config_options = self.config.fmt_options();
-
-    let new_text = update_config_file_content(
-      self.obj(),
-      self.contents(),
-      fmt_config_options,
-      import_fields.into_iter().map(|(k, v)| {
-        (
-          k,
-          if v.is_empty() {
-            None
-          } else {
-            Some(generate_imports(v.into_iter().collect()))
-          },
-        )
-      }),
-      self.config.file_name(),
-    );
-
-    tokio::fs::write(&self.path, new_text).await?;
+    let new_text = self.contents();
+    std::fs::write(&self.path, new_text).with_context(|| {
+      format!("failed writing to '{}'", self.path.display())
+    })?;
     Ok(())
   }
 }
 
-impl DenoOrPackageJson {
-  fn specifier(&self) -> Cow<ModuleSpecifier> {
-    match self {
-      Self::Deno(d, ..) => Cow::Borrowed(&d.config.specifier),
-      Self::Npm(n, ..) => Cow::Owned(n.config.specifier()),
-    }
-  }
-
-  fn fmt_options(&self) -> FmtOptionsConfig {
-    match self {
-      DenoOrPackageJson::Deno(deno, ..) => deno
-        .config
-        .to_fmt_config()
-        .ok()
-        .map(|f| f.options)
-        .unwrap_or_default(),
-      DenoOrPackageJson::Npm(config) => {
-        config.fmt_options.clone().unwrap_or_default()
-      }
-    }
-  }
-
-  fn take_import_fields(
-    &mut self,
-  ) -> Vec<(&'static str, IndexMap<String, String>)> {
-    match self {
-      Self::Deno(d) => d.take_import_fields(),
-      Self::Npm(n) => n.take_import_fields(),
-    }
-  }
-
-  fn file_name(&self) -> &'static str {
-    match self {
-      DenoOrPackageJson::Deno(config) => match config.format {
-        DenoConfigFormat::Json => "deno.json",
-        DenoConfigFormat::Jsonc => "deno.jsonc",
-      },
-      DenoOrPackageJson::Npm(..) => "package.json",
-    }
+fn remove_prop_and_maybe_parent_prop(prop: CstObjectProp) {
+  let parent = prop.parent().unwrap().as_object().unwrap();
+  prop.remove();
+  if parent.properties().is_empty() {
+    let parent_property = parent.parent().unwrap();
+    let root_object = parent_property.parent().unwrap().as_object().unwrap();
+    // remove the property
+    parent_property.remove();
+    root_object.ensure_multiline();
   }
 }
 
@@ -361,7 +253,14 @@ fn package_json_dependency_entry(
   selected: SelectedPackage,
 ) -> (String, String) {
   if let Some(npm_package) = selected.package_name.strip_prefix("npm:") {
-    (npm_package.into(), selected.version_req)
+    if selected.import_name == npm_package {
+      (npm_package.into(), selected.version_req)
+    } else {
+      (
+        selected.import_name,
+        format!("npm:{}@{}", npm_package, selected.version_req),
+      )
+    }
   } else if let Some(jsr_package) = selected.package_name.strip_prefix("jsr:") {
     let jsr_package = jsr_package.strip_prefix('@').unwrap_or(jsr_package);
     let scope_replaced = jsr_package.replace('/', "__");
@@ -391,21 +290,45 @@ impl std::fmt::Display for AddCommandName {
 
 fn load_configs(
   flags: &Arc<Flags>,
-) -> Result<(CliFactory, Option<NpmConfig>, Option<DenoConfig>), AnyError> {
+  has_jsr_specifiers: impl FnOnce() -> bool,
+) -> Result<(CliFactory, Option<ConfigUpdater>, Option<ConfigUpdater>), AnyError>
+{
   let cli_factory = CliFactory::from_flags(flags.clone());
   let options = cli_factory.cli_options()?;
-  let npm_config = NpmConfig::from_options(options)?;
-  let (cli_factory, deno_config) = match DenoConfig::from_options(options)? {
+  let start_dir = &options.start_dir;
+  let npm_config = match start_dir.maybe_pkg_json() {
+    Some(pkg_json) => Some(ConfigUpdater::new(
+      ConfigKind::PackageJson,
+      pkg_json.path.clone(),
+    )?),
+    None => None,
+  };
+  let deno_config = match start_dir.maybe_deno_json() {
+    Some(deno_json) => Some(ConfigUpdater::new(
+      ConfigKind::DenoJson,
+      url_to_file_path(&deno_json.specifier)?,
+    )?),
+    None => None,
+  };
+
+  let (cli_factory, deno_config) = match deno_config {
     Some(config) => (cli_factory, Some(config)),
-    None if npm_config.is_some() => (cli_factory, None),
-    None => {
+    None if npm_config.is_some() && !has_jsr_specifiers() => {
+      (cli_factory, None)
+    }
+    _ => {
       let factory = create_deno_json(flags, options)?;
       let options = factory.cli_options()?.clone();
+      let deno_json = options
+        .start_dir
+        .maybe_deno_json()
+        .expect("Just created deno.json");
       (
         factory,
-        Some(
-          DenoConfig::from_options(&options)?.expect("Just created deno.json"),
-        ),
+        Some(ConfigUpdater::new(
+          ConfigKind::DenoJson,
+          url_to_file_path(&deno_json.specifier)?,
+        )?),
       )
     }
   };
@@ -413,18 +336,26 @@ fn load_configs(
   Ok((cli_factory, npm_config, deno_config))
 }
 
+fn path_distance(a: &Path, b: &Path) -> usize {
+  let diff = pathdiff::diff_paths(a, b);
+  let Some(diff) = diff else {
+    return usize::MAX;
+  };
+  diff.components().count()
+}
+
 pub async fn add(
   flags: Arc<Flags>,
   add_flags: AddFlags,
   cmd_name: AddCommandName,
 ) -> Result<(), AnyError> {
-  let (cli_factory, npm_config, deno_config) = load_configs(&flags)?;
-  let mut npm_config = ConfigUpdater::maybe_new(npm_config).await?;
-  let mut deno_config = ConfigUpdater::maybe_new(deno_config).await?;
+  let (cli_factory, mut npm_config, mut deno_config) =
+    load_configs(&flags, || {
+      add_flags.packages.iter().any(|s| s.starts_with("jsr:"))
+    })?;
 
   if let Some(deno) = &deno_config {
-    let specifier = deno.config.specifier();
-    if deno.obj().get_string("importMap").is_some() {
+    if deno.obj().get("importMap").is_some() {
       bail!(
         concat!(
           "`deno {}` is not supported when configuration file contains an \"importMap\" field. ",
@@ -432,11 +363,26 @@ pub async fn add(
           "    at {}",
         ),
         cmd_name,
-        specifier
+        deno.display_path(),
       );
     }
   }
 
+  let start_dir = cli_factory.cli_options()?.start_dir.dir_path();
+
+  // only prefer to add npm deps to `package.json` if there isn't a closer deno.json.
+  // example: if deno.json is in the CWD and package.json is in the parent, we should add
+  // npm deps to deno.json, since it's closer
+  let prefer_npm_config = match (npm_config.as_ref(), deno_config.as_ref()) {
+    (Some(npm), Some(deno)) => {
+      let npm_distance = path_distance(&npm.path, &start_dir);
+      let deno_distance = path_distance(&deno.path, &start_dir);
+      npm_distance <= deno_distance
+    }
+    (Some(_), None) => true,
+    (None, _) => false,
+  };
+
   let http_client = cli_factory.http_client_provider();
   let deps_http_cache = cli_factory.global_http_cache()?;
   let mut deps_file_fetcher = FileFetcher::new(
@@ -447,16 +393,20 @@ pub async fn add(
     Default::default(),
     None,
   );
+
+  let npmrc = cli_factory.cli_options().unwrap().npmrc();
+
   deps_file_fetcher.set_download_log_level(log::Level::Trace);
   let deps_file_fetcher = Arc::new(deps_file_fetcher);
   let jsr_resolver = Arc::new(JsrFetchResolver::new(deps_file_fetcher.clone()));
-  let npm_resolver = Arc::new(NpmFetchResolver::new(deps_file_fetcher));
+  let npm_resolver =
+    Arc::new(NpmFetchResolver::new(deps_file_fetcher, npmrc.clone()));
 
   let mut selected_packages = Vec::with_capacity(add_flags.packages.len());
   let mut package_reqs = Vec::with_capacity(add_flags.packages.len());
 
   for entry_text in add_flags.packages.iter() {
-    let req = AddPackageReq::parse(entry_text).with_context(|| {
+    let req = AddRmPackageReq::parse(entry_text).with_context(|| {
       format!("Failed to parse package required: {}", entry_text)
     })?;
 
@@ -507,15 +457,32 @@ pub async fn add(
     match package_and_version {
       PackageAndVersion::NotFound {
         package: package_name,
-        found_npm_package,
+        help,
         package_req,
-      } => {
-        if found_npm_package {
-          bail!("{} was not found, but a matching npm package exists. Did you mean `{}`?", crate::colors::red(package_name), crate::colors::yellow(format!("deno {cmd_name} npm:{package_req}")));
-        } else {
-          bail!("{} was not found.", crate::colors::red(package_name));
+      } => match help {
+        Some(NotFoundHelp::NpmPackage) => {
+          bail!(
+            "{} was not found, but a matching npm package exists. Did you mean `{}`?",
+            crate::colors::red(package_name),
+            crate::colors::yellow(format!("deno {cmd_name} npm:{package_req}"))
+          );
         }
-      }
+        Some(NotFoundHelp::JsrPackage) => {
+          bail!(
+            "{} was not found, but a matching jsr package exists. Did you mean `{}`?",
+            crate::colors::red(package_name),
+            crate::colors::yellow(format!("deno {cmd_name} jsr:{package_req}"))
+          )
+        }
+        Some(NotFoundHelp::PreReleaseVersion(version)) => {
+          bail!(
+            "{} has only pre-release versions available. Try specifying a version: `{}`",
+            crate::colors::red(&package_name),
+            crate::colors::yellow(format!("deno {cmd_name} {package_name}@^{version}"))
+          )
+        }
+        None => bail!("{} was not found.", crate::colors::red(package_name)),
+      },
       PackageAndVersion::Selected(selected) => {
         selected_packages.push(selected);
       }
@@ -531,7 +498,7 @@ pub async fn add(
       selected_package.selected_version
     );
 
-    if selected_package.package_name.starts_with("npm:") {
+    if selected_package.package_name.starts_with("npm:") && prefer_npm_config {
       if let Some(npm) = &mut npm_config {
         npm.add(selected_package, dev);
       } else {
@@ -544,26 +511,14 @@ pub async fn add(
     }
   }
 
-  let mut commit_futures = vec![];
   if let Some(npm) = npm_config {
-    commit_futures.push(npm.commit());
+    npm.commit()?;
   }
   if let Some(deno) = deno_config {
-    commit_futures.push(deno.commit());
-  }
-  let commit_futures =
-    deno_core::futures::future::join_all(commit_futures).await;
-
-  for result in commit_futures {
-    result.context("Failed to update configuration file")?;
+    deno.commit()?;
   }
 
-  // clear the previously cached package.json from memory before reloading it
-  node_resolver::PackageJsonThreadLocalCache::clear();
-  // make a new CliFactory to pick up the updated config file
-  let cli_factory = CliFactory::from_flags(flags);
-  // cache deps
-  cache_deps::cache_top_level_deps(&cli_factory, Some(jsr_resolver)).await?;
+  npm_install_after_modification(flags, Some(jsr_resolver)).await?;
 
   Ok(())
 }
@@ -575,87 +530,161 @@ struct SelectedPackage {
   selected_version: String,
 }
 
+enum NotFoundHelp {
+  NpmPackage,
+  JsrPackage,
+  PreReleaseVersion(Version),
+}
+
 enum PackageAndVersion {
   NotFound {
     package: String,
-    found_npm_package: bool,
     package_req: PackageReq,
+    help: Option<NotFoundHelp>,
   },
   Selected(SelectedPackage),
 }
 
+fn best_version<'a>(
+  versions: impl Iterator<Item = &'a Version>,
+) -> Option<&'a Version> {
+  let mut maybe_best_version: Option<&Version> = None;
+  for version in versions {
+    let is_best_version = maybe_best_version
+      .as_ref()
+      .map(|best_version| (*best_version).cmp(version).is_lt())
+      .unwrap_or(true);
+    if is_best_version {
+      maybe_best_version = Some(version);
+    }
+  }
+  maybe_best_version
+}
+
+trait PackageInfoProvider {
+  const SPECIFIER_PREFIX: &str;
+  /// The help to return if a package is found by this provider
+  const HELP: NotFoundHelp;
+  async fn req_to_nv(&self, req: &PackageReq) -> Option<PackageNv>;
+  async fn latest_version<'a>(&self, req: &PackageReq) -> Option<Version>;
+}
+
+impl PackageInfoProvider for Arc<JsrFetchResolver> {
+  const HELP: NotFoundHelp = NotFoundHelp::JsrPackage;
+  const SPECIFIER_PREFIX: &str = "jsr";
+  async fn req_to_nv(&self, req: &PackageReq) -> Option<PackageNv> {
+    (**self).req_to_nv(req).await
+  }
+
+  async fn latest_version<'a>(&self, req: &PackageReq) -> Option<Version> {
+    let info = self.package_info(&req.name).await?;
+    best_version(
+      info
+        .versions
+        .iter()
+        .filter(|(_, version_info)| !version_info.yanked)
+        .map(|(version, _)| version),
+    )
+    .cloned()
+  }
+}
+
+impl PackageInfoProvider for Arc<NpmFetchResolver> {
+  const HELP: NotFoundHelp = NotFoundHelp::NpmPackage;
+  const SPECIFIER_PREFIX: &str = "npm";
+  async fn req_to_nv(&self, req: &PackageReq) -> Option<PackageNv> {
+    (**self).req_to_nv(req).await
+  }
+
+  async fn latest_version<'a>(&self, req: &PackageReq) -> Option<Version> {
+    let info = self.package_info(&req.name).await?;
+    best_version(info.versions.keys()).cloned()
+  }
+}
+
 async fn find_package_and_select_version_for_req(
   jsr_resolver: Arc<JsrFetchResolver>,
   npm_resolver: Arc<NpmFetchResolver>,
-  add_package_req: AddPackageReq,
+  add_package_req: AddRmPackageReq,
 ) -> Result<PackageAndVersion, AnyError> {
-  match add_package_req.value {
-    AddPackageReqValue::Jsr(req) => {
-      let jsr_prefixed_name = format!("jsr:{}", &req.name);
-      let Some(nv) = jsr_resolver.req_to_nv(&req).await else {
-        if npm_resolver.req_to_nv(&req).await.is_some() {
+  async fn select<T: PackageInfoProvider, S: PackageInfoProvider>(
+    main_resolver: T,
+    fallback_resolver: S,
+    add_package_req: AddRmPackageReq,
+  ) -> Result<PackageAndVersion, AnyError> {
+    let req = match &add_package_req.value {
+      AddRmPackageReqValue::Jsr(req) => req,
+      AddRmPackageReqValue::Npm(req) => req,
+    };
+    let prefixed_name = format!("{}:{}", T::SPECIFIER_PREFIX, req.name);
+    let help_if_found_in_fallback = S::HELP;
+    let Some(nv) = main_resolver.req_to_nv(req).await else {
+      if fallback_resolver.req_to_nv(req).await.is_some() {
+        // it's in the other registry
+        return Ok(PackageAndVersion::NotFound {
+          package: prefixed_name,
+          help: Some(help_if_found_in_fallback),
+          package_req: req.clone(),
+        });
+      }
+      if req.version_req.version_text() == "*" {
+        if let Some(pre_release_version) =
+          main_resolver.latest_version(req).await
+        {
           return Ok(PackageAndVersion::NotFound {
-            package: jsr_prefixed_name,
-            found_npm_package: true,
-            package_req: req,
+            package: prefixed_name,
+            package_req: req.clone(),
+            help: Some(NotFoundHelp::PreReleaseVersion(
+              pre_release_version.clone(),
+            )),
           });
         }
+      }
 
-        return Ok(PackageAndVersion::NotFound {
-          package: jsr_prefixed_name,
-          found_npm_package: false,
-          package_req: req,
-        });
-      };
-      let range_symbol = if req.version_req.version_text().starts_with('~') {
-        '~'
-      } else {
-        '^'
-      };
-      Ok(PackageAndVersion::Selected(SelectedPackage {
-        import_name: add_package_req.alias,
-        package_name: jsr_prefixed_name,
-        version_req: format!("{}{}", range_symbol, &nv.version),
-        selected_version: nv.version.to_string(),
-      }))
+      return Ok(PackageAndVersion::NotFound {
+        package: prefixed_name,
+        help: None,
+        package_req: req.clone(),
+      });
+    };
+    let range_symbol = if req.version_req.version_text().starts_with('~') {
+      "~"
+    } else if req.version_req.version_text() == nv.version.to_string() {
+      ""
+    } else {
+      "^"
+    };
+    Ok(PackageAndVersion::Selected(SelectedPackage {
+      import_name: add_package_req.alias,
+      package_name: prefixed_name,
+      version_req: format!("{}{}", range_symbol, &nv.version),
+      selected_version: nv.version.to_string(),
+    }))
+  }
+
+  match &add_package_req.value {
+    AddRmPackageReqValue::Jsr(_) => {
+      select(jsr_resolver, npm_resolver, add_package_req).await
     }
-    AddPackageReqValue::Npm(req) => {
-      let npm_prefixed_name = format!("npm:{}", &req.name);
-      let Some(nv) = npm_resolver.req_to_nv(&req).await else {
-        return Ok(PackageAndVersion::NotFound {
-          package: npm_prefixed_name,
-          found_npm_package: false,
-          package_req: req,
-        });
-      };
-      let range_symbol = if req.version_req.version_text().starts_with('~') {
-        '~'
-      } else {
-        '^'
-      };
-      Ok(PackageAndVersion::Selected(SelectedPackage {
-        import_name: add_package_req.alias,
-        package_name: npm_prefixed_name,
-        version_req: format!("{}{}", range_symbol, &nv.version),
-        selected_version: nv.version.to_string(),
-      }))
+    AddRmPackageReqValue::Npm(_) => {
+      select(npm_resolver, jsr_resolver, add_package_req).await
     }
   }
 }
 
 #[derive(Debug, PartialEq, Eq)]
-enum AddPackageReqValue {
+enum AddRmPackageReqValue {
   Jsr(PackageReq),
   Npm(PackageReq),
 }
 
 #[derive(Debug, PartialEq, Eq)]
-struct AddPackageReq {
+struct AddRmPackageReq {
   alias: String,
-  value: AddPackageReqValue,
+  value: AddRmPackageReqValue,
 }
 
-impl AddPackageReq {
+impl AddRmPackageReq {
   pub fn parse(entry_text: &str) -> Result<Result<Self, PackageReq>, AnyError> {
     enum Prefix {
       Jsr,
@@ -710,9 +739,9 @@ impl AddPackageReq {
         let req_ref =
           JsrPackageReqReference::from_str(&format!("jsr:{}", entry_text))?;
         let package_req = req_ref.into_inner().req;
-        Ok(Ok(AddPackageReq {
+        Ok(Ok(AddRmPackageReq {
           alias: maybe_alias.unwrap_or_else(|| package_req.name.to_string()),
-          value: AddPackageReqValue::Jsr(package_req),
+          value: AddRmPackageReqValue::Jsr(package_req),
         }))
       }
       Prefix::Npm => {
@@ -730,49 +759,48 @@ impl AddPackageReq {
             deno_semver::RangeSetOrTag::Tag("latest".into()),
           );
         }
-        Ok(Ok(AddPackageReq {
+        Ok(Ok(AddRmPackageReq {
           alias: maybe_alias.unwrap_or_else(|| package_req.name.to_string()),
-          value: AddPackageReqValue::Npm(package_req),
+          value: AddRmPackageReqValue::Npm(package_req),
         }))
       }
     }
   }
 }
 
-fn generate_imports(mut packages_to_version: Vec<(String, String)>) -> String {
-  packages_to_version.sort_by(|(k1, _), (k2, _)| k1.cmp(k2));
-  let mut contents = vec![];
-  let len = packages_to_version.len();
-  for (index, (package, version)) in packages_to_version.iter().enumerate() {
-    // TODO(bartlomieju): fix it, once we start support specifying version on the cli
-    contents.push(format!("\"{}\": \"{}\"", package, version));
-    if index != len - 1 {
-      contents.push(",".to_string());
-    }
-  }
-  contents.join("\n")
-}
-
 pub async fn remove(
   flags: Arc<Flags>,
   remove_flags: RemoveFlags,
 ) -> Result<(), AnyError> {
-  let (_, npm_config, deno_config) = load_configs(&flags)?;
+  let (_, npm_config, deno_config) = load_configs(&flags, || false)?;
 
-  let mut configs = [
-    ConfigUpdater::maybe_new(npm_config).await?,
-    ConfigUpdater::maybe_new(deno_config).await?,
-  ];
+  let mut configs = [npm_config, deno_config];
 
   let mut removed_packages = vec![];
 
   for package in &remove_flags.packages {
-    let mut removed = false;
+    let req = AddRmPackageReq::parse(package).with_context(|| {
+      format!("Failed to parse package required: {}", package)
+    })?;
+    let mut parsed_pkg_name = None;
     for config in configs.iter_mut().flatten() {
-      removed |= config.remove(package);
+      match &req {
+        Ok(rm_pkg) => {
+          if config.remove(&rm_pkg.alias) && parsed_pkg_name.is_none() {
+            parsed_pkg_name = Some(rm_pkg.alias.clone());
+          }
+        }
+        Err(pkg) => {
+          // An alias or a package name without registry/version
+          // constraints. Try to remove the package anyway.
+          if config.remove(&pkg.name) && parsed_pkg_name.is_none() {
+            parsed_pkg_name = Some(pkg.name.clone());
+          }
+        }
+      }
     }
-    if removed {
-      removed_packages.push(package.clone());
+    if let Some(pkg) = parsed_pkg_name {
+      removed_packages.push(pkg);
     }
   }
 
@@ -783,97 +811,38 @@ pub async fn remove(
       log::info!("Removed {}", crate::colors::green(package));
     }
     for config in configs.into_iter().flatten() {
-      config.commit().await?;
+      config.commit()?;
     }
 
-    // Update deno.lock
-    node_resolver::PackageJsonThreadLocalCache::clear();
-    let cli_factory = CliFactory::from_flags(flags);
-    cache_deps::cache_top_level_deps(&cli_factory, None).await?;
+    npm_install_after_modification(flags, None).await?;
   }
 
   Ok(())
 }
 
-fn update_config_file_content<
-  I: IntoIterator<Item = (&'static str, Option<String>)>,
->(
-  obj: &jsonc_parser::ast::Object,
-  config_file_contents: &str,
-  fmt_options: FmtOptionsConfig,
-  entries: I,
-  file_name: &str,
-) -> String {
-  let mut text_changes = vec![];
-  for (key, value) in entries {
-    match obj.properties.iter().enumerate().find_map(|(idx, k)| {
-      if k.name.as_str() == key {
-        Some((idx, k))
-      } else {
-        None
-      }
-    }) {
-      Some((
-        idx,
-        ObjectProp {
-          value: Value::Object(lit),
-          range,
-          ..
-        },
-      )) => {
-        if let Some(value) = value {
-          text_changes.push(TextChange {
-            range: (lit.range.start + 1)..(lit.range.end - 1),
-            new_text: value,
-          })
-        } else {
-          text_changes.push(TextChange {
-            // remove field entirely, making sure to
-            // remove the comma if it's not the last field
-            range: range.start..(if idx == obj.properties.len() - 1 {
-              range.end
-            } else {
-              obj.properties[idx + 1].range.start
-            }),
-            new_text: "".to_string(),
-          })
-        }
-      }
+async fn npm_install_after_modification(
+  flags: Arc<Flags>,
+  // explicitly provided to prevent redownloading
+  jsr_resolver: Option<Arc<crate::jsr::JsrFetchResolver>>,
+) -> Result<(), AnyError> {
+  // clear the previously cached package.json from memory before reloading it
+  node_resolver::PackageJsonThreadLocalCache::clear();
 
-      // need to add field
-      None => {
-        if let Some(value) = value {
-          let insert_position = obj.range.end - 1;
-          text_changes.push(TextChange {
-            range: insert_position..insert_position,
-            // NOTE(bartlomieju): adding `\n` here to force the formatter to always
-            // produce a config file that is multiline, like so:
-            // ```
-            // {
-            //   "imports": {
-            //     "<package_name>": "<registry>:<package_name>@<semver>"
-            //   }
-            // }
-            new_text: format!("\"{key}\": {{\n {value} }}"),
-          })
-        }
-      }
-      // we verified the shape of `imports`/`dependencies` above
-      Some(_) => unreachable!(),
-    }
+  // make a new CliFactory to pick up the updated config file
+  let cli_factory = CliFactory::from_flags(flags);
+  // surface any errors in the package.json
+  let npm_resolver = cli_factory.npm_resolver().await?;
+  if let Some(npm_resolver) = npm_resolver.as_managed() {
+    npm_resolver.ensure_no_pkg_json_dep_errors()?;
+  }
+  // npm install
+  cache_deps::cache_top_level_deps(&cli_factory, jsr_resolver).await?;
+
+  if let Some(lockfile) = cli_factory.cli_options()?.maybe_lockfile() {
+    lockfile.write_if_changed()?;
   }
 
-  let new_text =
-    deno_ast::apply_text_changes(config_file_contents, text_changes);
-
-  crate::tools::fmt::format_json(
-    &PathBuf::from(file_name),
-    &new_text,
-    &fmt_options,
-  )
-  .ok()
-  .map(|formatted_text| formatted_text.unwrap_or_else(|| new_text.clone()))
-  .unwrap_or(new_text)
+  Ok(())
 }
 
 #[cfg(test)]
@@ -883,48 +852,52 @@ mod test {
   #[test]
   fn test_parse_add_package_req() {
     assert_eq!(
-      AddPackageReq::parse("jsr:foo").unwrap().unwrap(),
-      AddPackageReq {
+      AddRmPackageReq::parse("jsr:foo").unwrap().unwrap(),
+      AddRmPackageReq {
         alias: "foo".to_string(),
-        value: AddPackageReqValue::Jsr(PackageReq::from_str("foo").unwrap())
+        value: AddRmPackageReqValue::Jsr(PackageReq::from_str("foo").unwrap())
       }
     );
     assert_eq!(
-      AddPackageReq::parse("alias@jsr:foo").unwrap().unwrap(),
-      AddPackageReq {
+      AddRmPackageReq::parse("alias@jsr:foo").unwrap().unwrap(),
+      AddRmPackageReq {
         alias: "alias".to_string(),
-        value: AddPackageReqValue::Jsr(PackageReq::from_str("foo").unwrap())
+        value: AddRmPackageReqValue::Jsr(PackageReq::from_str("foo").unwrap())
       }
     );
     assert_eq!(
-      AddPackageReq::parse("@alias/pkg@npm:foo").unwrap().unwrap(),
-      AddPackageReq {
+      AddRmPackageReq::parse("@alias/pkg@npm:foo")
+        .unwrap()
+        .unwrap(),
+      AddRmPackageReq {
         alias: "@alias/pkg".to_string(),
-        value: AddPackageReqValue::Npm(
+        value: AddRmPackageReqValue::Npm(
           PackageReq::from_str("foo@latest").unwrap()
         )
       }
     );
     assert_eq!(
-      AddPackageReq::parse("@alias/pkg@jsr:foo").unwrap().unwrap(),
-      AddPackageReq {
+      AddRmPackageReq::parse("@alias/pkg@jsr:foo")
+        .unwrap()
+        .unwrap(),
+      AddRmPackageReq {
         alias: "@alias/pkg".to_string(),
-        value: AddPackageReqValue::Jsr(PackageReq::from_str("foo").unwrap())
+        value: AddRmPackageReqValue::Jsr(PackageReq::from_str("foo").unwrap())
       }
     );
     assert_eq!(
-      AddPackageReq::parse("alias@jsr:foo@^1.5.0")
+      AddRmPackageReq::parse("alias@jsr:foo@^1.5.0")
         .unwrap()
         .unwrap(),
-      AddPackageReq {
+      AddRmPackageReq {
         alias: "alias".to_string(),
-        value: AddPackageReqValue::Jsr(
+        value: AddRmPackageReqValue::Jsr(
           PackageReq::from_str("foo@^1.5.0").unwrap()
         )
       }
     );
     assert_eq!(
-      AddPackageReq::parse("@scope/pkg@tag")
+      AddRmPackageReq::parse("@scope/pkg@tag")
         .unwrap()
         .unwrap_err()
         .to_string(),
diff --git a/cli/tools/registry/pm/cache_deps.rs b/cli/tools/registry/pm/cache_deps.rs
index 7d1773b343..d3c8da868c 100644
--- a/cli/tools/registry/pm/cache_deps.rs
+++ b/cli/tools/registry/pm/cache_deps.rs
@@ -11,6 +11,7 @@ use deno_core::futures::StreamExt;
 use deno_semver::package::PackageReq;
 
 pub async fn cache_top_level_deps(
+  // todo(dsherret): don't pass the factory into this function. Instead use ctor deps
   factory: &CliFactory,
   jsr_resolver: Option<Arc<crate::jsr::JsrFetchResolver>>,
 ) -> Result<(), AnyError> {
@@ -43,7 +44,11 @@ pub async fn cache_top_level_deps(
 
     let mut seen_reqs = std::collections::HashSet::new();
 
-    for entry in import_map.imports().entries() {
+    for entry in import_map.imports().entries().chain(
+      import_map
+        .scopes()
+        .flat_map(|scope| scope.imports.entries()),
+    ) {
       let Some(specifier) = entry.value else {
         continue;
       };
@@ -74,6 +79,13 @@ pub async fn cache_top_level_deps(
           if entry.key.ends_with('/') && specifier.as_str().ends_with('/') {
             continue;
           }
+          if specifier.scheme() == "file" {
+            if let Ok(path) = specifier.to_file_path() {
+              if !path.is_file() {
+                continue;
+              }
+            }
+          }
           roots.push(specifier.clone());
         }
       }
@@ -81,10 +93,6 @@ pub async fn cache_top_level_deps(
 
     while let Some(info_future) = info_futures.next().await {
       if let Some((specifier, info)) = info_future {
-        if info.export(".").is_some() {
-          roots.push(specifier.clone());
-          continue;
-        }
         let exports = info.exports();
         for (k, _) in exports {
           if let Ok(spec) = specifier.join(k) {
diff --git a/cli/tools/registry/tar.rs b/cli/tools/registry/tar.rs
index aca125e00b..6d1801ce69 100644
--- a/cli/tools/registry/tar.rs
+++ b/cli/tools/registry/tar.rs
@@ -120,7 +120,7 @@ fn resolve_content_maybe_unfurling(
         | MediaType::Unknown
         | MediaType::Json
         | MediaType::Wasm
-        | MediaType::TsBuildInfo => {
+        | MediaType::Css => {
           // not unfurlable data
           return Ok(data);
         }
diff --git a/cli/tools/registry/unfurl.rs b/cli/tools/registry/unfurl.rs
index 0f5b9fdd32..5ec726a640 100644
--- a/cli/tools/registry/unfurl.rs
+++ b/cli/tools/registry/unfurl.rs
@@ -12,9 +12,10 @@ use deno_graph::DynamicTemplatePart;
 use deno_graph::ParserModuleAnalyzer;
 use deno_graph::TypeScriptReference;
 use deno_package_json::PackageJsonDepValue;
+use deno_resolver::sloppy_imports::SloppyImportsResolutionMode;
 use deno_runtime::deno_node::is_builtin_node_module;
 
-use crate::resolver::SloppyImportsResolver;
+use crate::resolver::CliSloppyImportsResolver;
 
 #[derive(Debug, Clone)]
 pub enum SpecifierUnfurlerDiagnostic {
@@ -42,14 +43,14 @@ impl SpecifierUnfurlerDiagnostic {
 }
 
 pub struct SpecifierUnfurler {
-  sloppy_imports_resolver: Option<SloppyImportsResolver>,
+  sloppy_imports_resolver: Option<CliSloppyImportsResolver>,
   workspace_resolver: WorkspaceResolver,
   bare_node_builtins: bool,
 }
 
 impl SpecifierUnfurler {
   pub fn new(
-    sloppy_imports_resolver: Option<SloppyImportsResolver>,
+    sloppy_imports_resolver: Option<CliSloppyImportsResolver>,
     workspace_resolver: WorkspaceResolver,
     bare_node_builtins: bool,
   ) -> Self {
@@ -179,7 +180,7 @@ impl SpecifierUnfurler {
     let resolved =
       if let Some(sloppy_imports_resolver) = &self.sloppy_imports_resolver {
         sloppy_imports_resolver
-          .resolve(&resolved, deno_graph::source::ResolutionMode::Execution)
+          .resolve(&resolved, SloppyImportsResolutionMode::Execution)
           .map(|res| res.into_specifier())
           .unwrap_or(resolved)
       } else {
@@ -388,6 +389,8 @@ fn to_range(
 mod tests {
   use std::sync::Arc;
 
+  use crate::resolver::SloppyImportsCachedFs;
+
   use super::*;
   use deno_ast::MediaType;
   use deno_ast::ModuleSpecifier;
@@ -455,7 +458,9 @@ mod tests {
     );
     let fs = Arc::new(RealFs);
     let unfurler = SpecifierUnfurler::new(
-      Some(SloppyImportsResolver::new(fs)),
+      Some(CliSloppyImportsResolver::new(SloppyImportsCachedFs::new(
+        fs,
+      ))),
       workspace_resolver,
       true,
     );
diff --git a/cli/tools/repl/session.rs b/cli/tools/repl/session.rs
index 484664dae4..8e05c4abbc 100644
--- a/cli/tools/repl/session.rs
+++ b/cli/tools/repl/session.rs
@@ -7,7 +7,7 @@ use crate::cdp;
 use crate::colors;
 use crate::lsp::ReplLanguageServer;
 use crate::npm::CliNpmResolver;
-use crate::resolver::CliGraphResolver;
+use crate::resolver::CliResolver;
 use crate::tools::test::report_tests;
 use crate::tools::test::reporters::PrettyTestReporter;
 use crate::tools::test::reporters::TestReporter;
@@ -25,6 +25,7 @@ use deno_ast::swc::visit::noop_visit_type;
 use deno_ast::swc::visit::Visit;
 use deno_ast::swc::visit::VisitWith;
 use deno_ast::ImportsNotUsedAsValues;
+use deno_ast::ModuleKind;
 use deno_ast::ModuleSpecifier;
 use deno_ast::ParseDiagnosticsError;
 use deno_ast::ParsedSource;
@@ -43,12 +44,12 @@ use deno_core::url::Url;
 use deno_core::LocalInspectorSession;
 use deno_core::PollEventLoopOptions;
 use deno_graph::source::ResolutionMode;
-use deno_graph::source::Resolver;
 use deno_graph::Position;
 use deno_graph::PositionRange;
 use deno_graph::SpecifierWithRange;
 use deno_runtime::worker::MainWorker;
 use deno_semver::npm::NpmPackageReqReference;
+use node_resolver::NodeModuleKind;
 use once_cell::sync::Lazy;
 use regex::Match;
 use regex::Regex;
@@ -179,7 +180,7 @@ struct ReplJsxState {
 
 pub struct ReplSession {
   npm_resolver: Arc<dyn CliNpmResolver>,
-  resolver: Arc<CliGraphResolver>,
+  resolver: Arc<CliResolver>,
   pub worker: MainWorker,
   session: LocalInspectorSession,
   pub context_id: u64,
@@ -198,7 +199,7 @@ impl ReplSession {
   pub async fn initialize(
     cli_options: &CliOptions,
     npm_resolver: Arc<dyn CliNpmResolver>,
-    resolver: Arc<CliGraphResolver>,
+    resolver: Arc<CliResolver>,
     mut worker: MainWorker,
     main_module: ModuleSpecifier,
     test_event_receiver: TestEventReceiver,
@@ -244,7 +245,7 @@ impl ReplSession {
     assert_ne!(context_id, 0);
 
     let referrer =
-      deno_core::resolve_path("./$deno$repl.ts", cli_options.initial_cwd())
+      deno_core::resolve_path("./$deno$repl.mts", cli_options.initial_cwd())
         .unwrap();
 
     let cwd_url =
@@ -641,6 +642,10 @@ impl ReplSession {
           jsx_fragment_factory: self.jsx.frag_factory.clone(),
           jsx_import_source: self.jsx.import_source.clone(),
           var_decl_imports: true,
+          verbatim_module_syntax: false,
+        },
+        &deno_ast::TranspileModuleOptions {
+          module_kind: Some(ModuleKind::Esm),
         },
         &deno_ast::EmitOptions {
           source_map: deno_ast::SourceMapOption::None,
@@ -651,7 +656,6 @@ impl ReplSession {
         },
       )?
       .into_source()
-      .into_string()?
       .text;
 
     let value = self
@@ -708,7 +712,12 @@ impl ReplSession {
       .flat_map(|i| {
         self
           .resolver
-          .resolve(i, &referrer_range, ResolutionMode::Execution)
+          .resolve(
+            i,
+            &referrer_range,
+            NodeModuleKind::Esm,
+            ResolutionMode::Execution,
+          )
           .ok()
           .or_else(|| ModuleSpecifier::parse(i).ok())
       })
diff --git a/cli/tools/run/hmr.rs b/cli/tools/run/hmr.rs
index 6ccf8e344b..373c207d69 100644
--- a/cli/tools/run/hmr.rs
+++ b/cli/tools/run/hmr.rs
@@ -1,9 +1,9 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use crate::cdp;
-use crate::emit::Emitter;
-use crate::util::file_watcher::WatcherCommunicator;
-use crate::util::file_watcher::WatcherRestartMode;
+use std::collections::HashMap;
+use std::path::PathBuf;
+use std::sync::Arc;
+
 use deno_core::error::generic_error;
 use deno_core::error::AnyError;
 use deno_core::futures::StreamExt;
@@ -12,11 +12,13 @@ use deno_core::serde_json::{self};
 use deno_core::url::Url;
 use deno_core::LocalInspectorSession;
 use deno_terminal::colors;
-use std::collections::HashMap;
-use std::path::PathBuf;
-use std::sync::Arc;
 use tokio::select;
 
+use crate::cdp;
+use crate::emit::Emitter;
+use crate::util::file_watcher::WatcherCommunicator;
+use crate::util::file_watcher::WatcherRestartMode;
+
 fn explain(status: &cdp::Status) -> &'static str {
   match status {
     cdp::Status::Ok => "OK",
@@ -139,7 +141,7 @@ impl crate::worker::HmrRunner for HmrRunner {
             };
 
             let source_code = self.emitter.load_and_emit_for_hmr(
-              &module_url
+              &module_url,
             ).await?;
 
             let mut tries = 1;
diff --git a/cli/tools/run/mod.rs b/cli/tools/run/mod.rs
index 152e2650bd..bebb3f5881 100644
--- a/cli/tools/run/mod.rs
+++ b/cli/tools/run/mod.rs
@@ -30,6 +30,16 @@ To grant permissions, set them before the script argument. For example:
   }
 }
 
+fn set_npm_user_agent() {
+  static ONCE: std::sync::Once = std::sync::Once::new();
+  ONCE.call_once(|| {
+    std::env::set_var(
+      crate::npm::NPM_CONFIG_USER_AGENT_ENV_VAR,
+      crate::npm::get_npm_config_user_agent(),
+    );
+  });
+}
+
 pub async fn run_script(
   mode: WorkerExecutionMode,
   flags: Arc<Flags>,
@@ -58,6 +68,10 @@ pub async fn run_script(
 
   let main_module = cli_options.resolve_main_module()?;
 
+  if main_module.scheme() == "npm" {
+    set_npm_user_agent();
+  }
+
   maybe_npm_install(&factory).await?;
 
   let worker_factory = factory.create_cli_main_worker_factory().await?;
@@ -119,6 +133,10 @@ async fn run_with_watch(
         let cli_options = factory.cli_options()?;
         let main_module = cli_options.resolve_main_module()?;
 
+        if main_module.scheme() == "npm" {
+          set_npm_user_agent();
+        }
+
         maybe_npm_install(&factory).await?;
 
         let _ = watcher_communicator.watch_paths(cli_options.watch_paths());
diff --git a/cli/tools/serve.rs b/cli/tools/serve.rs
index 4ce1cad6f2..e3f9e94f8e 100644
--- a/cli/tools/serve.rs
+++ b/cli/tools/serve.rs
@@ -44,12 +44,15 @@ pub async fn serve(
   maybe_npm_install(&factory).await?;
 
   let worker_factory = factory.create_cli_main_worker_factory().await?;
-
+  let hmr = serve_flags
+    .watch
+    .map(|watch_flags| watch_flags.hmr)
+    .unwrap_or(false);
   do_serve(
     worker_factory,
     main_module.clone(),
     serve_flags.worker_count,
-    false,
+    hmr,
   )
   .await
 }
@@ -109,8 +112,6 @@ async fn do_serve(
     }
   }
   Ok(exit_code)
-
-  // main.await?
 }
 
 async fn run_worker(
@@ -119,7 +120,7 @@ async fn run_worker(
   main_module: ModuleSpecifier,
   hmr: bool,
 ) -> Result<i32, AnyError> {
-  let mut worker = worker_factory
+  let mut worker: crate::worker::CliMainWorker = worker_factory
     .create_main_worker(
       deno_runtime::WorkerExecutionMode::Serve {
         is_main: false,
diff --git a/cli/tools/task.rs b/cli/tools/task.rs
index ae91f53a7a..502b09d2c2 100644
--- a/cli/tools/task.rs
+++ b/cli/tools/task.rs
@@ -16,7 +16,7 @@ use deno_core::anyhow::anyhow;
 use deno_core::anyhow::bail;
 use deno_core::anyhow::Context;
 use deno_core::error::AnyError;
-use deno_core::normalize_path;
+use deno_path_util::normalize_path;
 use deno_task_shell::ShellCommand;
 
 use crate::args::CliOptions;
@@ -182,19 +182,21 @@ async fn run_task(opts: RunTaskOptions<'_>) -> Result<i32, AnyError> {
     &task_runner::get_script_with_args(script, cli_options.argv()),
   );
 
-  task_runner::run_task(task_runner::RunTaskOptions {
-    task_name,
-    script,
-    cwd,
-    env_vars,
-    custom_commands,
-    init_cwd: opts.cli_options.initial_cwd(),
-    argv: cli_options.argv(),
-    root_node_modules_dir: npm_resolver
-      .root_node_modules_path()
-      .map(|p| p.as_path()),
-  })
-  .await
+  Ok(
+    task_runner::run_task(task_runner::RunTaskOptions {
+      task_name,
+      script,
+      cwd,
+      env_vars,
+      custom_commands,
+      init_cwd: opts.cli_options.initial_cwd(),
+      argv: cli_options.argv(),
+      root_node_modules_dir: npm_resolver.root_node_modules_path(),
+      stdio: None,
+    })
+    .await?
+    .exit_code,
+  )
 }
 
 fn output_task(task_name: &str, script: &str) {
diff --git a/cli/tools/test/mod.rs b/cli/tools/test/mod.rs
index e81abad0b2..966b0d285a 100644
--- a/cli/tools/test/mod.rs
+++ b/cli/tools/test/mod.rs
@@ -631,7 +631,7 @@ async fn configure_main_worker(
       "Deno[Deno.internal].core.setLeakTracingEnabled(true);",
     )?;
   }
-  let res = worker.execute_side_module_possibly_with_npm().await;
+  let res = worker.execute_side_module().await;
   let mut worker = worker.into_main_worker();
   match res {
     Ok(()) => Ok(()),
@@ -1357,6 +1357,7 @@ pub async fn report_tests(
         if let Err(err) = reporter.flush_report(&elapsed, &tests, &test_steps) {
           eprint!("Test reporter failed to flush: {}", err)
         }
+        #[allow(clippy::disallowed_methods)]
         std::process::exit(130);
       }
     }
@@ -1642,6 +1643,7 @@ pub async fn run_tests_with_watch(
     loop {
       signal::ctrl_c().await.unwrap();
       if !HAS_TEST_RUN_SIGINT_HANDLER.load(Ordering::Relaxed) {
+        #[allow(clippy::disallowed_methods)]
         std::process::exit(130);
       }
     }
diff --git a/cli/tools/upgrade.rs b/cli/tools/upgrade.rs
index 7f21e6649c..cb85859f7a 100644
--- a/cli/tools/upgrade.rs
+++ b/cli/tools/upgrade.rs
@@ -540,7 +540,7 @@ pub async fn upgrade(
   let Some(archive_data) = download_package(&client, download_url).await?
   else {
     log::error!("Download could not be found, aborting");
-    std::process::exit(1)
+    deno_runtime::exit(1)
   };
 
   log::info!(
@@ -579,6 +579,10 @@ pub async fn upgrade(
 
   let output_exe_path =
     full_path_output_flag.as_ref().unwrap_or(&current_exe_path);
+
+  #[cfg(windows)]
+  kill_running_deno_lsp_processes();
+
   let output_result = if *output_exe_path == current_exe_path {
     replace_exe(&new_exe_path, output_exe_path)
   } else {
@@ -913,7 +917,7 @@ async fn download_package(
   // text above which will stay alive after the progress bars are complete
   let progress = progress_bar.update("");
   let maybe_bytes = client
-    .download_with_progress(download_url.clone(), None, &progress)
+    .download_with_progress_and_retries(download_url.clone(), None, &progress)
     .await
     .with_context(|| format!("Failed downloading {download_url}. The version you requested may not have been built for the current architecture."))?;
   Ok(maybe_bytes)
@@ -966,6 +970,34 @@ fn check_windows_access_denied_error(
   })
 }
 
+#[cfg(windows)]
+fn kill_running_deno_lsp_processes() {
+  // limit this to `deno lsp` invocations to avoid killing important programs someone might be running
+  let is_debug = log::log_enabled!(log::Level::Debug);
+  let get_pipe = || {
+    if is_debug {
+      std::process::Stdio::inherit()
+    } else {
+      std::process::Stdio::null()
+    }
+  };
+  let _ = Command::new("powershell.exe")
+    .args([
+      "-Command",
+      r#"Get-WmiObject Win32_Process | Where-Object {
+    $_.Name -eq 'deno.exe' -and
+    $_.CommandLine -match '^(?:\"[^\"]+\"|\S+)\s+lsp\b'
+} | ForEach-Object {
+  if ($_.Terminate()) {
+    Write-Host 'Terminated:' $_.ProcessId
+  }
+}"#,
+    ])
+    .stdout(get_pipe())
+    .stderr(get_pipe())
+    .output();
+}
+
 fn set_exe_permissions(
   current_exe_path: &Path,
   output_exe_path: &Path,
diff --git a/cli/tsc/99_main_compiler.js b/cli/tsc/99_main_compiler.js
index 719f2b9824..68d099253a 100644
--- a/cli/tsc/99_main_compiler.js
+++ b/cli/tsc/99_main_compiler.js
@@ -121,8 +121,8 @@ delete Object.prototype.__proto__;
   /** @type {Map<string, ts.SourceFile>} */
   const sourceFileCache = new Map();
 
-  /** @type {Map<string, string>} */
-  const sourceTextCache = new Map();
+  /** @type {Map<string, ts.IScriptSnapshot & { isCjs?: boolean; }>} */
+  const scriptSnapshotCache = new Map();
 
   /** @type {Map<string, number>} */
   const sourceRefCounts = new Map();
@@ -133,9 +133,6 @@ delete Object.prototype.__proto__;
   /** @type {Map<string, boolean>} */
   const isNodeSourceFileCache = new Map();
 
-  /** @type {Map<string, boolean>} */
-  const isCjsCache = new Map();
-
   // Maps asset specifiers to the first scope that the asset was loaded into.
   /** @type {Map<string, string | null>} */
   const assetScopes = new Map();
@@ -210,12 +207,13 @@ delete Object.prototype.__proto__;
       const mapKey = path + key;
       let sourceFile = documentRegistrySourceFileCache.get(mapKey);
       if (!sourceFile || sourceFile.version !== version) {
+        const isCjs = /** @type {any} */ (scriptSnapshot).isCjs;
         sourceFile = ts.createLanguageServiceSourceFile(
           fileName,
           scriptSnapshot,
           {
             ...getCreateSourceFileOptions(sourceFileOptions),
-            impliedNodeFormat: (isCjsCache.get(fileName) ?? false)
+            impliedNodeFormat: isCjs
               ? ts.ModuleKind.CommonJS
               : ts.ModuleKind.ESNext,
             // in the lsp we want to be able to show documentation
@@ -320,7 +318,7 @@ delete Object.prototype.__proto__;
         if (lastRequestMethod != "cleanupSemanticCache") {
           const mapKey = path + key;
           documentRegistrySourceFileCache.delete(mapKey);
-          sourceTextCache.delete(path);
+          scriptSnapshotCache.delete(path);
           ops.op_release(path);
         }
       } else {
@@ -516,7 +514,6 @@ delete Object.prototype.__proto__;
   /** @typedef {{
    *    ls: ts.LanguageService & { [k:string]: any },
    *    compilerOptions: ts.CompilerOptions,
-   *    forceEnabledVerbatimModuleSyntax: boolean,
    *  }} LanguageServiceEntry */
   /** @type {{ unscoped: LanguageServiceEntry, byScope: Map<string, LanguageServiceEntry> }} */
   const languageServiceEntries = {
@@ -625,8 +622,6 @@ delete Object.prototype.__proto__;
         `"data" is unexpectedly null for "${specifier}".`,
       );
 
-      isCjsCache.set(specifier, isCjs);
-
       sourceFile = ts.createSourceFile(
         specifier,
         data,
@@ -700,7 +695,7 @@ delete Object.prototype.__proto__;
           /** @type {[string, ts.Extension] | undefined} */
           const resolved = ops.op_resolve(
             containingFilePath,
-            isCjsCache.get(containingFilePath) ?? false,
+            containingFileMode === ts.ModuleKind.CommonJS,
             [fileReference.fileName],
           )?.[0];
           if (resolved) {
@@ -724,7 +719,14 @@ delete Object.prototype.__proto__;
         }
       });
     },
-    resolveModuleNames(specifiers, base) {
+    resolveModuleNames(
+      specifiers,
+      base,
+      _reusedNames,
+      _redirectedReference,
+      _options,
+      containingSourceFile,
+    ) {
       if (logDebug) {
         debug(`host.resolveModuleNames()`);
         debug(`  base: ${base}`);
@@ -733,7 +735,7 @@ delete Object.prototype.__proto__;
       /** @type {Array<[string, ts.Extension] | undefined>} */
       const resolved = ops.op_resolve(
         base,
-        isCjsCache.get(base) ?? false,
+        containingSourceFile?.impliedNodeFormat === ts.ModuleKind.CommonJS,
         specifiers,
       );
       if (resolved) {
@@ -802,27 +804,32 @@ delete Object.prototype.__proto__;
       if (logDebug) {
         debug(`host.getScriptSnapshot("${specifier}")`);
       }
-      const sourceFile = sourceFileCache.get(specifier);
-      if (sourceFile) {
-        if (!assetScopes.has(specifier)) {
-          assetScopes.set(specifier, lastRequestScope);
+      if (specifier.startsWith(ASSETS_URL_PREFIX)) {
+        const sourceFile = this.getSourceFile(
+          specifier,
+          ts.ScriptTarget.ESNext,
+        );
+        if (sourceFile) {
+          if (!assetScopes.has(specifier)) {
+            assetScopes.set(specifier, lastRequestScope);
+          }
+          // This case only occurs for assets.
+          return ts.ScriptSnapshot.fromString(sourceFile.text);
         }
-        // This case only occurs for assets.
-        return ts.ScriptSnapshot.fromString(sourceFile.text);
       }
-      let sourceText = sourceTextCache.get(specifier);
-      if (sourceText == undefined) {
+      let scriptSnapshot = scriptSnapshotCache.get(specifier);
+      if (scriptSnapshot == undefined) {
         /** @type {{ data: string, version: string, isCjs: boolean }} */
         const fileInfo = ops.op_load(specifier);
         if (!fileInfo) {
           return undefined;
         }
-        isCjsCache.set(specifier, fileInfo.isCjs);
-        sourceTextCache.set(specifier, fileInfo.data);
+        scriptSnapshot = ts.ScriptSnapshot.fromString(fileInfo.data);
+        scriptSnapshot.isCjs = fileInfo.isCjs;
+        scriptSnapshotCache.set(specifier, scriptSnapshot);
         scriptVersionCache.set(specifier, fileInfo.version);
-        sourceText = fileInfo.data;
       }
-      return ts.ScriptSnapshot.fromString(sourceText);
+      return scriptSnapshot;
     },
   };
 
@@ -846,6 +853,8 @@ delete Object.prototype.__proto__;
         jqueryMessage,
       "Cannot_find_name_0_Do_you_need_to_install_type_definitions_for_jQuery_Try_npm_i_save_dev_types_Slash_2592":
         jqueryMessage,
+      "Module_0_was_resolved_to_1_but_allowArbitraryExtensions_is_not_set_6263":
+        "Module '{0}' was resolved to '{1}', but importing these modules is not supported.",
     };
   })());
 
@@ -1026,7 +1035,7 @@ delete Object.prototype.__proto__;
         : ts.sortAndDeduplicateDiagnostics(
           checkFiles.map((s) => program.getSemanticDiagnostics(s)).flat(),
         )),
-    ].filter(filterMapDiagnostic.bind(null, false));
+    ].filter(filterMapDiagnostic);
 
     // emit the tsbuildinfo file
     // @ts-ignore: emitBuildInfo is not exposed (https://github.com/microsoft/TypeScript/issues/49871)
@@ -1041,28 +1050,11 @@ delete Object.prototype.__proto__;
     debug("<<< exec stop");
   }
 
-  /**
-   * @param {boolean} isLsp
-   * @param {ts.Diagnostic} diagnostic
-   */
-  function filterMapDiagnostic(isLsp, diagnostic) {
+  /** @param {ts.Diagnostic} diagnostic */
+  function filterMapDiagnostic(diagnostic) {
     if (IGNORED_DIAGNOSTICS.includes(diagnostic.code)) {
       return false;
     }
-    if (isLsp) {
-      // TS1484: `...` is a type and must be imported using a type-only import when 'verbatimModuleSyntax' is enabled.
-      // We force-enable `verbatimModuleSyntax` in the LSP so the `type`
-      // modifier is used when auto-importing types. But we don't want this
-      // diagnostic unless it was explicitly enabled by the user.
-      if (diagnostic.code == 1484) {
-        const entry = (lastRequestScope
-          ? languageServiceEntries.byScope.get(lastRequestScope)
-          : null) ?? languageServiceEntries.unscoped;
-        if (entry.forceEnabledVerbatimModuleSyntax) {
-          return false;
-        }
-      }
-    }
     // make the diagnostic for using an `export =` in an es module a warning
     if (diagnostic.code === 1203) {
       diagnostic.category = ts.DiagnosticCategory.Warning;
@@ -1159,12 +1151,10 @@ delete Object.prototype.__proto__;
         "strict": true,
         "target": "esnext",
         "useDefineForClassFields": true,
-        "verbatimModuleSyntax": true,
         "jsx": "react",
         "jsxFactory": "React.createElement",
         "jsxFragmentFactory": "React.Fragment",
       }),
-      forceEnabledVerbatimModuleSyntax: true,
     };
     setLogDebug(enableDebugLogging, "TSLS");
     debug("serverInit()");
@@ -1230,17 +1220,8 @@ delete Object.prototype.__proto__;
           const ls = oldEntry
             ? oldEntry.ls
             : ts.createLanguageService(host, documentRegistry);
-          let forceEnabledVerbatimModuleSyntax = false;
-          if (!config["verbatimModuleSyntax"]) {
-            config["verbatimModuleSyntax"] = true;
-            forceEnabledVerbatimModuleSyntax = true;
-          }
           const compilerOptions = lspTsConfigToCompilerOptions(config);
-          newByScope.set(scope, {
-            ls,
-            compilerOptions,
-            forceEnabledVerbatimModuleSyntax,
-          });
+          newByScope.set(scope, { ls, compilerOptions });
           languageServiceEntries.byScope.delete(scope);
         }
         for (const oldEntry of languageServiceEntries.byScope.values()) {
@@ -1260,7 +1241,7 @@ delete Object.prototype.__proto__;
           closed = true;
         }
         scriptVersionCache.delete(script);
-        sourceTextCache.delete(script);
+        scriptSnapshotCache.delete(script);
       }
 
       if (newConfigsByScope || opened || closed) {
@@ -1305,7 +1286,7 @@ delete Object.prototype.__proto__;
               ...ls.getSemanticDiagnostics(specifier),
               ...ls.getSuggestionDiagnostics(specifier),
               ...ls.getSyntacticDiagnostics(specifier),
-            ].filter(filterMapDiagnostic.bind(null, true)));
+            ].filter(filterMapDiagnostic));
           }
           return respond(id, diagnosticMap);
         } catch (e) {
@@ -1366,18 +1347,12 @@ delete Object.prototype.__proto__;
     "console",
     "Console",
     "ErrorConstructor",
-    "exports",
     "gc",
     "Global",
     "ImportMeta",
     "localStorage",
-    "module",
-    "NodeModule",
-    "NodeRequire",
-    "process",
     "queueMicrotask",
     "RequestInit",
-    "require",
     "ResponseInit",
     "sessionStorage",
     "setImmediate",
diff --git a/cli/tsc/diagnostics.rs b/cli/tsc/diagnostics.rs
index b0394ec177..d3795706eb 100644
--- a/cli/tsc/diagnostics.rs
+++ b/cli/tsc/diagnostics.rs
@@ -323,7 +323,7 @@ impl Diagnostics {
             // todo(dsherret): use a short lived cache to prevent parsing
             // source maps so often
             if let Ok(source_map) =
-              SourceMap::from_slice(&fast_check_module.source_map)
+              SourceMap::from_slice(fast_check_module.source_map.as_bytes())
             {
               if let Some(start) = d.start.as_mut() {
                 let maybe_token = source_map
diff --git a/cli/tsc/dts/lib.deno.ns.d.ts b/cli/tsc/dts/lib.deno.ns.d.ts
index 36592e10dc..8179e4223c 100644
--- a/cli/tsc/dts/lib.deno.ns.d.ts
+++ b/cli/tsc/dts/lib.deno.ns.d.ts
@@ -556,14 +556,23 @@ declare namespace Deno {
      */
     env?: "inherit" | boolean | string[];
 
-    /** Specifies if the `sys` permission should be requested or revoked.
-     * If set to `"inherit"`, the current `sys` permission will be inherited.
-     * If set to `true`, the global `sys` permission will be requested.
-     * If set to `false`, the global `sys` permission will be revoked.
+    /** Specifies if the `ffi` permission should be requested or revoked.
+     * If set to `"inherit"`, the current `ffi` permission will be inherited.
+     * If set to `true`, the global `ffi` permission will be requested.
+     * If set to `false`, the global `ffi` permission will be revoked.
      *
      * @default {false}
      */
-    sys?: "inherit" | boolean | string[];
+    ffi?: "inherit" | boolean | Array<string | URL>;
+
+    /** Specifies if the `import` permission should be requested or revoked.
+     * If set to `"inherit"` the current `import` permission will be inherited.
+     * If set to `true`, the global `import` permission will be requested.
+     * If set to `false`, the global `import` permission will be revoked.
+     * If set to `Array<string>`, the `import` permissions will be requested with the
+     * specified domains.
+     */
+    import?: "inherit" | boolean | Array<string>;
 
     /** Specifies if the `net` permission should be requested or revoked.
      * if set to `"inherit"`, the current `net` permission will be inherited.
@@ -638,15 +647,6 @@ declare namespace Deno {
      */
     net?: "inherit" | boolean | string[];
 
-    /** Specifies if the `ffi` permission should be requested or revoked.
-     * If set to `"inherit"`, the current `ffi` permission will be inherited.
-     * If set to `true`, the global `ffi` permission will be requested.
-     * If set to `false`, the global `ffi` permission will be revoked.
-     *
-     * @default {false}
-     */
-    ffi?: "inherit" | boolean | Array<string | URL>;
-
     /** Specifies if the `read` permission should be requested or revoked.
      * If set to `"inherit"`, the current `read` permission will be inherited.
      * If set to `true`, the global `read` permission will be requested.
@@ -667,6 +667,15 @@ declare namespace Deno {
      */
     run?: "inherit" | boolean | Array<string | URL>;
 
+    /** Specifies if the `sys` permission should be requested or revoked.
+     * If set to `"inherit"`, the current `sys` permission will be inherited.
+     * If set to `true`, the global `sys` permission will be requested.
+     * If set to `false`, the global `sys` permission will be revoked.
+     *
+     * @default {false}
+     */
+    sys?: "inherit" | boolean | string[];
+
     /** Specifies if the `write` permission should be requested or revoked.
      * If set to `"inherit"`, the current `write` permission will be inherited.
      * If set to `true`, the global `write` permission will be requested.
@@ -2962,6 +2971,10 @@ declare namespace Deno {
      * field from `stat` on Mac/BSD and `ftCreationTime` on Windows. This may
      * not be available on all platforms. */
     birthtime: Date | null;
+    /** The last change time of the file. This corresponds to the `ctime`
+     * field from `stat` on Mac/BSD and `ChangeTime` on Windows. This may
+     * not be available on all platforms. */
+    ctime: Date | null;
     /** ID of the device containing the file. */
     dev: number;
     /** Inode number.
@@ -2970,8 +2983,7 @@ declare namespace Deno {
     ino: number | null;
     /** The underlying raw `st_mode` bits that contain the standard Unix
      * permissions for this file/directory.
-     *
-     * _Linux/Mac OS only._ */
+     */
     mode: number | null;
     /** Number of hard links pointing to this file.
      *
diff --git a/cli/tsc/dts/lib.deno.unstable.d.ts b/cli/tsc/dts/lib.deno.unstable.d.ts
index 973a09d92a..6234268c39 100644
--- a/cli/tsc/dts/lib.deno.unstable.d.ts
+++ b/cli/tsc/dts/lib.deno.unstable.d.ts
@@ -1225,6 +1225,108 @@ declare namespace Deno {
     export {}; // only export exports
   }
 
+  /**
+   * @category Telemetry
+   * @experimental
+   */
+  export namespace tracing {
+    /**
+     * Whether tracing is enabled.
+     * @category Telemetry
+     * @experimental
+     */
+    export const enabled: boolean;
+
+    /**
+     * Allowed attribute type.
+     * @category Telemetry
+     * @experimental
+     */
+    export type AttributeValue = string | number | boolean | bigint;
+
+    /**
+     * A tracing span.
+     * @category Telemetry
+     * @experimental
+     */
+    export class Span implements Disposable {
+      readonly traceId: string;
+      readonly spanId: string;
+      readonly parentSpanId: string;
+      readonly kind: string;
+      readonly name: string;
+      readonly startTime: number;
+      readonly endTime: number;
+      readonly status: null | { code: 1 } | { code: 2; message: string };
+      readonly attributes: Record<string, AttributeValue>;
+      readonly traceFlags: number;
+
+      /**
+       * Construct a new Span and enter it as the "current" span.
+       */
+      constructor(
+        name: string,
+        kind?: "internal" | "server" | "client" | "producer" | "consumer",
+      );
+
+      /**
+       * Set an attribute on this span.
+       */
+      setAttribute(
+        name: string,
+        value: AttributeValue,
+      ): void;
+
+      /**
+       * Enter this span as the "current" span.
+       */
+      enter(): void;
+
+      /**
+       * Exit this span as the "current" span and restore the previous one.
+       */
+      exit(): void;
+
+      /**
+       * End this span, and exit it as the "current" span.
+       */
+      end(): void;
+
+      [Symbol.dispose](): void;
+
+      /**
+       * Get the "current" span, if one exists.
+       */
+      static current(): Span | undefined | null;
+    }
+
+    /**
+     * A SpanExporter compatible with OpenTelemetry.js
+     * https://open-telemetry.github.io/opentelemetry-js/interfaces/_opentelemetry_sdk_trace_base.SpanExporter.html
+     * @category Telemetry
+     * @experimental
+     */
+    export class SpanExporter {}
+
+    /**
+     * A ContextManager compatible with OpenTelemetry.js
+     * https://open-telemetry.github.io/opentelemetry-js/interfaces/_opentelemetry_api.ContextManager.html
+     * @category Telemetry
+     * @experimental
+     */
+    export class ContextManager {}
+
+    export {}; // only export exports
+  }
+
+  /**
+   * @category Telemetry
+   * @experimental
+   */
+  export namespace metrics {
+    export {}; // only export exports
+  }
+
   export {}; // only export exports
 }
 
diff --git a/cli/tsc/mod.rs b/cli/tsc/mod.rs
index 0e3387494a..8f8bed20a4 100644
--- a/cli/tsc/mod.rs
+++ b/cli/tsc/mod.rs
@@ -3,10 +3,13 @@
 use crate::args::TsConfig;
 use crate::args::TypeCheckMode;
 use crate::cache::FastInsecureHasher;
+use crate::cache::ModuleInfoCache;
 use crate::node;
 use crate::npm::CliNpmResolver;
+use crate::resolver::CjsTracker;
 use crate::util::checksum;
 use crate::util::path::mapped_specifier_for_tsc;
+use crate::worker::create_isolate_create_params;
 
 use deno_ast::MediaType;
 use deno_core::anyhow::anyhow;
@@ -31,12 +34,14 @@ use deno_graph::GraphKind;
 use deno_graph::Module;
 use deno_graph::ModuleGraph;
 use deno_graph::ResolutionResolved;
+use deno_resolver::npm::ResolvePkgFolderFromDenoReqError;
+use deno_runtime::deno_fs;
 use deno_runtime::deno_node::NodeResolver;
 use deno_semver::npm::NpmPackageReqReference;
 use node_resolver::errors::NodeJsErrorCode;
 use node_resolver::errors::NodeJsErrorCoded;
+use node_resolver::errors::PackageSubpathResolveError;
 use node_resolver::NodeModuleKind;
-use node_resolver::NodeResolution;
 use node_resolver::NodeResolutionMode;
 use once_cell::sync::Lazy;
 use std::borrow::Cow;
@@ -45,6 +50,7 @@ use std::fmt;
 use std::path::Path;
 use std::path::PathBuf;
 use std::sync::Arc;
+use thiserror::Error;
 
 mod diagnostics;
 
@@ -299,8 +305,81 @@ pub struct EmittedFile {
   pub media_type: MediaType,
 }
 
+pub fn into_specifier_and_media_type(
+  specifier: Option<ModuleSpecifier>,
+) -> (ModuleSpecifier, MediaType) {
+  match specifier {
+    Some(specifier) => {
+      let media_type = MediaType::from_specifier(&specifier);
+
+      (specifier, media_type)
+    }
+    None => (
+      Url::parse("internal:///missing_dependency.d.ts").unwrap(),
+      MediaType::Dts,
+    ),
+  }
+}
+
+#[derive(Debug)]
+pub struct TypeCheckingCjsTracker {
+  cjs_tracker: Arc<CjsTracker>,
+  module_info_cache: Arc<ModuleInfoCache>,
+}
+
+impl TypeCheckingCjsTracker {
+  pub fn new(
+    cjs_tracker: Arc<CjsTracker>,
+    module_info_cache: Arc<ModuleInfoCache>,
+  ) -> Self {
+    Self {
+      cjs_tracker,
+      module_info_cache,
+    }
+  }
+
+  pub fn is_cjs(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+    code: &Arc<str>,
+  ) -> bool {
+    let maybe_is_script = self
+      .module_info_cache
+      .as_module_analyzer()
+      .analyze_sync(specifier, media_type, code)
+      .ok()
+      .map(|info| info.is_script);
+    maybe_is_script
+      .and_then(|is_script| {
+        self
+          .cjs_tracker
+          .is_cjs_with_known_is_script(specifier, media_type, is_script)
+          .ok()
+      })
+      .unwrap_or_else(|| {
+        self
+          .cjs_tracker
+          .is_maybe_cjs(specifier, media_type)
+          .unwrap_or(false)
+      })
+  }
+
+  pub fn is_cjs_with_known_is_script(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+    is_script: bool,
+  ) -> Result<bool, node_resolver::errors::ClosestPkgJsonError> {
+    self
+      .cjs_tracker
+      .is_cjs_with_known_is_script(specifier, media_type, is_script)
+  }
+}
+
 #[derive(Debug)]
 pub struct RequestNpmState {
+  pub cjs_tracker: Arc<TypeCheckingCjsTracker>,
   pub node_resolver: Arc<NodeResolver>,
   pub npm_resolver: Arc<dyn CliNpmResolver>,
 }
@@ -453,7 +532,7 @@ pub fn as_ts_script_kind(media_type: MediaType) -> i32 {
     MediaType::Tsx => 4,
     MediaType::Json => 6,
     MediaType::SourceMap
-    | MediaType::TsBuildInfo
+    | MediaType::Css
     | MediaType::Wasm
     | MediaType::Unknown => 0,
   }
@@ -486,25 +565,22 @@ fn op_load_inner(
 ) -> Result<Option<LoadResponse>, AnyError> {
   fn load_from_node_modules(
     specifier: &ModuleSpecifier,
-    node_resolver: Option<&NodeResolver>,
+    npm_state: Option<&RequestNpmState>,
     media_type: &mut MediaType,
     is_cjs: &mut bool,
   ) -> Result<String, AnyError> {
     *media_type = MediaType::from_specifier(specifier);
-    *is_cjs = node_resolver
-      .map(|node_resolver| {
-        match node_resolver.url_to_node_resolution(specifier.clone()) {
-          Ok(NodeResolution::CommonJs(_)) => true,
-          Ok(NodeResolution::Esm(_))
-          | Ok(NodeResolution::BuiltIn(_))
-          | Err(_) => false,
-        }
-      })
-      .unwrap_or(false);
     let file_path = specifier.to_file_path().unwrap();
     let code = std::fs::read_to_string(&file_path)
       .with_context(|| format!("Unable to load {}", file_path.display()))?;
-    Ok(code)
+    let code: Arc<str> = code.into();
+    *is_cjs = npm_state
+      .map(|npm_state| {
+        npm_state.cjs_tracker.is_cjs(specifier, *media_type, &code)
+      })
+      .unwrap_or(false);
+    // todo(dsherret): how to avoid cloning here?
+    Ok(code.to_string())
   }
 
   let state = state.borrow_mut::<State>();
@@ -557,6 +633,13 @@ fn op_load_inner(
       match module {
         Module::Js(module) => {
           media_type = module.media_type;
+          if let Some(npm_state) = &state.maybe_npm {
+            is_cjs = npm_state.cjs_tracker.is_cjs_with_known_is_script(
+              specifier,
+              module.media_type,
+              module.is_script,
+            )?;
+          }
           let source = module
             .fast_check_module()
             .map(|m| &*m.source)
@@ -570,11 +653,13 @@ fn op_load_inner(
         Module::Npm(_) | Module::Node(_) => None,
         Module::External(module) => {
           // means it's Deno code importing an npm module
-          let specifier =
-            node::resolve_specifier_into_node_modules(&module.specifier);
+          let specifier = node::resolve_specifier_into_node_modules(
+            &module.specifier,
+            &deno_fs::RealFs,
+          );
           Some(Cow::Owned(load_from_node_modules(
             &specifier,
-            state.maybe_npm.as_ref().map(|n| n.node_resolver.as_ref()),
+            state.maybe_npm.as_ref(),
             &mut media_type,
             &mut is_cjs,
           )?))
@@ -587,7 +672,7 @@ fn op_load_inner(
     {
       Some(Cow::Owned(load_from_node_modules(
         specifier,
-        Some(npm.node_resolver.as_ref()),
+        Some(npm),
         &mut media_type,
         &mut is_cjs,
       )?))
@@ -662,6 +747,7 @@ fn op_resolve_inner(
       "Error converting a string module specifier for \"op_resolve\".",
     )?
   };
+  let referrer_module = state.graph.get(&referrer);
   for specifier in args.specifiers {
     if specifier.starts_with("node:") {
       resolved.push((
@@ -677,23 +763,44 @@ fn op_resolve_inner(
       continue;
     }
 
-    let graph = &state.graph;
-    let resolved_dep = graph
-      .get(&referrer)
+    let resolved_dep = referrer_module
       .and_then(|m| m.js())
       .and_then(|m| m.dependencies_prefer_fast_check().get(&specifier))
       .and_then(|d| d.maybe_type.ok().or_else(|| d.maybe_code.ok()));
 
     let maybe_result = match resolved_dep {
       Some(ResolutionResolved { specifier, .. }) => {
-        resolve_graph_specifier_types(specifier, &referrer, state)?
+        resolve_graph_specifier_types(
+          specifier,
+          &referrer,
+          referrer_kind,
+          state,
+        )?
+      }
+      _ => {
+        match resolve_non_graph_specifier_types(
+          &specifier,
+          &referrer,
+          referrer_kind,
+          state,
+        ) {
+          Ok(maybe_result) => maybe_result,
+          Err(
+            err @ ResolveNonGraphSpecifierTypesError::ResolvePkgFolderFromDenoReq(
+              ResolvePkgFolderFromDenoReqError::Managed(_),
+            ),
+          ) => {
+            // it's most likely requesting the jsxImportSource, which isn't loaded
+            // into the graph when not using jsx, so just ignore this error
+            if specifier.ends_with("/jsx-runtime") {
+              None
+            } else {
+              return Err(err.into());
+            }
+          }
+          Err(err) => return Err(err.into()),
+        }
       }
-      _ => resolve_non_graph_specifier_types(
-        &specifier,
-        &referrer,
-        referrer_kind,
-        state,
-      )?,
     };
     let result = match maybe_result {
       Some((specifier, media_type)) => {
@@ -718,7 +825,13 @@ fn op_resolve_inner(
             }
           }
         };
-        (specifier_str, media_type.as_ts_extension())
+        (
+          specifier_str,
+          match media_type {
+            MediaType::Css => ".js", // surface these as .js for typescript
+            media_type => media_type.as_ts_extension(),
+          },
+        )
       }
       None => (
         MISSING_DEPENDENCY_SPECIFIER.to_string(),
@@ -735,6 +848,7 @@ fn op_resolve_inner(
 fn resolve_graph_specifier_types(
   specifier: &ModuleSpecifier,
   referrer: &ModuleSpecifier,
+  referrer_kind: NodeModuleKind,
   state: &State,
 ) -> Result<Option<(ModuleSpecifier, MediaType)>, AnyError> {
   let graph = &state.graph;
@@ -787,43 +901,53 @@ fn resolve_graph_specifier_types(
             &package_folder,
             module.nv_reference.sub_path(),
             Some(referrer),
+            referrer_kind,
             NodeResolutionMode::Types,
           );
-        let maybe_resolution = match res_result {
-          Ok(res) => Some(res),
+        let maybe_url = match res_result {
+          Ok(url) => Some(url),
           Err(err) => match err.code() {
             NodeJsErrorCode::ERR_TYPES_NOT_FOUND
             | NodeJsErrorCode::ERR_MODULE_NOT_FOUND => None,
             _ => return Err(err.into()),
           },
         };
-        Ok(Some(NodeResolution::into_specifier_and_media_type(
-          maybe_resolution,
-        )))
+        Ok(Some(into_specifier_and_media_type(maybe_url)))
       } else {
         Ok(None)
       }
     }
     Some(Module::External(module)) => {
       // we currently only use "External" for when the module is in an npm package
-      Ok(state.maybe_npm.as_ref().map(|npm| {
-        let specifier =
-          node::resolve_specifier_into_node_modules(&module.specifier);
-        NodeResolution::into_specifier_and_media_type(
-          npm.node_resolver.url_to_node_resolution(specifier).ok(),
-        )
+      Ok(state.maybe_npm.as_ref().map(|_| {
+        let specifier = node::resolve_specifier_into_node_modules(
+          &module.specifier,
+          &deno_fs::RealFs,
+        );
+        into_specifier_and_media_type(Some(specifier))
       }))
     }
     Some(Module::Node(_)) | None => Ok(None),
   }
 }
 
+#[derive(Debug, Error)]
+enum ResolveNonGraphSpecifierTypesError {
+  #[error(transparent)]
+  ResolvePkgFolderFromDenoReq(#[from] ResolvePkgFolderFromDenoReqError),
+  #[error(transparent)]
+  PackageSubpathResolve(#[from] PackageSubpathResolveError),
+}
+
 fn resolve_non_graph_specifier_types(
   raw_specifier: &str,
   referrer: &ModuleSpecifier,
   referrer_kind: NodeModuleKind,
   state: &State,
-) -> Result<Option<(ModuleSpecifier, MediaType)>, AnyError> {
+) -> Result<
+  Option<(ModuleSpecifier, MediaType)>,
+  ResolveNonGraphSpecifierTypesError,
+> {
   let npm = match state.maybe_npm.as_ref() {
     Some(npm) => npm,
     None => return Ok(None), // we only support non-graph types for npm packages
@@ -831,7 +955,7 @@ fn resolve_non_graph_specifier_types(
   let node_resolver = &npm.node_resolver;
   if node_resolver.in_npm_package(referrer) {
     // we're in an npm package, so use node resolution
-    Ok(Some(NodeResolution::into_specifier_and_media_type(
+    Ok(Some(into_specifier_and_media_type(
       node_resolver
         .resolve(
           raw_specifier,
@@ -839,7 +963,8 @@ fn resolve_non_graph_specifier_types(
           referrer_kind,
           NodeResolutionMode::Types,
         )
-        .ok(),
+        .ok()
+        .map(|res| res.into_url()),
     )))
   } else if let Ok(npm_req_ref) =
     NpmPackageReqReference::from_str(raw_specifier)
@@ -856,19 +981,18 @@ fn resolve_non_graph_specifier_types(
       &package_folder,
       npm_req_ref.sub_path(),
       Some(referrer),
+      referrer_kind,
       NodeResolutionMode::Types,
     );
-    let maybe_resolution = match res_result {
-      Ok(res) => Some(res),
+    let maybe_url = match res_result {
+      Ok(url) => Some(url),
       Err(err) => match err.code() {
         NodeJsErrorCode::ERR_TYPES_NOT_FOUND
         | NodeJsErrorCode::ERR_MODULE_NOT_FOUND => None,
         _ => return Err(err.into()),
       },
     };
-    Ok(Some(NodeResolution::into_specifier_and_media_type(
-      maybe_resolution,
-    )))
+    Ok(Some(into_specifier_and_media_type(maybe_url)))
   } else {
     Ok(None)
   }
@@ -981,6 +1105,7 @@ pub fn exec(request: Request) -> Result<Response, AnyError> {
       root_map,
       remapped_specifiers,
     )],
+    create_params: create_isolate_create_params(),
     ..Default::default()
   });
 
diff --git a/cli/util/extract.rs b/cli/util/extract.rs
index 841cf6eb0f..be68202aa1 100644
--- a/cli/util/extract.rs
+++ b/cli/util/extract.rs
@@ -64,7 +64,7 @@ fn extract_inner(
   }) {
     Ok(parsed) => {
       let mut c = ExportCollector::default();
-      c.visit_program(parsed.program_ref());
+      c.visit_program(parsed.program().as_ref());
       c
     }
     Err(_) => ExportCollector::default(),
@@ -254,7 +254,11 @@ impl ExportCollector {
     let mut import_specifiers = vec![];
 
     if let Some(default_export) = &self.default_export {
-      if !symbols_to_exclude.contains(default_export) {
+      // If the default export conflicts with a named export, a named one
+      // takes precedence.
+      if !symbols_to_exclude.contains(default_export)
+        && !self.named_exports.contains(default_export)
+      {
         import_specifiers.push(ast::ImportSpecifier::Default(
           ast::ImportDefaultSpecifier {
             span: DUMMY_SP,
@@ -566,14 +570,14 @@ fn generate_pseudo_file(
   })?;
 
   let top_level_atoms = swc_utils::collect_decls_with_ctxt::<Atom, _>(
-    parsed.program_ref(),
+    &parsed.program_ref(),
     parsed.top_level_context(),
   );
 
   let transformed =
     parsed
       .program_ref()
-      .clone()
+      .to_owned()
       .fold_with(&mut as_folder(Transform {
         specifier: &file.specifier,
         base_file_specifier,
@@ -582,7 +586,10 @@ fn generate_pseudo_file(
         wrap_kind,
       }));
 
-  let source = deno_ast::swc::codegen::to_code(&transformed);
+  let source = deno_ast::swc::codegen::to_code_with_comments(
+    Some(&parsed.comments().as_single_threaded()),
+    &transformed,
+  );
 
   log::debug!("{}:\n{}", file.specifier, source);
 
@@ -1137,6 +1144,57 @@ Deno.test("file:///README.md$6-12.js", async ()=>{
           media_type: MediaType::JavaScript,
         }],
       },
+      // https://github.com/denoland/deno/issues/26009
+      Test {
+        input: Input {
+          source: r#"
+/**
+ * ```ts
+ * console.log(Foo)
+ * ```
+ */
+export class Foo {}
+export default Foo
+"#,
+          specifier: "file:///main.ts",
+        },
+        expected: vec![Expected {
+          source: r#"import { Foo } from "file:///main.ts";
+Deno.test("file:///main.ts$3-6.ts", async ()=>{
+    console.log(Foo);
+});
+"#,
+          specifier: "file:///main.ts$3-6.ts",
+          media_type: MediaType::TypeScript,
+        }],
+      },
+      // https://github.com/denoland/deno/issues/26728
+      Test {
+        input: Input {
+          source: r#"
+/**
+ * ```ts
+ * // @ts-expect-error: can only add numbers
+ * add('1', '2');
+ * ```
+ */
+export function add(first: number, second: number) {
+  return first + second;
+}
+"#,
+          specifier: "file:///main.ts",
+        },
+        expected: vec![Expected {
+          source: r#"import { add } from "file:///main.ts";
+Deno.test("file:///main.ts$3-7.ts", async ()=>{
+    // @ts-expect-error: can only add numbers
+    add('1', '2');
+});
+"#,
+          specifier: "file:///main.ts$3-7.ts",
+          media_type: MediaType::TypeScript,
+        }],
+      },
     ];
 
     for test in tests {
@@ -1326,6 +1384,53 @@ assertEquals(add(1, 2), 3);
           media_type: MediaType::JavaScript,
         }],
       },
+      // https://github.com/denoland/deno/issues/26009
+      Test {
+        input: Input {
+          source: r#"
+/**
+ * ```ts
+ * console.log(Foo)
+ * ```
+ */
+export class Foo {}
+export default Foo
+"#,
+          specifier: "file:///main.ts",
+        },
+        expected: vec![Expected {
+          source: r#"import { Foo } from "file:///main.ts";
+console.log(Foo);
+"#,
+          specifier: "file:///main.ts$3-6.ts",
+          media_type: MediaType::TypeScript,
+        }],
+      },
+      // https://github.com/denoland/deno/issues/26728
+      Test {
+        input: Input {
+          source: r#"
+/**
+ * ```ts
+ * // @ts-expect-error: can only add numbers
+ * add('1', '2');
+ * ```
+ */
+export function add(first: number, second: number) {
+  return first + second;
+}
+"#,
+          specifier: "file:///main.ts",
+        },
+        expected: vec![Expected {
+          source: r#"import { add } from "file:///main.ts";
+// @ts-expect-error: can only add numbers
+add('1', '2');
+"#,
+          specifier: "file:///main.ts$3-7.ts",
+          media_type: MediaType::TypeScript,
+        }],
+      },
     ];
 
     for test in tests {
@@ -1366,7 +1471,7 @@ assertEquals(add(1, 2), 3);
       })
       .unwrap();
 
-      collector.visit_program(parsed.program_ref());
+      parsed.program_ref().visit_with(&mut collector);
       collector
     }
 
@@ -1581,6 +1686,16 @@ declare global {
         named_expected: atom_set!(),
         default_expected: None,
       },
+      // The identifier `Foo` conflicts, but `ExportCollector` doesn't do
+      // anything about it. It is handled by `to_import_specifiers` method.
+      Test {
+        input: r#"
+export class Foo {}
+export default Foo
+"#,
+        named_expected: atom_set!("Foo"),
+        default_expected: Some("Foo".into()),
+      },
     ];
 
     for test in tests {
diff --git a/cli/util/file_watcher.rs b/cli/util/file_watcher.rs
index d92d880bc1..21ea95e067 100644
--- a/cli/util/file_watcher.rs
+++ b/cli/util/file_watcher.rs
@@ -30,7 +30,7 @@ use tokio::sync::mpsc;
 use tokio::sync::mpsc::UnboundedReceiver;
 use tokio::time::sleep;
 
-const CLEAR_SCREEN: &str = "\x1B[2J\x1B[1;1H";
+const CLEAR_SCREEN: &str = "\x1B[H\x1B[2J\x1B[3J";
 const DEBOUNCE_INTERVAL: Duration = Duration::from_millis(200);
 
 struct DebouncedReceiver {
@@ -73,7 +73,6 @@ impl DebouncedReceiver {
   }
 }
 
-#[allow(clippy::print_stderr)]
 async fn error_handler<F>(watch_future: F) -> bool
 where
   F: Future<Output = Result<(), AnyError>>,
@@ -84,7 +83,7 @@ where
       Some(e) => format_js_error(e),
       None => format!("{err:?}"),
     };
-    eprintln!(
+    log::error!(
       "{}: {}",
       colors::red_bold("error"),
       error_string.trim_start_matches("error: ")
diff --git a/cli/util/fs.rs b/cli/util/fs.rs
index fdf6035ecd..d36c02242c 100644
--- a/cli/util/fs.rs
+++ b/cli/util/fs.rs
@@ -20,7 +20,6 @@ use deno_core::error::AnyError;
 use deno_core::unsync::spawn_blocking;
 use deno_core::ModuleSpecifier;
 use deno_runtime::deno_fs::FileSystem;
-use deno_runtime::deno_node::PathClean;
 
 use crate::util::path::get_atomic_file_path;
 use crate::util::progress_bar::ProgressBar;
@@ -37,10 +36,98 @@ pub fn atomic_write_file_with_retries<T: AsRef<[u8]>>(
   file_path: &Path,
   data: T,
   mode: u32,
+) -> std::io::Result<()> {
+  struct RealAtomicWriteFileFs {
+    mode: u32,
+  }
+
+  impl AtomicWriteFileFs for RealAtomicWriteFileFs {
+    fn write_file(&self, path: &Path, bytes: &[u8]) -> std::io::Result<()> {
+      write_file(path, bytes, self.mode)
+    }
+    fn rename_file(&self, from: &Path, to: &Path) -> std::io::Result<()> {
+      std::fs::rename(from, to)
+    }
+    fn remove_file(&self, path: &Path) -> std::io::Result<()> {
+      std::fs::remove_file(path)
+    }
+    fn create_dir_all(&self, dir_path: &Path) -> std::io::Result<()> {
+      std::fs::create_dir_all(dir_path)
+    }
+    fn path_exists(&self, path: &Path) -> bool {
+      path.exists()
+    }
+  }
+
+  atomic_write_file_with_retries_and_fs(
+    &RealAtomicWriteFileFs { mode },
+    file_path,
+    data.as_ref(),
+  )
+}
+
+pub trait AtomicWriteFileFs {
+  fn write_file(&self, path: &Path, bytes: &[u8]) -> std::io::Result<()>;
+  fn rename_file(&self, from: &Path, to: &Path) -> std::io::Result<()>;
+  fn remove_file(&self, path: &Path) -> std::io::Result<()>;
+  fn create_dir_all(&self, dir_path: &Path) -> std::io::Result<()>;
+  fn path_exists(&self, path: &Path) -> bool;
+}
+
+pub struct AtomicWriteFileFsAdapter<'a> {
+  pub fs: &'a dyn FileSystem,
+  pub write_mode: u32,
+}
+
+impl<'a> AtomicWriteFileFs for AtomicWriteFileFsAdapter<'a> {
+  fn write_file(&self, path: &Path, bytes: &[u8]) -> std::io::Result<()> {
+    self
+      .fs
+      .write_file_sync(
+        path,
+        deno_runtime::deno_fs::OpenOptions::write(
+          true,
+          false,
+          false,
+          Some(self.write_mode),
+        ),
+        None,
+        bytes,
+      )
+      .map_err(|e| e.into_io_error())
+  }
+
+  fn rename_file(&self, from: &Path, to: &Path) -> std::io::Result<()> {
+    self.fs.rename_sync(from, to).map_err(|e| e.into_io_error())
+  }
+
+  fn remove_file(&self, path: &Path) -> std::io::Result<()> {
+    self
+      .fs
+      .remove_sync(path, false)
+      .map_err(|e| e.into_io_error())
+  }
+
+  fn create_dir_all(&self, dir_path: &Path) -> std::io::Result<()> {
+    self
+      .fs
+      .mkdir_sync(dir_path, /* recursive */ true, None)
+      .map_err(|e| e.into_io_error())
+  }
+
+  fn path_exists(&self, path: &Path) -> bool {
+    self.fs.exists_sync(path)
+  }
+}
+
+pub fn atomic_write_file_with_retries_and_fs<T: AsRef<[u8]>>(
+  fs: &impl AtomicWriteFileFs,
+  file_path: &Path,
+  data: T,
 ) -> std::io::Result<()> {
   let mut count = 0;
   loop {
-    match atomic_write_file(file_path, data.as_ref(), mode) {
+    match atomic_write_file(fs, file_path, data.as_ref()) {
       Ok(()) => return Ok(()),
       Err(err) => {
         if count >= 5 {
@@ -61,63 +148,54 @@ pub fn atomic_write_file_with_retries<T: AsRef<[u8]>>(
 ///
 /// This also handles creating the directory if a NotFound error
 /// occurs.
-fn atomic_write_file<T: AsRef<[u8]>>(
+fn atomic_write_file(
+  fs: &impl AtomicWriteFileFs,
   file_path: &Path,
-  data: T,
-  mode: u32,
+  data: &[u8],
 ) -> std::io::Result<()> {
   fn atomic_write_file_raw(
+    fs: &impl AtomicWriteFileFs,
     temp_file_path: &Path,
     file_path: &Path,
     data: &[u8],
-    mode: u32,
   ) -> std::io::Result<()> {
-    write_file(temp_file_path, data, mode)?;
-    std::fs::rename(temp_file_path, file_path).map_err(|err| {
-      // clean up the created temp file on error
-      let _ = std::fs::remove_file(temp_file_path);
-      err
-    })
+    fs.write_file(temp_file_path, data)?;
+    fs.rename_file(temp_file_path, file_path)
+      .inspect_err(|_err| {
+        // clean up the created temp file on error
+        let _ = fs.remove_file(temp_file_path);
+      })
   }
 
-  fn inner(file_path: &Path, data: &[u8], mode: u32) -> std::io::Result<()> {
-    let temp_file_path = get_atomic_file_path(file_path);
+  let temp_file_path = get_atomic_file_path(file_path);
 
-    if let Err(write_err) =
-      atomic_write_file_raw(&temp_file_path, file_path, data, mode)
-    {
-      if write_err.kind() == ErrorKind::NotFound {
-        let parent_dir_path = file_path.parent().unwrap();
-        match std::fs::create_dir_all(parent_dir_path) {
-          Ok(()) => {
-            return atomic_write_file_raw(
-              &temp_file_path,
-              file_path,
-              data,
-              mode,
-            )
+  if let Err(write_err) =
+    atomic_write_file_raw(fs, &temp_file_path, file_path, data)
+  {
+    if write_err.kind() == ErrorKind::NotFound {
+      let parent_dir_path = file_path.parent().unwrap();
+      match fs.create_dir_all(parent_dir_path) {
+        Ok(()) => {
+          return atomic_write_file_raw(fs, &temp_file_path, file_path, data)
             .map_err(|err| add_file_context_to_err(file_path, err));
-          }
-          Err(create_err) => {
-            if !parent_dir_path.exists() {
-              return Err(Error::new(
-                create_err.kind(),
-                format!(
-                  "{:#} (for '{}')\nCheck the permission of the directory.",
-                  create_err,
-                  parent_dir_path.display()
-                ),
-              ));
-            }
+        }
+        Err(create_err) => {
+          if !fs.path_exists(parent_dir_path) {
+            return Err(Error::new(
+              create_err.kind(),
+              format!(
+                "{:#} (for '{}')\nCheck the permission of the directory.",
+                create_err,
+                parent_dir_path.display()
+              ),
+            ));
           }
         }
       }
-      return Err(add_file_context_to_err(file_path, write_err));
     }
-    Ok(())
+    return Err(add_file_context_to_err(file_path, write_err));
   }
-
-  inner(file_path, data.as_ref(), mode)
+  Ok(())
 }
 
 /// Creates a std::fs::File handling if the parent does not exist.
@@ -199,7 +277,7 @@ pub fn write_file_2<T: AsRef<[u8]>>(
 
 /// Similar to `std::fs::canonicalize()` but strips UNC prefixes on Windows.
 pub fn canonicalize_path(path: &Path) -> Result<PathBuf, Error> {
-  Ok(deno_core::strip_unc_prefix(path.canonicalize()?))
+  Ok(deno_path_util::strip_unc_prefix(path.canonicalize()?))
 }
 
 /// Canonicalizes a path which might be non-existent by going up the
@@ -211,48 +289,18 @@ pub fn canonicalize_path(path: &Path) -> Result<PathBuf, Error> {
 pub fn canonicalize_path_maybe_not_exists(
   path: &Path,
 ) -> Result<PathBuf, Error> {
-  canonicalize_path_maybe_not_exists_with_custom_fn(path, canonicalize_path)
+  deno_path_util::canonicalize_path_maybe_not_exists(path, &canonicalize_path)
 }
 
 pub fn canonicalize_path_maybe_not_exists_with_fs(
   path: &Path,
   fs: &dyn FileSystem,
 ) -> Result<PathBuf, Error> {
-  canonicalize_path_maybe_not_exists_with_custom_fn(path, |path| {
+  deno_path_util::canonicalize_path_maybe_not_exists(path, &|path| {
     fs.realpath_sync(path).map_err(|err| err.into_io_error())
   })
 }
 
-fn canonicalize_path_maybe_not_exists_with_custom_fn(
-  path: &Path,
-  canonicalize: impl Fn(&Path) -> Result<PathBuf, Error>,
-) -> Result<PathBuf, Error> {
-  let path = path.to_path_buf().clean();
-  let mut path = path.as_path();
-  let mut names_stack = Vec::new();
-  loop {
-    match canonicalize(path) {
-      Ok(mut canonicalized_path) => {
-        for name in names_stack.into_iter().rev() {
-          canonicalized_path = canonicalized_path.join(name);
-        }
-        return Ok(canonicalized_path);
-      }
-      Err(err) if err.kind() == ErrorKind::NotFound => {
-        names_stack.push(match path.file_name() {
-          Some(name) => name.to_owned(),
-          None => return Err(err),
-        });
-        path = match path.parent() {
-          Some(parent) => parent,
-          None => return Err(err),
-        };
-      }
-      Err(err) => return Err(err),
-    }
-  }
-}
-
 /// Collects module specifiers that satisfy the given predicate as a file path, by recursively walking `include`.
 /// Specifiers that start with http and https are left intact.
 /// Note: This ignores all .git and node_modules folders.
@@ -517,7 +565,9 @@ pub fn symlink_dir(oldpath: &Path, newpath: &Path) -> Result<(), Error> {
     use std::os::windows::fs::symlink_dir;
     symlink_dir(oldpath, newpath).map_err(|err| {
       if let Some(code) = err.raw_os_error() {
-        if code as u32 == winapi::shared::winerror::ERROR_PRIVILEGE_NOT_HELD {
+        if code as u32 == winapi::shared::winerror::ERROR_PRIVILEGE_NOT_HELD
+          || code as u32 == winapi::shared::winerror::ERROR_INVALID_FUNCTION
+        {
           return err_mapper(err, Some(ErrorKind::PermissionDenied));
         }
       }
@@ -708,8 +758,8 @@ pub fn specifier_from_file_path(
 mod tests {
   use super::*;
   use deno_core::futures;
-  use deno_core::normalize_path;
   use deno_core::parking_lot::Mutex;
+  use deno_path_util::normalize_path;
   use pretty_assertions::assert_eq;
   use test_util::PathRef;
   use test_util::TempDir;
diff --git a/cli/util/logger.rs b/cli/util/logger.rs
index cdc89411fe..f76663df2c 100644
--- a/cli/util/logger.rs
+++ b/cli/util/logger.rs
@@ -29,6 +29,7 @@ impl log::Log for CliLogger {
       // thread's state
       DrawThread::hide();
       self.0.log(record);
+      deno_runtime::ops::otel::handle_log(record);
       DrawThread::show();
     }
   }
@@ -65,6 +66,8 @@ pub fn init(maybe_level: Option<log::Level>) {
   .filter_module("swc_ecma_parser", log::LevelFilter::Error)
   // Suppress span lifecycle logs since they are too verbose
   .filter_module("tracing::span", log::LevelFilter::Off)
+  // for deno_compile, this is too verbose
+  .filter_module("editpe", log::LevelFilter::Error)
   .format(|buf, record| {
     let mut target = record.target().to_string();
     if let Some(line_no) = record.line() {
diff --git a/cli/util/mod.rs b/cli/util/mod.rs
index e59b09d2c7..f81a74c449 100644
--- a/cli/util/mod.rs
+++ b/cli/util/mod.rs
@@ -14,6 +14,7 @@ pub mod logger;
 pub mod path;
 pub mod progress_bar;
 pub mod result;
+pub mod retry;
 pub mod sync;
 pub mod text_encoding;
 pub mod unix;
diff --git a/cli/util/path.rs b/cli/util/path.rs
index 6f09cf1eac..58bed664f9 100644
--- a/cli/util/path.rs
+++ b/cli/util/path.rs
@@ -42,21 +42,6 @@ pub fn get_extension(file_path: &Path) -> Option<String> {
     .map(|e| e.to_lowercase());
 }
 
-pub fn specifier_has_extension(
-  specifier: &ModuleSpecifier,
-  searching_ext: &str,
-) -> bool {
-  let Some((_, ext)) = specifier.path().rsplit_once('.') else {
-    return false;
-  };
-  let searching_ext = searching_ext.strip_prefix('.').unwrap_or(searching_ext);
-  debug_assert!(!searching_ext.contains('.')); // exts like .d.ts are not implemented here
-  if ext.len() != searching_ext.len() {
-    return false;
-  }
-  ext.eq_ignore_ascii_case(searching_ext)
-}
-
 pub fn get_atomic_dir_path(file_path: &Path) -> PathBuf {
   let rand = gen_rand_path_component();
   let new_file_name = format!(
@@ -165,48 +150,6 @@ pub fn relative_path(from: &Path, to: &Path) -> Option<PathBuf> {
   pathdiff::diff_paths(to, from)
 }
 
-/// Gets if the provided character is not supported on all
-/// kinds of file systems.
-pub fn is_banned_path_char(c: char) -> bool {
-  matches!(c, '<' | '>' | ':' | '"' | '|' | '?' | '*')
-}
-
-/// Gets a safe local directory name for the provided url.
-///
-/// For example:
-/// https://deno.land:8080/path -> deno.land_8080/path
-pub fn root_url_to_safe_local_dirname(root: &ModuleSpecifier) -> PathBuf {
-  fn sanitize_segment(text: &str) -> String {
-    text
-      .chars()
-      .map(|c| if is_banned_segment_char(c) { '_' } else { c })
-      .collect()
-  }
-
-  fn is_banned_segment_char(c: char) -> bool {
-    matches!(c, '/' | '\\') || is_banned_path_char(c)
-  }
-
-  let mut result = String::new();
-  if let Some(domain) = root.domain() {
-    result.push_str(&sanitize_segment(domain));
-  }
-  if let Some(port) = root.port() {
-    if !result.is_empty() {
-      result.push('_');
-    }
-    result.push_str(&port.to_string());
-  }
-  let mut result = PathBuf::from(result);
-  if let Some(segments) = root.path_segments() {
-    for segment in segments.filter(|s| !s.is_empty()) {
-      result = result.join(sanitize_segment(segment));
-    }
-  }
-
-  result
-}
-
 /// Slightly different behaviour than the default matching
 /// where an exact path needs to be matched to be opted-in
 /// rather than just a partial directory match.
@@ -392,18 +335,6 @@ mod test {
     }
   }
 
-  #[test]
-  fn test_specifier_has_extension() {
-    fn get(specifier: &str, ext: &str) -> bool {
-      specifier_has_extension(&ModuleSpecifier::parse(specifier).unwrap(), ext)
-    }
-
-    assert!(get("file:///a/b/c.ts", "ts"));
-    assert!(get("file:///a/b/c.ts", ".ts"));
-    assert!(!get("file:///a/b/c.ts", ".cts"));
-    assert!(get("file:///a/b/c.CtS", ".cts"));
-  }
-
   #[test]
   fn test_to_percent_decoded_str() {
     let str = to_percent_decoded_str("%F0%9F%A6%95");
diff --git a/cli/util/progress_bar/renderer.rs b/cli/util/progress_bar/renderer.rs
index a83ceb3334..6b08dada12 100644
--- a/cli/util/progress_bar/renderer.rs
+++ b/cli/util/progress_bar/renderer.rs
@@ -193,10 +193,16 @@ impl ProgressBarRenderer for TextOnlyProgressBarRenderer {
         }
       };
 
+      // TODO(@marvinhagemeister): We're trying to reconstruct the original
+      // specifier from the resolved one, but we lack the information about
+      // private registries URLs and other things here.
       let message = display_entry
         .message
         .replace("https://registry.npmjs.org/", "npm:")
-        .replace("https://jsr.io/", "jsr:");
+        .replace("https://jsr.io/", "jsr:")
+        .replace("%2f", "/")
+        .replace("%2F", "/");
+
       display_str.push_str(
         &colors::gray(format!(" - {}{}\n", message, bytes_text)).to_string(),
       );
diff --git a/cli/util/retry.rs b/cli/util/retry.rs
new file mode 100644
index 0000000000..a8febe60de
--- /dev/null
+++ b/cli/util/retry.rs
@@ -0,0 +1,41 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+use std::future::Future;
+use std::time::Duration;
+
+pub fn retry<
+  F: FnMut() -> Fut,
+  T,
+  E,
+  Fut: Future<Output = Result<T, E>>,
+  ShouldRetry: FnMut(&E) -> bool,
+>(
+  mut f: F,
+  mut should_retry: ShouldRetry,
+) -> impl Future<Output = Result<T, E>> {
+  const WAITS: [Duration; 3] = [
+    Duration::from_millis(100),
+    Duration::from_millis(250),
+    Duration::from_millis(500),
+  ];
+
+  let mut waits = WAITS.into_iter();
+  async move {
+    let mut first_result = None;
+    loop {
+      let result = f().await;
+      match result {
+        Ok(r) => return Ok(r),
+        Err(e) if !should_retry(&e) => return Err(e),
+        _ => {}
+      }
+      if first_result.is_none() {
+        first_result = Some(result);
+      }
+      let Some(wait) = waits.next() else {
+        return first_result.unwrap();
+      };
+      tokio::time::sleep(wait).await;
+    }
+  }
+}
diff --git a/cli/util/text_encoding.rs b/cli/util/text_encoding.rs
index d2e0832c95..8524e63ebb 100644
--- a/cli/util/text_encoding.rs
+++ b/cli/util/text_encoding.rs
@@ -1,6 +1,8 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
+use std::borrow::Cow;
 use std::ops::Range;
+use std::sync::Arc;
 
 use base64::prelude::BASE64_STANDARD;
 use base64::Engine;
@@ -9,6 +11,15 @@ use deno_core::ModuleSourceCode;
 static SOURCE_MAP_PREFIX: &[u8] =
   b"//# sourceMappingURL=data:application/json;base64,";
 
+pub fn from_utf8_lossy_owned(bytes: Vec<u8>) -> String {
+  match String::from_utf8_lossy(&bytes) {
+    Cow::Owned(code) => code,
+    // SAFETY: `String::from_utf8_lossy` guarantees that the result is valid
+    // UTF-8 if `Cow::Borrowed` is returned.
+    Cow::Borrowed(_) => unsafe { String::from_utf8_unchecked(bytes) },
+  }
+}
+
 pub fn source_map_from_code(code: &[u8]) -> Option<Vec<u8>> {
   let range = find_source_map_range(code)?;
   let source_map_range = &code[range];
@@ -85,6 +96,29 @@ fn find_source_map_range(code: &[u8]) -> Option<Range<usize>> {
   }
 }
 
+/// Converts an `Arc<str>` to an `Arc<[u8]>`.
+#[allow(dead_code)]
+pub fn arc_str_to_bytes(arc_str: Arc<str>) -> Arc<[u8]> {
+  let raw = Arc::into_raw(arc_str);
+  // SAFETY: This is safe because they have the same memory layout.
+  unsafe { Arc::from_raw(raw as *const [u8]) }
+}
+
+/// Converts an `Arc<u8>` to an `Arc<str>` if able.
+#[allow(dead_code)]
+pub fn arc_u8_to_arc_str(
+  arc_u8: Arc<[u8]>,
+) -> Result<Arc<str>, std::str::Utf8Error> {
+  // Check that the string is valid UTF-8.
+  std::str::from_utf8(&arc_u8)?;
+  // SAFETY: the string is valid UTF-8, and the layout Arc<[u8]> is the same as
+  // Arc<str>. This is proven by the From<Arc<str>> impl for Arc<[u8]> from the
+  // standard library.
+  Ok(unsafe {
+    std::mem::transmute::<std::sync::Arc<[u8]>, std::sync::Arc<str>>(arc_u8)
+  })
+}
+
 #[cfg(test)]
 mod tests {
   use std::sync::Arc;
diff --git a/cli/util/v8.rs b/cli/util/v8.rs
index fb16e67b77..6e690e6f30 100644
--- a/cli/util/v8.rs
+++ b/cli/util/v8.rs
@@ -46,15 +46,14 @@ pub fn init_v8_flags(
     .skip(1)
     .collect::<Vec<_>>();
 
-  #[allow(clippy::print_stderr)]
   if !unrecognized_v8_flags.is_empty() {
     for f in unrecognized_v8_flags {
-      eprintln!("error: V8 did not recognize flag '{f}'");
+      log::error!("error: V8 did not recognize flag '{f}'");
     }
-    eprintln!("\nFor a list of V8 flags, use '--v8-flags=--help'");
-    std::process::exit(1);
+    log::error!("\nFor a list of V8 flags, use '--v8-flags=--help'");
+    deno_runtime::exit(1);
   }
   if v8_flags_includes_help {
-    std::process::exit(0);
+    deno_runtime::exit(0);
   }
 }
diff --git a/cli/worker.rs b/cli/worker.rs
index c355d18bd5..c6cbf77f1b 100644
--- a/cli/worker.rs
+++ b/cli/worker.rs
@@ -14,34 +14,37 @@ use deno_core::v8;
 use deno_core::CompiledWasmModuleStore;
 use deno_core::Extension;
 use deno_core::FeatureChecker;
-use deno_core::ModuleId;
 use deno_core::ModuleLoader;
 use deno_core::PollEventLoopOptions;
 use deno_core::SharedArrayBufferStore;
 use deno_runtime::code_cache;
 use deno_runtime::deno_broadcast_channel::InMemoryBroadcastChannel;
 use deno_runtime::deno_fs;
-use deno_runtime::deno_node;
 use deno_runtime::deno_node::NodeExtInitServices;
+use deno_runtime::deno_node::NodeRequireLoader;
+use deno_runtime::deno_node::NodeRequireLoaderRc;
 use deno_runtime::deno_node::NodeResolver;
+use deno_runtime::deno_node::PackageJsonResolver;
 use deno_runtime::deno_permissions::PermissionsContainer;
 use deno_runtime::deno_tls::RootCertStoreProvider;
 use deno_runtime::deno_web::BlobStore;
 use deno_runtime::fmt_errors::format_js_error;
 use deno_runtime::inspector_server::InspectorServer;
+use deno_runtime::ops::otel::OtelConfig;
 use deno_runtime::ops::process::NpmProcessStateProviderRc;
 use deno_runtime::ops::worker_host::CreateWebWorkerCb;
-use deno_runtime::permissions::RuntimePermissionDescriptorParser;
 use deno_runtime::web_worker::WebWorker;
 use deno_runtime::web_worker::WebWorkerOptions;
+use deno_runtime::web_worker::WebWorkerServiceOptions;
 use deno_runtime::worker::MainWorker;
 use deno_runtime::worker::WorkerOptions;
+use deno_runtime::worker::WorkerServiceOptions;
 use deno_runtime::BootstrapOptions;
 use deno_runtime::WorkerExecutionMode;
 use deno_runtime::WorkerLogLevel;
 use deno_semver::npm::NpmPackageReqReference;
 use deno_terminal::colors;
-use node_resolver::NodeResolution;
+use node_resolver::NodeModuleKind;
 use node_resolver::NodeResolutionMode;
 use tokio::select;
 
@@ -55,21 +58,22 @@ use crate::util::file_watcher::WatcherCommunicator;
 use crate::util::file_watcher::WatcherRestartMode;
 use crate::version;
 
-pub struct ModuleLoaderAndSourceMapGetter {
+pub struct CreateModuleLoaderResult {
   pub module_loader: Rc<dyn ModuleLoader>,
+  pub node_require_loader: Rc<dyn NodeRequireLoader>,
 }
 
 pub trait ModuleLoaderFactory: Send + Sync {
   fn create_for_main(
     &self,
     root_permissions: PermissionsContainer,
-  ) -> ModuleLoaderAndSourceMapGetter;
+  ) -> CreateModuleLoaderResult;
 
   fn create_for_worker(
     &self,
     parent_permissions: PermissionsContainer,
     permissions: PermissionsContainer,
-  ) -> ModuleLoaderAndSourceMapGetter;
+  ) -> CreateModuleLoaderResult;
 }
 
 #[async_trait::async_trait(?Send)]
@@ -106,7 +110,6 @@ pub struct CliMainWorkerOptions {
   pub inspect_wait: bool,
   pub strace_ops: Option<Vec<String>>,
   pub is_inspecting: bool,
-  pub is_npm_main: bool,
   pub location: Option<Url>,
   pub argv0: Option<String>,
   pub node_debug: Option<String>,
@@ -134,21 +137,26 @@ struct SharedWorkerState {
   module_loader_factory: Box<dyn ModuleLoaderFactory>,
   node_resolver: Arc<NodeResolver>,
   npm_resolver: Arc<dyn CliNpmResolver>,
-  permission_desc_parser: Arc<RuntimePermissionDescriptorParser>,
+  pkg_json_resolver: Arc<PackageJsonResolver>,
   root_cert_store_provider: Arc<dyn RootCertStoreProvider>,
   root_permissions: PermissionsContainer,
   shared_array_buffer_store: SharedArrayBufferStore,
   storage_key_resolver: StorageKeyResolver,
   options: CliMainWorkerOptions,
   subcommand: DenoSubcommand,
+  otel_config: Option<OtelConfig>, // `None` means OpenTelemetry is disabled.
 }
 
 impl SharedWorkerState {
-  pub fn create_node_init_services(&self) -> NodeExtInitServices {
+  pub fn create_node_init_services(
+    &self,
+    node_require_loader: NodeRequireLoaderRc,
+  ) -> NodeExtInitServices {
     NodeExtInitServices {
-      node_require_resolver: self.npm_resolver.clone().into_require_resolver(),
+      node_require_loader,
       node_resolver: self.node_resolver.clone(),
-      npm_resolver: self.npm_resolver.clone().into_npm_resolver(),
+      npm_resolver: self.npm_resolver.clone().into_npm_pkg_folder_resolver(),
+      pkg_json_resolver: self.pkg_json_resolver.clone(),
     }
   }
 
@@ -159,7 +167,6 @@ impl SharedWorkerState {
 
 pub struct CliMainWorker {
   main_module: ModuleSpecifier,
-  is_main_cjs: bool,
   worker: MainWorker,
   shared: Arc<SharedWorkerState>,
 }
@@ -181,17 +188,7 @@ impl CliMainWorker {
 
     log::debug!("main_module {}", self.main_module);
 
-    if self.is_main_cjs {
-      deno_node::load_cjs_module(
-        &mut self.worker.js_runtime,
-        &self.main_module.to_file_path().unwrap().to_string_lossy(),
-        true,
-        self.shared.options.inspect_brk,
-      )?;
-    } else {
-      self.execute_main_module_possibly_with_npm().await?;
-    }
-
+    self.execute_main_module().await?;
     self.worker.dispatch_load_event()?;
 
     loop {
@@ -279,22 +276,7 @@ impl CliMainWorker {
       /// Execute the given main module emitting load and unload events before and after execution
       /// respectively.
       pub async fn execute(&mut self) -> Result<(), AnyError> {
-        if self.inner.is_main_cjs {
-          deno_node::load_cjs_module(
-            &mut self.inner.worker.js_runtime,
-            &self
-              .inner
-              .main_module
-              .to_file_path()
-              .unwrap()
-              .to_string_lossy(),
-            true,
-            self.inner.shared.options.inspect_brk,
-          )?;
-        } else {
-          self.inner.execute_main_module_possibly_with_npm().await?;
-        }
-
+        self.inner.execute_main_module().await?;
         self.inner.worker.dispatch_load_event()?;
         self.pending_unload = true;
 
@@ -335,24 +317,13 @@ impl CliMainWorker {
     executor.execute().await
   }
 
-  pub async fn execute_main_module_possibly_with_npm(
-    &mut self,
-  ) -> Result<(), AnyError> {
+  pub async fn execute_main_module(&mut self) -> Result<(), AnyError> {
     let id = self.worker.preload_main_module(&self.main_module).await?;
-    self.evaluate_module_possibly_with_npm(id).await
+    self.worker.evaluate_module(id).await
   }
 
-  pub async fn execute_side_module_possibly_with_npm(
-    &mut self,
-  ) -> Result<(), AnyError> {
+  pub async fn execute_side_module(&mut self) -> Result<(), AnyError> {
     let id = self.worker.preload_side_module(&self.main_module).await?;
-    self.evaluate_module_possibly_with_npm(id).await
-  }
-
-  async fn evaluate_module_possibly_with_npm(
-    &mut self,
-    id: ModuleId,
-  ) -> Result<(), AnyError> {
     self.worker.evaluate_module(id).await
   }
 
@@ -431,12 +402,13 @@ impl CliMainWorkerFactory {
     module_loader_factory: Box<dyn ModuleLoaderFactory>,
     node_resolver: Arc<NodeResolver>,
     npm_resolver: Arc<dyn CliNpmResolver>,
-    permission_parser: Arc<RuntimePermissionDescriptorParser>,
+    pkg_json_resolver: Arc<PackageJsonResolver>,
     root_cert_store_provider: Arc<dyn RootCertStoreProvider>,
     root_permissions: PermissionsContainer,
     storage_key_resolver: StorageKeyResolver,
     subcommand: DenoSubcommand,
     options: CliMainWorkerOptions,
+    otel_config: Option<OtelConfig>,
   ) -> Self {
     Self {
       shared: Arc::new(SharedWorkerState {
@@ -452,13 +424,14 @@ impl CliMainWorkerFactory {
         module_loader_factory,
         node_resolver,
         npm_resolver,
-        permission_desc_parser: permission_parser,
+        pkg_json_resolver,
         root_cert_store_provider,
         root_permissions,
         shared_array_buffer_store: Default::default(),
         storage_key_resolver,
         options,
         subcommand,
+        otel_config,
       }),
     }
   }
@@ -488,7 +461,13 @@ impl CliMainWorkerFactory {
     stdio: deno_runtime::deno_io::Stdio,
   ) -> Result<CliMainWorker, AnyError> {
     let shared = &self.shared;
-    let (main_module, is_main_cjs) = if let Ok(package_ref) =
+    let CreateModuleLoaderResult {
+      module_loader,
+      node_require_loader,
+    } = shared
+      .module_loader_factory
+      .create_for_main(permissions.clone());
+    let main_module = if let Ok(package_ref) =
       NpmPackageReqReference::from_specifier(&main_module)
     {
       if let Some(npm_resolver) = shared.npm_resolver.as_managed() {
@@ -508,9 +487,8 @@ impl CliMainWorkerFactory {
           package_ref.req(),
           &referrer,
         )?;
-      let node_resolution = self
+      let main_module = self
         .resolve_binary_entrypoint(&package_folder, package_ref.sub_path())?;
-      let is_main_cjs = matches!(node_resolution, NodeResolution::CommonJs(_));
 
       if let Some(lockfile) = &shared.maybe_lockfile {
         // For npm binary commands, ensure that the lockfile gets updated
@@ -519,22 +497,11 @@ impl CliMainWorkerFactory {
         lockfile.write_if_changed()?;
       }
 
-      (node_resolution.into_url(), is_main_cjs)
-    } else if shared.options.is_npm_main
-      || shared.node_resolver.in_npm_package(&main_module)
-    {
-      let node_resolution =
-        shared.node_resolver.url_to_node_resolution(main_module)?;
-      let is_main_cjs = matches!(node_resolution, NodeResolution::CommonJs(_));
-      (node_resolution.into_url(), is_main_cjs)
+      main_module
     } else {
-      let is_cjs = main_module.path().ends_with(".cjs");
-      (main_module, is_cjs)
+      main_module
     };
 
-    let ModuleLoaderAndSourceMapGetter { module_loader } = shared
-      .module_loader_factory
-      .create_for_main(permissions.clone());
     let maybe_inspector_server = shared.maybe_inspector_server.clone();
 
     let create_web_worker_cb =
@@ -570,6 +537,25 @@ impl CliMainWorkerFactory {
       }
     }
 
+    let services = WorkerServiceOptions {
+      root_cert_store_provider: Some(shared.root_cert_store_provider.clone()),
+      module_loader,
+      fs: shared.fs.clone(),
+      node_services: Some(
+        shared.create_node_init_services(node_require_loader),
+      ),
+      npm_process_state_provider: Some(shared.npm_process_state_provider()),
+      blob_store: shared.blob_store.clone(),
+      broadcast_channel: shared.broadcast_channel.clone(),
+      shared_array_buffer_store: Some(shared.shared_array_buffer_store.clone()),
+      compiled_wasm_module_store: Some(
+        shared.compiled_wasm_module_store.clone(),
+      ),
+      feature_checker,
+      permissions,
+      v8_code_cache: shared.code_cache.clone(),
+    };
+
     let options = WorkerOptions {
       bootstrap: BootstrapOptions {
         deno_version: crate::version::DENO_VERSION_INFO.deno.to_string(),
@@ -596,15 +582,15 @@ impl CliMainWorkerFactory {
         mode,
         serve_port: shared.options.serve_port,
         serve_host: shared.options.serve_host.clone(),
+        otel_config: shared.otel_config.clone(),
       },
       extensions: custom_extensions,
       startup_snapshot: crate::js::deno_isolate_init(),
-      create_params: None,
+      create_params: create_isolate_create_params(),
       unsafely_ignore_certificate_errors: shared
         .options
         .unsafely_ignore_certificate_errors
         .clone(),
-      root_cert_store_provider: Some(shared.root_cert_store_provider.clone()),
       seed: shared.options.seed,
       format_js_error_fn: Some(Arc::new(format_js_error)),
       create_web_worker_cb,
@@ -612,29 +598,16 @@ impl CliMainWorkerFactory {
       should_break_on_first_statement: shared.options.inspect_brk,
       should_wait_for_inspector_session: shared.options.inspect_wait,
       strace_ops: shared.options.strace_ops.clone(),
-      module_loader,
-      fs: shared.fs.clone(),
-      node_services: Some(shared.create_node_init_services()),
-      npm_process_state_provider: Some(shared.npm_process_state_provider()),
       get_error_class_fn: Some(&errors::get_error_class_name),
       cache_storage_dir,
       origin_storage_dir,
-      blob_store: shared.blob_store.clone(),
-      broadcast_channel: shared.broadcast_channel.clone(),
-      shared_array_buffer_store: Some(shared.shared_array_buffer_store.clone()),
-      compiled_wasm_module_store: Some(
-        shared.compiled_wasm_module_store.clone(),
-      ),
       stdio,
-      feature_checker,
-      permission_desc_parser: shared.permission_desc_parser.clone(),
       skip_op_registration: shared.options.skip_op_registration,
-      v8_code_cache: shared.code_cache.clone(),
     };
 
     let mut worker = MainWorker::bootstrap_from_options(
       main_module.clone(),
-      permissions,
+      services,
       options,
     );
 
@@ -657,7 +630,6 @@ impl CliMainWorkerFactory {
 
     Ok(CliMainWorker {
       main_module,
-      is_main_cjs,
       worker,
       shared: shared.clone(),
     })
@@ -667,19 +639,19 @@ impl CliMainWorkerFactory {
     &self,
     package_folder: &Path,
     sub_path: Option<&str>,
-  ) -> Result<NodeResolution, AnyError> {
+  ) -> Result<ModuleSpecifier, AnyError> {
     match self
       .shared
       .node_resolver
       .resolve_binary_export(package_folder, sub_path)
     {
-      Ok(node_resolution) => Ok(node_resolution),
+      Ok(specifier) => Ok(specifier),
       Err(original_err) => {
         // if the binary entrypoint was not found, fallback to regular node resolution
         let result =
           self.resolve_binary_entrypoint_fallback(package_folder, sub_path);
         match result {
-          Ok(Some(resolution)) => Ok(resolution),
+          Ok(Some(specifier)) => Ok(specifier),
           Ok(None) => Err(original_err.into()),
           Err(fallback_err) => {
             bail!("{:#}\n\nFallback failed: {:#}", original_err, fallback_err)
@@ -694,7 +666,7 @@ impl CliMainWorkerFactory {
     &self,
     package_folder: &Path,
     sub_path: Option<&str>,
-  ) -> Result<Option<NodeResolution>, AnyError> {
+  ) -> Result<Option<ModuleSpecifier>, AnyError> {
     // only fallback if the user specified a sub path
     if sub_path.is_none() {
       // it's confusing to users if the package doesn't have any binary
@@ -703,28 +675,24 @@ impl CliMainWorkerFactory {
       return Ok(None);
     }
 
-    let resolution = self
+    let specifier = self
       .shared
       .node_resolver
       .resolve_package_subpath_from_deno_module(
         package_folder,
         sub_path,
         /* referrer */ None,
+        NodeModuleKind::Esm,
         NodeResolutionMode::Execution,
       )?;
-    match &resolution {
-      NodeResolution::BuiltIn(_) => Ok(None),
-      NodeResolution::CommonJs(specifier) | NodeResolution::Esm(specifier) => {
-        if specifier
-          .to_file_path()
-          .map(|p| p.exists())
-          .unwrap_or(false)
-        {
-          Ok(Some(resolution))
-        } else {
-          bail!("Cannot find module '{}'", specifier)
-        }
-      }
+    if specifier
+      .to_file_path()
+      .map(|p| p.exists())
+      .unwrap_or(false)
+    {
+      Ok(Some(specifier))
+    } else {
+      bail!("Cannot find module '{}'", specifier)
     }
   }
 }
@@ -736,11 +704,13 @@ fn create_web_worker_callback(
   Arc::new(move |args| {
     let maybe_inspector_server = shared.maybe_inspector_server.clone();
 
-    let ModuleLoaderAndSourceMapGetter { module_loader } =
-      shared.module_loader_factory.create_for_worker(
-        args.parent_permissions.clone(),
-        args.permissions.clone(),
-      );
+    let CreateModuleLoaderResult {
+      module_loader,
+      node_require_loader,
+    } = shared.module_loader_factory.create_for_worker(
+      args.parent_permissions.clone(),
+      args.permissions.clone(),
+    );
     let create_web_worker_cb =
       create_web_worker_callback(shared.clone(), stdio.clone());
 
@@ -766,7 +736,28 @@ fn create_web_worker_callback(
       }
     }
 
+    let services = WebWorkerServiceOptions {
+      root_cert_store_provider: Some(shared.root_cert_store_provider.clone()),
+      module_loader,
+      fs: shared.fs.clone(),
+      node_services: Some(
+        shared.create_node_init_services(node_require_loader),
+      ),
+      blob_store: shared.blob_store.clone(),
+      broadcast_channel: shared.broadcast_channel.clone(),
+      shared_array_buffer_store: Some(shared.shared_array_buffer_store.clone()),
+      compiled_wasm_module_store: Some(
+        shared.compiled_wasm_module_store.clone(),
+      ),
+      maybe_inspector_server,
+      feature_checker,
+      npm_process_state_provider: Some(shared.npm_process_state_provider()),
+      permissions: args.permissions,
+    };
     let options = WebWorkerOptions {
+      name: args.name,
+      main_module: args.main_module.clone(),
+      worker_id: args.worker_id,
       bootstrap: BootstrapOptions {
         deno_version: crate::version::DENO_VERSION_INFO.deno.to_string(),
         args: shared.options.argv.clone(),
@@ -777,7 +768,7 @@ fn create_web_worker_callback(
         enable_op_summary_metrics: shared.options.enable_op_summary_metrics,
         enable_testing_features: shared.options.enable_testing_features,
         locale: deno_core::v8::icu::get_language_tag(),
-        location: Some(args.main_module.clone()),
+        location: Some(args.main_module),
         no_color: !colors::use_color(),
         color_level: colors::get_color_level(),
         is_stdout_tty: deno_terminal::is_stdout_tty(),
@@ -792,46 +783,39 @@ fn create_web_worker_callback(
         mode: WorkerExecutionMode::Worker,
         serve_port: shared.options.serve_port,
         serve_host: shared.options.serve_host.clone(),
+        otel_config: shared.otel_config.clone(),
       },
       extensions: vec![],
       startup_snapshot: crate::js::deno_isolate_init(),
+      create_params: create_isolate_create_params(),
       unsafely_ignore_certificate_errors: shared
         .options
         .unsafely_ignore_certificate_errors
         .clone(),
-      root_cert_store_provider: Some(shared.root_cert_store_provider.clone()),
       seed: shared.options.seed,
       create_web_worker_cb,
       format_js_error_fn: Some(Arc::new(format_js_error)),
-      module_loader,
-      fs: shared.fs.clone(),
-      node_services: Some(shared.create_node_init_services()),
       worker_type: args.worker_type,
-      maybe_inspector_server,
       get_error_class_fn: Some(&errors::get_error_class_name),
-      blob_store: shared.blob_store.clone(),
-      broadcast_channel: shared.broadcast_channel.clone(),
-      shared_array_buffer_store: Some(shared.shared_array_buffer_store.clone()),
-      compiled_wasm_module_store: Some(
-        shared.compiled_wasm_module_store.clone(),
-      ),
       stdio: stdio.clone(),
       cache_storage_dir,
-      feature_checker,
-      permission_desc_parser: shared.permission_desc_parser.clone(),
       strace_ops: shared.options.strace_ops.clone(),
       close_on_idle: args.close_on_idle,
       maybe_worker_metadata: args.maybe_worker_metadata,
-      npm_process_state_provider: Some(shared.npm_process_state_provider()),
     };
 
-    WebWorker::bootstrap_from_options(
-      args.name,
-      args.permissions,
-      args.main_module,
-      args.worker_id,
-      options,
-    )
+    WebWorker::bootstrap_from_options(services, options)
+  })
+}
+
+/// By default V8 uses 1.4Gb heap limit which is meant for browser tabs.
+/// Instead probe for the total memory on the system and use it instead
+/// as a default.
+pub fn create_isolate_create_params() -> Option<v8::CreateParams> {
+  let maybe_mem_info = deno_runtime::sys_info::mem_info();
+  maybe_mem_info.map(|mem_info| {
+    v8::CreateParams::default()
+      .heap_limits_from_system_memory(mem_info.total, 0)
   })
 }
 
@@ -841,23 +825,43 @@ fn create_web_worker_callback(
 mod tests {
   use super::*;
   use deno_core::resolve_path;
+  use deno_core::FsModuleLoader;
   use deno_fs::RealFs;
   use deno_runtime::deno_permissions::Permissions;
+  use deno_runtime::permissions::RuntimePermissionDescriptorParser;
 
   fn create_test_worker() -> MainWorker {
     let main_module =
       resolve_path("./hello.js", &std::env::current_dir().unwrap()).unwrap();
-    let permissions = PermissionsContainer::new(
-      Arc::new(RuntimePermissionDescriptorParser::new(Arc::new(RealFs))),
-      Permissions::none_without_prompt(),
-    );
-
+    let fs = Arc::new(RealFs);
+    let permission_desc_parser =
+      Arc::new(RuntimePermissionDescriptorParser::new(fs.clone()));
     let options = WorkerOptions {
       startup_snapshot: crate::js::deno_isolate_init(),
       ..Default::default()
     };
 
-    MainWorker::bootstrap_from_options(main_module, permissions, options)
+    MainWorker::bootstrap_from_options(
+      main_module,
+      WorkerServiceOptions {
+        module_loader: Rc::new(FsModuleLoader),
+        permissions: PermissionsContainer::new(
+          permission_desc_parser,
+          Permissions::none_without_prompt(),
+        ),
+        blob_store: Default::default(),
+        broadcast_channel: Default::default(),
+        feature_checker: Default::default(),
+        node_services: Default::default(),
+        npm_process_state_provider: Default::default(),
+        root_cert_store_provider: Default::default(),
+        shared_array_buffer_store: Default::default(),
+        compiled_wasm_module_store: Default::default(),
+        v8_code_cache: Default::default(),
+        fs,
+      },
+      options,
+    )
   }
 
   #[tokio::test]
diff --git a/ext/broadcast_channel/Cargo.toml b/ext/broadcast_channel/Cargo.toml
index 8b8c9a1883..90ac038357 100644
--- a/ext/broadcast_channel/Cargo.toml
+++ b/ext/broadcast_channel/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_broadcast_channel"
-version = "0.162.0"
+version = "0.171.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -16,5 +16,6 @@ path = "lib.rs"
 [dependencies]
 async-trait.workspace = true
 deno_core.workspace = true
+thiserror.workspace = true
 tokio.workspace = true
 uuid.workspace = true
diff --git a/ext/broadcast_channel/in_memory_broadcast_channel.rs b/ext/broadcast_channel/in_memory_broadcast_channel.rs
index 00b52a9d60..61dc68e17d 100644
--- a/ext/broadcast_channel/in_memory_broadcast_channel.rs
+++ b/ext/broadcast_channel/in_memory_broadcast_channel.rs
@@ -3,13 +3,13 @@
 use std::sync::Arc;
 
 use async_trait::async_trait;
-use deno_core::error::AnyError;
 use deno_core::parking_lot::Mutex;
 use tokio::sync::broadcast;
 use tokio::sync::mpsc;
 use uuid::Uuid;
 
 use crate::BroadcastChannel;
+use crate::BroadcastChannelError;
 
 #[derive(Clone)]
 pub struct InMemoryBroadcastChannel(Arc<Mutex<broadcast::Sender<Message>>>);
@@ -41,7 +41,7 @@ impl Default for InMemoryBroadcastChannel {
 impl BroadcastChannel for InMemoryBroadcastChannel {
   type Resource = InMemoryBroadcastChannelResource;
 
-  fn subscribe(&self) -> Result<Self::Resource, AnyError> {
+  fn subscribe(&self) -> Result<Self::Resource, BroadcastChannelError> {
     let (cancel_tx, cancel_rx) = mpsc::unbounded_channel();
     let broadcast_rx = self.0.lock().subscribe();
     let rx = tokio::sync::Mutex::new((broadcast_rx, cancel_rx));
@@ -53,7 +53,10 @@ impl BroadcastChannel for InMemoryBroadcastChannel {
     })
   }
 
-  fn unsubscribe(&self, resource: &Self::Resource) -> Result<(), AnyError> {
+  fn unsubscribe(
+    &self,
+    resource: &Self::Resource,
+  ) -> Result<(), BroadcastChannelError> {
     Ok(resource.cancel_tx.send(())?)
   }
 
@@ -62,7 +65,7 @@ impl BroadcastChannel for InMemoryBroadcastChannel {
     resource: &Self::Resource,
     name: String,
     data: Vec<u8>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), BroadcastChannelError> {
     let name = Arc::new(name);
     let data = Arc::new(data);
     let uuid = resource.uuid;
@@ -73,7 +76,7 @@ impl BroadcastChannel for InMemoryBroadcastChannel {
   async fn recv(
     &self,
     resource: &Self::Resource,
-  ) -> Result<Option<crate::Message>, AnyError> {
+  ) -> Result<Option<crate::Message>, BroadcastChannelError> {
     let mut g = resource.rx.lock().await;
     let (broadcast_rx, cancel_rx) = &mut *g;
     loop {
diff --git a/ext/broadcast_channel/lib.rs b/ext/broadcast_channel/lib.rs
index 47c48656d8..c1de118a36 100644
--- a/ext/broadcast_channel/lib.rs
+++ b/ext/broadcast_channel/lib.rs
@@ -10,34 +10,69 @@ use std::path::PathBuf;
 use std::rc::Rc;
 
 use async_trait::async_trait;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::JsBuffer;
 use deno_core::OpState;
 use deno_core::Resource;
 use deno_core::ResourceId;
+use tokio::sync::broadcast::error::SendError as BroadcastSendError;
+use tokio::sync::mpsc::error::SendError as MpscSendError;
 
 pub const UNSTABLE_FEATURE_NAME: &str = "broadcast-channel";
 
+#[derive(Debug, thiserror::Error)]
+pub enum BroadcastChannelError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  MPSCSendError(MpscSendError<Box<dyn std::fmt::Debug + Send + Sync>>),
+  #[error(transparent)]
+  BroadcastSendError(
+    BroadcastSendError<Box<dyn std::fmt::Debug + Send + Sync>>,
+  ),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
+impl<T: std::fmt::Debug + Send + Sync + 'static> From<MpscSendError<T>>
+  for BroadcastChannelError
+{
+  fn from(value: MpscSendError<T>) -> Self {
+    BroadcastChannelError::MPSCSendError(MpscSendError(Box::new(value.0)))
+  }
+}
+impl<T: std::fmt::Debug + Send + Sync + 'static> From<BroadcastSendError<T>>
+  for BroadcastChannelError
+{
+  fn from(value: BroadcastSendError<T>) -> Self {
+    BroadcastChannelError::BroadcastSendError(BroadcastSendError(Box::new(
+      value.0,
+    )))
+  }
+}
+
 #[async_trait]
 pub trait BroadcastChannel: Clone {
   type Resource: Resource;
 
-  fn subscribe(&self) -> Result<Self::Resource, AnyError>;
+  fn subscribe(&self) -> Result<Self::Resource, BroadcastChannelError>;
 
-  fn unsubscribe(&self, resource: &Self::Resource) -> Result<(), AnyError>;
+  fn unsubscribe(
+    &self,
+    resource: &Self::Resource,
+  ) -> Result<(), BroadcastChannelError>;
 
   async fn send(
     &self,
     resource: &Self::Resource,
     name: String,
     data: Vec<u8>,
-  ) -> Result<(), AnyError>;
+  ) -> Result<(), BroadcastChannelError>;
 
   async fn recv(
     &self,
     resource: &Self::Resource,
-  ) -> Result<Option<Message>, AnyError>;
+  ) -> Result<Option<Message>, BroadcastChannelError>;
 }
 
 pub type Message = (String, Vec<u8>);
@@ -46,7 +81,7 @@ pub type Message = (String, Vec<u8>);
 #[smi]
 pub fn op_broadcast_subscribe<BC>(
   state: &mut OpState,
-) -> Result<ResourceId, AnyError>
+) -> Result<ResourceId, BroadcastChannelError>
 where
   BC: BroadcastChannel + 'static,
 {
@@ -62,11 +97,14 @@ where
 pub fn op_broadcast_unsubscribe<BC>(
   state: &mut OpState,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError>
+) -> Result<(), BroadcastChannelError>
 where
   BC: BroadcastChannel + 'static,
 {
-  let resource = state.resource_table.get::<BC::Resource>(rid)?;
+  let resource = state
+    .resource_table
+    .get::<BC::Resource>(rid)
+    .map_err(BroadcastChannelError::Resource)?;
   let bc = state.borrow::<BC>();
   bc.unsubscribe(&resource)
 }
@@ -77,11 +115,15 @@ pub async fn op_broadcast_send<BC>(
   #[smi] rid: ResourceId,
   #[string] name: String,
   #[buffer] buf: JsBuffer,
-) -> Result<(), AnyError>
+) -> Result<(), BroadcastChannelError>
 where
   BC: BroadcastChannel + 'static,
 {
-  let resource = state.borrow().resource_table.get::<BC::Resource>(rid)?;
+  let resource = state
+    .borrow()
+    .resource_table
+    .get::<BC::Resource>(rid)
+    .map_err(BroadcastChannelError::Resource)?;
   let bc = state.borrow().borrow::<BC>().clone();
   bc.send(&resource, name, buf.to_vec()).await
 }
@@ -91,11 +133,15 @@ where
 pub async fn op_broadcast_recv<BC>(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<Option<Message>, AnyError>
+) -> Result<Option<Message>, BroadcastChannelError>
 where
   BC: BroadcastChannel + 'static,
 {
-  let resource = state.borrow().resource_table.get::<BC::Resource>(rid)?;
+  let resource = state
+    .borrow()
+    .resource_table
+    .get::<BC::Resource>(rid)
+    .map_err(BroadcastChannelError::Resource)?;
   let bc = state.borrow().borrow::<BC>().clone();
   bc.recv(&resource).await
 }
diff --git a/ext/cache/Cargo.toml b/ext/cache/Cargo.toml
index 5c6f162f17..56fa0a527f 100644
--- a/ext/cache/Cargo.toml
+++ b/ext/cache/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_cache"
-version = "0.100.0"
+version = "0.109.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -19,4 +19,5 @@ deno_core.workspace = true
 rusqlite.workspace = true
 serde.workspace = true
 sha2.workspace = true
+thiserror.workspace = true
 tokio.workspace = true
diff --git a/ext/cache/lib.rs b/ext/cache/lib.rs
index f6d758b95c..524d4cea05 100644
--- a/ext/cache/lib.rs
+++ b/ext/cache/lib.rs
@@ -7,7 +7,6 @@ use std::sync::Arc;
 
 use async_trait::async_trait;
 use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::serde::Deserialize;
 use deno_core::serde::Serialize;
@@ -19,8 +18,24 @@ use deno_core::ResourceId;
 mod sqlite;
 pub use sqlite::SqliteBackedCache;
 
+#[derive(Debug, thiserror::Error)]
+pub enum CacheError {
+  #[error(transparent)]
+  Sqlite(#[from] rusqlite::Error),
+  #[error(transparent)]
+  JoinError(#[from] tokio::task::JoinError),
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+}
+
 #[derive(Clone)]
-pub struct CreateCache<C: Cache + 'static>(pub Arc<dyn Fn() -> C>);
+pub struct CreateCache<C: Cache + 'static>(
+  pub Arc<dyn Fn() -> Result<C, CacheError>>,
+);
 
 deno_core::extension!(deno_cache,
   deps = [ deno_webidl, deno_web, deno_url, deno_fetch ],
@@ -92,26 +107,31 @@ pub struct CacheDeleteRequest {
 pub trait Cache: Clone + 'static {
   type CacheMatchResourceType: Resource;
 
-  async fn storage_open(&self, cache_name: String) -> Result<i64, AnyError>;
-  async fn storage_has(&self, cache_name: String) -> Result<bool, AnyError>;
-  async fn storage_delete(&self, cache_name: String) -> Result<bool, AnyError>;
+  async fn storage_open(&self, cache_name: String) -> Result<i64, CacheError>;
+  async fn storage_has(&self, cache_name: String) -> Result<bool, CacheError>;
+  async fn storage_delete(
+    &self,
+    cache_name: String,
+  ) -> Result<bool, CacheError>;
 
   /// Put a resource into the cache.
   async fn put(
     &self,
     request_response: CachePutRequest,
     resource: Option<Rc<dyn Resource>>,
-  ) -> Result<(), AnyError>;
+  ) -> Result<(), CacheError>;
 
   async fn r#match(
     &self,
     request: CacheMatchRequest,
   ) -> Result<
     Option<(CacheMatchResponseMeta, Option<Self::CacheMatchResourceType>)>,
-    AnyError,
+    CacheError,
   >;
-  async fn delete(&self, request: CacheDeleteRequest)
-    -> Result<bool, AnyError>;
+  async fn delete(
+    &self,
+    request: CacheDeleteRequest,
+  ) -> Result<bool, CacheError>;
 }
 
 #[op2(async)]
@@ -119,7 +139,7 @@ pub trait Cache: Clone + 'static {
 pub async fn op_cache_storage_open<CA>(
   state: Rc<RefCell<OpState>>,
   #[string] cache_name: String,
-) -> Result<i64, AnyError>
+) -> Result<i64, CacheError>
 where
   CA: Cache,
 {
@@ -131,7 +151,7 @@ where
 pub async fn op_cache_storage_has<CA>(
   state: Rc<RefCell<OpState>>,
   #[string] cache_name: String,
-) -> Result<bool, AnyError>
+) -> Result<bool, CacheError>
 where
   CA: Cache,
 {
@@ -143,7 +163,7 @@ where
 pub async fn op_cache_storage_delete<CA>(
   state: Rc<RefCell<OpState>>,
   #[string] cache_name: String,
-) -> Result<bool, AnyError>
+) -> Result<bool, CacheError>
 where
   CA: Cache,
 {
@@ -155,13 +175,19 @@ where
 pub async fn op_cache_put<CA>(
   state: Rc<RefCell<OpState>>,
   #[serde] request_response: CachePutRequest,
-) -> Result<(), AnyError>
+) -> Result<(), CacheError>
 where
   CA: Cache,
 {
   let cache = get_cache::<CA>(&state)?;
   let resource = match request_response.response_rid {
-    Some(rid) => Some(state.borrow_mut().resource_table.take_any(rid)?),
+    Some(rid) => Some(
+      state
+        .borrow_mut()
+        .resource_table
+        .take_any(rid)
+        .map_err(CacheError::Resource)?,
+    ),
     None => None,
   };
   cache.put(request_response, resource).await
@@ -172,7 +198,7 @@ where
 pub async fn op_cache_match<CA>(
   state: Rc<RefCell<OpState>>,
   #[serde] request: CacheMatchRequest,
-) -> Result<Option<CacheMatchResponse>, AnyError>
+) -> Result<Option<CacheMatchResponse>, CacheError>
 where
   CA: Cache,
 {
@@ -191,7 +217,7 @@ where
 pub async fn op_cache_delete<CA>(
   state: Rc<RefCell<OpState>>,
   #[serde] request: CacheDeleteRequest,
-) -> Result<bool, AnyError>
+) -> Result<bool, CacheError>
 where
   CA: Cache,
 {
@@ -199,7 +225,7 @@ where
   cache.delete(request).await
 }
 
-pub fn get_cache<CA>(state: &Rc<RefCell<OpState>>) -> Result<CA, AnyError>
+pub fn get_cache<CA>(state: &Rc<RefCell<OpState>>) -> Result<CA, CacheError>
 where
   CA: Cache,
 {
@@ -207,11 +233,13 @@ where
   if let Some(cache) = state.try_borrow::<CA>() {
     Ok(cache.clone())
   } else if let Some(create_cache) = state.try_borrow::<CreateCache<CA>>() {
-    let cache = create_cache.0();
+    let cache = create_cache.0()?;
     state.put(cache);
     Ok(state.borrow::<CA>().clone())
   } else {
-    Err(type_error("CacheStorage is not available in this context"))
+    Err(CacheError::Other(type_error(
+      "CacheStorage is not available in this context",
+    )))
   }
 }
 
diff --git a/ext/cache/sqlite.rs b/ext/cache/sqlite.rs
index c3c55dd5e9..6efceda11e 100644
--- a/ext/cache/sqlite.rs
+++ b/ext/cache/sqlite.rs
@@ -30,6 +30,7 @@ use crate::serialize_headers;
 use crate::vary_header_matches;
 use crate::Cache;
 use crate::CacheDeleteRequest;
+use crate::CacheError;
 use crate::CacheMatchRequest;
 use crate::CacheMatchResponseMeta;
 use crate::CachePutRequest;
@@ -41,7 +42,7 @@ pub struct SqliteBackedCache {
 }
 
 impl SqliteBackedCache {
-  pub fn new(cache_storage_dir: PathBuf) -> Self {
+  pub fn new(cache_storage_dir: PathBuf) -> Result<Self, CacheError> {
     {
       std::fs::create_dir_all(&cache_storage_dir)
         .expect("failed to create cache dir");
@@ -56,18 +57,14 @@ impl SqliteBackedCache {
         PRAGMA synchronous=NORMAL;
         PRAGMA optimize;
       ";
-      connection
-        .execute_batch(initial_pragmas)
-        .expect("failed to execute pragmas");
-      connection
-        .execute(
-          "CREATE TABLE IF NOT EXISTS cache_storage (
+      connection.execute_batch(initial_pragmas)?;
+      connection.execute(
+        "CREATE TABLE IF NOT EXISTS cache_storage (
                     id              INTEGER PRIMARY KEY,
                     cache_name      TEXT NOT NULL UNIQUE
                 )",
-          (),
-        )
-        .expect("failed to create cache_storage table");
+        (),
+      )?;
       connection
         .execute(
           "CREATE TABLE IF NOT EXISTS request_response_list (
@@ -85,12 +82,11 @@ impl SqliteBackedCache {
                     UNIQUE (cache_id, request_url)
                 )",
           (),
-        )
-        .expect("failed to create request_response_list table");
-      SqliteBackedCache {
+        )?;
+      Ok(SqliteBackedCache {
         connection: Arc::new(Mutex::new(connection)),
         cache_storage_dir,
-      }
+      })
     }
   }
 }
@@ -102,7 +98,7 @@ impl Cache for SqliteBackedCache {
   /// Open a cache storage. Internally, this creates a row in the
   /// sqlite db if the cache doesn't exist and returns the internal id
   /// of the cache.
-  async fn storage_open(&self, cache_name: String) -> Result<i64, AnyError> {
+  async fn storage_open(&self, cache_name: String) -> Result<i64, CacheError> {
     let db = self.connection.clone();
     let cache_storage_dir = self.cache_storage_dir.clone();
     spawn_blocking(move || {
@@ -121,14 +117,14 @@ impl Cache for SqliteBackedCache {
       )?;
       let responses_dir = get_responses_dir(cache_storage_dir, cache_id);
       std::fs::create_dir_all(responses_dir)?;
-      Ok::<i64, AnyError>(cache_id)
+      Ok::<i64, CacheError>(cache_id)
     })
     .await?
   }
 
   /// Check if a cache with the provided name exists.
   /// Note: this doesn't check the disk, it only checks the sqlite db.
-  async fn storage_has(&self, cache_name: String) -> Result<bool, AnyError> {
+  async fn storage_has(&self, cache_name: String) -> Result<bool, CacheError> {
     let db = self.connection.clone();
     spawn_blocking(move || {
       let db = db.lock();
@@ -140,13 +136,16 @@ impl Cache for SqliteBackedCache {
           Ok(count > 0)
         },
       )?;
-      Ok::<bool, AnyError>(cache_exists)
+      Ok::<bool, CacheError>(cache_exists)
     })
     .await?
   }
 
   /// Delete a cache storage. Internally, this deletes the row in the sqlite db.
-  async fn storage_delete(&self, cache_name: String) -> Result<bool, AnyError> {
+  async fn storage_delete(
+    &self,
+    cache_name: String,
+  ) -> Result<bool, CacheError> {
     let db = self.connection.clone();
     let cache_storage_dir = self.cache_storage_dir.clone();
     spawn_blocking(move || {
@@ -167,7 +166,7 @@ impl Cache for SqliteBackedCache {
           std::fs::remove_dir_all(cache_dir)?;
         }
       }
-      Ok::<bool, AnyError>(maybe_cache_id.is_some())
+      Ok::<bool, CacheError>(maybe_cache_id.is_some())
     })
     .await?
   }
@@ -176,10 +175,12 @@ impl Cache for SqliteBackedCache {
     &self,
     request_response: CachePutRequest,
     resource: Option<Rc<dyn Resource>>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), CacheError> {
     let db = self.connection.clone();
     let cache_storage_dir = self.cache_storage_dir.clone();
-    let now = SystemTime::now().duration_since(UNIX_EPOCH)?;
+    let now = SystemTime::now()
+      .duration_since(UNIX_EPOCH)
+      .expect("SystemTime is before unix epoch");
 
     if let Some(resource) = resource {
       let body_key = hash(&format!(
@@ -193,7 +194,11 @@ impl Cache for SqliteBackedCache {
       let mut file = tokio::fs::File::create(response_path).await?;
       let mut buf = BufMutView::new(64 * 1024);
       loop {
-        let (size, buf2) = resource.clone().read_byob(buf).await?;
+        let (size, buf2) = resource
+          .clone()
+          .read_byob(buf)
+          .await
+          .map_err(CacheError::Other)?;
         if size == 0 {
           break;
         }
@@ -224,7 +229,7 @@ impl Cache for SqliteBackedCache {
     request: CacheMatchRequest,
   ) -> Result<
     Option<(CacheMatchResponseMeta, Option<CacheResponseResource>)>,
-    AnyError,
+    CacheError,
   > {
     let db = self.connection.clone();
     let cache_storage_dir = self.cache_storage_dir.clone();
@@ -290,19 +295,17 @@ impl Cache for SqliteBackedCache {
           }
           Err(err) => return Err(err.into()),
         };
-        return Ok(Some((cache_meta, Some(CacheResponseResource::new(file)))));
+        Ok(Some((cache_meta, Some(CacheResponseResource::new(file)))))
       }
-      Some((cache_meta, None)) => {
-        return Ok(Some((cache_meta, None)));
-      }
-      None => return Ok(None),
+      Some((cache_meta, None)) => Ok(Some((cache_meta, None))),
+      None => Ok(None),
     }
   }
 
   async fn delete(
     &self,
     request: CacheDeleteRequest,
-  ) -> Result<bool, AnyError> {
+  ) -> Result<bool, CacheError> {
     let db = self.connection.clone();
     spawn_blocking(move || {
       // TODO(@satyarohith): remove the response body from disk if one exists
@@ -311,17 +314,17 @@ impl Cache for SqliteBackedCache {
         "DELETE FROM request_response_list WHERE cache_id = ?1 AND request_url = ?2",
         (request.cache_id, &request.request_url),
       )?;
-      Ok::<bool, AnyError>(rows_effected > 0)
+      Ok::<bool, CacheError>(rows_effected > 0)
     })
     .await?
   }
 }
 
 async fn insert_cache_asset(
-  db: Arc<Mutex<rusqlite::Connection>>,
+  db: Arc<Mutex<Connection>>,
   put: CachePutRequest,
   response_body_key: Option<String>,
-) -> Result<Option<String>, deno_core::anyhow::Error> {
+) -> Result<Option<String>, CacheError> {
   spawn_blocking(move || {
     let maybe_response_body = {
       let db = db.lock();
@@ -339,7 +342,7 @@ async fn insert_cache_asset(
           response_body_key,
           put.response_status,
           put.response_status_text,
-          SystemTime::now().duration_since(UNIX_EPOCH)?.as_secs(),
+          SystemTime::now().duration_since(UNIX_EPOCH).expect("SystemTime is before unix epoch").as_secs(),
         ),
         |row| {
           let response_body_key: Option<String> = row.get(0)?;
@@ -347,7 +350,7 @@ async fn insert_cache_asset(
         },
       )?
     };
-      Ok::<Option<String>, AnyError>(maybe_response_body)
+    Ok::<Option<String>, CacheError>(maybe_response_body)
   }).await?
 }
 
diff --git a/ext/canvas/Cargo.toml b/ext/canvas/Cargo.toml
index 96881682a4..4231d7c84d 100644
--- a/ext/canvas/Cargo.toml
+++ b/ext/canvas/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_canvas"
-version = "0.37.0"
+version = "0.46.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -18,3 +18,4 @@ deno_core.workspace = true
 deno_webgpu.workspace = true
 image = { version = "0.24.7", default-features = false, features = ["png"] }
 serde = { workspace = true, features = ["derive"] }
+thiserror.workspace = true
diff --git a/ext/canvas/lib.rs b/ext/canvas/lib.rs
index 72173f1331..defb288ac9 100644
--- a/ext/canvas/lib.rs
+++ b/ext/canvas/lib.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::ToJsBuffer;
 use image::imageops::FilterType;
@@ -13,6 +11,14 @@ use serde::Deserialize;
 use serde::Serialize;
 use std::path::PathBuf;
 
+#[derive(Debug, thiserror::Error)]
+pub enum CanvasError {
+  #[error("Color type '{0:?}' not supported")]
+  UnsupportedColorType(ColorType),
+  #[error(transparent)]
+  Image(#[from] image::ImageError),
+}
+
 #[derive(Debug, Deserialize)]
 #[serde(rename_all = "snake_case")]
 enum ImageResizeQuality {
@@ -43,7 +49,7 @@ struct ImageProcessArgs {
 fn op_image_process(
   #[buffer] buf: &[u8],
   #[serde] args: ImageProcessArgs,
-) -> Result<ToJsBuffer, AnyError> {
+) -> ToJsBuffer {
   let view =
     RgbaImage::from_vec(args.width, args.height, buf.to_vec()).unwrap();
 
@@ -105,7 +111,7 @@ fn op_image_process(
     }
   }
 
-  Ok(image_out.to_vec().into())
+  image_out.to_vec().into()
 }
 
 #[derive(Debug, Serialize)]
@@ -117,17 +123,16 @@ struct DecodedPng {
 
 #[op2]
 #[serde]
-fn op_image_decode_png(#[buffer] buf: &[u8]) -> Result<DecodedPng, AnyError> {
+fn op_image_decode_png(
+  #[buffer] buf: &[u8],
+) -> Result<DecodedPng, CanvasError> {
   let png = image::codecs::png::PngDecoder::new(buf)?;
 
   let (width, height) = png.dimensions();
 
   // TODO(@crowlKats): maybe use DynamicImage https://docs.rs/image/0.24.7/image/enum.DynamicImage.html ?
   if png.color_type() != ColorType::Rgba8 {
-    return Err(type_error(format!(
-      "Color type '{:?}' not supported",
-      png.color_type()
-    )));
+    return Err(CanvasError::UnsupportedColorType(png.color_type()));
   }
 
   // read_image will assert that the buffer is the correct size, so we need to fill it with zeros
diff --git a/ext/console/01_console.js b/ext/console/01_console.js
index 1ca23d5a49..3803492b90 100644
--- a/ext/console/01_console.js
+++ b/ext/console/01_console.js
@@ -84,6 +84,7 @@ const {
   NumberIsInteger,
   NumberIsNaN,
   NumberParseInt,
+  NumberParseFloat,
   NumberPrototypeToFixed,
   NumberPrototypeToString,
   NumberPrototypeValueOf,
@@ -1301,7 +1302,9 @@ function getKeys(value, showHidden) {
       ArrayPrototypePushApply(keys, ArrayPrototypeFilter(symbols, filter));
     }
   }
-  keys = ArrayPrototypeFilter(keys, (key) => key !== "cause");
+  if (ObjectPrototypeIsPrototypeOf(ErrorPrototype, value)) {
+    keys = ArrayPrototypeFilter(keys, (key) => key !== "cause");
+  }
   return keys;
 }
 
@@ -2650,6 +2653,7 @@ const HSL_PATTERN = new SafeRegExp(
 );
 
 function parseCssColor(colorString) {
+  colorString = StringPrototypeToLowerCase(colorString);
   if (colorKeywords.has(colorString)) {
     colorString = colorKeywords.get(colorString);
   }
@@ -3008,20 +3012,18 @@ function inspectArgs(args, inspectOptions = { __proto__: null }) {
           } else if (ArrayPrototypeIncludes(["d", "i"], char)) {
             // Format as an integer.
             const value = args[a++];
-            if (typeof value == "bigint") {
-              formattedArg = `${value}n`;
-            } else if (typeof value == "number") {
-              formattedArg = `${NumberParseInt(String(value))}`;
-            } else {
+            if (typeof value === "symbol") {
               formattedArg = "NaN";
+            } else {
+              formattedArg = `${NumberParseInt(value)}`;
             }
           } else if (char == "f") {
             // Format as a floating point value.
             const value = args[a++];
-            if (typeof value == "number") {
-              formattedArg = `${value}`;
-            } else {
+            if (typeof value === "symbol") {
               formattedArg = "NaN";
+            } else {
+              formattedArg = `${NumberParseFloat(value)}`;
             }
           } else if (ArrayPrototypeIncludes(["O", "o"], char)) {
             // Format as an object.
@@ -3255,7 +3257,7 @@ class Console {
 
     const stringifyValue = (value) =>
       inspectValueWithQuotes(value, {
-        ...getDefaultInspectOptions(),
+        ...getConsoleInspectOptions(noColorStdout()),
         depth: 1,
         compact: true,
       });
diff --git a/ext/console/Cargo.toml b/ext/console/Cargo.toml
index ef64398584..80f1cca84d 100644
--- a/ext/console/Cargo.toml
+++ b/ext/console/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_console"
-version = "0.168.0"
+version = "0.177.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/cron/Cargo.toml b/ext/cron/Cargo.toml
index 966ac450e9..966ccdc958 100644
--- a/ext/cron/Cargo.toml
+++ b/ext/cron/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_cron"
-version = "0.48.0"
+version = "0.57.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -19,4 +19,5 @@ async-trait.workspace = true
 chrono = { workspace = true, features = ["now"] }
 deno_core.workspace = true
 saffron.workspace = true
+thiserror.workspace = true
 tokio.workspace = true
diff --git a/ext/cron/interface.rs b/ext/cron/interface.rs
index 01b1d17895..a19525cc4e 100644
--- a/ext/cron/interface.rs
+++ b/ext/cron/interface.rs
@@ -1,17 +1,17 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
+use crate::CronError;
 use async_trait::async_trait;
-use deno_core::error::AnyError;
 
 pub trait CronHandler {
   type EH: CronHandle + 'static;
 
-  fn create(&self, spec: CronSpec) -> Result<Self::EH, AnyError>;
+  fn create(&self, spec: CronSpec) -> Result<Self::EH, CronError>;
 }
 
 #[async_trait(?Send)]
 pub trait CronHandle {
-  async fn next(&self, prev_success: bool) -> Result<bool, AnyError>;
+  async fn next(&self, prev_success: bool) -> Result<bool, CronError>;
   fn close(&self);
 }
 
diff --git a/ext/cron/lib.rs b/ext/cron/lib.rs
index e350e4d698..feffb5e511 100644
--- a/ext/cron/lib.rs
+++ b/ext/cron/lib.rs
@@ -7,16 +7,13 @@ use std::borrow::Cow;
 use std::cell::RefCell;
 use std::rc::Rc;
 
+pub use crate::interface::*;
 use deno_core::error::get_custom_error_class;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::Resource;
 use deno_core::ResourceId;
 
-pub use crate::interface::*;
-
 pub const UNSTABLE_FEATURE_NAME: &str = "cron";
 
 deno_core::extension!(deno_cron,
@@ -49,6 +46,28 @@ impl<EH: CronHandle + 'static> Resource for CronResource<EH> {
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum CronError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("Cron name cannot exceed 64 characters: current length {0}")]
+  NameExceeded(usize),
+  #[error("Invalid cron name: only alphanumeric characters, whitespace, hyphens, and underscores are allowed")]
+  NameInvalid,
+  #[error("Cron with this name already exists")]
+  AlreadyExists,
+  #[error("Too many crons")]
+  TooManyCrons,
+  #[error("Invalid cron schedule")]
+  InvalidCron,
+  #[error("Invalid backoff schedule")]
+  InvalidBackoff,
+  #[error(transparent)]
+  AcquireError(#[from] tokio::sync::AcquireError),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
 #[op2]
 #[smi]
 fn op_cron_create<C>(
@@ -56,7 +75,7 @@ fn op_cron_create<C>(
   #[string] name: String,
   #[string] cron_schedule: String,
   #[serde] backoff_schedule: Option<Vec<u32>>,
-) -> Result<ResourceId, AnyError>
+) -> Result<ResourceId, CronError>
 where
   C: CronHandler + 'static,
 {
@@ -90,7 +109,7 @@ async fn op_cron_next<C>(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   prev_success: bool,
-) -> Result<bool, AnyError>
+) -> Result<bool, CronError>
 where
   C: CronHandler + 'static,
 {
@@ -102,7 +121,7 @@ where
         if get_custom_error_class(&err) == Some("BadResource") {
           return Ok(false);
         } else {
-          return Err(err);
+          return Err(CronError::Resource(err));
         }
       }
     };
@@ -112,17 +131,14 @@ where
   cron_handler.next(prev_success).await
 }
 
-fn validate_cron_name(name: &str) -> Result<(), AnyError> {
+fn validate_cron_name(name: &str) -> Result<(), CronError> {
   if name.len() > 64 {
-    return Err(type_error(format!(
-      "Cron name cannot exceed 64 characters: current length {}",
-      name.len()
-    )));
+    return Err(CronError::NameExceeded(name.len()));
   }
   if !name.chars().all(|c| {
     c.is_ascii_whitespace() || c.is_ascii_alphanumeric() || c == '_' || c == '-'
   }) {
-    return Err(type_error("Invalid cron name: only alphanumeric characters, whitespace, hyphens, and underscores are allowed"));
+    return Err(CronError::NameInvalid);
   }
   Ok(())
 }
diff --git a/ext/cron/local.rs b/ext/cron/local.rs
index dd60e750a0..1110baadb8 100644
--- a/ext/cron/local.rs
+++ b/ext/cron/local.rs
@@ -10,8 +10,6 @@ use std::rc::Weak;
 use std::sync::Arc;
 
 use async_trait::async_trait;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::futures;
 use deno_core::futures::FutureExt;
 use deno_core::unsync::spawn;
@@ -21,6 +19,7 @@ use tokio::sync::mpsc::WeakSender;
 use tokio::sync::OwnedSemaphorePermit;
 use tokio::sync::Semaphore;
 
+use crate::CronError;
 use crate::CronHandle;
 use crate::CronHandler;
 use crate::CronSpec;
@@ -81,7 +80,7 @@ impl LocalCronHandler {
   async fn cron_loop(
     runtime_state: Rc<RefCell<RuntimeState>>,
     mut cron_schedule_rx: mpsc::Receiver<(String, bool)>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), CronError> {
     loop {
       let earliest_deadline = runtime_state
         .borrow()
@@ -154,7 +153,7 @@ impl LocalCronHandler {
 impl RuntimeState {
   fn get_ready_crons(
     &mut self,
-  ) -> Result<Vec<(String, WeakSender<()>)>, AnyError> {
+  ) -> Result<Vec<(String, WeakSender<()>)>, CronError> {
     let now = chrono::Utc::now().timestamp_millis() as u64;
 
     let ready = {
@@ -191,7 +190,7 @@ impl RuntimeState {
 impl CronHandler for LocalCronHandler {
   type EH = CronExecutionHandle;
 
-  fn create(&self, spec: CronSpec) -> Result<Self::EH, AnyError> {
+  fn create(&self, spec: CronSpec) -> Result<Self::EH, CronError> {
     // Ensure that the cron loop is started.
     self.cron_loop_join_handle.get_or_init(|| {
       let (cron_schedule_tx, cron_schedule_rx) =
@@ -208,17 +207,17 @@ impl CronHandler for LocalCronHandler {
     let mut runtime_state = self.runtime_state.borrow_mut();
 
     if runtime_state.crons.len() > MAX_CRONS {
-      return Err(type_error("Too many crons"));
+      return Err(CronError::TooManyCrons);
     }
     if runtime_state.crons.contains_key(&spec.name) {
-      return Err(type_error("Cron with this name already exists"));
+      return Err(CronError::AlreadyExists);
     }
 
     // Validate schedule expression.
     spec
       .cron_schedule
       .parse::<saffron::Cron>()
-      .map_err(|_| type_error("Invalid cron schedule"))?;
+      .map_err(|_| CronError::InvalidCron)?;
 
     // Validate backoff_schedule.
     if let Some(backoff_schedule) = &spec.backoff_schedule {
@@ -263,7 +262,7 @@ struct Inner {
 
 #[async_trait(?Send)]
 impl CronHandle for CronExecutionHandle {
-  async fn next(&self, prev_success: bool) -> Result<bool, AnyError> {
+  async fn next(&self, prev_success: bool) -> Result<bool, CronError> {
     self.inner.borrow_mut().permit.take();
 
     if self
@@ -300,7 +299,7 @@ impl CronHandle for CronExecutionHandle {
   }
 }
 
-fn compute_next_deadline(cron_expression: &str) -> Result<u64, AnyError> {
+fn compute_next_deadline(cron_expression: &str) -> Result<u64, CronError> {
   let now = chrono::Utc::now();
 
   if let Ok(test_schedule) = env::var("DENO_CRON_TEST_SCHEDULE_OFFSET") {
@@ -311,19 +310,21 @@ fn compute_next_deadline(cron_expression: &str) -> Result<u64, AnyError> {
 
   let cron = cron_expression
     .parse::<saffron::Cron>()
-    .map_err(|_| anyhow::anyhow!("invalid cron expression"))?;
+    .map_err(|_| CronError::InvalidCron)?;
   let Some(next_deadline) = cron.next_after(now) else {
-    return Err(anyhow::anyhow!("invalid cron expression"));
+    return Err(CronError::InvalidCron);
   };
   Ok(next_deadline.timestamp_millis() as u64)
 }
 
-fn validate_backoff_schedule(backoff_schedule: &[u32]) -> Result<(), AnyError> {
+fn validate_backoff_schedule(
+  backoff_schedule: &[u32],
+) -> Result<(), CronError> {
   if backoff_schedule.len() > MAX_BACKOFF_COUNT {
-    return Err(type_error("Invalid backoff schedule"));
+    return Err(CronError::InvalidBackoff);
   }
   if backoff_schedule.iter().any(|s| *s > MAX_BACKOFF_MS) {
-    return Err(type_error("Invalid backoff schedule"));
+    return Err(CronError::InvalidBackoff);
   }
   Ok(())
 }
diff --git a/ext/crypto/00_crypto.js b/ext/crypto/00_crypto.js
index 8e43b76f7c..63b1905145 100644
--- a/ext/crypto/00_crypto.js
+++ b/ext/crypto/00_crypto.js
@@ -18,21 +18,27 @@ import {
   op_crypto_decrypt,
   op_crypto_derive_bits,
   op_crypto_derive_bits_x25519,
+  op_crypto_derive_bits_x448,
   op_crypto_encrypt,
   op_crypto_export_key,
   op_crypto_export_pkcs8_ed25519,
   op_crypto_export_pkcs8_x25519,
+  op_crypto_export_pkcs8_x448,
   op_crypto_export_spki_ed25519,
   op_crypto_export_spki_x25519,
+  op_crypto_export_spki_x448,
   op_crypto_generate_ed25519_keypair,
   op_crypto_generate_key,
   op_crypto_generate_x25519_keypair,
+  op_crypto_generate_x448_keypair,
   op_crypto_get_random_values,
   op_crypto_import_key,
   op_crypto_import_pkcs8_ed25519,
   op_crypto_import_pkcs8_x25519,
+  op_crypto_import_pkcs8_x448,
   op_crypto_import_spki_ed25519,
   op_crypto_import_spki_x25519,
+  op_crypto_import_spki_x448,
   op_crypto_jwk_x_ed25519,
   op_crypto_random_uuid,
   op_crypto_sign_ed25519,
@@ -134,6 +140,7 @@ const supportedAlgorithms = {
     "AES-KW": "AesKeyGenParams",
     "HMAC": "HmacKeyGenParams",
     "X25519": null,
+    "X448": null,
     "Ed25519": null,
   },
   "sign": {
@@ -165,12 +172,14 @@ const supportedAlgorithms = {
     "AES-KW": null,
     "Ed25519": null,
     "X25519": null,
+    "X448": null,
   },
   "deriveBits": {
     "HKDF": "HkdfParams",
     "PBKDF2": "Pbkdf2Params",
     "ECDH": "EcdhKeyDeriveParams",
     "X25519": "EcdhKeyDeriveParams",
+    "X448": "EcdhKeyDeriveParams",
   },
   "encrypt": {
     "RSA-OAEP": "RsaOaepParams",
@@ -1037,6 +1046,10 @@ class SubtleCrypto {
         result = exportKeyEd25519(format, key, innerKey);
         break;
       }
+      case "X448": {
+        result = exportKeyX448(format, key, innerKey);
+        break;
+      }
       case "X25519": {
         result = exportKeyX25519(format, key, innerKey);
         break;
@@ -1954,6 +1967,48 @@ async function generateKey(normalizedAlgorithm, extractable, usages) {
 
       return generateKeyAES(normalizedAlgorithm, extractable, usages);
     }
+    case "X448": {
+      if (
+        ArrayPrototypeFind(
+          usages,
+          (u) => !ArrayPrototypeIncludes(["deriveKey", "deriveBits"], u),
+        ) !== undefined
+      ) {
+        throw new DOMException("Invalid key usage", "SyntaxError");
+      }
+      const privateKeyData = new Uint8Array(56);
+      const publicKeyData = new Uint8Array(56);
+
+      op_crypto_generate_x448_keypair(privateKeyData, publicKeyData);
+
+      const handle = {};
+      WeakMapPrototypeSet(KEY_STORE, handle, privateKeyData);
+
+      const publicHandle = {};
+      WeakMapPrototypeSet(KEY_STORE, publicHandle, publicKeyData);
+
+      const algorithm = {
+        name: algorithmName,
+      };
+
+      const publicKey = constructKey(
+        "public",
+        true,
+        usageIntersection(usages, []),
+        algorithm,
+        publicHandle,
+      );
+
+      const privateKey = constructKey(
+        "private",
+        extractable,
+        usageIntersection(usages, ["deriveKey", "deriveBits"]),
+        algorithm,
+        handle,
+      );
+
+      return { publicKey, privateKey };
+    }
     case "X25519": {
       if (
         ArrayPrototypeFind(
@@ -2100,6 +2155,211 @@ async function generateKey(normalizedAlgorithm, extractable, usages) {
   }
 }
 
+function importKeyX448(
+  format,
+  keyData,
+  extractable,
+  keyUsages,
+) {
+  switch (format) {
+    case "raw": {
+      // 1.
+      if (keyUsages.length > 0) {
+        throw new DOMException("Invalid key usage", "SyntaxError");
+      }
+
+      const handle = {};
+      WeakMapPrototypeSet(KEY_STORE, handle, keyData);
+
+      // 2-3.
+      const algorithm = {
+        name: "X448",
+      };
+
+      // 4-6.
+      return constructKey(
+        "public",
+        extractable,
+        [],
+        algorithm,
+        handle,
+      );
+    }
+    case "spki": {
+      // 1.
+      if (keyUsages.length > 0) {
+        throw new DOMException("Invalid key usage", "SyntaxError");
+      }
+
+      const publicKeyData = new Uint8Array(56);
+      if (!op_crypto_import_spki_x448(keyData, publicKeyData)) {
+        throw new DOMException("Invalid key data", "DataError");
+      }
+
+      const handle = {};
+      WeakMapPrototypeSet(KEY_STORE, handle, publicKeyData);
+
+      const algorithm = {
+        name: "X448",
+      };
+
+      return constructKey(
+        "public",
+        extractable,
+        [],
+        algorithm,
+        handle,
+      );
+    }
+    case "pkcs8": {
+      // 1.
+      if (
+        ArrayPrototypeFind(
+          keyUsages,
+          (u) => !ArrayPrototypeIncludes(["deriveKey", "deriveBits"], u),
+        ) !== undefined
+      ) {
+        throw new DOMException("Invalid key usage", "SyntaxError");
+      }
+
+      const privateKeyData = new Uint8Array(32);
+      if (!op_crypto_import_pkcs8_x448(keyData, privateKeyData)) {
+        throw new DOMException("Invalid key data", "DataError");
+      }
+
+      const handle = {};
+      WeakMapPrototypeSet(KEY_STORE, handle, privateKeyData);
+
+      const algorithm = {
+        name: "X448",
+      };
+
+      return constructKey(
+        "private",
+        extractable,
+        usageIntersection(keyUsages, recognisedUsages),
+        algorithm,
+        handle,
+      );
+    }
+    case "jwk": {
+      // 1.
+      const jwk = keyData;
+
+      // 2.
+      if (jwk.d !== undefined) {
+        if (
+          ArrayPrototypeFind(
+            keyUsages,
+            (u) =>
+              !ArrayPrototypeIncludes(
+                ["deriveKey", "deriveBits"],
+                u,
+              ),
+          ) !== undefined
+        ) {
+          throw new DOMException("Invalid key usage", "SyntaxError");
+        }
+      }
+
+      // 3.
+      if (jwk.d === undefined && keyUsages.length > 0) {
+        throw new DOMException("Invalid key usage", "SyntaxError");
+      }
+
+      // 4.
+      if (jwk.kty !== "OKP") {
+        throw new DOMException("Invalid key type", "DataError");
+      }
+
+      // 5.
+      if (jwk.crv !== "X448") {
+        throw new DOMException("Invalid curve", "DataError");
+      }
+
+      // 6.
+      if (keyUsages.length > 0 && jwk.use !== undefined) {
+        if (jwk.use !== "enc") {
+          throw new DOMException("Invalid key use", "DataError");
+        }
+      }
+
+      // 7.
+      if (jwk.key_ops !== undefined) {
+        if (
+          ArrayPrototypeFind(
+            jwk.key_ops,
+            (u) => !ArrayPrototypeIncludes(recognisedUsages, u),
+          ) !== undefined
+        ) {
+          throw new DOMException(
+            "'key_ops' property of JsonWebKey is invalid",
+            "DataError",
+          );
+        }
+
+        if (
+          !ArrayPrototypeEvery(
+            jwk.key_ops,
+            (u) => ArrayPrototypeIncludes(keyUsages, u),
+          )
+        ) {
+          throw new DOMException(
+            "'key_ops' property of JsonWebKey is invalid",
+            "DataError",
+          );
+        }
+      }
+
+      // 8.
+      if (jwk.ext !== undefined && jwk.ext === false && extractable) {
+        throw new DOMException("Invalid key extractability", "DataError");
+      }
+
+      // 9.
+      if (jwk.d !== undefined) {
+        // https://www.rfc-editor.org/rfc/rfc8037#section-2
+        const privateKeyData = op_crypto_base64url_decode(jwk.d);
+
+        const handle = {};
+        WeakMapPrototypeSet(KEY_STORE, handle, privateKeyData);
+
+        const algorithm = {
+          name: "X448",
+        };
+
+        return constructKey(
+          "private",
+          extractable,
+          usageIntersection(keyUsages, ["deriveKey", "deriveBits"]),
+          algorithm,
+          handle,
+        );
+      } else {
+        // https://www.rfc-editor.org/rfc/rfc8037#section-2
+        const publicKeyData = op_crypto_base64url_decode(jwk.x);
+
+        const handle = {};
+        WeakMapPrototypeSet(KEY_STORE, handle, publicKeyData);
+
+        const algorithm = {
+          name: "X448",
+        };
+
+        return constructKey(
+          "public",
+          extractable,
+          [],
+          algorithm,
+          handle,
+        );
+      }
+    }
+    default:
+      throw new DOMException("Not implemented", "NotSupportedError");
+  }
+}
+
 function importKeyEd25519(
   format,
   keyData,
@@ -3358,6 +3618,14 @@ async function importKeyInner(
         ["wrapKey", "unwrapKey"],
       );
     }
+    case "X448": {
+      return importKeyX448(
+        format,
+        keyData,
+        extractable,
+        keyUsages,
+      );
+    }
     case "X25519": {
       return importKeyX25519(
         format,
@@ -4162,6 +4430,66 @@ function exportKeyEd25519(format, key, innerKey) {
   }
 }
 
+function exportKeyX448(format, key, innerKey) {
+  switch (format) {
+    case "raw": {
+      // 1.
+      if (key[_type] !== "public") {
+        throw new DOMException(
+          "Key is not a public key",
+          "InvalidAccessError",
+        );
+      }
+
+      // 2-3.
+      return TypedArrayPrototypeGetBuffer(innerKey);
+    }
+    case "spki": {
+      // 1.
+      if (key[_type] !== "public") {
+        throw new DOMException(
+          "Key is not a public key",
+          "InvalidAccessError",
+        );
+      }
+
+      const spkiDer = op_crypto_export_spki_x448(innerKey);
+      return TypedArrayPrototypeGetBuffer(spkiDer);
+    }
+    case "pkcs8": {
+      // 1.
+      if (key[_type] !== "private") {
+        throw new DOMException(
+          "Key is not a private key",
+          "InvalidAccessError",
+        );
+      }
+
+      const pkcs8Der = op_crypto_export_pkcs8_x448(
+        new Uint8Array([0x04, 0x22, ...new SafeArrayIterator(innerKey)]),
+      );
+      pkcs8Der[15] = 0x20;
+      return TypedArrayPrototypeGetBuffer(pkcs8Der);
+    }
+    case "jwk": {
+      if (key[_type] === "private") {
+        throw new DOMException("Not implemented", "NotSupportedError");
+      }
+      const x = op_crypto_base64url_encode(innerKey);
+      const jwk = {
+        kty: "OKP",
+        crv: "X448",
+        x,
+        "key_ops": key.usages,
+        ext: key[_extractable],
+      };
+      return jwk;
+    }
+    default:
+      throw new DOMException("Not implemented", "NotSupportedError");
+  }
+}
+
 function exportKeyX25519(format, key, innerKey) {
   switch (format) {
     case "raw": {
@@ -4519,6 +4847,55 @@ async function deriveBits(normalizedAlgorithm, baseKey, length) {
 
       return TypedArrayPrototypeGetBuffer(buf);
     }
+    case "X448": {
+      // 1.
+      if (baseKey[_type] !== "private") {
+        throw new DOMException("Invalid key type", "InvalidAccessError");
+      }
+      // 2.
+      const publicKey = normalizedAlgorithm.public;
+      // 3.
+      if (publicKey[_type] !== "public") {
+        throw new DOMException("Invalid key type", "InvalidAccessError");
+      }
+      // 4.
+      if (publicKey[_algorithm].name !== baseKey[_algorithm].name) {
+        throw new DOMException(
+          "Algorithm mismatch",
+          "InvalidAccessError",
+        );
+      }
+
+      // 5.
+      const kHandle = baseKey[_handle];
+      const k = WeakMapPrototypeGet(KEY_STORE, kHandle);
+
+      const uHandle = publicKey[_handle];
+      const u = WeakMapPrototypeGet(KEY_STORE, uHandle);
+
+      const secret = new Uint8Array(56);
+      const isIdentity = op_crypto_derive_bits_x448(k, u, secret);
+
+      // 6.
+      if (isIdentity) {
+        throw new DOMException("Invalid key", "OperationError");
+      }
+
+      // 7.
+      if (length === null) {
+        return TypedArrayPrototypeGetBuffer(secret);
+      } else if (
+        TypedArrayPrototypeGetByteLength(secret) * 8 < length
+      ) {
+        throw new DOMException("Invalid length", "OperationError");
+      } else {
+        return ArrayBufferPrototypeSlice(
+          TypedArrayPrototypeGetBuffer(secret),
+          0,
+          MathCeil(length / 8),
+        );
+      }
+    }
     case "X25519": {
       // 1.
       if (baseKey[_type] !== "private") {
diff --git a/ext/crypto/Cargo.toml b/ext/crypto/Cargo.toml
index 3f2a8d7030..a5794dc68b 100644
--- a/ext/crypto/Cargo.toml
+++ b/ext/crypto/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_crypto"
-version = "0.182.0"
+version = "0.191.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -24,6 +24,7 @@ ctr = "0.9.1"
 curve25519-dalek = "4.1.3"
 deno_core.workspace = true
 deno_web.workspace = true
+ed448-goldilocks = { version = "0.8.3", features = ["zeroize"] }
 elliptic-curve = { version = "0.13.1", features = ["std", "pem"] }
 num-traits = "0.2.14"
 once_cell.workspace = true
@@ -40,5 +41,7 @@ sha1.workspace = true
 sha2.workspace = true
 signature.workspace = true
 spki.workspace = true
+thiserror.workspace = true
+tokio.workspace = true
 uuid.workspace = true
 x25519-dalek = "2.0.0"
diff --git a/ext/crypto/decrypt.rs b/ext/crypto/decrypt.rs
index 9b104e1784..1140475183 100644
--- a/ext/crypto/decrypt.rs
+++ b/ext/crypto/decrypt.rs
@@ -16,9 +16,6 @@ use ctr::cipher::StreamCipher;
 use ctr::Ctr128BE;
 use ctr::Ctr32BE;
 use ctr::Ctr64BE;
-use deno_core::error::custom_error;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::unsync::spawn_blocking;
 use deno_core::JsBuffer;
@@ -73,12 +70,36 @@ pub enum DecryptAlgorithm {
   },
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum DecryptError {
+  #[error(transparent)]
+  General(#[from] SharedError),
+  #[error(transparent)]
+  Pkcs1(#[from] rsa::pkcs1::Error),
+  #[error("Decryption failed")]
+  Failed,
+  #[error("invalid length")]
+  InvalidLength,
+  #[error("invalid counter length. Currently supported 32/64/128 bits")]
+  InvalidCounterLength,
+  #[error("tag length not equal to 128")]
+  InvalidTagLength,
+  #[error("invalid key or iv")]
+  InvalidKeyOrIv,
+  #[error("tried to decrypt too much data")]
+  TooMuchData,
+  #[error("iv length not equal to 12 or 16")]
+  InvalidIvLength,
+  #[error("{0}")]
+  Rsa(rsa::Error),
+}
+
 #[op2(async)]
 #[serde]
 pub async fn op_crypto_decrypt(
   #[serde] opts: DecryptOptions,
   #[buffer] data: JsBuffer,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, DecryptError> {
   let key = opts.key;
   let fun = move || match opts.algorithm {
     DecryptAlgorithm::RsaOaep { hash, label } => {
@@ -108,7 +129,7 @@ fn decrypt_rsa_oaep(
   hash: ShaHash,
   label: Vec<u8>,
   data: &[u8],
-) -> Result<Vec<u8>, deno_core::anyhow::Error> {
+) -> Result<Vec<u8>, DecryptError> {
   let key = key.as_rsa_private_key()?;
 
   let private_key = rsa::RsaPrivateKey::from_pkcs1_der(key)?;
@@ -139,7 +160,7 @@ fn decrypt_rsa_oaep(
 
   private_key
     .decrypt(padding, data)
-    .map_err(|e| custom_error("DOMExceptionOperationError", e.to_string()))
+    .map_err(DecryptError::Rsa)
 }
 
 fn decrypt_aes_cbc(
@@ -147,7 +168,7 @@ fn decrypt_aes_cbc(
   length: usize,
   iv: Vec<u8>,
   data: &[u8],
-) -> Result<Vec<u8>, deno_core::anyhow::Error> {
+) -> Result<Vec<u8>, DecryptError> {
   let key = key.as_secret_key()?;
 
   // 2.
@@ -155,53 +176,32 @@ fn decrypt_aes_cbc(
     128 => {
       // Section 10.3 Step 2 of RFC 2315 https://www.rfc-editor.org/rfc/rfc2315
       type Aes128CbcDec = cbc::Decryptor<aes::Aes128>;
-      let cipher = Aes128CbcDec::new_from_slices(key, &iv).map_err(|_| {
-        custom_error(
-          "DOMExceptionOperationError",
-          "Invalid key or iv".to_string(),
-        )
-      })?;
+      let cipher = Aes128CbcDec::new_from_slices(key, &iv)
+        .map_err(|_| DecryptError::InvalidKeyOrIv)?;
 
-      cipher.decrypt_padded_vec_mut::<Pkcs7>(data).map_err(|_| {
-        custom_error(
-          "DOMExceptionOperationError",
-          "Decryption failed".to_string(),
-        )
-      })?
+      cipher
+        .decrypt_padded_vec_mut::<Pkcs7>(data)
+        .map_err(|_| DecryptError::Failed)?
     }
     192 => {
       // Section 10.3 Step 2 of RFC 2315 https://www.rfc-editor.org/rfc/rfc2315
       type Aes192CbcDec = cbc::Decryptor<aes::Aes192>;
-      let cipher = Aes192CbcDec::new_from_slices(key, &iv).map_err(|_| {
-        custom_error(
-          "DOMExceptionOperationError",
-          "Invalid key or iv".to_string(),
-        )
-      })?;
+      let cipher = Aes192CbcDec::new_from_slices(key, &iv)
+        .map_err(|_| DecryptError::InvalidKeyOrIv)?;
 
-      cipher.decrypt_padded_vec_mut::<Pkcs7>(data).map_err(|_| {
-        custom_error(
-          "DOMExceptionOperationError",
-          "Decryption failed".to_string(),
-        )
-      })?
+      cipher
+        .decrypt_padded_vec_mut::<Pkcs7>(data)
+        .map_err(|_| DecryptError::Failed)?
     }
     256 => {
       // Section 10.3 Step 2 of RFC 2315 https://www.rfc-editor.org/rfc/rfc2315
       type Aes256CbcDec = cbc::Decryptor<aes::Aes256>;
-      let cipher = Aes256CbcDec::new_from_slices(key, &iv).map_err(|_| {
-        custom_error(
-          "DOMExceptionOperationError",
-          "Invalid key or iv".to_string(),
-        )
-      })?;
+      let cipher = Aes256CbcDec::new_from_slices(key, &iv)
+        .map_err(|_| DecryptError::InvalidKeyOrIv)?;
 
-      cipher.decrypt_padded_vec_mut::<Pkcs7>(data).map_err(|_| {
-        custom_error(
-          "DOMExceptionOperationError",
-          "Decryption failed".to_string(),
-        )
-      })?
+      cipher
+        .decrypt_padded_vec_mut::<Pkcs7>(data)
+        .map_err(|_| DecryptError::Failed)?
     }
     _ => unreachable!(),
   };
@@ -214,7 +214,7 @@ fn decrypt_aes_ctr_gen<B>(
   key: &[u8],
   counter: &[u8],
   data: &[u8],
-) -> Result<Vec<u8>, AnyError>
+) -> Result<Vec<u8>, DecryptError>
 where
   B: KeyIvInit + StreamCipher,
 {
@@ -223,7 +223,7 @@ where
   let mut plaintext = data.to_vec();
   cipher
     .try_apply_keystream(&mut plaintext)
-    .map_err(|_| operation_error("tried to decrypt too much data"))?;
+    .map_err(|_| DecryptError::TooMuchData)?;
 
   Ok(plaintext)
 }
@@ -235,12 +235,12 @@ fn decrypt_aes_gcm_gen<N: ArrayLength<u8>>(
   length: usize,
   additional_data: Vec<u8>,
   plaintext: &mut [u8],
-) -> Result<(), AnyError> {
+) -> Result<(), DecryptError> {
   let nonce = Nonce::from_slice(nonce);
   match length {
     128 => {
       let cipher = aes_gcm::AesGcm::<Aes128, N>::new_from_slice(key)
-        .map_err(|_| operation_error("Decryption failed"))?;
+        .map_err(|_| DecryptError::Failed)?;
       cipher
         .decrypt_in_place_detached(
           nonce,
@@ -248,11 +248,11 @@ fn decrypt_aes_gcm_gen<N: ArrayLength<u8>>(
           plaintext,
           tag,
         )
-        .map_err(|_| operation_error("Decryption failed"))?
+        .map_err(|_| DecryptError::Failed)?
     }
     192 => {
       let cipher = aes_gcm::AesGcm::<Aes192, N>::new_from_slice(key)
-        .map_err(|_| operation_error("Decryption failed"))?;
+        .map_err(|_| DecryptError::Failed)?;
       cipher
         .decrypt_in_place_detached(
           nonce,
@@ -260,11 +260,11 @@ fn decrypt_aes_gcm_gen<N: ArrayLength<u8>>(
           plaintext,
           tag,
         )
-        .map_err(|_| operation_error("Decryption failed"))?
+        .map_err(|_| DecryptError::Failed)?
     }
     256 => {
       let cipher = aes_gcm::AesGcm::<Aes256, N>::new_from_slice(key)
-        .map_err(|_| operation_error("Decryption failed"))?;
+        .map_err(|_| DecryptError::Failed)?;
       cipher
         .decrypt_in_place_detached(
           nonce,
@@ -272,9 +272,9 @@ fn decrypt_aes_gcm_gen<N: ArrayLength<u8>>(
           plaintext,
           tag,
         )
-        .map_err(|_| operation_error("Decryption failed"))?
+        .map_err(|_| DecryptError::Failed)?
     }
-    _ => return Err(type_error("invalid length")),
+    _ => return Err(DecryptError::InvalidLength),
   };
 
   Ok(())
@@ -286,7 +286,7 @@ fn decrypt_aes_ctr(
   counter: &[u8],
   ctr_length: usize,
   data: &[u8],
-) -> Result<Vec<u8>, deno_core::anyhow::Error> {
+) -> Result<Vec<u8>, DecryptError> {
   let key = key.as_secret_key()?;
 
   match ctr_length {
@@ -294,23 +294,21 @@ fn decrypt_aes_ctr(
       128 => decrypt_aes_ctr_gen::<Ctr32BE<aes::Aes128>>(key, counter, data),
       192 => decrypt_aes_ctr_gen::<Ctr32BE<aes::Aes192>>(key, counter, data),
       256 => decrypt_aes_ctr_gen::<Ctr32BE<aes::Aes256>>(key, counter, data),
-      _ => Err(type_error("invalid length")),
+      _ => Err(DecryptError::InvalidLength),
     },
     64 => match key_length {
       128 => decrypt_aes_ctr_gen::<Ctr64BE<aes::Aes128>>(key, counter, data),
       192 => decrypt_aes_ctr_gen::<Ctr64BE<aes::Aes192>>(key, counter, data),
       256 => decrypt_aes_ctr_gen::<Ctr64BE<aes::Aes256>>(key, counter, data),
-      _ => Err(type_error("invalid length")),
+      _ => Err(DecryptError::InvalidLength),
     },
     128 => match key_length {
       128 => decrypt_aes_ctr_gen::<Ctr128BE<aes::Aes128>>(key, counter, data),
       192 => decrypt_aes_ctr_gen::<Ctr128BE<aes::Aes192>>(key, counter, data),
       256 => decrypt_aes_ctr_gen::<Ctr128BE<aes::Aes256>>(key, counter, data),
-      _ => Err(type_error("invalid length")),
+      _ => Err(DecryptError::InvalidLength),
     },
-    _ => Err(type_error(
-      "invalid counter length. Currently supported 32/64/128 bits",
-    )),
+    _ => Err(DecryptError::InvalidCounterLength),
   }
 }
 
@@ -321,7 +319,7 @@ fn decrypt_aes_gcm(
   iv: Vec<u8>,
   additional_data: Option<Vec<u8>>,
   data: &[u8],
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, DecryptError> {
   let key = key.as_secret_key()?;
   let additional_data = additional_data.unwrap_or_default();
 
@@ -330,7 +328,7 @@ fn decrypt_aes_gcm(
   // Note that encryption won't fail, it instead truncates the tag
   // to the specified tag length as specified in the spec.
   if tag_length != 128 {
-    return Err(type_error("tag length not equal to 128"));
+    return Err(DecryptError::InvalidTagLength);
   }
 
   let sep = data.len() - (tag_length / 8);
@@ -357,7 +355,7 @@ fn decrypt_aes_gcm(
       additional_data,
       &mut plaintext,
     )?,
-    _ => return Err(type_error("iv length not equal to 12 or 16")),
+    _ => return Err(DecryptError::InvalidIvLength),
   }
 
   Ok(plaintext)
diff --git a/ext/crypto/ed25519.rs b/ext/crypto/ed25519.rs
index 4f604fe513..da34b7d25d 100644
--- a/ext/crypto/ed25519.rs
+++ b/ext/crypto/ed25519.rs
@@ -2,8 +2,6 @@
 
 use base64::prelude::BASE64_URL_SAFE_NO_PAD;
 use base64::Engine;
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::ToJsBuffer;
 use elliptic_curve::pkcs8::PrivateKeyInfo;
@@ -15,6 +13,16 @@ use spki::der::asn1::BitString;
 use spki::der::Decode;
 use spki::der::Encode;
 
+#[derive(Debug, thiserror::Error)]
+pub enum Ed25519Error {
+  #[error("Failed to export key")]
+  FailedExport,
+  #[error(transparent)]
+  Der(#[from] rsa::pkcs1::der::Error),
+  #[error(transparent)]
+  KeyRejected(#[from] ring::error::KeyRejected),
+}
+
 #[op2(fast)]
 pub fn op_crypto_generate_ed25519_keypair(
   #[buffer] pkey: &mut [u8],
@@ -116,7 +124,7 @@ pub fn op_crypto_import_pkcs8_ed25519(
 #[serde]
 pub fn op_crypto_export_spki_ed25519(
   #[buffer] pubkey: &[u8],
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, Ed25519Error> {
   let key_info = spki::SubjectPublicKeyInfo {
     algorithm: spki::AlgorithmIdentifierOwned {
       // id-Ed25519
@@ -128,9 +136,7 @@ pub fn op_crypto_export_spki_ed25519(
   Ok(
     key_info
       .to_der()
-      .map_err(|_| {
-        custom_error("DOMExceptionOperationError", "Failed to export key")
-      })?
+      .map_err(|_| Ed25519Error::FailedExport)?
       .into(),
   )
 }
@@ -139,7 +145,7 @@ pub fn op_crypto_export_spki_ed25519(
 #[serde]
 pub fn op_crypto_export_pkcs8_ed25519(
   #[buffer] pkey: &[u8],
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, Ed25519Error> {
   use rsa::pkcs1::der::Encode;
 
   // This should probably use OneAsymmetricKey instead
@@ -164,7 +170,7 @@ pub fn op_crypto_export_pkcs8_ed25519(
 #[string]
 pub fn op_crypto_jwk_x_ed25519(
   #[buffer] pkey: &[u8],
-) -> Result<String, AnyError> {
+) -> Result<String, Ed25519Error> {
   let pair = Ed25519KeyPair::from_seed_unchecked(pkey)?;
   Ok(BASE64_URL_SAFE_NO_PAD.encode(pair.public_key().as_ref()))
 }
diff --git a/ext/crypto/encrypt.rs b/ext/crypto/encrypt.rs
index 204648e892..66b27657f8 100644
--- a/ext/crypto/encrypt.rs
+++ b/ext/crypto/encrypt.rs
@@ -16,8 +16,6 @@ use aes_gcm::Nonce;
 use ctr::Ctr128BE;
 use ctr::Ctr32BE;
 use ctr::Ctr64BE;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::unsync::spawn_blocking;
 use deno_core::JsBuffer;
@@ -73,12 +71,30 @@ pub enum EncryptAlgorithm {
   },
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum EncryptError {
+  #[error(transparent)]
+  General(#[from] SharedError),
+  #[error("invalid length")]
+  InvalidLength,
+  #[error("invalid key or iv")]
+  InvalidKeyOrIv,
+  #[error("iv length not equal to 12 or 16")]
+  InvalidIvLength,
+  #[error("invalid counter length. Currently supported 32/64/128 bits")]
+  InvalidCounterLength,
+  #[error("tried to encrypt too much data")]
+  TooMuchData,
+  #[error("Encryption failed")]
+  Failed,
+}
+
 #[op2(async)]
 #[serde]
 pub async fn op_crypto_encrypt(
   #[serde] opts: EncryptOptions,
   #[buffer] data: JsBuffer,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, EncryptError> {
   let key = opts.key;
   let fun = move || match opts.algorithm {
     EncryptAlgorithm::RsaOaep { hash, label } => {
@@ -108,12 +124,12 @@ fn encrypt_rsa_oaep(
   hash: ShaHash,
   label: Vec<u8>,
   data: &[u8],
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, EncryptError> {
   let label = String::from_utf8_lossy(&label).to_string();
 
   let public_key = key.as_rsa_public_key()?;
   let public_key = rsa::RsaPublicKey::from_pkcs1_der(&public_key)
-    .map_err(|_| operation_error("failed to decode public key"))?;
+    .map_err(|_| SharedError::FailedDecodePublicKey)?;
   let mut rng = OsRng;
   let padding = match hash {
     ShaHash::Sha1 => rsa::Oaep {
@@ -139,7 +155,7 @@ fn encrypt_rsa_oaep(
   };
   let encrypted = public_key
     .encrypt(&mut rng, padding, data)
-    .map_err(|_| operation_error("Encryption failed"))?;
+    .map_err(|_| EncryptError::Failed)?;
   Ok(encrypted)
 }
 
@@ -148,7 +164,7 @@ fn encrypt_aes_cbc(
   length: usize,
   iv: Vec<u8>,
   data: &[u8],
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, EncryptError> {
   let key = key.as_secret_key()?;
   let ciphertext = match length {
     128 => {
@@ -156,7 +172,7 @@ fn encrypt_aes_cbc(
       type Aes128CbcEnc = cbc::Encryptor<aes::Aes128>;
 
       let cipher = Aes128CbcEnc::new_from_slices(key, &iv)
-        .map_err(|_| operation_error("invalid key or iv".to_string()))?;
+        .map_err(|_| EncryptError::InvalidKeyOrIv)?;
       cipher.encrypt_padded_vec_mut::<Pkcs7>(data)
     }
     192 => {
@@ -164,7 +180,7 @@ fn encrypt_aes_cbc(
       type Aes192CbcEnc = cbc::Encryptor<aes::Aes192>;
 
       let cipher = Aes192CbcEnc::new_from_slices(key, &iv)
-        .map_err(|_| operation_error("invalid key or iv".to_string()))?;
+        .map_err(|_| EncryptError::InvalidKeyOrIv)?;
       cipher.encrypt_padded_vec_mut::<Pkcs7>(data)
     }
     256 => {
@@ -172,10 +188,10 @@ fn encrypt_aes_cbc(
       type Aes256CbcEnc = cbc::Encryptor<aes::Aes256>;
 
       let cipher = Aes256CbcEnc::new_from_slices(key, &iv)
-        .map_err(|_| operation_error("invalid key or iv".to_string()))?;
+        .map_err(|_| EncryptError::InvalidKeyOrIv)?;
       cipher.encrypt_padded_vec_mut::<Pkcs7>(data)
     }
-    _ => return Err(type_error("invalid length")),
+    _ => return Err(EncryptError::InvalidLength),
   };
   Ok(ciphertext)
 }
@@ -186,31 +202,31 @@ fn encrypt_aes_gcm_general<N: ArrayLength<u8>>(
   length: usize,
   ciphertext: &mut [u8],
   additional_data: Vec<u8>,
-) -> Result<aes_gcm::Tag, AnyError> {
+) -> Result<aes_gcm::Tag, EncryptError> {
   let nonce = Nonce::<N>::from_slice(&iv);
   let tag = match length {
     128 => {
       let cipher = aes_gcm::AesGcm::<Aes128, N>::new_from_slice(key)
-        .map_err(|_| operation_error("Encryption failed"))?;
+        .map_err(|_| EncryptError::Failed)?;
       cipher
         .encrypt_in_place_detached(nonce, &additional_data, ciphertext)
-        .map_err(|_| operation_error("Encryption failed"))?
+        .map_err(|_| EncryptError::Failed)?
     }
     192 => {
       let cipher = aes_gcm::AesGcm::<Aes192, N>::new_from_slice(key)
-        .map_err(|_| operation_error("Encryption failed"))?;
+        .map_err(|_| EncryptError::Failed)?;
       cipher
         .encrypt_in_place_detached(nonce, &additional_data, ciphertext)
-        .map_err(|_| operation_error("Encryption failed"))?
+        .map_err(|_| EncryptError::Failed)?
     }
     256 => {
       let cipher = aes_gcm::AesGcm::<Aes256, N>::new_from_slice(key)
-        .map_err(|_| operation_error("Encryption failed"))?;
+        .map_err(|_| EncryptError::Failed)?;
       cipher
         .encrypt_in_place_detached(nonce, &additional_data, ciphertext)
-        .map_err(|_| operation_error("Encryption failed"))?
+        .map_err(|_| EncryptError::Failed)?
     }
-    _ => return Err(type_error("invalid length")),
+    _ => return Err(EncryptError::InvalidLength),
   };
 
   Ok(tag)
@@ -223,7 +239,7 @@ fn encrypt_aes_gcm(
   iv: Vec<u8>,
   additional_data: Option<Vec<u8>>,
   data: &[u8],
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, EncryptError> {
   let key = key.as_secret_key()?;
   let additional_data = additional_data.unwrap_or_default();
 
@@ -244,7 +260,7 @@ fn encrypt_aes_gcm(
       &mut ciphertext,
       additional_data,
     )?,
-    _ => return Err(type_error("iv length not equal to 12 or 16")),
+    _ => return Err(EncryptError::InvalidIvLength),
   };
 
   // Truncated tag to the specified tag length.
@@ -261,7 +277,7 @@ fn encrypt_aes_ctr_gen<B>(
   key: &[u8],
   counter: &[u8],
   data: &[u8],
-) -> Result<Vec<u8>, AnyError>
+) -> Result<Vec<u8>, EncryptError>
 where
   B: KeyIvInit + StreamCipher,
 {
@@ -270,7 +286,7 @@ where
   let mut ciphertext = data.to_vec();
   cipher
     .try_apply_keystream(&mut ciphertext)
-    .map_err(|_| operation_error("tried to encrypt too much data"))?;
+    .map_err(|_| EncryptError::TooMuchData)?;
 
   Ok(ciphertext)
 }
@@ -281,7 +297,7 @@ fn encrypt_aes_ctr(
   counter: &[u8],
   ctr_length: usize,
   data: &[u8],
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, EncryptError> {
   let key = key.as_secret_key()?;
 
   match ctr_length {
@@ -289,22 +305,20 @@ fn encrypt_aes_ctr(
       128 => encrypt_aes_ctr_gen::<Ctr32BE<aes::Aes128>>(key, counter, data),
       192 => encrypt_aes_ctr_gen::<Ctr32BE<aes::Aes192>>(key, counter, data),
       256 => encrypt_aes_ctr_gen::<Ctr32BE<aes::Aes256>>(key, counter, data),
-      _ => Err(type_error("invalid length")),
+      _ => Err(EncryptError::InvalidLength),
     },
     64 => match key_length {
       128 => encrypt_aes_ctr_gen::<Ctr64BE<aes::Aes128>>(key, counter, data),
       192 => encrypt_aes_ctr_gen::<Ctr64BE<aes::Aes192>>(key, counter, data),
       256 => encrypt_aes_ctr_gen::<Ctr64BE<aes::Aes256>>(key, counter, data),
-      _ => Err(type_error("invalid length")),
+      _ => Err(EncryptError::InvalidLength),
     },
     128 => match key_length {
       128 => encrypt_aes_ctr_gen::<Ctr128BE<aes::Aes128>>(key, counter, data),
       192 => encrypt_aes_ctr_gen::<Ctr128BE<aes::Aes192>>(key, counter, data),
       256 => encrypt_aes_ctr_gen::<Ctr128BE<aes::Aes256>>(key, counter, data),
-      _ => Err(type_error("invalid length")),
+      _ => Err(EncryptError::InvalidLength),
     },
-    _ => Err(type_error(
-      "invalid counter length. Currently supported 32/64/128 bits",
-    )),
+    _ => Err(EncryptError::InvalidCounterLength),
   }
 }
diff --git a/ext/crypto/export_key.rs b/ext/crypto/export_key.rs
index 00ce7e11c6..edf0d7239c 100644
--- a/ext/crypto/export_key.rs
+++ b/ext/crypto/export_key.rs
@@ -4,8 +4,6 @@ use base64::prelude::BASE64_URL_SAFE_NO_PAD;
 use base64::Engine;
 use const_oid::AssociatedOid;
 use const_oid::ObjectIdentifier;
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::ToJsBuffer;
 use elliptic_curve::sec1::ToEncodedPoint;
@@ -22,6 +20,16 @@ use spki::AlgorithmIdentifierOwned;
 
 use crate::shared::*;
 
+#[derive(Debug, thiserror::Error)]
+pub enum ExportKeyError {
+  #[error(transparent)]
+  General(#[from] SharedError),
+  #[error(transparent)]
+  Der(#[from] spki::der::Error),
+  #[error("Unsupported named curve")]
+  UnsupportedNamedCurve,
+}
+
 #[derive(Deserialize)]
 #[serde(rename_all = "camelCase")]
 pub struct ExportKeyOptions {
@@ -99,7 +107,7 @@ pub enum ExportKeyResult {
 pub fn op_crypto_export_key(
   #[serde] opts: ExportKeyOptions,
   #[serde] key_data: V8RawKeyData,
-) -> Result<ExportKeyResult, AnyError> {
+) -> Result<ExportKeyResult, ExportKeyError> {
   match opts.algorithm {
     ExportKeyAlgorithm::RsassaPkcs1v15 {}
     | ExportKeyAlgorithm::RsaPss {}
@@ -125,7 +133,7 @@ fn bytes_to_b64(bytes: &[u8]) -> String {
 fn export_key_rsa(
   format: ExportKeyFormat,
   key_data: V8RawKeyData,
-) -> Result<ExportKeyResult, deno_core::anyhow::Error> {
+) -> Result<ExportKeyResult, ExportKeyError> {
   match format {
     ExportKeyFormat::Spki => {
       let subject_public_key = &key_data.as_rsa_public_key()?;
@@ -181,12 +189,7 @@ fn export_key_rsa(
     ExportKeyFormat::JwkPublic => {
       let public_key = key_data.as_rsa_public_key()?;
       let public_key = rsa::pkcs1::RsaPublicKey::from_der(&public_key)
-        .map_err(|_| {
-          custom_error(
-            "DOMExceptionOperationError",
-            "failed to decode public key",
-          )
-        })?;
+        .map_err(|_| SharedError::FailedDecodePublicKey)?;
 
       Ok(ExportKeyResult::JwkPublicRsa {
         n: uint_to_b64(public_key.modulus),
@@ -196,12 +199,7 @@ fn export_key_rsa(
     ExportKeyFormat::JwkPrivate => {
       let private_key = key_data.as_rsa_private_key()?;
       let private_key = rsa::pkcs1::RsaPrivateKey::from_der(private_key)
-        .map_err(|_| {
-          custom_error(
-            "DOMExceptionOperationError",
-            "failed to decode private key",
-          )
-        })?;
+        .map_err(|_| SharedError::FailedDecodePrivateKey)?;
 
       Ok(ExportKeyResult::JwkPrivateRsa {
         n: uint_to_b64(private_key.modulus),
@@ -214,14 +212,14 @@ fn export_key_rsa(
         qi: uint_to_b64(private_key.coefficient),
       })
     }
-    _ => Err(unsupported_format()),
+    _ => Err(SharedError::UnsupportedFormat.into()),
   }
 }
 
 fn export_key_symmetric(
   format: ExportKeyFormat,
   key_data: V8RawKeyData,
-) -> Result<ExportKeyResult, deno_core::anyhow::Error> {
+) -> Result<ExportKeyResult, ExportKeyError> {
   match format {
     ExportKeyFormat::JwkSecret => {
       let bytes = key_data.as_secret_key()?;
@@ -230,7 +228,7 @@ fn export_key_symmetric(
         k: bytes_to_b64(bytes),
       })
     }
-    _ => Err(unsupported_format()),
+    _ => Err(SharedError::UnsupportedFormat.into()),
   }
 }
 
@@ -239,7 +237,7 @@ fn export_key_ec(
   key_data: V8RawKeyData,
   algorithm: ExportKeyAlgorithm,
   named_curve: EcNamedCurve,
-) -> Result<ExportKeyResult, deno_core::anyhow::Error> {
+) -> Result<ExportKeyResult, ExportKeyError> {
   match format {
     ExportKeyFormat::Raw => {
       let subject_public_key = match named_curve {
@@ -332,10 +330,7 @@ fn export_key_ec(
             y: bytes_to_b64(y),
           })
         } else {
-          Err(custom_error(
-            "DOMExceptionOperationError",
-            "failed to decode public key",
-          ))
+          Err(SharedError::FailedDecodePublicKey.into())
         }
       }
       EcNamedCurve::P384 => {
@@ -350,10 +345,7 @@ fn export_key_ec(
             y: bytes_to_b64(y),
           })
         } else {
-          Err(custom_error(
-            "DOMExceptionOperationError",
-            "failed to decode public key",
-          ))
+          Err(SharedError::FailedDecodePublicKey.into())
         }
       }
       EcNamedCurve::P521 => {
@@ -368,10 +360,7 @@ fn export_key_ec(
             y: bytes_to_b64(y),
           })
         } else {
-          Err(custom_error(
-            "DOMExceptionOperationError",
-            "failed to decode public key",
-          ))
+          Err(SharedError::FailedDecodePublicKey.into())
         }
       }
     },
@@ -380,13 +369,8 @@ fn export_key_ec(
 
       match named_curve {
         EcNamedCurve::P256 => {
-          let ec_key =
-            p256::SecretKey::from_pkcs8_der(private_key).map_err(|_| {
-              custom_error(
-                "DOMExceptionOperationError",
-                "failed to decode private key",
-              )
-            })?;
+          let ec_key = p256::SecretKey::from_pkcs8_der(private_key)
+            .map_err(|_| SharedError::FailedDecodePrivateKey)?;
 
           let point = ec_key.public_key().to_encoded_point(false);
           if let elliptic_curve::sec1::Coordinates::Uncompressed { x, y } =
@@ -398,18 +382,13 @@ fn export_key_ec(
               d: bytes_to_b64(&ec_key.to_bytes()),
             })
           } else {
-            Err(data_error("expected valid public EC key"))
+            Err(SharedError::ExpectedValidPublicECKey.into())
           }
         }
 
         EcNamedCurve::P384 => {
-          let ec_key =
-            p384::SecretKey::from_pkcs8_der(private_key).map_err(|_| {
-              custom_error(
-                "DOMExceptionOperationError",
-                "failed to decode private key",
-              )
-            })?;
+          let ec_key = p384::SecretKey::from_pkcs8_der(private_key)
+            .map_err(|_| SharedError::FailedDecodePrivateKey)?;
 
           let point = ec_key.public_key().to_encoded_point(false);
           if let elliptic_curve::sec1::Coordinates::Uncompressed { x, y } =
@@ -421,12 +400,12 @@ fn export_key_ec(
               d: bytes_to_b64(&ec_key.to_bytes()),
             })
           } else {
-            Err(data_error("expected valid public EC key"))
+            Err(SharedError::ExpectedValidPublicECKey.into())
           }
         }
-        _ => Err(not_supported_error("Unsupported namedCurve")),
+        _ => Err(ExportKeyError::UnsupportedNamedCurve),
       }
     }
-    ExportKeyFormat::JwkSecret => Err(unsupported_format()),
+    ExportKeyFormat::JwkSecret => Err(SharedError::UnsupportedFormat.into()),
   }
 }
diff --git a/ext/crypto/generate_key.rs b/ext/crypto/generate_key.rs
index 43aea2c705..3c0bd77c22 100644
--- a/ext/crypto/generate_key.rs
+++ b/ext/crypto/generate_key.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::unsync::spawn_blocking;
 use deno_core::ToJsBuffer;
@@ -16,6 +15,26 @@ use serde::Deserialize;
 
 use crate::shared::*;
 
+#[derive(Debug, thiserror::Error)]
+pub enum GenerateKeyError {
+  #[error(transparent)]
+  General(#[from] SharedError),
+  #[error("Bad public exponent")]
+  BadPublicExponent,
+  #[error("Invalid HMAC key length")]
+  InvalidHMACKeyLength,
+  #[error("Failed to serialize RSA key")]
+  FailedRSAKeySerialization,
+  #[error("Invalid AES key length")]
+  InvalidAESKeyLength,
+  #[error("Failed to generate RSA key")]
+  FailedRSAKeyGeneration,
+  #[error("Failed to generate EC key")]
+  FailedECKeyGeneration,
+  #[error("Failed to generate key")]
+  FailedKeyGeneration,
+}
+
 // Allowlist for RSA public exponents.
 static PUB_EXPONENT_1: Lazy<BigUint> =
   Lazy::new(|| BigUint::from_u64(3).unwrap());
@@ -46,7 +65,7 @@ pub enum GenerateKeyOptions {
 #[serde]
 pub async fn op_crypto_generate_key(
   #[serde] opts: GenerateKeyOptions,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, GenerateKeyError> {
   let fun = || match opts {
     GenerateKeyOptions::Rsa {
       modulus_length,
@@ -65,21 +84,21 @@ pub async fn op_crypto_generate_key(
 fn generate_key_rsa(
   modulus_length: u32,
   public_exponent: &[u8],
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, GenerateKeyError> {
   let exponent = BigUint::from_bytes_be(public_exponent);
   if exponent != *PUB_EXPONENT_1 && exponent != *PUB_EXPONENT_2 {
-    return Err(operation_error("Bad public exponent"));
+    return Err(GenerateKeyError::BadPublicExponent);
   }
 
   let mut rng = OsRng;
 
   let private_key =
     RsaPrivateKey::new_with_exp(&mut rng, modulus_length as usize, &exponent)
-      .map_err(|_| operation_error("Failed to generate RSA key"))?;
+      .map_err(|_| GenerateKeyError::FailedRSAKeyGeneration)?;
 
   let private_key = private_key
     .to_pkcs1_der()
-    .map_err(|_| operation_error("Failed to serialize RSA key"))?;
+    .map_err(|_| GenerateKeyError::FailedRSAKeySerialization)?;
 
   Ok(private_key.as_bytes().to_vec())
 }
@@ -90,7 +109,9 @@ fn generate_key_ec_p521() -> Vec<u8> {
   key.to_nonzero_scalar().to_bytes().to_vec()
 }
 
-fn generate_key_ec(named_curve: EcNamedCurve) -> Result<Vec<u8>, AnyError> {
+fn generate_key_ec(
+  named_curve: EcNamedCurve,
+) -> Result<Vec<u8>, GenerateKeyError> {
   let curve = match named_curve {
     EcNamedCurve::P256 => &ring::signature::ECDSA_P256_SHA256_FIXED_SIGNING,
     EcNamedCurve::P384 => &ring::signature::ECDSA_P384_SHA384_FIXED_SIGNING,
@@ -100,21 +121,21 @@ fn generate_key_ec(named_curve: EcNamedCurve) -> Result<Vec<u8>, AnyError> {
   let rng = ring::rand::SystemRandom::new();
 
   let pkcs8 = EcdsaKeyPair::generate_pkcs8(curve, &rng)
-    .map_err(|_| operation_error("Failed to generate EC key"))?;
+    .map_err(|_| GenerateKeyError::FailedECKeyGeneration)?;
 
   Ok(pkcs8.as_ref().to_vec())
 }
 
-fn generate_key_aes(length: usize) -> Result<Vec<u8>, AnyError> {
+fn generate_key_aes(length: usize) -> Result<Vec<u8>, GenerateKeyError> {
   if length % 8 != 0 || length > 256 {
-    return Err(operation_error("Invalid AES key length"));
+    return Err(GenerateKeyError::InvalidAESKeyLength);
   }
 
   let mut key = vec![0u8; length / 8];
   let rng = ring::rand::SystemRandom::new();
   rng
     .fill(&mut key)
-    .map_err(|_| operation_error("Failed to generate key"))?;
+    .map_err(|_| GenerateKeyError::FailedKeyGeneration)?;
 
   Ok(key)
 }
@@ -122,7 +143,7 @@ fn generate_key_aes(length: usize) -> Result<Vec<u8>, AnyError> {
 fn generate_key_hmac(
   hash: ShaHash,
   length: Option<usize>,
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, GenerateKeyError> {
   let hash = match hash {
     ShaHash::Sha1 => &ring::hmac::HMAC_SHA1_FOR_LEGACY_USE_ONLY,
     ShaHash::Sha256 => &ring::hmac::HMAC_SHA256,
@@ -132,12 +153,12 @@ fn generate_key_hmac(
 
   let length = if let Some(length) = length {
     if length % 8 != 0 {
-      return Err(operation_error("Invalid HMAC key length"));
+      return Err(GenerateKeyError::InvalidHMACKeyLength);
     }
 
     let length = length / 8;
     if length > ring::digest::MAX_BLOCK_LEN {
-      return Err(operation_error("Invalid HMAC key length"));
+      return Err(GenerateKeyError::InvalidHMACKeyLength);
     }
 
     length
@@ -149,7 +170,7 @@ fn generate_key_hmac(
   let mut key = vec![0u8; length];
   rng
     .fill(&mut key)
-    .map_err(|_| operation_error("Failed to generate key"))?;
+    .map_err(|_| GenerateKeyError::FailedKeyGeneration)?;
 
   Ok(key)
 }
diff --git a/ext/crypto/import_key.rs b/ext/crypto/import_key.rs
index e30baea03a..3463ca2beb 100644
--- a/ext/crypto/import_key.rs
+++ b/ext/crypto/import_key.rs
@@ -1,7 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 use base64::Engine;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::JsBuffer;
 use deno_core::ToJsBuffer;
@@ -15,6 +14,70 @@ use spki::der::Decode;
 
 use crate::shared::*;
 
+#[derive(Debug, thiserror::Error)]
+pub enum ImportKeyError {
+  #[error(transparent)]
+  General(#[from] SharedError),
+  #[error("invalid modulus")]
+  InvalidModulus,
+  #[error("invalid public exponent")]
+  InvalidPublicExponent,
+  #[error("invalid private exponent")]
+  InvalidPrivateExponent,
+  #[error("invalid first prime factor")]
+  InvalidFirstPrimeFactor,
+  #[error("invalid second prime factor")]
+  InvalidSecondPrimeFactor,
+  #[error("invalid first CRT exponent")]
+  InvalidFirstCRTExponent,
+  #[error("invalid second CRT exponent")]
+  InvalidSecondCRTExponent,
+  #[error("invalid CRT coefficient")]
+  InvalidCRTCoefficient,
+  #[error("invalid b64 coordinate")]
+  InvalidB64Coordinate,
+  #[error("invalid RSA public key")]
+  InvalidRSAPublicKey,
+  #[error("invalid RSA private key")]
+  InvalidRSAPrivateKey,
+  #[error("unsupported algorithm")]
+  UnsupportedAlgorithm,
+  #[error("public key is invalid (too long)")]
+  PublicKeyTooLong,
+  #[error("private key is invalid (too long)")]
+  PrivateKeyTooLong,
+  #[error("invalid P-256 elliptic curve point")]
+  InvalidP256ECPoint,
+  #[error("invalid P-384 elliptic curve point")]
+  InvalidP384ECPoint,
+  #[error("invalid P-521 elliptic curve point")]
+  InvalidP521ECPoint,
+  #[error("invalid P-256 elliptic curve SPKI data")]
+  InvalidP256ECSPKIData,
+  #[error("invalid P-384 elliptic curve SPKI data")]
+  InvalidP384ECSPKIData,
+  #[error("invalid P-521 elliptic curve SPKI data")]
+  InvalidP521ECSPKIData,
+  #[error("curve mismatch")]
+  CurveMismatch,
+  #[error("Unsupported named curve")]
+  UnsupportedNamedCurve,
+  #[error("invalid key data")]
+  InvalidKeyData,
+  #[error("invalid JWK private key")]
+  InvalidJWKPrivateKey,
+  #[error(transparent)]
+  EllipticCurve(#[from] elliptic_curve::Error),
+  #[error("expected valid PKCS#8 data")]
+  ExpectedValidPkcs8Data,
+  #[error("malformed parameters")]
+  MalformedParameters,
+  #[error(transparent)]
+  Spki(#[from] spki::Error),
+  #[error(transparent)]
+  Der(#[from] rsa::pkcs1::der::Error),
+}
+
 #[derive(Deserialize)]
 #[serde(rename_all = "camelCase")]
 pub enum KeyData {
@@ -93,7 +156,7 @@ pub enum ImportKeyResult {
 pub fn op_crypto_import_key(
   #[serde] opts: ImportKeyOptions,
   #[serde] key_data: KeyData,
-) -> Result<ImportKeyResult, AnyError> {
+) -> Result<ImportKeyResult, ImportKeyError> {
   match opts {
     ImportKeyOptions::RsassaPkcs1v15 {} => import_key_rsassa(key_data),
     ImportKeyOptions::RsaPss {} => import_key_rsapss(key_data),
@@ -117,21 +180,21 @@ const BASE64_URL_SAFE_FORGIVING:
   );
 
 macro_rules! jwt_b64_int_or_err {
-  ($name:ident, $b64:expr, $err:expr) => {
+  ($name:ident, $b64:expr, $err:tt) => {
     let bytes = BASE64_URL_SAFE_FORGIVING
       .decode($b64)
-      .map_err(|_| data_error($err))?;
-    let $name = UintRef::new(&bytes).map_err(|_| data_error($err))?;
+      .map_err(|_| ImportKeyError::$err)?;
+    let $name = UintRef::new(&bytes).map_err(|_| ImportKeyError::$err)?;
   };
 }
 
 fn import_key_rsa_jwk(
   key_data: KeyData,
-) -> Result<ImportKeyResult, deno_core::anyhow::Error> {
+) -> Result<ImportKeyResult, ImportKeyError> {
   match key_data {
     KeyData::JwkPublicRsa { n, e } => {
-      jwt_b64_int_or_err!(modulus, &n, "invalid modulus");
-      jwt_b64_int_or_err!(public_exponent, &e, "invalid public exponent");
+      jwt_b64_int_or_err!(modulus, &n, InvalidModulus);
+      jwt_b64_int_or_err!(public_exponent, &e, InvalidPublicExponent);
 
       let public_key = rsa::pkcs1::RsaPublicKey {
         modulus,
@@ -141,7 +204,7 @@ fn import_key_rsa_jwk(
       let mut data = Vec::new();
       public_key
         .encode_to_vec(&mut data)
-        .map_err(|_| data_error("invalid rsa public key"))?;
+        .map_err(|_| ImportKeyError::InvalidRSAPublicKey)?;
 
       let public_exponent =
         public_key.public_exponent.as_bytes().to_vec().into();
@@ -163,14 +226,14 @@ fn import_key_rsa_jwk(
       dq,
       qi,
     } => {
-      jwt_b64_int_or_err!(modulus, &n, "invalid modulus");
-      jwt_b64_int_or_err!(public_exponent, &e, "invalid public exponent");
-      jwt_b64_int_or_err!(private_exponent, &d, "invalid private exponent");
-      jwt_b64_int_or_err!(prime1, &p, "invalid first prime factor");
-      jwt_b64_int_or_err!(prime2, &q, "invalid second prime factor");
-      jwt_b64_int_or_err!(exponent1, &dp, "invalid first CRT exponent");
-      jwt_b64_int_or_err!(exponent2, &dq, "invalid second CRT exponent");
-      jwt_b64_int_or_err!(coefficient, &qi, "invalid CRT coefficient");
+      jwt_b64_int_or_err!(modulus, &n, InvalidModulus);
+      jwt_b64_int_or_err!(public_exponent, &e, InvalidPublicExponent);
+      jwt_b64_int_or_err!(private_exponent, &d, InvalidPrivateExponent);
+      jwt_b64_int_or_err!(prime1, &p, InvalidFirstPrimeFactor);
+      jwt_b64_int_or_err!(prime2, &q, InvalidSecondPrimeFactor);
+      jwt_b64_int_or_err!(exponent1, &dp, InvalidFirstCRTExponent);
+      jwt_b64_int_or_err!(exponent2, &dq, InvalidSecondCRTExponent);
+      jwt_b64_int_or_err!(coefficient, &qi, InvalidCRTCoefficient);
 
       let private_key = rsa::pkcs1::RsaPrivateKey {
         modulus,
@@ -187,7 +250,7 @@ fn import_key_rsa_jwk(
       let mut data = Vec::new();
       private_key
         .encode_to_vec(&mut data)
-        .map_err(|_| data_error("invalid rsa private key"))?;
+        .map_err(|_| ImportKeyError::InvalidRSAPrivateKey)?;
 
       let public_exponent =
         private_key.public_exponent.as_bytes().to_vec().into();
@@ -205,37 +268,33 @@ fn import_key_rsa_jwk(
 
 fn import_key_rsassa(
   key_data: KeyData,
-) -> Result<ImportKeyResult, deno_core::anyhow::Error> {
+) -> Result<ImportKeyResult, ImportKeyError> {
   match key_data {
     KeyData::Spki(data) => {
       // 2-3.
-      let pk_info = spki::SubjectPublicKeyInfoRef::try_from(&*data)
-        .map_err(|e| data_error(e.to_string()))?;
+      let pk_info = spki::SubjectPublicKeyInfoRef::try_from(&*data)?;
 
       // 4-5.
       let alg = pk_info.algorithm.oid;
 
       // 6-7. (skipped, only support rsaEncryption for interoperability)
       if alg != RSA_ENCRYPTION_OID {
-        return Err(data_error("unsupported algorithm"));
+        return Err(ImportKeyError::UnsupportedAlgorithm);
       }
 
       // 8-9.
       let public_key = rsa::pkcs1::RsaPublicKey::from_der(
         pk_info.subject_public_key.raw_bytes(),
-      )
-      .map_err(|e| data_error(e.to_string()))?;
+      )?;
 
-      let bytes_consumed = public_key
-        .encoded_len()
-        .map_err(|e| data_error(e.to_string()))?;
+      let bytes_consumed = public_key.encoded_len()?;
 
       if bytes_consumed
         != rsa::pkcs1::der::Length::new(
           pk_info.subject_public_key.raw_bytes().len() as u16,
         )
       {
-        return Err(data_error("public key is invalid (too long)"));
+        return Err(ImportKeyError::PublicKeyTooLong);
       }
 
       let data = pk_info.subject_public_key.raw_bytes().to_vec().into();
@@ -251,30 +310,26 @@ fn import_key_rsassa(
     }
     KeyData::Pkcs8(data) => {
       // 2-3.
-      let pk_info = PrivateKeyInfo::from_der(&data)
-        .map_err(|e| data_error(e.to_string()))?;
+      let pk_info = PrivateKeyInfo::from_der(&data)?;
 
       // 4-5.
       let alg = pk_info.algorithm.oid;
 
       // 6-7. (skipped, only support rsaEncryption for interoperability)
       if alg != RSA_ENCRYPTION_OID {
-        return Err(data_error("unsupported algorithm"));
+        return Err(ImportKeyError::UnsupportedAlgorithm);
       }
 
       // 8-9.
       let private_key =
-        rsa::pkcs1::RsaPrivateKey::from_der(pk_info.private_key)
-          .map_err(|e| data_error(e.to_string()))?;
+        rsa::pkcs1::RsaPrivateKey::from_der(pk_info.private_key)?;
 
-      let bytes_consumed = private_key
-        .encoded_len()
-        .map_err(|e| data_error(e.to_string()))?;
+      let bytes_consumed = private_key.encoded_len()?;
 
       if bytes_consumed
         != rsa::pkcs1::der::Length::new(pk_info.private_key.len() as u16)
       {
-        return Err(data_error("private key is invalid (too long)"));
+        return Err(ImportKeyError::PrivateKeyTooLong);
       }
 
       let data = pk_info.private_key.to_vec().into();
@@ -291,43 +346,39 @@ fn import_key_rsassa(
     KeyData::JwkPublicRsa { .. } | KeyData::JwkPrivateRsa { .. } => {
       import_key_rsa_jwk(key_data)
     }
-    _ => Err(unsupported_format()),
+    _ => Err(SharedError::UnsupportedFormat.into()),
   }
 }
 
 fn import_key_rsapss(
   key_data: KeyData,
-) -> Result<ImportKeyResult, deno_core::anyhow::Error> {
+) -> Result<ImportKeyResult, ImportKeyError> {
   match key_data {
     KeyData::Spki(data) => {
       // 2-3.
-      let pk_info = spki::SubjectPublicKeyInfoRef::try_from(&*data)
-        .map_err(|e| data_error(e.to_string()))?;
+      let pk_info = spki::SubjectPublicKeyInfoRef::try_from(&*data)?;
 
       // 4-5.
       let alg = pk_info.algorithm.oid;
 
       // 6-7. (skipped, only support rsaEncryption for interoperability)
       if alg != RSA_ENCRYPTION_OID {
-        return Err(data_error("unsupported algorithm"));
+        return Err(ImportKeyError::UnsupportedAlgorithm);
       }
 
       // 8-9.
       let public_key = rsa::pkcs1::RsaPublicKey::from_der(
         pk_info.subject_public_key.raw_bytes(),
-      )
-      .map_err(|e| data_error(e.to_string()))?;
+      )?;
 
-      let bytes_consumed = public_key
-        .encoded_len()
-        .map_err(|e| data_error(e.to_string()))?;
+      let bytes_consumed = public_key.encoded_len()?;
 
       if bytes_consumed
         != rsa::pkcs1::der::Length::new(
           pk_info.subject_public_key.raw_bytes().len() as u16,
         )
       {
-        return Err(data_error("public key is invalid (too long)"));
+        return Err(ImportKeyError::PublicKeyTooLong);
       }
 
       let data = pk_info.subject_public_key.raw_bytes().to_vec().into();
@@ -343,30 +394,26 @@ fn import_key_rsapss(
     }
     KeyData::Pkcs8(data) => {
       // 2-3.
-      let pk_info = PrivateKeyInfo::from_der(&data)
-        .map_err(|e| data_error(e.to_string()))?;
+      let pk_info = PrivateKeyInfo::from_der(&data)?;
 
       // 4-5.
       let alg = pk_info.algorithm.oid;
 
       // 6-7. (skipped, only support rsaEncryption for interoperability)
       if alg != RSA_ENCRYPTION_OID {
-        return Err(data_error("unsupported algorithm"));
+        return Err(ImportKeyError::UnsupportedAlgorithm);
       }
 
       // 8-9.
       let private_key =
-        rsa::pkcs1::RsaPrivateKey::from_der(pk_info.private_key)
-          .map_err(|e| data_error(e.to_string()))?;
+        rsa::pkcs1::RsaPrivateKey::from_der(pk_info.private_key)?;
 
-      let bytes_consumed = private_key
-        .encoded_len()
-        .map_err(|e| data_error(e.to_string()))?;
+      let bytes_consumed = private_key.encoded_len()?;
 
       if bytes_consumed
         != rsa::pkcs1::der::Length::new(pk_info.private_key.len() as u16)
       {
-        return Err(data_error("private key is invalid (too long)"));
+        return Err(ImportKeyError::PrivateKeyTooLong);
       }
 
       let data = pk_info.private_key.to_vec().into();
@@ -383,43 +430,39 @@ fn import_key_rsapss(
     KeyData::JwkPublicRsa { .. } | KeyData::JwkPrivateRsa { .. } => {
       import_key_rsa_jwk(key_data)
     }
-    _ => Err(unsupported_format()),
+    _ => Err(SharedError::UnsupportedFormat.into()),
   }
 }
 
 fn import_key_rsaoaep(
   key_data: KeyData,
-) -> Result<ImportKeyResult, deno_core::anyhow::Error> {
+) -> Result<ImportKeyResult, ImportKeyError> {
   match key_data {
     KeyData::Spki(data) => {
       // 2-3.
-      let pk_info = spki::SubjectPublicKeyInfoRef::try_from(&*data)
-        .map_err(|e| data_error(e.to_string()))?;
+      let pk_info = spki::SubjectPublicKeyInfoRef::try_from(&*data)?;
 
       // 4-5.
       let alg = pk_info.algorithm.oid;
 
       // 6-7. (skipped, only support rsaEncryption for interoperability)
       if alg != RSA_ENCRYPTION_OID {
-        return Err(data_error("unsupported algorithm"));
+        return Err(ImportKeyError::UnsupportedAlgorithm);
       }
 
       // 8-9.
       let public_key = rsa::pkcs1::RsaPublicKey::from_der(
         pk_info.subject_public_key.raw_bytes(),
-      )
-      .map_err(|e| data_error(e.to_string()))?;
+      )?;
 
-      let bytes_consumed = public_key
-        .encoded_len()
-        .map_err(|e| data_error(e.to_string()))?;
+      let bytes_consumed = public_key.encoded_len()?;
 
       if bytes_consumed
         != rsa::pkcs1::der::Length::new(
           pk_info.subject_public_key.raw_bytes().len() as u16,
         )
       {
-        return Err(data_error("public key is invalid (too long)"));
+        return Err(ImportKeyError::PublicKeyTooLong);
       }
 
       let data = pk_info.subject_public_key.raw_bytes().to_vec().into();
@@ -435,30 +478,26 @@ fn import_key_rsaoaep(
     }
     KeyData::Pkcs8(data) => {
       // 2-3.
-      let pk_info = PrivateKeyInfo::from_der(&data)
-        .map_err(|e| data_error(e.to_string()))?;
+      let pk_info = PrivateKeyInfo::from_der(&data)?;
 
       // 4-5.
       let alg = pk_info.algorithm.oid;
 
       // 6-7. (skipped, only support rsaEncryption for interoperability)
       if alg != RSA_ENCRYPTION_OID {
-        return Err(data_error("unsupported algorithm"));
+        return Err(ImportKeyError::UnsupportedAlgorithm);
       }
 
       // 8-9.
       let private_key =
-        rsa::pkcs1::RsaPrivateKey::from_der(pk_info.private_key)
-          .map_err(|e| data_error(e.to_string()))?;
+        rsa::pkcs1::RsaPrivateKey::from_der(pk_info.private_key)?;
 
-      let bytes_consumed = private_key
-        .encoded_len()
-        .map_err(|e| data_error(e.to_string()))?;
+      let bytes_consumed = private_key.encoded_len()?;
 
       if bytes_consumed
         != rsa::pkcs1::der::Length::new(pk_info.private_key.len() as u16)
       {
-        return Err(data_error("private key is invalid (too long)"));
+        return Err(ImportKeyError::PrivateKeyTooLong);
       }
 
       let data = pk_info.private_key.to_vec().into();
@@ -475,14 +514,14 @@ fn import_key_rsaoaep(
     KeyData::JwkPublicRsa { .. } | KeyData::JwkPrivateRsa { .. } => {
       import_key_rsa_jwk(key_data)
     }
-    _ => Err(unsupported_format()),
+    _ => Err(SharedError::UnsupportedFormat.into()),
   }
 }
 
 fn decode_b64url_to_field_bytes<C: elliptic_curve::Curve>(
   b64: &str,
-) -> Result<elliptic_curve::FieldBytes<C>, deno_core::anyhow::Error> {
-  jwt_b64_int_or_err!(val, b64, "invalid b64 coordinate");
+) -> Result<elliptic_curve::FieldBytes<C>, ImportKeyError> {
+  jwt_b64_int_or_err!(val, b64, InvalidB64Coordinate);
 
   let mut bytes = elliptic_curve::FieldBytes::<C>::default();
   let original_bytes = val.as_bytes();
@@ -495,7 +534,7 @@ fn decode_b64url_to_field_bytes<C: elliptic_curve::Curve>(
   let val = new_bytes.as_slice();
 
   if val.len() != bytes.len() {
-    return Err(data_error("invalid b64 coordinate"));
+    return Err(ImportKeyError::InvalidB64Coordinate);
   }
   bytes.copy_from_slice(val);
 
@@ -506,7 +545,7 @@ fn import_key_ec_jwk_to_point(
   x: String,
   y: String,
   named_curve: EcNamedCurve,
-) -> Result<Vec<u8>, deno_core::anyhow::Error> {
+) -> Result<Vec<u8>, ImportKeyError> {
   let point_bytes = match named_curve {
     EcNamedCurve::P256 => {
       let x = decode_b64url_to_field_bytes::<p256::NistP256>(&x)?;
@@ -534,7 +573,7 @@ fn import_key_ec_jwk_to_point(
 fn import_key_ec_jwk(
   key_data: KeyData,
   named_curve: EcNamedCurve,
-) -> Result<ImportKeyResult, deno_core::anyhow::Error> {
+) -> Result<ImportKeyResult, ImportKeyError> {
   match key_data {
     KeyData::JwkPublicEc { x, y } => {
       let point_bytes = import_key_ec_jwk_to_point(x, y, named_curve)?;
@@ -550,21 +589,21 @@ fn import_key_ec_jwk(
           let pk = p256::SecretKey::from_bytes(&d)?;
 
           pk.to_pkcs8_der()
-            .map_err(|_| data_error("invalid JWK private key"))?
+            .map_err(|_| ImportKeyError::InvalidJWKPrivateKey)?
         }
         EcNamedCurve::P384 => {
           let d = decode_b64url_to_field_bytes::<p384::NistP384>(&d)?;
           let pk = p384::SecretKey::from_bytes(&d)?;
 
           pk.to_pkcs8_der()
-            .map_err(|_| data_error("invalid JWK private key"))?
+            .map_err(|_| ImportKeyError::InvalidJWKPrivateKey)?
         }
         EcNamedCurve::P521 => {
           let d = decode_b64url_to_field_bytes::<p521::NistP521>(&d)?;
           let pk = p521::SecretKey::from_bytes(&d)?;
 
           pk.to_pkcs8_der()
-            .map_err(|_| data_error("invalid JWK private key"))?
+            .map_err(|_| ImportKeyError::InvalidJWKPrivateKey)?
         }
       };
 
@@ -595,7 +634,7 @@ impl<'a> TryFrom<spki::der::asn1::AnyRef<'a>> for ECParametersSpki {
 fn import_key_ec(
   key_data: KeyData,
   named_curve: EcNamedCurve,
-) -> Result<ImportKeyResult, AnyError> {
+) -> Result<ImportKeyResult, ImportKeyError> {
   match key_data {
     KeyData::Raw(data) => {
       // The point is parsed and validated, ultimately the original data is
@@ -604,28 +643,28 @@ fn import_key_ec(
         EcNamedCurve::P256 => {
           // 1-2.
           let point = p256::EncodedPoint::from_bytes(&data)
-            .map_err(|_| data_error("invalid P-256 elliptic curve point"))?;
+            .map_err(|_| ImportKeyError::InvalidP256ECPoint)?;
           // 3.
           if point.is_identity() {
-            return Err(data_error("invalid P-256 elliptic curve point"));
+            return Err(ImportKeyError::InvalidP256ECPoint);
           }
         }
         EcNamedCurve::P384 => {
           // 1-2.
           let point = p384::EncodedPoint::from_bytes(&data)
-            .map_err(|_| data_error("invalid P-384 elliptic curve point"))?;
+            .map_err(|_| ImportKeyError::InvalidP384ECPoint)?;
           // 3.
           if point.is_identity() {
-            return Err(data_error("invalid P-384 elliptic curve point"));
+            return Err(ImportKeyError::InvalidP384ECPoint);
           }
         }
         EcNamedCurve::P521 => {
           // 1-2.
           let point = p521::EncodedPoint::from_bytes(&data)
-            .map_err(|_| data_error("invalid P-521 elliptic curve point"))?;
+            .map_err(|_| ImportKeyError::InvalidP521ECPoint)?;
           // 3.
           if point.is_identity() {
-            return Err(data_error("invalid P-521 elliptic curve point"));
+            return Err(ImportKeyError::InvalidP521ECPoint);
           }
         }
       };
@@ -635,11 +674,11 @@ fn import_key_ec(
     }
     KeyData::Pkcs8(data) => {
       let pk = PrivateKeyInfo::from_der(data.as_ref())
-        .map_err(|_| data_error("expected valid PKCS#8 data"))?;
+        .map_err(|_| ImportKeyError::ExpectedValidPkcs8Data)?;
       let named_curve_alg = pk
         .algorithm
         .parameters
-        .ok_or_else(|| data_error("malformed parameters"))?
+        .ok_or(ImportKeyError::MalformedParameters)?
         .try_into()
         .unwrap();
 
@@ -654,7 +693,7 @@ fn import_key_ec(
       };
 
       if pk_named_curve != Some(named_curve) {
-        return Err(data_error("curve mismatch"));
+        return Err(ImportKeyError::CurveMismatch);
       }
 
       Ok(ImportKeyResult::Ec {
@@ -663,14 +702,13 @@ fn import_key_ec(
     }
     KeyData::Spki(data) => {
       // 2-3.
-      let pk_info = spki::SubjectPublicKeyInfoRef::try_from(&*data)
-        .map_err(|e| data_error(e.to_string()))?;
+      let pk_info = spki::SubjectPublicKeyInfoRef::try_from(&*data)?;
 
       // 4.
       let alg = pk_info.algorithm.oid;
       // id-ecPublicKey
       if alg != elliptic_curve::ALGORITHM_OID {
-        return Err(data_error("unsupported algorithm"));
+        return Err(ImportKeyError::UnsupportedAlgorithm);
       }
 
       // 5-7.
@@ -678,9 +716,9 @@ fn import_key_ec(
         pk_info
           .algorithm
           .parameters
-          .ok_or_else(|| data_error("malformed parameters"))?,
+          .ok_or(ImportKeyError::MalformedParameters)?,
       )
-      .map_err(|_| data_error("malformed parameters"))?;
+      .map_err(|_| ImportKeyError::MalformedParameters)?;
 
       // 8-9.
       let named_curve_alg = params.named_curve_alg;
@@ -704,36 +742,30 @@ fn import_key_ec(
 
         let bytes_consumed = match named_curve {
           EcNamedCurve::P256 => {
-            let point =
-              p256::EncodedPoint::from_bytes(&*encoded_key).map_err(|_| {
-                data_error("invalid P-256 elliptic curve SPKI data")
-              })?;
+            let point = p256::EncodedPoint::from_bytes(&*encoded_key)
+              .map_err(|_| ImportKeyError::InvalidP256ECSPKIData)?;
             if point.is_identity() {
-              return Err(data_error("invalid P-256 elliptic curve point"));
+              return Err(ImportKeyError::InvalidP256ECPoint);
             }
 
             point.as_bytes().len()
           }
           EcNamedCurve::P384 => {
-            let point =
-              p384::EncodedPoint::from_bytes(&*encoded_key).map_err(|_| {
-                data_error("invalid P-384 elliptic curve SPKI data")
-              })?;
+            let point = p384::EncodedPoint::from_bytes(&*encoded_key)
+              .map_err(|_| ImportKeyError::InvalidP384ECSPKIData)?;
 
             if point.is_identity() {
-              return Err(data_error("invalid P-384 elliptic curve point"));
+              return Err(ImportKeyError::InvalidP384ECPoint);
             }
 
             point.as_bytes().len()
           }
           EcNamedCurve::P521 => {
-            let point =
-              p521::EncodedPoint::from_bytes(&*encoded_key).map_err(|_| {
-                data_error("invalid P-521 elliptic curve SPKI data")
-              })?;
+            let point = p521::EncodedPoint::from_bytes(&*encoded_key)
+              .map_err(|_| ImportKeyError::InvalidP521ECSPKIData)?;
 
             if point.is_identity() {
-              return Err(data_error("invalid P-521 elliptic curve point"));
+              return Err(ImportKeyError::InvalidP521ECPoint);
             }
 
             point.as_bytes().len()
@@ -741,15 +773,15 @@ fn import_key_ec(
         };
 
         if bytes_consumed != pk_info.subject_public_key.raw_bytes().len() {
-          return Err(data_error("public key is invalid (too long)"));
+          return Err(ImportKeyError::PublicKeyTooLong);
         }
 
         // 11.
         if named_curve != pk_named_curve {
-          return Err(data_error("curve mismatch"));
+          return Err(ImportKeyError::CurveMismatch);
         }
       } else {
-        return Err(data_error("Unsupported named curve"));
+        return Err(ImportKeyError::UnsupportedNamedCurve);
       }
 
       Ok(ImportKeyResult::Ec {
@@ -759,34 +791,38 @@ fn import_key_ec(
     KeyData::JwkPublicEc { .. } | KeyData::JwkPrivateEc { .. } => {
       import_key_ec_jwk(key_data, named_curve)
     }
-    _ => Err(unsupported_format()),
+    _ => Err(SharedError::UnsupportedFormat.into()),
   }
 }
 
-fn import_key_aes(key_data: KeyData) -> Result<ImportKeyResult, AnyError> {
+fn import_key_aes(
+  key_data: KeyData,
+) -> Result<ImportKeyResult, ImportKeyError> {
   Ok(match key_data {
     KeyData::JwkSecret { k } => {
       let data = BASE64_URL_SAFE_FORGIVING
         .decode(k)
-        .map_err(|_| data_error("invalid key data"))?;
+        .map_err(|_| ImportKeyError::InvalidKeyData)?;
       ImportKeyResult::Hmac {
         raw_data: RustRawKeyData::Secret(data.into()),
       }
     }
-    _ => return Err(unsupported_format()),
+    _ => return Err(SharedError::UnsupportedFormat.into()),
   })
 }
 
-fn import_key_hmac(key_data: KeyData) -> Result<ImportKeyResult, AnyError> {
+fn import_key_hmac(
+  key_data: KeyData,
+) -> Result<ImportKeyResult, ImportKeyError> {
   Ok(match key_data {
     KeyData::JwkSecret { k } => {
       let data = BASE64_URL_SAFE_FORGIVING
         .decode(k)
-        .map_err(|_| data_error("invalid key data"))?;
+        .map_err(|_| ImportKeyError::InvalidKeyData)?;
       ImportKeyResult::Hmac {
         raw_data: RustRawKeyData::Secret(data.into()),
       }
     }
-    _ => return Err(unsupported_format()),
+    _ => return Err(SharedError::UnsupportedFormat.into()),
   })
 }
diff --git a/ext/crypto/lib.rs b/ext/crypto/lib.rs
index 7aa3462c76..69dcd1413a 100644
--- a/ext/crypto/lib.rs
+++ b/ext/crypto/lib.rs
@@ -6,10 +6,7 @@ use aes_kw::KekAes256;
 
 use base64::prelude::BASE64_URL_SAFE_NO_PAD;
 use base64::Engine;
-use deno_core::error::custom_error;
 use deno_core::error::not_supported;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::ToJsBuffer;
 
@@ -17,7 +14,6 @@ use deno_core::unsync::spawn_blocking;
 use deno_core::JsBuffer;
 use deno_core::OpState;
 use serde::Deserialize;
-use shared::operation_error;
 
 use p256::elliptic_curve::sec1::FromEncodedPoint;
 use p256::pkcs8::DecodePrivateKey;
@@ -64,17 +60,27 @@ mod import_key;
 mod key;
 mod shared;
 mod x25519;
+mod x448;
 
 pub use crate::decrypt::op_crypto_decrypt;
+pub use crate::decrypt::DecryptError;
+pub use crate::ed25519::Ed25519Error;
 pub use crate::encrypt::op_crypto_encrypt;
+pub use crate::encrypt::EncryptError;
 pub use crate::export_key::op_crypto_export_key;
+pub use crate::export_key::ExportKeyError;
 pub use crate::generate_key::op_crypto_generate_key;
+pub use crate::generate_key::GenerateKeyError;
 pub use crate::import_key::op_crypto_import_key;
+pub use crate::import_key::ImportKeyError;
 use crate::key::Algorithm;
 use crate::key::CryptoHash;
 use crate::key::CryptoNamedCurve;
 use crate::key::HkdfOutput;
+pub use crate::shared::SharedError;
 use crate::shared::V8RawKeyData;
+pub use crate::x25519::X25519Error;
+pub use crate::x448::X448Error;
 
 deno_core::extension!(deno_crypto,
   deps = [ deno_webidl, deno_web ],
@@ -98,6 +104,14 @@ deno_core::extension!(deno_crypto,
     x25519::op_crypto_derive_bits_x25519,
     x25519::op_crypto_import_spki_x25519,
     x25519::op_crypto_import_pkcs8_x25519,
+    x25519::op_crypto_export_spki_x25519,
+    x25519::op_crypto_export_pkcs8_x25519,
+    x448::op_crypto_generate_x448_keypair,
+    x448::op_crypto_derive_bits_x448,
+    x448::op_crypto_import_spki_x448,
+    x448::op_crypto_import_pkcs8_x448,
+    x448::op_crypto_export_spki_x448,
+    x448::op_crypto_export_pkcs8_x448,
     ed25519::op_crypto_generate_ed25519_keypair,
     ed25519::op_crypto_import_spki_ed25519,
     ed25519::op_crypto_import_pkcs8_ed25519,
@@ -106,8 +120,6 @@ deno_core::extension!(deno_crypto,
     ed25519::op_crypto_export_spki_ed25519,
     ed25519::op_crypto_export_pkcs8_ed25519,
     ed25519::op_crypto_jwk_x_ed25519,
-    x25519::op_crypto_export_spki_x25519,
-    x25519::op_crypto_export_pkcs8_x25519,
   ],
   esm = [ "00_crypto.js" ],
   options = {
@@ -120,11 +132,63 @@ deno_core::extension!(deno_crypto,
   },
 );
 
+#[derive(Debug, thiserror::Error)]
+pub enum Error {
+  #[error(transparent)]
+  General(#[from] SharedError),
+  #[error(transparent)]
+  JoinError(#[from] tokio::task::JoinError),
+  #[error(transparent)]
+  Der(#[from] rsa::pkcs1::der::Error),
+  #[error("Missing argument hash")]
+  MissingArgumentHash,
+  #[error("Missing argument saltLength")]
+  MissingArgumentSaltLength,
+  #[error("unsupported algorithm")]
+  UnsupportedAlgorithm,
+  #[error(transparent)]
+  KeyRejected(#[from] ring::error::KeyRejected),
+  #[error(transparent)]
+  RSA(#[from] rsa::Error),
+  #[error(transparent)]
+  Pkcs1(#[from] rsa::pkcs1::Error),
+  #[error(transparent)]
+  Unspecified(#[from] ring::error::Unspecified),
+  #[error("Invalid key format")]
+  InvalidKeyFormat,
+  #[error(transparent)]
+  P256Ecdsa(#[from] p256::ecdsa::Error),
+  #[error("Unexpected error decoding private key")]
+  DecodePrivateKey,
+  #[error("Missing argument publicKey")]
+  MissingArgumentPublicKey,
+  #[error("Missing argument namedCurve")]
+  MissingArgumentNamedCurve,
+  #[error("Missing argument info")]
+  MissingArgumentInfo,
+  #[error("The length provided for HKDF is too large")]
+  HKDFLengthTooLarge,
+  #[error(transparent)]
+  Base64Decode(#[from] base64::DecodeError),
+  #[error("Data must be multiple of 8 bytes")]
+  DataInvalidSize,
+  #[error("Invalid key length")]
+  InvalidKeyLength,
+  #[error("encryption error")]
+  EncryptionError,
+  #[error("decryption error - integrity check failed")]
+  DecryptionError,
+  #[error("The ArrayBufferView's byte length ({0}) exceeds the number of bytes of entropy available via this API (65536)")]
+  ArrayBufferViewLengthExceeded(usize),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
 #[op2]
 #[serde]
 pub fn op_crypto_base64url_decode(
   #[string] data: String,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, Error> {
   let data: Vec<u8> = BASE64_URL_SAFE_NO_PAD.decode(data)?;
   Ok(data.into())
 }
@@ -140,12 +204,9 @@ pub fn op_crypto_base64url_encode(#[buffer] data: JsBuffer) -> String {
 pub fn op_crypto_get_random_values(
   state: &mut OpState,
   #[buffer] out: &mut [u8],
-) -> Result<(), AnyError> {
+) -> Result<(), Error> {
   if out.len() > 65536 {
-    return Err(
-      deno_web::DomExceptionQuotaExceededError::new(&format!("The ArrayBufferView's byte length ({}) exceeds the number of bytes of entropy available via this API (65536)", out.len()))
-        .into(),
-    );
+    return Err(Error::ArrayBufferViewLengthExceeded(out.len()));
   }
 
   let maybe_seeded_rng = state.try_borrow_mut::<StdRng>();
@@ -197,7 +258,7 @@ pub struct SignArg {
 pub async fn op_crypto_sign_key(
   #[serde] args: SignArg,
   #[buffer] zero_copy: JsBuffer,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, Error> {
   deno_core::unsync::spawn_blocking(move || {
     let data = &*zero_copy;
     let algorithm = args.algorithm;
@@ -206,10 +267,7 @@ pub async fn op_crypto_sign_key(
       Algorithm::RsassaPkcs1v15 => {
         use rsa::pkcs1v15::SigningKey;
         let private_key = RsaPrivateKey::from_pkcs1_der(&args.key.data)?;
-        match args
-          .hash
-          .ok_or_else(|| type_error("Missing argument hash".to_string()))?
-        {
+        match args.hash.ok_or_else(|| Error::MissingArgumentHash)? {
           CryptoHash::Sha1 => {
             let signing_key = SigningKey::<Sha1>::new(private_key);
             signing_key.sign(data)
@@ -232,15 +290,13 @@ pub async fn op_crypto_sign_key(
       Algorithm::RsaPss => {
         let private_key = RsaPrivateKey::from_pkcs1_der(&args.key.data)?;
 
-        let salt_len = args.salt_length.ok_or_else(|| {
-          type_error("Missing argument saltLength".to_string())
-        })? as usize;
+        let salt_len = args
+          .salt_length
+          .ok_or_else(|| Error::MissingArgumentSaltLength)?
+          as usize;
 
         let mut rng = OsRng;
-        match args
-          .hash
-          .ok_or_else(|| type_error("Missing argument hash".to_string()))?
-        {
+        match args.hash.ok_or_else(|| Error::MissingArgumentHash)? {
           CryptoHash::Sha1 => {
             let signing_key = Pss::new_with_salt::<Sha1>(salt_len);
             let hashed = Sha1::digest(data);
@@ -265,8 +321,10 @@ pub async fn op_crypto_sign_key(
         .to_vec()
       }
       Algorithm::Ecdsa => {
-        let curve: &EcdsaSigningAlgorithm =
-          args.named_curve.ok_or_else(not_supported)?.into();
+        let curve: &EcdsaSigningAlgorithm = args
+          .named_curve
+          .ok_or_else(|| Error::Other(not_supported()))?
+          .into();
 
         let rng = RingRand::SystemRandom::new();
         let key_pair = EcdsaKeyPair::from_pkcs8(curve, &args.key.data, &rng)?;
@@ -275,7 +333,7 @@ pub async fn op_crypto_sign_key(
         if let Some(hash) = args.hash {
           match hash {
             CryptoHash::Sha256 | CryptoHash::Sha384 => (),
-            _ => return Err(type_error("Unsupported algorithm")),
+            _ => return Err(Error::UnsupportedAlgorithm),
           }
         };
 
@@ -285,14 +343,17 @@ pub async fn op_crypto_sign_key(
         signature.as_ref().to_vec()
       }
       Algorithm::Hmac => {
-        let hash: HmacAlgorithm = args.hash.ok_or_else(not_supported)?.into();
+        let hash: HmacAlgorithm = args
+          .hash
+          .ok_or_else(|| Error::Other(not_supported()))?
+          .into();
 
         let key = HmacKey::new(hash, &args.key.data);
 
         let signature = ring::hmac::sign(&key, data);
         signature.as_ref().to_vec()
       }
-      _ => return Err(type_error("Unsupported algorithm".to_string())),
+      _ => return Err(Error::UnsupportedAlgorithm),
     };
 
     Ok(signature.into())
@@ -315,7 +376,7 @@ pub struct VerifyArg {
 pub async fn op_crypto_verify_key(
   #[serde] args: VerifyArg,
   #[buffer] zero_copy: JsBuffer,
-) -> Result<bool, AnyError> {
+) -> Result<bool, Error> {
   deno_core::unsync::spawn_blocking(move || {
     let data = &*zero_copy;
     let algorithm = args.algorithm;
@@ -326,10 +387,7 @@ pub async fn op_crypto_verify_key(
         use rsa::pkcs1v15::VerifyingKey;
         let public_key = read_rsa_public_key(args.key)?;
         let signature: Signature = args.signature.as_ref().try_into()?;
-        match args
-          .hash
-          .ok_or_else(|| type_error("Missing argument hash".to_string()))?
-        {
+        match args.hash.ok_or_else(|| Error::MissingArgumentHash)? {
           CryptoHash::Sha1 => {
             let verifying_key = VerifyingKey::<Sha1>::new(public_key);
             verifying_key.verify(data, &signature).is_ok()
@@ -352,14 +410,12 @@ pub async fn op_crypto_verify_key(
         let public_key = read_rsa_public_key(args.key)?;
         let signature = args.signature.as_ref();
 
-        let salt_len = args.salt_length.ok_or_else(|| {
-          type_error("Missing argument saltLength".to_string())
-        })? as usize;
+        let salt_len = args
+          .salt_length
+          .ok_or_else(|| Error::MissingArgumentSaltLength)?
+          as usize;
 
-        match args
-          .hash
-          .ok_or_else(|| type_error("Missing argument hash".to_string()))?
-        {
+        match args.hash.ok_or_else(|| Error::MissingArgumentHash)? {
           CryptoHash::Sha1 => {
             let pss = Pss::new_with_salt::<Sha1>(salt_len);
             let hashed = Sha1::digest(data);
@@ -383,15 +439,22 @@ pub async fn op_crypto_verify_key(
         }
       }
       Algorithm::Hmac => {
-        let hash: HmacAlgorithm = args.hash.ok_or_else(not_supported)?.into();
+        let hash: HmacAlgorithm = args
+          .hash
+          .ok_or_else(|| Error::Other(not_supported()))?
+          .into();
         let key = HmacKey::new(hash, &args.key.data);
         ring::hmac::verify(&key, data, &args.signature).is_ok()
       }
       Algorithm::Ecdsa => {
-        let signing_alg: &EcdsaSigningAlgorithm =
-          args.named_curve.ok_or_else(not_supported)?.into();
-        let verify_alg: &EcdsaVerificationAlgorithm =
-          args.named_curve.ok_or_else(not_supported)?.into();
+        let signing_alg: &EcdsaSigningAlgorithm = args
+          .named_curve
+          .ok_or_else(|| Error::Other(not_supported()))?
+          .into();
+        let verify_alg: &EcdsaVerificationAlgorithm = args
+          .named_curve
+          .ok_or_else(|| Error::Other(not_supported()))?
+          .into();
 
         let private_key;
 
@@ -404,7 +467,7 @@ pub async fn op_crypto_verify_key(
             private_key.public_key().as_ref()
           }
           KeyType::Public => &*args.key.data,
-          _ => return Err(type_error("Invalid Key format".to_string())),
+          _ => return Err(Error::InvalidKeyFormat),
         };
 
         let public_key =
@@ -412,7 +475,7 @@ pub async fn op_crypto_verify_key(
 
         public_key.verify(data, &args.signature).is_ok()
       }
-      _ => return Err(type_error("Unsupported algorithm".to_string())),
+      _ => return Err(Error::UnsupportedAlgorithm),
     };
 
     Ok(verification)
@@ -440,70 +503,68 @@ pub struct DeriveKeyArg {
 pub async fn op_crypto_derive_bits(
   #[serde] args: DeriveKeyArg,
   #[buffer] zero_copy: Option<JsBuffer>,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, Error> {
   deno_core::unsync::spawn_blocking(move || {
     let algorithm = args.algorithm;
     match algorithm {
       Algorithm::Pbkdf2 => {
-        let zero_copy = zero_copy.ok_or_else(not_supported)?;
+        let zero_copy =
+          zero_copy.ok_or_else(|| Error::Other(not_supported()))?;
         let salt = &*zero_copy;
         // The caller must validate these cases.
         assert!(args.length > 0);
         assert!(args.length % 8 == 0);
 
-        let algorithm = match args.hash.ok_or_else(not_supported)? {
-          CryptoHash::Sha1 => pbkdf2::PBKDF2_HMAC_SHA1,
-          CryptoHash::Sha256 => pbkdf2::PBKDF2_HMAC_SHA256,
-          CryptoHash::Sha384 => pbkdf2::PBKDF2_HMAC_SHA384,
-          CryptoHash::Sha512 => pbkdf2::PBKDF2_HMAC_SHA512,
-        };
+        let algorithm =
+          match args.hash.ok_or_else(|| Error::Other(not_supported()))? {
+            CryptoHash::Sha1 => pbkdf2::PBKDF2_HMAC_SHA1,
+            CryptoHash::Sha256 => pbkdf2::PBKDF2_HMAC_SHA256,
+            CryptoHash::Sha384 => pbkdf2::PBKDF2_HMAC_SHA384,
+            CryptoHash::Sha512 => pbkdf2::PBKDF2_HMAC_SHA512,
+          };
 
         // This will never panic. We have already checked length earlier.
-        let iterations =
-          NonZeroU32::new(args.iterations.ok_or_else(not_supported)?).unwrap();
+        let iterations = NonZeroU32::new(
+          args
+            .iterations
+            .ok_or_else(|| Error::Other(not_supported()))?,
+        )
+        .unwrap();
         let secret = args.key.data;
         let mut out = vec![0; args.length / 8];
         pbkdf2::derive(algorithm, iterations, salt, &secret, &mut out);
         Ok(out.into())
       }
       Algorithm::Ecdh => {
-        let named_curve = args.named_curve.ok_or_else(|| {
-          type_error("Missing argument namedCurve".to_string())
-        })?;
+        let named_curve = args
+          .named_curve
+          .ok_or_else(|| Error::MissingArgumentNamedCurve)?;
 
         let public_key = args
           .public_key
-          .ok_or_else(|| type_error("Missing argument publicKey"))?;
+          .ok_or_else(|| Error::MissingArgumentPublicKey)?;
 
         match named_curve {
           CryptoNamedCurve::P256 => {
             let secret_key = p256::SecretKey::from_pkcs8_der(&args.key.data)
-              .map_err(|_| {
-                type_error("Unexpected error decoding private key")
-              })?;
+              .map_err(|_| Error::DecodePrivateKey)?;
 
             let public_key = match public_key.r#type {
               KeyType::Private => {
                 p256::SecretKey::from_pkcs8_der(&public_key.data)
-                  .map_err(|_| {
-                    type_error("Unexpected error decoding private key")
-                  })?
+                  .map_err(|_| Error::DecodePrivateKey)?
                   .public_key()
               }
               KeyType::Public => {
                 let point = p256::EncodedPoint::from_bytes(public_key.data)
-                  .map_err(|_| {
-                    type_error("Unexpected error decoding private key")
-                  })?;
+                  .map_err(|_| Error::DecodePrivateKey)?;
 
                 let pk = p256::PublicKey::from_encoded_point(&point);
                 // pk is a constant time Option.
                 if pk.is_some().into() {
                   pk.unwrap()
                 } else {
-                  return Err(type_error(
-                    "Unexpected error decoding private key",
-                  ));
+                  return Err(Error::DecodePrivateKey);
                 }
               }
               _ => unreachable!(),
@@ -519,32 +580,24 @@ pub async fn op_crypto_derive_bits(
           }
           CryptoNamedCurve::P384 => {
             let secret_key = p384::SecretKey::from_pkcs8_der(&args.key.data)
-              .map_err(|_| {
-                type_error("Unexpected error decoding private key")
-              })?;
+              .map_err(|_| Error::DecodePrivateKey)?;
 
             let public_key = match public_key.r#type {
               KeyType::Private => {
                 p384::SecretKey::from_pkcs8_der(&public_key.data)
-                  .map_err(|_| {
-                    type_error("Unexpected error decoding private key")
-                  })?
+                  .map_err(|_| Error::DecodePrivateKey)?
                   .public_key()
               }
               KeyType::Public => {
                 let point = p384::EncodedPoint::from_bytes(public_key.data)
-                  .map_err(|_| {
-                    type_error("Unexpected error decoding private key")
-                  })?;
+                  .map_err(|_| Error::DecodePrivateKey)?;
 
                 let pk = p384::PublicKey::from_encoded_point(&point);
                 // pk is a constant time Option.
                 if pk.is_some().into() {
                   pk.unwrap()
                 } else {
-                  return Err(type_error(
-                    "Unexpected error decoding private key",
-                  ));
+                  return Err(Error::DecodePrivateKey);
                 }
               }
               _ => unreachable!(),
@@ -561,18 +614,18 @@ pub async fn op_crypto_derive_bits(
         }
       }
       Algorithm::Hkdf => {
-        let zero_copy = zero_copy.ok_or_else(not_supported)?;
+        let zero_copy =
+          zero_copy.ok_or_else(|| Error::Other(not_supported()))?;
         let salt = &*zero_copy;
-        let algorithm = match args.hash.ok_or_else(not_supported)? {
-          CryptoHash::Sha1 => hkdf::HKDF_SHA1_FOR_LEGACY_USE_ONLY,
-          CryptoHash::Sha256 => hkdf::HKDF_SHA256,
-          CryptoHash::Sha384 => hkdf::HKDF_SHA384,
-          CryptoHash::Sha512 => hkdf::HKDF_SHA512,
-        };
+        let algorithm =
+          match args.hash.ok_or_else(|| Error::Other(not_supported()))? {
+            CryptoHash::Sha1 => hkdf::HKDF_SHA1_FOR_LEGACY_USE_ONLY,
+            CryptoHash::Sha256 => hkdf::HKDF_SHA256,
+            CryptoHash::Sha384 => hkdf::HKDF_SHA384,
+            CryptoHash::Sha512 => hkdf::HKDF_SHA512,
+          };
 
-        let info = args
-          .info
-          .ok_or_else(|| type_error("Missing argument info".to_string()))?;
+        let info = args.info.ok_or_else(|| Error::MissingArgumentInfo)?;
         // IKM
         let secret = args.key.data;
         // L
@@ -581,23 +634,20 @@ pub async fn op_crypto_derive_bits(
         let salt = hkdf::Salt::new(algorithm, salt);
         let prk = salt.extract(&secret);
         let info = &[&*info];
-        let okm = prk.expand(info, HkdfOutput(length)).map_err(|_e| {
-          custom_error(
-            "DOMExceptionOperationError",
-            "The length provided for HKDF is too large",
-          )
-        })?;
+        let okm = prk
+          .expand(info, HkdfOutput(length))
+          .map_err(|_e| Error::HKDFLengthTooLarge)?;
         let mut r = vec![0u8; length];
         okm.fill(&mut r)?;
         Ok(r.into())
       }
-      _ => Err(type_error("Unsupported algorithm".to_string())),
+      _ => Err(Error::UnsupportedAlgorithm),
     }
   })
   .await?
 }
 
-fn read_rsa_public_key(key_data: KeyData) -> Result<RsaPublicKey, AnyError> {
+fn read_rsa_public_key(key_data: KeyData) -> Result<RsaPublicKey, Error> {
   let public_key = match key_data.r#type {
     KeyType::Private => {
       RsaPrivateKey::from_pkcs1_der(&key_data.data)?.to_public_key()
@@ -610,7 +660,7 @@ fn read_rsa_public_key(key_data: KeyData) -> Result<RsaPublicKey, AnyError> {
 
 #[op2]
 #[string]
-pub fn op_crypto_random_uuid(state: &mut OpState) -> Result<String, AnyError> {
+pub fn op_crypto_random_uuid(state: &mut OpState) -> Result<String, Error> {
   let maybe_seeded_rng = state.try_borrow_mut::<StdRng>();
   let uuid = if let Some(seeded_rng) = maybe_seeded_rng {
     let mut bytes = [0u8; 16];
@@ -631,7 +681,7 @@ pub fn op_crypto_random_uuid(state: &mut OpState) -> Result<String, AnyError> {
 pub async fn op_crypto_subtle_digest(
   #[serde] algorithm: CryptoHash,
   #[buffer] data: JsBuffer,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, Error> {
   let output = spawn_blocking(move || {
     digest::digest(algorithm.into(), &data)
       .as_ref()
@@ -655,7 +705,7 @@ pub struct WrapUnwrapKeyArg {
 pub fn op_crypto_wrap_key(
   #[serde] args: WrapUnwrapKeyArg,
   #[buffer] data: JsBuffer,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, Error> {
   let algorithm = args.algorithm;
 
   match algorithm {
@@ -663,20 +713,20 @@ pub fn op_crypto_wrap_key(
       let key = args.key.as_secret_key()?;
 
       if data.len() % 8 != 0 {
-        return Err(type_error("Data must be multiple of 8 bytes"));
+        return Err(Error::DataInvalidSize);
       }
 
       let wrapped_key = match key.len() {
         16 => KekAes128::new(key.into()).wrap_vec(&data),
         24 => KekAes192::new(key.into()).wrap_vec(&data),
         32 => KekAes256::new(key.into()).wrap_vec(&data),
-        _ => return Err(type_error("Invalid key length")),
+        _ => return Err(Error::InvalidKeyLength),
       }
-      .map_err(|_| operation_error("encryption error"))?;
+      .map_err(|_| Error::EncryptionError)?;
 
       Ok(wrapped_key.into())
     }
-    _ => Err(type_error("Unsupported algorithm")),
+    _ => Err(Error::UnsupportedAlgorithm),
   }
 }
 
@@ -685,29 +735,27 @@ pub fn op_crypto_wrap_key(
 pub fn op_crypto_unwrap_key(
   #[serde] args: WrapUnwrapKeyArg,
   #[buffer] data: JsBuffer,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, Error> {
   let algorithm = args.algorithm;
   match algorithm {
     Algorithm::AesKw => {
       let key = args.key.as_secret_key()?;
 
       if data.len() % 8 != 0 {
-        return Err(type_error("Data must be multiple of 8 bytes"));
+        return Err(Error::DataInvalidSize);
       }
 
       let unwrapped_key = match key.len() {
         16 => KekAes128::new(key.into()).unwrap_vec(&data),
         24 => KekAes192::new(key.into()).unwrap_vec(&data),
         32 => KekAes256::new(key.into()).unwrap_vec(&data),
-        _ => return Err(type_error("Invalid key length")),
+        _ => return Err(Error::InvalidKeyLength),
       }
-      .map_err(|_| {
-        operation_error("decryption error - integrity check failed")
-      })?;
+      .map_err(|_| Error::DecryptionError)?;
 
       Ok(unwrapped_key.into())
     }
-    _ => Err(type_error("Unsupported algorithm")),
+    _ => Err(Error::UnsupportedAlgorithm),
   }
 }
 
diff --git a/ext/crypto/shared.rs b/ext/crypto/shared.rs
index d06a268cd6..f70d32856c 100644
--- a/ext/crypto/shared.rs
+++ b/ext/crypto/shared.rs
@@ -2,9 +2,6 @@
 
 use std::borrow::Cow;
 
-use deno_core::error::custom_error;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::JsBuffer;
 use deno_core::ToJsBuffer;
 use elliptic_curve::sec1::ToEncodedPoint;
@@ -63,47 +60,73 @@ pub enum RustRawKeyData {
   Public(ToJsBuffer),
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum SharedError {
+  #[error("expected valid private key")]
+  ExpectedValidPrivateKey,
+  #[error("expected valid public key")]
+  ExpectedValidPublicKey,
+  #[error("expected valid private EC key")]
+  ExpectedValidPrivateECKey,
+  #[error("expected valid public EC key")]
+  ExpectedValidPublicECKey,
+  #[error("expected private key")]
+  ExpectedPrivateKey,
+  #[error("expected public key")]
+  ExpectedPublicKey,
+  #[error("expected secret key")]
+  ExpectedSecretKey,
+  #[error("failed to decode private key")]
+  FailedDecodePrivateKey,
+  #[error("failed to decode public key")]
+  FailedDecodePublicKey,
+  #[error("unsupported format")]
+  UnsupportedFormat,
+}
+
 impl V8RawKeyData {
-  pub fn as_rsa_public_key(&self) -> Result<Cow<'_, [u8]>, AnyError> {
+  pub fn as_rsa_public_key(&self) -> Result<Cow<'_, [u8]>, SharedError> {
     match self {
       V8RawKeyData::Public(data) => Ok(Cow::Borrowed(data)),
       V8RawKeyData::Private(data) => {
         let private_key = RsaPrivateKey::from_pkcs1_der(data)
-          .map_err(|_| type_error("expected valid private key"))?;
+          .map_err(|_| SharedError::ExpectedValidPrivateKey)?;
 
         let public_key_doc = private_key
           .to_public_key()
           .to_pkcs1_der()
-          .map_err(|_| type_error("expected valid public key"))?;
+          .map_err(|_| SharedError::ExpectedValidPublicKey)?;
 
         Ok(Cow::Owned(public_key_doc.as_bytes().into()))
       }
-      _ => Err(type_error("expected public key")),
+      _ => Err(SharedError::ExpectedPublicKey),
     }
   }
 
-  pub fn as_rsa_private_key(&self) -> Result<&[u8], AnyError> {
+  pub fn as_rsa_private_key(&self) -> Result<&[u8], SharedError> {
     match self {
       V8RawKeyData::Private(data) => Ok(data),
-      _ => Err(type_error("expected private key")),
+      _ => Err(SharedError::ExpectedPrivateKey),
     }
   }
 
-  pub fn as_secret_key(&self) -> Result<&[u8], AnyError> {
+  pub fn as_secret_key(&self) -> Result<&[u8], SharedError> {
     match self {
       V8RawKeyData::Secret(data) => Ok(data),
-      _ => Err(type_error("expected secret key")),
+      _ => Err(SharedError::ExpectedSecretKey),
     }
   }
 
-  pub fn as_ec_public_key_p256(&self) -> Result<p256::EncodedPoint, AnyError> {
+  pub fn as_ec_public_key_p256(
+    &self,
+  ) -> Result<p256::EncodedPoint, SharedError> {
     match self {
       V8RawKeyData::Public(data) => p256::PublicKey::from_sec1_bytes(data)
         .map(|p| p.to_encoded_point(false))
-        .map_err(|_| type_error("expected valid public EC key")),
+        .map_err(|_| SharedError::ExpectedValidPublicECKey),
       V8RawKeyData::Private(data) => {
         let signing_key = p256::SecretKey::from_pkcs8_der(data)
-          .map_err(|_| type_error("expected valid private EC key"))?;
+          .map_err(|_| SharedError::ExpectedValidPrivateECKey)?;
         Ok(signing_key.public_key().to_encoded_point(false))
       }
       // Should never reach here.
@@ -111,14 +134,16 @@ impl V8RawKeyData {
     }
   }
 
-  pub fn as_ec_public_key_p384(&self) -> Result<p384::EncodedPoint, AnyError> {
+  pub fn as_ec_public_key_p384(
+    &self,
+  ) -> Result<p384::EncodedPoint, SharedError> {
     match self {
       V8RawKeyData::Public(data) => p384::PublicKey::from_sec1_bytes(data)
         .map(|p| p.to_encoded_point(false))
-        .map_err(|_| type_error("expected valid public EC key")),
+        .map_err(|_| SharedError::ExpectedValidPublicECKey),
       V8RawKeyData::Private(data) => {
         let signing_key = p384::SecretKey::from_pkcs8_der(data)
-          .map_err(|_| type_error("expected valid private EC key"))?;
+          .map_err(|_| SharedError::ExpectedValidPrivateECKey)?;
         Ok(signing_key.public_key().to_encoded_point(false))
       }
       // Should never reach here.
@@ -126,16 +151,18 @@ impl V8RawKeyData {
     }
   }
 
-  pub fn as_ec_public_key_p521(&self) -> Result<p521::EncodedPoint, AnyError> {
+  pub fn as_ec_public_key_p521(
+    &self,
+  ) -> Result<p521::EncodedPoint, SharedError> {
     match self {
       V8RawKeyData::Public(data) => {
         // public_key is a serialized EncodedPoint
         p521::EncodedPoint::from_bytes(data)
-          .map_err(|_| type_error("expected valid public EC key"))
+          .map_err(|_| SharedError::ExpectedValidPublicECKey)
       }
       V8RawKeyData::Private(data) => {
         let signing_key = p521::SecretKey::from_pkcs8_der(data)
-          .map_err(|_| type_error("expected valid private EC key"))?;
+          .map_err(|_| SharedError::ExpectedValidPrivateECKey)?;
         Ok(signing_key.public_key().to_encoded_point(false))
       }
       // Should never reach here.
@@ -143,26 +170,10 @@ impl V8RawKeyData {
     }
   }
 
-  pub fn as_ec_private_key(&self) -> Result<&[u8], AnyError> {
+  pub fn as_ec_private_key(&self) -> Result<&[u8], SharedError> {
     match self {
       V8RawKeyData::Private(data) => Ok(data),
-      _ => Err(type_error("expected private key")),
+      _ => Err(SharedError::ExpectedPrivateKey),
     }
   }
 }
-
-pub fn data_error(msg: impl Into<Cow<'static, str>>) -> AnyError {
-  custom_error("DOMExceptionDataError", msg)
-}
-
-pub fn not_supported_error(msg: impl Into<Cow<'static, str>>) -> AnyError {
-  custom_error("DOMExceptionNotSupportedError", msg)
-}
-
-pub fn operation_error(msg: impl Into<Cow<'static, str>>) -> AnyError {
-  custom_error("DOMExceptionOperationError", msg)
-}
-
-pub fn unsupported_format() -> AnyError {
-  not_supported_error("unsupported format")
-}
diff --git a/ext/crypto/x25519.rs b/ext/crypto/x25519.rs
index 8fcad3ef21..d2c4d986b9 100644
--- a/ext/crypto/x25519.rs
+++ b/ext/crypto/x25519.rs
@@ -1,8 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 use curve25519_dalek::montgomery::MontgomeryPoint;
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::ToJsBuffer;
 use elliptic_curve::pkcs8::PrivateKeyInfo;
@@ -13,6 +11,14 @@ use spki::der::asn1::BitString;
 use spki::der::Decode;
 use spki::der::Encode;
 
+#[derive(Debug, thiserror::Error)]
+pub enum X25519Error {
+  #[error("Failed to export key")]
+  FailedExport,
+  #[error(transparent)]
+  Der(#[from] spki::der::Error),
+}
+
 #[op2(fast)]
 pub fn op_crypto_generate_x25519_keypair(
   #[buffer] pkey: &mut [u8],
@@ -47,10 +53,10 @@ pub fn op_crypto_derive_bits_x25519(
   let sh_sec = x25519_dalek::x25519(k, u);
   let point = MontgomeryPoint(sh_sec);
   if point.ct_eq(&MONTGOMERY_IDENTITY).unwrap_u8() == 1 {
-    return false;
+    return true;
   }
   secret.copy_from_slice(&sh_sec);
-  true
+  false
 }
 
 // id-X25519 OBJECT IDENTIFIER ::= { 1 3 101 110 }
@@ -113,7 +119,7 @@ pub fn op_crypto_import_pkcs8_x25519(
 #[serde]
 pub fn op_crypto_export_spki_x25519(
   #[buffer] pubkey: &[u8],
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, X25519Error> {
   let key_info = spki::SubjectPublicKeyInfo {
     algorithm: spki::AlgorithmIdentifierRef {
       // id-X25519
@@ -125,9 +131,7 @@ pub fn op_crypto_export_spki_x25519(
   Ok(
     key_info
       .to_der()
-      .map_err(|_| {
-        custom_error("DOMExceptionOperationError", "Failed to export key")
-      })?
+      .map_err(|_| X25519Error::FailedExport)?
       .into(),
   )
 }
@@ -136,7 +140,7 @@ pub fn op_crypto_export_spki_x25519(
 #[serde]
 pub fn op_crypto_export_pkcs8_x25519(
   #[buffer] pkey: &[u8],
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, X25519Error> {
   use rsa::pkcs1::der::Encode;
 
   // This should probably use OneAsymmetricKey instead
diff --git a/ext/crypto/x448.rs b/ext/crypto/x448.rs
new file mode 100644
index 0000000000..89bf48e28b
--- /dev/null
+++ b/ext/crypto/x448.rs
@@ -0,0 +1,152 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+use deno_core::op2;
+use deno_core::ToJsBuffer;
+use ed448_goldilocks::curve::MontgomeryPoint;
+use ed448_goldilocks::Scalar;
+use elliptic_curve::pkcs8::PrivateKeyInfo;
+use elliptic_curve::subtle::ConstantTimeEq;
+use rand::rngs::OsRng;
+use rand::RngCore;
+use spki::der::asn1::BitString;
+use spki::der::Decode;
+use spki::der::Encode;
+
+#[derive(Debug, thiserror::Error)]
+pub enum X448Error {
+  #[error("Failed to export key")]
+  FailedExport,
+  #[error(transparent)]
+  Der(#[from] spki::der::Error),
+}
+
+#[op2(fast)]
+pub fn op_crypto_generate_x448_keypair(
+  #[buffer] pkey: &mut [u8],
+  #[buffer] pubkey: &mut [u8],
+) {
+  let mut rng = OsRng;
+  rng.fill_bytes(pkey);
+
+  // x448(pkey, 5)
+  let point = &MontgomeryPoint::generator()
+    * &Scalar::from_bytes(pkey.try_into().unwrap());
+  pubkey.copy_from_slice(&point.0);
+}
+
+const MONTGOMERY_IDENTITY: MontgomeryPoint = MontgomeryPoint([0; 56]);
+
+#[op2(fast)]
+pub fn op_crypto_derive_bits_x448(
+  #[buffer] k: &[u8],
+  #[buffer] u: &[u8],
+  #[buffer] secret: &mut [u8],
+) -> bool {
+  let k: [u8; 56] = k.try_into().expect("Expected byteLength 56");
+  let u: [u8; 56] = u.try_into().expect("Expected byteLength 56");
+
+  // x448(k, u)
+  let point = &MontgomeryPoint(u) * &Scalar::from_bytes(k);
+  if point.ct_eq(&MONTGOMERY_IDENTITY).unwrap_u8() == 1 {
+    return true;
+  }
+
+  secret.copy_from_slice(&point.0);
+  false
+}
+
+// id-X448 OBJECT IDENTIFIER ::= { 1 3 101 111 }
+const X448_OID: const_oid::ObjectIdentifier =
+  const_oid::ObjectIdentifier::new_unwrap("1.3.101.111");
+
+#[op2]
+#[serde]
+pub fn op_crypto_export_spki_x448(
+  #[buffer] pubkey: &[u8],
+) -> Result<ToJsBuffer, X448Error> {
+  let key_info = spki::SubjectPublicKeyInfo {
+    algorithm: spki::AlgorithmIdentifierRef {
+      oid: X448_OID,
+      parameters: None,
+    },
+    subject_public_key: BitString::from_bytes(pubkey)?,
+  };
+  Ok(
+    key_info
+      .to_der()
+      .map_err(|_| X448Error::FailedExport)?
+      .into(),
+  )
+}
+
+#[op2]
+#[serde]
+pub fn op_crypto_export_pkcs8_x448(
+  #[buffer] pkey: &[u8],
+) -> Result<ToJsBuffer, X448Error> {
+  use rsa::pkcs1::der::Encode;
+
+  let pk_info = rsa::pkcs8::PrivateKeyInfo {
+    public_key: None,
+    algorithm: rsa::pkcs8::AlgorithmIdentifierRef {
+      oid: X448_OID,
+      parameters: None,
+    },
+    private_key: pkey, // OCTET STRING
+  };
+
+  let mut buf = Vec::new();
+  pk_info.encode_to_vec(&mut buf)?;
+  Ok(buf.into())
+}
+
+#[op2(fast)]
+pub fn op_crypto_import_spki_x448(
+  #[buffer] key_data: &[u8],
+  #[buffer] out: &mut [u8],
+) -> bool {
+  // 2-3.
+  let pk_info = match spki::SubjectPublicKeyInfoRef::try_from(key_data) {
+    Ok(pk_info) => pk_info,
+    Err(_) => return false,
+  };
+  // 4.
+  let alg = pk_info.algorithm.oid;
+  if alg != X448_OID {
+    return false;
+  }
+  // 5.
+  if pk_info.algorithm.parameters.is_some() {
+    return false;
+  }
+  out.copy_from_slice(pk_info.subject_public_key.raw_bytes());
+  true
+}
+
+#[op2(fast)]
+pub fn op_crypto_import_pkcs8_x448(
+  #[buffer] key_data: &[u8],
+  #[buffer] out: &mut [u8],
+) -> bool {
+  // 2-3.
+  let pk_info = match PrivateKeyInfo::from_der(key_data) {
+    Ok(pk_info) => pk_info,
+    Err(_) => return false,
+  };
+  // 4.
+  let alg = pk_info.algorithm.oid;
+  if alg != X448_OID {
+    return false;
+  }
+  // 5.
+  if pk_info.algorithm.parameters.is_some() {
+    return false;
+  }
+  // 6.
+  // CurvePrivateKey ::= OCTET STRING
+  if pk_info.private_key.len() != 56 {
+    return false;
+  }
+  out.copy_from_slice(&pk_info.private_key[2..]);
+  true
+}
diff --git a/ext/fetch/23_request.js b/ext/fetch/23_request.js
index 6211e927d9..61cac22d2e 100644
--- a/ext/fetch/23_request.js
+++ b/ext/fetch/23_request.js
@@ -269,12 +269,6 @@ class Request {
   /** @type {AbortSignal} */
   get [_signal]() {
     const signal = this[_signalCache];
-    // This signal not been created yet, and the request is still in progress
-    if (signal === undefined) {
-      const signal = newSignal();
-      this[_signalCache] = signal;
-      return signal;
-    }
     // This signal has not been created yet, but the request has already completed
     if (signal === false) {
       const signal = newSignal();
@@ -282,6 +276,18 @@ class Request {
       signal[signalAbort](signalAbortError);
       return signal;
     }
+
+    // This signal not been created yet, and the request is still in progress
+    if (signal === undefined) {
+      const signal = newSignal();
+      this[_signalCache] = signal;
+      this[_request].onCancel?.(() => {
+        signal[signalAbort](signalAbortError);
+      });
+
+      return signal;
+    }
+
     return signal;
   }
   get [_mimeType]() {
diff --git a/ext/fetch/23_response.js b/ext/fetch/23_response.js
index ff4ad5facd..278dcb7dec 100644
--- a/ext/fetch/23_response.js
+++ b/ext/fetch/23_response.js
@@ -61,6 +61,15 @@ const _mimeType = Symbol("mime type");
 const _body = Symbol("body");
 const _brand = webidl.brand;
 
+// it's slightly faster to cache these
+const webidlConvertersBodyInitDomString =
+  webidl.converters["BodyInit_DOMString?"];
+const webidlConvertersUSVString = webidl.converters["USVString"];
+const webidlConvertersUnsignedShort = webidl.converters["unsigned short"];
+const webidlConvertersAny = webidl.converters["any"];
+const webidlConvertersByteString = webidl.converters["ByteString"];
+const webidlConvertersHeadersInit = webidl.converters["HeadersInit"];
+
 /**
  * @typedef InnerResponse
  * @property {"basic" | "cors" | "default" | "error" | "opaque" | "opaqueredirect"} type
@@ -259,8 +268,8 @@ class Response {
    */
   static redirect(url, status = 302) {
     const prefix = "Failed to execute 'Response.redirect'";
-    url = webidl.converters["USVString"](url, prefix, "Argument 1");
-    status = webidl.converters["unsigned short"](status, prefix, "Argument 2");
+    url = webidlConvertersUSVString(url, prefix, "Argument 1");
+    status = webidlConvertersUnsignedShort(status, prefix, "Argument 2");
 
     const baseURL = getLocationHref();
     const parsedURL = new URL(url, baseURL);
@@ -286,8 +295,8 @@ class Response {
    */
   static json(data = undefined, init = { __proto__: null }) {
     const prefix = "Failed to execute 'Response.json'";
-    data = webidl.converters.any(data);
-    init = webidl.converters["ResponseInit_fast"](init, prefix, "Argument 2");
+    data = webidlConvertersAny(data);
+    init = webidlConvertersResponseInitFast(init, prefix, "Argument 2");
 
     const str = serializeJSValueToJSONString(data);
     const res = extractBody(str);
@@ -313,8 +322,8 @@ class Response {
     }
 
     const prefix = "Failed to construct 'Response'";
-    body = webidl.converters["BodyInit_DOMString?"](body, prefix, "Argument 1");
-    init = webidl.converters["ResponseInit_fast"](init, prefix, "Argument 2");
+    body = webidlConvertersBodyInitDomString(body, prefix, "Argument 1");
+    init = webidlConvertersResponseInitFast(init, prefix, "Argument 2");
 
     this[_response] = newInnerResponse();
     this[_headers] = headersFromHeaderList(
@@ -443,47 +452,49 @@ webidl.converters["Response"] = webidl.createInterfaceConverter(
   "Response",
   ResponsePrototype,
 );
-webidl.converters["ResponseInit"] = webidl.createDictionaryConverter(
-  "ResponseInit",
-  [{
-    key: "status",
-    defaultValue: 200,
-    converter: webidl.converters["unsigned short"],
-  }, {
-    key: "statusText",
-    defaultValue: "",
-    converter: webidl.converters["ByteString"],
-  }, {
-    key: "headers",
-    converter: webidl.converters["HeadersInit"],
-  }],
-);
-webidl.converters["ResponseInit_fast"] = function (
-  init,
-  prefix,
-  context,
-  opts,
-) {
-  if (init === undefined || init === null) {
-    return { status: 200, statusText: "", headers: undefined };
-  }
-  // Fast path, if not a proxy
-  if (typeof init === "object" && !core.isProxy(init)) {
-    // Not a proxy fast path
-    const status = init.status !== undefined
-      ? webidl.converters["unsigned short"](init.status)
-      : 200;
-    const statusText = init.statusText !== undefined
-      ? webidl.converters["ByteString"](init.statusText)
-      : "";
-    const headers = init.headers !== undefined
-      ? webidl.converters["HeadersInit"](init.headers)
-      : undefined;
-    return { status, statusText, headers };
-  }
-  // Slow default path
-  return webidl.converters["ResponseInit"](init, prefix, context, opts);
-};
+const webidlConvertersResponseInit = webidl.converters["ResponseInit"] = webidl
+  .createDictionaryConverter(
+    "ResponseInit",
+    [{
+      key: "status",
+      defaultValue: 200,
+      converter: webidlConvertersUnsignedShort,
+    }, {
+      key: "statusText",
+      defaultValue: "",
+      converter: webidlConvertersByteString,
+    }, {
+      key: "headers",
+      converter: webidlConvertersHeadersInit,
+    }],
+  );
+const webidlConvertersResponseInitFast = webidl
+  .converters["ResponseInit_fast"] = function (
+    init,
+    prefix,
+    context,
+    opts,
+  ) {
+    if (init === undefined || init === null) {
+      return { status: 200, statusText: "", headers: undefined };
+    }
+    // Fast path, if not a proxy
+    if (typeof init === "object" && !core.isProxy(init)) {
+      // Not a proxy fast path
+      const status = init.status !== undefined
+        ? webidlConvertersUnsignedShort(init.status)
+        : 200;
+      const statusText = init.statusText !== undefined
+        ? webidlConvertersByteString(init.statusText)
+        : "";
+      const headers = init.headers !== undefined
+        ? webidlConvertersHeadersInit(init.headers)
+        : undefined;
+      return { status, statusText, headers };
+    }
+    // Slow default path
+    return webidlConvertersResponseInit(init, prefix, context, opts);
+  };
 
 /**
  * @param {Response} response
diff --git a/ext/fetch/Cargo.toml b/ext/fetch/Cargo.toml
index 2ec1c25f0c..56d416bbb8 100644
--- a/ext/fetch/Cargo.toml
+++ b/ext/fetch/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_fetch"
-version = "0.192.0"
+version = "0.201.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -32,6 +32,7 @@ percent-encoding.workspace = true
 rustls-webpki.workspace = true
 serde.workspace = true
 serde_json.workspace = true
+thiserror.workspace = true
 tokio.workspace = true
 tokio-rustls.workspace = true
 tokio-socks.workspace = true
diff --git a/ext/fetch/fs_fetch_handler.rs b/ext/fetch/fs_fetch_handler.rs
index 4c2b81f356..c236dd9c67 100644
--- a/ext/fetch/fs_fetch_handler.rs
+++ b/ext/fetch/fs_fetch_handler.rs
@@ -4,7 +4,6 @@ use crate::CancelHandle;
 use crate::CancelableResponseFuture;
 use crate::FetchHandler;
 
-use deno_core::error::type_error;
 use deno_core::futures::FutureExt;
 use deno_core::futures::TryFutureExt;
 use deno_core::futures::TryStreamExt;
@@ -42,9 +41,7 @@ impl FetchHandler for FsFetchHandler {
         .map_err(|_| ())?;
       Ok::<_, ()>(response)
     }
-    .map_err(move |_| {
-      type_error("NetworkError when attempting to fetch resource")
-    })
+    .map_err(move |_| super::FetchError::NetworkError)
     .or_cancel(&cancel_handle)
     .boxed_local();
 
diff --git a/ext/fetch/lib.rs b/ext/fetch/lib.rs
index 88f3038528..7ef26431c2 100644
--- a/ext/fetch/lib.rs
+++ b/ext/fetch/lib.rs
@@ -17,10 +17,6 @@ use std::sync::Arc;
 use std::task::Context;
 use std::task::Poll;
 
-use deno_core::anyhow::anyhow;
-use deno_core::anyhow::Error;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::futures::stream::Peekable;
 use deno_core::futures::Future;
 use deno_core::futures::FutureExt;
@@ -28,6 +24,7 @@ use deno_core::futures::Stream;
 use deno_core::futures::StreamExt;
 use deno_core::futures::TryFutureExt;
 use deno_core::op2;
+use deno_core::url;
 use deno_core::url::Url;
 use deno_core::AsyncRefCell;
 use deno_core::AsyncResult;
@@ -42,6 +39,7 @@ use deno_core::OpState;
 use deno_core::RcRef;
 use deno_core::Resource;
 use deno_core::ResourceId;
+use deno_permissions::PermissionCheckError;
 use deno_tls::rustls::RootCertStore;
 use deno_tls::Proxy;
 use deno_tls::RootCertStoreProvider;
@@ -87,15 +85,18 @@ pub struct Options {
   pub root_cert_store_provider: Option<Arc<dyn RootCertStoreProvider>>,
   pub proxy: Option<Proxy>,
   #[allow(clippy::type_complexity)]
-  pub request_builder_hook:
-    Option<fn(&mut http::Request<ReqBody>) -> Result<(), AnyError>>,
+  pub request_builder_hook: Option<
+    fn(&mut http::Request<ReqBody>) -> Result<(), deno_core::error::AnyError>,
+  >,
   pub unsafely_ignore_certificate_errors: Option<Vec<String>>,
   pub client_cert_chain_and_key: TlsKeys,
   pub file_fetch_handler: Rc<dyn FetchHandler>,
 }
 
 impl Options {
-  pub fn root_cert_store(&self) -> Result<Option<RootCertStore>, AnyError> {
+  pub fn root_cert_store(
+    &self,
+  ) -> Result<Option<RootCertStore>, deno_core::error::AnyError> {
     Ok(match &self.root_cert_store_provider {
       Some(provider) => Some(provider.get_or_try_init()?.clone()),
       None => None,
@@ -144,6 +145,51 @@ deno_core::extension!(deno_fetch,
   },
 );
 
+#[derive(Debug, thiserror::Error)]
+pub enum FetchError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  Permission(#[from] PermissionCheckError),
+  #[error("NetworkError when attempting to fetch resource")]
+  NetworkError,
+  #[error("Fetching files only supports the GET method: received {0}")]
+  FsNotGet(Method),
+  #[error("Invalid URL {0}")]
+  InvalidUrl(Url),
+  #[error(transparent)]
+  InvalidHeaderName(#[from] http::header::InvalidHeaderName),
+  #[error(transparent)]
+  InvalidHeaderValue(#[from] http::header::InvalidHeaderValue),
+  #[error("{0:?}")]
+  DataUrl(data_url::DataUrlError),
+  #[error("{0:?}")]
+  Base64(data_url::forgiving_base64::InvalidBase64),
+  #[error("Blob for the given URL not found.")]
+  BlobNotFound,
+  #[error("Url scheme '{0}' not supported")]
+  SchemeNotSupported(String),
+  #[error("Request was cancelled")]
+  RequestCanceled,
+  #[error(transparent)]
+  Http(#[from] http::Error),
+  #[error(transparent)]
+  ClientCreate(#[from] HttpClientCreateError),
+  #[error(transparent)]
+  Url(#[from] url::ParseError),
+  #[error(transparent)]
+  Method(#[from] http::method::InvalidMethod),
+  #[error(transparent)]
+  ClientSend(#[from] ClientSendError),
+  #[error(transparent)]
+  RequestBuilderHook(deno_core::error::AnyError),
+  #[error(transparent)]
+  Io(#[from] std::io::Error),
+  // Only used for node upgrade
+  #[error(transparent)]
+  Hyper(#[from] hyper::Error),
+}
+
 pub type CancelableResponseFuture =
   Pin<Box<dyn Future<Output = CancelableResponseResult>>>;
 
@@ -170,11 +216,7 @@ impl FetchHandler for DefaultFileFetchHandler {
     _state: &mut OpState,
     _url: &Url,
   ) -> (CancelableResponseFuture, Option<Rc<CancelHandle>>) {
-    let fut = async move {
-      Ok(Err(type_error(
-        "NetworkError when attempting to fetch resource",
-      )))
-    };
+    let fut = async move { Ok(Err(FetchError::NetworkError)) };
     (Box::pin(fut), None)
   }
 }
@@ -191,7 +233,7 @@ pub struct FetchReturn {
 
 pub fn get_or_create_client_from_state(
   state: &mut OpState,
-) -> Result<Client, AnyError> {
+) -> Result<Client, HttpClientCreateError> {
   if let Some(client) = state.try_borrow::<Client>() {
     Ok(client.clone())
   } else {
@@ -204,11 +246,13 @@ pub fn get_or_create_client_from_state(
 
 pub fn create_client_from_options(
   options: &Options,
-) -> Result<Client, AnyError> {
+) -> Result<Client, HttpClientCreateError> {
   create_http_client(
     &options.user_agent,
     CreateHttpClientOptions {
-      root_cert_store: options.root_cert_store()?,
+      root_cert_store: options
+        .root_cert_store()
+        .map_err(HttpClientCreateError::RootCertStore)?,
       ca_certs: vec![],
       proxy: options.proxy.clone(),
       unsafely_ignore_certificate_errors: options
@@ -230,7 +274,9 @@ pub fn create_client_from_options(
 #[allow(clippy::type_complexity)]
 pub struct ResourceToBodyAdapter(
   Rc<dyn Resource>,
-  Option<Pin<Box<dyn Future<Output = Result<BufView, Error>>>>>,
+  Option<
+    Pin<Box<dyn Future<Output = Result<BufView, deno_core::error::AnyError>>>>,
+  >,
 );
 
 impl ResourceToBodyAdapter {
@@ -246,7 +292,7 @@ unsafe impl Send for ResourceToBodyAdapter {}
 unsafe impl Sync for ResourceToBodyAdapter {}
 
 impl Stream for ResourceToBodyAdapter {
-  type Item = Result<Bytes, Error>;
+  type Item = Result<Bytes, deno_core::error::AnyError>;
 
   fn poll_next(
     self: Pin<&mut Self>,
@@ -276,7 +322,7 @@ impl Stream for ResourceToBodyAdapter {
 
 impl hyper::body::Body for ResourceToBodyAdapter {
   type Data = Bytes;
-  type Error = Error;
+  type Error = deno_core::error::AnyError;
 
   fn poll_frame(
     self: Pin<&mut Self>,
@@ -301,13 +347,13 @@ pub trait FetchPermissions {
     &mut self,
     url: &Url,
     api_name: &str,
-  ) -> Result<(), AnyError>;
+  ) -> Result<(), PermissionCheckError>;
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
   fn check_read<'a>(
     &mut self,
     p: &'a Path,
     api_name: &str,
-  ) -> Result<Cow<'a, Path>, AnyError>;
+  ) -> Result<Cow<'a, Path>, PermissionCheckError>;
 }
 
 impl FetchPermissions for deno_permissions::PermissionsContainer {
@@ -316,7 +362,7 @@ impl FetchPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     url: &Url,
     api_name: &str,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_net_url(self, url, api_name)
   }
 
@@ -325,7 +371,7 @@ impl FetchPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     path: &'a Path,
     api_name: &str,
-  ) -> Result<Cow<'a, Path>, AnyError> {
+  ) -> Result<Cow<'a, Path>, PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_read_path(
       self,
       path,
@@ -346,12 +392,15 @@ pub fn op_fetch<FP>(
   has_body: bool,
   #[buffer] data: Option<JsBuffer>,
   #[smi] resource: Option<ResourceId>,
-) -> Result<FetchReturn, AnyError>
+) -> Result<FetchReturn, FetchError>
 where
   FP: FetchPermissions + 'static,
 {
   let (client, allow_host) = if let Some(rid) = client_rid {
-    let r = state.resource_table.get::<HttpClientResource>(rid)?;
+    let r = state
+      .resource_table
+      .get::<HttpClientResource>(rid)
+      .map_err(FetchError::Resource)?;
     (r.client.clone(), r.allow_host)
   } else {
     (get_or_create_client_from_state(state)?, false)
@@ -364,9 +413,7 @@ where
   let scheme = url.scheme();
   let (request_rid, cancel_handle_rid) = match scheme {
     "file" => {
-      let path = url.to_file_path().map_err(|_| {
-        type_error("NetworkError when attempting to fetch resource")
-      })?;
+      let path = url.to_file_path().map_err(|_| FetchError::NetworkError)?;
       let permissions = state.borrow_mut::<FP>();
       let path = permissions.check_read(&path, "fetch()")?;
       let url = match path {
@@ -375,9 +422,7 @@ where
       };
 
       if method != Method::GET {
-        return Err(type_error(format!(
-          "Fetching files only supports the GET method: received {method}"
-        )));
+        return Err(FetchError::FsNotGet(method));
       }
 
       let Options {
@@ -402,7 +447,7 @@ where
       let uri = url
         .as_str()
         .parse::<Uri>()
-        .map_err(|_| type_error(format!("Invalid URL {url}")))?;
+        .map_err(|_| FetchError::InvalidUrl(url.clone()))?;
 
       let mut con_len = None;
       let body = if has_body {
@@ -416,7 +461,10 @@ where
               .boxed()
           }
           (_, Some(resource)) => {
-            let resource = state.resource_table.take_any(resource)?;
+            let resource = state
+              .resource_table
+              .take_any(resource)
+              .map_err(FetchError::Resource)?;
             match resource.size_hint() {
               (body_size, Some(n)) if body_size == n && body_size > 0 => {
                 con_len = Some(body_size);
@@ -453,10 +501,8 @@ where
       }
 
       for (key, value) in headers {
-        let name = HeaderName::from_bytes(&key)
-          .map_err(|err| type_error(err.to_string()))?;
-        let v = HeaderValue::from_bytes(&value)
-          .map_err(|err| type_error(err.to_string()))?;
+        let name = HeaderName::from_bytes(&key)?;
+        let v = HeaderValue::from_bytes(&value)?;
 
         if (name != HOST || allow_host) && name != CONTENT_LENGTH {
           request.headers_mut().append(name, v);
@@ -474,20 +520,18 @@ where
       let options = state.borrow::<Options>();
       if let Some(request_builder_hook) = options.request_builder_hook {
         request_builder_hook(&mut request)
-          .map_err(|err| type_error(err.to_string()))?;
+          .map_err(FetchError::RequestBuilderHook)?;
       }
 
       let cancel_handle = CancelHandle::new_rc();
       let cancel_handle_ = cancel_handle.clone();
 
-      let fut = {
-        async move {
-          client
-            .send(request)
-            .map_err(Into::into)
-            .or_cancel(cancel_handle_)
-            .await
-        }
+      let fut = async move {
+        client
+          .send(request)
+          .map_err(Into::into)
+          .or_cancel(cancel_handle_)
+          .await
       };
 
       let request_rid = state.resource_table.add(FetchRequestResource {
@@ -501,12 +545,10 @@ where
       (request_rid, Some(cancel_handle_rid))
     }
     "data" => {
-      let data_url = DataUrl::process(url.as_str())
-        .map_err(|e| type_error(format!("{e:?}")))?;
+      let data_url =
+        DataUrl::process(url.as_str()).map_err(FetchError::DataUrl)?;
 
-      let (body, _) = data_url
-        .decode_to_vec()
-        .map_err(|e| type_error(format!("{e:?}")))?;
+      let (body, _) = data_url.decode_to_vec().map_err(FetchError::Base64)?;
       let body = http_body_util::Full::new(body.into())
         .map_err(|never| match never {})
         .boxed();
@@ -528,11 +570,9 @@ where
     "blob" => {
       // Blob URL resolution happens in the JS side of fetch. If we got here is
       // because the URL isn't an object URL.
-      return Err(type_error("Blob for the given URL not found."));
-    }
-    _ => {
-      return Err(type_error(format!("Url scheme '{scheme}' not supported")))
+      return Err(FetchError::BlobNotFound);
     }
+    _ => return Err(FetchError::SchemeNotSupported(scheme.to_string())),
   };
 
   Ok(FetchReturn {
@@ -564,11 +604,12 @@ pub struct FetchResponse {
 pub async fn op_fetch_send(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<FetchResponse, AnyError> {
+) -> Result<FetchResponse, FetchError> {
   let request = state
     .borrow_mut()
     .resource_table
-    .take::<FetchRequestResource>(rid)?;
+    .take::<FetchRequestResource>(rid)
+    .map_err(FetchError::Resource)?;
 
   let request = Rc::try_unwrap(request)
     .ok()
@@ -581,22 +622,23 @@ pub async fn op_fetch_send(
       // If any error in the chain is a hyper body error, return that as a special result we can use to
       // reconstruct an error chain (eg: `new TypeError(..., { cause: new Error(...) })`).
       // TODO(mmastrac): it would be a lot easier if we just passed a v8::Global through here instead
-      let mut err_ref: &dyn std::error::Error = err.as_ref();
-      while let Some(err_src) = std::error::Error::source(err_ref) {
-        if let Some(err_src) = err_src.downcast_ref::<hyper::Error>() {
-          if let Some(err_src) = std::error::Error::source(err_src) {
-            return Ok(FetchResponse {
-              error: Some((err.to_string(), err_src.to_string())),
-              ..Default::default()
-            });
+
+      if let FetchError::ClientSend(err_src) = &err {
+        if let Some(client_err) = std::error::Error::source(&err_src.source) {
+          if let Some(err_src) = client_err.downcast_ref::<hyper::Error>() {
+            if let Some(err_src) = std::error::Error::source(err_src) {
+              return Ok(FetchResponse {
+                error: Some((err.to_string(), err_src.to_string())),
+                ..Default::default()
+              });
+            }
           }
         }
-        err_ref = err_src;
       }
 
-      return Err(type_error(err.to_string()));
+      return Err(err);
     }
-    Err(_) => return Err(type_error("Request was cancelled")),
+    Err(_) => return Err(FetchError::RequestCanceled),
   };
 
   let status = res.status();
@@ -636,7 +678,7 @@ pub async fn op_fetch_send(
 }
 
 type CancelableResponseResult =
-  Result<Result<http::Response<ResBody>, AnyError>, Canceled>;
+  Result<Result<http::Response<ResBody>, FetchError>, Canceled>;
 
 pub struct FetchRequestResource {
   pub future: Pin<Box<dyn Future<Output = CancelableResponseResult>>>,
@@ -691,7 +733,7 @@ impl FetchResponseResource {
     }
   }
 
-  pub async fn upgrade(self) -> Result<hyper::upgrade::Upgraded, AnyError> {
+  pub async fn upgrade(self) -> Result<hyper::upgrade::Upgraded, hyper::Error> {
     let reader = self.response_reader.into_inner();
     match reader {
       FetchResponseReader::Start(resp) => Ok(hyper::upgrade::on(resp).await?),
@@ -746,7 +788,9 @@ impl Resource for FetchResponseResource {
             // safely call `await` on it without creating a race condition.
             Some(_) => match reader.as_mut().next().await.unwrap() {
               Ok(chunk) => assert!(chunk.is_empty()),
-              Err(err) => break Err(type_error(err.to_string())),
+              Err(err) => {
+                break Err(deno_core::error::type_error(err.to_string()))
+              }
             },
             None => break Ok(BufView::empty()),
           }
@@ -809,7 +853,7 @@ pub fn op_fetch_custom_client<FP>(
   state: &mut OpState,
   #[serde] args: CreateHttpClientArgs,
   #[cppgc] tls_keys: &TlsKeysHolder,
-) -> Result<ResourceId, AnyError>
+) -> Result<ResourceId, FetchError>
 where
   FP: FetchPermissions + 'static,
 {
@@ -829,7 +873,9 @@ where
   let client = create_http_client(
     &options.user_agent,
     CreateHttpClientOptions {
-      root_cert_store: options.root_cert_store()?,
+      root_cert_store: options
+        .root_cert_store()
+        .map_err(HttpClientCreateError::RootCertStore)?,
       ca_certs,
       proxy: args.proxy,
       unsafely_ignore_certificate_errors: options
@@ -887,19 +933,34 @@ impl Default for CreateHttpClientOptions {
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum HttpClientCreateError {
+  #[error(transparent)]
+  Tls(deno_tls::TlsError),
+  #[error("Illegal characters in User-Agent: received {0}")]
+  InvalidUserAgent(String),
+  #[error("invalid proxy url")]
+  InvalidProxyUrl,
+  #[error("Cannot create Http Client: either `http1` or `http2` needs to be set to true")]
+  HttpVersionSelectionInvalid,
+  #[error(transparent)]
+  RootCertStore(deno_core::error::AnyError),
+}
+
 /// Create new instance of async Client. This client supports
 /// proxies and doesn't follow redirects.
 pub fn create_http_client(
   user_agent: &str,
   options: CreateHttpClientOptions,
-) -> Result<Client, AnyError> {
+) -> Result<Client, HttpClientCreateError> {
   let mut tls_config = deno_tls::create_client_config(
     options.root_cert_store,
     options.ca_certs,
     options.unsafely_ignore_certificate_errors,
     options.client_cert_chain_and_key.into(),
     deno_tls::SocketUse::Http,
-  )?;
+  )
+  .map_err(HttpClientCreateError::Tls)?;
 
   // Proxy TLS should not send ALPN
   tls_config.alpn_protocols.clear();
@@ -919,9 +980,7 @@ pub fn create_http_client(
   http_connector.enforce_http(false);
 
   let user_agent = user_agent.parse::<HeaderValue>().map_err(|_| {
-    type_error(format!(
-      "Illegal characters in User-Agent: received {user_agent}"
-    ))
+    HttpClientCreateError::InvalidUserAgent(user_agent.to_string())
   })?;
 
   let mut builder =
@@ -932,7 +991,7 @@ pub fn create_http_client(
   let mut proxies = proxy::from_env();
   if let Some(proxy) = options.proxy {
     let mut intercept = proxy::Intercept::all(&proxy.url)
-      .ok_or_else(|| type_error("invalid proxy url"))?;
+      .ok_or_else(|| HttpClientCreateError::InvalidProxyUrl)?;
     if let Some(basic_auth) = &proxy.basic_auth {
       intercept.set_auth(&basic_auth.username, &basic_auth.password);
     }
@@ -964,7 +1023,7 @@ pub fn create_http_client(
     }
     (true, true) => {}
     (false, false) => {
-      return Err(type_error("Cannot create Http Client: either `http1` or `http2` needs to be set to true"))
+      return Err(HttpClientCreateError::HttpVersionSelectionInvalid)
     }
   }
 
@@ -980,10 +1039,8 @@ pub fn create_http_client(
 
 #[op2]
 #[serde]
-pub fn op_utf8_to_byte_string(
-  #[string] input: String,
-) -> Result<ByteString, AnyError> {
-  Ok(input.into())
+pub fn op_utf8_to_byte_string(#[string] input: String) -> ByteString {
+  input.into()
 }
 
 #[derive(Clone, Debug)]
@@ -1003,7 +1060,7 @@ const STAR_STAR: HeaderValue = HeaderValue::from_static("*/*");
 #[derive(Debug)]
 pub struct ClientSendError {
   uri: Uri,
-  source: hyper_util::client::legacy::Error,
+  pub source: hyper_util::client::legacy::Error,
 }
 
 impl ClientSendError {
@@ -1075,12 +1132,14 @@ impl Client {
       .oneshot(req)
       .await
       .map_err(|e| ClientSendError { uri, source: e })?;
-    Ok(resp.map(|b| b.map_err(|e| anyhow!(e)).boxed()))
+    Ok(resp.map(|b| b.map_err(|e| deno_core::anyhow::anyhow!(e)).boxed()))
   }
 }
 
-pub type ReqBody = http_body_util::combinators::BoxBody<Bytes, Error>;
-pub type ResBody = http_body_util::combinators::BoxBody<Bytes, Error>;
+pub type ReqBody =
+  http_body_util::combinators::BoxBody<Bytes, deno_core::error::AnyError>;
+pub type ResBody =
+  http_body_util::combinators::BoxBody<Bytes, deno_core::error::AnyError>;
 
 /// Copied from https://github.com/seanmonstar/reqwest/blob/b9d62a0323d96f11672a61a17bf8849baec00275/src/async_impl/request.rs#L572
 /// Check the request URL for a "username:password" type authority, and if
diff --git a/ext/ffi/Cargo.toml b/ext/ffi/Cargo.toml
index 8c4ccdc9ba..295e8be846 100644
--- a/ext/ffi/Cargo.toml
+++ b/ext/ffi/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_ffi"
-version = "0.155.0"
+version = "0.164.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -21,9 +21,12 @@ dynasmrt = "1.2.3"
 libffi = "=3.2.0"
 libffi-sys = "=2.3.0"
 log.workspace = true
+num-bigint.workspace = true
 serde.workspace = true
 serde-value = "0.7"
 serde_json = "1.0"
+thiserror.workspace = true
+tokio.workspace = true
 
 [target.'cfg(windows)'.dependencies]
 winapi = { workspace = true, features = ["errhandlingapi", "minwindef", "ntdef", "winbase", "winnt"] }
diff --git a/ext/ffi/call.rs b/ext/ffi/call.rs
index 3572b9e813..bbff0ee48f 100644
--- a/ext/ffi/call.rs
+++ b/ext/ffi/call.rs
@@ -7,23 +7,38 @@ use crate::symbol::NativeType;
 use crate::symbol::Symbol;
 use crate::FfiPermissions;
 use crate::ForeignFunction;
-use deno_core::anyhow::anyhow;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::serde_json::Value;
+use deno_core::serde_v8::BigInt as V8BigInt;
 use deno_core::serde_v8::ExternalPointer;
 use deno_core::unsync::spawn_blocking;
 use deno_core::v8;
 use deno_core::OpState;
 use deno_core::ResourceId;
 use libffi::middle::Arg;
+use num_bigint::BigInt;
 use serde::Serialize;
 use std::cell::RefCell;
 use std::ffi::c_void;
 use std::future::Future;
 use std::rc::Rc;
 
+#[derive(Debug, thiserror::Error)]
+pub enum CallError {
+  #[error(transparent)]
+  IR(#[from] IRError),
+  #[error("Nonblocking FFI call failed: {0}")]
+  NonblockingCallFailure(#[source] tokio::task::JoinError),
+  #[error("Invalid FFI symbol name: '{0}'")]
+  InvalidSymbol(String),
+  #[error(transparent)]
+  Permission(#[from] deno_permissions::PermissionCheckError),
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  Callback(#[from] super::CallbackError),
+}
+
 // SAFETY: Makes an FFI call
 unsafe fn ffi_call_rtype_struct(
   cif: &libffi::middle::Cif,
@@ -45,7 +60,7 @@ pub(crate) fn ffi_call_sync<'scope>(
   args: v8::FunctionCallbackArguments,
   symbol: &Symbol,
   out_buffer: Option<OutBuffer>,
-) -> Result<NativeValue, AnyError>
+) -> Result<NativeValue, CallError>
 where
   'scope: 'scope,
 {
@@ -191,6 +206,7 @@ where
 #[serde(untagged)]
 pub enum FfiValue {
   Value(Value),
+  BigInt(V8BigInt),
   External(ExternalPointer),
 }
 
@@ -201,7 +217,7 @@ fn ffi_call(
   parameter_types: &[NativeType],
   result_type: NativeType,
   out_buffer: Option<OutBuffer>,
-) -> Result<FfiValue, AnyError> {
+) -> FfiValue {
   let call_args: Vec<Arg> = call_args
     .iter()
     .enumerate()
@@ -214,7 +230,7 @@ fn ffi_call(
   // SAFETY: types in the `Cif` match the actual calling convention and
   // types of symbol.
   unsafe {
-    Ok(match result_type {
+    match result_type {
       NativeType::Void => {
         cif.call::<()>(fun_ptr, &call_args);
         FfiValue::Value(Value::from(()))
@@ -240,18 +256,18 @@ fn ffi_call(
       NativeType::I32 => {
         FfiValue::Value(Value::from(cif.call::<i32>(fun_ptr, &call_args)))
       }
-      NativeType::U64 => {
-        FfiValue::Value(Value::from(cif.call::<u64>(fun_ptr, &call_args)))
-      }
-      NativeType::I64 => {
-        FfiValue::Value(Value::from(cif.call::<i64>(fun_ptr, &call_args)))
-      }
-      NativeType::USize => {
-        FfiValue::Value(Value::from(cif.call::<usize>(fun_ptr, &call_args)))
-      }
-      NativeType::ISize => {
-        FfiValue::Value(Value::from(cif.call::<isize>(fun_ptr, &call_args)))
-      }
+      NativeType::U64 => FfiValue::BigInt(V8BigInt::from(BigInt::from(
+        cif.call::<u64>(fun_ptr, &call_args),
+      ))),
+      NativeType::I64 => FfiValue::BigInt(V8BigInt::from(BigInt::from(
+        cif.call::<i64>(fun_ptr, &call_args),
+      ))),
+      NativeType::USize => FfiValue::BigInt(V8BigInt::from(BigInt::from(
+        cif.call::<usize>(fun_ptr, &call_args),
+      ))),
+      NativeType::ISize => FfiValue::BigInt(V8BigInt::from(BigInt::from(
+        cif.call::<isize>(fun_ptr, &call_args),
+      ))),
       NativeType::F32 => {
         FfiValue::Value(Value::from(cif.call::<f32>(fun_ptr, &call_args)))
       }
@@ -267,7 +283,7 @@ fn ffi_call(
         ffi_call_rtype_struct(cif, &fun_ptr, call_args, out_buffer.unwrap().0);
         FfiValue::Value(Value::Null)
       }
-    })
+    }
   }
 }
 
@@ -280,7 +296,7 @@ pub fn op_ffi_call_ptr_nonblocking<FP>(
   #[serde] def: ForeignFunction,
   parameters: v8::Local<v8::Array>,
   out_buffer: Option<v8::Local<v8::TypedArray>>,
-) -> Result<impl Future<Output = Result<FfiValue, AnyError>>, AnyError>
+) -> Result<impl Future<Output = Result<FfiValue, CallError>>, CallError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -309,7 +325,7 @@ where
   Ok(async move {
     let result = join_handle
       .await
-      .map_err(|err| anyhow!("Nonblocking FFI call failed: {}", err))??;
+      .map_err(CallError::NonblockingCallFailure)?;
     // SAFETY: Same return type declared to libffi; trust user to have it right beyond that.
     Ok(result)
   })
@@ -325,16 +341,17 @@ pub fn op_ffi_call_nonblocking(
   #[string] symbol: String,
   parameters: v8::Local<v8::Array>,
   out_buffer: Option<v8::Local<v8::TypedArray>>,
-) -> Result<impl Future<Output = Result<FfiValue, AnyError>>, AnyError> {
+) -> Result<impl Future<Output = Result<FfiValue, CallError>>, CallError> {
   let symbol = {
     let state = state.borrow();
-    let resource = state.resource_table.get::<DynamicLibraryResource>(rid)?;
+    let resource = state
+      .resource_table
+      .get::<DynamicLibraryResource>(rid)
+      .map_err(CallError::Resource)?;
     let symbols = &resource.symbols;
     *symbols
       .get(&symbol)
-      .ok_or_else(|| {
-        type_error(format!("Invalid FFI symbol name: '{symbol}'"))
-      })?
+      .ok_or_else(|| CallError::InvalidSymbol(symbol))?
       .clone()
   };
 
@@ -362,7 +379,7 @@ pub fn op_ffi_call_nonblocking(
   Ok(async move {
     let result = join_handle
       .await
-      .map_err(|err| anyhow!("Nonblocking FFI call failed: {}", err))??;
+      .map_err(CallError::NonblockingCallFailure)?;
     // SAFETY: Same return type declared to libffi; trust user to have it right beyond that.
     Ok(result)
   })
@@ -377,7 +394,7 @@ pub fn op_ffi_call_ptr<FP>(
   #[serde] def: ForeignFunction,
   parameters: v8::Local<v8::Array>,
   out_buffer: Option<v8::Local<v8::TypedArray>>,
-) -> Result<FfiValue, AnyError>
+) -> Result<FfiValue, CallError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -399,7 +416,7 @@ where
     &def.parameters,
     def.result.clone(),
     out_buffer_ptr,
-  )?;
+  );
   // SAFETY: Same return type declared to libffi; trust user to have it right beyond that.
   Ok(result)
 }
diff --git a/ext/ffi/callback.rs b/ext/ffi/callback.rs
index 6fa166f52b..29583c800c 100644
--- a/ext/ffi/callback.rs
+++ b/ext/ffi/callback.rs
@@ -3,7 +3,6 @@
 use crate::symbol::NativeType;
 use crate::FfiPermissions;
 use crate::ForeignFunction;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::v8;
 use deno_core::v8::TryCatch;
@@ -34,6 +33,16 @@ thread_local! {
   static LOCAL_THREAD_ID: RefCell<u32> = const { RefCell::new(0) };
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum CallbackError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  Permission(#[from] deno_permissions::PermissionCheckError),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
 #[derive(Clone)]
 pub struct PtrSymbol {
   pub cif: libffi::middle::Cif,
@@ -44,7 +53,7 @@ impl PtrSymbol {
   pub fn new(
     fn_ptr: *mut c_void,
     def: &ForeignFunction,
-  ) -> Result<Self, AnyError> {
+  ) -> Result<Self, CallbackError> {
     let ptr = libffi::middle::CodePtr::from_ptr(fn_ptr as _);
     let cif = libffi::middle::Cif::new(
       def
@@ -52,8 +61,13 @@ impl PtrSymbol {
         .clone()
         .into_iter()
         .map(libffi::middle::Type::try_from)
-        .collect::<Result<Vec<_>, _>>()?,
-      def.result.clone().try_into()?,
+        .collect::<Result<Vec<_>, _>>()
+        .map_err(CallbackError::Other)?,
+      def
+        .result
+        .clone()
+        .try_into()
+        .map_err(CallbackError::Other)?,
     );
 
     Ok(Self { cif, ptr })
@@ -522,10 +536,12 @@ unsafe fn do_ffi_callback(
 pub fn op_ffi_unsafe_callback_ref(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<impl Future<Output = Result<(), AnyError>>, AnyError> {
+) -> Result<impl Future<Output = ()>, CallbackError> {
   let state = state.borrow();
-  let callback_resource =
-    state.resource_table.get::<UnsafeCallbackResource>(rid)?;
+  let callback_resource = state
+    .resource_table
+    .get::<UnsafeCallbackResource>(rid)
+    .map_err(CallbackError::Resource)?;
 
   Ok(async move {
     let info: &mut CallbackInfo =
@@ -536,7 +552,6 @@ pub fn op_ffi_unsafe_callback_ref(
       .into_future()
       .or_cancel(callback_resource.cancel.clone())
       .await;
-    Ok(())
   })
 }
 
@@ -552,7 +567,7 @@ pub fn op_ffi_unsafe_callback_create<FP, 'scope>(
   scope: &mut v8::HandleScope<'scope>,
   #[serde] args: RegisterCallbackArgs,
   cb: v8::Local<v8::Function>,
-) -> Result<v8::Local<'scope, v8::Value>, AnyError>
+) -> Result<v8::Local<'scope, v8::Value>, CallbackError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -593,8 +608,10 @@ where
       .parameters
       .into_iter()
       .map(libffi::middle::Type::try_from)
-      .collect::<Result<Vec<_>, _>>()?,
-    libffi::middle::Type::try_from(args.result)?,
+      .collect::<Result<Vec<_>, _>>()
+      .map_err(CallbackError::Other)?,
+    libffi::middle::Type::try_from(args.result)
+      .map_err(CallbackError::Other)?,
   );
 
   // SAFETY: CallbackInfo is leaked, is not null and stays valid as long as the callback exists.
@@ -624,14 +641,16 @@ pub fn op_ffi_unsafe_callback_close(
   state: &mut OpState,
   scope: &mut v8::HandleScope,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
+) -> Result<(), CallbackError> {
   // SAFETY: This drops the closure and the callback info associated with it.
   // Any retained function pointers to the closure become dangling pointers.
   // It is up to the user to know that it is safe to call the `close()` on the
   // UnsafeCallback instance.
   unsafe {
-    let callback_resource =
-      state.resource_table.take::<UnsafeCallbackResource>(rid)?;
+    let callback_resource = state
+      .resource_table
+      .take::<UnsafeCallbackResource>(rid)
+      .map_err(CallbackError::Resource)?;
     let info = Box::from_raw(callback_resource.info);
     let _ = v8::Global::from_raw(scope, info.callback);
     let _ = v8::Global::from_raw(scope, info.context);
diff --git a/ext/ffi/dlfcn.rs b/ext/ffi/dlfcn.rs
index 10199bf858..55909468f8 100644
--- a/ext/ffi/dlfcn.rs
+++ b/ext/ffi/dlfcn.rs
@@ -6,8 +6,6 @@ use crate::symbol::Symbol;
 use crate::turbocall;
 use crate::turbocall::Turbocall;
 use crate::FfiPermissions;
-use deno_core::error::generic_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::v8;
 use deno_core::GarbageCollected;
@@ -21,6 +19,22 @@ use std::collections::HashMap;
 use std::ffi::c_void;
 use std::rc::Rc;
 
+#[derive(Debug, thiserror::Error)]
+pub enum DlfcnError {
+  #[error("Failed to register symbol {symbol}: {error}")]
+  RegisterSymbol {
+    symbol: String,
+    #[source]
+    error: dlopen2::Error,
+  },
+  #[error(transparent)]
+  Dlopen(#[from] dlopen2::Error),
+  #[error(transparent)]
+  Permission(#[from] deno_permissions::PermissionCheckError),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
 pub struct DynamicLibraryResource {
   lib: Library,
   pub symbols: HashMap<String, Box<Symbol>>,
@@ -37,7 +51,7 @@ impl Resource for DynamicLibraryResource {
 }
 
 impl DynamicLibraryResource {
-  pub fn get_static(&self, symbol: String) -> Result<*mut c_void, AnyError> {
+  pub fn get_static(&self, symbol: String) -> Result<*mut c_void, DlfcnError> {
     // By default, Err returned by this function does not tell
     // which symbol wasn't exported. So we'll modify the error
     // message to include the name of symbol.
@@ -45,9 +59,7 @@ impl DynamicLibraryResource {
     // SAFETY: The obtained T symbol is the size of a pointer.
     match unsafe { self.lib.symbol::<*mut c_void>(&symbol) } {
       Ok(value) => Ok(Ok(value)),
-      Err(err) => Err(generic_error(format!(
-        "Failed to register symbol {symbol}: {err}"
-      ))),
+      Err(error) => Err(DlfcnError::RegisterSymbol { symbol, error }),
     }?
   }
 }
@@ -116,7 +128,7 @@ pub fn op_ffi_load<'scope, FP>(
   scope: &mut v8::HandleScope<'scope>,
   state: &mut OpState,
   #[serde] args: FfiLoadArgs,
-) -> Result<v8::Local<'scope, v8::Value>, AnyError>
+) -> Result<v8::Local<'scope, v8::Value>, DlfcnError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -152,15 +164,16 @@ where
           // SAFETY: The obtained T symbol is the size of a pointer.
           match unsafe { resource.lib.symbol::<*const c_void>(symbol) } {
             Ok(value) => Ok(value),
-            Err(err) => if foreign_fn.optional {
+            Err(error) => if foreign_fn.optional {
               let null: v8::Local<v8::Value> = v8::null(scope).into();
               let func_key = v8::String::new(scope, &symbol_key).unwrap();
               obj.set(scope, func_key.into(), null);
               break 'register_symbol;
             } else {
-              Err(generic_error(format!(
-                "Failed to register symbol {symbol}: {err}"
-              )))
+              Err(DlfcnError::RegisterSymbol {
+                symbol: symbol.to_owned(),
+                error,
+              })
             },
           }?;
 
@@ -171,8 +184,13 @@ where
             .clone()
             .into_iter()
             .map(libffi::middle::Type::try_from)
-            .collect::<Result<Vec<_>, _>>()?,
-          foreign_fn.result.clone().try_into()?,
+            .collect::<Result<Vec<_>, _>>()
+            .map_err(DlfcnError::Other)?,
+          foreign_fn
+            .result
+            .clone()
+            .try_into()
+            .map_err(DlfcnError::Other)?,
         );
 
         let func_key = v8::String::new(scope, &symbol_key).unwrap();
diff --git a/ext/ffi/ir.rs b/ext/ffi/ir.rs
index ebf64945b4..2e80842166 100644
--- a/ext/ffi/ir.rs
+++ b/ext/ffi/ir.rs
@@ -1,13 +1,55 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 use crate::symbol::NativeType;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::v8;
 use libffi::middle::Arg;
 use std::ffi::c_void;
 use std::ptr;
 
+#[derive(Debug, thiserror::Error)]
+pub enum IRError {
+  #[error("Invalid FFI u8 type, expected boolean")]
+  InvalidU8ExpectedBoolean,
+  #[error("Invalid FFI u8 type, expected unsigned integer")]
+  InvalidU8ExpectedUnsignedInteger,
+  #[error("Invalid FFI i8 type, expected integer")]
+  InvalidI8,
+  #[error("Invalid FFI u16 type, expected unsigned integer")]
+  InvalidU16,
+  #[error("Invalid FFI i16 type, expected integer")]
+  InvalidI16,
+  #[error("Invalid FFI u32 type, expected unsigned integer")]
+  InvalidU32,
+  #[error("Invalid FFI i32 type, expected integer")]
+  InvalidI32,
+  #[error("Invalid FFI u64 type, expected unsigned integer")]
+  InvalidU64,
+  #[error("Invalid FFI i64 type, expected integer")]
+  InvalidI64,
+  #[error("Invalid FFI usize type, expected unsigned integer")]
+  InvalidUsize,
+  #[error("Invalid FFI isize type, expected integer")]
+  InvalidIsize,
+  #[error("Invalid FFI f32 type, expected number")]
+  InvalidF32,
+  #[error("Invalid FFI f64 type, expected number")]
+  InvalidF64,
+  #[error("Invalid FFI pointer type, expected null, or External")]
+  InvalidPointerType,
+  #[error(
+    "Invalid FFI buffer type, expected null, ArrayBuffer, or ArrayBufferView"
+  )]
+  InvalidBufferType,
+  #[error("Invalid FFI ArrayBufferView, expected data in the buffer")]
+  InvalidArrayBufferView,
+  #[error("Invalid FFI ArrayBuffer, expected data in buffer")]
+  InvalidArrayBuffer,
+  #[error("Invalid FFI struct type, expected ArrayBuffer, or ArrayBufferView")]
+  InvalidStructType,
+  #[error("Invalid FFI function type, expected null, or External")]
+  InvalidFunctionType,
+}
+
 pub struct OutBuffer(pub *mut u8);
 
 // SAFETY: OutBuffer is allocated by us in 00_ffi.js and is guaranteed to be
@@ -126,9 +168,9 @@ unsafe impl Send for NativeValue {}
 #[inline]
 pub fn ffi_parse_bool_arg(
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let bool_value = v8::Local::<v8::Boolean>::try_from(arg)
-    .map_err(|_| type_error("Invalid FFI u8 type, expected boolean"))?
+    .map_err(|_| IRError::InvalidU8ExpectedBoolean)?
     .is_true();
   Ok(NativeValue { bool_value })
 }
@@ -136,9 +178,9 @@ pub fn ffi_parse_bool_arg(
 #[inline]
 pub fn ffi_parse_u8_arg(
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let u8_value = v8::Local::<v8::Uint32>::try_from(arg)
-    .map_err(|_| type_error("Invalid FFI u8 type, expected unsigned integer"))?
+    .map_err(|_| IRError::InvalidU8ExpectedUnsignedInteger)?
     .value() as u8;
   Ok(NativeValue { u8_value })
 }
@@ -146,9 +188,9 @@ pub fn ffi_parse_u8_arg(
 #[inline]
 pub fn ffi_parse_i8_arg(
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let i8_value = v8::Local::<v8::Int32>::try_from(arg)
-    .map_err(|_| type_error("Invalid FFI i8 type, expected integer"))?
+    .map_err(|_| IRError::InvalidI8)?
     .value() as i8;
   Ok(NativeValue { i8_value })
 }
@@ -156,9 +198,9 @@ pub fn ffi_parse_i8_arg(
 #[inline]
 pub fn ffi_parse_u16_arg(
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let u16_value = v8::Local::<v8::Uint32>::try_from(arg)
-    .map_err(|_| type_error("Invalid FFI u16 type, expected unsigned integer"))?
+    .map_err(|_| IRError::InvalidU16)?
     .value() as u16;
   Ok(NativeValue { u16_value })
 }
@@ -166,9 +208,9 @@ pub fn ffi_parse_u16_arg(
 #[inline]
 pub fn ffi_parse_i16_arg(
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let i16_value = v8::Local::<v8::Int32>::try_from(arg)
-    .map_err(|_| type_error("Invalid FFI i16 type, expected integer"))?
+    .map_err(|_| IRError::InvalidI16)?
     .value() as i16;
   Ok(NativeValue { i16_value })
 }
@@ -176,9 +218,9 @@ pub fn ffi_parse_i16_arg(
 #[inline]
 pub fn ffi_parse_u32_arg(
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let u32_value = v8::Local::<v8::Uint32>::try_from(arg)
-    .map_err(|_| type_error("Invalid FFI u32 type, expected unsigned integer"))?
+    .map_err(|_| IRError::InvalidU32)?
     .value();
   Ok(NativeValue { u32_value })
 }
@@ -186,9 +228,9 @@ pub fn ffi_parse_u32_arg(
 #[inline]
 pub fn ffi_parse_i32_arg(
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let i32_value = v8::Local::<v8::Int32>::try_from(arg)
-    .map_err(|_| type_error("Invalid FFI i32 type, expected integer"))?
+    .map_err(|_| IRError::InvalidI32)?
     .value();
   Ok(NativeValue { i32_value })
 }
@@ -197,7 +239,7 @@ pub fn ffi_parse_i32_arg(
 pub fn ffi_parse_u64_arg(
   scope: &mut v8::HandleScope,
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   // Order of checking:
   // 1. BigInt: Uncommon and not supported by Fast API, so optimise slow call for this case.
   // 2. Number: Common, supported by Fast API, so let that be the optimal case.
@@ -207,9 +249,7 @@ pub fn ffi_parse_u64_arg(
   } else if let Ok(value) = v8::Local::<v8::Number>::try_from(arg) {
     value.integer_value(scope).unwrap() as u64
   } else {
-    return Err(type_error(
-      "Invalid FFI u64 type, expected unsigned integer",
-    ));
+    return Err(IRError::InvalidU64);
   };
   Ok(NativeValue { u64_value })
 }
@@ -218,7 +258,7 @@ pub fn ffi_parse_u64_arg(
 pub fn ffi_parse_i64_arg(
   scope: &mut v8::HandleScope,
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   // Order of checking:
   // 1. BigInt: Uncommon and not supported by Fast API, so optimise slow call for this case.
   // 2. Number: Common, supported by Fast API, so let that be the optimal case.
@@ -228,7 +268,7 @@ pub fn ffi_parse_i64_arg(
   } else if let Ok(value) = v8::Local::<v8::Number>::try_from(arg) {
     value.integer_value(scope).unwrap()
   } else {
-    return Err(type_error("Invalid FFI i64 type, expected integer"));
+    return Err(IRError::InvalidI64);
   };
   Ok(NativeValue { i64_value })
 }
@@ -237,7 +277,7 @@ pub fn ffi_parse_i64_arg(
 pub fn ffi_parse_usize_arg(
   scope: &mut v8::HandleScope,
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   // Order of checking:
   // 1. BigInt: Uncommon and not supported by Fast API, so optimise slow call for this case.
   // 2. Number: Common, supported by Fast API, so let that be the optimal case.
@@ -247,7 +287,7 @@ pub fn ffi_parse_usize_arg(
     } else if let Ok(value) = v8::Local::<v8::Number>::try_from(arg) {
       value.integer_value(scope).unwrap() as usize
     } else {
-      return Err(type_error("Invalid FFI usize type, expected integer"));
+      return Err(IRError::InvalidUsize);
     };
   Ok(NativeValue { usize_value })
 }
@@ -256,7 +296,7 @@ pub fn ffi_parse_usize_arg(
 pub fn ffi_parse_isize_arg(
   scope: &mut v8::HandleScope,
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   // Order of checking:
   // 1. BigInt: Uncommon and not supported by Fast API, so optimise slow call for this case.
   // 2. Number: Common, supported by Fast API, so let that be the optimal case.
@@ -266,7 +306,7 @@ pub fn ffi_parse_isize_arg(
     } else if let Ok(value) = v8::Local::<v8::Number>::try_from(arg) {
       value.integer_value(scope).unwrap() as isize
     } else {
-      return Err(type_error("Invalid FFI isize type, expected integer"));
+      return Err(IRError::InvalidIsize);
     };
   Ok(NativeValue { isize_value })
 }
@@ -274,9 +314,9 @@ pub fn ffi_parse_isize_arg(
 #[inline]
 pub fn ffi_parse_f32_arg(
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let f32_value = v8::Local::<v8::Number>::try_from(arg)
-    .map_err(|_| type_error("Invalid FFI f32 type, expected number"))?
+    .map_err(|_| IRError::InvalidF32)?
     .value() as f32;
   Ok(NativeValue { f32_value })
 }
@@ -284,9 +324,9 @@ pub fn ffi_parse_f32_arg(
 #[inline]
 pub fn ffi_parse_f64_arg(
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let f64_value = v8::Local::<v8::Number>::try_from(arg)
-    .map_err(|_| type_error("Invalid FFI f64 type, expected number"))?
+    .map_err(|_| IRError::InvalidF64)?
     .value();
   Ok(NativeValue { f64_value })
 }
@@ -295,15 +335,13 @@ pub fn ffi_parse_f64_arg(
 pub fn ffi_parse_pointer_arg(
   _scope: &mut v8::HandleScope,
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let pointer = if let Ok(value) = v8::Local::<v8::External>::try_from(arg) {
     value.value()
   } else if arg.is_null() {
     ptr::null_mut()
   } else {
-    return Err(type_error(
-      "Invalid FFI pointer type, expected null, or External",
-    ));
+    return Err(IRError::InvalidPointerType);
   };
   Ok(NativeValue { pointer })
 }
@@ -312,7 +350,7 @@ pub fn ffi_parse_pointer_arg(
 pub fn ffi_parse_buffer_arg(
   scope: &mut v8::HandleScope,
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   // Order of checking:
   // 1. ArrayBuffer: Fairly common and not supported by Fast API, optimise this case.
   // 2. ArrayBufferView: Common and supported by Fast API
@@ -328,9 +366,7 @@ pub fn ffi_parse_buffer_arg(
     let byte_offset = value.byte_offset();
     let pointer = value
       .buffer(scope)
-      .ok_or_else(|| {
-        type_error("Invalid FFI ArrayBufferView, expected data in the buffer")
-      })?
+      .ok_or(IRError::InvalidArrayBufferView)?
       .data();
     if let Some(non_null) = pointer {
       // SAFETY: Pointer is non-null, and V8 guarantees that the byte_offset
@@ -342,9 +378,7 @@ pub fn ffi_parse_buffer_arg(
   } else if arg.is_null() {
     ptr::null_mut()
   } else {
-    return Err(type_error(
-      "Invalid FFI buffer type, expected null, ArrayBuffer, or ArrayBufferView",
-    ));
+    return Err(IRError::InvalidBufferType);
   };
   Ok(NativeValue { pointer })
 }
@@ -353,7 +387,7 @@ pub fn ffi_parse_buffer_arg(
 pub fn ffi_parse_struct_arg(
   scope: &mut v8::HandleScope,
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   // Order of checking:
   // 1. ArrayBuffer: Fairly common and not supported by Fast API, optimise this case.
   // 2. ArrayBufferView: Common and supported by Fast API
@@ -362,31 +396,23 @@ pub fn ffi_parse_struct_arg(
     if let Some(non_null) = value.data() {
       non_null.as_ptr()
     } else {
-      return Err(type_error(
-        "Invalid FFI ArrayBuffer, expected data in buffer",
-      ));
+      return Err(IRError::InvalidArrayBuffer);
     }
   } else if let Ok(value) = v8::Local::<v8::ArrayBufferView>::try_from(arg) {
     let byte_offset = value.byte_offset();
     let pointer = value
       .buffer(scope)
-      .ok_or_else(|| {
-        type_error("Invalid FFI ArrayBufferView, expected data in the buffer")
-      })?
+      .ok_or(IRError::InvalidArrayBufferView)?
       .data();
     if let Some(non_null) = pointer {
       // SAFETY: Pointer is non-null, and V8 guarantees that the byte_offset
       // is within the buffer backing store.
       unsafe { non_null.as_ptr().add(byte_offset) }
     } else {
-      return Err(type_error(
-        "Invalid FFI ArrayBufferView, expected data in buffer",
-      ));
+      return Err(IRError::InvalidArrayBufferView);
     }
   } else {
-    return Err(type_error(
-      "Invalid FFI struct type, expected ArrayBuffer, or ArrayBufferView",
-    ));
+    return Err(IRError::InvalidStructType);
   };
   Ok(NativeValue { pointer })
 }
@@ -395,15 +421,13 @@ pub fn ffi_parse_struct_arg(
 pub fn ffi_parse_function_arg(
   _scope: &mut v8::HandleScope,
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let pointer = if let Ok(value) = v8::Local::<v8::External>::try_from(arg) {
     value.value()
   } else if arg.is_null() {
     ptr::null_mut()
   } else {
-    return Err(type_error(
-      "Invalid FFI function type, expected null, or External",
-    ));
+    return Err(IRError::InvalidFunctionType);
   };
   Ok(NativeValue { pointer })
 }
@@ -412,7 +436,7 @@ pub fn ffi_parse_args<'scope>(
   scope: &mut v8::HandleScope<'scope>,
   args: v8::Local<v8::Array>,
   parameter_types: &[NativeType],
-) -> Result<Vec<NativeValue>, AnyError>
+) -> Result<Vec<NativeValue>, IRError>
 where
   'scope: 'scope,
 {
diff --git a/ext/ffi/lib.rs b/ext/ffi/lib.rs
index 77ec3c85e3..73ec7757ab 100644
--- a/ext/ffi/lib.rs
+++ b/ext/ffi/lib.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
-
 use std::mem::size_of;
 use std::os::raw::c_char;
 use std::os::raw::c_short;
@@ -29,6 +27,14 @@ use repr::*;
 use symbol::NativeType;
 use symbol::Symbol;
 
+pub use call::CallError;
+pub use callback::CallbackError;
+use deno_permissions::PermissionCheckError;
+pub use dlfcn::DlfcnError;
+pub use ir::IRError;
+pub use r#static::StaticError;
+pub use repr::ReprError;
+
 #[cfg(not(target_pointer_width = "64"))]
 compile_error!("platform not supported");
 
@@ -41,17 +47,17 @@ const _: () = {
 pub const UNSTABLE_FEATURE_NAME: &str = "ffi";
 
 pub trait FfiPermissions {
-  fn check_partial_no_path(&mut self) -> Result<(), AnyError>;
+  fn check_partial_no_path(&mut self) -> Result<(), PermissionCheckError>;
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
   fn check_partial_with_path(
     &mut self,
     path: &str,
-  ) -> Result<PathBuf, AnyError>;
+  ) -> Result<PathBuf, PermissionCheckError>;
 }
 
 impl FfiPermissions for deno_permissions::PermissionsContainer {
   #[inline(always)]
-  fn check_partial_no_path(&mut self) -> Result<(), AnyError> {
+  fn check_partial_no_path(&mut self) -> Result<(), PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_ffi_partial_no_path(self)
   }
 
@@ -59,7 +65,7 @@ impl FfiPermissions for deno_permissions::PermissionsContainer {
   fn check_partial_with_path(
     &mut self,
     path: &str,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_ffi_partial_with_path(
       self, path,
     )
diff --git a/ext/ffi/repr.rs b/ext/ffi/repr.rs
index 315e6d53bc..fd8a2c8e70 100644
--- a/ext/ffi/repr.rs
+++ b/ext/ffi/repr.rs
@@ -1,9 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 use crate::FfiPermissions;
-use deno_core::error::range_error;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::v8;
 use deno_core::OpState;
@@ -12,11 +9,51 @@ use std::ffi::c_void;
 use std::ffi::CStr;
 use std::ptr;
 
+#[derive(Debug, thiserror::Error)]
+pub enum ReprError {
+  #[error("Invalid pointer to offset, pointer is null")]
+  InvalidOffset,
+  #[error("Invalid ArrayBuffer pointer, pointer is null")]
+  InvalidArrayBuffer,
+  #[error("Destination length is smaller than source length")]
+  DestinationLengthTooShort,
+  #[error("Invalid CString pointer, pointer is null")]
+  InvalidCString,
+  #[error("Invalid CString pointer, string exceeds max length")]
+  CStringTooLong,
+  #[error("Invalid bool pointer, pointer is null")]
+  InvalidBool,
+  #[error("Invalid u8 pointer, pointer is null")]
+  InvalidU8,
+  #[error("Invalid i8 pointer, pointer is null")]
+  InvalidI8,
+  #[error("Invalid u16 pointer, pointer is null")]
+  InvalidU16,
+  #[error("Invalid i16 pointer, pointer is null")]
+  InvalidI16,
+  #[error("Invalid u32 pointer, pointer is null")]
+  InvalidU32,
+  #[error("Invalid i32 pointer, pointer is null")]
+  InvalidI32,
+  #[error("Invalid u64 pointer, pointer is null")]
+  InvalidU64,
+  #[error("Invalid i64 pointer, pointer is null")]
+  InvalidI64,
+  #[error("Invalid f32 pointer, pointer is null")]
+  InvalidF32,
+  #[error("Invalid f64 pointer, pointer is null")]
+  InvalidF64,
+  #[error("Invalid pointer pointer, pointer is null")]
+  InvalidPointer,
+  #[error(transparent)]
+  Permission(#[from] deno_permissions::PermissionCheckError),
+}
+
 #[op2(fast)]
 pub fn op_ffi_ptr_create<FP>(
   state: &mut OpState,
   #[bigint] ptr_number: usize,
-) -> Result<*mut c_void, AnyError>
+) -> Result<*mut c_void, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -31,7 +68,7 @@ pub fn op_ffi_ptr_equals<FP>(
   state: &mut OpState,
   a: *const c_void,
   b: *const c_void,
-) -> Result<bool, AnyError>
+) -> Result<bool, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -45,7 +82,7 @@ where
 pub fn op_ffi_ptr_of<FP>(
   state: &mut OpState,
   #[anybuffer] buf: *const u8,
-) -> Result<*mut c_void, AnyError>
+) -> Result<*mut c_void, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -59,7 +96,7 @@ where
 pub fn op_ffi_ptr_of_exact<FP>(
   state: &mut OpState,
   buf: v8::Local<v8::ArrayBufferView>,
-) -> Result<*mut c_void, AnyError>
+) -> Result<*mut c_void, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -80,7 +117,7 @@ pub fn op_ffi_ptr_offset<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<*mut c_void, AnyError>
+) -> Result<*mut c_void, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -88,7 +125,7 @@ where
   permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid pointer to offset, pointer is null"));
+    return Err(ReprError::InvalidOffset);
   }
 
   // TODO(mmastrac): Create a RawPointer that can safely do pointer math.
@@ -110,7 +147,7 @@ unsafe extern "C" fn noop_deleter_callback(
 pub fn op_ffi_ptr_value<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
-) -> Result<usize, AnyError>
+) -> Result<usize, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -127,7 +164,7 @@ pub fn op_ffi_get_buf<FP, 'scope>(
   ptr: *mut c_void,
   #[number] offset: isize,
   #[number] len: usize,
-) -> Result<v8::Local<'scope, v8::ArrayBuffer>, AnyError>
+) -> Result<v8::Local<'scope, v8::ArrayBuffer>, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -135,7 +172,7 @@ where
   permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid ArrayBuffer pointer, pointer is null"));
+    return Err(ReprError::InvalidArrayBuffer);
   }
 
   // SAFETY: Trust the user to have provided a real pointer, offset, and a valid matching size to it. Since this is a foreign pointer, we should not do any deletion.
@@ -144,7 +181,7 @@ where
       ptr.offset(offset),
       len,
       noop_deleter_callback,
-      std::ptr::null_mut(),
+      ptr::null_mut(),
     )
   }
   .make_shared();
@@ -159,7 +196,7 @@ pub fn op_ffi_buf_copy_into<FP>(
   #[number] offset: isize,
   #[anybuffer] dst: &mut [u8],
   #[number] len: usize,
-) -> Result<(), AnyError>
+) -> Result<(), ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -167,11 +204,9 @@ where
   permissions.check_partial_no_path()?;
 
   if src.is_null() {
-    Err(type_error("Invalid ArrayBuffer pointer, pointer is null"))
+    Err(ReprError::InvalidArrayBuffer)
   } else if dst.len() < len {
-    Err(range_error(
-      "Destination length is smaller than source length",
-    ))
+    Err(ReprError::DestinationLengthTooShort)
   } else {
     let src = src as *const c_void;
 
@@ -190,7 +225,7 @@ pub fn op_ffi_cstr_read<FP, 'scope>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<v8::Local<'scope, v8::String>, AnyError>
+) -> Result<v8::Local<'scope, v8::String>, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -198,16 +233,14 @@ where
   permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid CString pointer, pointer is null"));
+    return Err(ReprError::InvalidCString);
   }
 
   let cstr =
   // SAFETY: Pointer and offset are user provided.
     unsafe { CStr::from_ptr(ptr.offset(offset) as *const c_char) }.to_bytes();
   let value = v8::String::new_from_utf8(scope, cstr, v8::NewStringType::Normal)
-    .ok_or_else(|| {
-      type_error("Invalid CString pointer, string exceeds max length")
-    })?;
+    .ok_or_else(|| ReprError::CStringTooLong)?;
   Ok(value)
 }
 
@@ -216,7 +249,7 @@ pub fn op_ffi_read_bool<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<bool, AnyError>
+) -> Result<bool, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -224,7 +257,7 @@ where
   permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid bool pointer, pointer is null"));
+    return Err(ReprError::InvalidBool);
   }
 
   // SAFETY: ptr and offset are user provided.
@@ -236,7 +269,7 @@ pub fn op_ffi_read_u8<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<u32, AnyError>
+) -> Result<u32, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -244,7 +277,7 @@ where
   permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid u8 pointer, pointer is null"));
+    return Err(ReprError::InvalidU8);
   }
 
   // SAFETY: ptr and offset are user provided.
@@ -258,7 +291,7 @@ pub fn op_ffi_read_i8<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<i32, AnyError>
+) -> Result<i32, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -266,7 +299,7 @@ where
   permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid i8 pointer, pointer is null"));
+    return Err(ReprError::InvalidI8);
   }
 
   // SAFETY: ptr and offset are user provided.
@@ -280,7 +313,7 @@ pub fn op_ffi_read_u16<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<u32, AnyError>
+) -> Result<u32, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -288,7 +321,7 @@ where
   permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid u16 pointer, pointer is null"));
+    return Err(ReprError::InvalidU16);
   }
 
   // SAFETY: ptr and offset are user provided.
@@ -302,7 +335,7 @@ pub fn op_ffi_read_i16<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<i32, AnyError>
+) -> Result<i32, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -310,7 +343,7 @@ where
   permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid i16 pointer, pointer is null"));
+    return Err(ReprError::InvalidI16);
   }
 
   // SAFETY: ptr and offset are user provided.
@@ -324,7 +357,7 @@ pub fn op_ffi_read_u32<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<u32, AnyError>
+) -> Result<u32, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -332,7 +365,7 @@ where
   permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid u32 pointer, pointer is null"));
+    return Err(ReprError::InvalidU32);
   }
 
   // SAFETY: ptr and offset are user provided.
@@ -344,7 +377,7 @@ pub fn op_ffi_read_i32<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<i32, AnyError>
+) -> Result<i32, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -352,7 +385,7 @@ where
   permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid i32 pointer, pointer is null"));
+    return Err(ReprError::InvalidI32);
   }
 
   // SAFETY: ptr and offset are user provided.
@@ -367,7 +400,7 @@ pub fn op_ffi_read_u64<FP>(
   // Note: The representation of 64-bit integers is function-wide. We cannot
   // choose to take this parameter as a number while returning a bigint.
   #[bigint] offset: isize,
-) -> Result<u64, AnyError>
+) -> Result<u64, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -375,7 +408,7 @@ where
   permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid u64 pointer, pointer is null"));
+    return Err(ReprError::InvalidU64);
   }
 
   let value =
@@ -393,7 +426,7 @@ pub fn op_ffi_read_i64<FP>(
   // Note: The representation of 64-bit integers is function-wide. We cannot
   // choose to take this parameter as a number while returning a bigint.
   #[bigint] offset: isize,
-) -> Result<i64, AnyError>
+) -> Result<i64, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -401,7 +434,7 @@ where
   permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid i64 pointer, pointer is null"));
+    return Err(ReprError::InvalidI64);
   }
 
   let value =
@@ -416,7 +449,7 @@ pub fn op_ffi_read_f32<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<f32, AnyError>
+) -> Result<f32, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -424,7 +457,7 @@ where
   permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid f32 pointer, pointer is null"));
+    return Err(ReprError::InvalidF32);
   }
 
   // SAFETY: ptr and offset are user provided.
@@ -436,7 +469,7 @@ pub fn op_ffi_read_f64<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<f64, AnyError>
+) -> Result<f64, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -444,7 +477,7 @@ where
   permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid f64 pointer, pointer is null"));
+    return Err(ReprError::InvalidF64);
   }
 
   // SAFETY: ptr and offset are user provided.
@@ -456,7 +489,7 @@ pub fn op_ffi_read_ptr<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<*mut c_void, AnyError>
+) -> Result<*mut c_void, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
@@ -464,7 +497,7 @@ where
   permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid pointer pointer, pointer is null"));
+    return Err(ReprError::InvalidPointer);
   }
 
   // SAFETY: ptr and offset are user provided.
diff --git a/ext/ffi/static.rs b/ext/ffi/static.rs
index f08605754b..61b4059336 100644
--- a/ext/ffi/static.rs
+++ b/ext/ffi/static.rs
@@ -2,14 +2,24 @@
 
 use crate::dlfcn::DynamicLibraryResource;
 use crate::symbol::NativeType;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::v8;
 use deno_core::OpState;
 use deno_core::ResourceId;
 use std::ptr;
 
+#[derive(Debug, thiserror::Error)]
+pub enum StaticError {
+  #[error(transparent)]
+  Dlfcn(super::DlfcnError),
+  #[error("Invalid FFI static type 'void'")]
+  InvalidTypeVoid,
+  #[error("Invalid FFI static type 'struct'")]
+  InvalidTypeStruct,
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+}
+
 #[op2]
 pub fn op_ffi_get_static<'scope>(
   scope: &mut v8::HandleScope<'scope>,
@@ -18,24 +28,27 @@ pub fn op_ffi_get_static<'scope>(
   #[string] name: String,
   #[serde] static_type: NativeType,
   optional: bool,
-) -> Result<v8::Local<'scope, v8::Value>, AnyError> {
-  let resource = state.resource_table.get::<DynamicLibraryResource>(rid)?;
+) -> Result<v8::Local<'scope, v8::Value>, StaticError> {
+  let resource = state
+    .resource_table
+    .get::<DynamicLibraryResource>(rid)
+    .map_err(StaticError::Resource)?;
 
   let data_ptr = match resource.get_static(name) {
-    Ok(data_ptr) => Ok(data_ptr),
+    Ok(data_ptr) => data_ptr,
     Err(err) => {
       if optional {
         let null: v8::Local<v8::Value> = v8::null(scope).into();
         return Ok(null);
       } else {
-        Err(err)
+        return Err(StaticError::Dlfcn(err));
       }
     }
-  }?;
+  };
 
   Ok(match static_type {
     NativeType::Void => {
-      return Err(type_error("Invalid FFI static type 'void'"));
+      return Err(StaticError::InvalidTypeVoid);
     }
     NativeType::Bool => {
       // SAFETY: ptr is user provided
@@ -132,7 +145,7 @@ pub fn op_ffi_get_static<'scope>(
       external
     }
     NativeType::Struct(_) => {
-      return Err(type_error("Invalid FFI static type 'struct'"));
+      return Err(StaticError::InvalidTypeStruct);
     }
   })
 }
diff --git a/ext/fs/30_fs.js b/ext/fs/30_fs.js
index 0ee1ba82c7..fc2b18be13 100644
--- a/ext/fs/30_fs.js
+++ b/ext/fs/30_fs.js
@@ -346,9 +346,10 @@ const { 0: statStruct, 1: statBuf } = createByteStruct({
   mtime: "date",
   atime: "date",
   birthtime: "date",
+  ctime: "date",
   dev: "u64",
   ino: "?u64",
-  mode: "?u64",
+  mode: "u64",
   nlink: "?u64",
   uid: "?u64",
   gid: "?u64",
@@ -377,9 +378,10 @@ function parseFileInfo(response) {
     birthtime: response.birthtimeSet === true
       ? new Date(response.birthtime)
       : null,
+    ctime: response.ctimeSet === true ? new Date(response.ctime) : null,
     dev: response.dev,
+    mode: response.mode,
     ino: unix ? response.ino : null,
-    mode: unix ? response.mode : null,
     nlink: unix ? response.nlink : null,
     uid: unix ? response.uid : null,
     gid: unix ? response.gid : null,
diff --git a/ext/fs/Cargo.toml b/ext/fs/Cargo.toml
index 894b307efa..e85f349b15 100644
--- a/ext/fs/Cargo.toml
+++ b/ext/fs/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_fs"
-version = "0.78.0"
+version = "0.87.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -21,15 +21,17 @@ async-trait.workspace = true
 base32.workspace = true
 deno_core.workspace = true
 deno_io.workspace = true
+deno_path_util.workspace = true
 deno_permissions.workspace = true
 filetime.workspace = true
 libc.workspace = true
 rand.workspace = true
 rayon = "1.8.0"
 serde.workspace = true
+thiserror.workspace = true
 
 [target.'cfg(unix)'.dependencies]
-nix.workspace = true
+nix = { workspace = true, features = ["fs", "user"] }
 
 [target.'cfg(windows)'.dependencies]
 winapi = { workspace = true, features = ["winbase"] }
diff --git a/ext/fs/in_memory_fs.rs b/ext/fs/in_memory_fs.rs
index 027539e849..34b77836d9 100644
--- a/ext/fs/in_memory_fs.rs
+++ b/ext/fs/in_memory_fs.rs
@@ -12,12 +12,12 @@ use std::path::PathBuf;
 use std::rc::Rc;
 use std::sync::Arc;
 
-use deno_core::normalize_path;
 use deno_core::parking_lot::Mutex;
 use deno_io::fs::File;
 use deno_io::fs::FsError;
 use deno_io::fs::FsResult;
 use deno_io::fs::FsStat;
+use deno_path_util::normalize_path;
 
 use crate::interface::AccessCheckCb;
 use crate::interface::FsDirEntry;
@@ -44,7 +44,7 @@ impl InMemoryFs {
   pub fn setup_text_files(&self, files: Vec<(String, String)>) {
     for (path, text) in files {
       let path = PathBuf::from(path);
-      self.mkdir_sync(path.parent().unwrap(), true, 0).unwrap();
+      self.mkdir_sync(path.parent().unwrap(), true, None).unwrap();
       self
         .write_file_sync(
           &path,
@@ -101,7 +101,7 @@ impl FileSystem for InMemoryFs {
     &self,
     path: &Path,
     recursive: bool,
-    _mode: u32,
+    _mode: Option<u32>,
   ) -> FsResult<()> {
     let path = normalize_path(path);
 
@@ -119,7 +119,7 @@ impl FileSystem for InMemoryFs {
         },
         None => {
           if recursive {
-            self.mkdir_sync(parent, true, 0)?;
+            self.mkdir_sync(parent, true, None)?;
           } else {
             return Err(FsError::Io(Error::new(
               ErrorKind::NotFound,
@@ -149,7 +149,7 @@ impl FileSystem for InMemoryFs {
     &self,
     path: PathBuf,
     recursive: bool,
-    mode: u32,
+    mode: Option<u32>,
   ) -> FsResult<()> {
     self.mkdir_sync(&path, recursive, mode)
   }
@@ -229,6 +229,7 @@ impl FileSystem for InMemoryFs {
           mtime: None,
           atime: None,
           birthtime: None,
+          ctime: None,
           dev: 0,
           ino: 0,
           mode: 0,
@@ -251,6 +252,7 @@ impl FileSystem for InMemoryFs {
           mtime: None,
           atime: None,
           birthtime: None,
+          ctime: None,
           dev: 0,
           ino: 0,
           mode: 0,
diff --git a/ext/fs/interface.rs b/ext/fs/interface.rs
index af4beb248b..73333b0fd1 100644
--- a/ext/fs/interface.rs
+++ b/ext/fs/interface.rs
@@ -121,13 +121,17 @@ pub trait FileSystem: std::fmt::Debug + MaybeSend + MaybeSync {
     access_check: Option<AccessCheckCb<'a>>,
   ) -> FsResult<Rc<dyn File>>;
 
-  fn mkdir_sync(&self, path: &Path, recursive: bool, mode: u32)
-    -> FsResult<()>;
+  fn mkdir_sync(
+    &self,
+    path: &Path,
+    recursive: bool,
+    mode: Option<u32>,
+  ) -> FsResult<()>;
   async fn mkdir_async(
     &self,
     path: PathBuf,
     recursive: bool,
-    mode: u32,
+    mode: Option<u32>,
   ) -> FsResult<()>;
 
   fn chmod_sync(&self, path: &Path, mode: u32) -> FsResult<()>;
diff --git a/ext/fs/lib.rs b/ext/fs/lib.rs
index bd49078b2e..dd852e6be8 100644
--- a/ext/fs/lib.rs
+++ b/ext/fs/lib.rs
@@ -14,14 +14,16 @@ pub use crate::interface::FileSystemRc;
 pub use crate::interface::FsDirEntry;
 pub use crate::interface::FsFileType;
 pub use crate::interface::OpenOptions;
+pub use crate::ops::FsOpsError;
+pub use crate::ops::OperationError;
 pub use crate::std_fs::RealFs;
 pub use crate::sync::MaybeSend;
 pub use crate::sync::MaybeSync;
 
 use crate::ops::*;
 
-use deno_core::error::AnyError;
 use deno_io::fs::FsError;
+use deno_permissions::PermissionCheckError;
 use std::borrow::Cow;
 use std::path::Path;
 use std::path::PathBuf;
@@ -40,45 +42,51 @@ pub trait FsPermissions {
     &mut self,
     path: &str,
     api_name: &str,
-  ) -> Result<PathBuf, AnyError>;
+  ) -> Result<PathBuf, PermissionCheckError>;
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
   fn check_read_path<'a>(
     &mut self,
     path: &'a Path,
     api_name: &str,
-  ) -> Result<Cow<'a, Path>, AnyError>;
-  fn check_read_all(&mut self, api_name: &str) -> Result<(), AnyError>;
+  ) -> Result<Cow<'a, Path>, PermissionCheckError>;
+  fn check_read_all(
+    &mut self,
+    api_name: &str,
+  ) -> Result<(), PermissionCheckError>;
   fn check_read_blind(
     &mut self,
     p: &Path,
     display: &str,
     api_name: &str,
-  ) -> Result<(), AnyError>;
+  ) -> Result<(), PermissionCheckError>;
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
   fn check_write(
     &mut self,
     path: &str,
     api_name: &str,
-  ) -> Result<PathBuf, AnyError>;
+  ) -> Result<PathBuf, PermissionCheckError>;
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
   fn check_write_path<'a>(
     &mut self,
     path: &'a Path,
     api_name: &str,
-  ) -> Result<Cow<'a, Path>, AnyError>;
+  ) -> Result<Cow<'a, Path>, PermissionCheckError>;
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
   fn check_write_partial(
     &mut self,
     path: &str,
     api_name: &str,
-  ) -> Result<PathBuf, AnyError>;
-  fn check_write_all(&mut self, api_name: &str) -> Result<(), AnyError>;
+  ) -> Result<PathBuf, PermissionCheckError>;
+  fn check_write_all(
+    &mut self,
+    api_name: &str,
+  ) -> Result<(), PermissionCheckError>;
   fn check_write_blind(
     &mut self,
     p: &Path,
     display: &str,
     api_name: &str,
-  ) -> Result<(), AnyError>;
+  ) -> Result<(), PermissionCheckError>;
 
   fn check<'a>(
     &mut self,
@@ -138,7 +146,7 @@ impl FsPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     path: &str,
     api_name: &str,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_read(self, path, api_name)
   }
 
@@ -146,7 +154,7 @@ impl FsPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     path: &'a Path,
     api_name: &str,
-  ) -> Result<Cow<'a, Path>, AnyError> {
+  ) -> Result<Cow<'a, Path>, PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_read_path(
       self,
       path,
@@ -158,7 +166,7 @@ impl FsPermissions for deno_permissions::PermissionsContainer {
     path: &Path,
     display: &str,
     api_name: &str,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_read_blind(
       self, path, display, api_name,
     )
@@ -168,7 +176,7 @@ impl FsPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     path: &str,
     api_name: &str,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_write(self, path, api_name)
   }
 
@@ -176,7 +184,7 @@ impl FsPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     path: &'a Path,
     api_name: &str,
-  ) -> Result<Cow<'a, Path>, AnyError> {
+  ) -> Result<Cow<'a, Path>, PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_write_path(
       self, path, api_name,
     )
@@ -186,7 +194,7 @@ impl FsPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     path: &str,
     api_name: &str,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_write_partial(
       self, path, api_name,
     )
@@ -197,17 +205,23 @@ impl FsPermissions for deno_permissions::PermissionsContainer {
     p: &Path,
     display: &str,
     api_name: &str,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_write_blind(
       self, p, display, api_name,
     )
   }
 
-  fn check_read_all(&mut self, api_name: &str) -> Result<(), AnyError> {
+  fn check_read_all(
+    &mut self,
+    api_name: &str,
+  ) -> Result<(), PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_read_all(self, api_name)
   }
 
-  fn check_write_all(&mut self, api_name: &str) -> Result<(), AnyError> {
+  fn check_write_all(
+    &mut self,
+    api_name: &str,
+  ) -> Result<(), PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_write_all(self, api_name)
   }
 }
diff --git a/ext/fs/ops.rs b/ext/fs/ops.rs
index 150d3b9555..3d0d96ce66 100644
--- a/ext/fs/ops.rs
+++ b/ext/fs/ops.rs
@@ -1,6 +1,8 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 use std::cell::RefCell;
+use std::error::Error;
+use std::fmt::Formatter;
 use std::io;
 use std::io::SeekFrom;
 use std::path::Path;
@@ -8,10 +10,12 @@ use std::path::PathBuf;
 use std::path::StripPrefixError;
 use std::rc::Rc;
 
-use deno_core::anyhow::bail;
-use deno_core::error::custom_error;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
+use crate::interface::AccessCheckFn;
+use crate::interface::FileSystemRc;
+use crate::interface::FsDirEntry;
+use crate::interface::FsFileType;
+use crate::FsPermissions;
+use crate::OpenOptions;
 use deno_core::op2;
 use deno_core::CancelFuture;
 use deno_core::CancelHandle;
@@ -22,17 +26,72 @@ use deno_core::ToJsBuffer;
 use deno_io::fs::FileResource;
 use deno_io::fs::FsError;
 use deno_io::fs::FsStat;
+use deno_permissions::PermissionCheckError;
 use rand::rngs::ThreadRng;
 use rand::thread_rng;
 use rand::Rng;
 use serde::Serialize;
 
-use crate::interface::AccessCheckFn;
-use crate::interface::FileSystemRc;
-use crate::interface::FsDirEntry;
-use crate::interface::FsFileType;
-use crate::FsPermissions;
-use crate::OpenOptions;
+#[derive(Debug, thiserror::Error)]
+pub enum FsOpsError {
+  #[error("{0}")]
+  Io(#[source] std::io::Error),
+  #[error("{0}")]
+  OperationError(#[source] OperationError),
+  #[error(transparent)]
+  Permission(#[from] PermissionCheckError),
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("File name or path {0:?} is not valid UTF-8")]
+  InvalidUtf8(std::ffi::OsString),
+  #[error("{0}")]
+  StripPrefix(#[from] StripPrefixError),
+  #[error("{0}")]
+  Canceled(#[from] deno_core::Canceled),
+  #[error("Invalid seek mode: {0}")]
+  InvalidSeekMode(i32),
+  #[error("Invalid control character in prefix or suffix: {0:?}")]
+  InvalidControlCharacter(String),
+  #[error("Invalid character in prefix or suffix: {0:?}")]
+  InvalidCharacter(String),
+  #[cfg(windows)]
+  #[error("Invalid trailing character in suffix")]
+  InvalidTrailingCharacter,
+  #[error("Requires {err} access to {path}, {}", print_not_capable_info(*.standalone, .err))]
+  NotCapableAccess {
+    // NotCapable
+    standalone: bool,
+    err: &'static str,
+    path: String,
+  },
+  #[error("permission denied: {0}")]
+  NotCapable(&'static str), // NotCapable
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
+impl From<FsError> for FsOpsError {
+  fn from(err: FsError) -> Self {
+    match err {
+      FsError::Io(err) => FsOpsError::Io(err),
+      FsError::FileBusy => {
+        FsOpsError::Other(deno_core::error::resource_unavailable())
+      }
+      FsError::NotSupported => {
+        FsOpsError::Other(deno_core::error::not_supported())
+      }
+      FsError::NotCapable(err) => FsOpsError::NotCapable(err),
+    }
+  }
+}
+
+fn print_not_capable_info(standalone: bool, err: &'static str) -> String {
+  if standalone {
+    format!("specify the required permissions during compilation using `deno compile --allow-{err}`")
+  } else {
+    format!("run again with the --allow-{err} flag")
+  }
+}
 
 fn sync_permission_check<'a, P: FsPermissions + 'static>(
   permissions: &'a mut P,
@@ -58,7 +117,7 @@ fn map_permission_error(
   operation: &'static str,
   error: FsError,
   path: &Path,
-) -> AnyError {
+) -> FsOpsError {
   match error {
     FsError::NotCapable(err) => {
       let path = format!("{path:?}");
@@ -67,14 +126,12 @@ fn map_permission_error(
       } else {
         (path.as_str(), "")
       };
-      let msg = if deno_permissions::is_standalone() {
-        format!(
-          "Requires {err} access to {path}{truncated}, specify the required permissions during compilation using `deno compile --allow-{err}`")
-      } else {
-        format!(
-          "Requires {err} access to {path}{truncated}, run again with the --allow-{err} flag")
-      };
-      custom_error("NotCapable", msg)
+
+      FsOpsError::NotCapableAccess {
+        standalone: deno_permissions::is_standalone(),
+        err,
+        path: format!("{path}{truncated}"),
+      }
     }
     err => Err::<(), _>(err)
       .context_path(operation, path)
@@ -85,7 +142,7 @@ fn map_permission_error(
 
 #[op2]
 #[string]
-pub fn op_fs_cwd<P>(state: &mut OpState) -> Result<String, AnyError>
+pub fn op_fs_cwd<P>(state: &mut OpState) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -102,7 +159,7 @@ where
 pub fn op_fs_chdir<P>(
   state: &mut OpState,
   #[string] directory: &str,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -119,7 +176,7 @@ where
 pub fn op_fs_umask(
   state: &mut OpState,
   mask: Option<u32>,
-) -> Result<u32, AnyError>
+) -> Result<u32, FsOpsError>
 where
 {
   state.borrow::<FileSystemRc>().umask(mask).context("umask")
@@ -131,7 +188,7 @@ pub fn op_fs_open_sync<P>(
   state: &mut OpState,
   #[string] path: String,
   #[serde] options: Option<OpenOptions>,
-) -> Result<ResourceId, AnyError>
+) -> Result<ResourceId, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -158,7 +215,7 @@ pub async fn op_fs_open_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
   #[serde] options: Option<OpenOptions>,
-) -> Result<ResourceId, AnyError>
+) -> Result<ResourceId, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -186,7 +243,7 @@ pub fn op_fs_mkdir_sync<P>(
   #[string] path: String,
   recursive: bool,
   mode: Option<u32>,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -197,7 +254,7 @@ where
     .check_write(&path, "Deno.mkdirSync()")?;
 
   let fs = state.borrow::<FileSystemRc>();
-  fs.mkdir_sync(&path, recursive, mode)
+  fs.mkdir_sync(&path, recursive, Some(mode))
     .context_path("mkdir", &path)?;
 
   Ok(())
@@ -209,7 +266,7 @@ pub async fn op_fs_mkdir_async<P>(
   #[string] path: String,
   recursive: bool,
   mode: Option<u32>,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -221,7 +278,7 @@ where
     (state.borrow::<FileSystemRc>().clone(), path)
   };
 
-  fs.mkdir_async(path.clone(), recursive, mode)
+  fs.mkdir_async(path.clone(), recursive, Some(mode))
     .await
     .context_path("mkdir", &path)?;
 
@@ -233,7 +290,7 @@ pub fn op_fs_chmod_sync<P>(
   state: &mut OpState,
   #[string] path: String,
   mode: u32,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -250,7 +307,7 @@ pub async fn op_fs_chmod_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
   mode: u32,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -271,7 +328,7 @@ pub fn op_fs_chown_sync<P>(
   #[string] path: String,
   uid: Option<u32>,
   gid: Option<u32>,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -290,7 +347,7 @@ pub async fn op_fs_chown_async<P>(
   #[string] path: String,
   uid: Option<u32>,
   gid: Option<u32>,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -310,7 +367,7 @@ pub fn op_fs_remove_sync<P>(
   state: &mut OpState,
   #[string] path: &str,
   recursive: bool,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -330,7 +387,7 @@ pub async fn op_fs_remove_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
   recursive: bool,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -361,7 +418,7 @@ pub fn op_fs_copy_file_sync<P>(
   state: &mut OpState,
   #[string] from: &str,
   #[string] to: &str,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -381,7 +438,7 @@ pub async fn op_fs_copy_file_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] from: String,
   #[string] to: String,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -405,7 +462,7 @@ pub fn op_fs_stat_sync<P>(
   state: &mut OpState,
   #[string] path: String,
   #[buffer] stat_out_buf: &mut [u32],
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -424,7 +481,7 @@ where
 pub async fn op_fs_stat_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
-) -> Result<SerializableStat, AnyError>
+) -> Result<SerializableStat, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -446,7 +503,7 @@ pub fn op_fs_lstat_sync<P>(
   state: &mut OpState,
   #[string] path: String,
   #[buffer] stat_out_buf: &mut [u32],
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -465,7 +522,7 @@ where
 pub async fn op_fs_lstat_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
-) -> Result<SerializableStat, AnyError>
+) -> Result<SerializableStat, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -487,7 +544,7 @@ where
 pub fn op_fs_realpath_sync<P>(
   state: &mut OpState,
   #[string] path: String,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -510,7 +567,7 @@ where
 pub async fn op_fs_realpath_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -538,7 +595,7 @@ where
 pub fn op_fs_read_dir_sync<P>(
   state: &mut OpState,
   #[string] path: String,
-) -> Result<Vec<FsDirEntry>, AnyError>
+) -> Result<Vec<FsDirEntry>, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -557,7 +614,7 @@ where
 pub async fn op_fs_read_dir_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
-) -> Result<Vec<FsDirEntry>, AnyError>
+) -> Result<Vec<FsDirEntry>, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -582,7 +639,7 @@ pub fn op_fs_rename_sync<P>(
   state: &mut OpState,
   #[string] oldpath: String,
   #[string] newpath: String,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -603,7 +660,7 @@ pub async fn op_fs_rename_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] oldpath: String,
   #[string] newpath: String,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -628,7 +685,7 @@ pub fn op_fs_link_sync<P>(
   state: &mut OpState,
   #[string] oldpath: &str,
   #[string] newpath: &str,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -650,7 +707,7 @@ pub async fn op_fs_link_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] oldpath: String,
   #[string] newpath: String,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -677,7 +734,7 @@ pub fn op_fs_symlink_sync<P>(
   #[string] oldpath: &str,
   #[string] newpath: &str,
   #[serde] file_type: Option<FsFileType>,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -701,7 +758,7 @@ pub async fn op_fs_symlink_async<P>(
   #[string] oldpath: String,
   #[string] newpath: String,
   #[serde] file_type: Option<FsFileType>,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -728,7 +785,7 @@ where
 pub fn op_fs_read_link_sync<P>(
   state: &mut OpState,
   #[string] path: String,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -748,7 +805,7 @@ where
 pub async fn op_fs_read_link_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -773,7 +830,7 @@ pub fn op_fs_truncate_sync<P>(
   state: &mut OpState,
   #[string] path: &str,
   #[number] len: u64,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -793,7 +850,7 @@ pub async fn op_fs_truncate_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
   #[number] len: u64,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -820,7 +877,7 @@ pub fn op_fs_utime_sync<P>(
   #[smi] atime_nanos: u32,
   #[number] mtime_secs: i64,
   #[smi] mtime_nanos: u32,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -841,7 +898,7 @@ pub async fn op_fs_utime_async<P>(
   #[smi] atime_nanos: u32,
   #[number] mtime_secs: i64,
   #[smi] mtime_nanos: u32,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -871,7 +928,7 @@ pub fn op_fs_make_temp_dir_sync<P>(
   #[string] dir_arg: Option<String>,
   #[string] prefix: Option<String>,
   #[string] suffix: Option<String>,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -886,7 +943,7 @@ where
   const MAX_TRIES: u32 = 10;
   for _ in 0..MAX_TRIES {
     let path = tmp_name(&mut rng, &dir, prefix.as_deref(), suffix.as_deref())?;
-    match fs.mkdir_sync(&path, false, 0o700) {
+    match fs.mkdir_sync(&path, false, Some(0o700)) {
       Ok(_) => {
         // PERMISSIONS: ensure the absolute path is not leaked
         let path = strip_dir_prefix(&dir, dir_arg.as_deref(), path)?;
@@ -913,7 +970,7 @@ pub async fn op_fs_make_temp_dir_async<P>(
   #[string] dir_arg: Option<String>,
   #[string] prefix: Option<String>,
   #[string] suffix: Option<String>,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -928,7 +985,11 @@ where
   const MAX_TRIES: u32 = 10;
   for _ in 0..MAX_TRIES {
     let path = tmp_name(&mut rng, &dir, prefix.as_deref(), suffix.as_deref())?;
-    match fs.clone().mkdir_async(path.clone(), false, 0o700).await {
+    match fs
+      .clone()
+      .mkdir_async(path.clone(), false, Some(0o700))
+      .await
+    {
       Ok(_) => {
         // PERMISSIONS: ensure the absolute path is not leaked
         let path = strip_dir_prefix(&dir, dir_arg.as_deref(), path)?;
@@ -955,7 +1016,7 @@ pub fn op_fs_make_temp_file_sync<P>(
   #[string] dir_arg: Option<String>,
   #[string] prefix: Option<String>,
   #[string] suffix: Option<String>,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -1003,7 +1064,7 @@ pub async fn op_fs_make_temp_file_async<P>(
   #[string] dir_arg: Option<String>,
   #[string] prefix: Option<String>,
   #[string] suffix: Option<String>,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -1065,7 +1126,7 @@ fn make_temp_check_sync<P>(
   state: &mut OpState,
   dir: Option<&str>,
   api_name: &str,
-) -> Result<(PathBuf, FileSystemRc), AnyError>
+) -> Result<(PathBuf, FileSystemRc), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -1087,7 +1148,7 @@ fn make_temp_check_async<P>(
   state: Rc<RefCell<OpState>>,
   dir: Option<&str>,
   api_name: &str,
-) -> Result<(PathBuf, FileSystemRc), AnyError>
+) -> Result<(PathBuf, FileSystemRc), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -1112,10 +1173,10 @@ where
 fn validate_temporary_filename_component(
   component: &str,
   #[allow(unused_variables)] suffix: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), FsOpsError> {
   // Ban ASCII and Unicode control characters: these will often fail
   if let Some(c) = component.matches(|c: char| c.is_control()).next() {
-    bail!("Invalid control character in prefix or suffix: {:?}", c);
+    return Err(FsOpsError::InvalidControlCharacter(c.to_string()));
   }
   // Windows has the most restrictive filenames. As temp files aren't normal files, we just
   // use this set of banned characters for all platforms because wildcard-like files can also
@@ -1131,13 +1192,13 @@ fn validate_temporary_filename_component(
     .matches(|c: char| "<>:\"/\\|?*".contains(c))
     .next()
   {
-    bail!("Invalid character in prefix or suffix: {:?}", c);
+    return Err(FsOpsError::InvalidCharacter(c.to_string()));
   }
 
   // This check is only for Windows
   #[cfg(windows)]
   if suffix && component.ends_with(|c: char| ". ".contains(c)) {
-    bail!("Invalid trailing character in suffix");
+    return Err(FsOpsError::InvalidTrailingCharacter);
   }
 
   Ok(())
@@ -1148,7 +1209,7 @@ fn tmp_name(
   dir: &Path,
   prefix: Option<&str>,
   suffix: Option<&str>,
-) -> Result<PathBuf, AnyError> {
+) -> Result<PathBuf, FsOpsError> {
   let prefix = prefix.unwrap_or("");
   validate_temporary_filename_component(prefix, false)?;
   let suffix = suffix.unwrap_or("");
@@ -1175,7 +1236,7 @@ pub fn op_fs_write_file_sync<P>(
   create: bool,
   create_new: bool,
   #[buffer] data: JsBuffer,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -1203,7 +1264,7 @@ pub async fn op_fs_write_file_async<P>(
   create_new: bool,
   #[buffer] data: JsBuffer,
   #[smi] cancel_rid: Option<ResourceId>,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -1251,7 +1312,7 @@ where
 pub fn op_fs_read_file_sync<P>(
   state: &mut OpState,
   #[string] path: String,
-) -> Result<ToJsBuffer, AnyError>
+) -> Result<ToJsBuffer, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -1273,7 +1334,7 @@ pub async fn op_fs_read_file_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
   #[smi] cancel_rid: Option<ResourceId>,
-) -> Result<ToJsBuffer, AnyError>
+) -> Result<ToJsBuffer, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -1314,7 +1375,7 @@ where
 pub fn op_fs_read_file_text_sync<P>(
   state: &mut OpState,
   #[string] path: String,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -1336,7 +1397,7 @@ pub async fn op_fs_read_file_text_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
   #[smi] cancel_rid: Option<ResourceId>,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -1373,13 +1434,13 @@ where
   Ok(str)
 }
 
-fn to_seek_from(offset: i64, whence: i32) -> Result<SeekFrom, AnyError> {
+fn to_seek_from(offset: i64, whence: i32) -> Result<SeekFrom, FsOpsError> {
   let seek_from = match whence {
     0 => SeekFrom::Start(offset as u64),
     1 => SeekFrom::Current(offset),
     2 => SeekFrom::End(offset),
     _ => {
-      return Err(type_error(format!("Invalid seek mode: {whence}")));
+      return Err(FsOpsError::InvalidSeekMode(whence));
     }
   };
   Ok(seek_from)
@@ -1392,9 +1453,10 @@ pub fn op_fs_seek_sync(
   #[smi] rid: ResourceId,
   #[number] offset: i64,
   #[smi] whence: i32,
-) -> Result<u64, AnyError> {
+) -> Result<u64, FsOpsError> {
   let pos = to_seek_from(offset, whence)?;
-  let file = FileResource::get_file(state, rid)?;
+  let file =
+    FileResource::get_file(state, rid).map_err(FsOpsError::Resource)?;
   let cursor = file.seek_sync(pos)?;
   Ok(cursor)
 }
@@ -1406,9 +1468,10 @@ pub async fn op_fs_seek_async(
   #[smi] rid: ResourceId,
   #[number] offset: i64,
   #[smi] whence: i32,
-) -> Result<u64, AnyError> {
+) -> Result<u64, FsOpsError> {
   let pos = to_seek_from(offset, whence)?;
-  let file = FileResource::get_file(&state.borrow(), rid)?;
+  let file = FileResource::get_file(&state.borrow(), rid)
+    .map_err(FsOpsError::Resource)?;
   let cursor = file.seek_async(pos).await?;
   Ok(cursor)
 }
@@ -1417,8 +1480,9 @@ pub async fn op_fs_seek_async(
 pub fn op_fs_file_sync_data_sync(
   state: &mut OpState,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(state, rid)?;
+) -> Result<(), FsOpsError> {
+  let file =
+    FileResource::get_file(state, rid).map_err(FsOpsError::Resource)?;
   file.datasync_sync()?;
   Ok(())
 }
@@ -1427,8 +1491,9 @@ pub fn op_fs_file_sync_data_sync(
 pub async fn op_fs_file_sync_data_async(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(&state.borrow(), rid)?;
+) -> Result<(), FsOpsError> {
+  let file = FileResource::get_file(&state.borrow(), rid)
+    .map_err(FsOpsError::Resource)?;
   file.datasync_async().await?;
   Ok(())
 }
@@ -1437,8 +1502,9 @@ pub async fn op_fs_file_sync_data_async(
 pub fn op_fs_file_sync_sync(
   state: &mut OpState,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(state, rid)?;
+) -> Result<(), FsOpsError> {
+  let file =
+    FileResource::get_file(state, rid).map_err(FsOpsError::Resource)?;
   file.sync_sync()?;
   Ok(())
 }
@@ -1447,8 +1513,9 @@ pub fn op_fs_file_sync_sync(
 pub async fn op_fs_file_sync_async(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(&state.borrow(), rid)?;
+) -> Result<(), FsOpsError> {
+  let file = FileResource::get_file(&state.borrow(), rid)
+    .map_err(FsOpsError::Resource)?;
   file.sync_async().await?;
   Ok(())
 }
@@ -1458,8 +1525,9 @@ pub fn op_fs_file_stat_sync(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   #[buffer] stat_out_buf: &mut [u32],
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(state, rid)?;
+) -> Result<(), FsOpsError> {
+  let file =
+    FileResource::get_file(state, rid).map_err(FsOpsError::Resource)?;
   let stat = file.stat_sync()?;
   let serializable_stat = SerializableStat::from(stat);
   serializable_stat.write(stat_out_buf);
@@ -1471,8 +1539,9 @@ pub fn op_fs_file_stat_sync(
 pub async fn op_fs_file_stat_async(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<SerializableStat, AnyError> {
-  let file = FileResource::get_file(&state.borrow(), rid)?;
+) -> Result<SerializableStat, FsOpsError> {
+  let file = FileResource::get_file(&state.borrow(), rid)
+    .map_err(FsOpsError::Resource)?;
   let stat = file.stat_async().await?;
   Ok(stat.into())
 }
@@ -1482,8 +1551,9 @@ pub fn op_fs_flock_sync(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   exclusive: bool,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(state, rid)?;
+) -> Result<(), FsOpsError> {
+  let file =
+    FileResource::get_file(state, rid).map_err(FsOpsError::Resource)?;
   file.lock_sync(exclusive)?;
   Ok(())
 }
@@ -1493,8 +1563,9 @@ pub async fn op_fs_flock_async(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   exclusive: bool,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(&state.borrow(), rid)?;
+) -> Result<(), FsOpsError> {
+  let file = FileResource::get_file(&state.borrow(), rid)
+    .map_err(FsOpsError::Resource)?;
   file.lock_async(exclusive).await?;
   Ok(())
 }
@@ -1503,8 +1574,9 @@ pub async fn op_fs_flock_async(
 pub fn op_fs_funlock_sync(
   state: &mut OpState,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(state, rid)?;
+) -> Result<(), FsOpsError> {
+  let file =
+    FileResource::get_file(state, rid).map_err(FsOpsError::Resource)?;
   file.unlock_sync()?;
   Ok(())
 }
@@ -1513,8 +1585,9 @@ pub fn op_fs_funlock_sync(
 pub async fn op_fs_funlock_async(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(&state.borrow(), rid)?;
+) -> Result<(), FsOpsError> {
+  let file = FileResource::get_file(&state.borrow(), rid)
+    .map_err(FsOpsError::Resource)?;
   file.unlock_async().await?;
   Ok(())
 }
@@ -1524,8 +1597,9 @@ pub fn op_fs_ftruncate_sync(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   #[number] len: u64,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(state, rid)?;
+) -> Result<(), FsOpsError> {
+  let file =
+    FileResource::get_file(state, rid).map_err(FsOpsError::Resource)?;
   file.truncate_sync(len)?;
   Ok(())
 }
@@ -1535,8 +1609,9 @@ pub async fn op_fs_file_truncate_async(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[number] len: u64,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(&state.borrow(), rid)?;
+) -> Result<(), FsOpsError> {
+  let file = FileResource::get_file(&state.borrow(), rid)
+    .map_err(FsOpsError::Resource)?;
   file.truncate_async(len).await?;
   Ok(())
 }
@@ -1549,8 +1624,9 @@ pub fn op_fs_futime_sync(
   #[smi] atime_nanos: u32,
   #[number] mtime_secs: i64,
   #[smi] mtime_nanos: u32,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(state, rid)?;
+) -> Result<(), FsOpsError> {
+  let file =
+    FileResource::get_file(state, rid).map_err(FsOpsError::Resource)?;
   file.utime_sync(atime_secs, atime_nanos, mtime_secs, mtime_nanos)?;
   Ok(())
 }
@@ -1563,42 +1639,64 @@ pub async fn op_fs_futime_async(
   #[smi] atime_nanos: u32,
   #[number] mtime_secs: i64,
   #[smi] mtime_nanos: u32,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(&state.borrow(), rid)?;
+) -> Result<(), FsOpsError> {
+  let file = FileResource::get_file(&state.borrow(), rid)
+    .map_err(FsOpsError::Resource)?;
   file
     .utime_async(atime_secs, atime_nanos, mtime_secs, mtime_nanos)
     .await?;
   Ok(())
 }
 
-trait WithContext {
-  fn context<E: Into<Box<dyn std::error::Error + Send + Sync>>>(
-    self,
-    desc: E,
-  ) -> AnyError;
+#[derive(Debug)]
+pub struct OperationError {
+  operation: &'static str,
+  kind: OperationErrorKind,
+  pub err: FsError,
 }
 
-impl WithContext for FsError {
-  fn context<E: Into<Box<dyn std::error::Error + Send + Sync>>>(
-    self,
-    desc: E,
-  ) -> AnyError {
-    match self {
-      FsError::Io(io) => {
-        AnyError::new(io::Error::new(io.kind(), desc)).context(io)
+impl std::fmt::Display for OperationError {
+  fn fmt(&self, f: &mut Formatter<'_>) -> std::fmt::Result {
+    if let FsError::Io(e) = &self.err {
+      std::fmt::Display::fmt(&e, f)?;
+      f.write_str(": ")?;
+    }
+
+    f.write_str(self.operation)?;
+
+    match &self.kind {
+      OperationErrorKind::Bare => Ok(()),
+      OperationErrorKind::WithPath(path) => write!(f, " '{}'", path.display()),
+      OperationErrorKind::WithTwoPaths(from, to) => {
+        write!(f, " '{}' -> '{}'", from.display(), to.display())
       }
-      _ => self.into(),
     }
   }
 }
 
+impl std::error::Error for OperationError {
+  fn source(&self) -> Option<&(dyn Error + 'static)> {
+    if let FsError::Io(err) = &self.err {
+      Some(err)
+    } else {
+      None
+    }
+  }
+}
+
+#[derive(Debug)]
+pub enum OperationErrorKind {
+  Bare,
+  WithPath(PathBuf),
+  WithTwoPaths(PathBuf, PathBuf),
+}
+
 trait MapErrContext {
   type R;
 
-  fn context_fn<F, E>(self, f: F) -> Self::R
+  fn context_fn<F>(self, f: F) -> Self::R
   where
-    F: FnOnce() -> E,
-    E: Into<Box<dyn std::error::Error + Send + Sync>>;
+    F: FnOnce(FsError) -> OperationError;
 
   fn context(self, desc: &'static str) -> Self::R;
 
@@ -1613,25 +1711,29 @@ trait MapErrContext {
 }
 
 impl<T> MapErrContext for Result<T, FsError> {
-  type R = Result<T, AnyError>;
+  type R = Result<T, FsOpsError>;
 
-  fn context_fn<F, E>(self, f: F) -> Self::R
+  fn context_fn<F>(self, f: F) -> Self::R
   where
-    F: FnOnce() -> E,
-    E: Into<Box<dyn std::error::Error + Send + Sync>>,
+    F: FnOnce(FsError) -> OperationError,
   {
-    self.map_err(|err| {
-      let message = f();
-      err.context(message)
+    self.map_err(|err| FsOpsError::OperationError(f(err)))
+  }
+
+  fn context(self, operation: &'static str) -> Self::R {
+    self.context_fn(move |err| OperationError {
+      operation,
+      kind: OperationErrorKind::Bare,
+      err,
     })
   }
 
-  fn context(self, desc: &'static str) -> Self::R {
-    self.context_fn(move || desc)
-  }
-
   fn context_path(self, operation: &'static str, path: &Path) -> Self::R {
-    self.context_fn(|| format!("{operation} '{}'", path.display()))
+    self.context_fn(|err| OperationError {
+      operation,
+      kind: OperationErrorKind::WithPath(path.to_path_buf()),
+      err,
+    })
   }
 
   fn context_two_path(
@@ -1640,21 +1742,19 @@ impl<T> MapErrContext for Result<T, FsError> {
     oldpath: &Path,
     newpath: &Path,
   ) -> Self::R {
-    self.context_fn(|| {
-      format!(
-        "{operation} '{}' -> '{}'",
-        oldpath.display(),
-        newpath.display()
-      )
+    self.context_fn(|err| OperationError {
+      operation,
+      kind: OperationErrorKind::WithTwoPaths(
+        oldpath.to_path_buf(),
+        newpath.to_path_buf(),
+      ),
+      err,
     })
   }
 }
 
-fn path_into_string(s: std::ffi::OsString) -> Result<String, AnyError> {
-  s.into_string().map_err(|s| {
-    let message = format!("File name or path {s:?} is not valid UTF-8");
-    custom_error("InvalidData", message)
-  })
+fn path_into_string(s: std::ffi::OsString) -> Result<String, FsOpsError> {
+  s.into_string().map_err(FsOpsError::InvalidUtf8)
 }
 
 macro_rules! create_struct_writer {
@@ -1695,6 +1795,8 @@ create_struct_writer! {
     atime: u64,
     birthtime_set: bool,
     birthtime: u64,
+    ctime_set: bool,
+    ctime: u64,
     // Following are only valid under Unix.
     dev: u64,
     ino: u64,
@@ -1726,6 +1828,8 @@ impl From<FsStat> for SerializableStat {
       atime: stat.atime.unwrap_or(0),
       birthtime_set: stat.birthtime.is_some(),
       birthtime: stat.birthtime.unwrap_or(0),
+      ctime_set: stat.ctime.is_some(),
+      ctime: stat.ctime.unwrap_or(0),
 
       dev: stat.dev,
       ino: stat.ino,
diff --git a/ext/fs/std_fs.rs b/ext/fs/std_fs.rs
index d8d5f65027..73439d9bab 100644
--- a/ext/fs/std_fs.rs
+++ b/ext/fs/std_fs.rs
@@ -11,13 +11,13 @@ use std::path::Path;
 use std::path::PathBuf;
 use std::rc::Rc;
 
-use deno_core::normalize_path;
 use deno_core::unsync::spawn_blocking;
 use deno_io::fs::File;
 use deno_io::fs::FsError;
 use deno_io::fs::FsResult;
 use deno_io::fs::FsStat;
 use deno_io::StdFileResourceInner;
+use deno_path_util::normalize_path;
 
 use crate::interface::AccessCheckCb;
 use crate::interface::FsDirEntry;
@@ -101,7 +101,7 @@ impl FileSystem for RealFs {
     &self,
     path: &Path,
     recursive: bool,
-    mode: u32,
+    mode: Option<u32>,
   ) -> FsResult<()> {
     mkdir(path, recursive, mode)
   }
@@ -109,7 +109,7 @@ impl FileSystem for RealFs {
     &self,
     path: PathBuf,
     recursive: bool,
-    mode: u32,
+    mode: Option<u32>,
   ) -> FsResult<()> {
     spawn_blocking(move || mkdir(&path, recursive, mode)).await?
   }
@@ -407,11 +407,11 @@ impl FileSystem for RealFs {
   }
 }
 
-fn mkdir(path: &Path, recursive: bool, mode: u32) -> FsResult<()> {
+fn mkdir(path: &Path, recursive: bool, mode: Option<u32>) -> FsResult<()> {
   let mut builder = fs::DirBuilder::new();
   builder.recursive(recursive);
   #[cfg(unix)]
-  {
+  if let Some(mode) = mode {
     use std::os::unix::fs::DirBuilderExt;
     builder.mode(mode);
   }
@@ -821,24 +821,46 @@ fn stat_extra(
     Ok(info.dwVolumeSerialNumber as u64)
   }
 
+  const WINDOWS_TICK: i64 = 10_000; // 100-nanosecond intervals in a millisecond
+  const SEC_TO_UNIX_EPOCH: i64 = 11_644_473_600; // Seconds between Windows epoch and Unix epoch
+
+  fn windows_time_to_unix_time_msec(windows_time: &i64) -> i64 {
+    let milliseconds_since_windows_epoch = windows_time / WINDOWS_TICK;
+    milliseconds_since_windows_epoch - SEC_TO_UNIX_EPOCH * 1000
+  }
+
   use windows_sys::Wdk::Storage::FileSystem::FILE_ALL_INFORMATION;
+  use windows_sys::Win32::Foundation::NTSTATUS;
 
   unsafe fn query_file_information(
     handle: winapi::shared::ntdef::HANDLE,
-  ) -> std::io::Result<FILE_ALL_INFORMATION> {
+  ) -> Result<FILE_ALL_INFORMATION, NTSTATUS> {
     use windows_sys::Wdk::Storage::FileSystem::NtQueryInformationFile;
+    use windows_sys::Win32::Foundation::RtlNtStatusToDosError;
+    use windows_sys::Win32::Foundation::ERROR_MORE_DATA;
+    use windows_sys::Win32::System::IO::IO_STATUS_BLOCK;
 
     let mut info = std::mem::MaybeUninit::<FILE_ALL_INFORMATION>::zeroed();
+    let mut io_status_block =
+      std::mem::MaybeUninit::<IO_STATUS_BLOCK>::zeroed();
     let status = NtQueryInformationFile(
       handle as _,
-      std::ptr::null_mut(),
+      io_status_block.as_mut_ptr(),
       info.as_mut_ptr() as *mut _,
       std::mem::size_of::<FILE_ALL_INFORMATION>() as _,
       18, /* FileAllInformation */
     );
 
     if status < 0 {
-      return Err(std::io::Error::last_os_error());
+      let converted_status = RtlNtStatusToDosError(status);
+
+      // If error more data is returned, then it means that the buffer is too small to get full filename information
+      // to have that we should retry. However, since we only use BasicInformation and StandardInformation, it is fine to ignore it
+      // since struct is populated with other data anyway.
+      // https://learn.microsoft.com/en-us/windows-hardware/drivers/ddi/ntifs/nf-ntifs-ntqueryinformationfile#remarksdd
+      if converted_status != ERROR_MORE_DATA {
+        return Err(converted_status as NTSTATUS);
+      }
     }
 
     Ok(info.assume_init())
@@ -862,10 +884,13 @@ fn stat_extra(
     }
 
     let result = get_dev(file_handle);
-    CloseHandle(file_handle);
     fsstat.dev = result?;
 
     if let Ok(file_info) = query_file_information(file_handle) {
+      fsstat.ctime = Some(windows_time_to_unix_time_msec(
+        &file_info.BasicInformation.ChangeTime,
+      ) as u64);
+
       if file_info.BasicInformation.FileAttributes
         & winapi::um::winnt::FILE_ATTRIBUTE_REPARSE_POINT
         != 0
@@ -898,6 +923,7 @@ fn stat_extra(
       }
     }
 
+    CloseHandle(file_handle);
     Ok(())
   }
 }
@@ -929,7 +955,7 @@ fn exists(path: &Path) -> bool {
 }
 
 fn realpath(path: &Path) -> FsResult<PathBuf> {
-  Ok(deno_core::strip_unc_prefix(path.canonicalize()?))
+  Ok(deno_path_util::strip_unc_prefix(path.canonicalize()?))
 }
 
 fn read_dir(path: &Path) -> FsResult<Vec<FsDirEntry>> {
diff --git a/ext/http/00_serve.ts b/ext/http/00_serve.ts
index 3b9b085a22..fcdb87d092 100644
--- a/ext/http/00_serve.ts
+++ b/ext/http/00_serve.ts
@@ -14,6 +14,7 @@ import {
   op_http_get_request_headers,
   op_http_get_request_method_and_url,
   op_http_read_request_body,
+  op_http_request_on_cancel,
   op_http_serve,
   op_http_serve_on,
   op_http_set_promise_complete,
@@ -41,6 +42,10 @@ const {
   Uint8Array,
   Promise,
 } = primordials;
+const {
+  getAsyncContext,
+  setAsyncContext,
+} = core;
 
 import { InnerBody } from "ext:deno_fetch/22_body.js";
 import { Event } from "ext:deno_web/02_event.js";
@@ -76,7 +81,11 @@ import {
   ReadableStreamPrototype,
   resourceForReadableStream,
 } from "ext:deno_web/06_streams.js";
-import { listen, listenOptionApiName, TcpConn } from "ext:deno_net/01_net.js";
+import {
+  listen,
+  listenOptionApiName,
+  UpgradedConn,
+} from "ext:deno_net/01_net.js";
 import { hasTlsKeyPairOptions, listenTls } from "ext:deno_net/02_tls.js";
 import { SymbolAsyncDispose } from "ext:deno_web/00_infra.js";
 
@@ -189,7 +198,7 @@ class InnerRequest {
 
       const upgradeRid = op_http_upgrade_raw(external);
 
-      const conn = new TcpConn(
+      const conn = new UpgradedConn(
         upgradeRid,
         underlyingConn?.remoteAddr,
         underlyingConn?.localAddr,
@@ -369,6 +378,18 @@ class InnerRequest {
   get external() {
     return this.#external;
   }
+
+  onCancel(callback) {
+    if (this.#external === null) {
+      callback();
+      return;
+    }
+
+    PromisePrototypeThen(
+      op_http_request_on_cancel(this.#external),
+      callback,
+    );
+  }
 }
 
 class CallbackContext {
@@ -380,8 +401,10 @@ class CallbackContext {
   /** @type {Promise<void> | undefined} */
   closing;
   listener;
+  asyncContext;
 
   constructor(signal, args, listener) {
+    this.asyncContext = getAsyncContext();
     // The abort signal triggers a non-graceful shutdown
     signal?.addEventListener(
       "abort",
@@ -491,82 +514,89 @@ function fastSyncResponseOrStream(
  */
 function mapToCallback(context, callback, onError) {
   return async function (req) {
-    // Get the response from the user-provided callback. If that fails, use onError. If that fails, return a fallback
-    // 500 error.
-    let innerRequest;
-    let response;
+    const asyncContext = getAsyncContext();
+    setAsyncContext(context.asyncContext);
+
     try {
-      innerRequest = new InnerRequest(req, context);
-      const request = fromInnerRequest(innerRequest, "immutable");
-      innerRequest.request = request;
-      response = await callback(
-        request,
-        new ServeHandlerInfo(innerRequest),
-      );
-
-      // Throwing Error if the handler return value is not a Response class
-      if (!ObjectPrototypeIsPrototypeOf(ResponsePrototype, response)) {
-        throw new TypeError(
-          "Return value from serve handler must be a response or a promise resolving to a response",
-        );
-      }
-
-      if (response.type === "error") {
-        throw new TypeError(
-          "Return value from serve handler must not be an error response (like Response.error())",
-        );
-      }
-
-      if (response.bodyUsed) {
-        throw new TypeError(
-          "The body of the Response returned from the serve handler has already been consumed",
-        );
-      }
-    } catch (error) {
+      // Get the response from the user-provided callback. If that fails, use onError. If that fails, return a fallback
+      // 500 error.
+      let innerRequest;
+      let response;
       try {
-        response = await onError(error);
+        innerRequest = new InnerRequest(req, context);
+        const request = fromInnerRequest(innerRequest, "immutable");
+        innerRequest.request = request;
+        response = await callback(
+          request,
+          new ServeHandlerInfo(innerRequest),
+        );
+
+        // Throwing Error if the handler return value is not a Response class
         if (!ObjectPrototypeIsPrototypeOf(ResponsePrototype, response)) {
           throw new TypeError(
-            "Return value from onError handler must be a response or a promise resolving to a response",
+            "Return value from serve handler must be a response or a promise resolving to a response",
+          );
+        }
+
+        if (response.type === "error") {
+          throw new TypeError(
+            "Return value from serve handler must not be an error response (like Response.error())",
+          );
+        }
+
+        if (response.bodyUsed) {
+          throw new TypeError(
+            "The body of the Response returned from the serve handler has already been consumed",
           );
         }
       } catch (error) {
-        // deno-lint-ignore no-console
-        console.error("Exception in onError while handling exception", error);
-        response = internalServerError();
+        try {
+          response = await onError(error);
+          if (!ObjectPrototypeIsPrototypeOf(ResponsePrototype, response)) {
+            throw new TypeError(
+              "Return value from onError handler must be a response or a promise resolving to a response",
+            );
+          }
+        } catch (error) {
+          // deno-lint-ignore no-console
+          console.error("Exception in onError while handling exception", error);
+          response = internalServerError();
+        }
       }
-    }
-    const inner = toInnerResponse(response);
-    if (innerRequest?.[_upgraded]) {
-      // We're done here as the connection has been upgraded during the callback and no longer requires servicing.
-      if (response !== UPGRADE_RESPONSE_SENTINEL) {
-        // deno-lint-ignore no-console
-        console.error("Upgrade response was not returned from callback");
-        context.close();
+      const inner = toInnerResponse(response);
+      if (innerRequest?.[_upgraded]) {
+        // We're done here as the connection has been upgraded during the callback and no longer requires servicing.
+        if (response !== UPGRADE_RESPONSE_SENTINEL) {
+          // deno-lint-ignore no-console
+          console.error("Upgrade response was not returned from callback");
+          context.close();
+        }
+        innerRequest?.[_upgraded]();
+        return;
       }
-      innerRequest?.[_upgraded]();
-      return;
-    }
 
-    // Did everything shut down while we were waiting?
-    if (context.closed) {
-      // We're shutting down, so this status shouldn't make it back to the client but "Service Unavailable" seems appropriate
-      innerRequest?.close();
-      op_http_set_promise_complete(req, 503);
-      return;
-    }
-
-    const status = inner.status;
-    const headers = inner.headerList;
-    if (headers && headers.length > 0) {
-      if (headers.length == 1) {
-        op_http_set_response_header(req, headers[0][0], headers[0][1]);
-      } else {
-        op_http_set_response_headers(req, headers);
+      // Did everything shut down while we were waiting?
+      if (context.closed) {
+        // We're shutting down, so this status shouldn't make it back to the client but "Service Unavailable" seems appropriate
+        innerRequest?.close();
+        op_http_set_promise_complete(req, 503);
+        return;
       }
-    }
 
-    fastSyncResponseOrStream(req, inner.body, status, innerRequest);
+      const status = inner.status;
+      const headers = inner.headerList;
+      if (headers && headers.length > 0) {
+        if (headers.length == 1) {
+          op_http_set_response_header(req, headers[0][0], headers[0][1]);
+        } else {
+          op_http_set_response_headers(req, headers);
+        }
+      }
+
+      fastSyncResponseOrStream(req, inner.body, status, innerRequest);
+    } finally {
+      setAsyncContext(asyncContext);
+    }
   };
 }
 
diff --git a/ext/http/Cargo.toml b/ext/http/Cargo.toml
index ba21e3f30d..ed98fe349c 100644
--- a/ext/http/Cargo.toml
+++ b/ext/http/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_http"
-version = "0.166.0"
+version = "0.175.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/http/fly_accept_encoding.rs b/ext/http/fly_accept_encoding.rs
index 94e3368767..4d6fd2231e 100644
--- a/ext/http/fly_accept_encoding.rs
+++ b/ext/http/fly_accept_encoding.rs
@@ -119,7 +119,7 @@ fn encodings_iter_inner<'s>(
       };
       Some(Ok((encoding, qval)))
     })
-    .map(|r| r?) // flatten Result<Result<...
+    .flatten()
 }
 
 #[cfg(test)]
diff --git a/ext/http/http_next.rs b/ext/http/http_next.rs
index efe1b88c93..1251f00cc0 100644
--- a/ext/http/http_next.rs
+++ b/ext/http/http_next.rs
@@ -19,7 +19,6 @@ use crate::service::SignallingRc;
 use crate::websocket_upgrade::WebSocketUpgrade;
 use crate::LocalExecutor;
 use cache_control::CacheControl;
-use deno_core::error::AnyError;
 use deno_core::external;
 use deno_core::futures::future::poll_fn;
 use deno_core::futures::TryFutureExt;
@@ -146,12 +145,32 @@ macro_rules! clone_external {
   }};
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum HttpNextError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("{0}")]
+  Io(#[from] io::Error),
+  #[error(transparent)]
+  WebSocketUpgrade(crate::websocket_upgrade::WebSocketUpgradeError),
+  #[error("{0}")]
+  Hyper(#[from] hyper::Error),
+  #[error(transparent)]
+  JoinError(#[from] tokio::task::JoinError),
+  #[error(transparent)]
+  Canceled(#[from] deno_core::Canceled),
+  #[error(transparent)]
+  HttpPropertyExtractor(deno_core::error::AnyError),
+  #[error(transparent)]
+  UpgradeUnavailable(#[from] crate::service::UpgradeUnavailableError),
+}
+
 #[op2(fast)]
 #[smi]
 pub fn op_http_upgrade_raw(
   state: &mut OpState,
   external: *const c_void,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, HttpNextError> {
   // SAFETY: external is deleted before calling this op.
   let http = unsafe { take_external!(external, "op_http_upgrade_raw") };
 
@@ -177,7 +196,7 @@ pub fn op_http_upgrade_raw(
           upgraded.write_all(&bytes).await?;
           break upgraded;
         }
-        Err(err) => return Err(err),
+        Err(err) => return Err(HttpNextError::WebSocketUpgrade(err)),
       }
     };
 
@@ -193,7 +212,7 @@ pub fn op_http_upgrade_raw(
         }
         read_tx.write_all(&buf[..read]).await?;
       }
-      Ok::<_, AnyError>(())
+      Ok::<_, HttpNextError>(())
     });
     spawn(async move {
       let mut buf = [0; 1024];
@@ -204,7 +223,7 @@ pub fn op_http_upgrade_raw(
         }
         upgraded_tx.write_all(&buf[..read]).await?;
       }
-      Ok::<_, AnyError>(())
+      Ok::<_, HttpNextError>(())
     });
 
     Ok(())
@@ -223,7 +242,7 @@ pub async fn op_http_upgrade_websocket_next(
   state: Rc<RefCell<OpState>>,
   external: *const c_void,
   #[serde] headers: Vec<(ByteString, ByteString)>,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, HttpNextError> {
   let http =
     // SAFETY: external is deleted before calling this op.
     unsafe { take_external!(external, "op_http_upgrade_websocket_next") };
@@ -246,7 +265,11 @@ pub async fn op_http_upgrade_websocket_next(
 
   // Stage 3: take the extracted raw network stream and upgrade it to a websocket, then return it
   let (stream, bytes) = extract_network_stream(upgraded);
-  ws_create_server_stream(&mut state.borrow_mut(), stream, bytes)
+  Ok(ws_create_server_stream(
+    &mut state.borrow_mut(),
+    stream,
+    bytes,
+  ))
 }
 
 #[op2(fast)]
@@ -296,7 +319,7 @@ where
   let authority: v8::Local<v8::Value> = match request_properties.authority {
     Some(authority) => v8::String::new_from_utf8(
       scope,
-      authority.as_ref(),
+      authority.as_bytes(),
       v8::NewStringType::Normal,
     )
     .unwrap()
@@ -305,15 +328,25 @@ where
   };
 
   // Only extract the path part - we handle authority elsewhere
-  let path = match &request_parts.uri.path_and_query() {
-    Some(path_and_query) => path_and_query.to_string(),
-    None => "".to_owned(),
+  let path = match request_parts.uri.path_and_query() {
+    Some(path_and_query) => {
+      let path = path_and_query.as_str();
+      if matches!(path.as_bytes().first(), Some(b'/' | b'*')) {
+        Cow::Borrowed(path)
+      } else {
+        Cow::Owned(format!("/{}", path))
+      }
+    }
+    None => Cow::Borrowed(""),
   };
 
-  let path: v8::Local<v8::Value> =
-    v8::String::new_from_utf8(scope, path.as_ref(), v8::NewStringType::Normal)
-      .unwrap()
-      .into();
+  let path: v8::Local<v8::Value> = v8::String::new_from_utf8(
+    scope,
+    path.as_bytes(),
+    v8::NewStringType::Normal,
+  )
+  .unwrap()
+  .into();
 
   let peer_address: v8::Local<v8::Value> = v8::String::new_from_utf8(
     scope,
@@ -531,6 +564,7 @@ fn is_request_compressible(
   match accept_encoding.to_str() {
     // Firefox and Chrome send this -- no need to parse
     Ok("gzip, deflate, br") => return Compression::Brotli,
+    Ok("gzip, deflate, br, zstd") => return Compression::Brotli,
     Ok("gzip") => return Compression::GZip,
     Ok("br") => return Compression::Brotli,
     _ => (),
@@ -667,6 +701,27 @@ fn set_response(
   http.complete();
 }
 
+#[op2(fast)]
+pub fn op_http_get_request_cancelled(external: *const c_void) -> bool {
+  let http =
+    // SAFETY: op is called with external.
+    unsafe { clone_external!(external, "op_http_get_request_cancelled") };
+  http.cancelled()
+}
+
+#[op2(async)]
+pub async fn op_http_request_on_cancel(external: *const c_void) {
+  let http =
+    // SAFETY: op is called with external.
+    unsafe { clone_external!(external, "op_http_request_on_cancel") };
+  let (tx, rx) = tokio::sync::oneshot::channel();
+
+  http.on_cancel(tx);
+  drop(http);
+
+  rx.await.ok();
+}
+
 /// Returned promise resolves when body streaming finishes.
 /// Call [`op_http_close_after_finish`] when done with the external.
 #[op2(async)]
@@ -676,7 +731,7 @@ pub async fn op_http_set_response_body_resource(
   #[smi] stream_rid: ResourceId,
   auto_close: bool,
   status: u16,
-) -> Result<bool, AnyError> {
+) -> Result<bool, HttpNextError> {
   let http =
     // SAFETY: op is called with external.
     unsafe { clone_external!(external, "op_http_set_response_body_resource") };
@@ -691,9 +746,15 @@ pub async fn op_http_set_response_body_resource(
   let resource = {
     let mut state = state.borrow_mut();
     if auto_close {
-      state.resource_table.take_any(stream_rid)?
+      state
+        .resource_table
+        .take_any(stream_rid)
+        .map_err(HttpNextError::Resource)?
     } else {
-      state.resource_table.get_any(stream_rid)?
+      state
+        .resource_table
+        .get_any(stream_rid)
+        .map_err(HttpNextError::Resource)?
     }
   };
 
@@ -800,17 +861,17 @@ async fn serve_http2_autodetect(
   io: impl HttpServeStream,
   svc: impl HttpService<Incoming, ResBody = HttpRecordResponse> + 'static,
   cancel: Rc<CancelHandle>,
-) -> Result<(), AnyError> {
+) -> Result<(), HttpNextError> {
   let prefix = NetworkStreamPrefixCheck::new(io, HTTP2_PREFIX);
   let (matches, io) = prefix.match_prefix().await?;
   if matches {
     serve_http2_unconditional(io, svc, cancel)
       .await
-      .map_err(|e| e.into())
+      .map_err(HttpNextError::Hyper)
   } else {
     serve_http11_unconditional(io, svc, cancel)
       .await
-      .map_err(|e| e.into())
+      .map_err(HttpNextError::Hyper)
   }
 }
 
@@ -819,7 +880,7 @@ fn serve_https(
   request_info: HttpConnectionProperties,
   lifetime: HttpLifetime,
   tx: tokio::sync::mpsc::Sender<Rc<HttpRecord>>,
-) -> JoinHandle<Result<(), AnyError>> {
+) -> JoinHandle<Result<(), HttpNextError>> {
   let HttpLifetime {
     server_state,
     connection_cancel_handle,
@@ -838,11 +899,11 @@ fn serve_https(
       if Some(TLS_ALPN_HTTP_2) == handshake.as_deref() {
         serve_http2_unconditional(io, svc, listen_cancel_handle)
           .await
-          .map_err(|e| e.into())
+          .map_err(HttpNextError::Hyper)
       } else if Some(TLS_ALPN_HTTP_11) == handshake.as_deref() {
         serve_http11_unconditional(io, svc, listen_cancel_handle)
           .await
-          .map_err(|e| e.into())
+          .map_err(HttpNextError::Hyper)
       } else {
         serve_http2_autodetect(io, svc, listen_cancel_handle).await
       }
@@ -856,7 +917,7 @@ fn serve_http(
   request_info: HttpConnectionProperties,
   lifetime: HttpLifetime,
   tx: tokio::sync::mpsc::Sender<Rc<HttpRecord>>,
-) -> JoinHandle<Result<(), AnyError>> {
+) -> JoinHandle<Result<(), HttpNextError>> {
   let HttpLifetime {
     server_state,
     connection_cancel_handle,
@@ -877,7 +938,7 @@ fn serve_http_on<HTTP>(
   listen_properties: &HttpListenProperties,
   lifetime: HttpLifetime,
   tx: tokio::sync::mpsc::Sender<Rc<HttpRecord>>,
-) -> JoinHandle<Result<(), AnyError>>
+) -> JoinHandle<Result<(), HttpNextError>>
 where
   HTTP: HttpPropertyExtractor,
 {
@@ -908,7 +969,7 @@ struct HttpLifetime {
 }
 
 struct HttpJoinHandle {
-  join_handle: AsyncRefCell<Option<JoinHandle<Result<(), AnyError>>>>,
+  join_handle: AsyncRefCell<Option<JoinHandle<Result<(), HttpNextError>>>>,
   connection_cancel_handle: Rc<CancelHandle>,
   listen_cancel_handle: Rc<CancelHandle>,
   rx: AsyncRefCell<tokio::sync::mpsc::Receiver<Rc<HttpRecord>>>,
@@ -968,12 +1029,13 @@ impl Drop for HttpJoinHandle {
 pub fn op_http_serve<HTTP>(
   state: Rc<RefCell<OpState>>,
   #[smi] listener_rid: ResourceId,
-) -> Result<(ResourceId, &'static str, String), AnyError>
+) -> Result<(ResourceId, &'static str, String), HttpNextError>
 where
   HTTP: HttpPropertyExtractor,
 {
   let listener =
-    HTTP::get_listener_for_rid(&mut state.borrow_mut(), listener_rid)?;
+    HTTP::get_listener_for_rid(&mut state.borrow_mut(), listener_rid)
+      .map_err(HttpNextError::Resource)?;
 
   let listen_properties = HTTP::listen_properties_from_listener(&listener)?;
 
@@ -988,7 +1050,8 @@ where
     loop {
       let conn = HTTP::accept_connection_from_listener(&listener)
         .try_or_cancel(listen_cancel_clone.clone())
-        .await?;
+        .await
+        .map_err(HttpNextError::HttpPropertyExtractor)?;
       serve_http_on::<HTTP>(
         conn,
         &listen_properties_clone,
@@ -997,7 +1060,7 @@ where
       );
     }
     #[allow(unreachable_code)]
-    Ok::<_, AnyError>(())
+    Ok::<_, HttpNextError>(())
   });
 
   // Set the handle after we start the future
@@ -1017,25 +1080,25 @@ where
 pub fn op_http_serve_on<HTTP>(
   state: Rc<RefCell<OpState>>,
   #[smi] connection_rid: ResourceId,
-) -> Result<(ResourceId, &'static str, String), AnyError>
+) -> Result<(ResourceId, &'static str, String), HttpNextError>
 where
   HTTP: HttpPropertyExtractor,
 {
   let connection =
-    HTTP::get_connection_for_rid(&mut state.borrow_mut(), connection_rid)?;
+    HTTP::get_connection_for_rid(&mut state.borrow_mut(), connection_rid)
+      .map_err(HttpNextError::Resource)?;
 
   let listen_properties = HTTP::listen_properties_from_connection(&connection)?;
 
   let (tx, rx) = tokio::sync::mpsc::channel(10);
   let resource: Rc<HttpJoinHandle> = Rc::new(HttpJoinHandle::new(rx));
 
-  let handle: JoinHandle<Result<(), deno_core::anyhow::Error>> =
-    serve_http_on::<HTTP>(
-      connection,
-      &listen_properties,
-      resource.lifetime(),
-      tx,
-    );
+  let handle = serve_http_on::<HTTP>(
+    connection,
+    &listen_properties,
+    resource.lifetime(),
+    tx,
+  );
 
   // Set the handle after we start the future
   *RcRef::map(&resource, |this| &this.join_handle)
@@ -1081,12 +1144,13 @@ pub fn op_http_try_wait(
 pub async fn op_http_wait(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<*const c_void, AnyError> {
+) -> Result<*const c_void, HttpNextError> {
   // We will get the join handle initially, as we might be consuming requests still
   let join_handle = state
     .borrow_mut()
     .resource_table
-    .get::<HttpJoinHandle>(rid)?;
+    .get::<HttpJoinHandle>(rid)
+    .map_err(HttpNextError::Resource)?;
 
   let cancel = join_handle.listen_cancel_handle();
   let next = async {
@@ -1113,13 +1177,12 @@ pub async fn op_http_wait(
 
   // Filter out shutdown (ENOTCONN) errors
   if let Err(err) = res {
-    if let Some(err) = err.source() {
-      if let Some(err) = err.downcast_ref::<io::Error>() {
-        if err.kind() == io::ErrorKind::NotConnected {
-          return Ok(null());
-        }
+    if let HttpNextError::Io(err) = &err {
+      if err.kind() == io::ErrorKind::NotConnected {
+        return Ok(null());
       }
     }
+
     return Err(err);
   }
 
@@ -1132,7 +1195,7 @@ pub fn op_http_cancel(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   graceful: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), deno_core::error::AnyError> {
   let join_handle = state.resource_table.get::<HttpJoinHandle>(rid)?;
 
   if graceful {
@@ -1152,11 +1215,12 @@ pub async fn op_http_close(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   graceful: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), HttpNextError> {
   let join_handle = state
     .borrow_mut()
     .resource_table
-    .take::<HttpJoinHandle>(rid)?;
+    .take::<HttpJoinHandle>(rid)
+    .map_err(HttpNextError::Resource)?;
 
   if graceful {
     http_general_trace!("graceful shutdown");
@@ -1202,23 +1266,26 @@ impl UpgradeStream {
     }
   }
 
-  async fn read(self: Rc<Self>, buf: &mut [u8]) -> Result<usize, AnyError> {
+  async fn read(
+    self: Rc<Self>,
+    buf: &mut [u8],
+  ) -> Result<usize, std::io::Error> {
     let cancel_handle = RcRef::map(self.clone(), |this| &this.cancel_handle);
     async {
       let read = RcRef::map(self, |this| &this.read);
       let mut read = read.borrow_mut().await;
-      Ok(Pin::new(&mut *read).read(buf).await?)
+      Pin::new(&mut *read).read(buf).await
     }
     .try_or_cancel(cancel_handle)
     .await
   }
 
-  async fn write(self: Rc<Self>, buf: &[u8]) -> Result<usize, AnyError> {
+  async fn write(self: Rc<Self>, buf: &[u8]) -> Result<usize, std::io::Error> {
     let cancel_handle = RcRef::map(self.clone(), |this| &this.cancel_handle);
     async {
       let write = RcRef::map(self, |this| &this.write);
       let mut write = write.borrow_mut().await;
-      Ok(Pin::new(&mut *write).write(buf).await?)
+      Pin::new(&mut *write).write(buf).await
     }
     .try_or_cancel(cancel_handle)
     .await
@@ -1228,7 +1295,7 @@ impl UpgradeStream {
     self: Rc<Self>,
     buf1: &[u8],
     buf2: &[u8],
-  ) -> Result<usize, AnyError> {
+  ) -> Result<usize, std::io::Error> {
     let mut wr = RcRef::map(self, |r| &r.write).borrow_mut().await;
 
     let total = buf1.len() + buf2.len();
@@ -1281,9 +1348,12 @@ pub async fn op_raw_write_vectored(
   #[smi] rid: ResourceId,
   #[buffer] buf1: JsBuffer,
   #[buffer] buf2: JsBuffer,
-) -> Result<usize, AnyError> {
-  let resource: Rc<UpgradeStream> =
-    state.borrow().resource_table.get::<UpgradeStream>(rid)?;
+) -> Result<usize, HttpNextError> {
+  let resource: Rc<UpgradeStream> = state
+    .borrow()
+    .resource_table
+    .get::<UpgradeStream>(rid)
+    .map_err(HttpNextError::Resource)?;
   let nwritten = resource.write_vectored(&buf1, &buf2).await?;
   Ok(nwritten)
 }
diff --git a/ext/http/lib.rs b/ext/http/lib.rs
index 934f8a0024..49893b1b92 100644
--- a/ext/http/lib.rs
+++ b/ext/http/lib.rs
@@ -6,8 +6,6 @@ use async_compression::Level;
 use base64::prelude::BASE64_STANDARD;
 use base64::Engine;
 use cache_control::CacheControl;
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
 use deno_core::futures::channel::mpsc;
 use deno_core::futures::channel::oneshot;
 use deno_core::futures::future::pending;
@@ -89,11 +87,14 @@ mod service;
 mod websocket_upgrade;
 
 use fly_accept_encoding::Encoding;
+pub use http_next::HttpNextError;
 pub use request_properties::DefaultHttpPropertyExtractor;
 pub use request_properties::HttpConnectionProperties;
 pub use request_properties::HttpListenProperties;
 pub use request_properties::HttpPropertyExtractor;
 pub use request_properties::HttpRequestProperties;
+pub use service::UpgradeUnavailableError;
+pub use websocket_upgrade::WebSocketUpgradeError;
 
 deno_core::extension!(
   deno_http,
@@ -111,7 +112,9 @@ deno_core::extension!(
     http_next::op_http_close_after_finish,
     http_next::op_http_get_request_header,
     http_next::op_http_get_request_headers,
+    http_next::op_http_request_on_cancel,
     http_next::op_http_get_request_method_and_url<HTTP>,
+    http_next::op_http_get_request_cancelled,
     http_next::op_http_read_request_body,
     http_next::op_http_serve_on<HTTP>,
     http_next::op_http_serve<HTTP>,
@@ -134,6 +137,38 @@ deno_core::extension!(
   esm = ["00_serve.ts", "01_http.js", "02_websocket.ts"],
 );
 
+#[derive(Debug, thiserror::Error)]
+pub enum HttpError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  Canceled(#[from] deno_core::Canceled),
+  #[error("{0}")]
+  HyperV014(#[source] Arc<hyper_v014::Error>),
+  #[error("{0}")]
+  InvalidHeaderName(#[from] hyper_v014::header::InvalidHeaderName),
+  #[error("{0}")]
+  InvalidHeaderValue(#[from] hyper_v014::header::InvalidHeaderValue),
+  #[error("{0}")]
+  Http(#[from] hyper_v014::http::Error),
+  #[error("response headers already sent")]
+  ResponseHeadersAlreadySent,
+  #[error("connection closed while sending response")]
+  ConnectionClosedWhileSendingResponse,
+  #[error("already in use")]
+  AlreadyInUse,
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[error("no response headers")]
+  NoResponseHeaders,
+  #[error("response already completed")]
+  ResponseAlreadyCompleted,
+  #[error("cannot upgrade because request body was used")]
+  UpgradeBodyUsed,
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
 pub enum HttpSocketAddr {
   IpSocket(std::net::SocketAddr),
   #[cfg(unix)]
@@ -216,7 +251,7 @@ impl HttpConnResource {
       String,
       String,
     )>,
-    AnyError,
+    HttpError,
   > {
     let fut = async {
       let (request_tx, request_rx) = oneshot::channel();
@@ -259,8 +294,8 @@ impl HttpConnResource {
   }
 
   /// A future that completes when this HTTP connection is closed or errors.
-  async fn closed(&self) -> Result<(), AnyError> {
-    self.closed_fut.clone().map_err(AnyError::from).await
+  async fn closed(&self) -> Result<(), HttpError> {
+    self.closed_fut.clone().map_err(HttpError::HyperV014).await
   }
 }
 
@@ -280,14 +315,13 @@ pub fn http_create_conn_resource<S, A>(
   io: S,
   addr: A,
   scheme: &'static str,
-) -> Result<ResourceId, AnyError>
+) -> ResourceId
 where
   S: AsyncRead + AsyncWrite + Unpin + Send + 'static,
   A: Into<HttpSocketAddr>,
 {
   let conn = HttpConnResource::new(io, scheme, addr.into());
-  let rid = state.resource_table.add(conn);
-  Ok(rid)
+  state.resource_table.add(conn)
 }
 
 /// An object that implements the `hyper::Service` trait, through which Hyper
@@ -423,7 +457,9 @@ impl Resource for HttpStreamReadResource {
             // safely call `await` on it without creating a race condition.
             Some(_) => match body.as_mut().next().await.unwrap() {
               Ok(chunk) => assert!(chunk.is_empty()),
-              Err(err) => break Err(AnyError::from(err)),
+              Err(err) => {
+                break Err(HttpError::HyperV014(Arc::new(err)).into())
+              }
             },
             None => break Ok(BufView::empty()),
           }
@@ -545,8 +581,12 @@ struct NextRequestResponse(
 async fn op_http_accept(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<Option<NextRequestResponse>, AnyError> {
-  let conn = state.borrow().resource_table.get::<HttpConnResource>(rid)?;
+) -> Result<Option<NextRequestResponse>, HttpError> {
+  let conn = state
+    .borrow()
+    .resource_table
+    .get::<HttpConnResource>(rid)
+    .map_err(HttpError::Resource)?;
 
   match conn.accept().await {
     Ok(Some((read_stream, write_stream, method, url))) => {
@@ -657,11 +697,12 @@ async fn op_http_write_headers(
   #[smi] status: u16,
   #[serde] headers: Vec<(ByteString, ByteString)>,
   #[serde] data: Option<StringOrBuffer>,
-) -> Result<(), AnyError> {
+) -> Result<(), HttpError> {
   let stream = state
     .borrow_mut()
     .resource_table
-    .get::<HttpStreamWriteResource>(rid)?;
+    .get::<HttpStreamWriteResource>(rid)
+    .map_err(HttpError::Resource)?;
 
   // Track supported encoding
   let encoding = stream.accept_encoding;
@@ -708,14 +749,14 @@ async fn op_http_write_headers(
   let mut old_wr = RcRef::map(&stream, |r| &r.wr).borrow_mut().await;
   let response_tx = match replace(&mut *old_wr, new_wr) {
     HttpResponseWriter::Headers(response_tx) => response_tx,
-    _ => return Err(http_error("response headers already sent")),
+    _ => return Err(HttpError::ResponseHeadersAlreadySent),
   };
 
   match response_tx.send(body) {
     Ok(_) => Ok(()),
     Err(_) => {
       stream.conn.closed().await?;
-      Err(http_error("connection closed while sending response"))
+      Err(HttpError::ConnectionClosedWhileSendingResponse)
     }
   }
 }
@@ -725,11 +766,14 @@ async fn op_http_write_headers(
 fn op_http_headers(
   state: &mut OpState,
   #[smi] rid: u32,
-) -> Result<Vec<(ByteString, ByteString)>, AnyError> {
-  let stream = state.resource_table.get::<HttpStreamReadResource>(rid)?;
+) -> Result<Vec<(ByteString, ByteString)>, HttpError> {
+  let stream = state
+    .resource_table
+    .get::<HttpStreamReadResource>(rid)
+    .map_err(HttpError::Resource)?;
   let rd = RcRef::map(&stream, |r| &r.rd)
     .try_borrow()
-    .ok_or_else(|| http_error("already in use"))?;
+    .ok_or(HttpError::AlreadyInUse)?;
   match &*rd {
     HttpRequestReader::Headers(request) => Ok(req_headers(request.headers())),
     HttpRequestReader::Body(headers, _) => Ok(req_headers(headers)),
@@ -741,7 +785,7 @@ fn http_response(
   data: Option<StringOrBuffer>,
   compressing: bool,
   encoding: Encoding,
-) -> Result<(HttpResponseWriter, hyper_v014::Body), AnyError> {
+) -> Result<(HttpResponseWriter, hyper_v014::Body), HttpError> {
   // Gzip, after level 1, doesn't produce significant size difference.
   // This default matches nginx default gzip compression level (1):
   // https://nginx.org/en/docs/http/ngx_http_gzip_module.html#gzip_comp_level
@@ -878,25 +922,34 @@ async fn op_http_write_resource(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[smi] stream: ResourceId,
-) -> Result<(), AnyError> {
+) -> Result<(), HttpError> {
   let http_stream = state
     .borrow()
     .resource_table
-    .get::<HttpStreamWriteResource>(rid)?;
+    .get::<HttpStreamWriteResource>(rid)
+    .map_err(HttpError::Resource)?;
   let mut wr = RcRef::map(&http_stream, |r| &r.wr).borrow_mut().await;
-  let resource = state.borrow().resource_table.get_any(stream)?;
+  let resource = state
+    .borrow()
+    .resource_table
+    .get_any(stream)
+    .map_err(HttpError::Resource)?;
   loop {
     match *wr {
       HttpResponseWriter::Headers(_) => {
-        return Err(http_error("no response headers"))
+        return Err(HttpError::NoResponseHeaders)
       }
       HttpResponseWriter::Closed => {
-        return Err(http_error("response already completed"))
+        return Err(HttpError::ResponseAlreadyCompleted)
       }
       _ => {}
     };
 
-    let view = resource.clone().read(64 * 1024).await?; // 64KB
+    let view = resource
+      .clone()
+      .read(64 * 1024)
+      .await
+      .map_err(HttpError::Other)?; // 64KB
     if view.is_empty() {
       break;
     }
@@ -937,16 +990,17 @@ async fn op_http_write(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[buffer] buf: JsBuffer,
-) -> Result<(), AnyError> {
+) -> Result<(), HttpError> {
   let stream = state
     .borrow()
     .resource_table
-    .get::<HttpStreamWriteResource>(rid)?;
+    .get::<HttpStreamWriteResource>(rid)
+    .map_err(HttpError::Resource)?;
   let mut wr = RcRef::map(&stream, |r| &r.wr).borrow_mut().await;
 
   match &mut *wr {
-    HttpResponseWriter::Headers(_) => Err(http_error("no response headers")),
-    HttpResponseWriter::Closed => Err(http_error("response already completed")),
+    HttpResponseWriter::Headers(_) => Err(HttpError::NoResponseHeaders),
+    HttpResponseWriter::Closed => Err(HttpError::ResponseAlreadyCompleted),
     HttpResponseWriter::Body { writer, .. } => {
       let mut result = writer.write_all(&buf).await;
       if result.is_ok() {
@@ -961,7 +1015,7 @@ async fn op_http_write(
           stream.conn.closed().await?;
           // If there was no connection error, drop body_tx.
           *wr = HttpResponseWriter::Closed;
-          Err(http_error("response already completed"))
+          Err(HttpError::ResponseAlreadyCompleted)
         }
       }
     }
@@ -975,7 +1029,7 @@ async fn op_http_write(
           stream.conn.closed().await?;
           // If there was no connection error, drop body_tx.
           *wr = HttpResponseWriter::Closed;
-          Err(http_error("response already completed"))
+          Err(HttpError::ResponseAlreadyCompleted)
         }
       }
     }
@@ -989,11 +1043,12 @@ async fn op_http_write(
 async fn op_http_shutdown(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
+) -> Result<(), HttpError> {
   let stream = state
     .borrow()
     .resource_table
-    .get::<HttpStreamWriteResource>(rid)?;
+    .get::<HttpStreamWriteResource>(rid)
+    .map_err(HttpError::Resource)?;
   let mut wr = RcRef::map(&stream, |r| &r.wr).borrow_mut().await;
   let wr = take(&mut *wr);
   match wr {
@@ -1022,14 +1077,12 @@ async fn op_http_shutdown(
 
 #[op2]
 #[string]
-fn op_http_websocket_accept_header(
-  #[string] key: String,
-) -> Result<String, AnyError> {
+fn op_http_websocket_accept_header(#[string] key: String) -> String {
   let digest = ring::digest::digest(
     &ring::digest::SHA1_FOR_LEGACY_USE_ONLY,
     format!("{key}258EAFA5-E914-47DA-95CA-C5AB0DC85B11").as_bytes(),
   );
-  Ok(BASE64_STANDARD.encode(digest))
+  BASE64_STANDARD.encode(digest)
 }
 
 #[op2(async)]
@@ -1037,25 +1090,29 @@ fn op_http_websocket_accept_header(
 async fn op_http_upgrade_websocket(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, HttpError> {
   let stream = state
     .borrow_mut()
     .resource_table
-    .get::<HttpStreamReadResource>(rid)?;
+    .get::<HttpStreamReadResource>(rid)
+    .map_err(HttpError::Resource)?;
   let mut rd = RcRef::map(&stream, |r| &r.rd).borrow_mut().await;
 
   let request = match &mut *rd {
     HttpRequestReader::Headers(request) => request,
-    _ => {
-      return Err(http_error("cannot upgrade because request body was used"))
-    }
+    _ => return Err(HttpError::UpgradeBodyUsed),
   };
 
-  let (transport, bytes) =
-    extract_network_stream(hyper_v014::upgrade::on(request).await?);
-  let ws_rid =
-    ws_create_server_stream(&mut state.borrow_mut(), transport, bytes)?;
-  Ok(ws_rid)
+  let (transport, bytes) = extract_network_stream(
+    hyper_v014::upgrade::on(request)
+      .await
+      .map_err(|err| HttpError::HyperV014(Arc::new(err)))?,
+  );
+  Ok(ws_create_server_stream(
+    &mut state.borrow_mut(),
+    transport,
+    bytes,
+  ))
 }
 
 // Needed so hyper can use non Send futures
@@ -1082,10 +1139,6 @@ where
   }
 }
 
-fn http_error(message: &'static str) -> AnyError {
-  custom_error("Http", message)
-}
-
 /// Filters out the ever-surprising 'shutdown ENOTCONN' errors.
 fn filter_enotconn(
   result: Result<(), hyper_v014::Error>,
diff --git a/ext/http/request_body.rs b/ext/http/request_body.rs
index 45df12457c..f1c3f358ea 100644
--- a/ext/http/request_body.rs
+++ b/ext/http/request_body.rs
@@ -1,9 +1,9 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 use bytes::Bytes;
-use deno_core::error::AnyError;
 use deno_core::futures::stream::Peekable;
 use deno_core::futures::Stream;
 use deno_core::futures::StreamExt;
+use deno_core::futures::TryFutureExt;
 use deno_core::AsyncRefCell;
 use deno_core::AsyncResult;
 use deno_core::BufView;
@@ -22,7 +22,7 @@ use std::task::Poll;
 struct ReadFuture(Incoming);
 
 impl Stream for ReadFuture {
-  type Item = Result<Bytes, AnyError>;
+  type Item = Result<Bytes, hyper::Error>;
 
   fn poll_next(
     self: Pin<&mut Self>,
@@ -37,13 +37,13 @@ impl Stream for ReadFuture {
           if let Ok(data) = frame.into_data() {
             // Ensure that we never yield an empty frame
             if !data.is_empty() {
-              break Poll::Ready(Some(Ok::<_, AnyError>(data)));
+              break Poll::Ready(Some(Ok(data)));
             }
           }
           // Loop again so we don't lose the waker
           continue;
         }
-        Some(Err(e)) => Poll::Ready(Some(Err(e.into()))),
+        Some(Err(e)) => Poll::Ready(Some(Err(e))),
         None => Poll::Ready(None),
       };
     }
@@ -58,7 +58,7 @@ impl HttpRequestBody {
     Self(AsyncRefCell::new(ReadFuture(body).peekable()), size_hint)
   }
 
-  async fn read(self: Rc<Self>, limit: usize) -> Result<BufView, AnyError> {
+  async fn read(self: Rc<Self>, limit: usize) -> Result<BufView, hyper::Error> {
     let peekable = RcRef::map(self, |this| &this.0);
     let mut peekable = peekable.borrow_mut().await;
     match Pin::new(&mut *peekable).peek_mut().await {
@@ -82,7 +82,7 @@ impl Resource for HttpRequestBody {
   }
 
   fn read(self: Rc<Self>, limit: usize) -> AsyncResult<BufView> {
-    Box::pin(HttpRequestBody::read(self, limit))
+    Box::pin(HttpRequestBody::read(self, limit).map_err(Into::into))
   }
 
   fn size_hint(&self) -> (u64, Option<u64>) {
diff --git a/ext/http/request_properties.rs b/ext/http/request_properties.rs
index 1422c7417d..39d35a79f1 100644
--- a/ext/http/request_properties.rs
+++ b/ext/http/request_properties.rs
@@ -34,8 +34,8 @@ pub struct HttpConnectionProperties {
   pub stream_type: NetworkStreamType,
 }
 
-pub struct HttpRequestProperties {
-  pub authority: Option<String>,
+pub struct HttpRequestProperties<'a> {
+  pub authority: Option<Cow<'a, str>>,
 }
 
 /// Pluggable trait to determine listen, connection and request properties
@@ -84,11 +84,11 @@ pub trait HttpPropertyExtractor {
   ) -> NetworkStream;
 
   /// Determines the request properties.
-  fn request_properties(
-    connection_properties: &HttpConnectionProperties,
-    uri: &Uri,
-    headers: &HeaderMap,
-  ) -> HttpRequestProperties;
+  fn request_properties<'a>(
+    connection_properties: &'a HttpConnectionProperties,
+    uri: &'a Uri,
+    headers: &'a HeaderMap,
+  ) -> HttpRequestProperties<'a>;
 }
 
 pub struct DefaultHttpPropertyExtractor {}
@@ -180,18 +180,17 @@ impl HttpPropertyExtractor for DefaultHttpPropertyExtractor {
     }
   }
 
-  fn request_properties(
-    connection_properties: &HttpConnectionProperties,
-    uri: &Uri,
-    headers: &HeaderMap,
-  ) -> HttpRequestProperties {
+  fn request_properties<'a>(
+    connection_properties: &'a HttpConnectionProperties,
+    uri: &'a Uri,
+    headers: &'a HeaderMap,
+  ) -> HttpRequestProperties<'a> {
     let authority = req_host(
       uri,
       headers,
       connection_properties.stream_type,
       connection_properties.local_port.unwrap_or_default(),
-    )
-    .map(|s| s.into_owned());
+    );
 
     HttpRequestProperties { authority }
   }
diff --git a/ext/http/service.rs b/ext/http/service.rs
index 787e9babf8..ce24dea43f 100644
--- a/ext/http/service.rs
+++ b/ext/http/service.rs
@@ -2,7 +2,6 @@
 use crate::request_properties::HttpConnectionProperties;
 use crate::response_body::ResponseBytesInner;
 use crate::response_body::ResponseStreamResult;
-use deno_core::error::AnyError;
 use deno_core::futures::ready;
 use deno_core::BufView;
 use deno_core::OpState;
@@ -28,6 +27,7 @@ use std::rc::Rc;
 use std::task::Context;
 use std::task::Poll;
 use std::task::Waker;
+use tokio::sync::oneshot;
 
 pub type Request = hyper::Request<Incoming>;
 pub type Response = hyper::Response<HttpRecordResponse>;
@@ -206,8 +206,13 @@ pub(crate) async fn handle_request(
   Ok(response)
 }
 
+#[derive(Debug, thiserror::Error)]
+#[error("upgrade unavailable")]
+pub struct UpgradeUnavailableError;
+
 struct HttpRecordInner {
   server_state: SignallingRc<HttpServerState>,
+  closed_channel: Option<oneshot::Sender<()>>,
   request_info: HttpConnectionProperties,
   request_parts: http::request::Parts,
   request_body: Option<RequestBodyState>,
@@ -273,6 +278,7 @@ impl HttpRecord {
       response_body_finished: false,
       response_body_waker: None,
       trailers: None,
+      closed_channel: None,
       been_dropped: false,
       finished: false,
       needs_close_after_finish: false,
@@ -309,6 +315,10 @@ impl HttpRecord {
     RefMut::map(self.self_mut(), |inner| &mut inner.needs_close_after_finish)
   }
 
+  pub fn on_cancel(&self, sender: oneshot::Sender<()>) {
+    self.self_mut().closed_channel = Some(sender);
+  }
+
   fn recycle(self: Rc<Self>) {
     assert!(
       Rc::strong_count(&self) == 1,
@@ -344,14 +354,14 @@ impl HttpRecord {
   }
 
   /// Perform the Hyper upgrade on this record.
-  pub fn upgrade(&self) -> Result<OnUpgrade, AnyError> {
+  pub fn upgrade(&self) -> Result<OnUpgrade, UpgradeUnavailableError> {
     // Manually perform the upgrade. We're peeking into hyper's underlying machinery here a bit
     self
       .self_mut()
       .request_parts
       .extensions
       .remove::<OnUpgrade>()
-      .ok_or_else(|| AnyError::msg("upgrade unavailable"))
+      .ok_or(UpgradeUnavailableError)
   }
 
   /// Take the Hyper body from this record.
@@ -387,6 +397,9 @@ impl HttpRecord {
     inner.been_dropped = true;
     // The request body might include actual resources.
     inner.request_body.take();
+    if let Some(closed_channel) = inner.closed_channel.take() {
+      let _ = closed_channel.send(());
+    }
   }
 
   /// Complete this record, potentially expunging it if it is fully complete (ie: cancelled as well).
@@ -515,7 +528,7 @@ pub struct HttpRecordResponse(ManuallyDrop<Rc<HttpRecord>>);
 
 impl Body for HttpRecordResponse {
   type Data = BufView;
-  type Error = AnyError;
+  type Error = deno_core::error::AnyError;
 
   fn poll_frame(
     self: Pin<&mut Self>,
@@ -640,7 +653,7 @@ mod tests {
   }
 
   #[tokio::test]
-  async fn test_handle_request() -> Result<(), AnyError> {
+  async fn test_handle_request() -> Result<(), deno_core::error::AnyError> {
     let (tx, mut rx) = tokio::sync::mpsc::channel(10);
     let server_state = HttpServerState::new();
     let server_state_check = server_state.clone();
diff --git a/ext/http/websocket_upgrade.rs b/ext/http/websocket_upgrade.rs
index 4dead767a3..af9504717e 100644
--- a/ext/http/websocket_upgrade.rs
+++ b/ext/http/websocket_upgrade.rs
@@ -4,7 +4,6 @@ use std::marker::PhantomData;
 
 use bytes::Bytes;
 use bytes::BytesMut;
-use deno_core::error::AnyError;
 use httparse::Status;
 use hyper::header::HeaderName;
 use hyper::header::HeaderValue;
@@ -13,12 +12,30 @@ use memmem::Searcher;
 use memmem::TwoWaySearcher;
 use once_cell::sync::OnceCell;
 
-use crate::http_error;
+#[derive(Debug, thiserror::Error)]
+pub enum WebSocketUpgradeError {
+  #[error("invalid headers")]
+  InvalidHeaders,
+  #[error("{0}")]
+  HttpParse(#[from] httparse::Error),
+  #[error("{0}")]
+  Http(#[from] http::Error),
+  #[error("{0}")]
+  Utf8(#[from] std::str::Utf8Error),
+  #[error("{0}")]
+  InvalidHeaderName(#[from] http::header::InvalidHeaderName),
+  #[error("{0}")]
+  InvalidHeaderValue(#[from] http::header::InvalidHeaderValue),
+  #[error("invalid HTTP status line")]
+  InvalidHttpStatusLine,
+  #[error("attempted to write to completed upgrade buffer")]
+  UpgradeBufferAlreadyCompleted,
+}
 
 /// Given a buffer that ends in `\n\n` or `\r\n\r\n`, returns a parsed [`Request<Body>`].
 fn parse_response<T: Default>(
   header_bytes: &[u8],
-) -> Result<(usize, Response<T>), AnyError> {
+) -> Result<(usize, Response<T>), WebSocketUpgradeError> {
   let mut headers = [httparse::EMPTY_HEADER; 16];
   let status = httparse::parse_headers(header_bytes, &mut headers)?;
   match status {
@@ -32,7 +49,7 @@ fn parse_response<T: Default>(
       }
       Ok((index, resp))
     }
-    _ => Err(http_error("invalid headers")),
+    _ => Err(WebSocketUpgradeError::InvalidHeaders),
   }
 }
 
@@ -69,11 +86,14 @@ pub struct WebSocketUpgrade<T: Default> {
 impl<T: Default> WebSocketUpgrade<T> {
   /// Ensures that the status line starts with "HTTP/1.1 101 " which matches all of the node.js
   /// WebSocket libraries that are known. We don't care about the trailing status text.
-  fn validate_status(&self, status: &[u8]) -> Result<(), AnyError> {
+  fn validate_status(
+    &self,
+    status: &[u8],
+  ) -> Result<(), WebSocketUpgradeError> {
     if status.starts_with(b"HTTP/1.1 101 ") {
       Ok(())
     } else {
-      Err(http_error("invalid HTTP status line"))
+      Err(WebSocketUpgradeError::InvalidHttpStatusLine)
     }
   }
 
@@ -82,7 +102,7 @@ impl<T: Default> WebSocketUpgrade<T> {
   pub fn write(
     &mut self,
     bytes: &[u8],
-  ) -> Result<Option<(Response<T>, Bytes)>, AnyError> {
+  ) -> Result<Option<(Response<T>, Bytes)>, WebSocketUpgradeError> {
     use WebSocketUpgradeState::*;
 
     match self.state {
@@ -142,9 +162,7 @@ impl<T: Default> WebSocketUpgrade<T> {
           Ok(None)
         }
       }
-      Complete => {
-        Err(http_error("attempted to write to completed upgrade buffer"))
-      }
+      Complete => Err(WebSocketUpgradeError::UpgradeBufferAlreadyCompleted),
     }
   }
 }
@@ -157,8 +175,8 @@ mod tests {
   type ExpectedResponseAndHead = Option<(Response<Body>, &'static [u8])>;
 
   fn assert_response(
-    result: Result<Option<(Response<Body>, Bytes)>, AnyError>,
-    expected: Result<ExpectedResponseAndHead, &'static str>,
+    result: Result<Option<(Response<Body>, Bytes)>, WebSocketUpgradeError>,
+    expected: Result<ExpectedResponseAndHead, WebSocketUpgradeError>,
     chunk_info: Option<(usize, usize)>,
   ) {
     let formatted = format!("{result:?}");
@@ -189,8 +207,8 @@ mod tests {
         "Expected Ok(None), was {formatted}",
       ),
       Err(e) => assert_eq!(
-        e,
-        result.err().map(|e| format!("{e:?}")).unwrap_or_default(),
+        format!("{e:?}"),
+        format!("{:?}", result.unwrap_err()),
         "Expected error, was {formatted}",
       ),
     }
@@ -198,7 +216,7 @@ mod tests {
 
   fn validate_upgrade_all_at_once(
     s: &str,
-    expected: Result<ExpectedResponseAndHead, &'static str>,
+    expected: Result<ExpectedResponseAndHead, WebSocketUpgradeError>,
   ) {
     let mut upgrade = WebSocketUpgrade::default();
     let res = upgrade.write(s.as_bytes());
@@ -209,7 +227,7 @@ mod tests {
   fn validate_upgrade_chunks(
     s: &str,
     size: usize,
-    expected: Result<ExpectedResponseAndHead, &'static str>,
+    expected: Result<ExpectedResponseAndHead, WebSocketUpgradeError>,
   ) {
     let chunk_info = Some((s.as_bytes().len(), size));
     let mut upgrade = WebSocketUpgrade::default();
@@ -226,7 +244,7 @@ mod tests {
 
   fn validate_upgrade(
     s: &str,
-    expected: fn() -> Result<ExpectedResponseAndHead, &'static str>,
+    expected: fn() -> Result<ExpectedResponseAndHead, WebSocketUpgradeError>,
   ) {
     validate_upgrade_all_at_once(s, expected());
     validate_upgrade_chunks(s, 1, expected());
@@ -315,7 +333,7 @@ mod tests {
   #[test]
   fn upgrade_invalid_status() {
     validate_upgrade("HTTP/1.1 200 OK\nConnection: Upgrade\n\n", || {
-      Err("invalid HTTP status line")
+      Err(WebSocketUpgradeError::InvalidHttpStatusLine)
     });
   }
 
@@ -327,7 +345,11 @@ mod tests {
       .join("\n");
     validate_upgrade(
       &format!("HTTP/1.1 101 Switching Protocols\n{headers}\n\n"),
-      || Err("too many headers"),
+      || {
+        Err(WebSocketUpgradeError::HttpParse(
+          httparse::Error::TooManyHeaders,
+        ))
+      },
     );
   }
 }
diff --git a/ext/io/Cargo.toml b/ext/io/Cargo.toml
index 22c346764b..6ef049ff9b 100644
--- a/ext/io/Cargo.toml
+++ b/ext/io/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_io"
-version = "0.78.0"
+version = "0.87.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/io/bi_pipe.rs b/ext/io/bi_pipe.rs
index 402e383ac9..3492e2f441 100644
--- a/ext/io/bi_pipe.rs
+++ b/ext/io/bi_pipe.rs
@@ -2,7 +2,6 @@
 
 use std::rc::Rc;
 
-use deno_core::error::AnyError;
 use deno_core::AsyncRefCell;
 use deno_core::AsyncResult;
 use deno_core::CancelHandle;
@@ -71,13 +70,16 @@ impl BiPipeResource {
   pub async fn read(
     self: Rc<Self>,
     data: &mut [u8],
-  ) -> Result<usize, AnyError> {
+  ) -> Result<usize, std::io::Error> {
     let mut rd = RcRef::map(&self, |r| &r.read_half).borrow_mut().await;
     let cancel_handle = RcRef::map(&self, |r| &r.cancel);
-    Ok(rd.read(data).try_or_cancel(cancel_handle).await?)
+    rd.read(data).try_or_cancel(cancel_handle).await
   }
 
-  pub async fn write(self: Rc<Self>, data: &[u8]) -> Result<usize, AnyError> {
+  pub async fn write(
+    self: Rc<Self>,
+    data: &[u8],
+  ) -> Result<usize, std::io::Error> {
     let mut wr = RcRef::map(self, |r| &r.write_half).borrow_mut().await;
     let nwritten = wr.write(data).await?;
     wr.flush().await?;
@@ -181,9 +183,10 @@ fn from_raw(
 ) -> Result<(BiPipeRead, BiPipeWrite), std::io::Error> {
   use std::os::fd::FromRawFd;
   // Safety: The fd is part of a pair of connected sockets
-  let unix_stream = tokio::net::UnixStream::from_std(unsafe {
-    std::os::unix::net::UnixStream::from_raw_fd(stream)
-  })?;
+  let unix_stream =
+    unsafe { std::os::unix::net::UnixStream::from_raw_fd(stream) };
+  unix_stream.set_nonblocking(true)?;
+  let unix_stream = tokio::net::UnixStream::from_std(unix_stream)?;
   let (read, write) = unix_stream.into_split();
   Ok((BiPipeRead { inner: read }, BiPipeWrite { inner: write }))
 }
@@ -270,15 +273,15 @@ impl_async_write!(for BiPipe -> self.write_end);
 
 /// Creates both sides of a bidirectional pipe, returning the raw
 /// handles to the underlying OS resources.
-pub fn bi_pipe_pair_raw() -> Result<(RawBiPipeHandle, RawBiPipeHandle), AnyError>
-{
+pub fn bi_pipe_pair_raw(
+) -> Result<(RawBiPipeHandle, RawBiPipeHandle), std::io::Error> {
   #[cfg(unix)]
   {
     // SockFlag is broken on macOS
     // https://github.com/nix-rust/nix/issues/861
     let mut fds = [-1, -1];
     #[cfg(not(target_os = "macos"))]
-    let flags = libc::SOCK_CLOEXEC | libc::SOCK_NONBLOCK;
+    let flags = libc::SOCK_CLOEXEC;
 
     #[cfg(target_os = "macos")]
     let flags = 0;
@@ -293,19 +296,19 @@ pub fn bi_pipe_pair_raw() -> Result<(RawBiPipeHandle, RawBiPipeHandle), AnyError
       )
     };
     if ret != 0 {
-      return Err(std::io::Error::last_os_error().into());
+      return Err(std::io::Error::last_os_error());
     }
 
     if cfg!(target_os = "macos") {
       let fcntl = |fd: i32, flag: libc::c_int| -> Result<(), std::io::Error> {
         // SAFETY: libc call, fd is valid
-        let flags = unsafe { libc::fcntl(fd, libc::F_GETFL) };
+        let flags = unsafe { libc::fcntl(fd, libc::F_GETFD) };
 
         if flags == -1 {
           return Err(fail(fds));
         }
         // SAFETY: libc call, fd is valid
-        let ret = unsafe { libc::fcntl(fd, libc::F_SETFL, flags | flag) };
+        let ret = unsafe { libc::fcntl(fd, libc::F_SETFD, flags | flag) };
         if ret == -1 {
           return Err(fail(fds));
         }
@@ -321,13 +324,9 @@ pub fn bi_pipe_pair_raw() -> Result<(RawBiPipeHandle, RawBiPipeHandle), AnyError
         std::io::Error::last_os_error()
       }
 
-      // SOCK_NONBLOCK is not supported on macOS.
-      (fcntl)(fds[0], libc::O_NONBLOCK)?;
-      (fcntl)(fds[1], libc::O_NONBLOCK)?;
-
       // SOCK_CLOEXEC is not supported on macOS.
-      (fcntl)(fds[0], libc::FD_CLOEXEC)?;
-      (fcntl)(fds[1], libc::FD_CLOEXEC)?;
+      fcntl(fds[0], libc::FD_CLOEXEC)?;
+      fcntl(fds[1], libc::FD_CLOEXEC)?;
     }
 
     let fd1 = fds[0];
@@ -389,7 +388,7 @@ pub fn bi_pipe_pair_raw() -> Result<(RawBiPipeHandle, RawBiPipeHandle), AnyError
             continue;
           }
 
-          return Err(err.into());
+          return Err(err);
         }
 
         break (path, hd1);
@@ -411,7 +410,7 @@ pub fn bi_pipe_pair_raw() -> Result<(RawBiPipeHandle, RawBiPipeHandle), AnyError
         0,
       );
       if hd2 == INVALID_HANDLE_VALUE {
-        return Err(io::Error::last_os_error().into());
+        return Err(io::Error::last_os_error());
       }
 
       // Will not block because we have create the pair.
@@ -419,7 +418,7 @@ pub fn bi_pipe_pair_raw() -> Result<(RawBiPipeHandle, RawBiPipeHandle), AnyError
         let err = std::io::Error::last_os_error();
         if err.raw_os_error() != Some(ERROR_PIPE_CONNECTED as i32) {
           CloseHandle(hd2);
-          return Err(err.into());
+          return Err(err);
         }
       }
 
diff --git a/ext/io/fs.rs b/ext/io/fs.rs
index 3798c1429d..7ef02315ba 100644
--- a/ext/io/fs.rs
+++ b/ext/io/fs.rs
@@ -1,15 +1,12 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 use std::borrow::Cow;
+use std::fmt::Formatter;
 use std::io;
 use std::rc::Rc;
 use std::time::SystemTime;
 use std::time::UNIX_EPOCH;
 
-use deno_core::error::custom_error;
-use deno_core::error::not_supported;
-use deno_core::error::resource_unavailable;
-use deno_core::error::AnyError;
 use deno_core::BufMutView;
 use deno_core::BufView;
 use deno_core::OpState;
@@ -25,6 +22,21 @@ pub enum FsError {
   NotCapable(&'static str),
 }
 
+impl std::fmt::Display for FsError {
+  fn fmt(&self, f: &mut Formatter<'_>) -> std::fmt::Result {
+    match self {
+      FsError::Io(err) => std::fmt::Display::fmt(err, f),
+      FsError::FileBusy => f.write_str("file busy"),
+      FsError::NotSupported => f.write_str("not supported"),
+      FsError::NotCapable(err) => {
+        f.write_str(&format!("requires {err} access"))
+      }
+    }
+  }
+}
+
+impl std::error::Error for FsError {}
+
 impl FsError {
   pub fn kind(&self) -> io::ErrorKind {
     match self {
@@ -59,19 +71,6 @@ impl From<io::ErrorKind> for FsError {
   }
 }
 
-impl From<FsError> for AnyError {
-  fn from(err: FsError) -> Self {
-    match err {
-      FsError::Io(err) => AnyError::from(err),
-      FsError::FileBusy => resource_unavailable(),
-      FsError::NotSupported => not_supported(),
-      FsError::NotCapable(err) => {
-        custom_error("NotCapable", format!("permission denied: {err}"))
-      }
-    }
-  }
-}
-
 impl From<JoinError> for FsError {
   fn from(err: JoinError) -> Self {
     if err.is_cancelled() {
@@ -95,6 +94,7 @@ pub struct FsStat {
   pub mtime: Option<u64>,
   pub atime: Option<u64>,
   pub birthtime: Option<u64>,
+  pub ctime: Option<u64>,
 
   pub dev: u64,
   pub ino: u64,
@@ -154,6 +154,16 @@ impl FsStat {
       }
     }
 
+    #[inline(always)]
+    fn get_ctime(ctime_or_0: i64) -> Option<u64> {
+      if ctime_or_0 > 0 {
+        // ctime return seconds since epoch, but we need milliseconds
+        return Some(ctime_or_0 as u64 * 1000);
+      }
+
+      None
+    }
+
     Self {
       is_file: metadata.is_file(),
       is_directory: metadata.is_dir(),
@@ -163,6 +173,7 @@ impl FsStat {
       mtime: to_msec(metadata.modified()),
       atime: to_msec(metadata.accessed()),
       birthtime: to_msec(metadata.created()),
+      ctime: get_ctime(unix_or_zero!(ctime)),
 
       dev: unix_or_zero!(dev),
       ino: unix_or_zero!(ino),
@@ -266,9 +277,9 @@ impl FileResource {
     state: &OpState,
     rid: ResourceId,
     f: F,
-  ) -> Result<R, AnyError>
+  ) -> Result<R, deno_core::error::AnyError>
   where
-    F: FnOnce(Rc<FileResource>) -> Result<R, AnyError>,
+    F: FnOnce(Rc<FileResource>) -> Result<R, deno_core::error::AnyError>,
   {
     let resource = state.resource_table.get::<FileResource>(rid)?;
     f(resource)
@@ -277,7 +288,7 @@ impl FileResource {
   pub fn get_file(
     state: &OpState,
     rid: ResourceId,
-  ) -> Result<Rc<dyn File>, AnyError> {
+  ) -> Result<Rc<dyn File>, deno_core::error::AnyError> {
     let resource = state.resource_table.get::<FileResource>(rid)?;
     Ok(resource.file())
   }
@@ -286,9 +297,9 @@ impl FileResource {
     state: &OpState,
     rid: ResourceId,
     f: F,
-  ) -> Result<R, AnyError>
+  ) -> Result<R, deno_core::error::AnyError>
   where
-    F: FnOnce(Rc<dyn File>) -> Result<R, AnyError>,
+    F: FnOnce(Rc<dyn File>) -> Result<R, deno_core::error::AnyError>,
   {
     Self::with_resource(state, rid, |r| f(r.file.clone()))
   }
@@ -303,10 +314,7 @@ impl deno_core::Resource for FileResource {
     Cow::Borrowed(&self.name)
   }
 
-  fn read(
-    self: Rc<Self>,
-    limit: usize,
-  ) -> deno_core::AsyncResult<deno_core::BufView> {
+  fn read(self: Rc<Self>, limit: usize) -> deno_core::AsyncResult<BufView> {
     Box::pin(async move {
       self
         .file
@@ -319,8 +327,8 @@ impl deno_core::Resource for FileResource {
 
   fn read_byob(
     self: Rc<Self>,
-    buf: deno_core::BufMutView,
-  ) -> deno_core::AsyncResult<(usize, deno_core::BufMutView)> {
+    buf: BufMutView,
+  ) -> deno_core::AsyncResult<(usize, BufMutView)> {
     Box::pin(async move {
       self
         .file
@@ -333,17 +341,14 @@ impl deno_core::Resource for FileResource {
 
   fn write(
     self: Rc<Self>,
-    buf: deno_core::BufView,
+    buf: BufView,
   ) -> deno_core::AsyncResult<deno_core::WriteOutcome> {
     Box::pin(async move {
       self.file.clone().write(buf).await.map_err(|err| err.into())
     })
   }
 
-  fn write_all(
-    self: Rc<Self>,
-    buf: deno_core::BufView,
-  ) -> deno_core::AsyncResult<()> {
+  fn write_all(self: Rc<Self>, buf: BufView) -> deno_core::AsyncResult<()> {
     Box::pin(async move {
       self
         .file
diff --git a/ext/io/lib.rs b/ext/io/lib.rs
index a07d64ae37..5d183aa464 100644
--- a/ext/io/lib.rs
+++ b/ext/io/lib.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::unsync::spawn_blocking;
 use deno_core::unsync::TaskQueue;
@@ -48,6 +47,7 @@ use winapi::um::processenv::GetStdHandle;
 #[cfg(windows)]
 use winapi::um::winbase;
 
+use deno_core::futures::TryFutureExt;
 #[cfg(windows)]
 use parking_lot::Condvar;
 #[cfg(windows)]
@@ -348,13 +348,13 @@ where
     RcRef::map(self, |r| &r.stream).borrow_mut()
   }
 
-  async fn write(self: Rc<Self>, data: &[u8]) -> Result<usize, AnyError> {
+  async fn write(self: Rc<Self>, data: &[u8]) -> Result<usize, io::Error> {
     let mut stream = self.borrow_mut().await;
     let nwritten = stream.write(data).await?;
     Ok(nwritten)
   }
 
-  async fn shutdown(self: Rc<Self>) -> Result<(), AnyError> {
+  async fn shutdown(self: Rc<Self>) -> Result<(), io::Error> {
     let mut stream = self.borrow_mut().await;
     stream.shutdown().await?;
     Ok(())
@@ -396,7 +396,7 @@ where
     self.cancel_handle.cancel()
   }
 
-  async fn read(self: Rc<Self>, data: &mut [u8]) -> Result<usize, AnyError> {
+  async fn read(self: Rc<Self>, data: &mut [u8]) -> Result<usize, io::Error> {
     let mut rd = self.borrow_mut().await;
     let nread = rd.read(data).try_or_cancel(self.cancel_handle()).await?;
     Ok(nread)
@@ -417,7 +417,7 @@ impl Resource for ChildStdinResource {
   deno_core::impl_writable!();
 
   fn shutdown(self: Rc<Self>) -> AsyncResult<()> {
-    Box::pin(self.shutdown())
+    Box::pin(self.shutdown().map_err(|e| e.into()))
   }
 }
 
@@ -1010,7 +1010,7 @@ pub fn op_print(
   state: &mut OpState,
   #[string] msg: &str,
   is_err: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), deno_core::error::AnyError> {
   let rid = if is_err { 2 } else { 1 };
   FileResource::with_file(state, rid, move |file| {
     Ok(file.write_all_sync(msg.as_bytes())?)
diff --git a/ext/kv/Cargo.toml b/ext/kv/Cargo.toml
index eee4762eb4..1d7b91770f 100644
--- a/ext/kv/Cargo.toml
+++ b/ext/kv/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_kv"
-version = "0.76.0"
+version = "0.85.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -21,6 +21,7 @@ bytes.workspace = true
 chrono = { workspace = true, features = ["now"] }
 deno_core.workspace = true
 deno_fetch.workspace = true
+deno_path_util.workspace = true
 deno_permissions.workspace = true
 deno_tls.workspace = true
 denokv_proto.workspace = true
@@ -35,6 +36,7 @@ prost.workspace = true
 rand.workspace = true
 rusqlite.workspace = true
 serde.workspace = true
+thiserror.workspace = true
 url.workspace = true
 
 [build-dependencies]
diff --git a/ext/kv/config.rs b/ext/kv/config.rs
index 6e2e2c3a1f..7166bcbcc2 100644
--- a/ext/kv/config.rs
+++ b/ext/kv/config.rs
@@ -1,16 +1,17 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
+#[derive(Clone, Copy, Debug)]
 pub struct KvConfig {
-  pub(crate) max_write_key_size_bytes: usize,
-  pub(crate) max_read_key_size_bytes: usize,
-  pub(crate) max_value_size_bytes: usize,
-  pub(crate) max_read_ranges: usize,
-  pub(crate) max_read_entries: usize,
-  pub(crate) max_checks: usize,
-  pub(crate) max_mutations: usize,
-  pub(crate) max_watched_keys: usize,
-  pub(crate) max_total_mutation_size_bytes: usize,
-  pub(crate) max_total_key_size_bytes: usize,
+  pub max_write_key_size_bytes: usize,
+  pub max_read_key_size_bytes: usize,
+  pub max_value_size_bytes: usize,
+  pub max_read_ranges: usize,
+  pub max_read_entries: usize,
+  pub max_checks: usize,
+  pub max_mutations: usize,
+  pub max_watched_keys: usize,
+  pub max_total_mutation_size_bytes: usize,
+  pub max_total_key_size_bytes: usize,
 }
 
 impl KvConfig {
diff --git a/ext/kv/lib.rs b/ext/kv/lib.rs
index 13e4f1662f..a4ccfe3d63 100644
--- a/ext/kv/lib.rs
+++ b/ext/kv/lib.rs
@@ -12,15 +12,11 @@ use std::num::NonZeroU32;
 use std::rc::Rc;
 use std::time::Duration;
 
-use anyhow::bail;
 use base64::prelude::BASE64_URL_SAFE;
 use base64::Engine;
 use chrono::DateTime;
 use chrono::Utc;
-use deno_core::anyhow::Context;
 use deno_core::error::get_custom_error_class;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::futures::StreamExt;
 use deno_core::op2;
 use deno_core::serde_v8::AnyValue;
@@ -118,12 +114,72 @@ impl Resource for DatabaseWatcherResource {
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum KvError {
+  #[error(transparent)]
+  DatabaseHandler(deno_core::error::AnyError),
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("Too many ranges (max {0})")]
+  TooManyRanges(usize),
+  #[error("Too many entries (max {0})")]
+  TooManyEntries(usize),
+  #[error("Too many checks (max {0})")]
+  TooManyChecks(usize),
+  #[error("Too many mutations (max {0})")]
+  TooManyMutations(usize),
+  #[error("Too many keys (max {0})")]
+  TooManyKeys(usize),
+  #[error("limit must be greater than 0")]
+  InvalidLimit,
+  #[error("Invalid boundary key")]
+  InvalidBoundaryKey,
+  #[error("Key too large for read (max {0} bytes)")]
+  KeyTooLargeToRead(usize),
+  #[error("Key too large for write (max {0} bytes)")]
+  KeyTooLargeToWrite(usize),
+  #[error("Total mutation size too large (max {0} bytes)")]
+  TotalMutationTooLarge(usize),
+  #[error("Total key size too large (max {0} bytes)")]
+  TotalKeyTooLarge(usize),
+  #[error(transparent)]
+  Kv(deno_core::error::AnyError),
+  #[error(transparent)]
+  Io(#[from] std::io::Error),
+  #[error("Queue message not found")]
+  QueueMessageNotFound,
+  #[error("Start key is not in the keyspace defined by prefix")]
+  StartKeyNotInKeyspace,
+  #[error("End key is not in the keyspace defined by prefix")]
+  EndKeyNotInKeyspace,
+  #[error("Start key is greater than end key")]
+  StartKeyGreaterThanEndKey,
+  #[error("Invalid check")]
+  InvalidCheck(#[source] KvCheckError),
+  #[error("Invalid mutation")]
+  InvalidMutation(#[source] KvMutationError),
+  #[error("Invalid enqueue")]
+  InvalidEnqueue(#[source] std::io::Error),
+  #[error("key cannot be empty")]
+  EmptyKey, // TypeError
+  #[error("Value too large (max {0} bytes)")]
+  ValueTooLarge(usize), // TypeError
+  #[error("enqueue payload too large (max {0} bytes)")]
+  EnqueuePayloadTooLarge(usize), // TypeError
+  #[error("invalid cursor")]
+  InvalidCursor,
+  #[error("cursor out of bounds")]
+  CursorOutOfBounds,
+  #[error("Invalid range")]
+  InvalidRange,
+}
+
 #[op2(async)]
 #[smi]
 async fn op_kv_database_open<DBH>(
   state: Rc<RefCell<OpState>>,
   #[string] path: Option<String>,
-) -> Result<ResourceId, AnyError>
+) -> Result<ResourceId, KvError>
 where
   DBH: DatabaseHandler + 'static,
 {
@@ -134,7 +190,10 @@ where
       .check_or_exit(UNSTABLE_FEATURE_NAME, "Deno.openKv");
     state.borrow::<Rc<DBH>>().clone()
   };
-  let db = handler.open(state.clone(), path).await?;
+  let db = handler
+    .open(state.clone(), path)
+    .await
+    .map_err(KvError::DatabaseHandler)?;
   let rid = state.borrow_mut().resource_table.add(DatabaseResource {
     db,
     cancel_handle: CancelHandle::new_rc(),
@@ -184,8 +243,8 @@ enum ToV8Value {
 }
 
 impl TryFrom<FromV8Value> for KvValue {
-  type Error = AnyError;
-  fn try_from(value: FromV8Value) -> Result<Self, AnyError> {
+  type Error = num_bigint::TryFromBigIntError<num_bigint::BigInt>;
+  fn try_from(value: FromV8Value) -> Result<Self, Self::Error> {
     Ok(match value {
       FromV8Value::V8(buf) => KvValue::V8(buf.to_vec()),
       FromV8Value::Bytes(buf) => KvValue::Bytes(buf.to_vec()),
@@ -214,8 +273,8 @@ struct ToV8KvEntry {
 }
 
 impl TryFrom<KvEntry> for ToV8KvEntry {
-  type Error = AnyError;
-  fn try_from(entry: KvEntry) -> Result<Self, AnyError> {
+  type Error = std::io::Error;
+  fn try_from(entry: KvEntry) -> Result<Self, Self::Error> {
     Ok(ToV8KvEntry {
       key: decode_key(&entry.key)?
         .0
@@ -261,14 +320,16 @@ async fn op_kv_snapshot_read<DBH>(
   #[smi] rid: ResourceId,
   #[serde] ranges: Vec<SnapshotReadRange>,
   #[serde] consistency: V8Consistency,
-) -> Result<Vec<Vec<ToV8KvEntry>>, AnyError>
+) -> Result<Vec<Vec<ToV8KvEntry>>, KvError>
 where
   DBH: DatabaseHandler + 'static,
 {
   let db = {
     let state = state.borrow();
-    let resource =
-      state.resource_table.get::<DatabaseResource<DBH::DB>>(rid)?;
+    let resource = state
+      .resource_table
+      .get::<DatabaseResource<DBH::DB>>(rid)
+      .map_err(KvError::Resource)?;
     resource.db.clone()
   };
 
@@ -278,10 +339,7 @@ where
   };
 
   if ranges.len() > config.max_read_ranges {
-    return Err(type_error(format!(
-      "Too many ranges (max {})",
-      config.max_read_ranges
-    )));
+    return Err(KvError::TooManyRanges(config.max_read_ranges));
   }
 
   let mut total_entries = 0usize;
@@ -300,33 +358,32 @@ where
       Ok(ReadRange {
         start,
         end,
-        limit: NonZeroU32::new(limit)
-          .with_context(|| "limit must be greater than 0")?,
+        limit: NonZeroU32::new(limit).ok_or(KvError::InvalidLimit)?,
         reverse,
       })
     })
-    .collect::<Result<Vec<_>, AnyError>>()?;
+    .collect::<Result<Vec<_>, KvError>>()?;
 
   if total_entries > config.max_read_entries {
-    return Err(type_error(format!(
-      "Too many entries (max {})",
-      config.max_read_entries
-    )));
+    return Err(KvError::TooManyEntries(config.max_read_entries));
   }
 
   let opts = SnapshotReadOptions {
     consistency: consistency.into(),
   };
-  let output_ranges = db.snapshot_read(read_ranges, opts).await?;
+  let output_ranges = db
+    .snapshot_read(read_ranges, opts)
+    .await
+    .map_err(KvError::Kv)?;
   let output_ranges = output_ranges
     .into_iter()
     .map(|x| {
       x.entries
         .into_iter()
         .map(TryInto::try_into)
-        .collect::<Result<Vec<_>, AnyError>>()
+        .collect::<Result<Vec<_>, std::io::Error>>()
     })
-    .collect::<Result<Vec<_>, AnyError>>()?;
+    .collect::<Result<Vec<_>, std::io::Error>>()?;
   Ok(output_ranges)
 }
 
@@ -345,7 +402,7 @@ impl<QMH: QueueMessageHandle + 'static> Resource for QueueMessageResource<QMH> {
 async fn op_kv_dequeue_next_message<DBH>(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<Option<(ToJsBuffer, ResourceId)>, AnyError>
+) -> Result<Option<(ToJsBuffer, ResourceId)>, KvError>
 where
   DBH: DatabaseHandler + 'static,
 {
@@ -358,17 +415,19 @@ where
           if get_custom_error_class(&err) == Some("BadResource") {
             return Ok(None);
           } else {
-            return Err(err);
+            return Err(KvError::Resource(err));
           }
         }
       };
     resource.db.clone()
   };
 
-  let Some(mut handle) = db.dequeue_next_message().await? else {
+  let Some(mut handle) =
+    db.dequeue_next_message().await.map_err(KvError::Kv)?
+  else {
     return Ok(None);
   };
-  let payload = handle.take_payload().await?.into();
+  let payload = handle.take_payload().await.map_err(KvError::Kv)?.into();
   let handle_rid = {
     let mut state = state.borrow_mut();
     state.resource_table.add(QueueMessageResource { handle })
@@ -382,18 +441,18 @@ fn op_kv_watch<DBH>(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   #[serde] keys: Vec<KvKey>,
-) -> Result<ResourceId, AnyError>
+) -> Result<ResourceId, KvError>
 where
   DBH: DatabaseHandler + 'static,
 {
-  let resource = state.resource_table.get::<DatabaseResource<DBH::DB>>(rid)?;
+  let resource = state
+    .resource_table
+    .get::<DatabaseResource<DBH::DB>>(rid)
+    .map_err(KvError::Resource)?;
   let config = state.borrow::<Rc<KvConfig>>().clone();
 
   if keys.len() > config.max_watched_keys {
-    return Err(type_error(format!(
-      "Too many keys (max {})",
-      config.max_watched_keys
-    )));
+    return Err(KvError::TooManyKeys(config.max_watched_keys));
   }
 
   let keys: Vec<Vec<u8>> = keys
@@ -428,10 +487,13 @@ enum WatchEntry {
 async fn op_kv_watch_next(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<Option<Vec<WatchEntry>>, AnyError> {
+) -> Result<Option<Vec<WatchEntry>>, KvError> {
   let resource = {
     let state = state.borrow();
-    let resource = state.resource_table.get::<DatabaseWatcherResource>(rid)?;
+    let resource = state
+      .resource_table
+      .get::<DatabaseWatcherResource>(rid)
+      .map_err(KvError::Resource)?;
     resource.clone()
   };
 
@@ -457,7 +519,7 @@ async fn op_kv_watch_next(
     return Ok(None);
   };
 
-  let entries = res?;
+  let entries = res.map_err(KvError::Kv)?;
   let entries = entries
     .into_iter()
     .map(|entry| {
@@ -468,7 +530,7 @@ async fn op_kv_watch_next(
         WatchKeyOutput::Unchanged => WatchEntry::Unchanged,
       })
     })
-    .collect::<Result<_, anyhow::Error>>()?;
+    .collect::<Result<_, KvError>>()?;
 
   Ok(Some(entries))
 }
@@ -478,7 +540,7 @@ async fn op_kv_finish_dequeued_message<DBH>(
   state: Rc<RefCell<OpState>>,
   #[smi] handle_rid: ResourceId,
   success: bool,
-) -> Result<(), AnyError>
+) -> Result<(), KvError>
 where
   DBH: DatabaseHandler + 'static,
 {
@@ -487,9 +549,9 @@ where
     let handle = state
       .resource_table
       .take::<QueueMessageResource<<<DBH>::DB as Database>::QMH>>(handle_rid)
-      .map_err(|_| type_error("Queue message not found"))?;
+      .map_err(|_| KvError::QueueMessageNotFound)?;
     Rc::try_unwrap(handle)
-      .map_err(|_| type_error("Queue message not found"))?
+      .map_err(|_| KvError::QueueMessageNotFound)?
       .handle
   };
   // if we fail to finish the message, there is not much we can do and the
@@ -500,32 +562,52 @@ where
   Ok(())
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum KvCheckError {
+  #[error("invalid versionstamp")]
+  InvalidVersionstamp,
+  #[error(transparent)]
+  Io(std::io::Error),
+}
+
 type V8KvCheck = (KvKey, Option<ByteString>);
 
-fn check_from_v8(value: V8KvCheck) -> Result<Check, AnyError> {
+fn check_from_v8(value: V8KvCheck) -> Result<Check, KvCheckError> {
   let versionstamp = match value.1 {
     Some(data) => {
       let mut out = [0u8; 10];
       if data.len() != out.len() * 2 {
-        bail!(type_error("invalid versionstamp"));
+        return Err(KvCheckError::InvalidVersionstamp);
       }
       faster_hex::hex_decode(&data, &mut out)
-        .map_err(|_| type_error("invalid versionstamp"))?;
+        .map_err(|_| KvCheckError::InvalidVersionstamp)?;
       Some(out)
     }
     None => None,
   };
   Ok(Check {
-    key: encode_v8_key(value.0)?,
+    key: encode_v8_key(value.0).map_err(KvCheckError::Io)?,
     versionstamp,
   })
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum KvMutationError {
+  #[error(transparent)]
+  BigInt(#[from] num_bigint::TryFromBigIntError<num_bigint::BigInt>),
+  #[error(transparent)]
+  Io(#[from] std::io::Error),
+  #[error("Invalid mutation '{0}' with value")]
+  InvalidMutationWithValue(String),
+  #[error("Invalid mutation '{0}' without value")]
+  InvalidMutationWithoutValue(String),
+}
+
 type V8KvMutation = (KvKey, String, Option<FromV8Value>, Option<u64>);
 
 fn mutation_from_v8(
   (value, current_timstamp): (V8KvMutation, DateTime<Utc>),
-) -> Result<Mutation, AnyError> {
+) -> Result<Mutation, KvMutationError> {
   let key = encode_v8_key(value.0)?;
   let kind = match (value.1.as_str(), value.2) {
     ("set", Some(value)) => MutationKind::Set(value.try_into()?),
@@ -542,10 +624,10 @@ fn mutation_from_v8(
       MutationKind::SetSuffixVersionstampedKey(value.try_into()?)
     }
     (op, Some(_)) => {
-      return Err(type_error(format!("Invalid mutation '{op}' with value")))
+      return Err(KvMutationError::InvalidMutationWithValue(op.to_string()))
     }
     (op, None) => {
-      return Err(type_error(format!("Invalid mutation '{op}' without value")))
+      return Err(KvMutationError::InvalidMutationWithoutValue(op.to_string()))
     }
   };
   Ok(Mutation {
@@ -562,7 +644,7 @@ type V8Enqueue = (JsBuffer, u64, Vec<KvKey>, Option<Vec<u32>>);
 fn enqueue_from_v8(
   value: V8Enqueue,
   current_timestamp: DateTime<Utc>,
-) -> Result<Enqueue, AnyError> {
+) -> Result<Enqueue, std::io::Error> {
   Ok(Enqueue {
     payload: value.0.to_vec(),
     deadline: current_timestamp
@@ -597,7 +679,7 @@ impl RawSelector {
     prefix: Option<KvKey>,
     start: Option<KvKey>,
     end: Option<KvKey>,
-  ) -> Result<Self, AnyError> {
+  ) -> Result<Self, KvError> {
     let prefix = prefix.map(encode_v8_key).transpose()?;
     let start = start.map(encode_v8_key).transpose()?;
     let end = end.map(encode_v8_key).transpose()?;
@@ -610,9 +692,7 @@ impl RawSelector {
       }),
       (Some(prefix), Some(start), None) => {
         if !start.starts_with(&prefix) || start.len() == prefix.len() {
-          return Err(type_error(
-            "Start key is not in the keyspace defined by prefix",
-          ));
+          return Err(KvError::StartKeyNotInKeyspace);
         }
         Ok(Self::Prefixed {
           prefix,
@@ -622,9 +702,7 @@ impl RawSelector {
       }
       (Some(prefix), None, Some(end)) => {
         if !end.starts_with(&prefix) || end.len() == prefix.len() {
-          return Err(type_error(
-            "End key is not in the keyspace defined by prefix",
-          ));
+          return Err(KvError::EndKeyNotInKeyspace);
         }
         Ok(Self::Prefixed {
           prefix,
@@ -634,7 +712,7 @@ impl RawSelector {
       }
       (None, Some(start), Some(end)) => {
         if start > end {
-          return Err(type_error("Start key is greater than end key"));
+          return Err(KvError::StartKeyGreaterThanEndKey);
         }
         Ok(Self::Range { start, end })
       }
@@ -642,7 +720,7 @@ impl RawSelector {
         let end = start.iter().copied().chain(Some(0)).collect();
         Ok(Self::Range { start, end })
       }
-      _ => Err(type_error("Invalid range")),
+      _ => Err(KvError::InvalidRange),
     }
   }
 
@@ -701,10 +779,10 @@ fn common_prefix_for_bytes<'a>(a: &'a [u8], b: &'a [u8]) -> &'a [u8] {
 fn encode_cursor(
   selector: &RawSelector,
   boundary_key: &[u8],
-) -> Result<String, AnyError> {
+) -> Result<String, KvError> {
   let common_prefix = selector.common_prefix();
   if !boundary_key.starts_with(common_prefix) {
-    return Err(type_error("Invalid boundary key"));
+    return Err(KvError::InvalidBoundaryKey);
   }
   Ok(BASE64_URL_SAFE.encode(&boundary_key[common_prefix.len()..]))
 }
@@ -713,7 +791,7 @@ fn decode_selector_and_cursor(
   selector: &RawSelector,
   reverse: bool,
   cursor: Option<&ByteString>,
-) -> Result<(Vec<u8>, Vec<u8>), AnyError> {
+) -> Result<(Vec<u8>, Vec<u8>), KvError> {
   let Some(cursor) = cursor else {
     return Ok((selector.range_start_key(), selector.range_end_key()));
   };
@@ -721,7 +799,7 @@ fn decode_selector_and_cursor(
   let common_prefix = selector.common_prefix();
   let cursor = BASE64_URL_SAFE
     .decode(cursor)
-    .map_err(|_| type_error("invalid cursor"))?;
+    .map_err(|_| KvError::InvalidCursor)?;
 
   let first_key: Vec<u8>;
   let last_key: Vec<u8>;
@@ -746,13 +824,13 @@ fn decode_selector_and_cursor(
   // Defend against out-of-bounds reading
   if let Some(start) = selector.start() {
     if &first_key[..] < start {
-      return Err(type_error("cursor out of bounds"));
+      return Err(KvError::CursorOutOfBounds);
     }
   }
 
   if let Some(end) = selector.end() {
     if &last_key[..] > end {
-      return Err(type_error("cursor out of bounds"));
+      return Err(KvError::CursorOutOfBounds);
     }
   }
 
@@ -767,15 +845,17 @@ async fn op_kv_atomic_write<DBH>(
   #[serde] checks: Vec<V8KvCheck>,
   #[serde] mutations: Vec<V8KvMutation>,
   #[serde] enqueues: Vec<V8Enqueue>,
-) -> Result<Option<String>, AnyError>
+) -> Result<Option<String>, KvError>
 where
   DBH: DatabaseHandler + 'static,
 {
   let current_timestamp = chrono::Utc::now();
   let db = {
     let state = state.borrow();
-    let resource =
-      state.resource_table.get::<DatabaseResource<DBH::DB>>(rid)?;
+    let resource = state
+      .resource_table
+      .get::<DatabaseResource<DBH::DB>>(rid)
+      .map_err(KvError::Resource)?;
     resource.db.clone()
   };
 
@@ -785,34 +865,28 @@ where
   };
 
   if checks.len() > config.max_checks {
-    return Err(type_error(format!(
-      "Too many checks (max {})",
-      config.max_checks
-    )));
+    return Err(KvError::TooManyChecks(config.max_checks));
   }
 
   if mutations.len() + enqueues.len() > config.max_mutations {
-    return Err(type_error(format!(
-      "Too many mutations (max {})",
-      config.max_mutations
-    )));
+    return Err(KvError::TooManyMutations(config.max_mutations));
   }
 
   let checks = checks
     .into_iter()
     .map(check_from_v8)
-    .collect::<Result<Vec<Check>, AnyError>>()
-    .with_context(|| "invalid check")?;
+    .collect::<Result<Vec<Check>, KvCheckError>>()
+    .map_err(KvError::InvalidCheck)?;
   let mutations = mutations
     .into_iter()
     .map(|mutation| mutation_from_v8((mutation, current_timestamp)))
-    .collect::<Result<Vec<Mutation>, AnyError>>()
-    .with_context(|| "Invalid mutation")?;
+    .collect::<Result<Vec<Mutation>, KvMutationError>>()
+    .map_err(KvError::InvalidMutation)?;
   let enqueues = enqueues
     .into_iter()
     .map(|e| enqueue_from_v8(e, current_timestamp))
-    .collect::<Result<Vec<Enqueue>, AnyError>>()
-    .with_context(|| "invalid enqueue")?;
+    .collect::<Result<Vec<Enqueue>, std::io::Error>>()
+    .map_err(KvError::InvalidEnqueue)?;
 
   let mut total_payload_size = 0usize;
   let mut total_key_size = 0usize;
@@ -823,7 +897,7 @@ where
     .chain(mutations.iter().map(|m| &m.key))
   {
     if key.is_empty() {
-      return Err(type_error("key cannot be empty"));
+      return Err(KvError::EmptyKey);
     }
 
     total_payload_size += check_write_key_size(key, &config)?;
@@ -847,17 +921,13 @@ where
   }
 
   if total_payload_size > config.max_total_mutation_size_bytes {
-    return Err(type_error(format!(
-      "Total mutation size too large (max {} bytes)",
-      config.max_total_mutation_size_bytes
-    )));
+    return Err(KvError::TotalMutationTooLarge(
+      config.max_total_mutation_size_bytes,
+    ));
   }
 
   if total_key_size > config.max_total_key_size_bytes {
-    return Err(type_error(format!(
-      "Total key size too large (max {} bytes)",
-      config.max_total_key_size_bytes
-    )));
+    return Err(KvError::TotalKeyTooLarge(config.max_total_key_size_bytes));
   }
 
   let atomic_write = AtomicWrite {
@@ -866,7 +936,7 @@ where
     enqueues,
   };
 
-  let result = db.atomic_write(atomic_write).await?;
+  let result = db.atomic_write(atomic_write).await.map_err(KvError::Kv)?;
 
   Ok(result.map(|res| faster_hex::hex_string(&res.versionstamp)))
 }
@@ -879,19 +949,16 @@ type EncodeCursorRangeSelector = (Option<KvKey>, Option<KvKey>, Option<KvKey>);
 fn op_kv_encode_cursor(
   #[serde] (prefix, start, end): EncodeCursorRangeSelector,
   #[serde] boundary_key: KvKey,
-) -> Result<String, AnyError> {
+) -> Result<String, KvError> {
   let selector = RawSelector::from_tuple(prefix, start, end)?;
   let boundary_key = encode_v8_key(boundary_key)?;
   let cursor = encode_cursor(&selector, &boundary_key)?;
   Ok(cursor)
 }
 
-fn check_read_key_size(key: &[u8], config: &KvConfig) -> Result<(), AnyError> {
+fn check_read_key_size(key: &[u8], config: &KvConfig) -> Result<(), KvError> {
   if key.len() > config.max_read_key_size_bytes {
-    Err(type_error(format!(
-      "Key too large for read (max {} bytes)",
-      config.max_read_key_size_bytes
-    )))
+    Err(KvError::KeyTooLargeToRead(config.max_read_key_size_bytes))
   } else {
     Ok(())
   }
@@ -900,12 +967,9 @@ fn check_read_key_size(key: &[u8], config: &KvConfig) -> Result<(), AnyError> {
 fn check_write_key_size(
   key: &[u8],
   config: &KvConfig,
-) -> Result<usize, AnyError> {
+) -> Result<usize, KvError> {
   if key.len() > config.max_write_key_size_bytes {
-    Err(type_error(format!(
-      "Key too large for write (max {} bytes)",
-      config.max_write_key_size_bytes
-    )))
+    Err(KvError::KeyTooLargeToWrite(config.max_write_key_size_bytes))
   } else {
     Ok(key.len())
   }
@@ -914,7 +978,7 @@ fn check_write_key_size(
 fn check_value_size(
   value: &KvValue,
   config: &KvConfig,
-) -> Result<usize, AnyError> {
+) -> Result<usize, KvError> {
   let payload = match value {
     KvValue::Bytes(x) => x,
     KvValue::V8(x) => x,
@@ -922,10 +986,7 @@ fn check_value_size(
   };
 
   if payload.len() > config.max_value_size_bytes {
-    Err(type_error(format!(
-      "Value too large (max {} bytes)",
-      config.max_value_size_bytes
-    )))
+    Err(KvError::ValueTooLarge(config.max_value_size_bytes))
   } else {
     Ok(payload.len())
   }
@@ -934,12 +995,9 @@ fn check_value_size(
 fn check_enqueue_payload_size(
   payload: &[u8],
   config: &KvConfig,
-) -> Result<usize, AnyError> {
+) -> Result<usize, KvError> {
   if payload.len() > config.max_value_size_bytes {
-    Err(type_error(format!(
-      "enqueue payload too large (max {} bytes)",
-      config.max_value_size_bytes
-    )))
+    Err(KvError::EnqueuePayloadTooLarge(config.max_value_size_bytes))
   } else {
     Ok(payload.len())
   }
diff --git a/ext/kv/remote.rs b/ext/kv/remote.rs
index 922853588a..4930aacfe3 100644
--- a/ext/kv/remote.rs
+++ b/ext/kv/remote.rs
@@ -15,6 +15,7 @@ use deno_core::futures::Stream;
 use deno_core::OpState;
 use deno_fetch::create_http_client;
 use deno_fetch::CreateHttpClientOptions;
+use deno_permissions::PermissionCheckError;
 use deno_tls::rustls::RootCertStore;
 use deno_tls::Proxy;
 use deno_tls::RootCertStoreProvider;
@@ -45,17 +46,17 @@ impl HttpOptions {
 }
 
 pub trait RemoteDbHandlerPermissions {
-  fn check_env(&mut self, var: &str) -> Result<(), AnyError>;
+  fn check_env(&mut self, var: &str) -> Result<(), PermissionCheckError>;
   fn check_net_url(
     &mut self,
     url: &Url,
     api_name: &str,
-  ) -> Result<(), AnyError>;
+  ) -> Result<(), PermissionCheckError>;
 }
 
 impl RemoteDbHandlerPermissions for deno_permissions::PermissionsContainer {
   #[inline(always)]
-  fn check_env(&mut self, var: &str) -> Result<(), AnyError> {
+  fn check_env(&mut self, var: &str) -> Result<(), PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_env(self, var)
   }
 
@@ -64,7 +65,7 @@ impl RemoteDbHandlerPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     url: &Url,
     api_name: &str,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_net_url(self, url, api_name)
   }
 }
@@ -103,7 +104,9 @@ impl<P: RemoteDbHandlerPermissions + 'static> denokv_remote::RemotePermissions
   fn check_net_url(&self, url: &Url) -> Result<(), anyhow::Error> {
     let mut state = self.state.borrow_mut();
     let permissions = state.borrow_mut::<P>();
-    permissions.check_net_url(url, "Deno.openKv")
+    permissions
+      .check_net_url(url, "Deno.openKv")
+      .map_err(Into::into)
   }
 }
 
diff --git a/ext/kv/sqlite.rs b/ext/kv/sqlite.rs
index 8027ff03d4..9de5209275 100644
--- a/ext/kv/sqlite.rs
+++ b/ext/kv/sqlite.rs
@@ -13,20 +13,20 @@ use std::sync::Arc;
 use std::sync::Mutex;
 use std::sync::OnceLock;
 
+use crate::DatabaseHandler;
 use async_trait::async_trait;
 use deno_core::error::type_error;
 use deno_core::error::AnyError;
-use deno_core::normalize_path;
 use deno_core::unsync::spawn_blocking;
 use deno_core::OpState;
+use deno_path_util::normalize_path;
+use deno_permissions::PermissionCheckError;
 pub use denokv_sqlite::SqliteBackendError;
 use denokv_sqlite::SqliteConfig;
 use denokv_sqlite::SqliteNotifier;
 use rand::SeedableRng;
 use rusqlite::OpenFlags;
 
-use crate::DatabaseHandler;
-
 static SQLITE_NOTIFIERS_MAP: OnceLock<Mutex<HashMap<PathBuf, SqliteNotifier>>> =
   OnceLock::new();
 
@@ -42,13 +42,13 @@ pub trait SqliteDbHandlerPermissions {
     &mut self,
     p: &str,
     api_name: &str,
-  ) -> Result<PathBuf, AnyError>;
+  ) -> Result<PathBuf, PermissionCheckError>;
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
   fn check_write<'a>(
     &mut self,
     p: &'a Path,
     api_name: &str,
-  ) -> Result<Cow<'a, Path>, AnyError>;
+  ) -> Result<Cow<'a, Path>, PermissionCheckError>;
 }
 
 impl SqliteDbHandlerPermissions for deno_permissions::PermissionsContainer {
@@ -57,7 +57,7 @@ impl SqliteDbHandlerPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     p: &str,
     api_name: &str,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_read(self, p, api_name)
   }
 
@@ -66,7 +66,7 @@ impl SqliteDbHandlerPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     p: &'a Path,
     api_name: &str,
-  ) -> Result<Cow<'a, Path>, AnyError> {
+  ) -> Result<Cow<'a, Path>, PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_write_path(self, p, api_name)
   }
 }
diff --git a/ext/napi/Cargo.toml b/ext/napi/Cargo.toml
index aabf6d31f5..df3ec0287b 100644
--- a/ext/napi/Cargo.toml
+++ b/ext/napi/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_napi"
-version = "0.99.0"
+version = "0.108.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -16,4 +16,14 @@ path = "lib.rs"
 [dependencies]
 deno_core.workspace = true
 deno_permissions.workspace = true
+libc.workspace = true
 libloading = { version = "0.7" }
+log.workspace = true
+napi_sym.workspace = true
+thiserror.workspace = true
+
+[target.'cfg(windows)'.dependencies]
+windows-sys.workspace = true
+
+[dev-dependencies]
+libuv-sys-lite = "=1.48.2"
diff --git a/ext/napi/README.md b/ext/napi/README.md
index e69de29bb2..b479295244 100644
--- a/ext/napi/README.md
+++ b/ext/napi/README.md
@@ -0,0 +1,114 @@
+# napi
+
+This directory contains source for Deno's Node-API implementation. It depends on
+`napi_sym` and `deno_napi`.
+
+Files are generally organized the same as in Node.js's implementation to ease in
+ensuring compatibility.
+
+## Adding a new function
+
+Add the symbol name to
+[`cli/napi_sym/symbol_exports.json`](../napi_sym/symbol_exports.json).
+
+```diff
+{
+  "symbols": [
+    ...
+    "napi_get_undefined",
+-   "napi_get_null"
++   "napi_get_null",
++   "napi_get_boolean"
+  ]
+}
+```
+
+Determine where to place the implementation. `napi_get_boolean` is related to JS
+values so we will place it in `js_native_api.rs`. If something is not clear,
+just create a new file module.
+
+See [`napi_sym`](../napi_sym/) for writing the implementation:
+
+```rust
+#[napi_sym::napi_sym]
+fn napi_get_boolean(
+  env: *mut Env,
+  value: bool,
+  result: *mut napi_value,
+) -> Result {
+  // ...
+  Ok(())
+}
+```
+
+Update the generated symbol lists using the script:
+
+```
+deno run --allow-write tools/napi/generate_symbols_lists.js
+```
+
+Add a test in [`/tests/napi`](../../tests/napi/). You can also refer to Node.js
+test suite for Node-API.
+
+```js
+// tests/napi/boolean_test.js
+import { assertEquals, loadTestLibrary } from "./common.js";
+const lib = loadTestLibrary();
+Deno.test("napi get boolean", function () {
+  assertEquals(lib.test_get_boolean(true), true);
+  assertEquals(lib.test_get_boolean(false), false);
+});
+```
+
+```rust
+// tests/napi/src/boolean.rs
+
+use napi_sys::Status::napi_ok;
+use napi_sys::ValueType::napi_boolean;
+use napi_sys::*;
+
+extern "C" fn test_boolean(
+  env: napi_env,
+  info: napi_callback_info,
+) -> napi_value {
+  let (args, argc, _) = crate::get_callback_info!(env, info, 1);
+  assert_eq!(argc, 1);
+
+  let mut ty = -1;
+  assert!(unsafe { napi_typeof(env, args[0], &mut ty) } == napi_ok);
+  assert_eq!(ty, napi_boolean);
+
+  // Use napi_get_boolean here...
+
+  value
+}
+
+pub fn init(env: napi_env, exports: napi_value) {
+  let properties = &[crate::new_property!(env, "test_boolean\0", test_boolean)];
+
+  unsafe {
+    napi_define_properties(env, exports, properties.len(), properties.as_ptr())
+  };
+}
+```
+
+```diff
+// tests/napi/src/lib.rs
+
++ mod boolean;
+
+...
+
+#[no_mangle]
+unsafe extern "C" fn napi_register_module_v1(
+  env: napi_env,
+  exports: napi_value,
+) -> napi_value {
+  ...
++ boolean::init(env, exports);
+
+  exports
+}
+```
+
+Run the test using `cargo test -p tests/napi`.
diff --git a/ext/napi/build.rs b/ext/napi/build.rs
new file mode 100644
index 0000000000..8705830a95
--- /dev/null
+++ b/ext/napi/build.rs
@@ -0,0 +1,22 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+fn main() {
+  let symbols_file_name = match std::env::consts::OS {
+    "android" | "freebsd" | "openbsd" => {
+      "generated_symbol_exports_list_linux.def".to_string()
+    }
+    os => format!("generated_symbol_exports_list_{}.def", os),
+  };
+  let symbols_path = std::path::Path::new(".")
+    .join(symbols_file_name)
+    .canonicalize()
+    .expect(
+        "Missing symbols list! Generate using tools/napi/generate_symbols_lists.js",
+    );
+
+  println!("cargo:rustc-rerun-if-changed={}", symbols_path.display());
+
+  let path = std::path::PathBuf::from(std::env::var("OUT_DIR").unwrap())
+    .join("napi_symbol_path.txt");
+  std::fs::write(path, symbols_path.as_os_str().as_encoded_bytes()).unwrap();
+}
diff --git a/cli/napi/generated_symbol_exports_list_linux.def b/ext/napi/generated_symbol_exports_list_linux.def
similarity index 96%
rename from cli/napi/generated_symbol_exports_list_linux.def
rename to ext/napi/generated_symbol_exports_list_linux.def
index 06e94f05bb..614880ebfa 100644
--- a/cli/napi/generated_symbol_exports_list_linux.def
+++ b/ext/napi/generated_symbol_exports_list_linux.def
@@ -1 +1 @@
-{ "node_api_create_syntax_error"; "napi_make_callback"; "napi_has_named_property"; "napi_async_destroy"; "napi_coerce_to_object"; "napi_get_arraybuffer_info"; "napi_detach_arraybuffer"; "napi_get_undefined"; "napi_reference_unref"; "napi_fatal_error"; "napi_open_callback_scope"; "napi_close_callback_scope"; "napi_get_value_uint32"; "napi_create_function"; "napi_create_arraybuffer"; "napi_get_value_int64"; "napi_get_all_property_names"; "napi_resolve_deferred"; "napi_is_detached_arraybuffer"; "napi_create_string_utf8"; "napi_create_threadsafe_function"; "node_api_throw_syntax_error"; "napi_create_bigint_int64"; "napi_wrap"; "napi_set_property"; "napi_get_value_bigint_int64"; "napi_open_handle_scope"; "napi_create_error"; "napi_create_buffer"; "napi_cancel_async_work"; "napi_is_exception_pending"; "napi_acquire_threadsafe_function"; "napi_create_external"; "napi_get_threadsafe_function_context"; "napi_get_null"; "napi_create_string_utf16"; "node_api_create_external_string_utf16"; "napi_get_value_bigint_uint64"; "napi_module_register"; "napi_is_typedarray"; "napi_create_external_buffer"; "napi_get_new_target"; "napi_get_instance_data"; "napi_close_handle_scope"; "napi_get_value_string_utf16"; "napi_get_property_names"; "napi_is_arraybuffer"; "napi_get_cb_info"; "napi_define_properties"; "napi_add_env_cleanup_hook"; "node_api_get_module_file_name"; "napi_get_node_version"; "napi_create_int64"; "napi_create_double"; "napi_get_and_clear_last_exception"; "napi_create_reference"; "napi_get_typedarray_info"; "napi_call_threadsafe_function"; "napi_get_last_error_info"; "napi_create_array_with_length"; "napi_coerce_to_number"; "napi_get_global"; "napi_is_error"; "napi_set_instance_data"; "napi_create_typedarray"; "napi_throw_type_error"; "napi_has_property"; "napi_get_value_external"; "napi_create_range_error"; "napi_typeof"; "napi_ref_threadsafe_function"; "napi_create_bigint_uint64"; "napi_get_prototype"; "napi_adjust_external_memory"; "napi_release_threadsafe_function"; "napi_delete_async_work"; "napi_create_string_latin1"; "node_api_create_external_string_latin1"; "napi_is_array"; "napi_unref_threadsafe_function"; "napi_throw_error"; "napi_has_own_property"; "napi_get_reference_value"; "napi_remove_env_cleanup_hook"; "napi_get_value_string_utf8"; "napi_is_promise"; "napi_get_boolean"; "napi_run_script"; "napi_get_element"; "napi_get_named_property"; "napi_get_buffer_info"; "napi_get_value_bool"; "napi_reference_ref"; "napi_create_object"; "napi_create_promise"; "napi_create_int32"; "napi_escape_handle"; "napi_open_escapable_handle_scope"; "napi_throw"; "napi_get_value_double"; "napi_set_named_property"; "napi_call_function"; "napi_create_date"; "napi_object_freeze"; "napi_get_uv_event_loop"; "napi_get_value_string_latin1"; "napi_reject_deferred"; "napi_add_finalizer"; "napi_create_array"; "napi_delete_reference"; "napi_get_date_value"; "napi_create_dataview"; "napi_get_version"; "napi_define_class"; "napi_is_date"; "napi_remove_wrap"; "napi_delete_property"; "napi_instanceof"; "napi_create_buffer_copy"; "napi_delete_element"; "napi_object_seal"; "napi_queue_async_work"; "napi_get_value_bigint_words"; "napi_is_buffer"; "napi_get_array_length"; "napi_get_property"; "napi_new_instance"; "napi_set_element"; "napi_create_bigint_words"; "napi_strict_equals"; "napi_is_dataview"; "napi_close_escapable_handle_scope"; "napi_get_dataview_info"; "napi_get_value_int32"; "napi_unwrap"; "napi_throw_range_error"; "napi_coerce_to_bool"; "napi_create_uint32"; "napi_has_element"; "napi_create_external_arraybuffer"; "napi_create_symbol"; "node_api_symbol_for"; "napi_coerce_to_string"; "napi_create_type_error"; "napi_fatal_exception"; "napi_create_async_work"; "napi_async_init"; "node_api_create_property_key_utf16"; "napi_type_tag_object"; "napi_check_object_type_tag"; "node_api_post_finalizer"; "napi_add_async_cleanup_hook"; "napi_remove_async_cleanup_hook"; };
\ No newline at end of file
+{ "node_api_create_syntax_error"; "napi_make_callback"; "napi_has_named_property"; "napi_async_destroy"; "napi_coerce_to_object"; "napi_get_arraybuffer_info"; "napi_detach_arraybuffer"; "napi_get_undefined"; "napi_reference_unref"; "napi_fatal_error"; "napi_open_callback_scope"; "napi_close_callback_scope"; "napi_get_value_uint32"; "napi_create_function"; "napi_create_arraybuffer"; "napi_get_value_int64"; "napi_get_all_property_names"; "napi_resolve_deferred"; "napi_is_detached_arraybuffer"; "napi_create_string_utf8"; "napi_create_threadsafe_function"; "node_api_throw_syntax_error"; "napi_create_bigint_int64"; "napi_wrap"; "napi_set_property"; "napi_get_value_bigint_int64"; "napi_open_handle_scope"; "napi_create_error"; "napi_create_buffer"; "napi_cancel_async_work"; "napi_is_exception_pending"; "napi_acquire_threadsafe_function"; "napi_create_external"; "napi_get_threadsafe_function_context"; "napi_get_null"; "napi_create_string_utf16"; "node_api_create_external_string_utf16"; "napi_get_value_bigint_uint64"; "napi_module_register"; "napi_is_typedarray"; "napi_create_external_buffer"; "napi_get_new_target"; "napi_get_instance_data"; "napi_close_handle_scope"; "napi_get_value_string_utf16"; "napi_get_property_names"; "napi_is_arraybuffer"; "napi_get_cb_info"; "napi_define_properties"; "napi_add_env_cleanup_hook"; "node_api_get_module_file_name"; "napi_get_node_version"; "napi_create_int64"; "napi_create_double"; "napi_get_and_clear_last_exception"; "napi_create_reference"; "napi_get_typedarray_info"; "napi_call_threadsafe_function"; "napi_get_last_error_info"; "napi_create_array_with_length"; "napi_coerce_to_number"; "napi_get_global"; "napi_is_error"; "napi_set_instance_data"; "napi_create_typedarray"; "napi_throw_type_error"; "napi_has_property"; "napi_get_value_external"; "napi_create_range_error"; "napi_typeof"; "napi_ref_threadsafe_function"; "napi_create_bigint_uint64"; "napi_get_prototype"; "napi_adjust_external_memory"; "napi_release_threadsafe_function"; "napi_delete_async_work"; "napi_create_string_latin1"; "node_api_create_external_string_latin1"; "napi_is_array"; "napi_unref_threadsafe_function"; "napi_throw_error"; "napi_has_own_property"; "napi_get_reference_value"; "napi_remove_env_cleanup_hook"; "napi_get_value_string_utf8"; "napi_is_promise"; "napi_get_boolean"; "napi_run_script"; "napi_get_element"; "napi_get_named_property"; "napi_get_buffer_info"; "napi_get_value_bool"; "napi_reference_ref"; "napi_create_object"; "napi_create_promise"; "napi_create_int32"; "napi_escape_handle"; "napi_open_escapable_handle_scope"; "napi_throw"; "napi_get_value_double"; "napi_set_named_property"; "napi_call_function"; "napi_create_date"; "napi_object_freeze"; "napi_get_uv_event_loop"; "napi_get_value_string_latin1"; "napi_reject_deferred"; "napi_add_finalizer"; "napi_create_array"; "napi_delete_reference"; "napi_get_date_value"; "napi_create_dataview"; "napi_get_version"; "napi_define_class"; "napi_is_date"; "napi_remove_wrap"; "napi_delete_property"; "napi_instanceof"; "napi_create_buffer_copy"; "napi_delete_element"; "napi_object_seal"; "napi_queue_async_work"; "napi_get_value_bigint_words"; "napi_is_buffer"; "napi_get_array_length"; "napi_get_property"; "napi_new_instance"; "napi_set_element"; "napi_create_bigint_words"; "napi_strict_equals"; "napi_is_dataview"; "napi_close_escapable_handle_scope"; "napi_get_dataview_info"; "napi_get_value_int32"; "napi_unwrap"; "napi_throw_range_error"; "napi_coerce_to_bool"; "napi_create_uint32"; "napi_has_element"; "napi_create_external_arraybuffer"; "napi_create_symbol"; "node_api_symbol_for"; "napi_coerce_to_string"; "napi_create_type_error"; "napi_fatal_exception"; "napi_create_async_work"; "napi_async_init"; "node_api_create_property_key_utf16"; "napi_type_tag_object"; "napi_check_object_type_tag"; "node_api_post_finalizer"; "napi_add_async_cleanup_hook"; "napi_remove_async_cleanup_hook"; "uv_mutex_init"; "uv_mutex_lock"; "uv_mutex_unlock"; "uv_mutex_destroy"; "uv_async_init"; "uv_async_send"; "uv_close"; };
\ No newline at end of file
diff --git a/cli/napi/generated_symbol_exports_list_macos.def b/ext/napi/generated_symbol_exports_list_macos.def
similarity index 96%
rename from cli/napi/generated_symbol_exports_list_macos.def
rename to ext/napi/generated_symbol_exports_list_macos.def
index cac7100c6f..36b2f37fa5 100644
--- a/cli/napi/generated_symbol_exports_list_macos.def
+++ b/ext/napi/generated_symbol_exports_list_macos.def
@@ -150,4 +150,11 @@ _napi_type_tag_object
 _napi_check_object_type_tag
 _node_api_post_finalizer
 _napi_add_async_cleanup_hook
-_napi_remove_async_cleanup_hook
\ No newline at end of file
+_napi_remove_async_cleanup_hook
+_uv_mutex_init
+_uv_mutex_lock
+_uv_mutex_unlock
+_uv_mutex_destroy
+_uv_async_init
+_uv_async_send
+_uv_close
\ No newline at end of file
diff --git a/cli/napi/generated_symbol_exports_list_windows.def b/ext/napi/generated_symbol_exports_list_windows.def
similarity index 96%
rename from cli/napi/generated_symbol_exports_list_windows.def
rename to ext/napi/generated_symbol_exports_list_windows.def
index 5386b46e54..b7355112e7 100644
--- a/cli/napi/generated_symbol_exports_list_windows.def
+++ b/ext/napi/generated_symbol_exports_list_windows.def
@@ -152,4 +152,11 @@ EXPORTS
   napi_check_object_type_tag
   node_api_post_finalizer
   napi_add_async_cleanup_hook
-  napi_remove_async_cleanup_hook
\ No newline at end of file
+  napi_remove_async_cleanup_hook
+  uv_mutex_init
+  uv_mutex_lock
+  uv_mutex_unlock
+  uv_mutex_destroy
+  uv_async_init
+  uv_async_send
+  uv_close
\ No newline at end of file
diff --git a/cli/napi/js_native_api.rs b/ext/napi/js_native_api.rs
similarity index 98%
rename from cli/napi/js_native_api.rs
rename to ext/napi/js_native_api.rs
index e922d8c3f2..53a12d6eba 100644
--- a/cli/napi/js_native_api.rs
+++ b/ext/napi/js_native_api.rs
@@ -5,7 +5,7 @@
 
 const NAPI_VERSION: u32 = 9;
 
-use deno_runtime::deno_napi::*;
+use crate::*;
 use libc::INT_MAX;
 
 use super::util::check_new_from_utf8;
@@ -17,9 +17,9 @@ use super::util::napi_set_last_error;
 use super::util::v8_name_from_property_descriptor;
 use crate::check_arg;
 use crate::check_env;
-use deno_runtime::deno_napi::function::create_function;
-use deno_runtime::deno_napi::function::create_function_template;
-use deno_runtime::deno_napi::function::CallbackInfo;
+use crate::function::create_function;
+use crate::function::create_function_template;
+use crate::function::CallbackInfo;
 use napi_sym::napi_sym;
 use std::ptr::NonNull;
 
@@ -264,6 +264,16 @@ fn napi_define_class<'s>(
       Err(status) => return status,
     };
 
+    let mut accessor_property = v8::PropertyAttribute::NONE;
+
+    if p.attributes & napi_enumerable == 0 {
+      accessor_property = accessor_property | v8::PropertyAttribute::DONT_ENUM;
+    }
+    if p.attributes & napi_configurable == 0 {
+      accessor_property =
+        accessor_property | v8::PropertyAttribute::DONT_DELETE;
+    }
+
     if p.getter.is_some() || p.setter.is_some() {
       let getter = p.getter.map(|g| {
         create_function_template(&mut env.scope(), env_ptr, None, g, p.data)
@@ -271,8 +281,6 @@ fn napi_define_class<'s>(
       let setter = p.setter.map(|s| {
         create_function_template(&mut env.scope(), env_ptr, None, s, p.data)
       });
-
-      let mut accessor_property = v8::PropertyAttribute::NONE;
       if getter.is_some()
         && setter.is_some()
         && (p.attributes & napi_writable) == 0
@@ -280,15 +288,6 @@ fn napi_define_class<'s>(
         accessor_property =
           accessor_property | v8::PropertyAttribute::READ_ONLY;
       }
-      if p.attributes & napi_enumerable == 0 {
-        accessor_property =
-          accessor_property | v8::PropertyAttribute::DONT_ENUM;
-      }
-      if p.attributes & napi_configurable == 0 {
-        accessor_property =
-          accessor_property | v8::PropertyAttribute::DONT_DELETE;
-      }
-
       let proto = tpl.prototype_template(&mut env.scope());
       proto.set_accessor_property(name, getter, setter, accessor_property);
     } else if let Some(method) = p.method {
@@ -300,10 +299,14 @@ fn napi_define_class<'s>(
         p.data,
       );
       let proto = tpl.prototype_template(&mut env.scope());
-      proto.set(name, function.into());
+      proto.set_with_attr(name, function.into(), accessor_property);
     } else {
       let proto = tpl.prototype_template(&mut env.scope());
-      proto.set(name, p.value.unwrap().into());
+      if (p.attributes & napi_writable) == 0 {
+        accessor_property =
+          accessor_property | v8::PropertyAttribute::READ_ONLY;
+      }
+      proto.set_with_attr(name, p.value.unwrap().into(), accessor_property);
     }
   }
 
@@ -1080,7 +1083,7 @@ fn napi_create_string_latin1(
 }
 
 #[napi_sym]
-fn napi_create_string_utf8(
+pub(crate) fn napi_create_string_utf8(
   env_ptr: *mut Env,
   string: *const c_char,
   length: usize,
@@ -1644,7 +1647,7 @@ fn napi_get_cb_info(
     check_arg!(env, argc);
     let argc = unsafe { *argc as usize };
     for i in 0..argc {
-      let mut arg = args.get(i as _);
+      let arg = args.get(i as _);
       unsafe {
         *argv.add(i) = arg.into();
       }
@@ -1694,15 +1697,14 @@ fn napi_get_new_target(
 }
 
 #[napi_sym]
-fn napi_call_function(
-  env_ptr: *mut Env,
-  recv: napi_value,
-  func: napi_value,
+fn napi_call_function<'s>(
+  env: &'s mut Env,
+  recv: napi_value<'s>,
+  func: napi_value<'s>,
   argc: usize,
-  argv: *const napi_value,
-  result: *mut napi_value,
+  argv: *const napi_value<'s>,
+  result: *mut napi_value<'s>,
 ) -> napi_status {
-  let env = check_env!(env_ptr);
   check_arg!(env, recv);
   let args = if argc > 0 {
     check_arg!(env, argv);
@@ -1716,11 +1718,11 @@ fn napi_call_function(
   let Some(func) =
     func.and_then(|f| v8::Local::<v8::Function>::try_from(f).ok())
   else {
-    return napi_set_last_error(env, napi_function_expected);
+    return napi_function_expected;
   };
 
   let Some(v) = func.call(&mut env.scope(), recv.unwrap(), args) else {
-    return napi_set_last_error(env_ptr, napi_generic_failure);
+    return napi_generic_failure;
   };
 
   if !result.is_null() {
@@ -1729,7 +1731,7 @@ fn napi_call_function(
     }
   }
 
-  return napi_clear_last_error(env_ptr);
+  napi_ok
 }
 
 #[napi_sym]
diff --git a/ext/napi/lib.rs b/ext/napi/lib.rs
index 4500c66fd4..88b8c238df 100644
--- a/ext/napi/lib.rs
+++ b/ext/napi/lib.rs
@@ -5,9 +5,23 @@
 #![allow(clippy::undocumented_unsafe_blocks)]
 #![deny(clippy::missing_safety_doc)]
 
+//! Symbols to be exported are now defined in this JSON file.
+//! The `#[napi_sym]` macro checks for missing entries and panics.
+//!
+//! `./tools/napi/generate_symbols_list.js` is used to generate the LINK `cli/exports.def` on Windows,
+//! which is also checked into git.
+//!
+//! To add a new napi function:
+//! 1. Place `#[napi_sym]` on top of your implementation.
+//! 2. Add the function's identifier to this JSON list.
+//! 3. Finally, run `tools/napi/generate_symbols_list.js` to update `ext/napi/generated_symbol_exports_list_*.def`.
+
+pub mod js_native_api;
+pub mod node_api;
+pub mod util;
+pub mod uv;
+
 use core::ptr::NonNull;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::parking_lot::RwLock;
 use deno_core::url::Url;
@@ -20,6 +34,18 @@ use std::path::PathBuf;
 use std::rc::Rc;
 use std::thread_local;
 
+#[derive(Debug, thiserror::Error)]
+pub enum NApiError {
+  #[error("Invalid path")]
+  InvalidPath,
+  #[error(transparent)]
+  LibLoading(#[from] libloading::Error),
+  #[error("Unable to find register Node-API module at {}", .0.display())]
+  ModuleNotFound(PathBuf),
+  #[error(transparent)]
+  Permission(#[from] PermissionCheckError),
+}
+
 #[cfg(unix)]
 use libloading::os::unix::*;
 
@@ -29,6 +55,7 @@ use libloading::os::windows::*;
 // Expose common stuff for ease of use.
 // `use deno_napi::*`
 pub use deno_core::v8;
+use deno_permissions::PermissionCheckError;
 pub use std::ffi::CStr;
 pub use std::os::raw::c_char;
 pub use std::os::raw::c_void;
@@ -482,14 +509,14 @@ deno_core::extension!(deno_napi,
 
 pub trait NapiPermissions {
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
-  fn check(&mut self, path: &str) -> std::result::Result<PathBuf, AnyError>;
+  fn check(&mut self, path: &str) -> Result<PathBuf, PermissionCheckError>;
 }
 
 // NOTE(bartlomieju): for now, NAPI uses `--allow-ffi` flag, but that might
 // change in the future.
 impl NapiPermissions for deno_permissions::PermissionsContainer {
   #[inline(always)]
-  fn check(&mut self, path: &str) -> Result<PathBuf, AnyError> {
+  fn check(&mut self, path: &str) -> Result<PathBuf, PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_ffi(self, path)
   }
 }
@@ -512,7 +539,7 @@ fn op_napi_open<NP, 'scope>(
   global: v8::Local<'scope, v8::Object>,
   buffer_constructor: v8::Local<'scope, v8::Function>,
   report_error: v8::Local<'scope, v8::Function>,
-) -> std::result::Result<v8::Local<'scope, v8::Value>, AnyError>
+) -> Result<v8::Local<'scope, v8::Value>, NApiError>
 where
   NP: NapiPermissions + 'static,
 {
@@ -540,7 +567,7 @@ where
   let type_tag = v8::Global::new(scope, type_tag);
 
   let url_filename =
-    Url::from_file_path(&path).map_err(|_| type_error("Invalid path"))?;
+    Url::from_file_path(&path).map_err(|_| NApiError::InvalidPath)?;
   let env_shared =
     EnvShared::new(napi_wrap, type_tag, format!("{url_filename}\0"));
 
@@ -565,17 +592,11 @@ where
 
   // SAFETY: opening a DLL calls dlopen
   #[cfg(unix)]
-  let library = match unsafe { Library::open(Some(&path), flags) } {
-    Ok(lib) => lib,
-    Err(e) => return Err(type_error(e.to_string())),
-  };
+  let library = unsafe { Library::open(Some(&path), flags) }?;
 
   // SAFETY: opening a DLL calls dlopen
   #[cfg(not(unix))]
-  let library = match unsafe { Library::load_with_flags(&path, flags) } {
-    Ok(lib) => lib,
-    Err(e) => return Err(type_error(e.to_string())),
-  };
+  let library = unsafe { Library::load_with_flags(&path, flags) }?;
 
   let maybe_module = MODULE_TO_REGISTER.with(|cell| {
     let mut slot = cell.borrow_mut();
@@ -610,10 +631,7 @@ where
     // SAFETY: we are going blind, calling the register function on the other side.
     unsafe { init(env_ptr, exports.into()) }
   } else {
-    return Err(type_error(format!(
-      "Unable to find register Node-API module at {}",
-      path.display()
-    )));
+    return Err(NApiError::ModuleNotFound(path));
   };
 
   let exports = maybe_exports.unwrap_or(exports.into());
@@ -624,3 +642,34 @@ where
 
   Ok(exports)
 }
+
+#[allow(clippy::print_stdout)]
+pub fn print_linker_flags(name: &str) {
+  let symbols_path =
+    include_str!(concat!(env!("OUT_DIR"), "/napi_symbol_path.txt"));
+
+  #[cfg(target_os = "windows")]
+  println!("cargo:rustc-link-arg-bin={name}=/DEF:{}", symbols_path);
+
+  #[cfg(target_os = "macos")]
+  println!(
+    "cargo:rustc-link-arg-bin={name}=-Wl,-exported_symbols_list,{}",
+    symbols_path,
+  );
+
+  #[cfg(any(
+    target_os = "linux",
+    target_os = "freebsd",
+    target_os = "openbsd"
+  ))]
+  println!(
+    "cargo:rustc-link-arg-bin={name}=-Wl,--export-dynamic-symbol-list={}",
+    symbols_path,
+  );
+
+  #[cfg(target_os = "android")]
+  println!(
+    "cargo:rustc-link-arg-bin={name}=-Wl,--export-dynamic-symbol-list={}",
+    symbols_path,
+  );
+}
diff --git a/cli/napi/node_api.rs b/ext/napi/node_api.rs
similarity index 97%
rename from cli/napi/node_api.rs
rename to ext/napi/node_api.rs
index 81cb800a7d..2ca5c8d0b4 100644
--- a/cli/napi/node_api.rs
+++ b/ext/napi/node_api.rs
@@ -9,10 +9,10 @@ use super::util::napi_set_last_error;
 use super::util::SendPtr;
 use crate::check_arg;
 use crate::check_env;
+use crate::*;
 use deno_core::parking_lot::Condvar;
 use deno_core::parking_lot::Mutex;
 use deno_core::V8CrossThreadTaskSpawner;
-use deno_runtime::deno_napi::*;
 use napi_sym::napi_sym;
 use std::sync::atomic::AtomicBool;
 use std::sync::atomic::AtomicU8;
@@ -140,7 +140,6 @@ fn napi_fatal_exception(env: &mut Env, err: napi_value) -> napi_status {
 }
 
 #[napi_sym]
-#[allow(clippy::print_stderr)]
 fn napi_fatal_error(
   location: *const c_char,
   location_len: usize,
@@ -173,9 +172,9 @@ fn napi_fatal_error(
   };
 
   if let Some(location) = location {
-    eprintln!("NODE API FATAL ERROR: {} {}", location, message);
+    log::error!("NODE API FATAL ERROR: {} {}", location, message);
   } else {
-    eprintln!("NODE API FATAL ERROR: {}", message);
+    log::error!("NODE API FATAL ERROR: {}", message);
   }
 
   std::process::abort();
@@ -488,7 +487,7 @@ impl AsyncWork {
 }
 
 #[napi_sym]
-fn napi_create_async_work(
+pub(crate) fn napi_create_async_work(
   env: *mut Env,
   async_resource: napi_value,
   async_resource_name: napi_value,
@@ -537,7 +536,10 @@ fn napi_create_async_work(
 }
 
 #[napi_sym]
-fn napi_delete_async_work(env: *mut Env, work: napi_async_work) -> napi_status {
+pub(crate) fn napi_delete_async_work(
+  env: *mut Env,
+  work: napi_async_work,
+) -> napi_status {
   let env = check_env!(env);
   check_arg!(env, work);
 
@@ -547,15 +549,23 @@ fn napi_delete_async_work(env: *mut Env, work: napi_async_work) -> napi_status {
 }
 
 #[napi_sym]
-fn napi_get_uv_event_loop(env: *mut Env, uv_loop: *mut *mut ()) -> napi_status {
-  let env = check_env!(env);
+fn napi_get_uv_event_loop(
+  env_ptr: *mut Env,
+  uv_loop: *mut *mut (),
+) -> napi_status {
+  let env = check_env!(env_ptr);
   check_arg!(env, uv_loop);
-  // There is no uv_loop in Deno
-  napi_set_last_error(env, napi_generic_failure)
+  unsafe {
+    *uv_loop = env_ptr.cast();
+  }
+  0
 }
 
 #[napi_sym]
-fn napi_queue_async_work(env: *mut Env, work: napi_async_work) -> napi_status {
+pub(crate) fn napi_queue_async_work(
+  env: *mut Env,
+  work: napi_async_work,
+) -> napi_status {
   let env = check_env!(env);
   check_arg!(env, work);
 
@@ -687,7 +697,7 @@ impl Drop for TsFn {
 
     if let Some(finalizer) = self.thread_finalize_cb {
       unsafe {
-        (finalizer)(self.env as _, self.thread_finalize_data, ptr::null_mut());
+        (finalizer)(self.env as _, self.thread_finalize_data, self.context);
       }
     }
   }
@@ -892,7 +902,7 @@ fn napi_create_threadsafe_function(
   };
   let resource_name = resource_name.to_rust_string_lossy(&mut env.scope());
 
-  let mut tsfn = Box::new(TsFn {
+  let tsfn = Box::new(TsFn {
     env,
     func,
     max_queue_size,
diff --git a/cli/napi/sym/Cargo.toml b/ext/napi/sym/Cargo.toml
similarity index 95%
rename from cli/napi/sym/Cargo.toml
rename to ext/napi/sym/Cargo.toml
index eba5fa41cf..7c13a9165c 100644
--- a/cli/napi/sym/Cargo.toml
+++ b/ext/napi/sym/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "napi_sym"
-version = "0.98.0"
+version = "0.107.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/cli/napi/sym/README.md b/ext/napi/sym/README.md
similarity index 92%
rename from cli/napi/sym/README.md
rename to ext/napi/sym/README.md
index de08a8e174..66eb4bff26 100644
--- a/cli/napi/sym/README.md
+++ b/ext/napi/sym/README.md
@@ -2,7 +2,8 @@
 
 A proc_macro for Deno's Node-API implementation. It does the following things:
 
-- Marks the symbol as `#[no_mangle]` and rewrites it as `pub extern "C" $name`.
+- Marks the symbol as `#[no_mangle]` and rewrites it as
+  `unsafe extern "C" $name`.
 - Asserts that the function symbol is present in
   [`symbol_exports.json`](./symbol_exports.json).
 - Maps `deno_napi::Result` to raw `napi_result`.
diff --git a/cli/napi/sym/lib.rs b/ext/napi/sym/lib.rs
similarity index 100%
rename from cli/napi/sym/lib.rs
rename to ext/napi/sym/lib.rs
diff --git a/cli/napi/sym/symbol_exports.json b/ext/napi/sym/symbol_exports.json
similarity index 96%
rename from cli/napi/sym/symbol_exports.json
rename to ext/napi/sym/symbol_exports.json
index 64b548d496..00946b8ed7 100644
--- a/cli/napi/sym/symbol_exports.json
+++ b/ext/napi/sym/symbol_exports.json
@@ -152,6 +152,13 @@
     "napi_check_object_type_tag",
     "node_api_post_finalizer",
     "napi_add_async_cleanup_hook",
-    "napi_remove_async_cleanup_hook"
+    "napi_remove_async_cleanup_hook",
+    "uv_mutex_init",
+    "uv_mutex_lock",
+    "uv_mutex_unlock",
+    "uv_mutex_destroy",
+    "uv_async_init",
+    "uv_async_send",
+    "uv_close"
   ]
 }
diff --git a/cli/napi/util.rs b/ext/napi/util.rs
similarity index 84%
rename from cli/napi/util.rs
rename to ext/napi/util.rs
index 63d8effbf2..21e9d433aa 100644
--- a/cli/napi/util.rs
+++ b/ext/napi/util.rs
@@ -1,9 +1,9 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-use deno_runtime::deno_napi::*;
+use crate::*;
 use libc::INT_MAX;
 
 #[repr(transparent)]
-pub struct SendPtr<T>(pub *const T);
+pub(crate) struct SendPtr<T>(pub *const T);
 
 impl<T> SendPtr<T> {
   // silly function to get around `clippy::redundant_locals`
@@ -37,7 +37,7 @@ impl Drop for BufferFinalizer {
   }
 }
 
-pub extern "C" fn backing_store_deleter_callback(
+pub(crate) extern "C" fn backing_store_deleter_callback(
   data: *mut c_void,
   _byte_length: usize,
   deleter_data: *mut c_void,
@@ -50,7 +50,7 @@ pub extern "C" fn backing_store_deleter_callback(
   drop(finalizer);
 }
 
-pub fn make_external_backing_store(
+pub(crate) fn make_external_backing_store(
   env: *mut Env,
   data: *mut c_void,
   byte_length: usize,
@@ -90,9 +90,7 @@ macro_rules! check_env {
 macro_rules! return_error_status_if_false {
   ($env: expr, $condition: expr, $status: ident) => {
     if !$condition {
-      return Err(
-        $crate::napi::util::napi_set_last_error($env, $status).into(),
-      );
+      return Err($crate::util::napi_set_last_error($env, $status).into());
     }
   };
 }
@@ -101,7 +99,7 @@ macro_rules! return_error_status_if_false {
 macro_rules! return_status_if_false {
   ($env: expr, $condition: expr, $status: ident) => {
     if !$condition {
-      return $crate::napi::util::napi_set_last_error($env, $status);
+      return $crate::util::napi_set_last_error($env, $status);
     }
   };
 }
@@ -222,7 +220,7 @@ macro_rules! check_arg {
   ($env: expr, $ptr: expr) => {
     $crate::return_status_if_false!(
       $env,
-      !$crate::napi::util::Nullable::is_null(&$ptr),
+      !$crate::util::Nullable::is_null(&$ptr),
       napi_invalid_arg
     );
   };
@@ -230,17 +228,17 @@ macro_rules! check_arg {
 
 #[macro_export]
 macro_rules! napi_wrap {
-  ( $( # $attr:tt )* fn $name:ident $( < $( $x:lifetime ),* > )? ( $env:ident : & $( $lt:lifetime )? mut Env $( , $ident:ident : $ty:ty )* $(,)? ) -> napi_status $body:block ) => {
-    $( # $attr )*
+  ( $( # [ $attr:meta ] )* $vis:vis fn $name:ident $( < $( $x:lifetime ),* > )? ( $env:ident : & $( $lt:lifetime )? mut Env $( , $ident:ident : $ty:ty )* $(,)? ) -> napi_status $body:block ) => {
+    $( # [ $attr ] )*
     #[no_mangle]
-    pub unsafe extern "C" fn $name $( < $( $x ),* > )? ( env_ptr : *mut Env , $( $ident : $ty ),* ) -> napi_status {
+    $vis unsafe extern "C" fn $name $( < $( $x ),* > )? ( env_ptr : *mut Env , $( $ident : $ty ),* ) -> napi_status {
       let env: & $( $lt )? mut Env = $crate::check_env!(env_ptr);
 
       if env.last_exception.is_some() {
         return napi_pending_exception;
       }
 
-      $crate::napi::util::napi_clear_last_error(env);
+      $crate::util::napi_clear_last_error(env);
 
       let scope_env = unsafe { &mut *env_ptr };
       let scope = &mut scope_env.scope();
@@ -259,21 +257,21 @@ macro_rules! napi_wrap {
         let env = unsafe { &mut *env_ptr };
         let global = v8::Global::new(env.isolate(), exception);
         env.last_exception = Some(global);
-        return $crate::napi::util::napi_set_last_error(env_ptr, napi_pending_exception);
+        return $crate::util::napi_set_last_error(env_ptr, napi_pending_exception);
       }
 
       if result != napi_ok {
-        return $crate::napi::util::napi_set_last_error(env_ptr, result);
+        return $crate::util::napi_set_last_error(env_ptr, result);
       }
 
       return result;
     }
   };
 
-  ( $( # $attr:tt )* fn $name:ident $( < $( $x:lifetime ),* > )? ( $( $ident:ident : $ty:ty ),* $(,)? ) -> napi_status $body:block ) => {
-    $( # $attr )*
+  ( $( # [ $attr:meta ] )* $vis:vis fn $name:ident $( < $( $x:lifetime ),* > )? ( $( $ident:ident : $ty:ty ),* $(,)? ) -> napi_status $body:block ) => {
+    $( # [ $attr ] )*
     #[no_mangle]
-    pub unsafe extern "C" fn $name $( < $( $x ),* > )? ( $( $ident : $ty ),* ) -> napi_status {
+    $vis unsafe extern "C" fn $name $( < $( $x ),* > )? ( $( $ident : $ty ),* ) -> napi_status {
       #[inline(always)]
       fn inner $( < $( $x ),* > )? ( $( $ident : $ty ),* ) -> napi_status $body
 
diff --git a/ext/napi/uv.rs b/ext/napi/uv.rs
new file mode 100644
index 0000000000..ea6b539665
--- /dev/null
+++ b/ext/napi/uv.rs
@@ -0,0 +1,230 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+use crate::*;
+use deno_core::parking_lot::Mutex;
+use std::mem::MaybeUninit;
+use std::ptr::addr_of_mut;
+
+fn assert_ok(res: c_int) -> c_int {
+  if res != 0 {
+    log::error!("bad result in uv polyfill: {res}");
+    // don't panic because that might unwind into
+    // c/c++
+    std::process::abort();
+  }
+  res
+}
+
+use js_native_api::napi_create_string_utf8;
+use node_api::napi_create_async_work;
+use node_api::napi_delete_async_work;
+use node_api::napi_queue_async_work;
+use std::ffi::c_int;
+
+const UV_MUTEX_SIZE: usize = {
+  #[cfg(unix)]
+  {
+    std::mem::size_of::<libc::pthread_mutex_t>()
+  }
+  #[cfg(windows)]
+  {
+    std::mem::size_of::<windows_sys::Win32::System::Threading::CRITICAL_SECTION>(
+    )
+  }
+};
+
+#[repr(C)]
+struct uv_mutex_t {
+  mutex: Mutex<()>,
+  _padding: [MaybeUninit<usize>; const {
+    (UV_MUTEX_SIZE - size_of::<Mutex<()>>()) / size_of::<usize>()
+  }],
+}
+
+#[no_mangle]
+unsafe extern "C" fn uv_mutex_init(lock: *mut uv_mutex_t) -> c_int {
+  unsafe {
+    addr_of_mut!((*lock).mutex).write(Mutex::new(()));
+    0
+  }
+}
+
+#[no_mangle]
+unsafe extern "C" fn uv_mutex_lock(lock: *mut uv_mutex_t) {
+  unsafe {
+    let guard = (*lock).mutex.lock();
+    // forget the guard so it doesn't unlock when it goes out of scope.
+    // we're going to unlock it manually
+    std::mem::forget(guard);
+  }
+}
+
+#[no_mangle]
+unsafe extern "C" fn uv_mutex_unlock(lock: *mut uv_mutex_t) {
+  unsafe {
+    (*lock).mutex.force_unlock();
+  }
+}
+
+#[no_mangle]
+unsafe extern "C" fn uv_mutex_destroy(_lock: *mut uv_mutex_t) {
+  // no cleanup required
+}
+
+#[repr(C)]
+#[derive(Clone, Copy, Debug)]
+#[allow(dead_code)]
+enum uv_handle_type {
+  UV_UNKNOWN_HANDLE = 0,
+  UV_ASYNC,
+  UV_CHECK,
+  UV_FS_EVENT,
+  UV_FS_POLL,
+  UV_HANDLE,
+  UV_IDLE,
+  UV_NAMED_PIPE,
+  UV_POLL,
+  UV_PREPARE,
+  UV_PROCESS,
+  UV_STREAM,
+  UV_TCP,
+  UV_TIMER,
+  UV_TTY,
+  UV_UDP,
+  UV_SIGNAL,
+  UV_FILE,
+  UV_HANDLE_TYPE_MAX,
+}
+
+const UV_HANDLE_SIZE: usize = 96;
+
+#[repr(C)]
+struct uv_handle_t {
+  // public members
+  pub data: *mut c_void,
+  pub r#loop: *mut uv_loop_t,
+  pub r#type: uv_handle_type,
+
+  _padding: [MaybeUninit<usize>; const {
+    (UV_HANDLE_SIZE
+      - size_of::<*mut c_void>()
+      - size_of::<*mut uv_loop_t>()
+      - size_of::<uv_handle_type>())
+      / size_of::<usize>()
+  }],
+}
+
+#[cfg(unix)]
+const UV_ASYNC_SIZE: usize = 128;
+
+#[cfg(windows)]
+const UV_ASYNC_SIZE: usize = 224;
+
+#[repr(C)]
+struct uv_async_t {
+  // public members
+  pub data: *mut c_void,
+  pub r#loop: *mut uv_loop_t,
+  pub r#type: uv_handle_type,
+  // private
+  async_cb: uv_async_cb,
+  work: napi_async_work,
+  _padding: [MaybeUninit<usize>; const {
+    (UV_ASYNC_SIZE
+      - size_of::<*mut c_void>()
+      - size_of::<*mut uv_loop_t>()
+      - size_of::<uv_handle_type>()
+      - size_of::<uv_async_cb>()
+      - size_of::<napi_async_work>())
+      / size_of::<usize>()
+  }],
+}
+
+type uv_loop_t = Env;
+type uv_async_cb = extern "C" fn(handle: *mut uv_async_t);
+#[no_mangle]
+unsafe extern "C" fn uv_async_init(
+  r#loop: *mut uv_loop_t,
+  // probably uninitialized
+  r#async: *mut uv_async_t,
+  async_cb: uv_async_cb,
+) -> c_int {
+  unsafe {
+    addr_of_mut!((*r#async).r#loop).write(r#loop);
+    addr_of_mut!((*r#async).r#type).write(uv_handle_type::UV_ASYNC);
+    addr_of_mut!((*r#async).async_cb).write(async_cb);
+
+    let mut resource_name: MaybeUninit<napi_value> = MaybeUninit::uninit();
+    assert_ok(napi_create_string_utf8(
+      r#loop,
+      c"uv_async".as_ptr(),
+      usize::MAX,
+      resource_name.as_mut_ptr(),
+    ));
+    let resource_name = resource_name.assume_init();
+
+    let res = napi_create_async_work(
+      r#loop,
+      None::<v8::Local<'static, v8::Value>>.into(),
+      resource_name,
+      Some(async_exec_wrap),
+      None,
+      r#async.cast(),
+      addr_of_mut!((*r#async).work),
+    );
+    -res
+  }
+}
+
+#[no_mangle]
+unsafe extern "C" fn uv_async_send(handle: *mut uv_async_t) -> c_int {
+  unsafe { -napi_queue_async_work((*handle).r#loop, (*handle).work) }
+}
+
+type uv_close_cb = unsafe extern "C" fn(*mut uv_handle_t);
+
+#[no_mangle]
+unsafe extern "C" fn uv_close(handle: *mut uv_handle_t, close: uv_close_cb) {
+  unsafe {
+    if handle.is_null() {
+      close(handle);
+      return;
+    }
+    if let uv_handle_type::UV_ASYNC = (*handle).r#type {
+      let handle: *mut uv_async_t = handle.cast();
+      napi_delete_async_work((*handle).r#loop, (*handle).work);
+    }
+    close(handle);
+  }
+}
+
+unsafe extern "C" fn async_exec_wrap(_env: napi_env, data: *mut c_void) {
+  let data: *mut uv_async_t = data.cast();
+  unsafe {
+    ((*data).async_cb)(data);
+  }
+}
+
+#[cfg(test)]
+mod tests {
+  use super::*;
+
+  #[test]
+  fn sizes() {
+    assert_eq!(
+      std::mem::size_of::<libuv_sys_lite::uv_mutex_t>(),
+      UV_MUTEX_SIZE
+    );
+    assert_eq!(
+      std::mem::size_of::<libuv_sys_lite::uv_handle_t>(),
+      UV_HANDLE_SIZE
+    );
+    assert_eq!(
+      std::mem::size_of::<libuv_sys_lite::uv_async_t>(),
+      UV_ASYNC_SIZE
+    );
+    assert_eq!(std::mem::size_of::<uv_mutex_t>(), UV_MUTEX_SIZE);
+    assert_eq!(std::mem::size_of::<uv_handle_t>(), UV_HANDLE_SIZE);
+    assert_eq!(std::mem::size_of::<uv_async_t>(), UV_ASYNC_SIZE);
+  }
+}
diff --git a/ext/net/01_net.js b/ext/net/01_net.js
index 5b894947ee..c3e5f9e5ca 100644
--- a/ext/net/01_net.js
+++ b/ext/net/01_net.js
@@ -194,6 +194,20 @@ class Conn {
   }
 }
 
+class UpgradedConn extends Conn {
+  #rid = 0;
+
+  constructor(rid, remoteAddr, localAddr) {
+    super(rid, remoteAddr, localAddr);
+    ObjectDefineProperty(this, internalRidSymbol, {
+      __proto__: null,
+      enumerable: false,
+      value: rid,
+    });
+    this.#rid = rid;
+  }
+}
+
 class TcpConn extends Conn {
   #rid = 0;
 
@@ -601,5 +615,6 @@ export {
   resolveDns,
   TcpConn,
   UnixConn,
+  UpgradedConn,
   validatePort,
 };
diff --git a/ext/net/02_tls.js b/ext/net/02_tls.js
index 11d19440f7..6dad965590 100644
--- a/ext/net/02_tls.js
+++ b/ext/net/02_tls.js
@@ -124,17 +124,19 @@ function loadTlsKeyPair(api, {
 
   // Check for "pem" format
   if (keyFormat !== undefined && keyFormat !== "pem") {
-    throw new TypeError('If `keyFormat` is specified, it must be "pem"');
+    throw new TypeError(
+      `If "keyFormat" is specified, it must be "pem": received "${keyFormat}"`,
+    );
   }
 
   if (cert !== undefined && key === undefined) {
     throw new TypeError(
-      `If \`cert\` is specified, \`key\` must be specified as well for \`${api}\`.`,
+      `If \`cert\` is specified, \`key\` must be specified as well for \`${api}\``,
     );
   }
   if (cert === undefined && key !== undefined) {
     throw new TypeError(
-      `If \`key\` is specified, \`cert\` must be specified as well for \`${api}\`.`,
+      `If \`key\` is specified, \`cert\` must be specified as well for \`${api}\``,
     );
   }
 
diff --git a/ext/net/Cargo.toml b/ext/net/Cargo.toml
index 02e7a16818..245deedd2d 100644
--- a/ext/net/Cargo.toml
+++ b/ext/net/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_net"
-version = "0.160.0"
+version = "0.169.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -17,10 +17,11 @@ path = "lib.rs"
 deno_core.workspace = true
 deno_permissions.workspace = true
 deno_tls.workspace = true
+hickory-proto = "0.24"
+hickory-resolver = { version = "0.24", features = ["tokio-runtime", "serde-config"] }
 pin-project.workspace = true
 rustls-tokio-stream.workspace = true
 serde.workspace = true
 socket2.workspace = true
+thiserror.workspace = true
 tokio.workspace = true
-trust-dns-proto = "0.23"
-trust-dns-resolver = { version = "0.23", features = ["tokio-runtime", "serde-config"] }
diff --git a/ext/net/io.rs b/ext/net/io.rs
index f3aed3fcbd..2907fa398b 100644
--- a/ext/net/io.rs
+++ b/ext/net/io.rs
@@ -1,7 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::generic_error;
-use deno_core::error::AnyError;
+use deno_core::futures::TryFutureExt;
 use deno_core::AsyncMutFuture;
 use deno_core::AsyncRefCell;
 use deno_core::AsyncResult;
@@ -69,25 +68,36 @@ where
   pub async fn read(
     self: Rc<Self>,
     data: &mut [u8],
-  ) -> Result<usize, AnyError> {
+  ) -> Result<usize, std::io::Error> {
     let mut rd = self.rd_borrow_mut().await;
     let nread = rd.read(data).try_or_cancel(self.cancel_handle()).await?;
     Ok(nread)
   }
 
-  pub async fn write(self: Rc<Self>, data: &[u8]) -> Result<usize, AnyError> {
+  pub async fn write(
+    self: Rc<Self>,
+    data: &[u8],
+  ) -> Result<usize, std::io::Error> {
     let mut wr = self.wr_borrow_mut().await;
     let nwritten = wr.write(data).await?;
     Ok(nwritten)
   }
 
-  pub async fn shutdown(self: Rc<Self>) -> Result<(), AnyError> {
+  pub async fn shutdown(self: Rc<Self>) -> Result<(), std::io::Error> {
     let mut wr = self.wr_borrow_mut().await;
     wr.shutdown().await?;
     Ok(())
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum MapError {
+  #[error("{0}")]
+  Io(std::io::Error),
+  #[error("Unable to get resources")]
+  NoResources,
+}
+
 pub type TcpStreamResource =
   FullDuplexResource<tcp::OwnedReadHalf, tcp::OwnedWriteHalf>;
 
@@ -100,7 +110,7 @@ impl Resource for TcpStreamResource {
   }
 
   fn shutdown(self: Rc<Self>) -> AsyncResult<()> {
-    Box::pin(self.shutdown())
+    Box::pin(self.shutdown().map_err(Into::into))
   }
 
   fn close(self: Rc<Self>) {
@@ -109,31 +119,30 @@ impl Resource for TcpStreamResource {
 }
 
 impl TcpStreamResource {
-  pub fn set_nodelay(self: Rc<Self>, nodelay: bool) -> Result<(), AnyError> {
-    self.map_socket(Box::new(move |socket| Ok(socket.set_nodelay(nodelay)?)))
+  pub fn set_nodelay(self: Rc<Self>, nodelay: bool) -> Result<(), MapError> {
+    self.map_socket(Box::new(move |socket| socket.set_nodelay(nodelay)))
   }
 
   pub fn set_keepalive(
     self: Rc<Self>,
     keepalive: bool,
-  ) -> Result<(), AnyError> {
-    self
-      .map_socket(Box::new(move |socket| Ok(socket.set_keepalive(keepalive)?)))
+  ) -> Result<(), MapError> {
+    self.map_socket(Box::new(move |socket| socket.set_keepalive(keepalive)))
   }
 
   #[allow(clippy::type_complexity)]
   fn map_socket(
     self: Rc<Self>,
-    map: Box<dyn FnOnce(SockRef) -> Result<(), AnyError>>,
-  ) -> Result<(), AnyError> {
+    map: Box<dyn FnOnce(SockRef) -> Result<(), std::io::Error>>,
+  ) -> Result<(), MapError> {
     if let Some(wr) = RcRef::map(self, |r| &r.wr).try_borrow() {
       let stream = wr.as_ref().as_ref();
       let socket = socket2::SockRef::from(stream);
 
-      return map(socket);
+      return map(socket).map_err(MapError::Io);
     }
 
-    Err(generic_error("Unable to get resources"))
+    Err(MapError::NoResources)
   }
 }
 
@@ -153,7 +162,9 @@ impl UnixStreamResource {
     unreachable!()
   }
   #[allow(clippy::unused_async)]
-  pub async fn shutdown(self: Rc<Self>) -> Result<(), AnyError> {
+  pub async fn shutdown(
+    self: Rc<Self>,
+  ) -> Result<(), deno_core::error::AnyError> {
     unreachable!()
   }
   pub fn cancel_read_ops(&self) {
@@ -170,7 +181,7 @@ impl Resource for UnixStreamResource {
   }
 
   fn shutdown(self: Rc<Self>) -> AsyncResult<()> {
-    Box::pin(self.shutdown())
+    Box::pin(self.shutdown().map_err(Into::into))
   }
 
   fn close(self: Rc<Self>) {
diff --git a/ext/net/lib.rs b/ext/net/lib.rs
index b039965d4c..bf8f58aa27 100644
--- a/ext/net/lib.rs
+++ b/ext/net/lib.rs
@@ -11,6 +11,7 @@ mod tcp;
 
 use deno_core::error::AnyError;
 use deno_core::OpState;
+use deno_permissions::PermissionCheckError;
 use deno_tls::rustls::RootCertStore;
 use deno_tls::RootCertStoreProvider;
 use std::borrow::Cow;
@@ -25,25 +26,25 @@ pub trait NetPermissions {
     &mut self,
     host: &(T, Option<u16>),
     api_name: &str,
-  ) -> Result<(), AnyError>;
+  ) -> Result<(), PermissionCheckError>;
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
   fn check_read(
     &mut self,
     p: &str,
     api_name: &str,
-  ) -> Result<PathBuf, AnyError>;
+  ) -> Result<PathBuf, PermissionCheckError>;
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
   fn check_write(
     &mut self,
     p: &str,
     api_name: &str,
-  ) -> Result<PathBuf, AnyError>;
+  ) -> Result<PathBuf, PermissionCheckError>;
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
   fn check_write_path<'a>(
     &mut self,
     p: &'a Path,
     api_name: &str,
-  ) -> Result<Cow<'a, Path>, AnyError>;
+  ) -> Result<Cow<'a, Path>, PermissionCheckError>;
 }
 
 impl NetPermissions for deno_permissions::PermissionsContainer {
@@ -52,7 +53,7 @@ impl NetPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     host: &(T, Option<u16>),
     api_name: &str,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_net(self, host, api_name)
   }
 
@@ -61,7 +62,7 @@ impl NetPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     path: &str,
     api_name: &str,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_read(self, path, api_name)
   }
 
@@ -70,7 +71,7 @@ impl NetPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     path: &str,
     api_name: &str,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_write(self, path, api_name)
   }
 
@@ -79,7 +80,7 @@ impl NetPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     path: &'a Path,
     api_name: &str,
-  ) -> Result<Cow<'a, Path>, AnyError> {
+  ) -> Result<Cow<'a, Path>, PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_write_path(
       self, path, api_name,
     )
diff --git a/ext/net/ops.rs b/ext/net/ops.rs
index 5248493f41..9a8b70f0f6 100644
--- a/ext/net/ops.rs
+++ b/ext/net/ops.rs
@@ -6,10 +6,6 @@ use crate::resolve_addr::resolve_addr;
 use crate::resolve_addr::resolve_addr_sync;
 use crate::tcp::TcpListener;
 use crate::NetPermissions;
-use deno_core::error::bad_resource;
-use deno_core::error::custom_error;
-use deno_core::error::generic_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::CancelFuture;
 
@@ -22,6 +18,16 @@ use deno_core::OpState;
 use deno_core::RcRef;
 use deno_core::Resource;
 use deno_core::ResourceId;
+use hickory_proto::rr::rdata::caa::Value;
+use hickory_proto::rr::record_data::RData;
+use hickory_proto::rr::record_type::RecordType;
+use hickory_resolver::config::NameServerConfigGroup;
+use hickory_resolver::config::ResolverConfig;
+use hickory_resolver::config::ResolverOpts;
+use hickory_resolver::error::ResolveError;
+use hickory_resolver::error::ResolveErrorKind;
+use hickory_resolver::system_conf;
+use hickory_resolver::AsyncResolver;
 use serde::Deserialize;
 use serde::Serialize;
 use socket2::Domain;
@@ -37,15 +43,6 @@ use std::rc::Rc;
 use std::str::FromStr;
 use tokio::net::TcpStream;
 use tokio::net::UdpSocket;
-use trust_dns_proto::rr::rdata::caa::Value;
-use trust_dns_proto::rr::record_data::RData;
-use trust_dns_proto::rr::record_type::RecordType;
-use trust_dns_resolver::config::NameServerConfigGroup;
-use trust_dns_resolver::config::ResolverConfig;
-use trust_dns_resolver::config::ResolverOpts;
-use trust_dns_resolver::error::ResolveErrorKind;
-use trust_dns_resolver::system_conf;
-use trust_dns_resolver::AsyncResolver;
 
 #[derive(Serialize, Clone, Debug)]
 #[serde(rename_all = "camelCase")]
@@ -68,11 +65,69 @@ impl From<SocketAddr> for IpAddr {
   }
 }
 
-pub(crate) fn accept_err(e: std::io::Error) -> AnyError {
+#[derive(Debug, thiserror::Error)]
+pub enum NetError {
+  #[error("Listener has been closed")]
+  ListenerClosed,
+  #[error("Listener already in use")]
+  ListenerBusy,
+  #[error("Socket has been closed")]
+  SocketClosed,
+  #[error("Socket has been closed")]
+  SocketClosedNotConnected,
+  #[error("Socket already in use")]
+  SocketBusy,
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[error("Another accept task is ongoing")]
+  AcceptTaskOngoing,
+  #[error(transparent)]
+  Permission(#[from] deno_permissions::PermissionCheckError),
+  #[error("{0}")]
+  Resource(deno_core::error::AnyError),
+  #[error("No resolved address found")]
+  NoResolvedAddress,
+  #[error("{0}")]
+  AddrParse(#[from] std::net::AddrParseError),
+  #[error("{0}")]
+  Map(crate::io::MapError),
+  #[error("{0}")]
+  Canceled(#[from] deno_core::Canceled),
+  #[error("{0}")]
+  DnsNotFound(ResolveError),
+  #[error("{0}")]
+  DnsNotConnected(ResolveError),
+  #[error("{0}")]
+  DnsTimedOut(ResolveError),
+  #[error("{0}")]
+  Dns(#[from] ResolveError),
+  #[error("Provided record type is not supported")]
+  UnsupportedRecordType,
+  #[error("File name or path {0:?} is not valid UTF-8")]
+  InvalidUtf8(std::ffi::OsString),
+  #[error("unexpected key type")]
+  UnexpectedKeyType,
+  #[error("Invalid hostname: '{0}'")]
+  InvalidHostname(String), // TypeError
+  #[error("TCP stream is currently in use")]
+  TcpStreamBusy,
+  #[error("{0}")]
+  Rustls(#[from] deno_tls::rustls::Error),
+  #[error("{0}")]
+  Tls(#[from] deno_tls::TlsError),
+  #[error("Error creating TLS certificate: Deno.listenTls requires a key")]
+  ListenTlsRequiresKey, // InvalidData
+  #[error("{0}")]
+  RootCertStore(deno_core::anyhow::Error),
+  #[error("{0}")]
+  Reunite(tokio::net::tcp::ReuniteError),
+}
+
+pub(crate) fn accept_err(e: std::io::Error) -> NetError {
   if let std::io::ErrorKind::Interrupted = e.kind() {
-    bad_resource("Listener has been closed")
+    NetError::ListenerClosed
   } else {
-    e.into()
+    NetError::Io(e)
   }
 }
 
@@ -81,15 +136,15 @@ pub(crate) fn accept_err(e: std::io::Error) -> AnyError {
 pub async fn op_net_accept_tcp(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(ResourceId, IpAddr, IpAddr), AnyError> {
+) -> Result<(ResourceId, IpAddr, IpAddr), NetError> {
   let resource = state
     .borrow()
     .resource_table
     .get::<NetworkListenerResource<TcpListener>>(rid)
-    .map_err(|_| bad_resource("Listener has been closed"))?;
+    .map_err(|_| NetError::ListenerClosed)?;
   let listener = RcRef::map(&resource, |r| &r.listener)
     .try_borrow_mut()
-    .ok_or_else(|| custom_error("Busy", "Another accept task is ongoing"))?;
+    .ok_or_else(|| NetError::AcceptTaskOngoing)?;
   let cancel = RcRef::map(resource, |r| &r.cancel);
   let (tcp_stream, _socket_addr) = listener
     .accept()
@@ -112,12 +167,12 @@ pub async fn op_net_recv_udp(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[buffer] mut buf: JsBuffer,
-) -> Result<(usize, IpAddr), AnyError> {
+) -> Result<(usize, IpAddr), NetError> {
   let resource = state
     .borrow_mut()
     .resource_table
     .get::<UdpSocketResource>(rid)
-    .map_err(|_| bad_resource("Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosed)?;
   let socket = RcRef::map(&resource, |r| &r.socket).borrow().await;
   let cancel_handle = RcRef::map(&resource, |r| &r.cancel);
   let (nread, remote_addr) = socket
@@ -134,7 +189,7 @@ pub async fn op_net_send_udp<NP>(
   #[smi] rid: ResourceId,
   #[serde] addr: IpAddr,
   #[buffer] zero_copy: JsBuffer,
-) -> Result<usize, AnyError>
+) -> Result<usize, NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -148,13 +203,13 @@ where
   let addr = resolve_addr(&addr.hostname, addr.port)
     .await?
     .next()
-    .ok_or_else(|| generic_error("No resolved address found"))?;
+    .ok_or(NetError::NoResolvedAddress)?;
 
   let resource = state
     .borrow_mut()
     .resource_table
     .get::<UdpSocketResource>(rid)
-    .map_err(|_| bad_resource("Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosed)?;
   let socket = RcRef::map(&resource, |r| &r.socket).borrow().await;
   let nwritten = socket.send_to(&zero_copy, &addr).await?;
 
@@ -167,12 +222,12 @@ pub async fn op_net_join_multi_v4_udp(
   #[smi] rid: ResourceId,
   #[string] address: String,
   #[string] multi_interface: String,
-) -> Result<(), AnyError> {
+) -> Result<(), NetError> {
   let resource = state
     .borrow_mut()
     .resource_table
     .get::<UdpSocketResource>(rid)
-    .map_err(|_| bad_resource("Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosed)?;
   let socket = RcRef::map(&resource, |r| &r.socket).borrow().await;
 
   let addr = Ipv4Addr::from_str(address.as_str())?;
@@ -189,12 +244,12 @@ pub async fn op_net_join_multi_v6_udp(
   #[smi] rid: ResourceId,
   #[string] address: String,
   #[smi] multi_interface: u32,
-) -> Result<(), AnyError> {
+) -> Result<(), NetError> {
   let resource = state
     .borrow_mut()
     .resource_table
     .get::<UdpSocketResource>(rid)
-    .map_err(|_| bad_resource("Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosed)?;
   let socket = RcRef::map(&resource, |r| &r.socket).borrow().await;
 
   let addr = Ipv6Addr::from_str(address.as_str())?;
@@ -210,12 +265,12 @@ pub async fn op_net_leave_multi_v4_udp(
   #[smi] rid: ResourceId,
   #[string] address: String,
   #[string] multi_interface: String,
-) -> Result<(), AnyError> {
+) -> Result<(), NetError> {
   let resource = state
     .borrow_mut()
     .resource_table
     .get::<UdpSocketResource>(rid)
-    .map_err(|_| bad_resource("Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosed)?;
   let socket = RcRef::map(&resource, |r| &r.socket).borrow().await;
 
   let addr = Ipv4Addr::from_str(address.as_str())?;
@@ -232,12 +287,12 @@ pub async fn op_net_leave_multi_v6_udp(
   #[smi] rid: ResourceId,
   #[string] address: String,
   #[smi] multi_interface: u32,
-) -> Result<(), AnyError> {
+) -> Result<(), NetError> {
   let resource = state
     .borrow_mut()
     .resource_table
     .get::<UdpSocketResource>(rid)
-    .map_err(|_| bad_resource("Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosed)?;
   let socket = RcRef::map(&resource, |r| &r.socket).borrow().await;
 
   let addr = Ipv6Addr::from_str(address.as_str())?;
@@ -253,16 +308,16 @@ pub async fn op_net_set_multi_loopback_udp(
   #[smi] rid: ResourceId,
   is_v4_membership: bool,
   loopback: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), NetError> {
   let resource = state
     .borrow_mut()
     .resource_table
     .get::<UdpSocketResource>(rid)
-    .map_err(|_| bad_resource("Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosed)?;
   let socket = RcRef::map(&resource, |r| &r.socket).borrow().await;
 
   if is_v4_membership {
-    socket.set_multicast_loop_v4(loopback)?
+    socket.set_multicast_loop_v4(loopback)?;
   } else {
     socket.set_multicast_loop_v6(loopback)?;
   }
@@ -275,12 +330,12 @@ pub async fn op_net_set_multi_ttl_udp(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[smi] ttl: u32,
-) -> Result<(), AnyError> {
+) -> Result<(), NetError> {
   let resource = state
     .borrow_mut()
     .resource_table
     .get::<UdpSocketResource>(rid)
-    .map_err(|_| bad_resource("Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosed)?;
   let socket = RcRef::map(&resource, |r| &r.socket).borrow().await;
 
   socket.set_multicast_ttl_v4(ttl)?;
@@ -293,7 +348,7 @@ pub async fn op_net_set_multi_ttl_udp(
 pub async fn op_net_connect_tcp<NP>(
   state: Rc<RefCell<OpState>>,
   #[serde] addr: IpAddr,
-) -> Result<(ResourceId, IpAddr, IpAddr), AnyError>
+) -> Result<(ResourceId, IpAddr, IpAddr), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -304,7 +359,7 @@ where
 pub async fn op_net_connect_tcp_inner<NP>(
   state: Rc<RefCell<OpState>>,
   addr: IpAddr,
-) -> Result<(ResourceId, IpAddr, IpAddr), AnyError>
+) -> Result<(ResourceId, IpAddr, IpAddr), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -318,7 +373,7 @@ where
   let addr = resolve_addr(&addr.hostname, addr.port)
     .await?
     .next()
-    .ok_or_else(|| generic_error("No resolved address found"))?;
+    .ok_or_else(|| NetError::NoResolvedAddress)?;
   let tcp_stream = TcpStream::connect(&addr).await?;
   let local_addr = tcp_stream.local_addr()?;
   let remote_addr = tcp_stream.peer_addr()?;
@@ -353,7 +408,7 @@ pub fn op_net_listen_tcp<NP>(
   #[serde] addr: IpAddr,
   reuse_port: bool,
   load_balanced: bool,
-) -> Result<(ResourceId, IpAddr), AnyError>
+) -> Result<(ResourceId, IpAddr), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -365,7 +420,7 @@ where
     .check_net(&(&addr.hostname, Some(addr.port)), "Deno.listen()")?;
   let addr = resolve_addr_sync(&addr.hostname, addr.port)?
     .next()
-    .ok_or_else(|| generic_error("No resolved address found"))?;
+    .ok_or_else(|| NetError::NoResolvedAddress)?;
 
   let listener = if load_balanced {
     TcpListener::bind_load_balanced(addr)
@@ -384,7 +439,7 @@ fn net_listen_udp<NP>(
   addr: IpAddr,
   reuse_address: bool,
   loopback: bool,
-) -> Result<(ResourceId, IpAddr), AnyError>
+) -> Result<(ResourceId, IpAddr), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -393,7 +448,7 @@ where
     .check_net(&(&addr.hostname, Some(addr.port)), "Deno.listenDatagram()")?;
   let addr = resolve_addr_sync(&addr.hostname, addr.port)?
     .next()
-    .ok_or_else(|| generic_error("No resolved address found"))?;
+    .ok_or_else(|| NetError::NoResolvedAddress)?;
 
   let domain = if addr.is_ipv4() {
     Domain::IPV4
@@ -453,7 +508,7 @@ pub fn op_net_listen_udp<NP>(
   #[serde] addr: IpAddr,
   reuse_address: bool,
   loopback: bool,
-) -> Result<(ResourceId, IpAddr), AnyError>
+) -> Result<(ResourceId, IpAddr), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -468,7 +523,7 @@ pub fn op_node_unstable_net_listen_udp<NP>(
   #[serde] addr: IpAddr,
   reuse_address: bool,
   loopback: bool,
-) -> Result<(ResourceId, IpAddr), AnyError>
+) -> Result<(ResourceId, IpAddr), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -551,7 +606,7 @@ pub struct NameServer {
 pub async fn op_dns_resolve<NP>(
   state: Rc<RefCell<OpState>>,
   #[serde] args: ResolveAddrArgs,
-) -> Result<Vec<DnsReturnRecord>, AnyError>
+) -> Result<Vec<DnsReturnRecord>, NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -618,22 +673,17 @@ where
   };
 
   lookup
-    .map_err(|e| {
-      let message = format!("{e}");
-      match e.kind() {
-        ResolveErrorKind::NoRecordsFound { .. } => {
-          custom_error("NotFound", message)
-        }
-        ResolveErrorKind::Message("No connections available") => {
-          custom_error("NotConnected", message)
-        }
-        ResolveErrorKind::Timeout => custom_error("TimedOut", message),
-        _ => generic_error(message),
+    .map_err(|e| match e.kind() {
+      ResolveErrorKind::NoRecordsFound { .. } => NetError::DnsNotFound(e),
+      ResolveErrorKind::Message("No connections available") => {
+        NetError::DnsNotConnected(e)
       }
+      ResolveErrorKind::Timeout => NetError::DnsTimedOut(e),
+      _ => NetError::Dns(e),
     })?
     .iter()
     .filter_map(|rdata| rdata_to_return_record(record_type)(rdata).transpose())
-    .collect::<Result<Vec<DnsReturnRecord>, AnyError>>()
+    .collect::<Result<Vec<DnsReturnRecord>, NetError>>()
 }
 
 #[op2(fast)]
@@ -641,7 +691,7 @@ pub fn op_set_nodelay(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   nodelay: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), NetError> {
   op_set_nodelay_inner(state, rid, nodelay)
 }
 
@@ -650,10 +700,12 @@ pub fn op_set_nodelay_inner(
   state: &mut OpState,
   rid: ResourceId,
   nodelay: bool,
-) -> Result<(), AnyError> {
-  let resource: Rc<TcpStreamResource> =
-    state.resource_table.get::<TcpStreamResource>(rid)?;
-  resource.set_nodelay(nodelay)
+) -> Result<(), NetError> {
+  let resource: Rc<TcpStreamResource> = state
+    .resource_table
+    .get::<TcpStreamResource>(rid)
+    .map_err(NetError::Resource)?;
+  resource.set_nodelay(nodelay).map_err(NetError::Map)
 }
 
 #[op2(fast)]
@@ -661,7 +713,7 @@ pub fn op_set_keepalive(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   keepalive: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), NetError> {
   op_set_keepalive_inner(state, rid, keepalive)
 }
 
@@ -670,17 +722,19 @@ pub fn op_set_keepalive_inner(
   state: &mut OpState,
   rid: ResourceId,
   keepalive: bool,
-) -> Result<(), AnyError> {
-  let resource: Rc<TcpStreamResource> =
-    state.resource_table.get::<TcpStreamResource>(rid)?;
-  resource.set_keepalive(keepalive)
+) -> Result<(), NetError> {
+  let resource: Rc<TcpStreamResource> = state
+    .resource_table
+    .get::<TcpStreamResource>(rid)
+    .map_err(NetError::Resource)?;
+  resource.set_keepalive(keepalive).map_err(NetError::Map)
 }
 
 fn rdata_to_return_record(
   ty: RecordType,
-) -> impl Fn(&RData) -> Result<Option<DnsReturnRecord>, AnyError> {
+) -> impl Fn(&RData) -> Result<Option<DnsReturnRecord>, NetError> {
   use RecordType::*;
-  move |r: &RData| -> Result<Option<DnsReturnRecord>, AnyError> {
+  move |r: &RData| -> Result<Option<DnsReturnRecord>, NetError> {
     let record = match ty {
       A => r.as_a().map(ToString::to_string).map(DnsReturnRecord::A),
       AAAA => r
@@ -761,12 +815,7 @@ fn rdata_to_return_record(
           .collect();
         DnsReturnRecord::Txt(texts)
       }),
-      _ => {
-        return Err(custom_error(
-          "NotSupported",
-          "Provided record type is not supported",
-        ))
-      }
+      _ => return Err(NetError::UnsupportedRecordType),
     };
     Ok(record)
   }
@@ -778,6 +827,22 @@ mod tests {
   use deno_core::futures::FutureExt;
   use deno_core::JsRuntime;
   use deno_core::RuntimeOptions;
+  use deno_permissions::PermissionCheckError;
+  use hickory_proto::rr::rdata::a::A;
+  use hickory_proto::rr::rdata::aaaa::AAAA;
+  use hickory_proto::rr::rdata::caa::KeyValue;
+  use hickory_proto::rr::rdata::caa::CAA;
+  use hickory_proto::rr::rdata::mx::MX;
+  use hickory_proto::rr::rdata::name::ANAME;
+  use hickory_proto::rr::rdata::name::CNAME;
+  use hickory_proto::rr::rdata::name::NS;
+  use hickory_proto::rr::rdata::name::PTR;
+  use hickory_proto::rr::rdata::naptr::NAPTR;
+  use hickory_proto::rr::rdata::srv::SRV;
+  use hickory_proto::rr::rdata::txt::TXT;
+  use hickory_proto::rr::rdata::SOA;
+  use hickory_proto::rr::record_data::RData;
+  use hickory_proto::rr::Name;
   use socket2::SockRef;
   use std::net::Ipv4Addr;
   use std::net::Ipv6Addr;
@@ -786,21 +851,6 @@ mod tests {
   use std::path::PathBuf;
   use std::sync::Arc;
   use std::sync::Mutex;
-  use trust_dns_proto::rr::rdata::a::A;
-  use trust_dns_proto::rr::rdata::aaaa::AAAA;
-  use trust_dns_proto::rr::rdata::caa::KeyValue;
-  use trust_dns_proto::rr::rdata::caa::CAA;
-  use trust_dns_proto::rr::rdata::mx::MX;
-  use trust_dns_proto::rr::rdata::name::ANAME;
-  use trust_dns_proto::rr::rdata::name::CNAME;
-  use trust_dns_proto::rr::rdata::name::NS;
-  use trust_dns_proto::rr::rdata::name::PTR;
-  use trust_dns_proto::rr::rdata::naptr::NAPTR;
-  use trust_dns_proto::rr::rdata::srv::SRV;
-  use trust_dns_proto::rr::rdata::txt::TXT;
-  use trust_dns_proto::rr::rdata::SOA;
-  use trust_dns_proto::rr::record_data::RData;
-  use trust_dns_proto::rr::Name;
 
   #[test]
   fn rdata_to_return_record_a() {
@@ -985,7 +1035,7 @@ mod tests {
       &mut self,
       _host: &(T, Option<u16>),
       _api_name: &str,
-    ) -> Result<(), AnyError> {
+    ) -> Result<(), PermissionCheckError> {
       Ok(())
     }
 
@@ -993,7 +1043,7 @@ mod tests {
       &mut self,
       p: &str,
       _api_name: &str,
-    ) -> Result<PathBuf, AnyError> {
+    ) -> Result<PathBuf, PermissionCheckError> {
       Ok(PathBuf::from(p))
     }
 
@@ -1001,7 +1051,7 @@ mod tests {
       &mut self,
       p: &str,
       _api_name: &str,
-    ) -> Result<PathBuf, AnyError> {
+    ) -> Result<PathBuf, PermissionCheckError> {
       Ok(PathBuf::from(p))
     }
 
@@ -1009,7 +1059,7 @@ mod tests {
       &mut self,
       p: &'a Path,
       _api_name: &str,
-    ) -> Result<Cow<'a, Path>, AnyError> {
+    ) -> Result<Cow<'a, Path>, PermissionCheckError> {
       Ok(Cow::Borrowed(p))
     }
   }
@@ -1091,7 +1141,7 @@ mod tests {
         let vals = result.unwrap();
         rid = rid.or(Some(vals.0));
       }
-    };
+    }
     let rid = rid.unwrap();
 
     let state = runtime.op_state();
diff --git a/ext/net/ops_tls.rs b/ext/net/ops_tls.rs
index 5bc04ceb51..c7d65dd85e 100644
--- a/ext/net/ops_tls.rs
+++ b/ext/net/ops_tls.rs
@@ -2,6 +2,7 @@
 
 use crate::io::TcpStreamResource;
 use crate::ops::IpAddr;
+use crate::ops::NetError;
 use crate::ops::TlsHandshakeInfo;
 use crate::raw::NetworkListenerResource;
 use crate::resolve_addr::resolve_addr;
@@ -10,13 +11,7 @@ use crate::tcp::TcpListener;
 use crate::DefaultTlsOptions;
 use crate::NetPermissions;
 use crate::UnsafelyIgnoreCertificateErrors;
-use deno_core::anyhow::anyhow;
-use deno_core::anyhow::bail;
-use deno_core::error::bad_resource;
-use deno_core::error::custom_error;
-use deno_core::error::generic_error;
-use deno_core::error::invalid_hostname;
-use deno_core::error::AnyError;
+use deno_core::futures::TryFutureExt;
 use deno_core::op2;
 use deno_core::v8;
 use deno_core::AsyncRefCell;
@@ -118,20 +113,23 @@ impl TlsStreamResource {
   pub async fn read(
     self: Rc<Self>,
     data: &mut [u8],
-  ) -> Result<usize, AnyError> {
+  ) -> Result<usize, std::io::Error> {
     let mut rd = RcRef::map(&self, |r| &r.rd).borrow_mut().await;
     let cancel_handle = RcRef::map(&self, |r| &r.cancel_handle);
-    Ok(rd.read(data).try_or_cancel(cancel_handle).await?)
+    rd.read(data).try_or_cancel(cancel_handle).await
   }
 
-  pub async fn write(self: Rc<Self>, data: &[u8]) -> Result<usize, AnyError> {
+  pub async fn write(
+    self: Rc<Self>,
+    data: &[u8],
+  ) -> Result<usize, std::io::Error> {
     let mut wr = RcRef::map(self, |r| &r.wr).borrow_mut().await;
     let nwritten = wr.write(data).await?;
     wr.flush().await?;
     Ok(nwritten)
   }
 
-  pub async fn shutdown(self: Rc<Self>) -> Result<(), AnyError> {
+  pub async fn shutdown(self: Rc<Self>) -> Result<(), std::io::Error> {
     let mut wr = RcRef::map(self, |r| &r.wr).borrow_mut().await;
     wr.shutdown().await?;
     Ok(())
@@ -139,7 +137,7 @@ impl TlsStreamResource {
 
   pub async fn handshake(
     self: &Rc<Self>,
-  ) -> Result<TlsHandshakeInfo, AnyError> {
+  ) -> Result<TlsHandshakeInfo, std::io::Error> {
     if let Some(tls_info) = &*self.handshake_info.borrow() {
       return Ok(tls_info.clone());
     }
@@ -164,7 +162,7 @@ impl Resource for TlsStreamResource {
   }
 
   fn shutdown(self: Rc<Self>) -> AsyncResult<()> {
-    Box::pin(self.shutdown())
+    Box::pin(self.shutdown().map_err(Into::into))
   }
 
   fn close(self: Rc<Self>) {
@@ -201,7 +199,7 @@ pub fn op_tls_key_null() -> TlsKeysHolder {
 pub fn op_tls_key_static(
   #[string] cert: &str,
   #[string] key: &str,
-) -> Result<TlsKeysHolder, AnyError> {
+) -> Result<TlsKeysHolder, deno_tls::TlsError> {
   let cert = load_certs(&mut BufReader::new(cert.as_bytes()))?;
   let key = load_private_keys(key.as_bytes())?
     .into_iter()
@@ -236,9 +234,9 @@ pub fn op_tls_cert_resolver_resolve(
   #[cppgc] lookup: &TlsKeyLookup,
   #[string] sni: String,
   #[cppgc] key: &TlsKeysHolder,
-) -> Result<(), AnyError> {
+) -> Result<(), NetError> {
   let TlsKeys::Static(key) = key.take() else {
-    bail!("unexpected key type");
+    return Err(NetError::UnexpectedKeyType);
   };
   lookup.resolve(sni, Ok(key));
   Ok(())
@@ -250,7 +248,7 @@ pub fn op_tls_cert_resolver_resolve_error(
   #[string] sni: String,
   #[string] error: String,
 ) {
-  lookup.resolve(sni, Err(anyhow!(error)))
+  lookup.resolve(sni, Err(error))
 }
 
 #[op2]
@@ -258,7 +256,7 @@ pub fn op_tls_cert_resolver_resolve_error(
 pub fn op_tls_start<NP>(
   state: Rc<RefCell<OpState>>,
   #[serde] args: StartTlsArgs,
-) -> Result<(ResourceId, IpAddr, IpAddr), AnyError>
+) -> Result<(ResourceId, IpAddr, IpAddr), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -271,7 +269,9 @@ where
   {
     let mut s = state.borrow_mut();
     let permissions = s.borrow_mut::<NP>();
-    permissions.check_net(&(&hostname, Some(0)), "Deno.startTls()")?;
+    permissions
+      .check_net(&(&hostname, Some(0)), "Deno.startTls()")
+      .map_err(NetError::Permission)?;
   }
 
   let ca_certs = args
@@ -281,7 +281,7 @@ where
     .collect::<Vec<_>>();
 
   let hostname_dns = ServerName::try_from(hostname.to_string())
-    .map_err(|_| invalid_hostname(&hostname))?;
+    .map_err(|_| NetError::InvalidHostname(hostname))?;
 
   let unsafely_ignore_certificate_errors = state
     .borrow()
@@ -291,19 +291,21 @@ where
   let root_cert_store = state
     .borrow()
     .borrow::<DefaultTlsOptions>()
-    .root_cert_store()?;
+    .root_cert_store()
+    .map_err(NetError::RootCertStore)?;
 
   let resource_rc = state
     .borrow_mut()
     .resource_table
-    .take::<TcpStreamResource>(rid)?;
+    .take::<TcpStreamResource>(rid)
+    .map_err(NetError::Resource)?;
   // This TCP connection might be used somewhere else. If it's the case, we cannot proceed with the
   // process of starting a TLS connection on top of this TCP connection, so we just return a Busy error.
   // See also: https://github.com/denoland/deno/pull/16242
-  let resource = Rc::try_unwrap(resource_rc)
-    .map_err(|_| custom_error("Busy", "TCP stream is currently in use"))?;
+  let resource =
+    Rc::try_unwrap(resource_rc).map_err(|_| NetError::TcpStreamBusy)?;
   let (read_half, write_half) = resource.into_inner();
-  let tcp_stream = read_half.reunite(write_half)?;
+  let tcp_stream = read_half.reunite(write_half).map_err(NetError::Reunite)?;
 
   let local_addr = tcp_stream.local_addr()?;
   let remote_addr = tcp_stream.peer_addr()?;
@@ -345,7 +347,7 @@ pub async fn op_net_connect_tls<NP>(
   #[serde] addr: IpAddr,
   #[serde] args: ConnectTlsArgs,
   #[cppgc] key_pair: &TlsKeysHolder,
-) -> Result<(ResourceId, IpAddr, IpAddr), AnyError>
+) -> Result<(ResourceId, IpAddr, IpAddr), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -359,9 +361,14 @@ where
     let mut s = state.borrow_mut();
     let permissions = s.borrow_mut::<NP>();
     permissions
-      .check_net(&(&addr.hostname, Some(addr.port)), "Deno.connectTls()")?;
+      .check_net(&(&addr.hostname, Some(addr.port)), "Deno.connectTls()")
+      .map_err(NetError::Permission)?;
     if let Some(path) = cert_file {
-      Some(permissions.check_read(path, "Deno.connectTls()")?)
+      Some(
+        permissions
+          .check_read(path, "Deno.connectTls()")
+          .map_err(NetError::Permission)?,
+      )
     } else {
       None
     }
@@ -382,17 +389,18 @@ where
   let root_cert_store = state
     .borrow()
     .borrow::<DefaultTlsOptions>()
-    .root_cert_store()?;
+    .root_cert_store()
+    .map_err(NetError::RootCertStore)?;
   let hostname_dns = if let Some(server_name) = args.server_name {
     ServerName::try_from(server_name)
   } else {
     ServerName::try_from(addr.hostname.clone())
   }
-  .map_err(|_| invalid_hostname(&addr.hostname))?;
+  .map_err(|_| NetError::InvalidHostname(addr.hostname.clone()))?;
   let connect_addr = resolve_addr(&addr.hostname, addr.port)
     .await?
     .next()
-    .ok_or_else(|| generic_error("No resolved address found"))?;
+    .ok_or_else(|| NetError::NoResolvedAddress)?;
   let tcp_stream = TcpStream::connect(connect_addr).await?;
   let local_addr = tcp_stream.local_addr()?;
   let remote_addr = tcp_stream.peer_addr()?;
@@ -444,7 +452,7 @@ pub fn op_net_listen_tls<NP>(
   #[serde] addr: IpAddr,
   #[serde] args: ListenTlsArgs,
   #[cppgc] keys: &TlsKeysHolder,
-) -> Result<(ResourceId, IpAddr), AnyError>
+) -> Result<(ResourceId, IpAddr), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -455,12 +463,13 @@ where
   {
     let permissions = state.borrow_mut::<NP>();
     permissions
-      .check_net(&(&addr.hostname, Some(addr.port)), "Deno.listenTls()")?;
+      .check_net(&(&addr.hostname, Some(addr.port)), "Deno.listenTls()")
+      .map_err(NetError::Permission)?;
   }
 
   let bind_addr = resolve_addr_sync(&addr.hostname, addr.port)?
     .next()
-    .ok_or_else(|| generic_error("No resolved address found"))?;
+    .ok_or(NetError::NoResolvedAddress)?;
 
   let tcp_listener = if args.load_balanced {
     TcpListener::bind_load_balanced(bind_addr)
@@ -475,28 +484,24 @@ where
     .map(|s| s.into_bytes())
     .collect();
   let listener = match keys.take() {
-    TlsKeys::Null => Err(anyhow!("Deno.listenTls requires a key")),
+    TlsKeys::Null => return Err(NetError::ListenTlsRequiresKey),
     TlsKeys::Static(TlsKey(cert, key)) => {
       let mut tls_config = ServerConfig::builder()
         .with_no_client_auth()
-        .with_single_cert(cert, key)
-        .map_err(|e| anyhow!(e))?;
+        .with_single_cert(cert, key)?;
       tls_config.alpn_protocols = alpn;
-      Ok(TlsListener {
+      TlsListener {
         tcp_listener,
         tls_config: Some(tls_config.into()),
         server_config_provider: None,
-      })
+      }
     }
-    TlsKeys::Resolver(resolver) => Ok(TlsListener {
+    TlsKeys::Resolver(resolver) => TlsListener {
       tcp_listener,
       tls_config: None,
       server_config_provider: Some(resolver.into_server_config_provider(alpn)),
-    }),
-  }
-  .map_err(|e| {
-    custom_error("InvalidData", "Error creating TLS certificate").context(e)
-  })?;
+    },
+  };
 
   let tls_listener_resource = NetworkListenerResource::new(listener);
 
@@ -510,23 +515,23 @@ where
 pub async fn op_net_accept_tls(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(ResourceId, IpAddr, IpAddr), AnyError> {
+) -> Result<(ResourceId, IpAddr, IpAddr), NetError> {
   let resource = state
     .borrow()
     .resource_table
     .get::<NetworkListenerResource<TlsListener>>(rid)
-    .map_err(|_| bad_resource("Listener has been closed"))?;
+    .map_err(|_| NetError::ListenerClosed)?;
 
   let cancel_handle = RcRef::map(&resource, |r| &r.cancel);
   let listener = RcRef::map(&resource, |r| &r.listener)
     .try_borrow_mut()
-    .ok_or_else(|| custom_error("Busy", "Another accept task is ongoing"))?;
+    .ok_or_else(|| NetError::AcceptTaskOngoing)?;
 
   let (tls_stream, remote_addr) =
     match listener.accept().try_or_cancel(&cancel_handle).await {
       Ok(tuple) => tuple,
       Err(err) if err.kind() == ErrorKind::Interrupted => {
-        return Err(bad_resource("Listener has been closed"));
+        return Err(NetError::ListenerClosed);
       }
       Err(err) => return Err(err.into()),
     };
@@ -547,11 +552,11 @@ pub async fn op_net_accept_tls(
 pub async fn op_tls_handshake(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<TlsHandshakeInfo, AnyError> {
+) -> Result<TlsHandshakeInfo, NetError> {
   let resource = state
     .borrow()
     .resource_table
     .get::<TlsStreamResource>(rid)
-    .map_err(|_| bad_resource("Listener has been closed"))?;
-  resource.handshake().await
+    .map_err(|_| NetError::ListenerClosed)?;
+  resource.handshake().await.map_err(Into::into)
 }
diff --git a/ext/net/ops_unix.rs b/ext/net/ops_unix.rs
index 95293284f0..04ae84906f 100644
--- a/ext/net/ops_unix.rs
+++ b/ext/net/ops_unix.rs
@@ -1,11 +1,9 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 use crate::io::UnixStreamResource;
+use crate::ops::NetError;
 use crate::raw::NetworkListenerResource;
 use crate::NetPermissions;
-use deno_core::error::bad_resource;
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::AsyncRefCell;
 use deno_core::CancelHandle;
@@ -26,11 +24,8 @@ use tokio::net::UnixListener;
 pub use tokio::net::UnixStream;
 
 /// A utility function to map OsStrings to Strings
-pub fn into_string(s: std::ffi::OsString) -> Result<String, AnyError> {
-  s.into_string().map_err(|s| {
-    let message = format!("File name or path {s:?} is not valid UTF-8");
-    custom_error("InvalidData", message)
-  })
+pub fn into_string(s: std::ffi::OsString) -> Result<String, NetError> {
+  s.into_string().map_err(NetError::InvalidUtf8)
 }
 
 pub struct UnixDatagramResource {
@@ -63,15 +58,15 @@ pub struct UnixListenArgs {
 pub async fn op_net_accept_unix(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(ResourceId, Option<String>, Option<String>), AnyError> {
+) -> Result<(ResourceId, Option<String>, Option<String>), NetError> {
   let resource = state
     .borrow()
     .resource_table
     .get::<NetworkListenerResource<UnixListener>>(rid)
-    .map_err(|_| bad_resource("Listener has been closed"))?;
+    .map_err(|_| NetError::ListenerClosed)?;
   let listener = RcRef::map(&resource, |r| &r.listener)
     .try_borrow_mut()
-    .ok_or_else(|| custom_error("Busy", "Listener already in use"))?;
+    .ok_or(NetError::ListenerBusy)?;
   let cancel = RcRef::map(resource, |r| &r.cancel);
   let (unix_stream, _socket_addr) = listener
     .accept()
@@ -95,7 +90,7 @@ pub async fn op_net_accept_unix(
 pub async fn op_net_connect_unix<NP>(
   state: Rc<RefCell<OpState>>,
   #[string] address_path: String,
-) -> Result<(ResourceId, Option<String>, Option<String>), AnyError>
+) -> Result<(ResourceId, Option<String>, Option<String>), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -103,10 +98,12 @@ where
     let mut state_ = state.borrow_mut();
     let address_path = state_
       .borrow_mut::<NP>()
-      .check_read(&address_path, "Deno.connect()")?;
+      .check_read(&address_path, "Deno.connect()")
+      .map_err(NetError::Permission)?;
     _ = state_
       .borrow_mut::<NP>()
-      .check_write_path(&address_path, "Deno.connect()")?;
+      .check_write_path(&address_path, "Deno.connect()")
+      .map_err(NetError::Permission)?;
     address_path
   };
   let unix_stream = UnixStream::connect(&address_path).await?;
@@ -127,15 +124,15 @@ pub async fn op_net_recv_unixpacket(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[buffer] mut buf: JsBuffer,
-) -> Result<(usize, Option<String>), AnyError> {
+) -> Result<(usize, Option<String>), NetError> {
   let resource = state
     .borrow()
     .resource_table
     .get::<UnixDatagramResource>(rid)
-    .map_err(|_| bad_resource("Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosed)?;
   let socket = RcRef::map(&resource, |r| &r.socket)
     .try_borrow_mut()
-    .ok_or_else(|| custom_error("Busy", "Socket already in use"))?;
+    .ok_or(NetError::SocketBusy)?;
   let cancel = RcRef::map(resource, |r| &r.cancel);
   let (nread, remote_addr) =
     socket.recv_from(&mut buf).try_or_cancel(cancel).await?;
@@ -150,24 +147,25 @@ pub async fn op_net_send_unixpacket<NP>(
   #[smi] rid: ResourceId,
   #[string] address_path: String,
   #[buffer] zero_copy: JsBuffer,
-) -> Result<usize, AnyError>
+) -> Result<usize, NetError>
 where
   NP: NetPermissions + 'static,
 {
   let address_path = {
     let mut s = state.borrow_mut();
     s.borrow_mut::<NP>()
-      .check_write(&address_path, "Deno.DatagramConn.send()")?
+      .check_write(&address_path, "Deno.DatagramConn.send()")
+      .map_err(NetError::Permission)?
   };
 
   let resource = state
     .borrow()
     .resource_table
     .get::<UnixDatagramResource>(rid)
-    .map_err(|_| custom_error("NotConnected", "Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosedNotConnected)?;
   let socket = RcRef::map(&resource, |r| &r.socket)
     .try_borrow_mut()
-    .ok_or_else(|| custom_error("Busy", "Socket already in use"))?;
+    .ok_or(NetError::SocketBusy)?;
   let nwritten = socket.send_to(&zero_copy, address_path).await?;
 
   Ok(nwritten)
@@ -179,14 +177,18 @@ pub fn op_net_listen_unix<NP>(
   state: &mut OpState,
   #[string] address_path: String,
   #[string] api_name: String,
-) -> Result<(ResourceId, Option<String>), AnyError>
+) -> Result<(ResourceId, Option<String>), NetError>
 where
   NP: NetPermissions + 'static,
 {
   let permissions = state.borrow_mut::<NP>();
   let api_call_expr = format!("{}()", api_name);
-  let address_path = permissions.check_read(&address_path, &api_call_expr)?;
-  _ = permissions.check_write_path(&address_path, &api_call_expr)?;
+  let address_path = permissions
+    .check_read(&address_path, &api_call_expr)
+    .map_err(NetError::Permission)?;
+  _ = permissions
+    .check_write_path(&address_path, &api_call_expr)
+    .map_err(NetError::Permission)?;
   let listener = UnixListener::bind(address_path)?;
   let local_addr = listener.local_addr()?;
   let pathname = local_addr.as_pathname().map(pathstring).transpose()?;
@@ -198,14 +200,17 @@ where
 pub fn net_listen_unixpacket<NP>(
   state: &mut OpState,
   address_path: String,
-) -> Result<(ResourceId, Option<String>), AnyError>
+) -> Result<(ResourceId, Option<String>), NetError>
 where
   NP: NetPermissions + 'static,
 {
   let permissions = state.borrow_mut::<NP>();
-  let address_path =
-    permissions.check_read(&address_path, "Deno.listenDatagram()")?;
-  _ = permissions.check_write_path(&address_path, "Deno.listenDatagram()")?;
+  let address_path = permissions
+    .check_read(&address_path, "Deno.listenDatagram()")
+    .map_err(NetError::Permission)?;
+  _ = permissions
+    .check_write_path(&address_path, "Deno.listenDatagram()")
+    .map_err(NetError::Permission)?;
   let socket = UnixDatagram::bind(address_path)?;
   let local_addr = socket.local_addr()?;
   let pathname = local_addr.as_pathname().map(pathstring).transpose()?;
@@ -222,7 +227,7 @@ where
 pub fn op_net_listen_unixpacket<NP>(
   state: &mut OpState,
   #[string] path: String,
-) -> Result<(ResourceId, Option<String>), AnyError>
+) -> Result<(ResourceId, Option<String>), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -235,13 +240,13 @@ where
 pub fn op_node_unstable_net_listen_unixpacket<NP>(
   state: &mut OpState,
   #[string] path: String,
-) -> Result<(ResourceId, Option<String>), AnyError>
+) -> Result<(ResourceId, Option<String>), NetError>
 where
   NP: NetPermissions + 'static,
 {
   net_listen_unixpacket::<NP>(state, path)
 }
 
-pub fn pathstring(pathname: &Path) -> Result<String, AnyError> {
+pub fn pathstring(pathname: &Path) -> Result<String, NetError> {
   into_string(pathname.into())
 }
diff --git a/ext/net/resolve_addr.rs b/ext/net/resolve_addr.rs
index 8bbdd5192c..3a97081eac 100644
--- a/ext/net/resolve_addr.rs
+++ b/ext/net/resolve_addr.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use std::net::SocketAddr;
 use std::net::ToSocketAddrs;
 use tokio::net::lookup_host;
@@ -9,7 +8,7 @@ use tokio::net::lookup_host;
 pub async fn resolve_addr(
   hostname: &str,
   port: u16,
-) -> Result<impl Iterator<Item = SocketAddr> + '_, AnyError> {
+) -> Result<impl Iterator<Item = SocketAddr> + '_, std::io::Error> {
   let addr_port_pair = make_addr_port_pair(hostname, port);
   let result = lookup_host(addr_port_pair).await?;
   Ok(result)
@@ -19,7 +18,7 @@ pub async fn resolve_addr(
 pub fn resolve_addr_sync(
   hostname: &str,
   port: u16,
-) -> Result<impl Iterator<Item = SocketAddr>, AnyError> {
+) -> Result<impl Iterator<Item = SocketAddr>, std::io::Error> {
   let addr_port_pair = make_addr_port_pair(hostname, port);
   let result = addr_port_pair.to_socket_addrs()?;
   Ok(result)
diff --git a/ext/node/Cargo.toml b/ext/node/Cargo.toml
index 17da17cd81..9e1a3495b5 100644
--- a/ext/node/Cargo.toml
+++ b/ext/node/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_node"
-version = "0.105.0"
+version = "0.114.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -34,6 +34,7 @@ deno_io.workspace = true
 deno_media_type.workspace = true
 deno_net.workspace = true
 deno_package_json.workspace = true
+deno_path_util.workspace = true
 deno_permissions.workspace = true
 deno_whoami = "0.1.0"
 der = { version = "0.7.9", features = ["derive"] }
diff --git a/ext/node/lib.rs b/ext/node/lib.rs
index 0c821ecf8b..84f39552c1 100644
--- a/ext/node/lib.rs
+++ b/ext/node/lib.rs
@@ -9,25 +9,23 @@ use std::path::Path;
 use std::path::PathBuf;
 
 use deno_core::error::AnyError;
-use deno_core::located_script_name;
 use deno_core::op2;
 use deno_core::url::Url;
 #[allow(unused_imports)]
 use deno_core::v8;
 use deno_core::v8::ExternalReference;
-use deno_core::JsRuntime;
-use deno_fs::sync::MaybeSend;
-use deno_fs::sync::MaybeSync;
-use node_resolver::NpmResolverRc;
+use node_resolver::errors::ClosestPkgJsonError;
+use node_resolver::NpmPackageFolderResolverRc;
 use once_cell::sync::Lazy;
 
 extern crate libz_sys as zlib;
 
 mod global;
-mod ops;
+pub mod ops;
 mod polyfill;
 
 pub use deno_package_json::PackageJson;
+use deno_permissions::PermissionCheckError;
 pub use node_resolver::PathClean;
 pub use ops::ipc::ChildPipeFd;
 pub use ops::ipc::IpcJsonStreamResource;
@@ -49,10 +47,18 @@ pub trait NodePermissions {
     &mut self,
     url: &Url,
     api_name: &str,
-  ) -> Result<(), AnyError>;
+  ) -> Result<(), PermissionCheckError>;
+  fn check_net(
+    &mut self,
+    host: (&str, Option<u16>),
+    api_name: &str,
+  ) -> Result<(), PermissionCheckError>;
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
   #[inline(always)]
-  fn check_read(&mut self, path: &str) -> Result<PathBuf, AnyError> {
+  fn check_read(
+    &mut self,
+    path: &str,
+  ) -> Result<PathBuf, PermissionCheckError> {
     self.check_read_with_api_name(path, None)
   }
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
@@ -60,19 +66,24 @@ pub trait NodePermissions {
     &mut self,
     path: &str,
     api_name: Option<&str>,
-  ) -> Result<PathBuf, AnyError>;
+  ) -> Result<PathBuf, PermissionCheckError>;
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
   fn check_read_path<'a>(
     &mut self,
     path: &'a Path,
-  ) -> Result<Cow<'a, Path>, AnyError>;
-  fn check_sys(&mut self, kind: &str, api_name: &str) -> Result<(), AnyError>;
+  ) -> Result<Cow<'a, Path>, PermissionCheckError>;
+  fn query_read_all(&mut self) -> bool;
+  fn check_sys(
+    &mut self,
+    kind: &str,
+    api_name: &str,
+  ) -> Result<(), PermissionCheckError>;
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
   fn check_write_with_api_name(
     &mut self,
     path: &str,
     api_name: Option<&str>,
-  ) -> Result<PathBuf, AnyError>;
+  ) -> Result<PathBuf, PermissionCheckError>;
 }
 
 impl NodePermissions for deno_permissions::PermissionsContainer {
@@ -81,16 +92,24 @@ impl NodePermissions for deno_permissions::PermissionsContainer {
     &mut self,
     url: &Url,
     api_name: &str,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_net_url(self, url, api_name)
   }
 
+  fn check_net(
+    &mut self,
+    host: (&str, Option<u16>),
+    api_name: &str,
+  ) -> Result<(), PermissionCheckError> {
+    deno_permissions::PermissionsContainer::check_net(self, &host, api_name)
+  }
+
   #[inline(always)]
   fn check_read_with_api_name(
     &mut self,
     path: &str,
     api_name: Option<&str>,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_read_with_api_name(
       self, path, api_name,
     )
@@ -99,36 +118,50 @@ impl NodePermissions for deno_permissions::PermissionsContainer {
   fn check_read_path<'a>(
     &mut self,
     path: &'a Path,
-  ) -> Result<Cow<'a, Path>, AnyError> {
+  ) -> Result<Cow<'a, Path>, PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_read_path(self, path, None)
   }
 
+  fn query_read_all(&mut self) -> bool {
+    deno_permissions::PermissionsContainer::query_read_all(self)
+  }
+
   #[inline(always)]
   fn check_write_with_api_name(
     &mut self,
     path: &str,
     api_name: Option<&str>,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_write_with_api_name(
       self, path, api_name,
     )
   }
 
-  fn check_sys(&mut self, kind: &str, api_name: &str) -> Result<(), AnyError> {
+  fn check_sys(
+    &mut self,
+    kind: &str,
+    api_name: &str,
+  ) -> Result<(), PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_sys(self, kind, api_name)
   }
 }
 
 #[allow(clippy::disallowed_types)]
-pub type NodeRequireResolverRc =
-  deno_fs::sync::MaybeArc<dyn NodeRequireResolver>;
+pub type NodeRequireLoaderRc = std::rc::Rc<dyn NodeRequireLoader>;
 
-pub trait NodeRequireResolver: std::fmt::Debug + MaybeSend + MaybeSync {
-  fn ensure_read_permission(
+pub trait NodeRequireLoader {
+  #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
+  fn ensure_read_permission<'a>(
     &self,
     permissions: &mut dyn NodePermissions,
-    path: &Path,
-  ) -> Result<(), AnyError>;
+    path: &'a Path,
+  ) -> Result<Cow<'a, Path>, AnyError>;
+
+  fn load_text_file_lossy(&self, path: &Path) -> Result<String, AnyError>;
+
+  /// Get if the module kind is maybe CJS and loading should determine
+  /// if its CJS or ESM.
+  fn is_maybe_cjs(&self, specifier: &Url) -> Result<bool, ClosestPkgJsonError>;
 }
 
 pub static NODE_ENV_VAR_ALLOWLIST: Lazy<HashSet<String>> = Lazy::new(|| {
@@ -146,10 +179,12 @@ fn op_node_build_os() -> String {
   env!("TARGET").split('-').nth(2).unwrap().to_string()
 }
 
+#[derive(Clone)]
 pub struct NodeExtInitServices {
-  pub node_require_resolver: NodeRequireResolverRc,
+  pub node_require_loader: NodeRequireLoaderRc,
   pub node_resolver: NodeResolverRc,
-  pub npm_resolver: NpmResolverRc,
+  pub npm_resolver: NpmPackageFolderResolverRc,
+  pub pkg_json_resolver: PackageJsonResolverRc,
 }
 
 deno_core::extension!(deno_node,
@@ -167,6 +202,7 @@ deno_core::extension!(deno_node,
 
     ops::buffer::op_is_ascii,
     ops::buffer::op_is_utf8,
+    ops::buffer::op_transcode,
     ops::crypto::op_node_check_prime_async,
     ops::crypto::op_node_check_prime_bytes_async,
     ops::crypto::op_node_check_prime_bytes,
@@ -314,6 +350,7 @@ deno_core::extension!(deno_node,
     ops::zlib::op_zlib_write,
     ops::zlib::op_zlib_init,
     ops::zlib::op_zlib_reset,
+    ops::zlib::op_zlib_crc32,
     ops::zlib::brotli::op_brotli_compress,
     ops::zlib::brotli::op_brotli_compress_async,
     ops::zlib::brotli::op_create_brotli_compress,
@@ -341,7 +378,7 @@ deno_core::extension!(deno_node,
     ops::http2::op_http2_send_response,
     ops::os::op_node_os_get_priority<P>,
     ops::os::op_node_os_set_priority<P>,
-    ops::os::op_node_os_username<P>,
+    ops::os::op_node_os_user_info<P>,
     ops::os::op_geteuid<P>,
     ops::os::op_getegid<P>,
     ops::os::op_cpus<P>,
@@ -353,6 +390,7 @@ deno_core::extension!(deno_node,
     ops::require::op_require_proxy_path,
     ops::require::op_require_is_deno_dir_package,
     ops::require::op_require_resolve_deno_dir,
+    ops::require::op_require_is_maybe_cjs,
     ops::require::op_require_is_request_relative,
     ops::require::op_require_resolve_lookup_paths,
     ops::require::op_require_try_self_parent_path<P>,
@@ -366,7 +404,6 @@ deno_core::extension!(deno_node,
     ops::require::op_require_read_file<P>,
     ops::require::op_require_as_file_path,
     ops::require::op_require_resolve_exports<P>,
-    ops::require::op_require_read_closest_package_json<P>,
     ops::require::op_require_read_package_scope<P>,
     ops::require::op_require_package_imports_resolve<P>,
     ops::require::op_require_break_on_next_statement,
@@ -380,6 +417,15 @@ deno_core::extension!(deno_node,
     ops::process::op_node_process_kill,
     ops::process::op_process_abort,
     ops::tls::op_get_root_certificates,
+    ops::inspector::op_inspector_open<P>,
+    ops::inspector::op_inspector_close,
+    ops::inspector::op_inspector_url,
+    ops::inspector::op_inspector_wait,
+    ops::inspector::op_inspector_connect<P>,
+    ops::inspector::op_inspector_dispatch,
+    ops::inspector::op_inspector_disconnect,
+    ops::inspector::op_inspector_emit_protocol_event,
+    ops::inspector::op_inspector_enabled,
   ],
   esm_entry_point = "ext:deno_node/02_init.js",
   esm = [
@@ -462,6 +508,7 @@ deno_core::extension!(deno_node,
     "internal_binding/constants.ts",
     "internal_binding/crypto.ts",
     "internal_binding/handle_wrap.ts",
+    "internal_binding/http_parser.ts",
     "internal_binding/mod.ts",
     "internal_binding/node_file.ts",
     "internal_binding/node_options.ts",
@@ -587,8 +634,8 @@ deno_core::extension!(deno_node,
     "node:http" = "http.ts",
     "node:http2" = "http2.ts",
     "node:https" = "https.ts",
-    "node:inspector" = "inspector.ts",
-    "node:inspector/promises" = "inspector.ts",
+    "node:inspector" = "inspector.js",
+    "node:inspector/promises" = "inspector/promises.js",
     "node:module" = "01_require.js",
     "node:net" = "net.ts",
     "node:os" = "os.ts",
@@ -631,9 +678,10 @@ deno_core::extension!(deno_node,
     state.put(options.fs.clone());
 
     if let Some(init) = &options.maybe_init {
-      state.put(init.node_require_resolver.clone());
+      state.put(init.node_require_loader.clone());
       state.put(init.node_resolver.clone());
       state.put(init.npm_resolver.clone());
+      state.put(init.pkg_json_resolver.clone());
     }
   },
   global_template_middleware = global_template_middleware,
@@ -753,33 +801,16 @@ deno_core::extension!(deno_node,
   },
 );
 
-pub fn load_cjs_module(
-  js_runtime: &mut JsRuntime,
-  module: &str,
-  main: bool,
-  inspect_brk: bool,
-) -> Result<(), AnyError> {
-  fn escape_for_single_quote_string(text: &str) -> String {
-    text.replace('\\', r"\\").replace('\'', r"\'")
-  }
-
-  let source_code = format!(
-    r#"(function loadCjsModule(moduleName, isMain, inspectBrk) {{
-      Deno[Deno.internal].node.loadCjsModule(moduleName, isMain, inspectBrk);
-    }})('{module}', {main}, {inspect_brk});"#,
-    main = main,
-    module = escape_for_single_quote_string(module),
-    inspect_brk = inspect_brk,
-  );
-
-  js_runtime.execute_script(located_script_name!(), source_code)?;
-  Ok(())
-}
-
 pub type NodeResolver = node_resolver::NodeResolver<DenoFsNodeResolverEnv>;
 #[allow(clippy::disallowed_types)]
 pub type NodeResolverRc =
   deno_fs::sync::MaybeArc<node_resolver::NodeResolver<DenoFsNodeResolverEnv>>;
+pub type PackageJsonResolver =
+  node_resolver::PackageJsonResolver<DenoFsNodeResolverEnv>;
+#[allow(clippy::disallowed_types)]
+pub type PackageJsonResolverRc = deno_fs::sync::MaybeArc<
+  node_resolver::PackageJsonResolver<DenoFsNodeResolverEnv>,
+>;
 
 #[derive(Debug)]
 pub struct DenoFsNodeResolverEnv {
diff --git a/ext/node/ops/blocklist.rs b/ext/node/ops/blocklist.rs
index 332cdda8f9..6c64d68eca 100644
--- a/ext/node/ops/blocklist.rs
+++ b/ext/node/ops/blocklist.rs
@@ -7,9 +7,6 @@ use std::net::Ipv4Addr;
 use std::net::Ipv6Addr;
 use std::net::SocketAddr;
 
-use deno_core::anyhow::anyhow;
-use deno_core::anyhow::bail;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 
@@ -27,13 +24,25 @@ impl deno_core::GarbageCollected for BlockListResource {}
 #[derive(Serialize)]
 struct SocketAddressSerialization(String, String);
 
+#[derive(Debug, thiserror::Error)]
+pub enum BlocklistError {
+  #[error("{0}")]
+  AddrParse(#[from] std::net::AddrParseError),
+  #[error("{0}")]
+  IpNetwork(#[from] ipnetwork::IpNetworkError),
+  #[error("Invalid address")]
+  InvalidAddress,
+  #[error("IP version mismatch between start and end addresses")]
+  IpVersionMismatch,
+}
+
 #[op2(fast)]
 pub fn op_socket_address_parse(
   state: &mut OpState,
   #[string] addr: &str,
   #[smi] port: u16,
   #[string] family: &str,
-) -> Result<bool, AnyError> {
+) -> Result<bool, BlocklistError> {
   let ip = addr.parse::<IpAddr>()?;
   let parsed: SocketAddr = SocketAddr::new(ip, port);
   let parsed_ip_str = parsed.ip().to_string();
@@ -52,7 +61,7 @@ pub fn op_socket_address_parse(
       Ok(false)
     }
   } else {
-    Err(anyhow!("Invalid address"))
+    Err(BlocklistError::InvalidAddress)
   }
 }
 
@@ -60,8 +69,8 @@ pub fn op_socket_address_parse(
 #[serde]
 pub fn op_socket_address_get_serialization(
   state: &mut OpState,
-) -> Result<SocketAddressSerialization, AnyError> {
-  Ok(state.take::<SocketAddressSerialization>())
+) -> SocketAddressSerialization {
+  state.take::<SocketAddressSerialization>()
 }
 
 #[op2]
@@ -77,7 +86,7 @@ pub fn op_blocklist_new() -> BlockListResource {
 pub fn op_blocklist_add_address(
   #[cppgc] wrap: &BlockListResource,
   #[string] addr: &str,
-) -> Result<(), AnyError> {
+) -> Result<(), BlocklistError> {
   wrap.blocklist.borrow_mut().add_address(addr)
 }
 
@@ -86,7 +95,7 @@ pub fn op_blocklist_add_range(
   #[cppgc] wrap: &BlockListResource,
   #[string] start: &str,
   #[string] end: &str,
-) -> Result<bool, AnyError> {
+) -> Result<bool, BlocklistError> {
   wrap.blocklist.borrow_mut().add_range(start, end)
 }
 
@@ -95,7 +104,7 @@ pub fn op_blocklist_add_subnet(
   #[cppgc] wrap: &BlockListResource,
   #[string] addr: &str,
   #[smi] prefix: u8,
-) -> Result<(), AnyError> {
+) -> Result<(), BlocklistError> {
   wrap.blocklist.borrow_mut().add_subnet(addr, prefix)
 }
 
@@ -104,7 +113,7 @@ pub fn op_blocklist_check(
   #[cppgc] wrap: &BlockListResource,
   #[string] addr: &str,
   #[string] r#type: &str,
-) -> Result<bool, AnyError> {
+) -> Result<bool, BlocklistError> {
   wrap.blocklist.borrow().check(addr, r#type)
 }
 
@@ -123,7 +132,7 @@ impl BlockList {
     &mut self,
     addr: IpAddr,
     prefix: Option<u8>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), BlocklistError> {
     match addr {
       IpAddr::V4(addr) => {
         let ipv4_prefix = prefix.unwrap_or(32);
@@ -154,7 +163,7 @@ impl BlockList {
     Ok(())
   }
 
-  pub fn add_address(&mut self, address: &str) -> Result<(), AnyError> {
+  pub fn add_address(&mut self, address: &str) -> Result<(), BlocklistError> {
     let ip: IpAddr = address.parse()?;
     self.map_addr_add_network(ip, None)?;
     Ok(())
@@ -164,7 +173,7 @@ impl BlockList {
     &mut self,
     start: &str,
     end: &str,
-  ) -> Result<bool, AnyError> {
+  ) -> Result<bool, BlocklistError> {
     let start_ip: IpAddr = start.parse()?;
     let end_ip: IpAddr = end.parse()?;
 
@@ -193,25 +202,33 @@ impl BlockList {
           self.map_addr_add_network(IpAddr::V6(addr), None)?;
         }
       }
-      _ => bail!("IP version mismatch between start and end addresses"),
+      _ => return Err(BlocklistError::IpVersionMismatch),
     }
     Ok(true)
   }
 
-  pub fn add_subnet(&mut self, addr: &str, prefix: u8) -> Result<(), AnyError> {
+  pub fn add_subnet(
+    &mut self,
+    addr: &str,
+    prefix: u8,
+  ) -> Result<(), BlocklistError> {
     let ip: IpAddr = addr.parse()?;
     self.map_addr_add_network(ip, Some(prefix))?;
     Ok(())
   }
 
-  pub fn check(&self, addr: &str, r#type: &str) -> Result<bool, AnyError> {
+  pub fn check(
+    &self,
+    addr: &str,
+    r#type: &str,
+  ) -> Result<bool, BlocklistError> {
     let addr: IpAddr = addr.parse()?;
     let family = r#type.to_lowercase();
     if family == "ipv4" && addr.is_ipv4() || family == "ipv6" && addr.is_ipv6()
     {
       Ok(self.rules.iter().any(|net| net.contains(addr)))
     } else {
-      Err(anyhow!("Invalid address"))
+      Err(BlocklistError::InvalidAddress)
     }
   }
 }
diff --git a/ext/node/ops/buffer.rs b/ext/node/ops/buffer.rs
index 74a011ab80..01f878ec15 100644
--- a/ext/node/ops/buffer.rs
+++ b/ext/node/ops/buffer.rs
@@ -1,5 +1,7 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
+use deno_core::anyhow::anyhow;
+use deno_core::anyhow::Result;
 use deno_core::op2;
 
 #[op2(fast)]
@@ -11,3 +13,107 @@ pub fn op_is_ascii(#[buffer] buf: &[u8]) -> bool {
 pub fn op_is_utf8(#[buffer] buf: &[u8]) -> bool {
   std::str::from_utf8(buf).is_ok()
 }
+
+#[op2]
+#[buffer]
+pub fn op_transcode(
+  #[buffer] source: &[u8],
+  #[string] from_encoding: &str,
+  #[string] to_encoding: &str,
+) -> Result<Vec<u8>> {
+  match (from_encoding, to_encoding) {
+    ("utf8", "ascii") => Ok(utf8_to_ascii(source)),
+    ("utf8", "latin1") => Ok(utf8_to_latin1(source)),
+    ("utf8", "utf16le") => utf8_to_utf16le(source),
+    ("utf16le", "utf8") => utf16le_to_utf8(source),
+    ("latin1", "utf16le") | ("ascii", "utf16le") => {
+      Ok(latin1_ascii_to_utf16le(source))
+    }
+    (from, to) => Err(anyhow!("Unable to transcode Buffer {from}->{to}")),
+  }
+}
+
+fn latin1_ascii_to_utf16le(source: &[u8]) -> Vec<u8> {
+  let mut result = Vec::with_capacity(source.len() * 2);
+  for &byte in source {
+    result.push(byte);
+    result.push(0);
+  }
+  result
+}
+
+fn utf16le_to_utf8(source: &[u8]) -> Result<Vec<u8>> {
+  let ucs2_vec: Vec<u16> = source
+    .chunks(2)
+    .map(|chunk| u16::from_le_bytes([chunk[0], chunk[1]]))
+    .collect();
+  String::from_utf16(&ucs2_vec)
+    .map(|utf8_string| utf8_string.into_bytes())
+    .map_err(|e| anyhow!("Invalid UTF-16 sequence: {}", e))
+}
+
+fn utf8_to_utf16le(source: &[u8]) -> Result<Vec<u8>> {
+  let utf8_string = std::str::from_utf8(source)?;
+  let ucs2_vec: Vec<u16> = utf8_string.encode_utf16().collect();
+  let bytes: Vec<u8> = ucs2_vec.iter().flat_map(|&x| x.to_le_bytes()).collect();
+  Ok(bytes)
+}
+
+fn utf8_to_latin1(source: &[u8]) -> Vec<u8> {
+  let mut latin1_bytes = Vec::with_capacity(source.len());
+  let mut i = 0;
+  while i < source.len() {
+    match source[i] {
+      byte if byte <= 0x7F => {
+        // ASCII character
+        latin1_bytes.push(byte);
+        i += 1;
+      }
+      byte if (0xC2..=0xDF).contains(&byte) && i + 1 < source.len() => {
+        // 2-byte UTF-8 sequence
+        let codepoint =
+          ((byte as u16 & 0x1F) << 6) | (source[i + 1] as u16 & 0x3F);
+        latin1_bytes.push(if codepoint <= 0xFF {
+          codepoint as u8
+        } else {
+          b'?'
+        });
+        i += 2;
+      }
+      _ => {
+        // 3-byte or 4-byte UTF-8 sequence, or invalid UTF-8
+        latin1_bytes.push(b'?');
+        // Skip to the next valid UTF-8 start byte
+        i += 1;
+        while i < source.len() && (source[i] & 0xC0) == 0x80 {
+          i += 1;
+        }
+      }
+    }
+  }
+  latin1_bytes
+}
+
+fn utf8_to_ascii(source: &[u8]) -> Vec<u8> {
+  let mut ascii_bytes = Vec::with_capacity(source.len());
+  let mut i = 0;
+  while i < source.len() {
+    match source[i] {
+      byte if byte <= 0x7F => {
+        // ASCII character
+        ascii_bytes.push(byte);
+        i += 1;
+      }
+      _ => {
+        // Non-ASCII character
+        ascii_bytes.push(b'?');
+        // Skip to the next valid UTF-8 start byte
+        i += 1;
+        while i < source.len() && (source[i] & 0xC0) == 0x80 {
+          i += 1;
+        }
+      }
+    }
+  }
+  ascii_bytes
+}
diff --git a/ext/node/ops/crypto/cipher.rs b/ext/node/ops/crypto/cipher.rs
index b80aa33fe8..ec45146b49 100644
--- a/ext/node/ops/crypto/cipher.rs
+++ b/ext/node/ops/crypto/cipher.rs
@@ -4,9 +4,6 @@ use aes::cipher::block_padding::Pkcs7;
 use aes::cipher::BlockDecryptMut;
 use aes::cipher::BlockEncryptMut;
 use aes::cipher::KeyIvInit;
-use deno_core::error::range_error;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::Resource;
 use digest::generic_array::GenericArray;
 use digest::KeyInit;
@@ -50,8 +47,22 @@ pub struct DecipherContext {
   decipher: Rc<RefCell<Decipher>>,
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum CipherContextError {
+  #[error("Cipher context is already in use")]
+  ContextInUse,
+  #[error("{0}")]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  Cipher(#[from] CipherError),
+}
+
 impl CipherContext {
-  pub fn new(algorithm: &str, key: &[u8], iv: &[u8]) -> Result<Self, AnyError> {
+  pub fn new(
+    algorithm: &str,
+    key: &[u8],
+    iv: &[u8],
+  ) -> Result<Self, CipherContextError> {
     Ok(Self {
       cipher: Rc::new(RefCell::new(Cipher::new(algorithm, key, iv)?)),
     })
@@ -74,16 +85,31 @@ impl CipherContext {
     auto_pad: bool,
     input: &[u8],
     output: &mut [u8],
-  ) -> Result<Tag, AnyError> {
+  ) -> Result<Tag, CipherContextError> {
     Rc::try_unwrap(self.cipher)
-      .map_err(|_| type_error("Cipher context is already in use"))?
+      .map_err(|_| CipherContextError::ContextInUse)?
       .into_inner()
       .r#final(auto_pad, input, output)
+      .map_err(Into::into)
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum DecipherContextError {
+  #[error("Decipher context is already in use")]
+  ContextInUse,
+  #[error("{0}")]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  Decipher(#[from] DecipherError),
+}
+
 impl DecipherContext {
-  pub fn new(algorithm: &str, key: &[u8], iv: &[u8]) -> Result<Self, AnyError> {
+  pub fn new(
+    algorithm: &str,
+    key: &[u8],
+    iv: &[u8],
+  ) -> Result<Self, DecipherContextError> {
     Ok(Self {
       decipher: Rc::new(RefCell::new(Decipher::new(algorithm, key, iv)?)),
     })
@@ -103,11 +129,12 @@ impl DecipherContext {
     input: &[u8],
     output: &mut [u8],
     auth_tag: &[u8],
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), DecipherContextError> {
     Rc::try_unwrap(self.decipher)
-      .map_err(|_| type_error("Decipher context is already in use"))?
+      .map_err(|_| DecipherContextError::ContextInUse)?
       .into_inner()
       .r#final(auto_pad, input, output, auth_tag)
+      .map_err(Into::into)
   }
 }
 
@@ -123,12 +150,26 @@ impl Resource for DecipherContext {
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum CipherError {
+  #[error("IV length must be 12 bytes")]
+  InvalidIvLength,
+  #[error("Invalid key length")]
+  InvalidKeyLength,
+  #[error("Invalid initialization vector")]
+  InvalidInitializationVector,
+  #[error("Cannot pad the input data")]
+  CannotPadInputData,
+  #[error("Unknown cipher {0}")]
+  UnknownCipher(String),
+}
+
 impl Cipher {
   fn new(
     algorithm_name: &str,
     key: &[u8],
     iv: &[u8],
-  ) -> Result<Self, AnyError> {
+  ) -> Result<Self, CipherError> {
     use Cipher::*;
     Ok(match algorithm_name {
       "aes-128-cbc" => {
@@ -139,7 +180,7 @@ impl Cipher {
       "aes-256-ecb" => Aes256Ecb(Box::new(ecb::Encryptor::new(key.into()))),
       "aes-128-gcm" => {
         if iv.len() != 12 {
-          return Err(type_error("IV length must be 12 bytes"));
+          return Err(CipherError::InvalidIvLength);
         }
 
         let cipher =
@@ -149,7 +190,7 @@ impl Cipher {
       }
       "aes-256-gcm" => {
         if iv.len() != 12 {
-          return Err(type_error("IV length must be 12 bytes"));
+          return Err(CipherError::InvalidIvLength);
         }
 
         let cipher =
@@ -159,15 +200,15 @@ impl Cipher {
       }
       "aes256" | "aes-256-cbc" => {
         if key.len() != 32 {
-          return Err(range_error("Invalid key length"));
+          return Err(CipherError::InvalidKeyLength);
         }
         if iv.len() != 16 {
-          return Err(type_error("Invalid initialization vector"));
+          return Err(CipherError::InvalidInitializationVector);
         }
 
         Aes256Cbc(Box::new(cbc::Encryptor::new(key.into(), iv.into())))
       }
-      _ => return Err(type_error(format!("Unknown cipher {algorithm_name}"))),
+      _ => return Err(CipherError::UnknownCipher(algorithm_name.to_string())),
     })
   }
 
@@ -235,14 +276,14 @@ impl Cipher {
     auto_pad: bool,
     input: &[u8],
     output: &mut [u8],
-  ) -> Result<Tag, AnyError> {
+  ) -> Result<Tag, CipherError> {
     assert!(input.len() < 16);
     use Cipher::*;
     match (self, auto_pad) {
       (Aes128Cbc(encryptor), true) => {
         let _ = (*encryptor)
           .encrypt_padded_b2b_mut::<Pkcs7>(input, output)
-          .map_err(|_| type_error("Cannot pad the input data"))?;
+          .map_err(|_| CipherError::CannotPadInputData)?;
         Ok(None)
       }
       (Aes128Cbc(mut encryptor), false) => {
@@ -255,7 +296,7 @@ impl Cipher {
       (Aes128Ecb(encryptor), true) => {
         let _ = (*encryptor)
           .encrypt_padded_b2b_mut::<Pkcs7>(input, output)
-          .map_err(|_| type_error("Cannot pad the input data"))?;
+          .map_err(|_| CipherError::CannotPadInputData)?;
         Ok(None)
       }
       (Aes128Ecb(mut encryptor), false) => {
@@ -268,7 +309,7 @@ impl Cipher {
       (Aes192Ecb(encryptor), true) => {
         let _ = (*encryptor)
           .encrypt_padded_b2b_mut::<Pkcs7>(input, output)
-          .map_err(|_| type_error("Cannot pad the input data"))?;
+          .map_err(|_| CipherError::CannotPadInputData)?;
         Ok(None)
       }
       (Aes192Ecb(mut encryptor), false) => {
@@ -281,7 +322,7 @@ impl Cipher {
       (Aes256Ecb(encryptor), true) => {
         let _ = (*encryptor)
           .encrypt_padded_b2b_mut::<Pkcs7>(input, output)
-          .map_err(|_| type_error("Cannot pad the input data"))?;
+          .map_err(|_| CipherError::CannotPadInputData)?;
         Ok(None)
       }
       (Aes256Ecb(mut encryptor), false) => {
@@ -296,7 +337,7 @@ impl Cipher {
       (Aes256Cbc(encryptor), true) => {
         let _ = (*encryptor)
           .encrypt_padded_b2b_mut::<Pkcs7>(input, output)
-          .map_err(|_| type_error("Cannot pad the input data"))?;
+          .map_err(|_| CipherError::CannotPadInputData)?;
         Ok(None)
       }
       (Aes256Cbc(mut encryptor), false) => {
@@ -319,12 +360,32 @@ impl Cipher {
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum DecipherError {
+  #[error("IV length must be 12 bytes")]
+  InvalidIvLength,
+  #[error("Invalid key length")]
+  InvalidKeyLength,
+  #[error("Invalid initialization vector")]
+  InvalidInitializationVector,
+  #[error("Cannot unpad the input data")]
+  CannotUnpadInputData,
+  #[error("Failed to authenticate data")]
+  DataAuthenticationFailed,
+  #[error("setAutoPadding(false) not supported for Aes128Gcm yet")]
+  SetAutoPaddingFalseAes128GcmUnsupported,
+  #[error("setAutoPadding(false) not supported for Aes256Gcm yet")]
+  SetAutoPaddingFalseAes256GcmUnsupported,
+  #[error("Unknown cipher {0}")]
+  UnknownCipher(String),
+}
+
 impl Decipher {
   fn new(
     algorithm_name: &str,
     key: &[u8],
     iv: &[u8],
-  ) -> Result<Self, AnyError> {
+  ) -> Result<Self, DecipherError> {
     use Decipher::*;
     Ok(match algorithm_name {
       "aes-128-cbc" => {
@@ -335,7 +396,7 @@ impl Decipher {
       "aes-256-ecb" => Aes256Ecb(Box::new(ecb::Decryptor::new(key.into()))),
       "aes-128-gcm" => {
         if iv.len() != 12 {
-          return Err(type_error("IV length must be 12 bytes"));
+          return Err(DecipherError::InvalidIvLength);
         }
 
         let decipher =
@@ -345,7 +406,7 @@ impl Decipher {
       }
       "aes-256-gcm" => {
         if iv.len() != 12 {
-          return Err(type_error("IV length must be 12 bytes"));
+          return Err(DecipherError::InvalidIvLength);
         }
 
         let decipher =
@@ -355,15 +416,17 @@ impl Decipher {
       }
       "aes256" | "aes-256-cbc" => {
         if key.len() != 32 {
-          return Err(range_error("Invalid key length"));
+          return Err(DecipherError::InvalidKeyLength);
         }
         if iv.len() != 16 {
-          return Err(type_error("Invalid initialization vector"));
+          return Err(DecipherError::InvalidInitializationVector);
         }
 
         Aes256Cbc(Box::new(cbc::Decryptor::new(key.into(), iv.into())))
       }
-      _ => return Err(type_error(format!("Unknown cipher {algorithm_name}"))),
+      _ => {
+        return Err(DecipherError::UnknownCipher(algorithm_name.to_string()))
+      }
     })
   }
 
@@ -432,14 +495,14 @@ impl Decipher {
     input: &[u8],
     output: &mut [u8],
     auth_tag: &[u8],
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), DecipherError> {
     use Decipher::*;
     match (self, auto_pad) {
       (Aes128Cbc(decryptor), true) => {
         assert!(input.len() == 16);
         let _ = (*decryptor)
           .decrypt_padded_b2b_mut::<Pkcs7>(input, output)
-          .map_err(|_| type_error("Cannot unpad the input data"))?;
+          .map_err(|_| DecipherError::CannotUnpadInputData)?;
         Ok(())
       }
       (Aes128Cbc(mut decryptor), false) => {
@@ -453,7 +516,7 @@ impl Decipher {
         assert!(input.len() == 16);
         let _ = (*decryptor)
           .decrypt_padded_b2b_mut::<Pkcs7>(input, output)
-          .map_err(|_| type_error("Cannot unpad the input data"))?;
+          .map_err(|_| DecipherError::CannotUnpadInputData)?;
         Ok(())
       }
       (Aes128Ecb(mut decryptor), false) => {
@@ -467,7 +530,7 @@ impl Decipher {
         assert!(input.len() == 16);
         let _ = (*decryptor)
           .decrypt_padded_b2b_mut::<Pkcs7>(input, output)
-          .map_err(|_| type_error("Cannot unpad the input data"))?;
+          .map_err(|_| DecipherError::CannotUnpadInputData)?;
         Ok(())
       }
       (Aes192Ecb(mut decryptor), false) => {
@@ -481,7 +544,7 @@ impl Decipher {
         assert!(input.len() == 16);
         let _ = (*decryptor)
           .decrypt_padded_b2b_mut::<Pkcs7>(input, output)
-          .map_err(|_| type_error("Cannot unpad the input data"))?;
+          .map_err(|_| DecipherError::CannotUnpadInputData)?;
         Ok(())
       }
       (Aes256Ecb(mut decryptor), false) => {
@@ -496,28 +559,28 @@ impl Decipher {
         if tag.as_slice() == auth_tag {
           Ok(())
         } else {
-          Err(type_error("Failed to authenticate data"))
+          Err(DecipherError::DataAuthenticationFailed)
         }
       }
-      (Aes128Gcm(_), false) => Err(type_error(
-        "setAutoPadding(false) not supported for Aes256Gcm yet",
-      )),
+      (Aes128Gcm(_), false) => {
+        Err(DecipherError::SetAutoPaddingFalseAes128GcmUnsupported)
+      }
       (Aes256Gcm(decipher), true) => {
         let tag = decipher.finish();
         if tag.as_slice() == auth_tag {
           Ok(())
         } else {
-          Err(type_error("Failed to authenticate data"))
+          Err(DecipherError::DataAuthenticationFailed)
         }
       }
-      (Aes256Gcm(_), false) => Err(type_error(
-        "setAutoPadding(false) not supported for Aes256Gcm yet",
-      )),
+      (Aes256Gcm(_), false) => {
+        Err(DecipherError::SetAutoPaddingFalseAes256GcmUnsupported)
+      }
       (Aes256Cbc(decryptor), true) => {
         assert!(input.len() == 16);
         let _ = (*decryptor)
           .decrypt_padded_b2b_mut::<Pkcs7>(input, output)
-          .map_err(|_| type_error("Cannot unpad the input data"))?;
+          .map_err(|_| DecipherError::CannotUnpadInputData)?;
         Ok(())
       }
       (Aes256Cbc(mut decryptor), false) => {
diff --git a/ext/node/ops/crypto/digest.rs b/ext/node/ops/crypto/digest.rs
index 293e8e0637..a7d8fb51f1 100644
--- a/ext/node/ops/crypto/digest.rs
+++ b/ext/node/ops/crypto/digest.rs
@@ -1,6 +1,4 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-use deno_core::error::generic_error;
-use deno_core::error::AnyError;
 use deno_core::GarbageCollected;
 use digest::Digest;
 use digest::DynDigest;
@@ -19,7 +17,7 @@ impl Hasher {
   pub fn new(
     algorithm: &str,
     output_length: Option<usize>,
-  ) -> Result<Self, AnyError> {
+  ) -> Result<Self, HashError> {
     let hash = Hash::new(algorithm, output_length)?;
 
     Ok(Self {
@@ -44,7 +42,7 @@ impl Hasher {
   pub fn clone_inner(
     &self,
     output_length: Option<usize>,
-  ) -> Result<Option<Self>, AnyError> {
+  ) -> Result<Option<Self>, HashError> {
     let hash = self.hash.borrow();
     let Some(hash) = hash.as_ref() else {
       return Ok(None);
@@ -184,11 +182,19 @@ pub enum Hash {
 
 use Hash::*;
 
+#[derive(Debug, thiserror::Error)]
+pub enum HashError {
+  #[error("Output length mismatch for non-extendable algorithm")]
+  OutputLengthMismatch,
+  #[error("Digest method not supported: {0}")]
+  DigestMethodUnsupported(String),
+}
+
 impl Hash {
   pub fn new(
     algorithm_name: &str,
     output_length: Option<usize>,
-  ) -> Result<Self, AnyError> {
+  ) -> Result<Self, HashError> {
     match algorithm_name {
       "shake128" => return Ok(Shake128(Default::default(), output_length)),
       "shake256" => return Ok(Shake256(Default::default(), output_length)),
@@ -201,17 +207,13 @@ impl Hash {
         let digest: D = Digest::new();
         if let Some(length) = output_length {
           if length != digest.output_size() {
-            return Err(generic_error(
-              "Output length mismatch for non-extendable algorithm",
-            ));
+            return Err(HashError::OutputLengthMismatch);
           }
         }
         FixedSize(Box::new(digest))
       },
       _ => {
-        return Err(generic_error(format!(
-          "Digest method not supported: {algorithm_name}"
-        )))
+        return Err(HashError::DigestMethodUnsupported(algorithm_name.to_string()))
       }
     );
 
@@ -243,14 +245,12 @@ impl Hash {
   pub fn clone_hash(
     &self,
     output_length: Option<usize>,
-  ) -> Result<Self, AnyError> {
+  ) -> Result<Self, HashError> {
     let hash = match self {
       FixedSize(context) => {
         if let Some(length) = output_length {
           if length != context.output_size() {
-            return Err(generic_error(
-              "Output length mismatch for non-extendable algorithm",
-            ));
+            return Err(HashError::OutputLengthMismatch);
           }
         }
         FixedSize(context.box_clone())
diff --git a/ext/node/ops/crypto/keys.rs b/ext/node/ops/crypto/keys.rs
index 867b34e044..f164972d48 100644
--- a/ext/node/ops/crypto/keys.rs
+++ b/ext/node/ops/crypto/keys.rs
@@ -4,9 +4,7 @@ use std::borrow::Cow;
 use std::cell::RefCell;
 
 use base64::Engine;
-use deno_core::error::generic_error;
 use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::serde_v8::BigInt as V8BigInt;
 use deno_core::unsync::spawn_blocking;
@@ -46,6 +44,7 @@ use spki::der::Reader as _;
 use spki::DecodePublicKey as _;
 use spki::EncodePublicKey as _;
 use spki::SubjectPublicKeyInfoRef;
+use x509_parser::error::X509Error;
 use x509_parser::x509;
 
 use super::dh;
@@ -236,9 +235,11 @@ impl RsaPssPrivateKey {
 }
 
 impl EcPublicKey {
-  pub fn to_jwk(&self) -> Result<elliptic_curve::JwkEcKey, AnyError> {
+  pub fn to_jwk(&self) -> Result<JwkEcKey, AsymmetricPublicKeyJwkError> {
     match self {
-      EcPublicKey::P224(_) => Err(type_error("Unsupported JWK EC curve: P224")),
+      EcPublicKey::P224(_) => {
+        Err(AsymmetricPublicKeyJwkError::UnsupportedJwkEcCurveP224)
+      }
       EcPublicKey::P256(key) => Ok(key.to_jwk()),
       EcPublicKey::P384(key) => Ok(key.to_jwk()),
     }
@@ -363,49 +364,201 @@ impl<'a> TryFrom<rsa::pkcs8::der::asn1::AnyRef<'a>> for RsaPssParameters<'a> {
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum X509PublicKeyError {
+  #[error(transparent)]
+  X509(#[from] x509_parser::error::X509Error),
+  #[error(transparent)]
+  Rsa(#[from] rsa::Error),
+  #[error(transparent)]
+  Asn1(#[from] x509_parser::der_parser::asn1_rs::Error),
+  #[error(transparent)]
+  Ec(#[from] elliptic_curve::Error),
+  #[error("unsupported ec named curve")]
+  UnsupportedEcNamedCurve,
+  #[error("missing ec parameters")]
+  MissingEcParameters,
+  #[error("malformed DSS public key")]
+  MalformedDssPublicKey,
+  #[error("unsupported x509 public key type")]
+  UnsupportedX509KeyType,
+}
+
+#[derive(Debug, thiserror::Error)]
+pub enum RsaJwkError {
+  #[error(transparent)]
+  Base64(#[from] base64::DecodeError),
+  #[error(transparent)]
+  Rsa(#[from] rsa::Error),
+  #[error("missing RSA private component")]
+  MissingRsaPrivateComponent,
+}
+
+#[derive(Debug, thiserror::Error)]
+pub enum EcJwkError {
+  #[error(transparent)]
+  Ec(#[from] elliptic_curve::Error),
+  #[error("unsupported curve: {0}")]
+  UnsupportedCurve(String),
+}
+
+#[derive(Debug, thiserror::Error)]
+pub enum EdRawError {
+  #[error(transparent)]
+  Ed25519Signature(#[from] ed25519_dalek::SignatureError),
+  #[error("invalid Ed25519 key")]
+  InvalidEd25519Key,
+  #[error("unsupported curve")]
+  UnsupportedCurve,
+}
+
+#[derive(Debug, thiserror::Error)]
+pub enum AsymmetricPrivateKeyError {
+  #[error("invalid PEM private key: not valid utf8 starting at byte {0}")]
+  InvalidPemPrivateKeyInvalidUtf8(usize),
+  #[error("invalid encrypted PEM private key")]
+  InvalidEncryptedPemPrivateKey,
+  #[error("invalid PEM private key")]
+  InvalidPemPrivateKey,
+  #[error("encrypted private key requires a passphrase to decrypt")]
+  EncryptedPrivateKeyRequiresPassphraseToDecrypt,
+  #[error("invalid PKCS#1 private key")]
+  InvalidPkcs1PrivateKey,
+  #[error("invalid SEC1 private key")]
+  InvalidSec1PrivateKey,
+  #[error("unsupported PEM label: {0}")]
+  UnsupportedPemLabel(String),
+  #[error(transparent)]
+  RsaPssParamsParse(#[from] RsaPssParamsParseError),
+  #[error("invalid encrypted PKCS#8 private key")]
+  InvalidEncryptedPkcs8PrivateKey,
+  #[error("invalid PKCS#8 private key")]
+  InvalidPkcs8PrivateKey,
+  #[error("PKCS#1 private key does not support encryption with passphrase")]
+  Pkcs1PrivateKeyDoesNotSupportEncryptionWithPassphrase,
+  #[error("SEC1 private key does not support encryption with passphrase")]
+  Sec1PrivateKeyDoesNotSupportEncryptionWithPassphrase,
+  #[error("unsupported ec named curve")]
+  UnsupportedEcNamedCurve,
+  #[error("invalid private key")]
+  InvalidPrivateKey,
+  #[error("invalid DSA private key")]
+  InvalidDsaPrivateKey,
+  #[error("malformed or missing named curve in ec parameters")]
+  MalformedOrMissingNamedCurveInEcParameters,
+  #[error("unsupported key type: {0}")]
+  UnsupportedKeyType(String),
+  #[error("unsupported key format: {0}")]
+  UnsupportedKeyFormat(String),
+  #[error("invalid x25519 private key")]
+  InvalidX25519PrivateKey,
+  #[error("x25519 private key is the wrong length")]
+  X25519PrivateKeyIsWrongLength,
+  #[error("invalid Ed25519 private key")]
+  InvalidEd25519PrivateKey,
+  #[error("missing dh parameters")]
+  MissingDhParameters,
+  #[error("unsupported private key oid")]
+  UnsupportedPrivateKeyOid,
+}
+
+#[derive(Debug, thiserror::Error)]
+pub enum AsymmetricPublicKeyError {
+  #[error("invalid PEM private key: not valid utf8 starting at byte {0}")]
+  InvalidPemPrivateKeyInvalidUtf8(usize),
+  #[error("invalid PEM public key")]
+  InvalidPemPublicKey,
+  #[error("invalid PKCS#1 public key")]
+  InvalidPkcs1PublicKey,
+  #[error(transparent)]
+  AsymmetricPrivateKey(#[from] AsymmetricPrivateKeyError),
+  #[error("invalid x509 certificate")]
+  InvalidX509Certificate,
+  #[error(transparent)]
+  X509(#[from] x509_parser::nom::Err<X509Error>),
+  #[error(transparent)]
+  X509PublicKey(#[from] X509PublicKeyError),
+  #[error("unsupported PEM label: {0}")]
+  UnsupportedPemLabel(String),
+  #[error("invalid SPKI public key")]
+  InvalidSpkiPublicKey,
+  #[error("unsupported key type: {0}")]
+  UnsupportedKeyType(String),
+  #[error("unsupported key format: {0}")]
+  UnsupportedKeyFormat(String),
+  #[error(transparent)]
+  Spki(#[from] spki::Error),
+  #[error(transparent)]
+  Pkcs1(#[from] rsa::pkcs1::Error),
+  #[error(transparent)]
+  RsaPssParamsParse(#[from] RsaPssParamsParseError),
+  #[error("malformed DSS public key")]
+  MalformedDssPublicKey,
+  #[error("malformed or missing named curve in ec parameters")]
+  MalformedOrMissingNamedCurveInEcParameters,
+  #[error("malformed or missing public key in ec spki")]
+  MalformedOrMissingPublicKeyInEcSpki,
+  #[error(transparent)]
+  Ec(#[from] elliptic_curve::Error),
+  #[error("unsupported ec named curve")]
+  UnsupportedEcNamedCurve,
+  #[error("malformed or missing public key in x25519 spki")]
+  MalformedOrMissingPublicKeyInX25519Spki,
+  #[error("x25519 public key is too short")]
+  X25519PublicKeyIsTooShort,
+  #[error("invalid Ed25519 public key")]
+  InvalidEd25519PublicKey,
+  #[error("missing dh parameters")]
+  MissingDhParameters,
+  #[error("malformed dh parameters")]
+  MalformedDhParameters,
+  #[error("malformed or missing public key in dh spki")]
+  MalformedOrMissingPublicKeyInDhSpki,
+  #[error("unsupported private key oid")]
+  UnsupportedPrivateKeyOid,
+}
+
 impl KeyObjectHandle {
   pub fn new_asymmetric_private_key_from_js(
     key: &[u8],
     format: &str,
     typ: &str,
     passphrase: Option<&[u8]>,
-  ) -> Result<KeyObjectHandle, AnyError> {
+  ) -> Result<KeyObjectHandle, AsymmetricPrivateKeyError> {
     let document = match format {
       "pem" => {
         let pem = std::str::from_utf8(key).map_err(|err| {
-          type_error(format!(
-            "invalid PEM private key: not valid utf8 starting at byte {}",
-            err.valid_up_to()
-          ))
+          AsymmetricPrivateKeyError::InvalidPemPrivateKeyInvalidUtf8(
+            err.valid_up_to(),
+          )
         })?;
 
         if let Some(passphrase) = passphrase {
-          SecretDocument::from_pkcs8_encrypted_pem(pem, passphrase)
-            .map_err(|_| type_error("invalid encrypted PEM private key"))?
+          SecretDocument::from_pkcs8_encrypted_pem(pem, passphrase).map_err(
+            |_| AsymmetricPrivateKeyError::InvalidEncryptedPemPrivateKey,
+          )?
         } else {
           let (label, doc) = SecretDocument::from_pem(pem)
-            .map_err(|_| type_error("invalid PEM private key"))?;
+            .map_err(|_| AsymmetricPrivateKeyError::InvalidPemPrivateKey)?;
 
           match label {
             EncryptedPrivateKeyInfo::PEM_LABEL => {
-              return Err(type_error(
-                "encrypted private key requires a passphrase to decrypt",
-              ))
+              return Err(AsymmetricPrivateKeyError::EncryptedPrivateKeyRequiresPassphraseToDecrypt);
             }
             PrivateKeyInfo::PEM_LABEL => doc,
             rsa::pkcs1::RsaPrivateKey::PEM_LABEL => {
-              SecretDocument::from_pkcs1_der(doc.as_bytes())
-                .map_err(|_| type_error("invalid PKCS#1 private key"))?
+              SecretDocument::from_pkcs1_der(doc.as_bytes()).map_err(|_| {
+                AsymmetricPrivateKeyError::InvalidPkcs1PrivateKey
+              })?
             }
             sec1::EcPrivateKey::PEM_LABEL => {
               SecretDocument::from_sec1_der(doc.as_bytes())
-                .map_err(|_| type_error("invalid SEC1 private key"))?
+                .map_err(|_| AsymmetricPrivateKeyError::InvalidSec1PrivateKey)?
             }
             _ => {
-              return Err(type_error(format!(
-                "unsupported PEM label: {}",
-                label
-              )))
+              return Err(AsymmetricPrivateKeyError::UnsupportedPemLabel(
+                label.to_string(),
+              ))
             }
           }
         }
@@ -413,54 +566,57 @@ impl KeyObjectHandle {
       "der" => match typ {
         "pkcs8" => {
           if let Some(passphrase) = passphrase {
-            SecretDocument::from_pkcs8_encrypted_der(key, passphrase)
-              .map_err(|_| type_error("invalid encrypted PKCS#8 private key"))?
+            SecretDocument::from_pkcs8_encrypted_der(key, passphrase).map_err(
+              |_| AsymmetricPrivateKeyError::InvalidEncryptedPkcs8PrivateKey,
+            )?
           } else {
             SecretDocument::from_pkcs8_der(key)
-              .map_err(|_| type_error("invalid PKCS#8 private key"))?
+              .map_err(|_| AsymmetricPrivateKeyError::InvalidPkcs8PrivateKey)?
           }
         }
         "pkcs1" => {
           if passphrase.is_some() {
-            return Err(type_error(
-              "PKCS#1 private key does not support encryption with passphrase",
-            ));
+            return Err(AsymmetricPrivateKeyError::Pkcs1PrivateKeyDoesNotSupportEncryptionWithPassphrase);
           }
           SecretDocument::from_pkcs1_der(key)
-            .map_err(|_| type_error("invalid PKCS#1 private key"))?
+            .map_err(|_| AsymmetricPrivateKeyError::InvalidPkcs1PrivateKey)?
         }
         "sec1" => {
           if passphrase.is_some() {
-            return Err(type_error(
-              "SEC1 private key does not support encryption with passphrase",
-            ));
+            return Err(AsymmetricPrivateKeyError::Sec1PrivateKeyDoesNotSupportEncryptionWithPassphrase);
           }
           SecretDocument::from_sec1_der(key)
-            .map_err(|_| type_error("invalid SEC1 private key"))?
+            .map_err(|_| AsymmetricPrivateKeyError::InvalidSec1PrivateKey)?
+        }
+        _ => {
+          return Err(AsymmetricPrivateKeyError::UnsupportedKeyType(
+            typ.to_string(),
+          ))
         }
-        _ => return Err(type_error(format!("unsupported key type: {}", typ))),
       },
       _ => {
-        return Err(type_error(format!("unsupported key format: {}", format)))
+        return Err(AsymmetricPrivateKeyError::UnsupportedKeyFormat(
+          format.to_string(),
+        ))
       }
     };
 
     let pk_info = PrivateKeyInfo::try_from(document.as_bytes())
-      .map_err(|_| type_error("invalid private key"))?;
+      .map_err(|_| AsymmetricPrivateKeyError::InvalidPrivateKey)?;
 
     let alg = pk_info.algorithm.oid;
     let private_key = match alg {
       RSA_ENCRYPTION_OID => {
         let private_key =
           rsa::RsaPrivateKey::from_pkcs1_der(pk_info.private_key)
-            .map_err(|_| type_error("invalid PKCS#1 private key"))?;
+            .map_err(|_| AsymmetricPrivateKeyError::InvalidPkcs1PrivateKey)?;
         AsymmetricPrivateKey::Rsa(private_key)
       }
       RSASSA_PSS_OID => {
         let details = parse_rsa_pss_params(pk_info.algorithm.parameters)?;
         let private_key =
           rsa::RsaPrivateKey::from_pkcs1_der(pk_info.private_key)
-            .map_err(|_| type_error("invalid PKCS#1 private key"))?;
+            .map_err(|_| AsymmetricPrivateKeyError::InvalidPkcs1PrivateKey)?;
         AsymmetricPrivateKey::RsaPss(RsaPssPrivateKey {
           key: private_key,
           details,
@@ -468,40 +624,43 @@ impl KeyObjectHandle {
       }
       DSA_OID => {
         let private_key = dsa::SigningKey::try_from(pk_info)
-          .map_err(|_| type_error("invalid DSA private key"))?;
+          .map_err(|_| AsymmetricPrivateKeyError::InvalidDsaPrivateKey)?;
         AsymmetricPrivateKey::Dsa(private_key)
       }
       EC_OID => {
         let named_curve = pk_info.algorithm.parameters_oid().map_err(|_| {
-          type_error("malformed or missing named curve in ec parameters")
+          AsymmetricPrivateKeyError::MalformedOrMissingNamedCurveInEcParameters
         })?;
         match named_curve {
           ID_SECP224R1_OID => {
-            let secret_key =
-              p224::SecretKey::from_sec1_der(pk_info.private_key)
-                .map_err(|_| type_error("invalid SEC1 private key"))?;
+            let secret_key = p224::SecretKey::from_sec1_der(
+              pk_info.private_key,
+            )
+            .map_err(|_| AsymmetricPrivateKeyError::InvalidSec1PrivateKey)?;
             AsymmetricPrivateKey::Ec(EcPrivateKey::P224(secret_key))
           }
           ID_SECP256R1_OID => {
-            let secret_key =
-              p256::SecretKey::from_sec1_der(pk_info.private_key)
-                .map_err(|_| type_error("invalid SEC1 private key"))?;
+            let secret_key = p256::SecretKey::from_sec1_der(
+              pk_info.private_key,
+            )
+            .map_err(|_| AsymmetricPrivateKeyError::InvalidSec1PrivateKey)?;
             AsymmetricPrivateKey::Ec(EcPrivateKey::P256(secret_key))
           }
           ID_SECP384R1_OID => {
-            let secret_key =
-              p384::SecretKey::from_sec1_der(pk_info.private_key)
-                .map_err(|_| type_error("invalid SEC1 private key"))?;
+            let secret_key = p384::SecretKey::from_sec1_der(
+              pk_info.private_key,
+            )
+            .map_err(|_| AsymmetricPrivateKeyError::InvalidSec1PrivateKey)?;
             AsymmetricPrivateKey::Ec(EcPrivateKey::P384(secret_key))
           }
-          _ => return Err(type_error("unsupported ec named curve")),
+          _ => return Err(AsymmetricPrivateKeyError::UnsupportedEcNamedCurve),
         }
       }
       X25519_OID => {
         let string_ref = OctetStringRef::from_der(pk_info.private_key)
-          .map_err(|_| type_error("invalid x25519 private key"))?;
+          .map_err(|_| AsymmetricPrivateKeyError::InvalidX25519PrivateKey)?;
         if string_ref.as_bytes().len() != 32 {
-          return Err(type_error("x25519 private key is the wrong length"));
+          return Err(AsymmetricPrivateKeyError::X25519PrivateKeyIsWrongLength);
         }
         let mut bytes = [0; 32];
         bytes.copy_from_slice(string_ref.as_bytes());
@@ -509,22 +668,22 @@ impl KeyObjectHandle {
       }
       ED25519_OID => {
         let signing_key = ed25519_dalek::SigningKey::try_from(pk_info)
-          .map_err(|_| type_error("invalid Ed25519 private key"))?;
+          .map_err(|_| AsymmetricPrivateKeyError::InvalidEd25519PrivateKey)?;
         AsymmetricPrivateKey::Ed25519(signing_key)
       }
       DH_KEY_AGREEMENT_OID => {
         let params = pk_info
           .algorithm
           .parameters
-          .ok_or_else(|| type_error("missing dh parameters"))?;
+          .ok_or(AsymmetricPrivateKeyError::MissingDhParameters)?;
         let params = pkcs3::DhParameter::from_der(&params.to_der().unwrap())
-          .map_err(|_| type_error("malformed dh parameters"))?;
+          .map_err(|_| AsymmetricPrivateKeyError::MissingDhParameters)?;
         AsymmetricPrivateKey::Dh(DhPrivateKey {
           key: dh::PrivateKey::from_bytes(pk_info.private_key),
           params,
         })
       }
-      _ => return Err(type_error("unsupported private key oid")),
+      _ => return Err(AsymmetricPrivateKeyError::UnsupportedPrivateKeyOid),
     };
 
     Ok(KeyObjectHandle::AsymmetricPrivate(private_key))
@@ -532,7 +691,7 @@ impl KeyObjectHandle {
 
   pub fn new_x509_public_key(
     spki: &x509::SubjectPublicKeyInfo,
-  ) -> Result<KeyObjectHandle, AnyError> {
+  ) -> Result<KeyObjectHandle, X509PublicKeyError> {
     use x509_parser::der_parser::asn1_rs::oid;
     use x509_parser::public_key::PublicKey;
 
@@ -565,18 +724,18 @@ impl KeyObjectHandle {
               let public_key = p384::PublicKey::from_sec1_bytes(data)?;
               AsymmetricPublicKey::Ec(EcPublicKey::P384(public_key))
             }
-            _ => return Err(type_error("unsupported ec named curve")),
+            _ => return Err(X509PublicKeyError::UnsupportedEcNamedCurve),
           }
         } else {
-          return Err(type_error("missing ec parameters"));
+          return Err(X509PublicKeyError::MissingEcParameters);
         }
       }
       PublicKey::DSA(_) => {
         let verifying_key = dsa::VerifyingKey::from_public_key_der(spki.raw)
-          .map_err(|_| type_error("malformed DSS public key"))?;
+          .map_err(|_| X509PublicKeyError::MalformedDssPublicKey)?;
         AsymmetricPublicKey::Dsa(verifying_key)
       }
-      _ => return Err(type_error("unsupported x509 public key type")),
+      _ => return Err(X509PublicKeyError::UnsupportedX509KeyType),
     };
 
     Ok(KeyObjectHandle::AsymmetricPublic(key))
@@ -585,7 +744,7 @@ impl KeyObjectHandle {
   pub fn new_rsa_jwk(
     jwk: RsaJwkKey,
     is_public: bool,
-  ) -> Result<KeyObjectHandle, AnyError> {
+  ) -> Result<KeyObjectHandle, RsaJwkError> {
     use base64::prelude::BASE64_URL_SAFE_NO_PAD;
 
     let n = BASE64_URL_SAFE_NO_PAD.decode(jwk.n.as_bytes())?;
@@ -604,19 +763,19 @@ impl KeyObjectHandle {
       let d = BASE64_URL_SAFE_NO_PAD.decode(
         jwk
           .d
-          .ok_or_else(|| type_error("missing RSA private component"))?
+          .ok_or(RsaJwkError::MissingRsaPrivateComponent)?
           .as_bytes(),
       )?;
       let p = BASE64_URL_SAFE_NO_PAD.decode(
         jwk
           .p
-          .ok_or_else(|| type_error("missing RSA private component"))?
+          .ok_or(RsaJwkError::MissingRsaPrivateComponent)?
           .as_bytes(),
       )?;
       let q = BASE64_URL_SAFE_NO_PAD.decode(
         jwk
           .q
-          .ok_or_else(|| type_error("missing RSA private component"))?
+          .ok_or(RsaJwkError::MissingRsaPrivateComponent)?
           .as_bytes(),
       )?;
 
@@ -640,7 +799,7 @@ impl KeyObjectHandle {
   pub fn new_ec_jwk(
     jwk: &JwkEcKey,
     is_public: bool,
-  ) -> Result<KeyObjectHandle, AnyError> {
+  ) -> Result<KeyObjectHandle, EcJwkError> {
     //  https://datatracker.ietf.org/doc/html/rfc7518#section-6.2.1.1
     let handle = match jwk.crv() {
       "P-256" if is_public => {
@@ -660,7 +819,7 @@ impl KeyObjectHandle {
         EcPrivateKey::P384(p384::SecretKey::from_jwk(jwk)?),
       )),
       _ => {
-        return Err(type_error(format!("unsupported curve: {}", jwk.crv())));
+        return Err(EcJwkError::UnsupportedCurve(jwk.crv().to_string()));
       }
     };
 
@@ -671,12 +830,11 @@ impl KeyObjectHandle {
     curve: &str,
     data: &[u8],
     is_public: bool,
-  ) -> Result<KeyObjectHandle, AnyError> {
+  ) -> Result<KeyObjectHandle, EdRawError> {
     match curve {
       "Ed25519" => {
-        let data = data
-          .try_into()
-          .map_err(|_| type_error("invalid Ed25519 key"))?;
+        let data =
+          data.try_into().map_err(|_| EdRawError::InvalidEd25519Key)?;
         if !is_public {
           Ok(KeyObjectHandle::AsymmetricPrivate(
             AsymmetricPrivateKey::Ed25519(
@@ -692,9 +850,8 @@ impl KeyObjectHandle {
         }
       }
       "X25519" => {
-        let data: [u8; 32] = data
-          .try_into()
-          .map_err(|_| type_error("invalid x25519 key"))?;
+        let data: [u8; 32] =
+          data.try_into().map_err(|_| EdRawError::InvalidEd25519Key)?;
         if !is_public {
           Ok(KeyObjectHandle::AsymmetricPrivate(
             AsymmetricPrivateKey::X25519(x25519_dalek::StaticSecret::from(
@@ -707,7 +864,7 @@ impl KeyObjectHandle {
           ))
         }
       }
-      _ => Err(type_error("unsupported curve")),
+      _ => Err(EdRawError::UnsupportedCurve),
     }
   }
 
@@ -716,24 +873,23 @@ impl KeyObjectHandle {
     format: &str,
     typ: &str,
     passphrase: Option<&[u8]>,
-  ) -> Result<KeyObjectHandle, AnyError> {
+  ) -> Result<KeyObjectHandle, AsymmetricPublicKeyError> {
     let document = match format {
       "pem" => {
         let pem = std::str::from_utf8(key).map_err(|err| {
-          type_error(format!(
-            "invalid PEM public key: not valid utf8 starting at byte {}",
-            err.valid_up_to()
-          ))
+          AsymmetricPublicKeyError::InvalidPemPrivateKeyInvalidUtf8(
+            err.valid_up_to(),
+          )
         })?;
 
         let (label, document) = Document::from_pem(pem)
-          .map_err(|_| type_error("invalid PEM public key"))?;
+          .map_err(|_| AsymmetricPublicKeyError::InvalidPemPublicKey)?;
 
         match label {
           SubjectPublicKeyInfoRef::PEM_LABEL => document,
           rsa::pkcs1::RsaPublicKey::PEM_LABEL => {
             Document::from_pkcs1_der(document.as_bytes())
-              .map_err(|_| type_error("invalid PKCS#1 public key"))?
+              .map_err(|_| AsymmetricPublicKeyError::InvalidPkcs1PublicKey)?
           }
           EncryptedPrivateKeyInfo::PEM_LABEL
           | PrivateKeyInfo::PEM_LABEL
@@ -754,27 +910,36 @@ impl KeyObjectHandle {
           }
           "CERTIFICATE" => {
             let (_, pem) = x509_parser::pem::parse_x509_pem(pem.as_bytes())
-              .map_err(|_| type_error("invalid x509 certificate"))?;
+              .map_err(|_| AsymmetricPublicKeyError::InvalidX509Certificate)?;
 
             let cert = pem.parse_x509()?;
             let public_key = cert.tbs_certificate.subject_pki;
 
-            return KeyObjectHandle::new_x509_public_key(&public_key);
+            return KeyObjectHandle::new_x509_public_key(&public_key)
+              .map_err(Into::into);
           }
           _ => {
-            return Err(type_error(format!("unsupported PEM label: {}", label)))
+            return Err(AsymmetricPublicKeyError::UnsupportedPemLabel(
+              label.to_string(),
+            ))
           }
         }
       }
       "der" => match typ {
         "pkcs1" => Document::from_pkcs1_der(key)
-          .map_err(|_| type_error("invalid PKCS#1 public key"))?,
+          .map_err(|_| AsymmetricPublicKeyError::InvalidPkcs1PublicKey)?,
         "spki" => Document::from_public_key_der(key)
-          .map_err(|_| type_error("invalid SPKI public key"))?,
-        _ => return Err(type_error(format!("unsupported key type: {}", typ))),
+          .map_err(|_| AsymmetricPublicKeyError::InvalidSpkiPublicKey)?,
+        _ => {
+          return Err(AsymmetricPublicKeyError::UnsupportedKeyType(
+            typ.to_string(),
+          ))
+        }
       },
       _ => {
-        return Err(type_error(format!("unsupported key format: {}", format)))
+        return Err(AsymmetricPublicKeyError::UnsupportedKeyType(
+          format.to_string(),
+        ))
       }
     };
 
@@ -799,16 +964,16 @@ impl KeyObjectHandle {
       }
       DSA_OID => {
         let verifying_key = dsa::VerifyingKey::try_from(spki)
-          .map_err(|_| type_error("malformed DSS public key"))?;
+          .map_err(|_| AsymmetricPublicKeyError::MalformedDssPublicKey)?;
         AsymmetricPublicKey::Dsa(verifying_key)
       }
       EC_OID => {
         let named_curve = spki.algorithm.parameters_oid().map_err(|_| {
-          type_error("malformed or missing named curve in ec parameters")
-        })?;
-        let data = spki.subject_public_key.as_bytes().ok_or_else(|| {
-          type_error("malformed or missing public key in ec spki")
+          AsymmetricPublicKeyError::MalformedOrMissingNamedCurveInEcParameters
         })?;
+        let data = spki.subject_public_key.as_bytes().ok_or(
+          AsymmetricPublicKeyError::MalformedOrMissingPublicKeyInEcSpki,
+        )?;
 
         match named_curve {
           ID_SECP224R1_OID => {
@@ -823,54 +988,68 @@ impl KeyObjectHandle {
             let public_key = p384::PublicKey::from_sec1_bytes(data)?;
             AsymmetricPublicKey::Ec(EcPublicKey::P384(public_key))
           }
-          _ => return Err(type_error("unsupported ec named curve")),
+          _ => return Err(AsymmetricPublicKeyError::UnsupportedEcNamedCurve),
         }
       }
       X25519_OID => {
         let mut bytes = [0; 32];
-        let data = spki.subject_public_key.as_bytes().ok_or_else(|| {
-          type_error("malformed or missing public key in x25519 spki")
-        })?;
+        let data = spki.subject_public_key.as_bytes().ok_or(
+          AsymmetricPublicKeyError::MalformedOrMissingPublicKeyInX25519Spki,
+        )?;
         if data.len() < 32 {
-          return Err(type_error("x25519 public key is too short"));
+          return Err(AsymmetricPublicKeyError::X25519PublicKeyIsTooShort);
         }
         bytes.copy_from_slice(&data[0..32]);
         AsymmetricPublicKey::X25519(x25519_dalek::PublicKey::from(bytes))
       }
       ED25519_OID => {
         let verifying_key = ed25519_dalek::VerifyingKey::try_from(spki)
-          .map_err(|_| type_error("invalid Ed25519 private key"))?;
+          .map_err(|_| AsymmetricPublicKeyError::InvalidEd25519PublicKey)?;
         AsymmetricPublicKey::Ed25519(verifying_key)
       }
       DH_KEY_AGREEMENT_OID => {
         let params = spki
           .algorithm
           .parameters
-          .ok_or_else(|| type_error("missing dh parameters"))?;
+          .ok_or(AsymmetricPublicKeyError::MissingDhParameters)?;
         let params = pkcs3::DhParameter::from_der(&params.to_der().unwrap())
-          .map_err(|_| type_error("malformed dh parameters"))?;
+          .map_err(|_| AsymmetricPublicKeyError::MalformedDhParameters)?;
         let Some(subject_public_key) = spki.subject_public_key.as_bytes()
         else {
-          return Err(type_error("malformed or missing public key in dh spki"));
+          return Err(
+            AsymmetricPublicKeyError::MalformedOrMissingPublicKeyInDhSpki,
+          );
         };
         AsymmetricPublicKey::Dh(DhPublicKey {
           key: dh::PublicKey::from_bytes(subject_public_key),
           params,
         })
       }
-      _ => return Err(type_error("unsupported public key oid")),
+      _ => return Err(AsymmetricPublicKeyError::UnsupportedPrivateKeyOid),
     };
 
     Ok(KeyObjectHandle::AsymmetricPublic(public_key))
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum RsaPssParamsParseError {
+  #[error("malformed pss private key parameters")]
+  MalformedPssPrivateKeyParameters,
+  #[error("unsupported pss hash algorithm")]
+  UnsupportedPssHashAlgorithm,
+  #[error("unsupported pss mask gen algorithm")]
+  UnsupportedPssMaskGenAlgorithm,
+  #[error("malformed or missing pss mask gen algorithm parameters")]
+  MalformedOrMissingPssMaskGenAlgorithm,
+}
+
 fn parse_rsa_pss_params(
   parameters: Option<AnyRef<'_>>,
-) -> Result<Option<RsaPssDetails>, deno_core::anyhow::Error> {
+) -> Result<Option<RsaPssDetails>, RsaPssParamsParseError> {
   let details = if let Some(parameters) = parameters {
     let params = RsaPssParameters::try_from(parameters)
-      .map_err(|_| type_error("malformed pss private key parameters"))?;
+      .map_err(|_| RsaPssParamsParseError::MalformedPssPrivateKeyParameters)?;
 
     let hash_algorithm = match params.hash_algorithm.map(|k| k.oid) {
       Some(ID_SHA1_OID) => RsaPssHashAlgorithm::Sha1,
@@ -881,16 +1060,16 @@ fn parse_rsa_pss_params(
       Some(ID_SHA512_224_OID) => RsaPssHashAlgorithm::Sha512_224,
       Some(ID_SHA512_256_OID) => RsaPssHashAlgorithm::Sha512_256,
       None => RsaPssHashAlgorithm::Sha1,
-      _ => return Err(type_error("unsupported pss hash algorithm")),
+      _ => return Err(RsaPssParamsParseError::UnsupportedPssHashAlgorithm),
     };
 
     let mf1_hash_algorithm = match params.mask_gen_algorithm {
       Some(alg) => {
         if alg.oid != ID_MFG1 {
-          return Err(type_error("unsupported pss mask gen algorithm"));
+          return Err(RsaPssParamsParseError::UnsupportedPssMaskGenAlgorithm);
         }
         let params = alg.parameters_oid().map_err(|_| {
-          type_error("malformed or missing pss mask gen algorithm parameters")
+          RsaPssParamsParseError::MalformedOrMissingPssMaskGenAlgorithm
         })?;
         match params {
           ID_SHA1_OID => RsaPssHashAlgorithm::Sha1,
@@ -900,7 +1079,9 @@ fn parse_rsa_pss_params(
           ID_SHA512_OID => RsaPssHashAlgorithm::Sha512,
           ID_SHA512_224_OID => RsaPssHashAlgorithm::Sha512_224,
           ID_SHA512_256_OID => RsaPssHashAlgorithm::Sha512_256,
-          _ => return Err(type_error("unsupported pss mask gen algorithm")),
+          _ => {
+            return Err(RsaPssParamsParseError::UnsupportedPssMaskGenAlgorithm)
+          }
         }
       }
       None => hash_algorithm,
@@ -921,14 +1102,49 @@ fn parse_rsa_pss_params(
   Ok(details)
 }
 
-use base64::prelude::BASE64_URL_SAFE_NO_PAD;
-
 fn bytes_to_b64(bytes: &[u8]) -> String {
+  use base64::prelude::BASE64_URL_SAFE_NO_PAD;
   BASE64_URL_SAFE_NO_PAD.encode(bytes)
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum AsymmetricPublicKeyJwkError {
+  #[error("key is not an asymmetric public key")]
+  KeyIsNotAsymmetricPublicKey,
+  #[error("Unsupported JWK EC curve: P224")]
+  UnsupportedJwkEcCurveP224,
+  #[error("jwk export not implemented for this key type")]
+  JwkExportNotImplementedForKeyType,
+}
+
+#[derive(Debug, thiserror::Error)]
+pub enum AsymmetricPublicKeyDerError {
+  #[error("key is not an asymmetric public key")]
+  KeyIsNotAsymmetricPublicKey,
+  #[error("invalid RSA public key")]
+  InvalidRsaPublicKey,
+  #[error("exporting non-RSA public key as PKCS#1 is not supported")]
+  ExportingNonRsaPublicKeyAsPkcs1Unsupported,
+  #[error("invalid EC public key")]
+  InvalidEcPublicKey,
+  #[error("exporting RSA-PSS public key as SPKI is not supported yet")]
+  ExportingNonRsaPssPublicKeyAsSpkiUnsupported,
+  #[error("invalid DSA public key")]
+  InvalidDsaPublicKey,
+  #[error("invalid X25519 public key")]
+  InvalidX25519PublicKey,
+  #[error("invalid Ed25519 public key")]
+  InvalidEd25519PublicKey,
+  #[error("invalid DH public key")]
+  InvalidDhPublicKey,
+  #[error("unsupported key type: {0}")]
+  UnsupportedKeyType(String),
+}
+
 impl AsymmetricPublicKey {
-  fn export_jwk(&self) -> Result<deno_core::serde_json::Value, AnyError> {
+  fn export_jwk(
+    &self,
+  ) -> Result<deno_core::serde_json::Value, AsymmetricPublicKeyJwkError> {
     match self {
       AsymmetricPublicKey::Ec(key) => {
         let jwk = key.to_jwk()?;
@@ -974,40 +1190,39 @@ impl AsymmetricPublicKey {
         });
         Ok(jwk)
       }
-      _ => Err(type_error("jwk export not implemented for this key type")),
+      _ => Err(AsymmetricPublicKeyJwkError::JwkExportNotImplementedForKeyType),
     }
   }
 
-  fn export_der(&self, typ: &str) -> Result<Box<[u8]>, AnyError> {
+  fn export_der(
+    &self,
+    typ: &str,
+  ) -> Result<Box<[u8]>, AsymmetricPublicKeyDerError> {
     match typ {
       "pkcs1" => match self {
         AsymmetricPublicKey::Rsa(key) => {
           let der = key
             .to_pkcs1_der()
-            .map_err(|_| type_error("invalid RSA public key"))?
+            .map_err(|_| AsymmetricPublicKeyDerError::InvalidRsaPublicKey)?
             .into_vec()
             .into_boxed_slice();
           Ok(der)
         }
-        _ => Err(type_error(
-          "exporting non-RSA public key as PKCS#1 is not supported",
-        )),
+        _ => Err(AsymmetricPublicKeyDerError::ExportingNonRsaPublicKeyAsPkcs1Unsupported),
       },
       "spki" => {
         let der = match self {
           AsymmetricPublicKey::Rsa(key) => key
             .to_public_key_der()
-            .map_err(|_| type_error("invalid RSA public key"))?
+            .map_err(|_| AsymmetricPublicKeyDerError::InvalidRsaPublicKey)?
             .into_vec()
             .into_boxed_slice(),
           AsymmetricPublicKey::RsaPss(_key) => {
-            return Err(generic_error(
-              "exporting RSA-PSS public key as SPKI is not supported yet",
-            ))
+            return Err(AsymmetricPublicKeyDerError::ExportingNonRsaPssPublicKeyAsSpkiUnsupported)
           }
           AsymmetricPublicKey::Dsa(key) => key
             .to_public_key_der()
-            .map_err(|_| type_error("invalid DSA public key"))?
+            .map_err(|_| AsymmetricPublicKeyDerError::InvalidDsaPublicKey)?
             .into_vec()
             .into_boxed_slice(),
           AsymmetricPublicKey::Ec(key) => {
@@ -1023,12 +1238,12 @@ impl AsymmetricPublicKey {
                 parameters: Some(asn1::AnyRef::from(&oid)),
               },
               subject_public_key: BitStringRef::from_bytes(&sec1)
-                .map_err(|_| type_error("invalid EC public key"))?,
+                .map_err(|_| AsymmetricPublicKeyDerError::InvalidEcPublicKey)?,
             };
 
             spki
               .to_der()
-              .map_err(|_| type_error("invalid EC public key"))?
+              .map_err(|_| AsymmetricPublicKeyDerError::InvalidEcPublicKey)?
               .into_boxed_slice()
           }
           AsymmetricPublicKey::X25519(key) => {
@@ -1038,12 +1253,12 @@ impl AsymmetricPublicKey {
                 parameters: None,
               },
               subject_public_key: BitStringRef::from_bytes(key.as_bytes())
-                .map_err(|_| type_error("invalid X25519 public key"))?,
+                .map_err(|_| AsymmetricPublicKeyDerError::InvalidX25519PublicKey)?,
             };
 
             spki
               .to_der()
-              .map_err(|_| type_error("invalid X25519 public key"))?
+              .map_err(|_| AsymmetricPublicKeyDerError::InvalidX25519PublicKey)?
               .into_boxed_slice()
           }
           AsymmetricPublicKey::Ed25519(key) => {
@@ -1053,12 +1268,12 @@ impl AsymmetricPublicKey {
                 parameters: None,
               },
               subject_public_key: BitStringRef::from_bytes(key.as_bytes())
-                .map_err(|_| type_error("invalid Ed25519 public key"))?,
+                .map_err(|_| AsymmetricPublicKeyDerError::InvalidEd25519PublicKey)?,
             };
 
             spki
               .to_der()
-              .map_err(|_| type_error("invalid Ed25519 public key"))?
+              .map_err(|_| AsymmetricPublicKeyDerError::InvalidEd25519PublicKey)?
               .into_boxed_slice()
           }
           AsymmetricPublicKey::Dh(key) => {
@@ -1071,43 +1286,67 @@ impl AsymmetricPublicKey {
               },
               subject_public_key: BitStringRef::from_bytes(&public_key_bytes)
                 .map_err(|_| {
-                type_error("invalid DH public key")
+                  AsymmetricPublicKeyDerError::InvalidDhPublicKey
               })?,
             };
             spki
               .to_der()
-              .map_err(|_| type_error("invalid DH public key"))?
+              .map_err(|_| AsymmetricPublicKeyDerError::InvalidDhPublicKey)?
               .into_boxed_slice()
           }
         };
         Ok(der)
       }
-      _ => Err(type_error(format!("unsupported key type: {}", typ))),
+      _ => Err(AsymmetricPublicKeyDerError::UnsupportedKeyType(typ.to_string())),
     }
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum AsymmetricPrivateKeyDerError {
+  #[error("key is not an asymmetric private key")]
+  KeyIsNotAsymmetricPrivateKey,
+  #[error("invalid RSA private key")]
+  InvalidRsaPrivateKey,
+  #[error("exporting non-RSA private key as PKCS#1 is not supported")]
+  ExportingNonRsaPrivateKeyAsPkcs1Unsupported,
+  #[error("invalid EC private key")]
+  InvalidEcPrivateKey,
+  #[error("exporting non-EC private key as SEC1 is not supported")]
+  ExportingNonEcPrivateKeyAsSec1Unsupported,
+  #[error("exporting RSA-PSS private key as PKCS#8 is not supported yet")]
+  ExportingNonRsaPssPrivateKeyAsPkcs8Unsupported,
+  #[error("invalid DSA private key")]
+  InvalidDsaPrivateKey,
+  #[error("invalid X25519 private key")]
+  InvalidX25519PrivateKey,
+  #[error("invalid Ed25519 private key")]
+  InvalidEd25519PrivateKey,
+  #[error("invalid DH private key")]
+  InvalidDhPrivateKey,
+  #[error("unsupported key type: {0}")]
+  UnsupportedKeyType(String),
+}
+
 impl AsymmetricPrivateKey {
   fn export_der(
     &self,
     typ: &str,
     // cipher: Option<&str>,
     // passphrase: Option<&str>,
-  ) -> Result<Box<[u8]>, AnyError> {
+  ) -> Result<Box<[u8]>, AsymmetricPrivateKeyDerError> {
     match typ {
       "pkcs1" => match self {
         AsymmetricPrivateKey::Rsa(key) => {
           let der = key
             .to_pkcs1_der()
-            .map_err(|_| type_error("invalid RSA private key"))?
+            .map_err(|_| AsymmetricPrivateKeyDerError::InvalidRsaPrivateKey)?
             .to_bytes()
             .to_vec()
             .into_boxed_slice();
           Ok(der)
         }
-        _ => Err(type_error(
-          "exporting non-RSA private key as PKCS#1 is not supported",
-        )),
+        _ => Err(AsymmetricPrivateKeyDerError::ExportingNonRsaPrivateKeyAsPkcs1Unsupported),
       },
       "sec1" => match self {
         AsymmetricPrivateKey::Ec(key) => {
@@ -1116,30 +1355,26 @@ impl AsymmetricPrivateKey {
             EcPrivateKey::P256(key) => key.to_sec1_der(),
             EcPrivateKey::P384(key) => key.to_sec1_der(),
           }
-          .map_err(|_| type_error("invalid EC private key"))?;
+          .map_err(|_| AsymmetricPrivateKeyDerError::InvalidEcPrivateKey)?;
           Ok(sec1.to_vec().into_boxed_slice())
         }
-        _ => Err(type_error(
-          "exporting non-EC private key as SEC1 is not supported",
-        )),
+        _ => Err(AsymmetricPrivateKeyDerError::ExportingNonEcPrivateKeyAsSec1Unsupported),
       },
       "pkcs8" => {
         let der = match self {
           AsymmetricPrivateKey::Rsa(key) => {
             let document = key
               .to_pkcs8_der()
-              .map_err(|_| type_error("invalid RSA private key"))?;
+              .map_err(|_| AsymmetricPrivateKeyDerError::InvalidRsaPrivateKey)?;
             document.to_bytes().to_vec().into_boxed_slice()
           }
           AsymmetricPrivateKey::RsaPss(_key) => {
-            return Err(generic_error(
-              "exporting RSA-PSS private key as PKCS#8 is not supported yet",
-            ))
+            return Err(AsymmetricPrivateKeyDerError::ExportingNonRsaPssPrivateKeyAsPkcs8Unsupported)
           }
           AsymmetricPrivateKey::Dsa(key) => {
             let document = key
               .to_pkcs8_der()
-              .map_err(|_| type_error("invalid DSA private key"))?;
+              .map_err(|_| AsymmetricPrivateKeyDerError::InvalidDsaPrivateKey)?;
             document.to_bytes().to_vec().into_boxed_slice()
           }
           AsymmetricPrivateKey::Ec(key) => {
@@ -1148,14 +1383,14 @@ impl AsymmetricPrivateKey {
               EcPrivateKey::P256(key) => key.to_pkcs8_der(),
               EcPrivateKey::P384(key) => key.to_pkcs8_der(),
             }
-            .map_err(|_| type_error("invalid EC private key"))?;
+            .map_err(|_| AsymmetricPrivateKeyDerError::InvalidEcPrivateKey)?;
             document.to_bytes().to_vec().into_boxed_slice()
           }
           AsymmetricPrivateKey::X25519(key) => {
             let private_key = OctetStringRef::new(key.as_bytes())
-              .map_err(|_| type_error("invalid X25519 private key"))?
+              .map_err(|_| AsymmetricPrivateKeyDerError::InvalidX25519PrivateKey)?
               .to_der()
-              .map_err(|_| type_error("invalid X25519 private key"))?;
+              .map_err(|_| AsymmetricPrivateKeyDerError::InvalidX25519PrivateKey)?;
 
             let private_key = PrivateKeyInfo {
               algorithm: rsa::pkcs8::AlgorithmIdentifierRef {
@@ -1168,15 +1403,15 @@ impl AsymmetricPrivateKey {
 
             let der = private_key
               .to_der()
-              .map_err(|_| type_error("invalid X25519 private key"))?
+              .map_err(|_| AsymmetricPrivateKeyDerError::InvalidX25519PrivateKey)?
               .into_boxed_slice();
             return Ok(der);
           }
           AsymmetricPrivateKey::Ed25519(key) => {
             let private_key = OctetStringRef::new(key.as_bytes())
-              .map_err(|_| type_error("invalid Ed25519 private key"))?
+              .map_err(|_| AsymmetricPrivateKeyDerError::InvalidEd25519PrivateKey)?
               .to_der()
-              .map_err(|_| type_error("invalid Ed25519 private key"))?;
+              .map_err(|_| AsymmetricPrivateKeyDerError::InvalidEd25519PrivateKey)?;
 
             let private_key = PrivateKeyInfo {
               algorithm: rsa::pkcs8::AlgorithmIdentifierRef {
@@ -1189,7 +1424,7 @@ impl AsymmetricPrivateKey {
 
             private_key
               .to_der()
-              .map_err(|_| type_error("invalid ED25519 private key"))?
+              .map_err(|_| AsymmetricPrivateKeyDerError::InvalidEd25519PrivateKey)?
               .into_boxed_slice()
           }
           AsymmetricPrivateKey::Dh(key) => {
@@ -1206,14 +1441,14 @@ impl AsymmetricPrivateKey {
 
             private_key
               .to_der()
-              .map_err(|_| type_error("invalid DH private key"))?
+              .map_err(|_| AsymmetricPrivateKeyDerError::InvalidDhPrivateKey)?
               .into_boxed_slice()
           }
         };
 
         Ok(der)
       }
-      _ => Err(type_error(format!("unsupported key type: {}", typ))),
+      _ => Err(AsymmetricPrivateKeyDerError::UnsupportedKeyType(typ.to_string())),
     }
   }
 }
@@ -1225,7 +1460,7 @@ pub fn op_node_create_private_key(
   #[string] format: &str,
   #[string] typ: &str,
   #[buffer] passphrase: Option<&[u8]>,
-) -> Result<KeyObjectHandle, AnyError> {
+) -> Result<KeyObjectHandle, AsymmetricPrivateKeyError> {
   KeyObjectHandle::new_asymmetric_private_key_from_js(
     key, format, typ, passphrase,
   )
@@ -1237,7 +1472,7 @@ pub fn op_node_create_ed_raw(
   #[string] curve: &str,
   #[buffer] key: &[u8],
   is_public: bool,
-) -> Result<KeyObjectHandle, AnyError> {
+) -> Result<KeyObjectHandle, EdRawError> {
   KeyObjectHandle::new_ed_raw(curve, key, is_public)
 }
 
@@ -1255,16 +1490,16 @@ pub struct RsaJwkKey {
 pub fn op_node_create_rsa_jwk(
   #[serde] jwk: RsaJwkKey,
   is_public: bool,
-) -> Result<KeyObjectHandle, AnyError> {
+) -> Result<KeyObjectHandle, RsaJwkError> {
   KeyObjectHandle::new_rsa_jwk(jwk, is_public)
 }
 
 #[op2]
 #[cppgc]
 pub fn op_node_create_ec_jwk(
-  #[serde] jwk: elliptic_curve::JwkEcKey,
+  #[serde] jwk: JwkEcKey,
   is_public: bool,
-) -> Result<KeyObjectHandle, AnyError> {
+) -> Result<KeyObjectHandle, EcJwkError> {
   KeyObjectHandle::new_ec_jwk(&jwk, is_public)
 }
 
@@ -1275,7 +1510,7 @@ pub fn op_node_create_public_key(
   #[string] format: &str,
   #[string] typ: &str,
   #[buffer] passphrase: Option<&[u8]>,
-) -> Result<KeyObjectHandle, AnyError> {
+) -> Result<KeyObjectHandle, AsymmetricPublicKeyError> {
   KeyObjectHandle::new_asymmetric_public_key_from_js(
     key, format, typ, passphrase,
   )
@@ -1293,7 +1528,7 @@ pub fn op_node_create_secret_key(
 #[string]
 pub fn op_node_get_asymmetric_key_type(
   #[cppgc] handle: &KeyObjectHandle,
-) -> Result<&'static str, AnyError> {
+) -> Result<&'static str, deno_core::error::AnyError> {
   match handle {
     KeyObjectHandle::AsymmetricPrivate(AsymmetricPrivateKey::Rsa(_))
     | KeyObjectHandle::AsymmetricPublic(AsymmetricPublicKey::Rsa(_)) => {
@@ -1364,7 +1599,7 @@ pub enum AsymmetricKeyDetails {
 #[serde]
 pub fn op_node_get_asymmetric_key_details(
   #[cppgc] handle: &KeyObjectHandle,
-) -> Result<AsymmetricKeyDetails, AnyError> {
+) -> Result<AsymmetricKeyDetails, deno_core::error::AnyError> {
   match handle {
     KeyObjectHandle::AsymmetricPrivate(private_key) => match private_key {
       AsymmetricPrivateKey::Rsa(key) => {
@@ -1482,12 +1717,10 @@ pub fn op_node_get_asymmetric_key_details(
 #[smi]
 pub fn op_node_get_symmetric_key_size(
   #[cppgc] handle: &KeyObjectHandle,
-) -> Result<usize, AnyError> {
+) -> Result<usize, deno_core::error::AnyError> {
   match handle {
-    KeyObjectHandle::AsymmetricPrivate(_) => {
-      Err(type_error("asymmetric key is not a symmetric key"))
-    }
-    KeyObjectHandle::AsymmetricPublic(_) => {
+    KeyObjectHandle::AsymmetricPrivate(_)
+    | KeyObjectHandle::AsymmetricPublic(_) => {
       Err(type_error("asymmetric key is not a symmetric key"))
     }
     KeyObjectHandle::Secret(key) => Ok(key.len() * 8),
@@ -1592,13 +1825,17 @@ pub async fn op_node_generate_rsa_key_async(
     .unwrap()
 }
 
+#[derive(Debug, thiserror::Error)]
+#[error("digest not allowed for RSA-PSS keys{}", .0.as_ref().map(|digest| format!(": {digest}")).unwrap_or_default())]
+pub struct GenerateRsaPssError(Option<String>);
+
 fn generate_rsa_pss(
   modulus_length: usize,
   public_exponent: usize,
   hash_algorithm: Option<&str>,
   mf1_hash_algorithm: Option<&str>,
   salt_length: Option<u32>,
-) -> Result<KeyObjectHandlePair, AnyError> {
+) -> Result<KeyObjectHandlePair, GenerateRsaPssError> {
   let key = RsaPrivateKey::new_with_exp(
     &mut thread_rng(),
     modulus_length,
@@ -1617,25 +1854,19 @@ fn generate_rsa_pss(
     let hash_algorithm = match_fixed_digest_with_oid!(
       hash_algorithm,
       fn (algorithm: Option<RsaPssHashAlgorithm>) {
-        algorithm.ok_or_else(|| type_error("digest not allowed for RSA-PSS keys: {}"))?
+        algorithm.ok_or(GenerateRsaPssError(None))?
       },
       _ => {
-        return Err(type_error(format!(
-          "digest not allowed for RSA-PSS keys: {}",
-          hash_algorithm
-        )))
+        return Err(GenerateRsaPssError(Some(hash_algorithm.to_string())))
       }
     );
     let mf1_hash_algorithm = match_fixed_digest_with_oid!(
       mf1_hash_algorithm,
       fn (algorithm: Option<RsaPssHashAlgorithm>) {
-        algorithm.ok_or_else(|| type_error("digest not allowed for RSA-PSS keys: {}"))?
+        algorithm.ok_or(GenerateRsaPssError(None))?
       },
       _ => {
-        return Err(type_error(format!(
-          "digest not allowed for RSA-PSS keys: {}",
-          mf1_hash_algorithm
-        )))
+        return Err(GenerateRsaPssError(Some(mf1_hash_algorithm.to_string())))
       }
     );
     let salt_length =
@@ -1663,7 +1894,7 @@ pub fn op_node_generate_rsa_pss_key(
   #[string] hash_algorithm: Option<String>, // todo: Option<&str> not supproted in ops yet
   #[string] mf1_hash_algorithm: Option<String>, // todo: Option<&str> not supproted in ops yet
   #[smi] salt_length: Option<u32>,
-) -> Result<KeyObjectHandlePair, AnyError> {
+) -> Result<KeyObjectHandlePair, GenerateRsaPssError> {
   generate_rsa_pss(
     modulus_length,
     public_exponent,
@@ -1681,7 +1912,7 @@ pub async fn op_node_generate_rsa_pss_key_async(
   #[string] hash_algorithm: Option<String>, // todo: Option<&str> not supproted in ops yet
   #[string] mf1_hash_algorithm: Option<String>, // todo: Option<&str> not supproted in ops yet
   #[smi] salt_length: Option<u32>,
-) -> Result<KeyObjectHandlePair, AnyError> {
+) -> Result<KeyObjectHandlePair, GenerateRsaPssError> {
   spawn_blocking(move || {
     generate_rsa_pss(
       modulus_length,
@@ -1698,7 +1929,7 @@ pub async fn op_node_generate_rsa_pss_key_async(
 fn dsa_generate(
   modulus_length: usize,
   divisor_length: usize,
-) -> Result<KeyObjectHandlePair, AnyError> {
+) -> Result<KeyObjectHandlePair, deno_core::error::AnyError> {
   let mut rng = rand::thread_rng();
   use dsa::Components;
   use dsa::KeySize;
@@ -1729,7 +1960,7 @@ fn dsa_generate(
 pub fn op_node_generate_dsa_key(
   #[smi] modulus_length: usize,
   #[smi] divisor_length: usize,
-) -> Result<KeyObjectHandlePair, AnyError> {
+) -> Result<KeyObjectHandlePair, deno_core::error::AnyError> {
   dsa_generate(modulus_length, divisor_length)
 }
 
@@ -1738,13 +1969,15 @@ pub fn op_node_generate_dsa_key(
 pub async fn op_node_generate_dsa_key_async(
   #[smi] modulus_length: usize,
   #[smi] divisor_length: usize,
-) -> Result<KeyObjectHandlePair, AnyError> {
+) -> Result<KeyObjectHandlePair, deno_core::error::AnyError> {
   spawn_blocking(move || dsa_generate(modulus_length, divisor_length))
     .await
     .unwrap()
 }
 
-fn ec_generate(named_curve: &str) -> Result<KeyObjectHandlePair, AnyError> {
+fn ec_generate(
+  named_curve: &str,
+) -> Result<KeyObjectHandlePair, deno_core::error::AnyError> {
   let mut rng = rand::thread_rng();
   // TODO(@littledivy): Support public key point encoding.
   // Default is uncompressed.
@@ -1776,7 +2009,7 @@ fn ec_generate(named_curve: &str) -> Result<KeyObjectHandlePair, AnyError> {
 #[cppgc]
 pub fn op_node_generate_ec_key(
   #[string] named_curve: &str,
-) -> Result<KeyObjectHandlePair, AnyError> {
+) -> Result<KeyObjectHandlePair, deno_core::error::AnyError> {
   ec_generate(named_curve)
 }
 
@@ -1784,7 +2017,7 @@ pub fn op_node_generate_ec_key(
 #[cppgc]
 pub async fn op_node_generate_ec_key_async(
   #[string] named_curve: String,
-) -> Result<KeyObjectHandlePair, AnyError> {
+) -> Result<KeyObjectHandlePair, deno_core::error::AnyError> {
   spawn_blocking(move || ec_generate(&named_curve))
     .await
     .unwrap()
@@ -1840,7 +2073,7 @@ fn u32_slice_to_u8_slice(slice: &[u32]) -> &[u8] {
 
 fn dh_group_generate(
   group_name: &str,
-) -> Result<KeyObjectHandlePair, AnyError> {
+) -> Result<KeyObjectHandlePair, deno_core::error::AnyError> {
   let (dh, prime, generator) = match group_name {
     "modp5" => (
       dh::DiffieHellman::group::<dh::Modp1536>(),
@@ -1895,7 +2128,7 @@ fn dh_group_generate(
 #[cppgc]
 pub fn op_node_generate_dh_group_key(
   #[string] group_name: &str,
-) -> Result<KeyObjectHandlePair, AnyError> {
+) -> Result<KeyObjectHandlePair, deno_core::error::AnyError> {
   dh_group_generate(group_name)
 }
 
@@ -1903,7 +2136,7 @@ pub fn op_node_generate_dh_group_key(
 #[cppgc]
 pub async fn op_node_generate_dh_group_key_async(
   #[string] group_name: String,
-) -> Result<KeyObjectHandlePair, AnyError> {
+) -> Result<KeyObjectHandlePair, deno_core::error::AnyError> {
   spawn_blocking(move || dh_group_generate(&group_name))
     .await
     .unwrap()
@@ -1913,7 +2146,7 @@ fn dh_generate(
   prime: Option<&[u8]>,
   prime_len: usize,
   generator: usize,
-) -> Result<KeyObjectHandlePair, AnyError> {
+) -> KeyObjectHandlePair {
   let prime = prime
     .map(|p| p.into())
     .unwrap_or_else(|| Prime::generate(prime_len));
@@ -1923,7 +2156,7 @@ fn dh_generate(
     base: asn1::Int::new(generator.to_be_bytes().as_slice()).unwrap(),
     private_value_length: None,
   };
-  Ok(KeyObjectHandlePair::new(
+  KeyObjectHandlePair::new(
     AsymmetricPrivateKey::Dh(DhPrivateKey {
       key: dh.private_key,
       params: params.clone(),
@@ -1932,7 +2165,7 @@ fn dh_generate(
       key: dh.public_key,
       params,
     }),
-  ))
+  )
 }
 
 #[op2]
@@ -1941,7 +2174,7 @@ pub fn op_node_generate_dh_key(
   #[buffer] prime: Option<&[u8]>,
   #[smi] prime_len: usize,
   #[smi] generator: usize,
-) -> Result<KeyObjectHandlePair, AnyError> {
+) -> KeyObjectHandlePair {
   dh_generate(prime, prime_len, generator)
 }
 
@@ -1951,7 +2184,7 @@ pub async fn op_node_generate_dh_key_async(
   #[buffer(copy)] prime: Option<Box<[u8]>>,
   #[smi] prime_len: usize,
   #[smi] generator: usize,
-) -> Result<KeyObjectHandlePair, AnyError> {
+) -> KeyObjectHandlePair {
   spawn_blocking(move || dh_generate(prime.as_deref(), prime_len, generator))
     .await
     .unwrap()
@@ -1963,21 +2196,21 @@ pub fn op_node_dh_keys_generate_and_export(
   #[buffer] prime: Option<&[u8]>,
   #[smi] prime_len: usize,
   #[smi] generator: usize,
-) -> Result<(ToJsBuffer, ToJsBuffer), AnyError> {
+) -> (ToJsBuffer, ToJsBuffer) {
   let prime = prime
     .map(|p| p.into())
     .unwrap_or_else(|| Prime::generate(prime_len));
   let dh = dh::DiffieHellman::new(prime, generator);
   let private_key = dh.private_key.into_vec().into_boxed_slice();
   let public_key = dh.public_key.into_vec().into_boxed_slice();
-  Ok((private_key.into(), public_key.into()))
+  (private_key.into(), public_key.into())
 }
 
 #[op2]
 #[buffer]
 pub fn op_node_export_secret_key(
   #[cppgc] handle: &KeyObjectHandle,
-) -> Result<Box<[u8]>, AnyError> {
+) -> Result<Box<[u8]>, deno_core::error::AnyError> {
   let key = handle
     .as_secret_key()
     .ok_or_else(|| type_error("key is not a secret key"))?;
@@ -1988,7 +2221,7 @@ pub fn op_node_export_secret_key(
 #[string]
 pub fn op_node_export_secret_key_b64url(
   #[cppgc] handle: &KeyObjectHandle,
-) -> Result<String, AnyError> {
+) -> Result<String, deno_core::error::AnyError> {
   let key = handle
     .as_secret_key()
     .ok_or_else(|| type_error("key is not a secret key"))?;
@@ -1999,23 +2232,33 @@ pub fn op_node_export_secret_key_b64url(
 #[serde]
 pub fn op_node_export_public_key_jwk(
   #[cppgc] handle: &KeyObjectHandle,
-) -> Result<deno_core::serde_json::Value, AnyError> {
+) -> Result<deno_core::serde_json::Value, AsymmetricPublicKeyJwkError> {
   let public_key = handle
     .as_public_key()
-    .ok_or_else(|| type_error("key is not an asymmetric public key"))?;
+    .ok_or(AsymmetricPublicKeyJwkError::KeyIsNotAsymmetricPublicKey)?;
 
   public_key.export_jwk()
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum ExportPublicKeyPemError {
+  #[error(transparent)]
+  AsymmetricPublicKeyDer(#[from] AsymmetricPublicKeyDerError),
+  #[error("very large data")]
+  VeryLargeData,
+  #[error(transparent)]
+  Der(#[from] der::Error),
+}
+
 #[op2]
 #[string]
 pub fn op_node_export_public_key_pem(
   #[cppgc] handle: &KeyObjectHandle,
   #[string] typ: &str,
-) -> Result<String, AnyError> {
+) -> Result<String, ExportPublicKeyPemError> {
   let public_key = handle
     .as_public_key()
-    .ok_or_else(|| type_error("key is not an asymmetric public key"))?;
+    .ok_or(AsymmetricPublicKeyDerError::KeyIsNotAsymmetricPublicKey)?;
   let data = public_key.export_der(typ)?;
 
   let label = match typ {
@@ -2024,7 +2267,9 @@ pub fn op_node_export_public_key_pem(
     _ => unreachable!("export_der would have errored"),
   };
 
-  let mut out = vec![0; 2048];
+  let pem_len = der::pem::encapsulated_len(label, LineEnding::LF, data.len())
+    .map_err(|_| ExportPublicKeyPemError::VeryLargeData)?;
+  let mut out = vec![0; pem_len];
   let mut writer = PemWriter::new(label, LineEnding::LF, &mut out)?;
   writer.write(&data)?;
   let len = writer.finish()?;
@@ -2038,22 +2283,32 @@ pub fn op_node_export_public_key_pem(
 pub fn op_node_export_public_key_der(
   #[cppgc] handle: &KeyObjectHandle,
   #[string] typ: &str,
-) -> Result<Box<[u8]>, AnyError> {
+) -> Result<Box<[u8]>, AsymmetricPublicKeyDerError> {
   let public_key = handle
     .as_public_key()
-    .ok_or_else(|| type_error("key is not an asymmetric public key"))?;
+    .ok_or(AsymmetricPublicKeyDerError::KeyIsNotAsymmetricPublicKey)?;
   public_key.export_der(typ)
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum ExportPrivateKeyPemError {
+  #[error(transparent)]
+  AsymmetricPublicKeyDer(#[from] AsymmetricPrivateKeyDerError),
+  #[error("very large data")]
+  VeryLargeData,
+  #[error(transparent)]
+  Der(#[from] der::Error),
+}
+
 #[op2]
 #[string]
 pub fn op_node_export_private_key_pem(
   #[cppgc] handle: &KeyObjectHandle,
   #[string] typ: &str,
-) -> Result<String, AnyError> {
+) -> Result<String, ExportPrivateKeyPemError> {
   let private_key = handle
     .as_private_key()
-    .ok_or_else(|| type_error("key is not an asymmetric private key"))?;
+    .ok_or(AsymmetricPrivateKeyDerError::KeyIsNotAsymmetricPrivateKey)?;
   let data = private_key.export_der(typ)?;
 
   let label = match typ {
@@ -2063,7 +2318,9 @@ pub fn op_node_export_private_key_pem(
     _ => unreachable!("export_der would have errored"),
   };
 
-  let mut out = vec![0; 2048];
+  let pem_len = der::pem::encapsulated_len(label, LineEnding::LF, data.len())
+    .map_err(|_| ExportPrivateKeyPemError::VeryLargeData)?;
+  let mut out = vec![0; pem_len];
   let mut writer = PemWriter::new(label, LineEnding::LF, &mut out)?;
   writer.write(&data)?;
   let len = writer.finish()?;
@@ -2077,10 +2334,10 @@ pub fn op_node_export_private_key_pem(
 pub fn op_node_export_private_key_der(
   #[cppgc] handle: &KeyObjectHandle,
   #[string] typ: &str,
-) -> Result<Box<[u8]>, AnyError> {
+) -> Result<Box<[u8]>, AsymmetricPrivateKeyDerError> {
   let private_key = handle
     .as_private_key()
-    .ok_or_else(|| type_error("key is not an asymmetric private key"))?;
+    .ok_or(AsymmetricPrivateKeyDerError::KeyIsNotAsymmetricPrivateKey)?;
   private_key.export_der(typ)
 }
 
@@ -2098,7 +2355,7 @@ pub fn op_node_key_type(#[cppgc] handle: &KeyObjectHandle) -> &'static str {
 #[cppgc]
 pub fn op_node_derive_public_key_from_private_key(
   #[cppgc] handle: &KeyObjectHandle,
-) -> Result<KeyObjectHandle, AnyError> {
+) -> Result<KeyObjectHandle, deno_core::error::AnyError> {
   let Some(private_key) = handle.as_private_key() else {
     return Err(type_error("expected private key"));
   };
diff --git a/ext/node/ops/crypto/mod.rs b/ext/node/ops/crypto/mod.rs
index 600d315587..e90e820909 100644
--- a/ext/node/ops/crypto/mod.rs
+++ b/ext/node/ops/crypto/mod.rs
@@ -1,7 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 use deno_core::error::generic_error;
 use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::unsync::spawn_blocking;
 use deno_core::JsBuffer;
@@ -34,14 +33,14 @@ use rsa::Pkcs1v15Encrypt;
 use rsa::RsaPrivateKey;
 use rsa::RsaPublicKey;
 
-mod cipher;
+pub mod cipher;
 mod dh;
-mod digest;
+pub mod digest;
 pub mod keys;
 mod md5_sha1;
 mod pkcs3;
 mod primes;
-mod sign;
+pub mod sign;
 pub mod x509;
 
 use self::digest::match_fixed_digest_with_eager_block_buffer;
@@ -58,38 +57,31 @@ pub fn op_node_check_prime(
 pub fn op_node_check_prime_bytes(
   #[anybuffer] bytes: &[u8],
   #[number] checks: usize,
-) -> Result<bool, AnyError> {
+) -> bool {
   let candidate = BigInt::from_bytes_be(num_bigint::Sign::Plus, bytes);
-  Ok(primes::is_probably_prime(&candidate, checks))
+  primes::is_probably_prime(&candidate, checks)
 }
 
 #[op2(async)]
 pub async fn op_node_check_prime_async(
   #[bigint] num: i64,
   #[number] checks: usize,
-) -> Result<bool, AnyError> {
+) -> Result<bool, tokio::task::JoinError> {
   // TODO(@littledivy): use rayon for CPU-bound tasks
-  Ok(
-    spawn_blocking(move || {
-      primes::is_probably_prime(&BigInt::from(num), checks)
-    })
-    .await?,
-  )
+  spawn_blocking(move || primes::is_probably_prime(&BigInt::from(num), checks))
+    .await
 }
 
 #[op2(async)]
 pub fn op_node_check_prime_bytes_async(
   #[anybuffer] bytes: &[u8],
   #[number] checks: usize,
-) -> Result<impl Future<Output = Result<bool, AnyError>>, AnyError> {
+) -> impl Future<Output = Result<bool, tokio::task::JoinError>> {
   let candidate = BigInt::from_bytes_be(num_bigint::Sign::Plus, bytes);
   // TODO(@littledivy): use rayon for CPU-bound tasks
-  Ok(async move {
-    Ok(
-      spawn_blocking(move || primes::is_probably_prime(&candidate, checks))
-        .await?,
-    )
-  })
+  async move {
+    spawn_blocking(move || primes::is_probably_prime(&candidate, checks)).await
+  }
 }
 
 #[op2]
@@ -97,7 +89,7 @@ pub fn op_node_check_prime_bytes_async(
 pub fn op_node_create_hash(
   #[string] algorithm: &str,
   output_length: Option<u32>,
-) -> Result<digest::Hasher, AnyError> {
+) -> Result<digest::Hasher, digest::HashError> {
   digest::Hasher::new(algorithm, output_length.map(|l| l as usize))
 }
 
@@ -145,17 +137,31 @@ pub fn op_node_hash_digest_hex(
 pub fn op_node_hash_clone(
   #[cppgc] hasher: &digest::Hasher,
   output_length: Option<u32>,
-) -> Result<Option<digest::Hasher>, AnyError> {
+) -> Result<Option<digest::Hasher>, digest::HashError> {
   hasher.clone_inner(output_length.map(|l| l as usize))
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum PrivateEncryptDecryptError {
+  #[error(transparent)]
+  Pkcs8(#[from] pkcs8::Error),
+  #[error(transparent)]
+  Spki(#[from] spki::Error),
+  #[error(transparent)]
+  Utf8(#[from] std::str::Utf8Error),
+  #[error(transparent)]
+  Rsa(#[from] rsa::Error),
+  #[error("Unknown padding")]
+  UnknownPadding,
+}
+
 #[op2]
 #[serde]
 pub fn op_node_private_encrypt(
   #[serde] key: StringOrBuffer,
   #[serde] msg: StringOrBuffer,
   #[smi] padding: u32,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, PrivateEncryptDecryptError> {
   let key = RsaPrivateKey::from_pkcs8_pem((&key).try_into()?)?;
 
   let mut rng = rand::thread_rng();
@@ -172,7 +178,7 @@ pub fn op_node_private_encrypt(
         .encrypt(&mut rng, Oaep::new::<sha1::Sha1>(), &msg)?
         .into(),
     ),
-    _ => Err(type_error("Unknown padding")),
+    _ => Err(PrivateEncryptDecryptError::UnknownPadding),
   }
 }
 
@@ -182,13 +188,13 @@ pub fn op_node_private_decrypt(
   #[serde] key: StringOrBuffer,
   #[serde] msg: StringOrBuffer,
   #[smi] padding: u32,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, PrivateEncryptDecryptError> {
   let key = RsaPrivateKey::from_pkcs8_pem((&key).try_into()?)?;
 
   match padding {
     1 => Ok(key.decrypt(Pkcs1v15Encrypt, &msg)?.into()),
     4 => Ok(key.decrypt(Oaep::new::<sha1::Sha1>(), &msg)?.into()),
-    _ => Err(type_error("Unknown padding")),
+    _ => Err(PrivateEncryptDecryptError::UnknownPadding),
   }
 }
 
@@ -198,7 +204,7 @@ pub fn op_node_public_encrypt(
   #[serde] key: StringOrBuffer,
   #[serde] msg: StringOrBuffer,
   #[smi] padding: u32,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, PrivateEncryptDecryptError> {
   let key = RsaPublicKey::from_public_key_pem((&key).try_into()?)?;
 
   let mut rng = rand::thread_rng();
@@ -209,7 +215,7 @@ pub fn op_node_public_encrypt(
         .encrypt(&mut rng, Oaep::new::<sha1::Sha1>(), &msg)?
         .into(),
     ),
-    _ => Err(type_error("Unknown padding")),
+    _ => Err(PrivateEncryptDecryptError::UnknownPadding),
   }
 }
 
@@ -220,7 +226,7 @@ pub fn op_node_create_cipheriv(
   #[string] algorithm: &str,
   #[buffer] key: &[u8],
   #[buffer] iv: &[u8],
-) -> Result<u32, AnyError> {
+) -> Result<u32, cipher::CipherContextError> {
   let context = cipher::CipherContext::new(algorithm, key, iv)?;
   Ok(state.resource_table.add(context))
 }
@@ -262,11 +268,14 @@ pub fn op_node_cipheriv_final(
   auto_pad: bool,
   #[buffer] input: &[u8],
   #[anybuffer] output: &mut [u8],
-) -> Result<Option<Vec<u8>>, AnyError> {
-  let context = state.resource_table.take::<cipher::CipherContext>(rid)?;
+) -> Result<Option<Vec<u8>>, cipher::CipherContextError> {
+  let context = state
+    .resource_table
+    .take::<cipher::CipherContext>(rid)
+    .map_err(cipher::CipherContextError::Resource)?;
   let context = Rc::try_unwrap(context)
-    .map_err(|_| type_error("Cipher context is already in use"))?;
-  context.r#final(auto_pad, input, output)
+    .map_err(|_| cipher::CipherContextError::ContextInUse)?;
+  context.r#final(auto_pad, input, output).map_err(Into::into)
 }
 
 #[op2]
@@ -274,10 +283,13 @@ pub fn op_node_cipheriv_final(
 pub fn op_node_cipheriv_take(
   state: &mut OpState,
   #[smi] rid: u32,
-) -> Result<Option<Vec<u8>>, AnyError> {
-  let context = state.resource_table.take::<cipher::CipherContext>(rid)?;
+) -> Result<Option<Vec<u8>>, cipher::CipherContextError> {
+  let context = state
+    .resource_table
+    .take::<cipher::CipherContext>(rid)
+    .map_err(cipher::CipherContextError::Resource)?;
   let context = Rc::try_unwrap(context)
-    .map_err(|_| type_error("Cipher context is already in use"))?;
+    .map_err(|_| cipher::CipherContextError::ContextInUse)?;
   Ok(context.take_tag())
 }
 
@@ -288,7 +300,7 @@ pub fn op_node_create_decipheriv(
   #[string] algorithm: &str,
   #[buffer] key: &[u8],
   #[buffer] iv: &[u8],
-) -> Result<u32, AnyError> {
+) -> Result<u32, cipher::DecipherContextError> {
   let context = cipher::DecipherContext::new(algorithm, key, iv)?;
   Ok(state.resource_table.add(context))
 }
@@ -326,10 +338,13 @@ pub fn op_node_decipheriv_decrypt(
 pub fn op_node_decipheriv_take(
   state: &mut OpState,
   #[smi] rid: u32,
-) -> Result<(), AnyError> {
-  let context = state.resource_table.take::<cipher::DecipherContext>(rid)?;
+) -> Result<(), cipher::DecipherContextError> {
+  let context = state
+    .resource_table
+    .take::<cipher::DecipherContext>(rid)
+    .map_err(cipher::DecipherContextError::Resource)?;
   Rc::try_unwrap(context)
-    .map_err(|_| type_error("Cipher context is already in use"))?;
+    .map_err(|_| cipher::DecipherContextError::ContextInUse)?;
   Ok(())
 }
 
@@ -341,11 +356,16 @@ pub fn op_node_decipheriv_final(
   #[buffer] input: &[u8],
   #[anybuffer] output: &mut [u8],
   #[buffer] auth_tag: &[u8],
-) -> Result<(), AnyError> {
-  let context = state.resource_table.take::<cipher::DecipherContext>(rid)?;
+) -> Result<(), cipher::DecipherContextError> {
+  let context = state
+    .resource_table
+    .take::<cipher::DecipherContext>(rid)
+    .map_err(cipher::DecipherContextError::Resource)?;
   let context = Rc::try_unwrap(context)
-    .map_err(|_| type_error("Cipher context is already in use"))?;
-  context.r#final(auto_pad, input, output, auth_tag)
+    .map_err(|_| cipher::DecipherContextError::ContextInUse)?;
+  context
+    .r#final(auto_pad, input, output, auth_tag)
+    .map_err(Into::into)
 }
 
 #[op2]
@@ -356,7 +376,7 @@ pub fn op_node_sign(
   #[string] digest_type: &str,
   #[smi] pss_salt_length: Option<u32>,
   #[smi] dsa_signature_encoding: u32,
-) -> Result<Box<[u8]>, AnyError> {
+) -> Result<Box<[u8]>, sign::KeyObjectHandlePrehashedSignAndVerifyError> {
   handle.sign_prehashed(
     digest_type,
     digest,
@@ -373,7 +393,7 @@ pub fn op_node_verify(
   #[buffer] signature: &[u8],
   #[smi] pss_salt_length: Option<u32>,
   #[smi] dsa_signature_encoding: u32,
-) -> Result<bool, AnyError> {
+) -> Result<bool, sign::KeyObjectHandlePrehashedSignAndVerifyError> {
   handle.verify_prehashed(
     digest_type,
     digest,
@@ -383,13 +403,21 @@ pub fn op_node_verify(
   )
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum Pbkdf2Error {
+  #[error("unsupported digest: {0}")]
+  UnsupportedDigest(String),
+  #[error(transparent)]
+  Join(#[from] tokio::task::JoinError),
+}
+
 fn pbkdf2_sync(
   password: &[u8],
   salt: &[u8],
   iterations: u32,
   algorithm_name: &str,
   derived_key: &mut [u8],
-) -> Result<(), AnyError> {
+) -> Result<(), Pbkdf2Error> {
   match_fixed_digest_with_eager_block_buffer!(
     algorithm_name,
     fn <D>() {
@@ -397,10 +425,7 @@ fn pbkdf2_sync(
       Ok(())
     },
     _ => {
-      Err(type_error(format!(
-        "unsupported digest: {}",
-        algorithm_name
-      )))
+      Err(Pbkdf2Error::UnsupportedDigest(algorithm_name.to_string()))
     }
   )
 }
@@ -424,7 +449,7 @@ pub async fn op_node_pbkdf2_async(
   #[smi] iterations: u32,
   #[string] digest: String,
   #[number] keylen: usize,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, Pbkdf2Error> {
   spawn_blocking(move || {
     let mut derived_key = vec![0; keylen];
     pbkdf2_sync(&password, &salt, iterations, &digest, &mut derived_key)
@@ -450,15 +475,27 @@ pub async fn op_node_fill_random_async(#[smi] len: i32) -> ToJsBuffer {
   .unwrap()
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum HkdfError {
+  #[error("expected secret key")]
+  ExpectedSecretKey,
+  #[error("HKDF-Expand failed")]
+  HkdfExpandFailed,
+  #[error("Unsupported digest: {0}")]
+  UnsupportedDigest(String),
+  #[error(transparent)]
+  Join(#[from] tokio::task::JoinError),
+}
+
 fn hkdf_sync(
   digest_algorithm: &str,
   handle: &KeyObjectHandle,
   salt: &[u8],
   info: &[u8],
   okm: &mut [u8],
-) -> Result<(), AnyError> {
+) -> Result<(), HkdfError> {
   let Some(ikm) = handle.as_secret_key() else {
-    return Err(type_error("expected secret key"));
+    return Err(HkdfError::ExpectedSecretKey);
   };
 
   match_fixed_digest_with_eager_block_buffer!(
@@ -466,10 +503,10 @@ fn hkdf_sync(
     fn <D>() {
       let hk = Hkdf::<D>::new(Some(salt), ikm);
       hk.expand(info, okm)
-        .map_err(|_| type_error("HKDF-Expand failed"))
+        .map_err(|_| HkdfError::HkdfExpandFailed)
     },
     _ => {
-      Err(type_error(format!("Unsupported digest: {}", digest_algorithm)))
+      Err(HkdfError::UnsupportedDigest(digest_algorithm.to_string()))
     }
   )
 }
@@ -481,7 +518,7 @@ pub fn op_node_hkdf(
   #[buffer] salt: &[u8],
   #[buffer] info: &[u8],
   #[buffer] okm: &mut [u8],
-) -> Result<(), AnyError> {
+) -> Result<(), HkdfError> {
   hkdf_sync(digest_algorithm, handle, salt, info, okm)
 }
 
@@ -493,7 +530,7 @@ pub async fn op_node_hkdf_async(
   #[buffer] salt: JsBuffer,
   #[buffer] info: JsBuffer,
   #[number] okm_len: usize,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, HkdfError> {
   let handle = handle.clone();
   spawn_blocking(move || {
     let mut okm = vec![0u8; okm_len];
@@ -509,27 +546,24 @@ pub fn op_node_dh_compute_secret(
   #[buffer] prime: JsBuffer,
   #[buffer] private_key: JsBuffer,
   #[buffer] their_public_key: JsBuffer,
-) -> Result<ToJsBuffer, AnyError> {
+) -> ToJsBuffer {
   let pubkey: BigUint = BigUint::from_bytes_be(their_public_key.as_ref());
   let privkey: BigUint = BigUint::from_bytes_be(private_key.as_ref());
   let primei: BigUint = BigUint::from_bytes_be(prime.as_ref());
   let shared_secret: BigUint = pubkey.modpow(&privkey, &primei);
 
-  Ok(shared_secret.to_bytes_be().into())
+  shared_secret.to_bytes_be().into()
 }
 
 #[op2(fast)]
-#[smi]
-pub fn op_node_random_int(
-  #[smi] min: i32,
-  #[smi] max: i32,
-) -> Result<i32, AnyError> {
+#[number]
+pub fn op_node_random_int(#[number] min: i64, #[number] max: i64) -> i64 {
   let mut rng = rand::thread_rng();
   // Uniform distribution is required to avoid Modulo Bias
   // https://en.wikipedia.org/wiki/Fisher–Yates_shuffle#Modulo_bias
   let dist = Uniform::from(min..max);
 
-  Ok(dist.sample(&mut rng))
+  dist.sample(&mut rng)
 }
 
 #[allow(clippy::too_many_arguments)]
@@ -542,7 +576,7 @@ fn scrypt(
   parallelization: u32,
   _maxmem: u32,
   output_buffer: &mut [u8],
-) -> Result<(), AnyError> {
+) -> Result<(), deno_core::error::AnyError> {
   // Construct Params
   let params = scrypt::Params::new(
     cost as u8,
@@ -573,7 +607,7 @@ pub fn op_node_scrypt_sync(
   #[smi] parallelization: u32,
   #[smi] maxmem: u32,
   #[anybuffer] output_buffer: &mut [u8],
-) -> Result<(), AnyError> {
+) -> Result<(), deno_core::error::AnyError> {
   scrypt(
     password,
     salt,
@@ -586,6 +620,14 @@ pub fn op_node_scrypt_sync(
   )
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum ScryptAsyncError {
+  #[error(transparent)]
+  Join(#[from] tokio::task::JoinError),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
 #[op2(async)]
 #[serde]
 pub async fn op_node_scrypt_async(
@@ -596,10 +638,11 @@ pub async fn op_node_scrypt_async(
   #[smi] block_size: u32,
   #[smi] parallelization: u32,
   #[smi] maxmem: u32,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, ScryptAsyncError> {
   spawn_blocking(move || {
     let mut output_buffer = vec![0u8; keylen as usize];
-    let res = scrypt(
+
+    scrypt(
       password,
       salt,
       keylen,
@@ -608,25 +651,30 @@ pub async fn op_node_scrypt_async(
       parallelization,
       maxmem,
       &mut output_buffer,
-    );
-
-    if res.is_ok() {
-      Ok(output_buffer.into())
-    } else {
-      // TODO(lev): rethrow the error?
-      Err(generic_error("scrypt failure"))
-    }
+    )
+    .map(|_| output_buffer.into())
+    .map_err(ScryptAsyncError::Other)
   })
   .await?
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum EcdhEncodePubKey {
+  #[error("Invalid public key")]
+  InvalidPublicKey,
+  #[error("Unsupported curve")]
+  UnsupportedCurve,
+  #[error(transparent)]
+  Sec1(#[from] sec1::Error),
+}
+
 #[op2]
 #[buffer]
 pub fn op_node_ecdh_encode_pubkey(
   #[string] curve: &str,
   #[buffer] pubkey: &[u8],
   compress: bool,
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, EcdhEncodePubKey> {
   use elliptic_curve::sec1::FromEncodedPoint;
 
   match curve {
@@ -639,7 +687,7 @@ pub fn op_node_ecdh_encode_pubkey(
         );
       // CtOption does not expose its variants.
       if pubkey.is_none().into() {
-        return Err(type_error("Invalid public key"));
+        return Err(EcdhEncodePubKey::InvalidPublicKey);
       }
 
       let pubkey = pubkey.unwrap();
@@ -652,7 +700,7 @@ pub fn op_node_ecdh_encode_pubkey(
       );
       // CtOption does not expose its variants.
       if pubkey.is_none().into() {
-        return Err(type_error("Invalid public key"));
+        return Err(EcdhEncodePubKey::InvalidPublicKey);
       }
 
       let pubkey = pubkey.unwrap();
@@ -665,7 +713,7 @@ pub fn op_node_ecdh_encode_pubkey(
       );
       // CtOption does not expose its variants.
       if pubkey.is_none().into() {
-        return Err(type_error("Invalid public key"));
+        return Err(EcdhEncodePubKey::InvalidPublicKey);
       }
 
       let pubkey = pubkey.unwrap();
@@ -678,14 +726,14 @@ pub fn op_node_ecdh_encode_pubkey(
       );
       // CtOption does not expose its variants.
       if pubkey.is_none().into() {
-        return Err(type_error("Invalid public key"));
+        return Err(EcdhEncodePubKey::InvalidPublicKey);
       }
 
       let pubkey = pubkey.unwrap();
 
       Ok(pubkey.to_encoded_point(compress).as_ref().to_vec())
     }
-    &_ => Err(type_error("Unsupported curve")),
+    &_ => Err(EcdhEncodePubKey::UnsupportedCurve),
   }
 }
 
@@ -695,7 +743,7 @@ pub fn op_node_ecdh_generate_keys(
   #[buffer] pubbuf: &mut [u8],
   #[buffer] privbuf: &mut [u8],
   #[string] format: &str,
-) -> Result<(), AnyError> {
+) -> Result<(), deno_core::error::AnyError> {
   let mut rng = rand::thread_rng();
   let compress = format == "compressed";
   match curve {
@@ -742,7 +790,7 @@ pub fn op_node_ecdh_compute_secret(
   #[buffer] this_priv: Option<JsBuffer>,
   #[buffer] their_pub: &mut [u8],
   #[buffer] secret: &mut [u8],
-) -> Result<(), AnyError> {
+) {
   match curve {
     "secp256k1" => {
       let their_public_key =
@@ -760,8 +808,6 @@ pub fn op_node_ecdh_compute_secret(
         their_public_key.as_affine(),
       );
       secret.copy_from_slice(shared_secret.raw_secret_bytes());
-
-      Ok(())
     }
     "prime256v1" | "secp256r1" => {
       let their_public_key =
@@ -776,8 +822,6 @@ pub fn op_node_ecdh_compute_secret(
         their_public_key.as_affine(),
       );
       secret.copy_from_slice(shared_secret.raw_secret_bytes());
-
-      Ok(())
     }
     "secp384r1" => {
       let their_public_key =
@@ -792,8 +836,6 @@ pub fn op_node_ecdh_compute_secret(
         their_public_key.as_affine(),
       );
       secret.copy_from_slice(shared_secret.raw_secret_bytes());
-
-      Ok(())
     }
     "secp224r1" => {
       let their_public_key =
@@ -808,8 +850,6 @@ pub fn op_node_ecdh_compute_secret(
         their_public_key.as_affine(),
       );
       secret.copy_from_slice(shared_secret.raw_secret_bytes());
-
-      Ok(())
     }
     &_ => todo!(),
   }
@@ -820,7 +860,7 @@ pub fn op_node_ecdh_compute_public_key(
   #[string] curve: &str,
   #[buffer] privkey: &[u8],
   #[buffer] pubkey: &mut [u8],
-) -> Result<(), AnyError> {
+) {
   match curve {
     "secp256k1" => {
       let this_private_key =
@@ -828,8 +868,6 @@ pub fn op_node_ecdh_compute_public_key(
           .expect("bad private key");
       let public_key = this_private_key.public_key();
       pubkey.copy_from_slice(public_key.to_sec1_bytes().as_ref());
-
-      Ok(())
     }
     "prime256v1" | "secp256r1" => {
       let this_private_key =
@@ -837,7 +875,6 @@ pub fn op_node_ecdh_compute_public_key(
           .expect("bad private key");
       let public_key = this_private_key.public_key();
       pubkey.copy_from_slice(public_key.to_sec1_bytes().as_ref());
-      Ok(())
     }
     "secp384r1" => {
       let this_private_key =
@@ -845,7 +882,6 @@ pub fn op_node_ecdh_compute_public_key(
           .expect("bad private key");
       let public_key = this_private_key.public_key();
       pubkey.copy_from_slice(public_key.to_sec1_bytes().as_ref());
-      Ok(())
     }
     "secp224r1" => {
       let this_private_key =
@@ -853,7 +889,6 @@ pub fn op_node_ecdh_compute_public_key(
           .expect("bad private key");
       let public_key = this_private_key.public_key();
       pubkey.copy_from_slice(public_key.to_sec1_bytes().as_ref());
-      Ok(())
     }
     &_ => todo!(),
   }
@@ -874,8 +909,20 @@ pub fn op_node_gen_prime(#[number] size: usize) -> ToJsBuffer {
 #[serde]
 pub async fn op_node_gen_prime_async(
   #[number] size: usize,
-) -> Result<ToJsBuffer, AnyError> {
-  Ok(spawn_blocking(move || gen_prime(size)).await?)
+) -> Result<ToJsBuffer, tokio::task::JoinError> {
+  spawn_blocking(move || gen_prime(size)).await
+}
+
+#[derive(Debug, thiserror::Error)]
+pub enum DiffieHellmanError {
+  #[error("Expected private key")]
+  ExpectedPrivateKey,
+  #[error("Expected public key")]
+  ExpectedPublicKey,
+  #[error("DH parameters mismatch")]
+  DhParametersMismatch,
+  #[error("Unsupported key type for diffie hellman, or key type mismatch")]
+  UnsupportedKeyTypeForDiffieHellmanOrKeyTypeMismatch,
 }
 
 #[op2]
@@ -883,117 +930,134 @@ pub async fn op_node_gen_prime_async(
 pub fn op_node_diffie_hellman(
   #[cppgc] private: &KeyObjectHandle,
   #[cppgc] public: &KeyObjectHandle,
-) -> Result<Box<[u8]>, AnyError> {
+) -> Result<Box<[u8]>, DiffieHellmanError> {
   let private = private
     .as_private_key()
-    .ok_or_else(|| type_error("Expected private key"))?;
+    .ok_or(DiffieHellmanError::ExpectedPrivateKey)?;
   let public = public
     .as_public_key()
-    .ok_or_else(|| type_error("Expected public key"))?;
+    .ok_or(DiffieHellmanError::ExpectedPublicKey)?;
 
-  let res = match (private, &*public) {
-    (
-      AsymmetricPrivateKey::Ec(EcPrivateKey::P224(private)),
-      AsymmetricPublicKey::Ec(EcPublicKey::P224(public)),
-    ) => p224::ecdh::diffie_hellman(
-      private.to_nonzero_scalar(),
-      public.as_affine(),
-    )
-    .raw_secret_bytes()
-    .to_vec()
-    .into_boxed_slice(),
-    (
-      AsymmetricPrivateKey::Ec(EcPrivateKey::P256(private)),
-      AsymmetricPublicKey::Ec(EcPublicKey::P256(public)),
-    ) => p256::ecdh::diffie_hellman(
-      private.to_nonzero_scalar(),
-      public.as_affine(),
-    )
-    .raw_secret_bytes()
-    .to_vec()
-    .into_boxed_slice(),
-    (
-      AsymmetricPrivateKey::Ec(EcPrivateKey::P384(private)),
-      AsymmetricPublicKey::Ec(EcPublicKey::P384(public)),
-    ) => p384::ecdh::diffie_hellman(
-      private.to_nonzero_scalar(),
-      public.as_affine(),
-    )
-    .raw_secret_bytes()
-    .to_vec()
-    .into_boxed_slice(),
-    (
-      AsymmetricPrivateKey::X25519(private),
-      AsymmetricPublicKey::X25519(public),
-    ) => private
-      .diffie_hellman(public)
-      .to_bytes()
-      .into_iter()
-      .collect(),
-    (AsymmetricPrivateKey::Dh(private), AsymmetricPublicKey::Dh(public)) => {
-      if private.params.prime != public.params.prime
-        || private.params.base != public.params.base
-      {
-        return Err(type_error("DH parameters mismatch"));
+  let res =
+    match (private, &*public) {
+      (
+        AsymmetricPrivateKey::Ec(EcPrivateKey::P224(private)),
+        AsymmetricPublicKey::Ec(EcPublicKey::P224(public)),
+      ) => p224::ecdh::diffie_hellman(
+        private.to_nonzero_scalar(),
+        public.as_affine(),
+      )
+      .raw_secret_bytes()
+      .to_vec()
+      .into_boxed_slice(),
+      (
+        AsymmetricPrivateKey::Ec(EcPrivateKey::P256(private)),
+        AsymmetricPublicKey::Ec(EcPublicKey::P256(public)),
+      ) => p256::ecdh::diffie_hellman(
+        private.to_nonzero_scalar(),
+        public.as_affine(),
+      )
+      .raw_secret_bytes()
+      .to_vec()
+      .into_boxed_slice(),
+      (
+        AsymmetricPrivateKey::Ec(EcPrivateKey::P384(private)),
+        AsymmetricPublicKey::Ec(EcPublicKey::P384(public)),
+      ) => p384::ecdh::diffie_hellman(
+        private.to_nonzero_scalar(),
+        public.as_affine(),
+      )
+      .raw_secret_bytes()
+      .to_vec()
+      .into_boxed_slice(),
+      (
+        AsymmetricPrivateKey::X25519(private),
+        AsymmetricPublicKey::X25519(public),
+      ) => private
+        .diffie_hellman(public)
+        .to_bytes()
+        .into_iter()
+        .collect(),
+      (AsymmetricPrivateKey::Dh(private), AsymmetricPublicKey::Dh(public)) => {
+        if private.params.prime != public.params.prime
+          || private.params.base != public.params.base
+        {
+          return Err(DiffieHellmanError::DhParametersMismatch);
+        }
+
+        // OSIP - Octet-String-to-Integer primitive
+        let public_key = public.key.clone().into_vec();
+        let pubkey = BigUint::from_bytes_be(&public_key);
+
+        // Exponentiation (z = y^x mod p)
+        let prime = BigUint::from_bytes_be(private.params.prime.as_bytes());
+        let private_key = private.key.clone().into_vec();
+        let private_key = BigUint::from_bytes_be(&private_key);
+        let shared_secret = pubkey.modpow(&private_key, &prime);
+
+        shared_secret.to_bytes_be().into()
       }
-
-      // OSIP - Octet-String-to-Integer primitive
-      let public_key = public.key.clone().into_vec();
-      let pubkey = BigUint::from_bytes_be(&public_key);
-
-      // Exponentiation (z = y^x mod p)
-      let prime = BigUint::from_bytes_be(private.params.prime.as_bytes());
-      let private_key = private.key.clone().into_vec();
-      let private_key = BigUint::from_bytes_be(&private_key);
-      let shared_secret = pubkey.modpow(&private_key, &prime);
-
-      shared_secret.to_bytes_be().into()
-    }
-    _ => {
-      return Err(type_error(
-        "Unsupported key type for diffie hellman, or key type  mismatch",
-      ))
-    }
-  };
+      _ => return Err(
+        DiffieHellmanError::UnsupportedKeyTypeForDiffieHellmanOrKeyTypeMismatch,
+      ),
+    };
 
   Ok(res)
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum SignEd25519Error {
+  #[error("Expected private key")]
+  ExpectedPrivateKey,
+  #[error("Expected Ed25519 private key")]
+  ExpectedEd25519PrivateKey,
+  #[error("Invalid Ed25519 private key")]
+  InvalidEd25519PrivateKey,
+}
+
 #[op2(fast)]
 pub fn op_node_sign_ed25519(
   #[cppgc] key: &KeyObjectHandle,
   #[buffer] data: &[u8],
   #[buffer] signature: &mut [u8],
-) -> Result<(), AnyError> {
+) -> Result<(), SignEd25519Error> {
   let private = key
     .as_private_key()
-    .ok_or_else(|| type_error("Expected private key"))?;
+    .ok_or(SignEd25519Error::ExpectedPrivateKey)?;
 
   let ed25519 = match private {
     AsymmetricPrivateKey::Ed25519(private) => private,
-    _ => return Err(type_error("Expected Ed25519 private key")),
+    _ => return Err(SignEd25519Error::ExpectedEd25519PrivateKey),
   };
 
   let pair = Ed25519KeyPair::from_seed_unchecked(ed25519.as_bytes().as_slice())
-    .map_err(|_| type_error("Invalid Ed25519 private key"))?;
+    .map_err(|_| SignEd25519Error::InvalidEd25519PrivateKey)?;
   signature.copy_from_slice(pair.sign(data).as_ref());
 
   Ok(())
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum VerifyEd25519Error {
+  #[error("Expected public key")]
+  ExpectedPublicKey,
+  #[error("Expected Ed25519 public key")]
+  ExpectedEd25519PublicKey,
+}
+
 #[op2(fast)]
 pub fn op_node_verify_ed25519(
   #[cppgc] key: &KeyObjectHandle,
   #[buffer] data: &[u8],
   #[buffer] signature: &[u8],
-) -> Result<bool, AnyError> {
+) -> Result<bool, VerifyEd25519Error> {
   let public = key
     .as_public_key()
-    .ok_or_else(|| type_error("Expected public key"))?;
+    .ok_or(VerifyEd25519Error::ExpectedPublicKey)?;
 
   let ed25519 = match &*public {
     AsymmetricPublicKey::Ed25519(public) => public,
-    _ => return Err(type_error("Expected Ed25519 public key")),
+    _ => return Err(VerifyEd25519Error::ExpectedEd25519PublicKey),
   };
 
   let verified = ring::signature::UnparsedPublicKey::new(
diff --git a/ext/node/ops/crypto/sign.rs b/ext/node/ops/crypto/sign.rs
index b7779a5d80..30094c0765 100644
--- a/ext/node/ops/crypto/sign.rs
+++ b/ext/node/ops/crypto/sign.rs
@@ -1,7 +1,4 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-use deno_core::error::generic_error;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use rand::rngs::OsRng;
 use rsa::signature::hazmat::PrehashSigner as _;
 use rsa::signature::hazmat::PrehashVerifier as _;
@@ -26,7 +23,7 @@ use elliptic_curve::FieldBytesSize;
 fn dsa_signature<C: elliptic_curve::PrimeCurve>(
   encoding: u32,
   signature: ecdsa::Signature<C>,
-) -> Result<Box<[u8]>, AnyError>
+) -> Result<Box<[u8]>, KeyObjectHandlePrehashedSignAndVerifyError>
 where
   MaxSize<C>: ArrayLength<u8>,
   <FieldBytesSize<C> as Add>::Output: Add<MaxOverhead> + ArrayLength<u8>,
@@ -36,10 +33,54 @@ where
     0 => Ok(signature.to_der().to_bytes().to_vec().into_boxed_slice()),
     // IEEE P1363
     1 => Ok(signature.to_bytes().to_vec().into_boxed_slice()),
-    _ => Err(type_error("invalid DSA signature encoding")),
+    _ => Err(
+      KeyObjectHandlePrehashedSignAndVerifyError::InvalidDsaSignatureEncoding,
+    ),
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum KeyObjectHandlePrehashedSignAndVerifyError {
+  #[error("invalid DSA signature encoding")]
+  InvalidDsaSignatureEncoding,
+  #[error("key is not a private key")]
+  KeyIsNotPrivate,
+  #[error("digest not allowed for RSA signature: {0}")]
+  DigestNotAllowedForRsaSignature(String),
+  #[error("failed to sign digest with RSA")]
+  FailedToSignDigestWithRsa,
+  #[error("digest not allowed for RSA-PSS signature: {0}")]
+  DigestNotAllowedForRsaPssSignature(String),
+  #[error("failed to sign digest with RSA-PSS")]
+  FailedToSignDigestWithRsaPss,
+  #[error("failed to sign digest with DSA")]
+  FailedToSignDigestWithDsa,
+  #[error("rsa-pss with different mf1 hash algorithm and hash algorithm is not supported")]
+  RsaPssHashAlgorithmUnsupported,
+  #[error(
+    "private key does not allow {actual} to be used, expected {expected}"
+  )]
+  PrivateKeyDisallowsUsage { actual: String, expected: String },
+  #[error("failed to sign digest")]
+  FailedToSignDigest,
+  #[error("x25519 key cannot be used for signing")]
+  X25519KeyCannotBeUsedForSigning,
+  #[error("Ed25519 key cannot be used for prehashed signing")]
+  Ed25519KeyCannotBeUsedForPrehashedSigning,
+  #[error("DH key cannot be used for signing")]
+  DhKeyCannotBeUsedForSigning,
+  #[error("key is not a public or private key")]
+  KeyIsNotPublicOrPrivate,
+  #[error("Invalid DSA signature")]
+  InvalidDsaSignature,
+  #[error("x25519 key cannot be used for verification")]
+  X25519KeyCannotBeUsedForVerification,
+  #[error("Ed25519 key cannot be used for prehashed verification")]
+  Ed25519KeyCannotBeUsedForPrehashedVerification,
+  #[error("DH key cannot be used for verification")]
+  DhKeyCannotBeUsedForVerification,
+}
+
 impl KeyObjectHandle {
   pub fn sign_prehashed(
     &self,
@@ -47,10 +88,10 @@ impl KeyObjectHandle {
     digest: &[u8],
     pss_salt_length: Option<u32>,
     dsa_signature_encoding: u32,
-  ) -> Result<Box<[u8]>, AnyError> {
+  ) -> Result<Box<[u8]>, KeyObjectHandlePrehashedSignAndVerifyError> {
     let private_key = self
       .as_private_key()
-      .ok_or_else(|| type_error("key is not a private key"))?;
+      .ok_or(KeyObjectHandlePrehashedSignAndVerifyError::KeyIsNotPrivate)?;
 
     match private_key {
       AsymmetricPrivateKey::Rsa(key) => {
@@ -63,34 +104,26 @@ impl KeyObjectHandle {
               rsa::pkcs1v15::Pkcs1v15Sign::new::<D>()
             },
             _ => {
-              return Err(type_error(format!(
-                "digest not allowed for RSA signature: {}",
-                digest_type
-              )))
+              return Err(KeyObjectHandlePrehashedSignAndVerifyError::DigestNotAllowedForRsaSignature(digest_type.to_string()))
             }
           )
         };
 
         let signature = signer
           .sign(Some(&mut OsRng), key, digest)
-          .map_err(|_| generic_error("failed to sign digest with RSA"))?;
+          .map_err(|_| KeyObjectHandlePrehashedSignAndVerifyError::FailedToSignDigestWithRsa)?;
         Ok(signature.into())
       }
       AsymmetricPrivateKey::RsaPss(key) => {
         let mut hash_algorithm = None;
         let mut salt_length = None;
-        match &key.details {
-          Some(details) => {
-            if details.hash_algorithm != details.mf1_hash_algorithm {
-              return Err(type_error(
-                "rsa-pss with different mf1 hash algorithm and hash algorithm is not supported",
-              ));
-            }
-            hash_algorithm = Some(details.hash_algorithm);
-            salt_length = Some(details.salt_length as usize);
+        if let Some(details) = &key.details {
+          if details.hash_algorithm != details.mf1_hash_algorithm {
+            return Err(KeyObjectHandlePrehashedSignAndVerifyError::RsaPssHashAlgorithmUnsupported);
           }
-          None => {}
-        };
+          hash_algorithm = Some(details.hash_algorithm);
+          salt_length = Some(details.salt_length as usize);
+        }
         if let Some(s) = pss_salt_length {
           salt_length = Some(s as usize);
         }
@@ -99,10 +132,10 @@ impl KeyObjectHandle {
           fn <D>(algorithm: Option<RsaPssHashAlgorithm>) {
             if let Some(hash_algorithm) = hash_algorithm.take() {
               if Some(hash_algorithm) != algorithm {
-                return Err(type_error(format!(
-                  "private key does not allow {} to be used, expected {}",
-                  digest_type, hash_algorithm.as_str()
-                )));
+                return Err(KeyObjectHandlePrehashedSignAndVerifyError::PrivateKeyDisallowsUsage {
+                  actual: digest_type.to_string(),
+                  expected: hash_algorithm.as_str().to_string(),
+                });
               }
             }
             if let Some(salt_length) = salt_length {
@@ -112,15 +145,12 @@ impl KeyObjectHandle {
             }
           },
           _ => {
-            return Err(type_error(format!(
-              "digest not allowed for RSA-PSS signature: {}",
-              digest_type
-            )))
+            return Err(KeyObjectHandlePrehashedSignAndVerifyError::DigestNotAllowedForRsaPssSignature(digest_type.to_string()));
           }
         );
         let signature = pss
           .sign(Some(&mut OsRng), &key.key, digest)
-          .map_err(|_| generic_error("failed to sign digest with RSA-PSS"))?;
+          .map_err(|_| KeyObjectHandlePrehashedSignAndVerifyError::FailedToSignDigestWithRsaPss)?;
         Ok(signature.into())
       }
       AsymmetricPrivateKey::Dsa(key) => {
@@ -130,15 +160,12 @@ impl KeyObjectHandle {
             key.sign_prehashed_rfc6979::<D>(digest)
           },
           _ => {
-            return Err(type_error(format!(
-              "digest not allowed for RSA signature: {}",
-              digest_type
-            )))
+            return Err(KeyObjectHandlePrehashedSignAndVerifyError::DigestNotAllowedForRsaSignature(digest_type.to_string()))
           }
         );
 
         let signature =
-          res.map_err(|_| generic_error("failed to sign digest with DSA"))?;
+          res.map_err(|_| KeyObjectHandlePrehashedSignAndVerifyError::FailedToSignDigestWithDsa)?;
         Ok(signature.into())
       }
       AsymmetricPrivateKey::Ec(key) => match key {
@@ -146,7 +173,7 @@ impl KeyObjectHandle {
           let signing_key = p224::ecdsa::SigningKey::from(key);
           let signature: p224::ecdsa::Signature = signing_key
             .sign_prehash(digest)
-            .map_err(|_| type_error("failed to sign digest"))?;
+            .map_err(|_| KeyObjectHandlePrehashedSignAndVerifyError::FailedToSignDigest)?;
 
           dsa_signature(dsa_signature_encoding, signature)
         }
@@ -154,7 +181,7 @@ impl KeyObjectHandle {
           let signing_key = p256::ecdsa::SigningKey::from(key);
           let signature: p256::ecdsa::Signature = signing_key
             .sign_prehash(digest)
-            .map_err(|_| type_error("failed to sign digest"))?;
+            .map_err(|_| KeyObjectHandlePrehashedSignAndVerifyError::FailedToSignDigest)?;
 
           dsa_signature(dsa_signature_encoding, signature)
         }
@@ -162,19 +189,17 @@ impl KeyObjectHandle {
           let signing_key = p384::ecdsa::SigningKey::from(key);
           let signature: p384::ecdsa::Signature = signing_key
             .sign_prehash(digest)
-            .map_err(|_| type_error("failed to sign digest"))?;
+            .map_err(|_| KeyObjectHandlePrehashedSignAndVerifyError::FailedToSignDigest)?;
 
           dsa_signature(dsa_signature_encoding, signature)
         }
       },
       AsymmetricPrivateKey::X25519(_) => {
-        Err(type_error("x25519 key cannot be used for signing"))
+        Err(KeyObjectHandlePrehashedSignAndVerifyError::X25519KeyCannotBeUsedForSigning)
       }
-      AsymmetricPrivateKey::Ed25519(_) => Err(type_error(
-        "Ed25519 key cannot be used for prehashed signing",
-      )),
+      AsymmetricPrivateKey::Ed25519(_) => Err(KeyObjectHandlePrehashedSignAndVerifyError::Ed25519KeyCannotBeUsedForPrehashedSigning),
       AsymmetricPrivateKey::Dh(_) => {
-        Err(type_error("DH key cannot be used for signing"))
+        Err(KeyObjectHandlePrehashedSignAndVerifyError::DhKeyCannotBeUsedForSigning)
       }
     }
   }
@@ -186,10 +211,10 @@ impl KeyObjectHandle {
     signature: &[u8],
     pss_salt_length: Option<u32>,
     dsa_signature_encoding: u32,
-  ) -> Result<bool, AnyError> {
-    let public_key = self
-      .as_public_key()
-      .ok_or_else(|| type_error("key is not a public or private key"))?;
+  ) -> Result<bool, KeyObjectHandlePrehashedSignAndVerifyError> {
+    let public_key = self.as_public_key().ok_or(
+      KeyObjectHandlePrehashedSignAndVerifyError::KeyIsNotPublicOrPrivate,
+    )?;
 
     match &*public_key {
       AsymmetricPublicKey::Rsa(key) => {
@@ -202,10 +227,7 @@ impl KeyObjectHandle {
               rsa::pkcs1v15::Pkcs1v15Sign::new::<D>()
             },
             _ => {
-              return Err(type_error(format!(
-                "digest not allowed for RSA signature: {}",
-                digest_type
-              )))
+              return Err(KeyObjectHandlePrehashedSignAndVerifyError::DigestNotAllowedForRsaSignature(digest_type.to_string()))
             }
           )
         };
@@ -215,18 +237,13 @@ impl KeyObjectHandle {
       AsymmetricPublicKey::RsaPss(key) => {
         let mut hash_algorithm = None;
         let mut salt_length = None;
-        match &key.details {
-          Some(details) => {
-            if details.hash_algorithm != details.mf1_hash_algorithm {
-              return Err(type_error(
-                "rsa-pss with different mf1 hash algorithm and hash algorithm is not supported",
-              ));
-            }
-            hash_algorithm = Some(details.hash_algorithm);
-            salt_length = Some(details.salt_length as usize);
+        if let Some(details) = &key.details {
+          if details.hash_algorithm != details.mf1_hash_algorithm {
+            return Err(KeyObjectHandlePrehashedSignAndVerifyError::RsaPssHashAlgorithmUnsupported);
           }
-          None => {}
-        };
+          hash_algorithm = Some(details.hash_algorithm);
+          salt_length = Some(details.salt_length as usize);
+        }
         if let Some(s) = pss_salt_length {
           salt_length = Some(s as usize);
         }
@@ -235,10 +252,10 @@ impl KeyObjectHandle {
           fn <D>(algorithm: Option<RsaPssHashAlgorithm>) {
             if let Some(hash_algorithm) = hash_algorithm.take() {
               if Some(hash_algorithm) != algorithm {
-                return Err(type_error(format!(
-                  "private key does not allow {} to be used, expected {}",
-                  digest_type, hash_algorithm.as_str()
-                )));
+                return Err(KeyObjectHandlePrehashedSignAndVerifyError::PrivateKeyDisallowsUsage {
+                  actual: digest_type.to_string(),
+                  expected: hash_algorithm.as_str().to_string(),
+                });
               }
             }
             if let Some(salt_length) = salt_length {
@@ -248,17 +265,14 @@ impl KeyObjectHandle {
             }
           },
           _ => {
-            return Err(type_error(format!(
-              "digest not allowed for RSA-PSS signature: {}",
-              digest_type
-            )))
+            return Err(KeyObjectHandlePrehashedSignAndVerifyError::DigestNotAllowedForRsaPssSignature(digest_type.to_string()));
           }
         );
         Ok(pss.verify(&key.key, digest, signature).is_ok())
       }
       AsymmetricPublicKey::Dsa(key) => {
         let signature = dsa::Signature::from_der(signature)
-          .map_err(|_| type_error("Invalid DSA signature"))?;
+          .map_err(|_| KeyObjectHandlePrehashedSignAndVerifyError::InvalidDsaSignature)?;
         Ok(key.verify_prehash(digest, &signature).is_ok())
       }
       AsymmetricPublicKey::Ec(key) => match key {
@@ -300,13 +314,11 @@ impl KeyObjectHandle {
         }
       },
       AsymmetricPublicKey::X25519(_) => {
-        Err(type_error("x25519 key cannot be used for verification"))
+        Err(KeyObjectHandlePrehashedSignAndVerifyError::X25519KeyCannotBeUsedForVerification)
       }
-      AsymmetricPublicKey::Ed25519(_) => Err(type_error(
-        "Ed25519 key cannot be used for prehashed verification",
-      )),
+      AsymmetricPublicKey::Ed25519(_) => Err(KeyObjectHandlePrehashedSignAndVerifyError::Ed25519KeyCannotBeUsedForPrehashedVerification),
       AsymmetricPublicKey::Dh(_) => {
-        Err(type_error("DH key cannot be used for verification"))
+        Err(KeyObjectHandlePrehashedSignAndVerifyError::DhKeyCannotBeUsedForVerification)
       }
     }
   }
diff --git a/ext/node/ops/crypto/x509.rs b/ext/node/ops/crypto/x509.rs
index b44ff3a4b3..ab8e52f703 100644
--- a/ext/node/ops/crypto/x509.rs
+++ b/ext/node/ops/crypto/x509.rs
@@ -1,11 +1,11 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 
 use x509_parser::der_parser::asn1_rs::Any;
 use x509_parser::der_parser::asn1_rs::Tag;
 use x509_parser::der_parser::oid::Oid;
+pub use x509_parser::error::X509Error;
 use x509_parser::extensions;
 use x509_parser::pem;
 use x509_parser::prelude::*;
@@ -65,7 +65,7 @@ impl<'a> Deref for CertificateView<'a> {
 #[cppgc]
 pub fn op_node_x509_parse(
   #[buffer] buf: &[u8],
-) -> Result<Certificate, AnyError> {
+) -> Result<Certificate, X509Error> {
   let source = match pem::parse_x509_pem(buf) {
     Ok((_, pem)) => CertificateSources::Pem(pem),
     Err(_) => CertificateSources::Der(buf.to_vec().into_boxed_slice()),
@@ -81,7 +81,7 @@ pub fn op_node_x509_parse(
             X509Certificate::from_der(buf).map(|(_, cert)| cert)?
           }
         };
-        Ok::<_, AnyError>(CertificateView { cert })
+        Ok::<_, X509Error>(CertificateView { cert })
       },
     )?;
 
@@ -89,23 +89,23 @@ pub fn op_node_x509_parse(
 }
 
 #[op2(fast)]
-pub fn op_node_x509_ca(#[cppgc] cert: &Certificate) -> Result<bool, AnyError> {
+pub fn op_node_x509_ca(#[cppgc] cert: &Certificate) -> bool {
   let cert = cert.inner.get().deref();
-  Ok(cert.is_ca())
+  cert.is_ca()
 }
 
 #[op2(fast)]
 pub fn op_node_x509_check_email(
   #[cppgc] cert: &Certificate,
   #[string] email: &str,
-) -> Result<bool, AnyError> {
+) -> bool {
   let cert = cert.inner.get().deref();
   let subject = cert.subject();
   if subject
     .iter_email()
     .any(|e| e.as_str().unwrap_or("") == email)
   {
-    return Ok(true);
+    return true;
   }
 
   let subject_alt = cert
@@ -121,62 +121,60 @@ pub fn op_node_x509_check_email(
     for name in &subject_alt.general_names {
       if let extensions::GeneralName::RFC822Name(n) = name {
         if *n == email {
-          return Ok(true);
+          return true;
         }
       }
     }
   }
 
-  Ok(false)
+  false
 }
 
 #[op2]
 #[string]
-pub fn op_node_x509_fingerprint(
-  #[cppgc] cert: &Certificate,
-) -> Result<Option<String>, AnyError> {
-  Ok(cert.fingerprint::<sha1::Sha1>())
+pub fn op_node_x509_fingerprint(#[cppgc] cert: &Certificate) -> Option<String> {
+  cert.fingerprint::<sha1::Sha1>()
 }
 
 #[op2]
 #[string]
 pub fn op_node_x509_fingerprint256(
   #[cppgc] cert: &Certificate,
-) -> Result<Option<String>, AnyError> {
-  Ok(cert.fingerprint::<sha2::Sha256>())
+) -> Option<String> {
+  cert.fingerprint::<sha2::Sha256>()
 }
 
 #[op2]
 #[string]
 pub fn op_node_x509_fingerprint512(
   #[cppgc] cert: &Certificate,
-) -> Result<Option<String>, AnyError> {
-  Ok(cert.fingerprint::<sha2::Sha512>())
+) -> Option<String> {
+  cert.fingerprint::<sha2::Sha512>()
 }
 
 #[op2]
 #[string]
 pub fn op_node_x509_get_issuer(
   #[cppgc] cert: &Certificate,
-) -> Result<String, AnyError> {
+) -> Result<String, X509Error> {
   let cert = cert.inner.get().deref();
-  Ok(x509name_to_string(cert.issuer(), oid_registry())?)
+  x509name_to_string(cert.issuer(), oid_registry())
 }
 
 #[op2]
 #[string]
 pub fn op_node_x509_get_subject(
   #[cppgc] cert: &Certificate,
-) -> Result<String, AnyError> {
+) -> Result<String, X509Error> {
   let cert = cert.inner.get().deref();
-  Ok(x509name_to_string(cert.subject(), oid_registry())?)
+  x509name_to_string(cert.subject(), oid_registry())
 }
 
 #[op2]
 #[cppgc]
 pub fn op_node_x509_public_key(
   #[cppgc] cert: &Certificate,
-) -> Result<KeyObjectHandle, AnyError> {
+) -> Result<KeyObjectHandle, super::keys::X509PublicKeyError> {
   let cert = cert.inner.get().deref();
   let public_key = &cert.tbs_certificate.subject_pki;
 
@@ -245,37 +243,29 @@ fn x509name_to_string(
 
 #[op2]
 #[string]
-pub fn op_node_x509_get_valid_from(
-  #[cppgc] cert: &Certificate,
-) -> Result<String, AnyError> {
+pub fn op_node_x509_get_valid_from(#[cppgc] cert: &Certificate) -> String {
   let cert = cert.inner.get().deref();
-  Ok(cert.validity().not_before.to_string())
+  cert.validity().not_before.to_string()
 }
 
 #[op2]
 #[string]
-pub fn op_node_x509_get_valid_to(
-  #[cppgc] cert: &Certificate,
-) -> Result<String, AnyError> {
+pub fn op_node_x509_get_valid_to(#[cppgc] cert: &Certificate) -> String {
   let cert = cert.inner.get().deref();
-  Ok(cert.validity().not_after.to_string())
+  cert.validity().not_after.to_string()
 }
 
 #[op2]
 #[string]
-pub fn op_node_x509_get_serial_number(
-  #[cppgc] cert: &Certificate,
-) -> Result<String, AnyError> {
+pub fn op_node_x509_get_serial_number(#[cppgc] cert: &Certificate) -> String {
   let cert = cert.inner.get().deref();
   let mut s = cert.serial.to_str_radix(16);
   s.make_ascii_uppercase();
-  Ok(s)
+  s
 }
 
 #[op2(fast)]
-pub fn op_node_x509_key_usage(
-  #[cppgc] cert: &Certificate,
-) -> Result<u16, AnyError> {
+pub fn op_node_x509_key_usage(#[cppgc] cert: &Certificate) -> u16 {
   let cert = cert.inner.get().deref();
   let key_usage = cert
     .extensions()
@@ -286,5 +276,5 @@ pub fn op_node_x509_key_usage(
       _ => None,
     });
 
-  Ok(key_usage.map(|k| k.flags).unwrap_or(0))
+  key_usage.map(|k| k.flags).unwrap_or(0)
 }
diff --git a/ext/node/ops/fs.rs b/ext/node/ops/fs.rs
index 6253f32d05..9c0e4e1ccf 100644
--- a/ext/node/ops/fs.rs
+++ b/ext/node/ops/fs.rs
@@ -3,7 +3,6 @@
 use std::cell::RefCell;
 use std::rc::Rc;
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_fs::FileSystemRc;
@@ -11,11 +10,27 @@ use serde::Serialize;
 
 use crate::NodePermissions;
 
+#[derive(Debug, thiserror::Error)]
+pub enum FsError {
+  #[error(transparent)]
+  Permission(#[from] deno_permissions::PermissionCheckError),
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[cfg(windows)]
+  #[error("Path has no root.")]
+  PathHasNoRoot,
+  #[cfg(not(any(unix, windows)))]
+  #[error("Unsupported platform.")]
+  UnsupportedPlatform,
+  #[error(transparent)]
+  Fs(#[from] deno_io::fs::FsError),
+}
+
 #[op2(fast)]
 pub fn op_node_fs_exists_sync<P>(
   state: &mut OpState,
   #[string] path: String,
-) -> Result<bool, AnyError>
+) -> Result<bool, deno_core::error::AnyError>
 where
   P: NodePermissions + 'static,
 {
@@ -30,7 +45,7 @@ where
 pub async fn op_node_fs_exists<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
-) -> Result<bool, AnyError>
+) -> Result<bool, FsError>
 where
   P: NodePermissions + 'static,
 {
@@ -50,7 +65,7 @@ pub fn op_node_cp_sync<P>(
   state: &mut OpState,
   #[string] path: &str,
   #[string] new_path: &str,
-) -> Result<(), AnyError>
+) -> Result<(), FsError>
 where
   P: NodePermissions + 'static,
 {
@@ -71,7 +86,7 @@ pub async fn op_node_cp<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
   #[string] new_path: String,
-) -> Result<(), AnyError>
+) -> Result<(), FsError>
 where
   P: NodePermissions + 'static,
 {
@@ -108,7 +123,7 @@ pub fn op_node_statfs<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
   bigint: bool,
-) -> Result<StatFs, AnyError>
+) -> Result<StatFs, FsError>
 where
   P: NodePermissions + 'static,
 {
@@ -130,13 +145,21 @@ where
     let mut cpath = path.as_bytes().to_vec();
     cpath.push(0);
     if bigint {
-      #[cfg(not(target_os = "macos"))]
+      #[cfg(not(any(
+        target_os = "macos",
+        target_os = "freebsd",
+        target_os = "openbsd"
+      )))]
       // SAFETY: `cpath` is NUL-terminated and result is pointer to valid statfs memory.
       let (code, result) = unsafe {
         let mut result: libc::statfs64 = std::mem::zeroed();
         (libc::statfs64(cpath.as_ptr() as _, &mut result), result)
       };
-      #[cfg(target_os = "macos")]
+      #[cfg(any(
+        target_os = "macos",
+        target_os = "freebsd",
+        target_os = "openbsd"
+      ))]
       // SAFETY: `cpath` is NUL-terminated and result is pointer to valid statfs memory.
       let (code, result) = unsafe {
         let mut result: libc::statfs = std::mem::zeroed();
@@ -146,7 +169,10 @@ where
         return Err(std::io::Error::last_os_error().into());
       }
       Ok(StatFs {
+        #[cfg(not(target_os = "openbsd"))]
         typ: result.f_type as _,
+        #[cfg(target_os = "openbsd")]
+        typ: 0 as _,
         bsize: result.f_bsize as _,
         blocks: result.f_blocks as _,
         bfree: result.f_bfree as _,
@@ -164,7 +190,10 @@ where
         return Err(std::io::Error::last_os_error().into());
       }
       Ok(StatFs {
+        #[cfg(not(target_os = "openbsd"))]
         typ: result.f_type as _,
+        #[cfg(target_os = "openbsd")]
+        typ: 0 as _,
         bsize: result.f_bsize as _,
         blocks: result.f_blocks as _,
         bfree: result.f_bfree as _,
@@ -176,7 +205,6 @@ where
   }
   #[cfg(windows)]
   {
-    use deno_core::anyhow::anyhow;
     use std::ffi::OsStr;
     use std::os::windows::ffi::OsStrExt;
     use windows_sys::Win32::Storage::FileSystem::GetDiskFreeSpaceW;
@@ -186,10 +214,7 @@ where
     // call below.
     #[allow(clippy::disallowed_methods)]
     let path = path.canonicalize()?;
-    let root = path
-      .ancestors()
-      .last()
-      .ok_or(anyhow!("Path has no root."))?;
+    let root = path.ancestors().last().ok_or(FsError::PathHasNoRoot)?;
     let mut root = OsStr::new(root).encode_wide().collect::<Vec<_>>();
     root.push(0);
     let mut sectors_per_cluster = 0;
@@ -229,7 +254,7 @@ where
   {
     let _ = path;
     let _ = bigint;
-    Err(anyhow!("Unsupported platform."))
+    Err(FsError::UnsupportedPlatform)
   }
 }
 
@@ -241,7 +266,7 @@ pub fn op_node_lutimes_sync<P>(
   #[smi] atime_nanos: u32,
   #[number] mtime_secs: i64,
   #[smi] mtime_nanos: u32,
-) -> Result<(), AnyError>
+) -> Result<(), FsError>
 where
   P: NodePermissions + 'static,
 {
@@ -262,7 +287,7 @@ pub async fn op_node_lutimes<P>(
   #[smi] atime_nanos: u32,
   #[number] mtime_secs: i64,
   #[smi] mtime_nanos: u32,
-) -> Result<(), AnyError>
+) -> Result<(), FsError>
 where
   P: NodePermissions + 'static,
 {
@@ -286,7 +311,7 @@ pub fn op_node_lchown_sync<P>(
   #[string] path: String,
   uid: Option<u32>,
   gid: Option<u32>,
-) -> Result<(), AnyError>
+) -> Result<(), FsError>
 where
   P: NodePermissions + 'static,
 {
@@ -304,7 +329,7 @@ pub async fn op_node_lchown<P>(
   #[string] path: String,
   uid: Option<u32>,
   gid: Option<u32>,
-) -> Result<(), AnyError>
+) -> Result<(), FsError>
 where
   P: NodePermissions + 'static,
 {
diff --git a/ext/node/ops/http.rs b/ext/node/ops/http.rs
index 773902dedf..69571078fe 100644
--- a/ext/node/ops/http.rs
+++ b/ext/node/ops/http.rs
@@ -8,14 +8,12 @@ use std::task::Context;
 use std::task::Poll;
 
 use bytes::Bytes;
-use deno_core::anyhow;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::futures::stream::Peekable;
 use deno_core::futures::Future;
 use deno_core::futures::FutureExt;
 use deno_core::futures::Stream;
 use deno_core::futures::StreamExt;
+use deno_core::futures::TryFutureExt;
 use deno_core::op2;
 use deno_core::serde::Serialize;
 use deno_core::unsync::spawn;
@@ -33,6 +31,7 @@ use deno_core::Resource;
 use deno_core::ResourceId;
 use deno_fetch::get_or_create_client_from_state;
 use deno_fetch::FetchCancelHandle;
+use deno_fetch::FetchError;
 use deno_fetch::FetchRequestResource;
 use deno_fetch::FetchReturn;
 use deno_fetch::HttpClientResource;
@@ -59,12 +58,15 @@ pub fn op_node_http_request<P>(
   #[serde] headers: Vec<(ByteString, ByteString)>,
   #[smi] client_rid: Option<u32>,
   #[smi] body: Option<ResourceId>,
-) -> Result<FetchReturn, AnyError>
+) -> Result<FetchReturn, FetchError>
 where
   P: crate::NodePermissions + 'static,
 {
   let client = if let Some(rid) = client_rid {
-    let r = state.resource_table.get::<HttpClientResource>(rid)?;
+    let r = state
+      .resource_table
+      .get::<HttpClientResource>(rid)
+      .map_err(FetchError::Resource)?;
     r.client.clone()
   } else {
     get_or_create_client_from_state(state)?
@@ -81,10 +83,8 @@ where
 
   let mut header_map = HeaderMap::new();
   for (key, value) in headers {
-    let name = HeaderName::from_bytes(&key)
-      .map_err(|err| type_error(err.to_string()))?;
-    let v = HeaderValue::from_bytes(&value)
-      .map_err(|err| type_error(err.to_string()))?;
+    let name = HeaderName::from_bytes(&key)?;
+    let v = HeaderValue::from_bytes(&value)?;
 
     header_map.append(name, v);
   }
@@ -92,7 +92,10 @@ where
   let (body, con_len) = if let Some(body) = body {
     (
       BodyExt::boxed(NodeHttpResourceToBodyAdapter::new(
-        state.resource_table.take_any(body)?,
+        state
+          .resource_table
+          .take_any(body)
+          .map_err(FetchError::Resource)?,
       )),
       None,
     )
@@ -117,7 +120,7 @@ where
   *request.uri_mut() = url
     .as_str()
     .parse()
-    .map_err(|_| type_error("Invalid URL"))?;
+    .map_err(|_| FetchError::InvalidUrl(url.clone()))?;
   *request.headers_mut() = header_map;
 
   if let Some((username, password)) = maybe_authority {
@@ -136,9 +139,9 @@ where
   let fut = async move {
     client
       .send(request)
+      .map_err(Into::into)
       .or_cancel(cancel_handle_)
       .await
-      .map(|res| res.map_err(|err| type_error(err.to_string())))
   };
 
   let request_rid = state.resource_table.add(FetchRequestResource {
@@ -174,11 +177,12 @@ pub struct NodeHttpFetchResponse {
 pub async fn op_node_http_fetch_send(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<NodeHttpFetchResponse, AnyError> {
+) -> Result<NodeHttpFetchResponse, FetchError> {
   let request = state
     .borrow_mut()
     .resource_table
-    .take::<FetchRequestResource>(rid)?;
+    .take::<FetchRequestResource>(rid)
+    .map_err(FetchError::Resource)?;
 
   let request = Rc::try_unwrap(request)
     .ok()
@@ -191,22 +195,23 @@ pub async fn op_node_http_fetch_send(
       // If any error in the chain is a hyper body error, return that as a special result we can use to
       // reconstruct an error chain (eg: `new TypeError(..., { cause: new Error(...) })`).
       // TODO(mmastrac): it would be a lot easier if we just passed a v8::Global through here instead
-      let mut err_ref: &dyn std::error::Error = err.as_ref();
-      while let Some(err) = std::error::Error::source(err_ref) {
-        if let Some(err) = err.downcast_ref::<hyper::Error>() {
-          if let Some(err) = std::error::Error::source(err) {
-            return Ok(NodeHttpFetchResponse {
-              error: Some(err.to_string()),
-              ..Default::default()
-            });
+
+      if let FetchError::ClientSend(err_src) = &err {
+        if let Some(client_err) = std::error::Error::source(&err_src.source) {
+          if let Some(err_src) = client_err.downcast_ref::<hyper::Error>() {
+            if let Some(err_src) = std::error::Error::source(err_src) {
+              return Ok(NodeHttpFetchResponse {
+                error: Some(err_src.to_string()),
+                ..Default::default()
+              });
+            }
           }
         }
-        err_ref = err;
       }
 
-      return Err(type_error(err.to_string()));
+      return Err(err);
     }
-    Err(_) => return Err(type_error("request was cancelled")),
+    Err(_) => return Err(FetchError::RequestCanceled),
   };
 
   let status = res.status();
@@ -250,11 +255,12 @@ pub async fn op_node_http_fetch_send(
 pub async fn op_node_http_fetch_response_upgrade(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, FetchError> {
   let raw_response = state
     .borrow_mut()
     .resource_table
-    .take::<NodeHttpFetchResponseResource>(rid)?;
+    .take::<NodeHttpFetchResponseResource>(rid)
+    .map_err(FetchError::Resource)?;
   let raw_response = Rc::try_unwrap(raw_response)
     .expect("Someone is holding onto NodeHttpFetchResponseResource");
 
@@ -277,7 +283,7 @@ pub async fn op_node_http_fetch_response_upgrade(
         }
         read_tx.write_all(&buf[..read]).await?;
       }
-      Ok::<_, AnyError>(())
+      Ok::<_, FetchError>(())
     });
     spawn(async move {
       let mut buf = [0; 1024];
@@ -288,7 +294,7 @@ pub async fn op_node_http_fetch_response_upgrade(
         }
         upgraded_tx.write_all(&buf[..read]).await?;
       }
-      Ok::<_, AnyError>(())
+      Ok::<_, FetchError>(())
     });
   }
 
@@ -318,23 +324,26 @@ impl UpgradeStream {
     }
   }
 
-  async fn read(self: Rc<Self>, buf: &mut [u8]) -> Result<usize, AnyError> {
+  async fn read(
+    self: Rc<Self>,
+    buf: &mut [u8],
+  ) -> Result<usize, std::io::Error> {
     let cancel_handle = RcRef::map(self.clone(), |this| &this.cancel_handle);
     async {
       let read = RcRef::map(self, |this| &this.read);
       let mut read = read.borrow_mut().await;
-      Ok(Pin::new(&mut *read).read(buf).await?)
+      Pin::new(&mut *read).read(buf).await
     }
     .try_or_cancel(cancel_handle)
     .await
   }
 
-  async fn write(self: Rc<Self>, buf: &[u8]) -> Result<usize, AnyError> {
+  async fn write(self: Rc<Self>, buf: &[u8]) -> Result<usize, std::io::Error> {
     let cancel_handle = RcRef::map(self.clone(), |this| &this.cancel_handle);
     async {
       let write = RcRef::map(self, |this| &this.write);
       let mut write = write.borrow_mut().await;
-      Ok(Pin::new(&mut *write).write(buf).await?)
+      Pin::new(&mut *write).write(buf).await
     }
     .try_or_cancel(cancel_handle)
     .await
@@ -387,7 +396,7 @@ impl NodeHttpFetchResponseResource {
     }
   }
 
-  pub async fn upgrade(self) -> Result<hyper::upgrade::Upgraded, AnyError> {
+  pub async fn upgrade(self) -> Result<hyper::upgrade::Upgraded, hyper::Error> {
     let reader = self.response_reader.into_inner();
     match reader {
       NodeHttpFetchResponseReader::Start(resp) => {
@@ -445,7 +454,9 @@ impl Resource for NodeHttpFetchResponseResource {
             // safely call `await` on it without creating a race condition.
             Some(_) => match reader.as_mut().next().await.unwrap() {
               Ok(chunk) => assert!(chunk.is_empty()),
-              Err(err) => break Err(type_error(err.to_string())),
+              Err(err) => {
+                break Err(deno_core::error::type_error(err.to_string()))
+              }
             },
             None => break Ok(BufView::empty()),
           }
@@ -453,7 +464,7 @@ impl Resource for NodeHttpFetchResponseResource {
       };
 
       let cancel_handle = RcRef::map(self, |r| &r.cancel);
-      fut.try_or_cancel(cancel_handle).await
+      fut.try_or_cancel(cancel_handle).await.map_err(Into::into)
     })
   }
 
@@ -469,7 +480,9 @@ impl Resource for NodeHttpFetchResponseResource {
 #[allow(clippy::type_complexity)]
 pub struct NodeHttpResourceToBodyAdapter(
   Rc<dyn Resource>,
-  Option<Pin<Box<dyn Future<Output = Result<BufView, anyhow::Error>>>>>,
+  Option<
+    Pin<Box<dyn Future<Output = Result<BufView, deno_core::anyhow::Error>>>>,
+  >,
 );
 
 impl NodeHttpResourceToBodyAdapter {
@@ -485,7 +498,7 @@ unsafe impl Send for NodeHttpResourceToBodyAdapter {}
 unsafe impl Sync for NodeHttpResourceToBodyAdapter {}
 
 impl Stream for NodeHttpResourceToBodyAdapter {
-  type Item = Result<Bytes, anyhow::Error>;
+  type Item = Result<Bytes, deno_core::anyhow::Error>;
 
   fn poll_next(
     self: Pin<&mut Self>,
@@ -515,7 +528,7 @@ impl Stream for NodeHttpResourceToBodyAdapter {
 
 impl hyper::body::Body for NodeHttpResourceToBodyAdapter {
   type Data = Bytes;
-  type Error = anyhow::Error;
+  type Error = deno_core::anyhow::Error;
 
   fn poll_frame(
     self: Pin<&mut Self>,
diff --git a/ext/node/ops/http2.rs b/ext/node/ops/http2.rs
index 9595cb33d6..53dada9f41 100644
--- a/ext/node/ops/http2.rs
+++ b/ext/node/ops/http2.rs
@@ -7,7 +7,6 @@ use std::rc::Rc;
 use std::task::Poll;
 
 use bytes::Bytes;
-use deno_core::error::AnyError;
 use deno_core::futures::future::poll_fn;
 use deno_core::op2;
 use deno_core::serde::Serialize;
@@ -110,17 +109,28 @@ impl Resource for Http2ServerSendResponse {
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum Http2Error {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  UrlParse(#[from] url::ParseError),
+  #[error(transparent)]
+  H2(#[from] h2::Error),
+}
+
 #[op2(async)]
 #[serde]
 pub async fn op_http2_connect(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[string] url: String,
-) -> Result<(ResourceId, ResourceId), AnyError> {
+) -> Result<(ResourceId, ResourceId), Http2Error> {
   // No permission check necessary because we're using an existing connection
   let network_stream = {
     let mut state = state.borrow_mut();
-    take_network_stream_resource(&mut state.resource_table, rid)?
+    take_network_stream_resource(&mut state.resource_table, rid)
+      .map_err(Http2Error::Resource)?
   };
 
   let url = Url::parse(&url)?;
@@ -144,9 +154,10 @@ pub async fn op_http2_connect(
 pub async fn op_http2_listen(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, Http2Error> {
   let stream =
-    take_network_stream_resource(&mut state.borrow_mut().resource_table, rid)?;
+    take_network_stream_resource(&mut state.borrow_mut().resource_table, rid)
+      .map_err(Http2Error::Resource)?;
 
   let conn = h2::server::Builder::new().handshake(stream).await?;
   Ok(
@@ -166,12 +177,13 @@ pub async fn op_http2_accept(
   #[smi] rid: ResourceId,
 ) -> Result<
   Option<(Vec<(ByteString, ByteString)>, ResourceId, ResourceId)>,
-  AnyError,
+  Http2Error,
 > {
   let resource = state
     .borrow()
     .resource_table
-    .get::<Http2ServerConnection>(rid)?;
+    .get::<Http2ServerConnection>(rid)
+    .map_err(Http2Error::Resource)?;
   let mut conn = RcRef::map(&resource, |r| &r.conn).borrow_mut().await;
   if let Some(res) = conn.accept().await {
     let (req, resp) = res?;
@@ -233,11 +245,12 @@ pub async fn op_http2_send_response(
   #[smi] rid: ResourceId,
   #[smi] status: u16,
   #[serde] headers: Vec<(ByteString, ByteString)>,
-) -> Result<(ResourceId, u32), AnyError> {
+) -> Result<(ResourceId, u32), Http2Error> {
   let resource = state
     .borrow()
     .resource_table
-    .get::<Http2ServerSendResponse>(rid)?;
+    .get::<Http2ServerSendResponse>(rid)
+    .map_err(Http2Error::Resource)?;
   let mut send_response = RcRef::map(resource, |r| &r.send_response)
     .borrow_mut()
     .await;
@@ -262,8 +275,12 @@ pub async fn op_http2_send_response(
 pub async fn op_http2_poll_client_connection(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
-  let resource = state.borrow().resource_table.get::<Http2ClientConn>(rid)?;
+) -> Result<(), Http2Error> {
+  let resource = state
+    .borrow()
+    .resource_table
+    .get::<Http2ClientConn>(rid)
+    .map_err(Http2Error::Resource)?;
 
   let cancel_handle = RcRef::map(resource.clone(), |this| &this.cancel_handle);
   let mut conn = RcRef::map(resource, |this| &this.conn).borrow_mut().await;
@@ -289,11 +306,12 @@ pub async fn op_http2_client_request(
   // 4 strings of keys?
   #[serde] mut pseudo_headers: HashMap<String, String>,
   #[serde] headers: Vec<(ByteString, ByteString)>,
-) -> Result<(ResourceId, u32), AnyError> {
+) -> Result<(ResourceId, u32), Http2Error> {
   let resource = state
     .borrow()
     .resource_table
-    .get::<Http2Client>(client_rid)?;
+    .get::<Http2Client>(client_rid)
+    .map_err(Http2Error::Resource)?;
 
   let url = resource.url.clone();
 
@@ -326,7 +344,10 @@ pub async fn op_http2_client_request(
 
   let resource = {
     let state = state.borrow();
-    state.resource_table.get::<Http2Client>(client_rid)?
+    state
+      .resource_table
+      .get::<Http2Client>(client_rid)
+      .map_err(Http2Error::Resource)?
   };
   let mut client = RcRef::map(&resource, |r| &r.client).borrow_mut().await;
   poll_fn(|cx| client.poll_ready(cx)).await?;
@@ -345,11 +366,12 @@ pub async fn op_http2_client_send_data(
   #[smi] stream_rid: ResourceId,
   #[buffer] data: JsBuffer,
   end_of_stream: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), Http2Error> {
   let resource = state
     .borrow()
     .resource_table
-    .get::<Http2ClientStream>(stream_rid)?;
+    .get::<Http2ClientStream>(stream_rid)
+    .map_err(Http2Error::Resource)?;
   let mut stream = RcRef::map(&resource, |r| &r.stream).borrow_mut().await;
 
   stream.send_data(data.to_vec().into(), end_of_stream)?;
@@ -361,7 +383,7 @@ pub async fn op_http2_client_reset_stream(
   state: Rc<RefCell<OpState>>,
   #[smi] stream_rid: ResourceId,
   #[smi] code: u32,
-) -> Result<(), AnyError> {
+) -> Result<(), deno_core::error::AnyError> {
   let resource = state
     .borrow()
     .resource_table
@@ -376,11 +398,12 @@ pub async fn op_http2_client_send_trailers(
   state: Rc<RefCell<OpState>>,
   #[smi] stream_rid: ResourceId,
   #[serde] trailers: Vec<(ByteString, ByteString)>,
-) -> Result<(), AnyError> {
+) -> Result<(), Http2Error> {
   let resource = state
     .borrow()
     .resource_table
-    .get::<Http2ClientStream>(stream_rid)?;
+    .get::<Http2ClientStream>(stream_rid)
+    .map_err(Http2Error::Resource)?;
   let mut stream = RcRef::map(&resource, |r| &r.stream).borrow_mut().await;
 
   let mut trailers_map = http::HeaderMap::new();
@@ -408,11 +431,12 @@ pub struct Http2ClientResponse {
 pub async fn op_http2_client_get_response(
   state: Rc<RefCell<OpState>>,
   #[smi] stream_rid: ResourceId,
-) -> Result<(Http2ClientResponse, bool), AnyError> {
+) -> Result<(Http2ClientResponse, bool), Http2Error> {
   let resource = state
     .borrow()
     .resource_table
-    .get::<Http2ClientStream>(stream_rid)?;
+    .get::<Http2ClientStream>(stream_rid)
+    .map_err(Http2Error::Resource)?;
   let mut response_future =
     RcRef::map(&resource, |r| &r.response).borrow_mut().await;
 
@@ -478,23 +502,22 @@ fn poll_data_or_trailers(
 pub async fn op_http2_client_get_response_body_chunk(
   state: Rc<RefCell<OpState>>,
   #[smi] body_rid: ResourceId,
-) -> Result<(Option<Vec<u8>>, bool, bool), AnyError> {
+) -> Result<(Option<Vec<u8>>, bool, bool), Http2Error> {
   let resource = state
     .borrow()
     .resource_table
-    .get::<Http2ClientResponseBody>(body_rid)?;
+    .get::<Http2ClientResponseBody>(body_rid)
+    .map_err(Http2Error::Resource)?;
   let mut body = RcRef::map(&resource, |r| &r.body).borrow_mut().await;
 
   loop {
     let result = poll_fn(|cx| poll_data_or_trailers(cx, &mut body)).await;
     if let Err(err) = result {
-      let reason = err.reason();
-      if let Some(reason) = reason {
-        if reason == Reason::CANCEL {
-          return Ok((None, false, true));
-        }
+      match err.reason() {
+        Some(Reason::NO_ERROR) => return Ok((None, true, false)),
+        Some(Reason::CANCEL) => return Ok((None, false, true)),
+        _ => return Err(err.into()),
       }
-      return Err(err.into());
     }
     match result.unwrap() {
       DataOrTrailers::Data(data) => {
@@ -527,7 +550,7 @@ pub async fn op_http2_client_get_response_body_chunk(
 pub async fn op_http2_client_get_response_trailers(
   state: Rc<RefCell<OpState>>,
   #[smi] body_rid: ResourceId,
-) -> Result<Option<Vec<(ByteString, ByteString)>>, AnyError> {
+) -> Result<Option<Vec<(ByteString, ByteString)>>, deno_core::error::AnyError> {
   let resource = state
     .borrow()
     .resource_table
diff --git a/ext/node/ops/idna.rs b/ext/node/ops/idna.rs
index 9c9450c70f..a3d85e77c2 100644
--- a/ext/node/ops/idna.rs
+++ b/ext/node/ops/idna.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::anyhow::Error;
-use deno_core::error::range_error;
 use deno_core::op2;
 
 use std::borrow::Cow;
@@ -11,19 +9,21 @@ use std::borrow::Cow;
 
 const PUNY_PREFIX: &str = "xn--";
 
-fn invalid_input_err() -> Error {
-  range_error("Invalid input")
-}
-
-fn not_basic_err() -> Error {
-  range_error("Illegal input >= 0x80 (not a basic code point)")
+#[derive(Debug, thiserror::Error)]
+pub enum IdnaError {
+  #[error("Invalid input")]
+  InvalidInput,
+  #[error("Input would take more than 63 characters to encode")]
+  InputTooLong,
+  #[error("Illegal input >= 0x80 (not a basic code point)")]
+  IllegalInput,
 }
 
 /// map a domain by mapping each label with the given function
-fn map_domain<E>(
+fn map_domain(
   domain: &str,
-  f: impl Fn(&str) -> Result<Cow<'_, str>, E>,
-) -> Result<String, E> {
+  f: impl Fn(&str) -> Result<Cow<'_, str>, IdnaError>,
+) -> Result<String, IdnaError> {
   let mut result = String::with_capacity(domain.len());
   let mut domain = domain;
 
@@ -48,7 +48,7 @@ fn map_domain<E>(
 /// Maps a unicode domain to ascii by punycode encoding each label
 ///
 /// Note this is not IDNA2003 or IDNA2008 compliant, rather it matches node.js's punycode implementation
-fn to_ascii(input: &str) -> Result<String, Error> {
+fn to_ascii(input: &str) -> Result<String, IdnaError> {
   if input.is_ascii() {
     return Ok(input.into());
   }
@@ -61,9 +61,7 @@ fn to_ascii(input: &str) -> Result<String, Error> {
     } else {
       idna::punycode::encode_str(label)
         .map(|encoded| [PUNY_PREFIX, &encoded].join("").into()) // add the prefix
-        .ok_or_else(|| {
-          Error::msg("Input would take more than 63 characters to encode") // only error possible per the docs
-        })
+        .ok_or(IdnaError::InputTooLong) // only error possible per the docs
     }
   })?;
 
@@ -74,13 +72,13 @@ fn to_ascii(input: &str) -> Result<String, Error> {
 /// Maps an ascii domain to unicode by punycode decoding each label
 ///
 /// Note this is not IDNA2003 or IDNA2008 compliant, rather it matches node.js's punycode implementation
-fn to_unicode(input: &str) -> Result<String, Error> {
+fn to_unicode(input: &str) -> Result<String, IdnaError> {
   map_domain(input, |s| {
     if let Some(puny) = s.strip_prefix(PUNY_PREFIX) {
       // it's a punycode encoded label
       Ok(
         idna::punycode::decode_to_string(&puny.to_lowercase())
-          .ok_or_else(invalid_input_err)?
+          .ok_or(IdnaError::InvalidInput)?
           .into(),
       )
     } else {
@@ -95,7 +93,7 @@ fn to_unicode(input: &str) -> Result<String, Error> {
 #[string]
 pub fn op_node_idna_punycode_to_ascii(
   #[string] domain: String,
-) -> Result<String, Error> {
+) -> Result<String, IdnaError> {
   to_ascii(&domain)
 }
 
@@ -105,7 +103,7 @@ pub fn op_node_idna_punycode_to_ascii(
 #[string]
 pub fn op_node_idna_punycode_to_unicode(
   #[string] domain: String,
-) -> Result<String, Error> {
+) -> Result<String, IdnaError> {
   to_unicode(&domain)
 }
 
@@ -115,8 +113,8 @@ pub fn op_node_idna_punycode_to_unicode(
 #[string]
 pub fn op_node_idna_domain_to_ascii(
   #[string] domain: String,
-) -> Result<String, Error> {
-  idna::domain_to_ascii(&domain).map_err(|e| e.into())
+) -> Result<String, idna::Errors> {
+  idna::domain_to_ascii(&domain)
 }
 
 /// Converts a domain to Unicode as per the IDNA spec
@@ -131,7 +129,7 @@ pub fn op_node_idna_domain_to_unicode(#[string] domain: String) -> String {
 #[string]
 pub fn op_node_idna_punycode_decode(
   #[string] domain: String,
-) -> Result<String, Error> {
+) -> Result<String, IdnaError> {
   if domain.is_empty() {
     return Ok(domain);
   }
@@ -147,11 +145,10 @@ pub fn op_node_idna_punycode_decode(
       .unwrap_or(domain.len() - 1);
 
   if !domain[..last_dash].is_ascii() {
-    return Err(not_basic_err());
+    return Err(IdnaError::IllegalInput);
   }
 
-  idna::punycode::decode_to_string(&domain)
-    .ok_or_else(|| deno_core::error::range_error("Invalid input"))
+  idna::punycode::decode_to_string(&domain).ok_or(IdnaError::InvalidInput)
 }
 
 #[op2]
diff --git a/ext/node/ops/inspector.rs b/ext/node/ops/inspector.rs
new file mode 100644
index 0000000000..34a7e004c1
--- /dev/null
+++ b/ext/node/ops/inspector.rs
@@ -0,0 +1,161 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+use crate::NodePermissions;
+use deno_core::anyhow::Error;
+use deno_core::error::generic_error;
+use deno_core::futures::channel::mpsc;
+use deno_core::op2;
+use deno_core::v8;
+use deno_core::GarbageCollected;
+use deno_core::InspectorSessionKind;
+use deno_core::InspectorSessionOptions;
+use deno_core::JsRuntimeInspector;
+use deno_core::OpState;
+use std::cell::RefCell;
+use std::rc::Rc;
+
+#[op2(fast)]
+pub fn op_inspector_enabled() -> bool {
+  // TODO: hook up to InspectorServer
+  false
+}
+
+#[op2]
+pub fn op_inspector_open<P>(
+  _state: &mut OpState,
+  _port: Option<u16>,
+  #[string] _host: Option<String>,
+) -> Result<(), Error>
+where
+  P: NodePermissions + 'static,
+{
+  // TODO: hook up to InspectorServer
+  /*
+  let server = state.borrow_mut::<InspectorServer>();
+  if let Some(host) = host {
+    server.set_host(host);
+  }
+  if let Some(port) = port {
+    server.set_port(port);
+  }
+  state
+    .borrow_mut::<P>()
+    .check_net((server.host(), Some(server.port())), "inspector.open")?;
+  */
+
+  Ok(())
+}
+
+#[op2(fast)]
+pub fn op_inspector_close() {
+  // TODO: hook up to InspectorServer
+}
+
+#[op2]
+#[string]
+pub fn op_inspector_url() -> Option<String> {
+  // TODO: hook up to InspectorServer
+  None
+}
+
+#[op2(fast)]
+pub fn op_inspector_wait(state: &OpState) -> bool {
+  match state.try_borrow::<Rc<RefCell<JsRuntimeInspector>>>() {
+    Some(inspector) => {
+      inspector
+        .borrow_mut()
+        .wait_for_session_and_break_on_next_statement();
+      true
+    }
+    None => false,
+  }
+}
+
+#[op2(fast)]
+pub fn op_inspector_emit_protocol_event(
+  #[string] _event_name: String,
+  #[string] _params: String,
+) {
+  // TODO: inspector channel & protocol notifications
+}
+
+struct JSInspectorSession {
+  tx: RefCell<Option<mpsc::UnboundedSender<String>>>,
+}
+
+impl GarbageCollected for JSInspectorSession {}
+
+#[op2]
+#[cppgc]
+pub fn op_inspector_connect<'s, P>(
+  isolate: *mut v8::Isolate,
+  scope: &mut v8::HandleScope<'s>,
+  state: &mut OpState,
+  connect_to_main_thread: bool,
+  callback: v8::Local<'s, v8::Function>,
+) -> Result<JSInspectorSession, Error>
+where
+  P: NodePermissions + 'static,
+{
+  state
+    .borrow_mut::<P>()
+    .check_sys("inspector", "inspector.Session.connect")?;
+
+  if connect_to_main_thread {
+    return Err(generic_error("connectToMainThread not supported"));
+  }
+
+  let context = scope.get_current_context();
+  let context = v8::Global::new(scope, context);
+  let callback = v8::Global::new(scope, callback);
+
+  let inspector = state
+    .borrow::<Rc<RefCell<JsRuntimeInspector>>>()
+    .borrow_mut();
+
+  let tx = inspector.create_raw_session(
+    InspectorSessionOptions {
+      kind: InspectorSessionKind::NonBlocking {
+        wait_for_disconnect: false,
+      },
+    },
+    // The inspector connection does not keep the event loop alive but
+    // when the inspector sends a message to the frontend, the JS that
+    // that runs may keep the event loop alive so we have to call back
+    // synchronously, instead of using the usual LocalInspectorSession
+    // UnboundedReceiver<InspectorMsg> API.
+    Box::new(move |message| {
+      // SAFETY: This function is called directly by the inspector, so
+      //   1) The isolate is still valid
+      //   2) We are on the same thread as the Isolate
+      let scope = unsafe { &mut v8::CallbackScope::new(&mut *isolate) };
+      let context = v8::Local::new(scope, context.clone());
+      let scope = &mut v8::ContextScope::new(scope, context);
+      let scope = &mut v8::TryCatch::new(scope);
+      let recv = v8::undefined(scope);
+      if let Some(message) = v8::String::new(scope, &message.content) {
+        let callback = v8::Local::new(scope, callback.clone());
+        callback.call(scope, recv.into(), &[message.into()]);
+      }
+    }),
+  );
+
+  Ok(JSInspectorSession {
+    tx: RefCell::new(Some(tx)),
+  })
+}
+
+#[op2(fast)]
+pub fn op_inspector_dispatch(
+  #[cppgc] session: &JSInspectorSession,
+  #[string] message: String,
+) {
+  if let Some(tx) = &*session.tx.borrow() {
+    let _ = tx.unbounded_send(message);
+  }
+}
+
+#[op2(fast)]
+pub fn op_inspector_disconnect(#[cppgc] session: &JSInspectorSession) {
+  drop(session.tx.borrow_mut().take());
+}
diff --git a/ext/node/ops/ipc.rs b/ext/node/ops/ipc.rs
index 59b6fece14..672cf0d707 100644
--- a/ext/node/ops/ipc.rs
+++ b/ext/node/ops/ipc.rs
@@ -17,8 +17,6 @@ mod impl_ {
   use std::task::Context;
   use std::task::Poll;
 
-  use deno_core::error::bad_resource_id;
-  use deno_core::error::AnyError;
   use deno_core::op2;
   use deno_core::serde;
   use deno_core::serde::Serializer;
@@ -167,7 +165,7 @@ mod impl_ {
   #[smi]
   pub fn op_node_child_ipc_pipe(
     state: &mut OpState,
-  ) -> Result<Option<ResourceId>, AnyError> {
+  ) -> Result<Option<ResourceId>, io::Error> {
     let fd = match state.try_borrow_mut::<crate::ChildPipeFd>() {
       Some(child_pipe_fd) => child_pipe_fd.0,
       None => return Ok(None),
@@ -180,6 +178,18 @@ mod impl_ {
     ))
   }
 
+  #[derive(Debug, thiserror::Error)]
+  pub enum IpcError {
+    #[error(transparent)]
+    Resource(deno_core::error::AnyError),
+    #[error(transparent)]
+    IpcJsonStream(#[from] IpcJsonStreamError),
+    #[error(transparent)]
+    Canceled(#[from] deno_core::Canceled),
+    #[error("failed to serialize json value: {0}")]
+    SerdeJson(serde_json::Error),
+  }
+
   #[op2(async)]
   pub fn op_node_ipc_write<'a>(
     scope: &mut v8::HandleScope<'a>,
@@ -192,34 +202,37 @@ mod impl_ {
     // ideally we would just return `Result<(impl Future, bool), ..>`, but that's not
     // supported by `op2` currently.
     queue_ok: v8::Local<'a, v8::Array>,
-  ) -> Result<impl Future<Output = Result<(), AnyError>>, AnyError> {
+  ) -> Result<impl Future<Output = Result<(), io::Error>>, IpcError> {
     let mut serialized = Vec::with_capacity(64);
     let mut ser = serde_json::Serializer::new(&mut serialized);
-    serialize_v8_value(scope, value, &mut ser).map_err(|e| {
-      deno_core::error::type_error(format!(
-        "failed to serialize json value: {e}"
-      ))
-    })?;
+    serialize_v8_value(scope, value, &mut ser).map_err(IpcError::SerdeJson)?;
     serialized.push(b'\n');
 
     let stream = state
       .borrow()
       .resource_table
       .get::<IpcJsonStreamResource>(rid)
-      .map_err(|_| bad_resource_id())?;
+      .map_err(IpcError::Resource)?;
     let old = stream
       .queued_bytes
       .fetch_add(serialized.len(), std::sync::atomic::Ordering::Relaxed);
     if old + serialized.len() > 2 * INITIAL_CAPACITY {
       // sending messages too fast
-      let v = false.to_v8(scope)?;
+      let v = false.to_v8(scope).unwrap(); // Infallible
       queue_ok.set_index(scope, 0, v);
     }
     Ok(async move {
-      stream.clone().write_msg_bytes(&serialized).await?;
+      let cancel = stream.cancel.clone();
+      let result = stream
+        .clone()
+        .write_msg_bytes(&serialized)
+        .or_cancel(cancel)
+        .await;
+      // adjust count even on error
       stream
         .queued_bytes
         .fetch_sub(serialized.len(), std::sync::atomic::Ordering::Relaxed);
+      result??;
       Ok(())
     })
   }
@@ -239,12 +252,12 @@ mod impl_ {
   pub async fn op_node_ipc_read(
     state: Rc<RefCell<OpState>>,
     #[smi] rid: ResourceId,
-  ) -> Result<serde_json::Value, AnyError> {
+  ) -> Result<serde_json::Value, IpcError> {
     let stream = state
       .borrow()
       .resource_table
       .get::<IpcJsonStreamResource>(rid)
-      .map_err(|_| bad_resource_id())?;
+      .map_err(IpcError::Resource)?;
 
     let cancel = stream.cancel.clone();
     let mut stream = RcRef::map(stream, |r| &r.read_half).borrow_mut().await;
@@ -400,7 +413,7 @@ mod impl_ {
     async fn write_msg_bytes(
       self: Rc<Self>,
       msg: &[u8],
-    ) -> Result<(), AnyError> {
+    ) -> Result<(), io::Error> {
       let mut write_half =
         RcRef::map(self, |r| &r.write_half).borrow_mut().await;
       write_half.write_all(msg).await?;
@@ -455,6 +468,14 @@ mod impl_ {
     }
   }
 
+  #[derive(Debug, thiserror::Error)]
+  pub enum IpcJsonStreamError {
+    #[error("{0}")]
+    Io(#[source] std::io::Error),
+    #[error("{0}")]
+    SimdJson(#[source] simd_json::Error),
+  }
+
   // JSON serialization stream over IPC pipe.
   //
   // `\n` is used as a delimiter between messages.
@@ -475,7 +496,7 @@ mod impl_ {
 
     async fn read_msg(
       &mut self,
-    ) -> Result<Option<serde_json::Value>, AnyError> {
+    ) -> Result<Option<serde_json::Value>, IpcJsonStreamError> {
       let mut json = None;
       let nread = read_msg_inner(
         &mut self.pipe,
@@ -483,7 +504,8 @@ mod impl_ {
         &mut json,
         &mut self.read_buffer,
       )
-      .await?;
+      .await
+      .map_err(IpcJsonStreamError::Io)?;
       if nread == 0 {
         // EOF.
         return Ok(None);
@@ -493,7 +515,8 @@ mod impl_ {
         Some(v) => v,
         None => {
           // Took more than a single read and some buffering.
-          simd_json::from_slice(&mut self.buffer[..nread])?
+          simd_json::from_slice(&mut self.buffer[..nread])
+            .map_err(IpcJsonStreamError::SimdJson)?
         }
       };
 
diff --git a/ext/node/ops/mod.rs b/ext/node/ops/mod.rs
index b562261f39..b53f19dc23 100644
--- a/ext/node/ops/mod.rs
+++ b/ext/node/ops/mod.rs
@@ -7,6 +7,7 @@ pub mod fs;
 pub mod http;
 pub mod http2;
 pub mod idna;
+pub mod inspector;
 pub mod ipc;
 pub mod os;
 pub mod process;
diff --git a/ext/node/ops/os/mod.rs b/ext/node/ops/os/mod.rs
index ca91895f22..d291277ad4 100644
--- a/ext/node/ops/os/mod.rs
+++ b/ext/node/ops/os/mod.rs
@@ -1,19 +1,31 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
+use std::mem::MaybeUninit;
+
 use crate::NodePermissions;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 
 mod cpus;
-mod priority;
+pub mod priority;
+
+#[derive(Debug, thiserror::Error)]
+pub enum OsError {
+  #[error(transparent)]
+  Priority(priority::PriorityError),
+  #[error(transparent)]
+  Permission(#[from] deno_permissions::PermissionCheckError),
+  #[error("Failed to get cpu info")]
+  FailedToGetCpuInfo,
+  #[error("Failed to get user info")]
+  FailedToGetUserInfo(#[source] std::io::Error),
+}
 
 #[op2(fast)]
 pub fn op_node_os_get_priority<P>(
   state: &mut OpState,
   pid: u32,
-) -> Result<i32, AnyError>
+) -> Result<i32, OsError>
 where
   P: NodePermissions + 'static,
 {
@@ -22,7 +34,7 @@ where
     permissions.check_sys("getPriority", "node:os.getPriority()")?;
   }
 
-  priority::get_priority(pid)
+  priority::get_priority(pid).map_err(OsError::Priority)
 }
 
 #[op2(fast)]
@@ -30,7 +42,7 @@ pub fn op_node_os_set_priority<P>(
   state: &mut OpState,
   pid: u32,
   priority: i32,
-) -> Result<(), AnyError>
+) -> Result<(), OsError>
 where
   P: NodePermissions + 'static,
 {
@@ -39,25 +51,171 @@ where
     permissions.check_sys("setPriority", "node:os.setPriority()")?;
   }
 
-  priority::set_priority(pid, priority)
+  priority::set_priority(pid, priority).map_err(OsError::Priority)
+}
+
+#[derive(serde::Serialize)]
+pub struct UserInfo {
+  username: String,
+  homedir: String,
+  shell: Option<String>,
+}
+
+#[cfg(unix)]
+fn get_user_info(uid: u32) -> Result<UserInfo, OsError> {
+  use std::ffi::CStr;
+  let mut pw: MaybeUninit<libc::passwd> = MaybeUninit::uninit();
+  let mut result: *mut libc::passwd = std::ptr::null_mut();
+  // SAFETY: libc call, no invariants
+  let max_buf_size = unsafe { libc::sysconf(libc::_SC_GETPW_R_SIZE_MAX) };
+  let buf_size = if max_buf_size < 0 {
+    // from the man page
+    16_384
+  } else {
+    max_buf_size as usize
+  };
+  let mut buf = {
+    let mut b = Vec::<MaybeUninit<libc::c_char>>::with_capacity(buf_size);
+    // SAFETY: MaybeUninit has no initialization invariants, and len == cap
+    unsafe {
+      b.set_len(buf_size);
+    }
+    b
+  };
+  // SAFETY: libc call, args are correct
+  let s = unsafe {
+    libc::getpwuid_r(
+      uid,
+      pw.as_mut_ptr(),
+      buf.as_mut_ptr().cast(),
+      buf_size,
+      std::ptr::addr_of_mut!(result),
+    )
+  };
+  if result.is_null() {
+    if s != 0 {
+      return Err(
+        OsError::FailedToGetUserInfo(std::io::Error::last_os_error()),
+      );
+    } else {
+      return Err(OsError::FailedToGetUserInfo(std::io::Error::from(
+        std::io::ErrorKind::NotFound,
+      )));
+    }
+  }
+  // SAFETY: pw was initialized by the call to `getpwuid_r` above
+  let pw = unsafe { pw.assume_init() };
+  // SAFETY: initialized above, pw alive until end of function, nul terminated
+  let username = unsafe { CStr::from_ptr(pw.pw_name) };
+  // SAFETY: initialized above, pw alive until end of function, nul terminated
+  let homedir = unsafe { CStr::from_ptr(pw.pw_dir) };
+  // SAFETY: initialized above, pw alive until end of function, nul terminated
+  let shell = unsafe { CStr::from_ptr(pw.pw_shell) };
+  Ok(UserInfo {
+    username: username.to_string_lossy().into_owned(),
+    homedir: homedir.to_string_lossy().into_owned(),
+    shell: Some(shell.to_string_lossy().into_owned()),
+  })
+}
+
+#[cfg(windows)]
+fn get_user_info(_uid: u32) -> Result<UserInfo, OsError> {
+  use std::ffi::OsString;
+  use std::os::windows::ffi::OsStringExt;
+
+  use windows_sys::Win32::Foundation::CloseHandle;
+  use windows_sys::Win32::Foundation::GetLastError;
+  use windows_sys::Win32::Foundation::ERROR_INSUFFICIENT_BUFFER;
+  use windows_sys::Win32::Foundation::HANDLE;
+  use windows_sys::Win32::System::Threading::GetCurrentProcess;
+  use windows_sys::Win32::System::Threading::OpenProcessToken;
+  use windows_sys::Win32::UI::Shell::GetUserProfileDirectoryW;
+  struct Handle(HANDLE);
+  impl Drop for Handle {
+    fn drop(&mut self) {
+      // SAFETY: win32 call
+      unsafe {
+        CloseHandle(self.0);
+      }
+    }
+  }
+  let mut token: MaybeUninit<HANDLE> = MaybeUninit::uninit();
+
+  // Get a handle to the current process
+  // SAFETY: win32 call
+  unsafe {
+    if OpenProcessToken(
+      GetCurrentProcess(),
+      windows_sys::Win32::Security::TOKEN_READ,
+      token.as_mut_ptr(),
+    ) == 0
+    {
+      return Err(
+        OsError::FailedToGetUserInfo(std::io::Error::last_os_error()),
+      );
+    }
+  }
+
+  // SAFETY: initialized by call above
+  let token = Handle(unsafe { token.assume_init() });
+
+  let mut bufsize = 0;
+  // get the size for the homedir buf (it'll end up in `bufsize`)
+  // SAFETY: win32 call
+  unsafe {
+    GetUserProfileDirectoryW(token.0, std::ptr::null_mut(), &mut bufsize);
+    let err = GetLastError();
+    if err != ERROR_INSUFFICIENT_BUFFER {
+      return Err(OsError::FailedToGetUserInfo(
+        std::io::Error::from_raw_os_error(err as i32),
+      ));
+    }
+  }
+  let mut path = vec![0; bufsize as usize];
+  // Actually get the homedir
+  // SAFETY: path is `bufsize` elements
+  unsafe {
+    if GetUserProfileDirectoryW(token.0, path.as_mut_ptr(), &mut bufsize) == 0 {
+      return Err(
+        OsError::FailedToGetUserInfo(std::io::Error::last_os_error()),
+      );
+    }
+  }
+  // remove trailing nul
+  path.pop();
+  let homedir_wide = OsString::from_wide(&path);
+  let homedir = homedir_wide.to_string_lossy().into_owned();
+
+  Ok(UserInfo {
+    username: deno_whoami::username(),
+    homedir,
+    shell: None,
+  })
 }
 
 #[op2]
-#[string]
-pub fn op_node_os_username<P>(state: &mut OpState) -> Result<String, AnyError>
+#[serde]
+pub fn op_node_os_user_info<P>(
+  state: &mut OpState,
+  #[smi] uid: u32,
+) -> Result<UserInfo, OsError>
 where
   P: NodePermissions + 'static,
 {
   {
     let permissions = state.borrow_mut::<P>();
-    permissions.check_sys("username", "node:os.userInfo()")?;
+    permissions
+      .check_sys("userInfo", "node:os.userInfo()")
+      .map_err(OsError::Permission)?;
   }
 
-  Ok(deno_whoami::username())
+  get_user_info(uid)
 }
 
 #[op2(fast)]
-pub fn op_geteuid<P>(state: &mut OpState) -> Result<u32, AnyError>
+pub fn op_geteuid<P>(
+  state: &mut OpState,
+) -> Result<u32, deno_core::error::AnyError>
 where
   P: NodePermissions + 'static,
 {
@@ -76,7 +234,9 @@ where
 }
 
 #[op2(fast)]
-pub fn op_getegid<P>(state: &mut OpState) -> Result<u32, AnyError>
+pub fn op_getegid<P>(
+  state: &mut OpState,
+) -> Result<u32, deno_core::error::AnyError>
 where
   P: NodePermissions + 'static,
 {
@@ -96,7 +256,7 @@ where
 
 #[op2]
 #[serde]
-pub fn op_cpus<P>(state: &mut OpState) -> Result<Vec<cpus::CpuInfo>, AnyError>
+pub fn op_cpus<P>(state: &mut OpState) -> Result<Vec<cpus::CpuInfo>, OsError>
 where
   P: NodePermissions + 'static,
 {
@@ -105,12 +265,14 @@ where
     permissions.check_sys("cpus", "node:os.cpus()")?;
   }
 
-  cpus::cpu_info().ok_or_else(|| type_error("Failed to get cpu info"))
+  cpus::cpu_info().ok_or(OsError::FailedToGetCpuInfo)
 }
 
 #[op2]
 #[string]
-pub fn op_homedir<P>(state: &mut OpState) -> Result<Option<String>, AnyError>
+pub fn op_homedir<P>(
+  state: &mut OpState,
+) -> Result<Option<String>, deno_core::error::AnyError>
 where
   P: NodePermissions + 'static,
 {
diff --git a/ext/node/ops/os/priority.rs b/ext/node/ops/os/priority.rs
index 043928e2a6..9a1ebcca70 100644
--- a/ext/node/ops/os/priority.rs
+++ b/ext/node/ops/os/priority.rs
@@ -1,12 +1,18 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
-
 pub use impl_::*;
 
+#[derive(Debug, thiserror::Error)]
+pub enum PriorityError {
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[cfg(windows)]
+  #[error("Invalid priority")]
+  InvalidPriority,
+}
+
 #[cfg(unix)]
 mod impl_ {
-  use super::*;
   use errno::errno;
   use errno::set_errno;
   use errno::Errno;
@@ -16,7 +22,7 @@ mod impl_ {
   const PRIORITY_HIGH: i32 = -14;
 
   // Ref: https://github.com/libuv/libuv/blob/55376b044b74db40772e8a6e24d67a8673998e02/src/unix/core.c#L1533-L1547
-  pub fn get_priority(pid: u32) -> Result<i32, AnyError> {
+  pub fn get_priority(pid: u32) -> Result<i32, super::PriorityError> {
     set_errno(Errno(0));
     match (
       // SAFETY: libc::getpriority is unsafe
@@ -29,7 +35,10 @@ mod impl_ {
     }
   }
 
-  pub fn set_priority(pid: u32, priority: i32) -> Result<(), AnyError> {
+  pub fn set_priority(
+    pid: u32,
+    priority: i32,
+  ) -> Result<(), super::PriorityError> {
     // SAFETY: libc::setpriority is unsafe
     match unsafe { libc::setpriority(PRIO_PROCESS, pid as id_t, priority) } {
       -1 => Err(std::io::Error::last_os_error().into()),
@@ -40,8 +49,6 @@ mod impl_ {
 
 #[cfg(windows)]
 mod impl_ {
-  use super::*;
-  use deno_core::error::type_error;
   use winapi::shared::minwindef::DWORD;
   use winapi::shared::minwindef::FALSE;
   use winapi::shared::ntdef::NULL;
@@ -67,7 +74,7 @@ mod impl_ {
   const PRIORITY_HIGHEST: i32 = -20;
 
   // Ported from: https://github.com/libuv/libuv/blob/a877ca2435134ef86315326ef4ef0c16bdbabf17/src/win/util.c#L1649-L1685
-  pub fn get_priority(pid: u32) -> Result<i32, AnyError> {
+  pub fn get_priority(pid: u32) -> Result<i32, super::PriorityError> {
     // SAFETY: Windows API calls
     unsafe {
       let handle = if pid == 0 {
@@ -95,7 +102,10 @@ mod impl_ {
   }
 
   // Ported from: https://github.com/libuv/libuv/blob/a877ca2435134ef86315326ef4ef0c16bdbabf17/src/win/util.c#L1688-L1719
-  pub fn set_priority(pid: u32, priority: i32) -> Result<(), AnyError> {
+  pub fn set_priority(
+    pid: u32,
+    priority: i32,
+  ) -> Result<(), super::PriorityError> {
     // SAFETY: Windows API calls
     unsafe {
       let handle = if pid == 0 {
@@ -109,7 +119,7 @@ mod impl_ {
         #[allow(clippy::manual_range_contains)]
         let priority_class =
           if priority < PRIORITY_HIGHEST || priority > PRIORITY_LOW {
-            return Err(type_error("Invalid priority"));
+            return Err(super::PriorityError::InvalidPriority);
           } else if priority < PRIORITY_HIGH {
             REALTIME_PRIORITY_CLASS
           } else if priority < PRIORITY_ABOVE_NORMAL {
diff --git a/ext/node/ops/process.rs b/ext/node/ops/process.rs
index 0992c46c62..282567226e 100644
--- a/ext/node/ops/process.rs
+++ b/ext/node/ops/process.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_permissions::PermissionsContainer;
@@ -51,7 +50,7 @@ pub fn op_node_process_kill(
   state: &mut OpState,
   #[smi] pid: i32,
   #[smi] sig: i32,
-) -> Result<i32, AnyError> {
+) -> Result<i32, deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_run_all("process.kill")?;
diff --git a/ext/node/ops/require.rs b/ext/node/ops/require.rs
index 3578719d0c..e381ee91d4 100644
--- a/ext/node/ops/require.rs
+++ b/ext/node/ops/require.rs
@@ -1,40 +1,73 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::anyhow::Context;
-use deno_core::error::generic_error;
 use deno_core::error::AnyError;
-use deno_core::normalize_path;
 use deno_core::op2;
 use deno_core::url::Url;
 use deno_core::v8;
 use deno_core::JsRuntimeInspector;
-use deno_core::ModuleSpecifier;
 use deno_core::OpState;
 use deno_fs::FileSystemRc;
+use deno_package_json::NodeModuleKind;
 use deno_package_json::PackageJsonRc;
-use node_resolver::NodeModuleKind;
+use deno_path_util::normalize_path;
+use deno_path_util::url_from_file_path;
+use deno_path_util::url_to_file_path;
+use node_resolver::errors::ClosestPkgJsonError;
 use node_resolver::NodeResolutionMode;
 use node_resolver::REQUIRE_CONDITIONS;
+use std::borrow::Cow;
 use std::cell::RefCell;
 use std::path::Path;
 use std::path::PathBuf;
 use std::rc::Rc;
 
 use crate::NodePermissions;
-use crate::NodeRequireResolverRc;
+use crate::NodeRequireLoaderRc;
 use crate::NodeResolverRc;
-use crate::NpmResolverRc;
+use crate::NpmPackageFolderResolverRc;
+use crate::PackageJsonResolverRc;
 
-fn ensure_read_permission<P>(
+#[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
+fn ensure_read_permission<'a, P>(
   state: &mut OpState,
-  file_path: &Path,
-) -> Result<(), AnyError>
+  file_path: &'a Path,
+) -> Result<Cow<'a, Path>, deno_core::error::AnyError>
 where
   P: NodePermissions + 'static,
 {
-  let resolver = state.borrow::<NodeRequireResolverRc>().clone();
+  let loader = state.borrow::<NodeRequireLoaderRc>().clone();
   let permissions = state.borrow_mut::<P>();
-  resolver.ensure_read_permission(permissions, file_path)
+  loader.ensure_read_permission(permissions, file_path)
+}
+
+#[derive(Debug, thiserror::Error)]
+pub enum RequireError {
+  #[error(transparent)]
+  UrlParse(#[from] url::ParseError),
+  #[error(transparent)]
+  Permission(deno_core::error::AnyError),
+  #[error(transparent)]
+  PackageExportsResolve(
+    #[from] node_resolver::errors::PackageExportsResolveError,
+  ),
+  #[error(transparent)]
+  PackageJsonLoad(#[from] node_resolver::errors::PackageJsonLoadError),
+  #[error(transparent)]
+  ClosestPkgJson(#[from] node_resolver::errors::ClosestPkgJsonError),
+  #[error(transparent)]
+  PackageImportsResolve(
+    #[from] node_resolver::errors::PackageImportsResolveError,
+  ),
+  #[error(transparent)]
+  FilePathConversion(#[from] deno_path_util::UrlToFilePathError),
+  #[error(transparent)]
+  UrlConversion(#[from] deno_path_util::PathToUrlError),
+  #[error(transparent)]
+  Fs(#[from] deno_io::fs::FsError),
+  #[error(transparent)]
+  ReadModule(deno_core::error::AnyError),
+  #[error("Unable to get CWD: {0}")]
+  UnableToGetCwd(deno_io::fs::FsError),
 }
 
 #[op2]
@@ -93,7 +126,7 @@ pub fn op_require_init_paths() -> Vec<String> {
 pub fn op_require_node_module_paths<P>(
   state: &mut OpState,
   #[string] from: String,
-) -> Result<Vec<String>, AnyError>
+) -> Result<Vec<String>, RequireError>
 where
   P: NodePermissions + 'static,
 {
@@ -102,13 +135,10 @@ where
   let from = if from.starts_with("file:///") {
     url_to_file_path(&Url::parse(&from)?)?
   } else {
-    let current_dir =
-      &(fs.cwd().map_err(AnyError::from)).context("Unable to get CWD")?;
-    deno_core::normalize_path(current_dir.join(from))
+    let current_dir = &fs.cwd().map_err(RequireError::UnableToGetCwd)?;
+    normalize_path(current_dir.join(from))
   };
 
-  ensure_read_permission::<P>(state, &from)?;
-
   if cfg!(windows) {
     // return root node_modules when path is 'D:\\'.
     let from_str = from.to_str().unwrap();
@@ -189,17 +219,17 @@ pub fn op_require_resolve_deno_dir(
   state: &mut OpState,
   #[string] request: String,
   #[string] parent_filename: String,
-) -> Option<String> {
-  let resolver = state.borrow::<NpmResolverRc>();
-  resolver
-    .resolve_package_folder_from_package(
-      &request,
-      &ModuleSpecifier::from_file_path(&parent_filename).unwrap_or_else(|_| {
-        panic!("Url::from_file_path: [{:?}]", parent_filename)
-      }),
-    )
-    .ok()
-    .map(|p| p.to_string_lossy().into_owned())
+) -> Result<Option<String>, AnyError> {
+  let resolver = state.borrow::<NpmPackageFolderResolverRc>();
+  Ok(
+    resolver
+      .resolve_package_folder_from_package(
+        &request,
+        &url_from_file_path(&PathBuf::from(parent_filename))?,
+      )
+      .ok()
+      .map(|p| p.to_string_lossy().into_owned()),
+  )
 }
 
 #[op2(fast)]
@@ -207,8 +237,11 @@ pub fn op_require_is_deno_dir_package(
   state: &mut OpState,
   #[string] path: String,
 ) -> bool {
-  let resolver = state.borrow::<NpmResolverRc>();
-  resolver.in_npm_package_at_file_path(&PathBuf::from(path))
+  let resolver = state.borrow::<NodeResolverRc>();
+  match deno_path_util::url_from_file_path(&PathBuf::from(path)) {
+    Ok(specifier) => resolver.in_npm_package(&specifier),
+    Err(_) => false,
+  }
 }
 
 #[op2]
@@ -262,12 +295,12 @@ pub fn op_require_path_is_absolute(#[string] p: String) -> bool {
 pub fn op_require_stat<P>(
   state: &mut OpState,
   #[string] path: String,
-) -> Result<i32, AnyError>
+) -> Result<i32, deno_core::error::AnyError>
 where
   P: NodePermissions + 'static,
 {
   let path = PathBuf::from(path);
-  ensure_read_permission::<P>(state, &path)?;
+  let path = ensure_read_permission::<P>(state, &path)?;
   let fs = state.borrow::<FileSystemRc>();
   if let Ok(metadata) = fs.stat_sync(&path) {
     if metadata.is_file {
@@ -285,15 +318,16 @@ where
 pub fn op_require_real_path<P>(
   state: &mut OpState,
   #[string] request: String,
-) -> Result<String, AnyError>
+) -> Result<String, RequireError>
 where
   P: NodePermissions + 'static,
 {
   let path = PathBuf::from(request);
-  ensure_read_permission::<P>(state, &path)?;
+  let path = ensure_read_permission::<P>(state, &path)
+    .map_err(RequireError::Permission)?;
   let fs = state.borrow::<FileSystemRc>();
   let canonicalized_path =
-    deno_core::strip_unc_prefix(fs.realpath_sync(&path)?);
+    deno_path_util::strip_unc_prefix(fs.realpath_sync(&path)?);
   Ok(canonicalized_path.to_string_lossy().into_owned())
 }
 
@@ -317,12 +351,14 @@ pub fn op_require_path_resolve(#[serde] parts: Vec<String>) -> String {
 #[string]
 pub fn op_require_path_dirname(
   #[string] request: String,
-) -> Result<String, AnyError> {
+) -> Result<String, deno_core::error::AnyError> {
   let p = PathBuf::from(request);
   if let Some(parent) = p.parent() {
     Ok(parent.to_string_lossy().into_owned())
   } else {
-    Err(generic_error("Path doesn't have a parent"))
+    Err(deno_core::error::generic_error(
+      "Path doesn't have a parent",
+    ))
   }
 }
 
@@ -330,12 +366,14 @@ pub fn op_require_path_dirname(
 #[string]
 pub fn op_require_path_basename(
   #[string] request: String,
-) -> Result<String, AnyError> {
+) -> Result<String, deno_core::error::AnyError> {
   let p = PathBuf::from(request);
   if let Some(path) = p.file_name() {
     Ok(path.to_string_lossy().into_owned())
   } else {
-    Err(generic_error("Path doesn't have a file name"))
+    Err(deno_core::error::generic_error(
+      "Path doesn't have a file name",
+    ))
   }
 }
 
@@ -346,7 +384,7 @@ pub fn op_require_try_self_parent_path<P>(
   has_parent: bool,
   #[string] maybe_parent_filename: Option<String>,
   #[string] maybe_parent_id: Option<String>,
-) -> Result<Option<String>, AnyError>
+) -> Result<Option<String>, deno_core::error::AnyError>
 where
   P: NodePermissions + 'static,
 {
@@ -362,7 +400,7 @@ where
     if parent_id == "<repl>" || parent_id == "internal/preload" {
       let fs = state.borrow::<FileSystemRc>();
       if let Ok(cwd) = fs.cwd() {
-        ensure_read_permission::<P>(state, &cwd)?;
+        let cwd = ensure_read_permission::<P>(state, &cwd)?;
         return Ok(Some(cwd.to_string_lossy().into_owned()));
       }
     }
@@ -376,7 +414,7 @@ pub fn op_require_try_self<P>(
   state: &mut OpState,
   #[string] parent_path: Option<String>,
   #[string] request: String,
-) -> Result<Option<String>, AnyError>
+) -> Result<Option<String>, RequireError>
 where
   P: NodePermissions + 'static,
 {
@@ -384,8 +422,8 @@ where
     return Ok(None);
   }
 
-  let node_resolver = state.borrow::<NodeResolverRc>();
-  let pkg = node_resolver
+  let pkg_json_resolver = state.borrow::<PackageJsonResolverRc>();
+  let pkg = pkg_json_resolver
     .get_closest_package_json_from_path(&PathBuf::from(parent_path.unwrap()))
     .ok()
     .flatten();
@@ -414,6 +452,7 @@ where
 
   let referrer = deno_core::url::Url::from_file_path(&pkg.path).unwrap();
   if let Some(exports) = &pkg.exports {
+    let node_resolver = state.borrow::<NodeResolverRc>();
     let r = node_resolver.package_exports_resolve(
       &pkg.path,
       &expansion,
@@ -438,14 +477,18 @@ where
 pub fn op_require_read_file<P>(
   state: &mut OpState,
   #[string] file_path: String,
-) -> Result<String, AnyError>
+) -> Result<String, RequireError>
 where
   P: NodePermissions + 'static,
 {
   let file_path = PathBuf::from(file_path);
-  ensure_read_permission::<P>(state, &file_path)?;
-  let fs = state.borrow::<FileSystemRc>();
-  Ok(fs.read_text_file_lossy_sync(&file_path, None)?)
+  // todo(dsherret): there's multiple borrows to NodeRequireLoaderRc here
+  let file_path = ensure_read_permission::<P>(state, &file_path)
+    .map_err(RequireError::Permission)?;
+  let loader = state.borrow::<NodeRequireLoaderRc>();
+  loader
+    .load_text_file_lossy(&file_path)
+    .map_err(RequireError::ReadModule)
 }
 
 #[op2]
@@ -470,16 +513,17 @@ pub fn op_require_resolve_exports<P>(
   #[string] name: String,
   #[string] expansion: String,
   #[string] parent_path: String,
-) -> Result<Option<String>, AnyError>
+) -> Result<Option<String>, RequireError>
 where
   P: NodePermissions + 'static,
 {
   let fs = state.borrow::<FileSystemRc>();
-  let npm_resolver = state.borrow::<NpmResolverRc>();
   let node_resolver = state.borrow::<NodeResolverRc>();
+  let pkg_json_resolver = state.borrow::<PackageJsonResolverRc>();
 
   let modules_path = PathBuf::from(&modules_path_str);
-  let pkg_path = if npm_resolver.in_npm_package_at_file_path(&modules_path)
+  let modules_specifier = deno_path_util::url_from_file_path(&modules_path)?;
+  let pkg_path = if node_resolver.in_npm_package(&modules_specifier)
     && !uses_local_node_modules_dir
   {
     modules_path
@@ -493,7 +537,7 @@ where
     }
   };
   let Some(pkg) =
-    node_resolver.load_package_json(&pkg_path.join("package.json"))?
+    pkg_json_resolver.load_package_json(&pkg_path.join("package.json"))?
   else {
     return Ok(None);
   };
@@ -501,12 +545,16 @@ where
     return Ok(None);
   };
 
-  let referrer = Url::from_file_path(parent_path).unwrap();
+  let referrer = if parent_path.is_empty() {
+    None
+  } else {
+    Some(Url::from_file_path(parent_path).unwrap())
+  };
   let r = node_resolver.package_exports_resolve(
     &pkg.path,
     &format!(".{expansion}"),
     exports,
-    Some(&referrer),
+    referrer.as_ref(),
     NodeModuleKind::Cjs,
     REQUIRE_CONDITIONS,
     NodeResolutionMode::Execution,
@@ -518,21 +566,17 @@ where
   }))
 }
 
-#[op2]
-#[serde]
-pub fn op_require_read_closest_package_json<P>(
+#[op2(fast)]
+pub fn op_require_is_maybe_cjs(
   state: &mut OpState,
   #[string] filename: String,
-) -> Result<Option<PackageJsonRc>, AnyError>
-where
-  P: NodePermissions + 'static,
-{
+) -> Result<bool, ClosestPkgJsonError> {
   let filename = PathBuf::from(filename);
-  ensure_read_permission::<P>(state, filename.parent().unwrap())?;
-  let node_resolver = state.borrow::<NodeResolverRc>().clone();
-  node_resolver
-    .get_closest_package_json_from_path(&filename)
-    .map_err(AnyError::from)
+  let Ok(url) = url_from_file_path(&filename) else {
+    return Ok(false);
+  };
+  let loader = state.borrow::<NodeRequireLoaderRc>();
+  loader.is_maybe_cjs(&url)
 }
 
 #[op2]
@@ -544,13 +588,13 @@ pub fn op_require_read_package_scope<P>(
 where
   P: NodePermissions + 'static,
 {
-  let node_resolver = state.borrow::<NodeResolverRc>().clone();
+  let pkg_json_resolver = state.borrow::<PackageJsonResolverRc>();
   let package_json_path = PathBuf::from(package_json_path);
   if package_json_path.file_name() != Some("package.json".as_ref()) {
     // permissions: do not allow reading a non-package.json file
     return None;
   }
-  node_resolver
+  pkg_json_resolver
     .load_package_json(&package_json_path)
     .ok()
     .flatten()
@@ -562,22 +606,23 @@ pub fn op_require_package_imports_resolve<P>(
   state: &mut OpState,
   #[string] referrer_filename: String,
   #[string] request: String,
-) -> Result<Option<String>, AnyError>
+) -> Result<Option<String>, RequireError>
 where
   P: NodePermissions + 'static,
 {
   let referrer_path = PathBuf::from(&referrer_filename);
-  ensure_read_permission::<P>(state, &referrer_path)?;
-  let node_resolver = state.borrow::<NodeResolverRc>();
+  let referrer_path = ensure_read_permission::<P>(state, &referrer_path)
+    .map_err(RequireError::Permission)?;
+  let pkg_json_resolver = state.borrow::<PackageJsonResolverRc>();
   let Some(pkg) =
-    node_resolver.get_closest_package_json_from_path(&referrer_path)?
+    pkg_json_resolver.get_closest_package_json_from_path(&referrer_path)?
   else {
     return Ok(None);
   };
 
   if pkg.imports.is_some() {
-    let referrer_url =
-      deno_core::url::Url::from_file_path(&referrer_filename).unwrap();
+    let node_resolver = state.borrow::<NodeResolverRc>();
+    let referrer_url = Url::from_file_path(&referrer_filename).unwrap();
     let url = node_resolver.package_imports_resolve(
       &request,
       Some(&referrer_url),
@@ -602,20 +647,11 @@ pub fn op_require_break_on_next_statement(state: Rc<RefCell<OpState>>) {
   inspector.wait_for_session_and_break_on_next_statement()
 }
 
-fn url_to_file_path_string(url: &Url) -> Result<String, AnyError> {
+fn url_to_file_path_string(url: &Url) -> Result<String, RequireError> {
   let file_path = url_to_file_path(url)?;
   Ok(file_path.to_string_lossy().into_owned())
 }
 
-fn url_to_file_path(url: &Url) -> Result<PathBuf, AnyError> {
-  match url.to_file_path() {
-    Ok(file_path) => Ok(file_path),
-    Err(()) => {
-      deno_core::anyhow::bail!("failed to convert '{}' to file path", url)
-    }
-  }
-}
-
 #[op2(fast)]
 pub fn op_require_can_parse_as_esm(
   scope: &mut v8::HandleScope,
diff --git a/ext/node/ops/util.rs b/ext/node/ops/util.rs
index 533d51c92c..1c177ac043 100644
--- a/ext/node/ops/util.rs
+++ b/ext/node/ops/util.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::ResourceHandle;
@@ -22,7 +21,7 @@ enum HandleType {
 pub fn op_node_guess_handle_type(
   state: &mut OpState,
   rid: u32,
-) -> Result<u32, AnyError> {
+) -> Result<u32, deno_core::error::AnyError> {
   let handle = state.resource_table.get_handle(rid)?;
 
   let handle_type = match handle {
diff --git a/ext/node/ops/v8.rs b/ext/node/ops/v8.rs
index 8813d2e18e..61f67f11f7 100644
--- a/ext/node/ops/v8.rs
+++ b/ext/node/ops/v8.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-use deno_core::error::generic_error;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
+
 use deno_core::op2;
 use deno_core::v8;
 use deno_core::FastString;
@@ -206,10 +204,9 @@ pub fn op_v8_write_value(
   scope: &mut v8::HandleScope,
   #[cppgc] ser: &Serializer,
   value: v8::Local<v8::Value>,
-) -> Result<(), AnyError> {
+) {
   let context = scope.get_current_context();
   ser.inner.write_value(context, value);
-  Ok(())
 }
 
 struct DeserBuffer {
@@ -271,11 +268,13 @@ pub fn op_v8_new_deserializer(
   scope: &mut v8::HandleScope,
   obj: v8::Local<v8::Object>,
   buffer: v8::Local<v8::ArrayBufferView>,
-) -> Result<Deserializer<'static>, AnyError> {
+) -> Result<Deserializer<'static>, deno_core::error::AnyError> {
   let offset = buffer.byte_offset();
   let len = buffer.byte_length();
   let backing_store = buffer.get_backing_store().ok_or_else(|| {
-    generic_error("deserialization buffer has no backing store")
+    deno_core::error::generic_error(
+      "deserialization buffer has no backing store",
+    )
   })?;
   let (buf_slice, buf_ptr) = if let Some(data) = backing_store.data() {
     // SAFETY: the offset is valid for the underlying buffer because we're getting it directly from v8
@@ -317,10 +316,10 @@ pub fn op_v8_transfer_array_buffer_de(
 #[op2(fast)]
 pub fn op_v8_read_double(
   #[cppgc] deser: &Deserializer,
-) -> Result<f64, AnyError> {
+) -> Result<f64, deno_core::error::AnyError> {
   let mut double = 0f64;
   if !deser.inner.read_double(&mut double) {
-    return Err(type_error("ReadDouble() failed"));
+    return Err(deno_core::error::type_error("ReadDouble() failed"));
   }
   Ok(double)
 }
@@ -355,10 +354,10 @@ pub fn op_v8_read_raw_bytes(
 #[op2(fast)]
 pub fn op_v8_read_uint32(
   #[cppgc] deser: &Deserializer,
-) -> Result<u32, AnyError> {
+) -> Result<u32, deno_core::error::AnyError> {
   let mut value = 0;
   if !deser.inner.read_uint32(&mut value) {
-    return Err(type_error("ReadUint32() failed"));
+    return Err(deno_core::error::type_error("ReadUint32() failed"));
   }
 
   Ok(value)
@@ -368,10 +367,10 @@ pub fn op_v8_read_uint32(
 #[serde]
 pub fn op_v8_read_uint64(
   #[cppgc] deser: &Deserializer,
-) -> Result<(u32, u32), AnyError> {
+) -> Result<(u32, u32), deno_core::error::AnyError> {
   let mut val = 0;
   if !deser.inner.read_uint64(&mut val) {
-    return Err(type_error("ReadUint64() failed"));
+    return Err(deno_core::error::type_error("ReadUint64() failed"));
   }
 
   Ok(((val >> 32) as u32, val as u32))
diff --git a/ext/node/ops/winerror.rs b/ext/node/ops/winerror.rs
index c0d66f7d0b..cb053774ef 100644
--- a/ext/node/ops/winerror.rs
+++ b/ext/node/ops/winerror.rs
@@ -62,10 +62,11 @@ pub fn op_node_sys_to_uv_error(err: i32) -> String {
     WSAEHOSTUNREACH => "EHOSTUNREACH",
     ERROR_INSUFFICIENT_BUFFER => "EINVAL",
     ERROR_INVALID_DATA => "EINVAL",
-    ERROR_INVALID_NAME => "EINVAL",
+    ERROR_INVALID_NAME => "ENOENT",
     ERROR_INVALID_PARAMETER => "EINVAL",
     WSAEINVAL => "EINVAL",
     WSAEPFNOSUPPORT => "EINVAL",
+    ERROR_NOT_A_REPARSE_POINT => "EINVAL",
     ERROR_BEGINNING_OF_MEDIA => "EIO",
     ERROR_BUS_RESET => "EIO",
     ERROR_CRC => "EIO",
diff --git a/ext/node/ops/worker_threads.rs b/ext/node/ops/worker_threads.rs
index c7ea4c52c2..d2e5758826 100644
--- a/ext/node/ops/worker_threads.rs
+++ b/ext/node/ops/worker_threads.rs
@@ -1,37 +1,56 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::generic_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::url::Url;
 use deno_core::OpState;
 use deno_fs::FileSystemRc;
-use node_resolver::NodeResolution;
+use std::borrow::Cow;
 use std::path::Path;
 use std::path::PathBuf;
 
 use crate::NodePermissions;
-use crate::NodeRequireResolverRc;
-use crate::NodeResolverRc;
+use crate::NodeRequireLoaderRc;
 
-fn ensure_read_permission<P>(
+#[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
+fn ensure_read_permission<'a, P>(
   state: &mut OpState,
-  file_path: &Path,
-) -> Result<(), AnyError>
+  file_path: &'a Path,
+) -> Result<Cow<'a, Path>, deno_core::error::AnyError>
 where
   P: NodePermissions + 'static,
 {
-  let resolver = state.borrow::<NodeRequireResolverRc>().clone();
+  let loader = state.borrow::<NodeRequireLoaderRc>().clone();
   let permissions = state.borrow_mut::<P>();
-  resolver.ensure_read_permission(permissions, file_path)
+  loader.ensure_read_permission(permissions, file_path)
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum WorkerThreadsFilenameError {
+  #[error(transparent)]
+  Permission(deno_core::error::AnyError),
+  #[error("{0}")]
+  UrlParse(#[from] url::ParseError),
+  #[error("Relative path entries must start with '.' or '..'")]
+  InvalidRelativeUrl,
+  #[error("URL from Path-String")]
+  UrlFromPathString,
+  #[error("URL to Path-String")]
+  UrlToPathString,
+  #[error("URL to Path")]
+  UrlToPath,
+  #[error("File not found [{0:?}]")]
+  FileNotFound(PathBuf),
+  #[error(transparent)]
+  Fs(#[from] deno_io::fs::FsError),
+}
+
+// todo(dsherret): we should remove this and do all this work inside op_create_worker
 #[op2]
 #[string]
 pub fn op_worker_threads_filename<P>(
   state: &mut OpState,
   #[string] specifier: String,
-) -> Result<String, AnyError>
+) -> Result<String, WorkerThreadsFilenameError>
 where
   P: NodePermissions + 'static,
 {
@@ -43,44 +62,26 @@ where
   } else {
     let path = PathBuf::from(&specifier);
     if path.is_relative() && !specifier.starts_with('.') {
-      return Err(generic_error(
-        "Relative path entries must start with '.' or '..'",
-      ));
+      return Err(WorkerThreadsFilenameError::InvalidRelativeUrl);
     }
-    ensure_read_permission::<P>(state, &path)?;
+    let path = ensure_read_permission::<P>(state, &path)
+      .map_err(WorkerThreadsFilenameError::Permission)?;
     let fs = state.borrow::<FileSystemRc>();
     let canonicalized_path =
-      deno_core::strip_unc_prefix(fs.realpath_sync(&path)?);
+      deno_path_util::strip_unc_prefix(fs.realpath_sync(&path)?);
     Url::from_file_path(canonicalized_path)
-      .map_err(|e| generic_error(format!("URL from Path-String: {:#?}", e)))?
+      .map_err(|_| WorkerThreadsFilenameError::UrlFromPathString)?
   };
   let url_path = url
     .to_file_path()
-    .map_err(|e| generic_error(format!("URL to Path-String: {:#?}", e)))?;
-  ensure_read_permission::<P>(state, &url_path)?;
+    .map_err(|_| WorkerThreadsFilenameError::UrlToPathString)?;
+  let url_path = ensure_read_permission::<P>(state, &url_path)
+    .map_err(WorkerThreadsFilenameError::Permission)?;
   let fs = state.borrow::<FileSystemRc>();
   if !fs.exists_sync(&url_path) {
-    return Err(generic_error(format!("File not found [{:?}]", url_path)));
-  }
-  let node_resolver = state.borrow::<NodeResolverRc>();
-  match node_resolver.url_to_node_resolution(url)? {
-    NodeResolution::Esm(u) => Ok(u.to_string()),
-    NodeResolution::CommonJs(u) => wrap_cjs(u),
-    NodeResolution::BuiltIn(_) => Err(generic_error("Neither ESM nor CJS")),
+    return Err(WorkerThreadsFilenameError::FileNotFound(
+      url_path.to_path_buf(),
+    ));
   }
-}
-
-///
-/// Wrap a CJS file-URL and the required setup in a stringified `data:`-URL
-///
-fn wrap_cjs(url: Url) -> Result<String, AnyError> {
-  let path = url
-    .to_file_path()
-    .map_err(|e| generic_error(format!("URL to Path: {:#?}", e)))?;
-  let filename = path.file_name().unwrap().to_string_lossy();
-  Ok(format!(
-    "data:text/javascript,import {{ createRequire }} from \"node:module\";\
-    const require = createRequire(\"{}\"); require(\"./{}\");",
-    url, filename,
-  ))
+  Ok(url.to_string())
 }
diff --git a/ext/node/ops/zlib/brotli.rs b/ext/node/ops/zlib/brotli.rs
index 3e3905fc3d..1a681ff7f7 100644
--- a/ext/node/ops/zlib/brotli.rs
+++ b/ext/node/ops/zlib/brotli.rs
@@ -9,8 +9,6 @@ use brotli::BrotliDecompressStream;
 use brotli::BrotliResult;
 use brotli::BrotliState;
 use brotli::Decompressor;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::JsBuffer;
 use deno_core::OpState;
@@ -19,7 +17,23 @@ use deno_core::ToJsBuffer;
 use std::cell::RefCell;
 use std::io::Read;
 
-fn encoder_mode(mode: u32) -> Result<BrotliEncoderMode, AnyError> {
+#[derive(Debug, thiserror::Error)]
+pub enum BrotliError {
+  #[error("Invalid encoder mode")]
+  InvalidEncoderMode,
+  #[error("Failed to compress")]
+  CompressFailed,
+  #[error("Failed to decompress")]
+  DecompressFailed,
+  #[error(transparent)]
+  Join(#[from] tokio::task::JoinError),
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("{0}")]
+  Io(std::io::Error),
+}
+
+fn encoder_mode(mode: u32) -> Result<BrotliEncoderMode, BrotliError> {
   Ok(match mode {
     0 => BrotliEncoderMode::BROTLI_MODE_GENERIC,
     1 => BrotliEncoderMode::BROTLI_MODE_TEXT,
@@ -28,7 +42,7 @@ fn encoder_mode(mode: u32) -> Result<BrotliEncoderMode, AnyError> {
     4 => BrotliEncoderMode::BROTLI_FORCE_MSB_PRIOR,
     5 => BrotliEncoderMode::BROTLI_FORCE_UTF8_PRIOR,
     6 => BrotliEncoderMode::BROTLI_FORCE_SIGNED_PRIOR,
-    _ => return Err(type_error("Invalid encoder mode")),
+    _ => return Err(BrotliError::InvalidEncoderMode),
   })
 }
 
@@ -40,7 +54,7 @@ pub fn op_brotli_compress(
   #[smi] quality: i32,
   #[smi] lgwin: i32,
   #[smi] mode: u32,
-) -> Result<usize, AnyError> {
+) -> Result<usize, BrotliError> {
   let mode = encoder_mode(mode)?;
   let mut out_size = out.len();
 
@@ -57,7 +71,7 @@ pub fn op_brotli_compress(
     &mut |_, _, _, _| (),
   );
   if result != 1 {
-    return Err(type_error("Failed to compress"));
+    return Err(BrotliError::CompressFailed);
   }
 
   Ok(out_size)
@@ -87,7 +101,7 @@ pub async fn op_brotli_compress_async(
   #[smi] quality: i32,
   #[smi] lgwin: i32,
   #[smi] mode: u32,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, BrotliError> {
   let mode = encoder_mode(mode)?;
   tokio::task::spawn_blocking(move || {
     let input = &*input;
@@ -107,7 +121,7 @@ pub async fn op_brotli_compress_async(
       &mut |_, _, _, _| (),
     );
     if result != 1 {
-      return Err(type_error("Failed to compress"));
+      return Err(BrotliError::CompressFailed);
     }
 
     out.truncate(out_size);
@@ -151,8 +165,11 @@ pub fn op_brotli_compress_stream(
   #[smi] rid: u32,
   #[buffer] input: &[u8],
   #[buffer] output: &mut [u8],
-) -> Result<usize, AnyError> {
-  let ctx = state.resource_table.get::<BrotliCompressCtx>(rid)?;
+) -> Result<usize, BrotliError> {
+  let ctx = state
+    .resource_table
+    .get::<BrotliCompressCtx>(rid)
+    .map_err(BrotliError::Resource)?;
   let mut inst = ctx.inst.borrow_mut();
   let mut output_offset = 0;
 
@@ -168,7 +185,7 @@ pub fn op_brotli_compress_stream(
     &mut |_, _, _, _| (),
   );
   if !result {
-    return Err(type_error("Failed to compress"));
+    return Err(BrotliError::CompressFailed);
   }
 
   Ok(output_offset)
@@ -180,8 +197,11 @@ pub fn op_brotli_compress_stream_end(
   state: &mut OpState,
   #[smi] rid: u32,
   #[buffer] output: &mut [u8],
-) -> Result<usize, AnyError> {
-  let ctx = state.resource_table.get::<BrotliCompressCtx>(rid)?;
+) -> Result<usize, BrotliError> {
+  let ctx = state
+    .resource_table
+    .get::<BrotliCompressCtx>(rid)
+    .map_err(BrotliError::Resource)?;
   let mut inst = ctx.inst.borrow_mut();
   let mut output_offset = 0;
 
@@ -197,13 +217,13 @@ pub fn op_brotli_compress_stream_end(
     &mut |_, _, _, _| (),
   );
   if !result {
-    return Err(type_error("Failed to compress"));
+    return Err(BrotliError::CompressFailed);
   }
 
   Ok(output_offset)
 }
 
-fn brotli_decompress(buffer: &[u8]) -> Result<ToJsBuffer, AnyError> {
+fn brotli_decompress(buffer: &[u8]) -> Result<ToJsBuffer, std::io::Error> {
   let mut output = Vec::with_capacity(4096);
   let mut decompressor = Decompressor::new(buffer, buffer.len());
   decompressor.read_to_end(&mut output)?;
@@ -214,7 +234,7 @@ fn brotli_decompress(buffer: &[u8]) -> Result<ToJsBuffer, AnyError> {
 #[serde]
 pub fn op_brotli_decompress(
   #[buffer] buffer: &[u8],
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, std::io::Error> {
   brotli_decompress(buffer)
 }
 
@@ -222,8 +242,11 @@ pub fn op_brotli_decompress(
 #[serde]
 pub async fn op_brotli_decompress_async(
   #[buffer] buffer: JsBuffer,
-) -> Result<ToJsBuffer, AnyError> {
-  tokio::task::spawn_blocking(move || brotli_decompress(&buffer)).await?
+) -> Result<ToJsBuffer, BrotliError> {
+  tokio::task::spawn_blocking(move || {
+    brotli_decompress(&buffer).map_err(BrotliError::Io)
+  })
+  .await?
 }
 
 struct BrotliDecompressCtx {
@@ -252,8 +275,11 @@ pub fn op_brotli_decompress_stream(
   #[smi] rid: u32,
   #[buffer] input: &[u8],
   #[buffer] output: &mut [u8],
-) -> Result<usize, AnyError> {
-  let ctx = state.resource_table.get::<BrotliDecompressCtx>(rid)?;
+) -> Result<usize, BrotliError> {
+  let ctx = state
+    .resource_table
+    .get::<BrotliDecompressCtx>(rid)
+    .map_err(BrotliError::Resource)?;
   let mut inst = ctx.inst.borrow_mut();
   let mut output_offset = 0;
 
@@ -268,7 +294,7 @@ pub fn op_brotli_decompress_stream(
     &mut inst,
   );
   if matches!(result, BrotliResult::ResultFailure) {
-    return Err(type_error("Failed to decompress"));
+    return Err(BrotliError::DecompressFailed);
   }
 
   Ok(output_offset)
@@ -280,8 +306,11 @@ pub fn op_brotli_decompress_stream_end(
   state: &mut OpState,
   #[smi] rid: u32,
   #[buffer] output: &mut [u8],
-) -> Result<usize, AnyError> {
-  let ctx = state.resource_table.get::<BrotliDecompressCtx>(rid)?;
+) -> Result<usize, BrotliError> {
+  let ctx = state
+    .resource_table
+    .get::<BrotliDecompressCtx>(rid)
+    .map_err(BrotliError::Resource)?;
   let mut inst = ctx.inst.borrow_mut();
   let mut output_offset = 0;
 
@@ -296,7 +325,7 @@ pub fn op_brotli_decompress_stream_end(
     &mut inst,
   );
   if matches!(result, BrotliResult::ResultFailure) {
-    return Err(type_error("Failed to decompress"));
+    return Err(BrotliError::DecompressFailed);
   }
 
   Ok(output_offset)
diff --git a/ext/node/ops/zlib/mod.rs b/ext/node/ops/zlib/mod.rs
index b1d6d21d22..991c0925d2 100644
--- a/ext/node/ops/zlib/mod.rs
+++ b/ext/node/ops/zlib/mod.rs
@@ -1,14 +1,14 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
+
 use deno_core::op2;
+use libc::c_ulong;
 use std::borrow::Cow;
 use std::cell::RefCell;
 use zlib::*;
 
 mod alloc;
 pub mod brotli;
-mod mode;
+pub mod mode;
 mod stream;
 
 use mode::Flush;
@@ -17,11 +17,11 @@ use mode::Mode;
 use self::stream::StreamWrapper;
 
 #[inline]
-fn check(condition: bool, msg: &str) -> Result<(), AnyError> {
+fn check(condition: bool, msg: &str) -> Result<(), deno_core::error::AnyError> {
   if condition {
     Ok(())
   } else {
-    Err(type_error(msg.to_string()))
+    Err(deno_core::error::type_error(msg.to_string()))
   }
 }
 
@@ -56,7 +56,7 @@ impl ZlibInner {
     out_off: u32,
     out_len: u32,
     flush: Flush,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), deno_core::error::AnyError> {
     check(self.init_done, "write before init")?;
     check(!self.write_in_progress, "write already in progress")?;
     check(!self.pending_close, "close already in progress")?;
@@ -65,11 +65,11 @@ impl ZlibInner {
 
     let next_in = input
       .get(in_off as usize..in_off as usize + in_len as usize)
-      .ok_or_else(|| type_error("invalid input range"))?
+      .ok_or_else(|| deno_core::error::type_error("invalid input range"))?
       .as_ptr() as *mut _;
     let next_out = out
       .get_mut(out_off as usize..out_off as usize + out_len as usize)
-      .ok_or_else(|| type_error("invalid output range"))?
+      .ok_or_else(|| deno_core::error::type_error("invalid output range"))?
       .as_mut_ptr();
 
     self.strm.avail_in = in_len;
@@ -81,7 +81,10 @@ impl ZlibInner {
     Ok(())
   }
 
-  fn do_write(&mut self, flush: Flush) -> Result<(), AnyError> {
+  fn do_write(
+    &mut self,
+    flush: Flush,
+  ) -> Result<(), deno_core::error::AnyError> {
     self.flush = flush;
     match self.mode {
       Mode::Deflate | Mode::Gzip | Mode::DeflateRaw => {
@@ -127,7 +130,7 @@ impl ZlibInner {
             self.mode = Mode::Inflate;
           }
         } else if next_expected_header_byte.is_some() {
-          return Err(type_error(
+          return Err(deno_core::error::type_error(
             "invalid number of gzip magic number bytes read",
           ));
         }
@@ -181,7 +184,7 @@ impl ZlibInner {
     Ok(())
   }
 
-  fn init_stream(&mut self) -> Result<(), AnyError> {
+  fn init_stream(&mut self) -> Result<(), deno_core::error::AnyError> {
     match self.mode {
       Mode::Gzip | Mode::Gunzip => self.window_bits += 16,
       Mode::Unzip => self.window_bits += 32,
@@ -199,7 +202,7 @@ impl ZlibInner {
       Mode::Inflate | Mode::Gunzip | Mode::InflateRaw | Mode::Unzip => {
         self.strm.inflate_init(self.window_bits)
       }
-      Mode::None => return Err(type_error("Unknown mode")),
+      Mode::None => return Err(deno_core::error::type_error("Unknown mode")),
     };
 
     self.write_in_progress = false;
@@ -208,7 +211,7 @@ impl ZlibInner {
     Ok(())
   }
 
-  fn close(&mut self) -> Result<bool, AnyError> {
+  fn close(&mut self) -> Result<bool, deno_core::error::AnyError> {
     if self.write_in_progress {
       self.pending_close = true;
       return Ok(false);
@@ -222,10 +225,8 @@ impl ZlibInner {
     Ok(true)
   }
 
-  fn reset_stream(&mut self) -> Result<(), AnyError> {
+  fn reset_stream(&mut self) {
     self.err = self.strm.reset(self.mode);
-
-    Ok(())
   }
 }
 
@@ -243,7 +244,7 @@ impl deno_core::Resource for Zlib {
 
 #[op2]
 #[cppgc]
-pub fn op_zlib_new(#[smi] mode: i32) -> Result<Zlib, AnyError> {
+pub fn op_zlib_new(#[smi] mode: i32) -> Result<Zlib, mode::ModeError> {
   let mode = Mode::try_from(mode)?;
 
   let inner = ZlibInner {
@@ -256,12 +257,20 @@ pub fn op_zlib_new(#[smi] mode: i32) -> Result<Zlib, AnyError> {
   })
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum ZlibError {
+  #[error("zlib not initialized")]
+  NotInitialized,
+  #[error(transparent)]
+  Mode(#[from] mode::ModeError),
+  #[error(transparent)]
+  Other(#[from] deno_core::error::AnyError),
+}
+
 #[op2(fast)]
-pub fn op_zlib_close(#[cppgc] resource: &Zlib) -> Result<(), AnyError> {
+pub fn op_zlib_close(#[cppgc] resource: &Zlib) -> Result<(), ZlibError> {
   let mut resource = resource.inner.borrow_mut();
-  let zlib = resource
-    .as_mut()
-    .ok_or_else(|| type_error("zlib not initialized"))?;
+  let zlib = resource.as_mut().ok_or(ZlibError::NotInitialized)?;
 
   // If there is a pending write, defer the close until the write is done.
   zlib.close()?;
@@ -282,11 +291,9 @@ pub fn op_zlib_write(
   #[smi] out_off: u32,
   #[smi] out_len: u32,
   #[buffer] result: &mut [u32],
-) -> Result<i32, AnyError> {
+) -> Result<i32, ZlibError> {
   let mut zlib = resource.inner.borrow_mut();
-  let zlib = zlib
-    .as_mut()
-    .ok_or_else(|| type_error("zlib not initialized"))?;
+  let zlib = zlib.as_mut().ok_or(ZlibError::NotInitialized)?;
 
   let flush = Flush::try_from(flush)?;
   zlib.start_write(input, in_off, in_len, out, out_off, out_len, flush)?;
@@ -307,11 +314,9 @@ pub fn op_zlib_init(
   #[smi] mem_level: i32,
   #[smi] strategy: i32,
   #[buffer] dictionary: &[u8],
-) -> Result<i32, AnyError> {
+) -> Result<i32, ZlibError> {
   let mut zlib = resource.inner.borrow_mut();
-  let zlib = zlib
-    .as_mut()
-    .ok_or_else(|| type_error("zlib not initialized"))?;
+  let zlib = zlib.as_mut().ok_or(ZlibError::NotInitialized)?;
 
   check((8..=15).contains(&window_bits), "invalid windowBits")?;
   check((-1..=9).contains(&level), "invalid level")?;
@@ -348,13 +353,11 @@ pub fn op_zlib_init(
 
 #[op2(fast)]
 #[smi]
-pub fn op_zlib_reset(#[cppgc] resource: &Zlib) -> Result<i32, AnyError> {
+pub fn op_zlib_reset(#[cppgc] resource: &Zlib) -> Result<i32, ZlibError> {
   let mut zlib = resource.inner.borrow_mut();
-  let zlib = zlib
-    .as_mut()
-    .ok_or_else(|| type_error("zlib not initialized"))?;
+  let zlib = zlib.as_mut().ok_or(ZlibError::NotInitialized)?;
 
-  zlib.reset_stream()?;
+  zlib.reset_stream();
 
   Ok(zlib.err)
 }
@@ -362,12 +365,10 @@ pub fn op_zlib_reset(#[cppgc] resource: &Zlib) -> Result<i32, AnyError> {
 #[op2(fast)]
 pub fn op_zlib_close_if_pending(
   #[cppgc] resource: &Zlib,
-) -> Result<(), AnyError> {
+) -> Result<(), ZlibError> {
   let pending_close = {
     let mut zlib = resource.inner.borrow_mut();
-    let zlib = zlib
-      .as_mut()
-      .ok_or_else(|| type_error("zlib not initialized"))?;
+    let zlib = zlib.as_mut().ok_or(ZlibError::NotInitialized)?;
 
     zlib.write_in_progress = false;
     zlib.pending_close
@@ -381,6 +382,15 @@ pub fn op_zlib_close_if_pending(
   Ok(())
 }
 
+#[op2(fast)]
+#[smi]
+pub fn op_zlib_crc32(#[buffer] data: &[u8], #[smi] value: u32) -> u32 {
+  // SAFETY: `data` is a valid buffer.
+  unsafe {
+    zlib::crc32(value as c_ulong, data.as_ptr(), data.len() as u32) as u32
+  }
+}
+
 #[cfg(test)]
 mod tests {
   use super::*;
diff --git a/ext/node/ops/zlib/mode.rs b/ext/node/ops/zlib/mode.rs
index 753300cc49..41565f9b11 100644
--- a/ext/node/ops/zlib/mode.rs
+++ b/ext/node/ops/zlib/mode.rs
@@ -1,19 +1,8 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-#[derive(Debug)]
-pub enum Error {
-  BadArgument,
-}
-
-impl std::fmt::Display for Error {
-  fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
-    match self {
-      Error::BadArgument => write!(f, "bad argument"),
-    }
-  }
-}
-
-impl std::error::Error for Error {}
+#[derive(Debug, thiserror::Error)]
+#[error("bad argument")]
+pub struct ModeError;
 
 macro_rules! repr_i32 {
     ($(#[$meta:meta])* $vis:vis enum $name:ident {
@@ -25,12 +14,12 @@ macro_rules! repr_i32 {
       }
 
       impl core::convert::TryFrom<i32> for $name {
-        type Error = Error;
+        type Error = ModeError;
 
         fn try_from(v: i32) -> Result<Self, Self::Error> {
           match v {
             $(x if x == $name::$vname as i32 => Ok($name::$vname),)*
-            _ => Err(Error::BadArgument),
+            _ => Err(ModeError),
           }
         }
       }
diff --git a/ext/node/polyfills/01_require.js b/ext/node/polyfills/01_require.js
index 5b0980c310..083d4e49be 100644
--- a/ext/node/polyfills/01_require.js
+++ b/ext/node/polyfills/01_require.js
@@ -11,6 +11,7 @@ import {
   op_require_can_parse_as_esm,
   op_require_init_paths,
   op_require_is_deno_dir_package,
+  op_require_is_maybe_cjs,
   op_require_is_request_relative,
   op_require_node_module_paths,
   op_require_package_imports_resolve,
@@ -19,7 +20,6 @@ import {
   op_require_path_is_absolute,
   op_require_path_resolve,
   op_require_proxy_path,
-  op_require_read_closest_package_json,
   op_require_read_file,
   op_require_read_package_scope,
   op_require_real_path,
@@ -523,17 +523,13 @@ function resolveExports(
     return;
   }
 
-  if (!parentPath) {
-    return false;
-  }
-
   return op_require_resolve_exports(
     usesLocalNodeModulesDir,
     modulesPath,
     request,
     name,
     expansion,
-    parentPath,
+    parentPath ?? "",
   ) ?? false;
 }
 
@@ -1064,23 +1060,22 @@ Module.prototype._compile = function (content, filename, format) {
   return result;
 };
 
-Module._extensions[".js"] = function (module, filename) {
-  const content = op_require_read_file(filename);
+Module._extensions[".js"] =
+  Module._extensions[".ts"] =
+  Module._extensions[".jsx"] =
+  Module._extensions[".tsx"] =
+    function (module, filename) {
+      const content = op_require_read_file(filename);
+      const format = op_require_is_maybe_cjs(filename) ? undefined : "module";
+      module._compile(content, filename, format);
+    };
 
-  let format;
-  if (StringPrototypeEndsWith(filename, ".js")) {
-    const pkg = op_require_read_closest_package_json(filename);
-    if (pkg?.type === "module") {
-      format = "module";
-    } else if (pkg?.type === "commonjs") {
-      format = "commonjs";
-    }
-  } else if (StringPrototypeEndsWith(filename, ".cjs")) {
-    format = "commonjs";
-  }
-
-  module._compile(content, filename, format);
-};
+Module._extensions[".cjs"] =
+  Module._extensions[".cts"] =
+    function (module, filename) {
+      const content = op_require_read_file(filename);
+      module._compile(content, filename, "commonjs");
+    };
 
 function loadESMFromCJS(module, filename, code) {
   const namespace = op_import_sync(
@@ -1091,7 +1086,10 @@ function loadESMFromCJS(module, filename, code) {
   module.exports = namespace;
 }
 
-Module._extensions[".mjs"] = function (module, filename) {
+Module._extensions[".mjs"] = Module._extensions[".mts"] = function (
+  module,
+  filename,
+) {
   loadESMFromCJS(module, filename);
 };
 
@@ -1212,6 +1210,24 @@ function isBuiltin(moduleName) {
     !StringPrototypeStartsWith(moduleName, "internal/");
 }
 
+function getBuiltinModule(id) {
+  if (!isBuiltin(id)) {
+    return undefined;
+  }
+
+  if (StringPrototypeStartsWith(id, "node:")) {
+    // Slice 'node:' prefix
+    id = StringPrototypeSlice(id, 5);
+  }
+
+  const mod = loadNativeModule(id, id);
+  if (mod) {
+    return mod.exports;
+  }
+
+  return undefined;
+}
+
 Module.isBuiltin = isBuiltin;
 
 Module.createRequire = createRequire;
@@ -1291,6 +1307,8 @@ export function findSourceMap(_path) {
   return undefined;
 }
 
+Module.findSourceMap = findSourceMap;
+
 /**
  * @param {string | URL} _specifier
  * @param {string | URL} _parentUrl
@@ -1304,7 +1322,7 @@ export function register(_specifier, _parentUrl, _options) {
   return undefined;
 }
 
-export { builtinModules, createRequire, isBuiltin, Module };
+export { builtinModules, createRequire, getBuiltinModule, isBuiltin, Module };
 export const _cache = Module._cache;
 export const _extensions = Module._extensions;
 export const _findPath = Module._findPath;
diff --git a/ext/node/polyfills/_fs/_fs_common.ts b/ext/node/polyfills/_fs/_fs_common.ts
index ac0bf5a551..a29548bb36 100644
--- a/ext/node/polyfills/_fs/_fs_common.ts
+++ b/ext/node/polyfills/_fs/_fs_common.ts
@@ -20,6 +20,7 @@ import {
   notImplemented,
   TextEncodings,
 } from "ext:deno_node/_utils.ts";
+import { type Buffer } from "node:buffer";
 
 export type CallbackWithError = (err: ErrnoException | null) => void;
 
diff --git a/ext/node/polyfills/_fs/_fs_copy.ts b/ext/node/polyfills/_fs/_fs_copy.ts
index 2f8ddf4fcd..0434bff4d1 100644
--- a/ext/node/polyfills/_fs/_fs_copy.ts
+++ b/ext/node/polyfills/_fs/_fs_copy.ts
@@ -53,8 +53,9 @@ export function copyFile(
     }, (e) => {
       if (e instanceof Deno.errors.NotFound) {
         Deno.copyFile(srcStr, destStr).then(() => cb(null), cb);
+      } else {
+        cb(e);
       }
-      cb(e);
     });
   } else {
     Deno.copyFile(srcStr, destStr).then(() => cb(null), cb);
@@ -83,8 +84,9 @@ export function copyFileSync(
     } catch (e) {
       if (e instanceof Deno.errors.NotFound) {
         Deno.copyFileSync(srcStr, destStr);
+      } else {
+        throw e;
       }
-      throw e;
     }
   } else {
     Deno.copyFileSync(srcStr, destStr);
diff --git a/ext/node/polyfills/_fs/_fs_open.ts b/ext/node/polyfills/_fs/_fs_open.ts
index 8bd989790b..31ca4bb619 100644
--- a/ext/node/polyfills/_fs/_fs_open.ts
+++ b/ext/node/polyfills/_fs/_fs_open.ts
@@ -147,8 +147,8 @@ export function open(
 
 export function openPromise(
   path: string | Buffer | URL,
-  flags?: openFlags = "r",
-  mode? = 0o666,
+  flags: openFlags = "r",
+  mode = 0o666,
 ): Promise<FileHandle> {
   return new Promise((resolve, reject) => {
     open(path, flags, mode, (err, fd) => {
diff --git a/ext/node/polyfills/_fs/_fs_read.ts b/ext/node/polyfills/_fs/_fs_read.ts
index dec3a8bbdf..df4f5e375d 100644
--- a/ext/node/polyfills/_fs/_fs_read.ts
+++ b/ext/node/polyfills/_fs/_fs_read.ts
@@ -173,7 +173,7 @@ export function readSync(
   validateBuffer(buffer);
 
   if (length == null) {
-    length = 0;
+    length = buffer.byteLength;
   }
 
   if (typeof offsetOrOpt === "number") {
diff --git a/ext/node/polyfills/_fs/_fs_readFile.ts b/ext/node/polyfills/_fs/_fs_readFile.ts
index 0f05ee1678..cf7e0305d8 100644
--- a/ext/node/polyfills/_fs/_fs_readFile.ts
+++ b/ext/node/polyfills/_fs/_fs_readFile.ts
@@ -19,6 +19,7 @@ import {
   TextEncodings,
 } from "ext:deno_node/_utils.ts";
 import { FsFile } from "ext:deno_fs/30_fs.js";
+import { denoErrorToNodeError } from "ext:deno_node/internal/errors.ts";
 
 function maybeDecode(data: Uint8Array, encoding: TextEncodings): string;
 function maybeDecode(
@@ -87,7 +88,7 @@ export function readFile(
       }
       const buffer = maybeDecode(data, encoding);
       (cb as BinaryCallback)(null, buffer);
-    }, (err) => cb && cb(err));
+    }, (err) => cb && cb(denoErrorToNodeError(err)));
   }
 }
 
@@ -117,7 +118,12 @@ export function readFileSync(
   opt?: FileOptionsArgument,
 ): string | Buffer {
   path = path instanceof URL ? pathFromURL(path) : path;
-  const data = Deno.readFileSync(path);
+  let data;
+  try {
+    data = Deno.readFileSync(path);
+  } catch (err) {
+    throw denoErrorToNodeError(err);
+  }
   const encoding = getEncoding(opt);
   if (encoding && encoding !== "binary") {
     const text = maybeDecode(data, encoding);
diff --git a/ext/node/polyfills/_fs/_fs_readlink.ts b/ext/node/polyfills/_fs/_fs_readlink.ts
index 5f23127982..08bea843fa 100644
--- a/ext/node/polyfills/_fs/_fs_readlink.ts
+++ b/ext/node/polyfills/_fs/_fs_readlink.ts
@@ -4,13 +4,10 @@
 // deno-lint-ignore-file prefer-primordials
 
 import { TextEncoder } from "ext:deno_web/08_text_encoding.js";
-import {
-  intoCallbackAPIWithIntercept,
-  MaybeEmpty,
-  notImplemented,
-} from "ext:deno_node/_utils.ts";
+import { MaybeEmpty, notImplemented } from "ext:deno_node/_utils.ts";
 import { pathFromURL } from "ext:deno_web/00_infra.js";
 import { promisify } from "ext:deno_node/internal/util.mjs";
+import { denoErrorToNodeError } from "ext:deno_node/internal/errors.ts";
 
 type ReadlinkCallback = (
   err: MaybeEmpty<Error>,
@@ -69,12 +66,17 @@ export function readlink(
 
   const encoding = getEncoding(optOrCallback);
 
-  intoCallbackAPIWithIntercept<string, Uint8Array | string>(
-    Deno.readLink,
-    (data: string): string | Uint8Array => maybeEncode(data, encoding),
-    cb,
-    path,
-  );
+  Deno.readLink(path).then((data: string) => {
+    const res = maybeEncode(data, encoding);
+    if (cb) cb(null, res);
+  }, (err: Error) => {
+    if (cb) {
+      (cb as (e: Error) => void)(denoErrorToNodeError(err, {
+        syscall: "readlink",
+        path,
+      }));
+    }
+  });
 }
 
 export const readlinkPromise = promisify(readlink) as (
@@ -88,5 +90,12 @@ export function readlinkSync(
 ): string | Uint8Array {
   path = path instanceof URL ? pathFromURL(path) : path;
 
-  return maybeEncode(Deno.readLinkSync(path), getEncoding(opt));
+  try {
+    return maybeEncode(Deno.readLinkSync(path), getEncoding(opt));
+  } catch (error) {
+    throw denoErrorToNodeError(error, {
+      syscall: "readlink",
+      path,
+    });
+  }
 }
diff --git a/ext/node/polyfills/_fs/_fs_readv.ts b/ext/node/polyfills/_fs/_fs_readv.ts
index 384f5e319a..2259f029ae 100644
--- a/ext/node/polyfills/_fs/_fs_readv.ts
+++ b/ext/node/polyfills/_fs/_fs_readv.ts
@@ -15,6 +15,7 @@ import { maybeCallback } from "ext:deno_node/_fs/_fs_common.ts";
 import { validateInteger } from "ext:deno_node/internal/validators.mjs";
 import * as io from "ext:deno_io/12_io.js";
 import { op_fs_seek_async, op_fs_seek_sync } from "ext:core/ops";
+import process from "node:process";
 
 type Callback = (
   err: ErrnoException | null,
diff --git a/ext/node/polyfills/_fs/_fs_stat.ts b/ext/node/polyfills/_fs/_fs_stat.ts
index c4ed82d577..507cb05eaf 100644
--- a/ext/node/polyfills/_fs/_fs_stat.ts
+++ b/ext/node/polyfills/_fs/_fs_stat.ts
@@ -290,8 +290,8 @@ export function convertFileInfoToStats(origin: Deno.FileInfo): Stats {
     isFIFO: () => false,
     isCharacterDevice: () => false,
     isSocket: () => false,
-    ctime: origin.mtime,
-    ctimeMs: origin.mtime?.getTime() || null,
+    ctime: origin.ctime,
+    ctimeMs: origin.ctime?.getTime() || null,
   });
 
   return stats;
@@ -336,9 +336,9 @@ export function convertFileInfoToBigIntStats(
     isFIFO: () => false,
     isCharacterDevice: () => false,
     isSocket: () => false,
-    ctime: origin.mtime,
-    ctimeMs: origin.mtime ? BigInt(origin.mtime.getTime()) : null,
-    ctimeNs: origin.mtime ? BigInt(origin.mtime.getTime()) * 1000000n : null,
+    ctime: origin.ctime,
+    ctimeMs: origin.ctime ? BigInt(origin.ctime.getTime()) : null,
+    ctimeNs: origin.ctime ? BigInt(origin.ctime.getTime()) * 1000000n : null,
   });
   return stats;
 }
@@ -383,7 +383,10 @@ export function stat(
 
   Deno.stat(path).then(
     (stat) => callback(null, CFISBIS(stat, options.bigint)),
-    (err) => callback(denoErrorToNodeError(err, { syscall: "stat" })),
+    (err) =>
+      callback(
+        denoErrorToNodeError(err, { syscall: "stat", path: getPathname(path) }),
+      ),
   );
 }
 
@@ -417,9 +420,16 @@ export function statSync(
       return;
     }
     if (err instanceof Error) {
-      throw denoErrorToNodeError(err, { syscall: "stat" });
+      throw denoErrorToNodeError(err, {
+        syscall: "stat",
+        path: getPathname(path),
+      });
     } else {
       throw err;
     }
   }
 }
+
+function getPathname(path: string | URL) {
+  return typeof path === "string" ? path : path.pathname;
+}
diff --git a/ext/node/polyfills/_next_tick.ts b/ext/node/polyfills/_next_tick.ts
index 5ee27728d0..af306a29c8 100644
--- a/ext/node/polyfills/_next_tick.ts
+++ b/ext/node/polyfills/_next_tick.ts
@@ -62,6 +62,8 @@ export function processTicksAndRejections() {
               callback(...args);
           }
         }
+      } catch (e) {
+        reportError(e);
       } finally {
         // FIXME(bartlomieju): Deno currently doesn't support async hooks
         // if (destroyHooksExist())
@@ -87,8 +89,7 @@ export function runNextTicks() {
   //   runMicrotasks();
   // if (!hasTickScheduled() && !hasRejectionToWarn())
   //   return;
-  if (!core.hasTickScheduled()) {
-    core.runMicrotasks();
+  if (queue.isEmpty() || !core.hasTickScheduled()) {
     return true;
   }
 
diff --git a/ext/node/polyfills/_process/streams.mjs b/ext/node/polyfills/_process/streams.mjs
index 19c1c9c182..3573956c9d 100644
--- a/ext/node/polyfills/_process/streams.mjs
+++ b/ext/node/polyfills/_process/streams.mjs
@@ -63,13 +63,22 @@ export function createWritableStdioStream(writer, name, warmup = false) {
   stream.destroySoon = stream.destroy;
   stream._isStdio = true;
   stream.once("close", () => writer?.close());
+
+  // We cannot call `writer?.isTerminal()` eagerly here
+  let getIsTTY = () => writer?.isTerminal();
+  const getColumns = () =>
+    stream._columns ||
+    (writer?.isTerminal() ? Deno.consoleSize?.().columns : undefined);
+
   ObjectDefineProperties(stream, {
     columns: {
       __proto__: null,
       enumerable: true,
       configurable: true,
-      get: () =>
-        writer?.isTerminal() ? Deno.consoleSize?.().columns : undefined,
+      get: () => getColumns(),
+      set: (value) => {
+        stream._columns = value;
+      },
     },
     rows: {
       __proto__: null,
@@ -81,7 +90,11 @@ export function createWritableStdioStream(writer, name, warmup = false) {
       __proto__: null,
       enumerable: true,
       configurable: true,
-      get: () => writer?.isTerminal(),
+      // Allow users to overwrite it
+      get: () => getIsTTY(),
+      set: (value) => {
+        getIsTTY = () => value;
+      },
     },
     getWindowSize: {
       __proto__: null,
diff --git a/ext/node/polyfills/_tls_wrap.ts b/ext/node/polyfills/_tls_wrap.ts
index a614b45df0..e36fc637e7 100644
--- a/ext/node/polyfills/_tls_wrap.ts
+++ b/ext/node/polyfills/_tls_wrap.ts
@@ -68,6 +68,7 @@ export class TLSSocket extends net.Socket {
   secureConnecting: boolean;
   _SNICallback: any;
   servername: string | null;
+  alpnProtocol: string | boolean | null;
   alpnProtocols: string[] | null;
   authorized: boolean;
   authorizationError: any;
@@ -114,6 +115,7 @@ export class TLSSocket extends net.Socket {
     this.secureConnecting = true;
     this._SNICallback = null;
     this.servername = null;
+    this.alpnProtocol = null;
     this.alpnProtocols = tlsOptions.ALPNProtocols;
     this.authorized = false;
     this.authorizationError = null;
@@ -151,10 +153,21 @@ export class TLSSocket extends net.Socket {
       handle.afterConnect = async (req: any, status: number) => {
         try {
           const conn = await Deno.startTls(handle[kStreamBaseField], options);
+          try {
+            const hs = await conn.handshake();
+            if (hs.alpnProtocol) {
+              tlssock.alpnProtocol = hs.alpnProtocol;
+            } else {
+              tlssock.alpnProtocol = false;
+            }
+          } catch {
+            // Don't interrupt "secure" event to let the first read/write
+            // operation emit the error.
+          }
           handle[kStreamBaseField] = conn;
           tlssock.emit("secure");
           tlssock.removeListener("end", onConnectEnd);
-        } catch {
+        } catch (_) {
           // TODO(kt3k): Handle this
         }
         return afterConnect.call(handle, req, status);
@@ -269,6 +282,7 @@ export class ServerImpl extends EventEmitter {
         // Creates TCP handle and socket directly from Deno.TlsConn.
         // This works as TLS socket. We don't use TLSSocket class for doing
         // this because Deno.startTls only supports client side tcp connection.
+        // TODO(@satyarohith): set TLSSocket.alpnProtocol when we use TLSSocket class.
         const handle = new TCP(TCPConstants.SOCKET, await listener.accept());
         const socket = new net.Socket({ handle });
         this.emit("secureConnection", socket);
diff --git a/ext/node/polyfills/_utils.ts b/ext/node/polyfills/_utils.ts
index b50c113e14..79d84e00f0 100644
--- a/ext/node/polyfills/_utils.ts
+++ b/ext/node/polyfills/_utils.ts
@@ -17,6 +17,7 @@ const {
 import { TextDecoder, TextEncoder } from "ext:deno_web/08_text_encoding.js";
 import { errorMap } from "ext:deno_node/internal_binding/uv.ts";
 import { codes } from "ext:deno_node/internal/error_codes.ts";
+import { ERR_NOT_IMPLEMENTED } from "ext:deno_node/internal/errors.ts";
 
 export type BinaryEncodings = "binary";
 
@@ -34,8 +35,7 @@ export type TextEncodings =
 export type Encodings = BinaryEncodings | TextEncodings;
 
 export function notImplemented(msg: string): never {
-  const message = msg ? `Not implemented: ${msg}` : "Not implemented";
-  throw new Error(message);
+  throw new ERR_NOT_IMPLEMENTED(msg);
 }
 
 export function warnNotImplemented(msg?: string) {
diff --git a/ext/node/polyfills/_zlib.mjs b/ext/node/polyfills/_zlib.mjs
index 851bd602f2..07fc440ef5 100644
--- a/ext/node/polyfills/_zlib.mjs
+++ b/ext/node/polyfills/_zlib.mjs
@@ -14,6 +14,7 @@ import { nextTick } from "ext:deno_node/_next_tick.ts";
 import {
   isAnyArrayBuffer,
   isArrayBufferView,
+  isUint8Array,
 } from "ext:deno_node/internal/util/types.ts";
 
 var kRangeErrorMessage = "Cannot create final Buffer. It would be larger " +
@@ -158,6 +159,12 @@ export const inflateRawSync = function (buffer, opts) {
 function sanitizeInput(input) {
   if (typeof input === "string") input = Buffer.from(input);
 
+  if (isArrayBufferView(input) && !isUint8Array(input)) {
+    input = Buffer.from(input.buffer, input.byteOffset, input.byteLength);
+  } else if (isAnyArrayBuffer(input)) {
+    input = Buffer.from(input);
+  }
+
   if (
     !Buffer.isBuffer(input) &&
     (input.buffer && !input.buffer.constructor === ArrayBuffer)
diff --git a/ext/node/polyfills/buffer.ts b/ext/node/polyfills/buffer.ts
index 8986cf53d7..efe3b07a97 100644
--- a/ext/node/polyfills/buffer.ts
+++ b/ext/node/polyfills/buffer.ts
@@ -13,4 +13,5 @@ export {
   kMaxLength,
   kStringMaxLength,
   SlowBuffer,
+  transcode,
 } from "ext:deno_node/internal/buffer.mjs";
diff --git a/ext/node/polyfills/child_process.ts b/ext/node/polyfills/child_process.ts
index c37dfc410a..eda718ff34 100644
--- a/ext/node/polyfills/child_process.ts
+++ b/ext/node/polyfills/child_process.ts
@@ -132,6 +132,8 @@ export function fork(
           rm = 2;
         }
         execArgv.splice(index, rm);
+      } else if (flag.startsWith("--no-warnings")) {
+        execArgv[index] = "--quiet";
       } else {
         index++;
       }
diff --git a/ext/node/polyfills/http.ts b/ext/node/polyfills/http.ts
index f3f6f86ed8..9a920adeee 100644
--- a/ext/node/polyfills/http.ts
+++ b/ext/node/polyfills/http.ts
@@ -34,6 +34,7 @@ import {
   finished,
   Readable as NodeReadable,
   Writable as NodeWritable,
+  WritableOptions as NodeWritableOptions,
 } from "node:stream";
 import {
   kUniqueHeaders,
@@ -66,12 +67,13 @@ import { headersEntries } from "ext:deno_fetch/20_headers.js";
 import { timerId } from "ext:deno_web/03_abort_signal.js";
 import { clearTimeout as webClearTimeout } from "ext:deno_web/02_timers.js";
 import { resourceForReadableStream } from "ext:deno_web/06_streams.js";
-import { TcpConn } from "ext:deno_net/01_net.js";
+import { UpgradedConn } from "ext:deno_net/01_net.js";
 import { STATUS_CODES } from "node:_http_server";
 import { methods as METHODS } from "node:_http_common";
+import { deprecate } from "node:util";
 
 const { internalRidSymbol } = core;
-const { ArrayIsArray } = primordials;
+const { ArrayIsArray, StringPrototypeToLowerCase } = primordials;
 
 type Chunk = string | Buffer | Uint8Array;
 
@@ -516,7 +518,7 @@ class ClientRequest extends OutgoingMessage {
           );
           assert(typeof res.remoteAddrIp !== "undefined");
           assert(typeof res.remoteAddrIp !== "undefined");
-          const conn = new TcpConn(
+          const conn = new UpgradedConn(
             upgradeRid,
             {
               transport: "tcp",
@@ -1183,49 +1185,95 @@ function onError(self, error, cb) {
   }
 }
 
-export class ServerResponse extends NodeWritable {
-  statusCode = 200;
-  statusMessage?: string = undefined;
-  #headers: Record<string, string | string[]> = { __proto__: null };
-  #hasNonStringHeaders: boolean = false;
-  #readable: ReadableStream;
-  override writable = true;
-  // used by `npm:on-finished`
-  finished = false;
-  headersSent = false;
-  #resolve: (value: Response | PromiseLike<Response>) => void;
+export type ServerResponse = {
+  statusCode: number;
+  statusMessage?: string;
+
+  _headers: Record<string, string | string[]>;
+  _hasNonStringHeaders: boolean;
+
+  _readable: ReadableStream;
+  finished: boolean;
+  headersSent: boolean;
+  _resolve: (value: Response | PromiseLike<Response>) => void;
   // deno-lint-ignore no-explicit-any
-  #socketOverride: any | null = null;
+  _socketOverride: any | null;
+  // deno-lint-ignore no-explicit-any
+  socket: any | null;
 
-  static #enqueue(controller: ReadableStreamDefaultController, chunk: Chunk) {
-    try {
-      if (typeof chunk === "string") {
-        controller.enqueue(ENCODER.encode(chunk));
-      } else {
-        controller.enqueue(chunk);
-      }
-    } catch (_) {
-      // The stream might have been closed. Ignore the error.
-    }
-  }
+  setHeader(name: string, value: string | string[]): void;
+  appendHeader(name: string, value: string | string[]): void;
+  getHeader(name: string): string | string[];
+  removeHeader(name: string): void;
+  getHeaderNames(): string[];
+  getHeaders(): Record<string, string | number | string[]>;
+  hasHeader(name: string): boolean;
 
-  /** Returns true if the response body should be null with the given
-   * http status code */
-  static #bodyShouldBeNull(status: number) {
-    return status === 101 || status === 204 || status === 205 || status === 304;
-  }
+  writeHead(
+    status: number,
+    statusMessage?: string,
+    headers?:
+      | Record<string, string | number | string[]>
+      | Array<[string, string]>,
+  ): void;
+  writeHead(
+    status: number,
+    headers?:
+      | Record<string, string | number | string[]>
+      | Array<[string, string]>,
+  ): void;
 
-  constructor(
+  _ensureHeaders(singleChunk?: Chunk): void;
+
+  respond(final: boolean, singleChunk?: Chunk): void;
+  // deno-lint-ignore no-explicit-any
+  end(chunk?: any, encoding?: any, cb?: any): void;
+
+  flushHeaders(): void;
+  _implicitHeader(): void;
+
+  // Undocumented field used by `npm:light-my-request`.
+  _header: string;
+
+  assignSocket(socket): void;
+  detachSocket(socket): void;
+} & { -readonly [K in keyof NodeWritable]: NodeWritable[K] };
+
+type ServerResponseStatic = {
+  new (
     resolve: (value: Response | PromiseLike<Response>) => void,
     socket: FakeSocket,
-  ) {
-    let controller: ReadableByteStreamController;
-    const readable = new ReadableStream({
-      start(c) {
-        controller = c as ReadableByteStreamController;
-      },
-    });
-    super({
+  ): ServerResponse;
+  _enqueue(controller: ReadableStreamDefaultController, chunk: Chunk): void;
+  _bodyShouldBeNull(statusCode: number): boolean;
+};
+
+export const ServerResponse = function (
+  this: ServerResponse,
+  resolve: (value: Response | PromiseLike<Response>) => void,
+  socket: FakeSocket,
+) {
+  this.statusCode = 200;
+  this.statusMessage = undefined;
+  this._headers = { __proto__: null };
+  this._hasNonStringHeaders = false;
+  this.writable = true;
+
+  // used by `npm:on-finished`
+  this.finished = false;
+  this.headersSent = false;
+  this._socketOverride = null;
+
+  let controller: ReadableByteStreamController;
+  const readable = new ReadableStream({
+    start(c) {
+      controller = c as ReadableByteStreamController;
+    },
+  });
+
+  NodeWritable.call(
+    this,
+    {
       autoDestroy: true,
       defaultEncoding: "utf-8",
       emitClose: true,
@@ -1234,16 +1282,16 @@ export class ServerResponse extends NodeWritable {
       write: (chunk, encoding, cb) => {
         // Writes chunks are directly written to the socket if
         // one is assigned via assignSocket()
-        if (this.#socketOverride && this.#socketOverride.writable) {
-          this.#socketOverride.write(chunk, encoding);
+        if (this._socketOverride && this._socketOverride.writable) {
+          this._socketOverride.write(chunk, encoding);
           return cb();
         }
         if (!this.headersSent) {
-          ServerResponse.#enqueue(controller, chunk);
+          ServerResponse._enqueue(controller, chunk);
           this.respond(false);
           return cb();
         }
-        ServerResponse.#enqueue(controller, chunk);
+        ServerResponse._enqueue(controller, chunk);
         return cb();
       },
       final: (cb) => {
@@ -1259,192 +1307,269 @@ export class ServerResponse extends NodeWritable {
         }
         return cb(null);
       },
-    });
-    this.#readable = readable;
-    this.#resolve = resolve;
-    this.socket = socket;
-  }
+    } satisfies NodeWritableOptions,
+  );
 
-  setHeader(name: string, value: string | string[]) {
-    if (Array.isArray(value)) {
-      this.#hasNonStringHeaders = true;
-    }
-    this.#headers[name] = value;
-    return this;
-  }
+  this._readable = readable;
+  this._resolve = resolve;
+  this.socket = socket;
 
-  appendHeader(name: string, value: string | string[]) {
-    if (this.#headers[name] === undefined) {
-      if (Array.isArray(value)) this.#hasNonStringHeaders = true;
-      this.#headers[name] = value;
+  this._header = "";
+} as unknown as ServerResponseStatic;
+
+Object.setPrototypeOf(ServerResponse.prototype, NodeWritable.prototype);
+Object.setPrototypeOf(ServerResponse, NodeWritable);
+
+ServerResponse._enqueue = function (
+  this: ServerResponse,
+  controller: ReadableStreamDefaultController,
+  chunk: Chunk,
+) {
+  try {
+    if (typeof chunk === "string") {
+      controller.enqueue(ENCODER.encode(chunk));
     } else {
-      this.#hasNonStringHeaders = true;
-      if (!Array.isArray(this.#headers[name])) {
-        this.#headers[name] = [this.#headers[name]];
+      controller.enqueue(chunk);
+    }
+  } catch (_) {
+    // The stream might have been closed. Ignore the error.
+  }
+};
+
+/** Returns true if the response body should be null with the given
+ * http status code */
+ServerResponse._bodyShouldBeNull = function (
+  this: ServerResponse,
+  status: number,
+) {
+  return status === 101 || status === 204 || status === 205 || status === 304;
+};
+
+ServerResponse.prototype.setHeader = function (
+  this: ServerResponse,
+  name: string,
+  value: string | string[],
+) {
+  if (Array.isArray(value)) {
+    this._hasNonStringHeaders = true;
+  }
+  this._headers[StringPrototypeToLowerCase(name)] = value;
+  return this;
+};
+
+ServerResponse.prototype.appendHeader = function (
+  this: ServerResponse,
+  name: string,
+  value: string | string[],
+) {
+  const key = StringPrototypeToLowerCase(name);
+  if (this._headers[key] === undefined) {
+    if (Array.isArray(value)) this._hasNonStringHeaders = true;
+    this._headers[key] = value;
+  } else {
+    this._hasNonStringHeaders = true;
+    if (!Array.isArray(this._headers[key])) {
+      this._headers[key] = [this._headers[key]];
+    }
+    const header = this._headers[key];
+    if (Array.isArray(value)) {
+      header.push(...value);
+    } else {
+      header.push(value);
+    }
+  }
+  return this;
+};
+
+ServerResponse.prototype.getHeader = function (
+  this: ServerResponse,
+  name: string,
+) {
+  return this._headers[StringPrototypeToLowerCase(name)];
+};
+
+ServerResponse.prototype.removeHeader = function (
+  this: ServerResponse,
+  name: string,
+) {
+  delete this._headers[StringPrototypeToLowerCase(name)];
+};
+
+ServerResponse.prototype.getHeaderNames = function (this: ServerResponse) {
+  return Object.keys(this._headers);
+};
+
+ServerResponse.prototype.getHeaders = function (
+  this: ServerResponse,
+): Record<string, string | number | string[]> {
+  return { __proto__: null, ...this._headers };
+};
+
+ServerResponse.prototype.hasHeader = function (
+  this: ServerResponse,
+  name: string,
+) {
+  return Object.hasOwn(this._headers, name);
+};
+
+ServerResponse.prototype.writeHead = function (
+  this: ServerResponse,
+  status: number,
+  statusMessageOrHeaders?:
+    | string
+    | Record<string, string | number | string[]>
+    | Array<[string, string]>,
+  maybeHeaders?:
+    | Record<string, string | number | string[]>
+    | Array<[string, string]>,
+) {
+  this.statusCode = status;
+
+  let headers = null;
+  if (typeof statusMessageOrHeaders === "string") {
+    this.statusMessage = statusMessageOrHeaders;
+    if (maybeHeaders !== undefined) {
+      headers = maybeHeaders;
+    }
+  } else if (statusMessageOrHeaders !== undefined) {
+    headers = statusMessageOrHeaders;
+  }
+
+  if (headers !== null) {
+    if (ArrayIsArray(headers)) {
+      headers = headers as Array<[string, string]>;
+      for (let i = 0; i < headers.length; i++) {
+        this.appendHeader(headers[i][0], headers[i][1]);
       }
-      const header = this.#headers[name];
-      if (Array.isArray(value)) {
-        header.push(...value);
-      } else {
-        header.push(value);
+    } else {
+      headers = headers as Record<string, string>;
+      for (const k in headers) {
+        if (Object.hasOwn(headers, k)) {
+          this.setHeader(k, headers[k]);
+        }
       }
     }
-    return this;
   }
 
-  getHeader(name: string) {
-    return this.#headers[name];
-  }
-  removeHeader(name: string) {
-    delete this.#headers[name];
-  }
-  getHeaderNames() {
-    return Object.keys(this.#headers);
-  }
-  getHeaders(): Record<string, string | number | string[]> {
-    // @ts-ignore Ignore null __proto__
-    return { __proto__: null, ...this.#headers };
-  }
-  hasHeader(name: string) {
-    return Object.hasOwn(this.#headers, name);
-  }
+  return this;
+};
 
-  writeHead(
-    status: number,
-    statusMessage?: string,
-    headers?:
-      | Record<string, string | number | string[]>
-      | Array<[string, string]>,
-  ): this;
-  writeHead(
-    status: number,
-    headers?:
-      | Record<string, string | number | string[]>
-      | Array<[string, string]>,
-  ): this;
-  writeHead(
-    status: number,
-    statusMessageOrHeaders?:
-      | string
-      | Record<string, string | number | string[]>
-      | Array<[string, string]>,
-    maybeHeaders?:
-      | Record<string, string | number | string[]>
-      | Array<[string, string]>,
-  ): this {
-    this.statusCode = status;
+ServerResponse.prototype._ensureHeaders = function (
+  this: ServerResponse,
+  singleChunk?: Chunk,
+) {
+  if (this.statusCode === 200 && this.statusMessage === undefined) {
+    this.statusMessage = "OK";
+  }
+  if (typeof singleChunk === "string" && !this.hasHeader("content-type")) {
+    this.setHeader("content-type", "text/plain;charset=UTF-8");
+  }
+};
 
-    let headers = null;
-    if (typeof statusMessageOrHeaders === "string") {
-      this.statusMessage = statusMessageOrHeaders;
-      if (maybeHeaders !== undefined) {
-        headers = maybeHeaders;
-      }
-    } else if (statusMessageOrHeaders !== undefined) {
-      headers = statusMessageOrHeaders;
-    }
-
-    if (headers !== null) {
-      if (ArrayIsArray(headers)) {
-        headers = headers as Array<[string, string]>;
-        for (let i = 0; i < headers.length; i++) {
-          this.appendHeader(headers[i][0], headers[i][1]);
+ServerResponse.prototype.respond = function (
+  this: ServerResponse,
+  final: boolean,
+  singleChunk?: Chunk,
+) {
+  this.headersSent = true;
+  this._ensureHeaders(singleChunk);
+  let body = singleChunk ?? (final ? null : this._readable);
+  if (ServerResponse._bodyShouldBeNull(this.statusCode)) {
+    body = null;
+  }
+  let headers: Record<string, string> | [string, string][] = this
+    ._headers as Record<string, string>;
+  if (this._hasNonStringHeaders) {
+    headers = [];
+    // Guard is not needed as this is a null prototype object.
+    // deno-lint-ignore guard-for-in
+    for (const key in this._headers) {
+      const entry = this._headers[key];
+      if (Array.isArray(entry)) {
+        for (const value of entry) {
+          headers.push([key, value]);
         }
       } else {
-        headers = headers as Record<string, string>;
-        for (const k in headers) {
-          if (Object.hasOwn(headers, k)) {
-            this.setHeader(k, headers[k]);
-          }
-        }
+        headers.push([key, entry]);
       }
     }
-
-    return this;
-  }
-
-  #ensureHeaders(singleChunk?: Chunk) {
-    if (this.statusCode === 200 && this.statusMessage === undefined) {
-      this.statusMessage = "OK";
-    }
-    if (
-      typeof singleChunk === "string" &&
-      !this.hasHeader("content-type")
-    ) {
-      this.setHeader("content-type", "text/plain;charset=UTF-8");
-    }
-  }
-
-  respond(final: boolean, singleChunk?: Chunk) {
-    this.headersSent = true;
-    this.#ensureHeaders(singleChunk);
-    let body = singleChunk ?? (final ? null : this.#readable);
-    if (ServerResponse.#bodyShouldBeNull(this.statusCode)) {
-      body = null;
-    }
-    let headers: Record<string, string> | [string, string][] = this
-      .#headers as Record<string, string>;
-    if (this.#hasNonStringHeaders) {
-      headers = [];
-      // Guard is not needed as this is a null prototype object.
-      // deno-lint-ignore guard-for-in
-      for (const key in this.#headers) {
-        const entry = this.#headers[key];
-        if (Array.isArray(entry)) {
-          for (const value of entry) {
-            headers.push([key, value]);
-          }
-        } else {
-          headers.push([key, entry]);
-        }
-      }
-    }
-    this.#resolve(
-      new Response(body, {
-        headers,
-        status: this.statusCode,
-        statusText: this.statusMessage,
-      }),
-    );
   }
+  this._resolve(
+    new Response(body, {
+      headers,
+      status: this.statusCode,
+      statusText: this.statusMessage,
+    }),
+  );
+};
 
+ServerResponse.prototype.end = function (
+  this: ServerResponse,
   // deno-lint-ignore no-explicit-any
-  override end(chunk?: any, encoding?: any, cb?: any): this {
-    this.finished = true;
-    if (!chunk && "transfer-encoding" in this.#headers) {
-      // FIXME(bnoordhuis) Node sends a zero length chunked body instead, i.e.,
-      // the trailing "0\r\n", but respondWith() just hangs when I try that.
-      this.#headers["content-length"] = "0";
-      delete this.#headers["transfer-encoding"];
-    }
-
-    // @ts-expect-error The signature for cb is stricter than the one implemented here
-    return super.end(chunk, encoding, cb);
+  chunk?: any,
+  // deno-lint-ignore no-explicit-any
+  encoding?: any,
+  // deno-lint-ignore no-explicit-any
+  cb?: any,
+) {
+  this.finished = true;
+  if (!chunk && "transfer-encoding" in this._headers) {
+    // FIXME(bnoordhuis) Node sends a zero length chunked body instead, i.e.,
+    // the trailing "0\r\n", but respondWith() just hangs when I try that.
+    this._headers["content-length"] = "0";
+    delete this._headers["transfer-encoding"];
   }
 
-  flushHeaders() {
-    // no-op
-  }
+  // @ts-expect-error The signature for cb is stricter than the one implemented here
+  NodeWritable.prototype.end.call(this, chunk, encoding, cb);
+};
 
-  // Undocumented API used by `npm:compression`.
-  _implicitHeader() {
-    this.writeHead(this.statusCode);
-  }
+ServerResponse.prototype.flushHeaders = function (this: ServerResponse) {
+  // no-op
+};
 
-  assignSocket(socket) {
-    if (socket._httpMessage) {
-      throw new ERR_HTTP_SOCKET_ASSIGNED();
-    }
-    socket._httpMessage = this;
-    this.#socketOverride = socket;
-  }
+// Undocumented API used by `npm:compression`.
+ServerResponse.prototype._implicitHeader = function (this: ServerResponse) {
+  this.writeHead(this.statusCode);
+};
 
-  detachSocket(socket) {
-    assert(socket._httpMessage === this);
-    socket._httpMessage = null;
-    this.#socketOverride = null;
+ServerResponse.prototype.assignSocket = function (
+  this: ServerResponse,
+  socket,
+) {
+  if (socket._httpMessage) {
+    throw new ERR_HTTP_SOCKET_ASSIGNED();
   }
-}
+  socket._httpMessage = this;
+  this._socketOverride = socket;
+};
+
+ServerResponse.prototype.detachSocket = function (
+  this: ServerResponse,
+  socket,
+) {
+  assert(socket._httpMessage === this);
+  socket._httpMessage = null;
+  this._socketOverride = null;
+};
+
+Object.defineProperty(ServerResponse.prototype, "connection", {
+  get: deprecate(
+    function (this: ServerResponse) {
+      return this._socketOverride;
+    },
+    "ServerResponse.prototype.connection is deprecated",
+    "DEP0066",
+  ),
+  set: deprecate(
+    // deno-lint-ignore no-explicit-any
+    function (this: ServerResponse, socket: any) {
+      this._socketOverride = socket;
+    },
+    "ServerResponse.prototype.connection is deprecated",
+    "DEP0066",
+  ),
+});
 
 // TODO(@AaronO): optimize
 export class IncomingMessageForServer extends NodeReadable {
@@ -1677,6 +1802,8 @@ export class ServerImpl extends EventEmitter {
       this.#server.ref();
     }
     this.#unref = false;
+
+    return this;
   }
 
   unref() {
@@ -1684,6 +1811,8 @@ export class ServerImpl extends EventEmitter {
       this.#server.unref();
     }
     this.#unref = true;
+
+    return this;
   }
 
   close(cb?: (err?: Error) => void): this {
diff --git a/ext/node/polyfills/http2.ts b/ext/node/polyfills/http2.ts
index a9ced2bd9e..dc2379aebb 100644
--- a/ext/node/polyfills/http2.ts
+++ b/ext/node/polyfills/http2.ts
@@ -882,6 +882,7 @@ export class ClientHttp2Stream extends Duplex {
       trailersReady: false,
       endAfterHeaders: false,
       shutdownWritableCalled: false,
+      serverEndedCall: false,
     };
     this[kDenoResponse] = undefined;
     this[kDenoRid] = undefined;
@@ -1109,7 +1110,9 @@ export class ClientHttp2Stream extends Duplex {
       }
 
       debugHttp2(">>> chunk", chunk, finished, this[kDenoResponse].bodyRid);
-      if (chunk === null) {
+      if (finished || chunk === null) {
+        this[kState].serverEndedCall = true;
+
         const trailerList = await op_http2_client_get_response_trailers(
           this[kDenoResponse].bodyRid,
         );
@@ -1237,7 +1240,9 @@ export class ClientHttp2Stream extends Duplex {
     this[kSession] = undefined;
 
     session[kMaybeDestroy]();
-    callback(err);
+    if (callback) {
+      callback(err);
+    }
   }
 
   [kMaybeDestroy](code = constants.NGHTTP2_NO_ERROR) {
@@ -1280,6 +1285,9 @@ function shutdownWritable(stream, callback, streamRid) {
   if (state.flags & STREAM_FLAGS_HAS_TRAILERS) {
     onStreamTrailers(stream);
     callback();
+  } else if (state.serverEndedCall) {
+    debugHttp2(">>> stream finished");
+    callback();
   } else {
     op_http2_client_send_data(streamRid, new Uint8Array(), true)
       .then(() => {
diff --git a/ext/node/polyfills/inspector.js b/ext/node/polyfills/inspector.js
new file mode 100644
index 0000000000..7eb15ce917
--- /dev/null
+++ b/ext/node/polyfills/inspector.js
@@ -0,0 +1,210 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+// Copyright Joyent and Node contributors. All rights reserved. MIT license.
+
+import process from "node:process";
+import { EventEmitter } from "node:events";
+import { primordials } from "ext:core/mod.js";
+import {
+  op_get_extras_binding_object,
+  op_inspector_close,
+  op_inspector_connect,
+  op_inspector_disconnect,
+  op_inspector_dispatch,
+  op_inspector_emit_protocol_event,
+  op_inspector_enabled,
+  op_inspector_open,
+  op_inspector_url,
+  op_inspector_wait,
+} from "ext:core/ops";
+import {
+  isUint32,
+  validateFunction,
+  validateInt32,
+  validateObject,
+  validateString,
+} from "ext:deno_node/internal/validators.mjs";
+import {
+  ERR_INSPECTOR_ALREADY_ACTIVATED,
+  ERR_INSPECTOR_ALREADY_CONNECTED,
+  ERR_INSPECTOR_CLOSED,
+  ERR_INSPECTOR_COMMAND,
+  ERR_INSPECTOR_NOT_ACTIVE,
+  ERR_INSPECTOR_NOT_CONNECTED,
+  ERR_INSPECTOR_NOT_WORKER,
+} from "ext:deno_node/internal/errors.ts";
+
+const {
+  SymbolDispose,
+  JSONParse,
+  JSONStringify,
+  SafeMap,
+} = primordials;
+
+class Session extends EventEmitter {
+  #connection = null;
+  #nextId = 1;
+  #messageCallbacks = new SafeMap();
+
+  connect() {
+    if (this.#connection) {
+      throw new ERR_INSPECTOR_ALREADY_CONNECTED("The inspector session");
+    }
+    this.#connection = op_inspector_connect(false, (m) => this.#onMessage(m));
+  }
+
+  connectToMainThread() {
+    if (isMainThread) {
+      throw new ERR_INSPECTOR_NOT_WORKER();
+    }
+    if (this.#connection) {
+      throw new ERR_INSPECTOR_ALREADY_CONNECTED("The inspector session");
+    }
+    this.#connection = op_inspector_connect(true, (m) => this.#onMessage(m));
+  }
+
+  #onMessage(message) {
+    const parsed = JSONParse(message);
+    try {
+      if (parsed.id) {
+        const callback = this.#messageCallbacks.get(parsed.id);
+        this.#messageCallbacks.delete(parsed.id);
+        if (callback) {
+          if (parsed.error) {
+            return callback(
+              new ERR_INSPECTOR_COMMAND(
+                parsed.error.code,
+                parsed.error.message,
+              ),
+            );
+          }
+
+          callback(null, parsed.result);
+        }
+      } else {
+        this.emit(parsed.method, parsed);
+        this.emit("inspectorNotification", parsed);
+      }
+    } catch (error) {
+      process.emitWarning(error);
+    }
+  }
+
+  post(method, params, callback) {
+    validateString(method, "method");
+    if (!callback && typeof params === "function") {
+      callback = params;
+      params = null;
+    }
+    if (params) {
+      validateObject(params, "params");
+    }
+    if (callback) {
+      validateFunction(callback, "callback");
+    }
+
+    if (!this.#connection) {
+      throw new ERR_INSPECTOR_NOT_CONNECTED();
+    }
+    const id = this.#nextId++;
+    const message = { id, method };
+    if (params) {
+      message.params = params;
+    }
+    if (callback) {
+      this.#messageCallbacks.set(id, callback);
+    }
+    op_inspector_dispatch(this.#connection, JSONStringify(message));
+  }
+
+  disconnect() {
+    if (!this.#connection) {
+      return;
+    }
+    op_inspector_disconnect(this.#connection);
+    this.#connection = null;
+    // deno-lint-ignore prefer-primordials
+    for (const callback of this.#messageCallbacks.values()) {
+      process.nextTick(callback, new ERR_INSPECTOR_CLOSED());
+    }
+    this.#messageCallbacks.clear();
+    this.#nextId = 1;
+  }
+}
+
+function open(port, host, wait) {
+  if (op_inspector_enabled()) {
+    throw new ERR_INSPECTOR_ALREADY_ACTIVATED();
+  }
+  // inspectorOpen() currently does not typecheck its arguments and adding
+  // such checks would be a potentially breaking change. However, the native
+  // open() function requires the port to fit into a 16-bit unsigned integer,
+  // causing an integer overflow otherwise, so we at least need to prevent that.
+  if (isUint32(port)) {
+    validateInt32(port, "port", 0, 65535);
+  } else {
+    // equiv of handling args[0]->IsUint32()
+    port = undefined;
+  }
+  if (typeof host !== "string") {
+    // equiv of handling args[1]->IsString()
+    host = undefined;
+  }
+  op_inspector_open(port, host);
+  if (wait) {
+    op_inspector_wait();
+  }
+
+  return {
+    __proto__: null,
+    [SymbolDispose]() {
+      _debugEnd();
+    },
+  };
+}
+
+function close() {
+  op_inspector_close();
+}
+
+function url() {
+  return op_inspector_url();
+}
+
+function waitForDebugger() {
+  if (!op_inspector_wait()) {
+    throw new ERR_INSPECTOR_NOT_ACTIVE();
+  }
+}
+
+function broadcastToFrontend(eventName, params) {
+  validateString(eventName, "eventName");
+  if (params) {
+    validateObject(params, "params");
+  }
+  op_inspector_emit_protocol_event(eventName, JSONStringify(params ?? {}));
+}
+
+const Network = {
+  requestWillBeSent: (params) =>
+    broadcastToFrontend("Network.requestWillBeSent", params),
+  responseReceived: (params) =>
+    broadcastToFrontend("Network.responseReceived", params),
+  loadingFinished: (params) =>
+    broadcastToFrontend("Network.loadingFinished", params),
+  loadingFailed: (params) =>
+    broadcastToFrontend("Network.loadingFailed", params),
+};
+
+const console = op_get_extras_binding_object().console;
+
+export { close, console, Network, open, Session, url, waitForDebugger };
+
+export default {
+  open,
+  close,
+  url,
+  waitForDebugger,
+  console,
+  Session,
+  Network,
+};
diff --git a/ext/node/polyfills/inspector.ts b/ext/node/polyfills/inspector.ts
deleted file mode 100644
index 9de86ab14f..0000000000
--- a/ext/node/polyfills/inspector.ts
+++ /dev/null
@@ -1,82 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-// Copyright Joyent and Node contributors. All rights reserved. MIT license.
-
-import { EventEmitter } from "node:events";
-import { notImplemented } from "ext:deno_node/_utils.ts";
-import { primordials } from "ext:core/mod.js";
-
-const {
-  SafeMap,
-} = primordials;
-
-class Session extends EventEmitter {
-  #connection = null;
-  #nextId = 1;
-  #messageCallbacks = new SafeMap();
-
-  /** Connects the session to the inspector back-end. */
-  connect() {
-    notImplemented("inspector.Session.prototype.connect");
-  }
-
-  /** Connects the session to the main thread
-   * inspector back-end. */
-  connectToMainThread() {
-    notImplemented("inspector.Session.prototype.connectToMainThread");
-  }
-
-  /** Posts a message to the inspector back-end. */
-  post(
-    _method: string,
-    _params?: Record<string, unknown>,
-    _callback?: (...args: unknown[]) => void,
-  ) {
-    notImplemented("inspector.Session.prototype.post");
-  }
-
-  /** Immediately closes the session, all pending
-   * message callbacks will be called with an
-   * error.
-   */
-  disconnect() {
-    notImplemented("inspector.Session.prototype.disconnect");
-  }
-}
-
-/** Activates inspector on host and port.
- * See https://nodejs.org/api/inspector.html#inspectoropenport-host-wait */
-function open(_port?: number, _host?: string, _wait?: boolean) {
-  notImplemented("inspector.Session.prototype.open");
-}
-
-/** Deactivate the inspector. Blocks until there are no active connections.
- * See https://nodejs.org/api/inspector.html#inspectorclose */
-function close() {
-  notImplemented("inspector.Session.prototype.close");
-}
-
-/** Return the URL of the active inspector, or undefined if there is none.
- * See https://nodejs.org/api/inspector.html#inspectorurl */
-function url() {
-  // TODO(kt3k): returns undefined for now, which means the inspector is not activated.
-  return undefined;
-}
-
-/** Blocks until a client (existing or connected later) has sent Runtime.runIfWaitingForDebugger command.
- * See https://nodejs.org/api/inspector.html#inspectorwaitfordebugger */
-function waitForDebugger() {
-  notImplemented("inspector.wairForDebugger");
-}
-
-const console = globalThis.console;
-
-export { close, console, open, Session, url, waitForDebugger };
-
-export default {
-  close,
-  console,
-  open,
-  Session,
-  url,
-  waitForDebugger,
-};
diff --git a/ext/node/polyfills/inspector/promises.js b/ext/node/polyfills/inspector/promises.js
new file mode 100644
index 0000000000..3483e53f5e
--- /dev/null
+++ b/ext/node/polyfills/inspector/promises.js
@@ -0,0 +1,20 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+// Copyright Joyent and Node contributors. All rights reserved. MIT license.
+
+import inspector from "node:inspector";
+import { promisify } from "ext:deno_node/internal/util.mjs";
+
+class Session extends inspector.Session {
+  constructor() {
+    super();
+  }
+}
+Session.prototype.post = promisify(inspector.Session.prototype.post);
+
+export * from "node:inspector";
+export { Session };
+
+export default {
+  ...inspector,
+  Session,
+};
diff --git a/ext/node/polyfills/internal/buffer.mjs b/ext/node/polyfills/internal/buffer.mjs
index 6e43a49031..dd549221fa 100644
--- a/ext/node/polyfills/internal/buffer.mjs
+++ b/ext/node/polyfills/internal/buffer.mjs
@@ -2,11 +2,60 @@
 // Copyright Joyent and Node contributors. All rights reserved. MIT license.
 // Copyright Feross Aboukhadijeh, and other contributors. All rights reserved. MIT license.
 
-// TODO(petamoriken): enable prefer-primordials for node polyfills
-// deno-lint-ignore-file prefer-primordials
-
-import { core } from "ext:core/mod.js";
-import { op_is_ascii, op_is_utf8 } from "ext:core/ops";
+import { core, primordials } from "ext:core/mod.js";
+const {
+  isAnyArrayBuffer,
+  isArrayBuffer,
+  isDataView,
+  isSharedArrayBuffer,
+  isTypedArray,
+} = core;
+const {
+  ArrayBufferPrototypeGetByteLength,
+  ArrayBufferPrototypeGetDetached,
+  ArrayIsArray,
+  ArrayPrototypeSlice,
+  BigInt,
+  DataViewPrototypeGetByteLength,
+  Float32Array,
+  Float64Array,
+  MathFloor,
+  MathMin,
+  Number,
+  NumberIsInteger,
+  NumberIsNaN,
+  NumberMAX_SAFE_INTEGER,
+  NumberMIN_SAFE_INTEGER,
+  NumberPrototypeToString,
+  ObjectCreate,
+  ObjectDefineProperty,
+  ObjectPrototypeIsPrototypeOf,
+  ObjectSetPrototypeOf,
+  RangeError,
+  SafeRegExp,
+  String,
+  StringFromCharCode,
+  StringPrototypeCharCodeAt,
+  StringPrototypeIncludes,
+  StringPrototypeReplace,
+  StringPrototypeToLowerCase,
+  StringPrototypeTrim,
+  SymbolFor,
+  SymbolToPrimitive,
+  TypeError,
+  TypeErrorPrototype,
+  TypedArrayPrototypeCopyWithin,
+  TypedArrayPrototypeFill,
+  TypedArrayPrototypeGetBuffer,
+  TypedArrayPrototypeGetByteLength,
+  TypedArrayPrototypeGetByteOffset,
+  TypedArrayPrototypeSet,
+  TypedArrayPrototypeSlice,
+  TypedArrayPrototypeSubarray,
+  Uint8Array,
+  Uint8ArrayPrototype,
+} = primordials;
+import { op_is_ascii, op_is_utf8, op_transcode } from "ext:core/ops";
 
 import { TextDecoder, TextEncoder } from "ext:deno_web/08_text_encoding.js";
 import { codes } from "ext:deno_node/internal/error_codes.ts";
@@ -24,15 +73,14 @@ import {
   hexToBytes,
   utf16leToBytes,
 } from "ext:deno_node/internal_binding/_utils.ts";
-import {
-  isAnyArrayBuffer,
-  isArrayBufferView,
-  isTypedArray,
-} from "ext:deno_node/internal/util/types.ts";
 import { normalizeEncoding } from "ext:deno_node/internal/util.mjs";
 import { validateBuffer } from "ext:deno_node/internal/validators.mjs";
 import { isUint8Array } from "ext:deno_node/internal/util/types.ts";
-import { ERR_INVALID_STATE, NodeError } from "ext:deno_node/internal/errors.ts";
+import {
+  ERR_INVALID_STATE,
+  genericNodeError,
+  NodeError,
+} from "ext:deno_node/internal/errors.ts";
 import {
   forgivingBase64Encode,
   forgivingBase64UrlEncode,
@@ -46,9 +94,13 @@ const utf8Encoder = new TextEncoder();
 
 // Temporary buffers to convert numbers.
 const float32Array = new Float32Array(1);
-const uInt8Float32Array = new Uint8Array(float32Array.buffer);
+const uInt8Float32Array = new Uint8Array(
+  TypedArrayPrototypeGetBuffer(float32Array),
+);
 const float64Array = new Float64Array(1);
-const uInt8Float64Array = new Uint8Array(float64Array.buffer);
+const uInt8Float64Array = new Uint8Array(
+  TypedArrayPrototypeGetBuffer(float64Array),
+);
 
 // Check endianness.
 float32Array[0] = -1; // 0xBF800000
@@ -60,10 +112,7 @@ export const kMaxLength = 2147483647;
 export const kStringMaxLength = 536870888;
 const MAX_UINT32 = 2 ** 32;
 
-const customInspectSymbol =
-  typeof Symbol === "function" && typeof Symbol["for"] === "function"
-    ? Symbol["for"]("nodejs.util.inspect.custom")
-    : null;
+const customInspectSymbol = SymbolFor("nodejs.util.inspect.custom");
 
 export const INSPECT_MAX_BYTES = 50;
 
@@ -72,23 +121,25 @@ export const constants = {
   MAX_STRING_LENGTH: kStringMaxLength,
 };
 
-Object.defineProperty(Buffer.prototype, "parent", {
+ObjectDefineProperty(Buffer.prototype, "parent", {
+  __proto__: null,
   enumerable: true,
   get: function () {
-    if (!Buffer.isBuffer(this)) {
+    if (!BufferIsBuffer(this)) {
       return void 0;
     }
-    return this.buffer;
+    return TypedArrayPrototypeGetBuffer(this);
   },
 });
 
-Object.defineProperty(Buffer.prototype, "offset", {
+ObjectDefineProperty(Buffer.prototype, "offset", {
+  __proto__: null,
   enumerable: true,
   get: function () {
-    if (!Buffer.isBuffer(this)) {
+    if (!BufferIsBuffer(this)) {
       return void 0;
     }
-    return this.byteOffset;
+    return TypedArrayPrototypeGetByteOffset(this);
   },
 });
 
@@ -99,10 +150,21 @@ function createBuffer(length) {
     );
   }
   const buf = new Uint8Array(length);
-  Object.setPrototypeOf(buf, Buffer.prototype);
+  ObjectSetPrototypeOf(buf, BufferPrototype);
   return buf;
 }
 
+/**
+ * @param {ArrayBufferLike} O
+ * @returns {boolean}
+ */
+function isDetachedBuffer(O) {
+  if (isSharedArrayBuffer(O)) {
+    return false;
+  }
+  return ArrayBufferPrototypeGetDetached(O);
+}
+
 export function Buffer(arg, encodingOrOffset, length) {
   if (typeof arg === "number") {
     if (typeof encodingOrOffset === "string") {
@@ -129,6 +191,7 @@ function _from(value, encodingOrOffset, length) {
       return fromArrayBuffer(value, encodingOrOffset, length);
     }
 
+    // deno-lint-ignore prefer-primordials
     const valueOf = value.valueOf && value.valueOf();
     if (
       valueOf != null &&
@@ -143,8 +206,8 @@ function _from(value, encodingOrOffset, length) {
       return b;
     }
 
-    if (typeof value[Symbol.toPrimitive] === "function") {
-      const primitive = value[Symbol.toPrimitive]("string");
+    if (typeof value[SymbolToPrimitive] === "function") {
+      const primitive = value[SymbolToPrimitive]("string");
       if (typeof primitive === "string") {
         return fromString(primitive, encodingOrOffset);
       }
@@ -158,13 +221,19 @@ function _from(value, encodingOrOffset, length) {
   );
 }
 
-Buffer.from = function from(value, encodingOrOffset, length) {
+const BufferFrom = Buffer.from = function from(
+  value,
+  encodingOrOffset,
+  length,
+) {
   return _from(value, encodingOrOffset, length);
 };
 
-Object.setPrototypeOf(Buffer.prototype, Uint8Array.prototype);
+const BufferPrototype = Buffer.prototype;
 
-Object.setPrototypeOf(Buffer, Uint8Array);
+ObjectSetPrototypeOf(Buffer.prototype, Uint8ArrayPrototype);
+
+ObjectSetPrototypeOf(Buffer, Uint8Array);
 
 function assertSize(size) {
   validateNumber(size, "size", 0, kMaxLength);
@@ -182,6 +251,7 @@ function _alloc(size, fill, encoding) {
         encoding,
       );
     }
+    // deno-lint-ignore prefer-primordials
     return buffer.fill(fill, encoding);
   }
   return buffer;
@@ -208,13 +278,14 @@ function fromString(string, encoding) {
   if (typeof encoding !== "string" || encoding === "") {
     encoding = "utf8";
   }
-  if (!Buffer.isEncoding(encoding)) {
+  if (!BufferIsEncoding(encoding)) {
     throw new codes.ERR_UNKNOWN_ENCODING(encoding);
   }
   const length = byteLength(string, encoding) | 0;
   let buf = createBuffer(length);
   const actual = buf.write(string, encoding);
   if (actual !== length) {
+    // deno-lint-ignore prefer-primordials
     buf = buf.slice(0, actual);
   }
   return buf;
@@ -222,11 +293,12 @@ function fromString(string, encoding) {
 
 function fromArrayLike(obj) {
   const buf = new Uint8Array(obj);
-  Object.setPrototypeOf(buf, Buffer.prototype);
+  ObjectSetPrototypeOf(buf, BufferPrototype);
   return buf;
 }
 
 function fromObject(obj) {
+  // deno-lint-ignore prefer-primordials
   if (obj.length !== undefined || isAnyArrayBuffer(obj.buffer)) {
     if (typeof obj.length !== "number") {
       return createBuffer(0);
@@ -235,7 +307,7 @@ function fromObject(obj) {
     return fromArrayLike(obj);
   }
 
-  if (obj.type === "Buffer" && Array.isArray(obj.data)) {
+  if (obj.type === "Buffer" && ArrayIsArray(obj.data)) {
     return fromArrayLike(obj.data);
   }
 }
@@ -244,7 +316,7 @@ function checked(length) {
   if (length >= kMaxLength) {
     throw new RangeError(
       "Attempt to allocate Buffer larger than maximum size: 0x" +
-        kMaxLength.toString(16) + " bytes",
+        NumberPrototypeToString(kMaxLength, 16) + " bytes",
     );
   }
   return length | 0;
@@ -252,25 +324,33 @@ function checked(length) {
 
 export function SlowBuffer(length) {
   assertSize(length);
-  return Buffer.alloc(+length);
+  return _alloc(+length);
 }
 
-Object.setPrototypeOf(SlowBuffer.prototype, Uint8Array.prototype);
+ObjectSetPrototypeOf(SlowBuffer.prototype, Uint8ArrayPrototype);
 
-Object.setPrototypeOf(SlowBuffer, Uint8Array);
+ObjectSetPrototypeOf(SlowBuffer, Uint8Array);
 
-Buffer.isBuffer = function isBuffer(b) {
-  return b != null && b._isBuffer === true && b !== Buffer.prototype;
+const BufferIsBuffer = Buffer.isBuffer = function isBuffer(b) {
+  return b != null && b._isBuffer === true && b !== BufferPrototype;
 };
 
-Buffer.compare = function compare(a, b) {
-  if (isInstance(a, Uint8Array)) {
-    a = Buffer.from(a, a.offset, a.byteLength);
+const BufferCompare = Buffer.compare = function compare(a, b) {
+  if (isUint8Array(a)) {
+    a = BufferFrom(
+      a,
+      TypedArrayPrototypeGetByteOffset(a),
+      TypedArrayPrototypeGetByteLength(a),
+    );
   }
-  if (isInstance(b, Uint8Array)) {
-    b = Buffer.from(b, b.offset, b.byteLength);
+  if (isUint8Array(b)) {
+    b = BufferFrom(
+      b,
+      TypedArrayPrototypeGetByteOffset(b),
+      TypedArrayPrototypeGetByteLength(b),
+    );
   }
-  if (!Buffer.isBuffer(a) || !Buffer.isBuffer(b)) {
+  if (!BufferIsBuffer(a) || !BufferIsBuffer(b)) {
     throw new TypeError(
       'The "buf1", "buf2" arguments must be one of type Buffer or Uint8Array',
     );
@@ -280,7 +360,7 @@ Buffer.compare = function compare(a, b) {
   }
   let x = a.length;
   let y = b.length;
-  for (let i = 0, len = Math.min(x, y); i < len; ++i) {
+  for (let i = 0, len = MathMin(x, y); i < len; ++i) {
     if (a[i] !== b[i]) {
       x = a[i];
       y = b[i];
@@ -296,18 +376,18 @@ Buffer.compare = function compare(a, b) {
   return 0;
 };
 
-Buffer.isEncoding = function isEncoding(encoding) {
+const BufferIsEncoding = Buffer.isEncoding = function isEncoding(encoding) {
   return typeof encoding === "string" && encoding.length !== 0 &&
     normalizeEncoding(encoding) !== undefined;
 };
 
 Buffer.concat = function concat(list, length) {
-  if (!Array.isArray(list)) {
+  if (!ArrayIsArray(list)) {
     throw new codes.ERR_INVALID_ARG_TYPE("list", "Array", list);
   }
 
   if (list.length === 0) {
-    return Buffer.alloc(0);
+    return _alloc(0);
   }
 
   if (length === undefined) {
@@ -321,7 +401,7 @@ Buffer.concat = function concat(list, length) {
     validateOffset(length, "length");
   }
 
-  const buffer = Buffer.allocUnsafe(length);
+  const buffer = _allocUnsafe(length);
   let pos = 0;
   for (let i = 0; i < list.length; i++) {
     const buf = list[i];
@@ -342,7 +422,7 @@ Buffer.concat = function concat(list, length) {
     // Zero-fill the remaining bytes if the specified `length` was more than
     // the actual total length, i.e. if we have some remaining allocated bytes
     // there were not initialized.
-    buffer.fill(0, pos, length);
+    TypedArrayPrototypeFill(buffer, 0, pos, length);
   }
 
   return buffer;
@@ -350,7 +430,18 @@ Buffer.concat = function concat(list, length) {
 
 function byteLength(string, encoding) {
   if (typeof string !== "string") {
-    if (isArrayBufferView(string) || isAnyArrayBuffer(string)) {
+    if (isTypedArray(string)) {
+      return TypedArrayPrototypeGetByteLength(string);
+    }
+    if (isDataView(string)) {
+      return DataViewPrototypeGetByteLength(string);
+    }
+    if (isArrayBuffer(string)) {
+      return ArrayBufferPrototypeGetByteLength(string);
+    }
+    if (isSharedArrayBuffer(string)) {
+      // TODO(petamoriken): add SharedArayBuffer to primordials
+      // deno-lint-ignore prefer-primordials
       return string.byteLength;
     }
 
@@ -459,6 +550,7 @@ Buffer.prototype.toString = function toString(encoding, start, end) {
     throw new codes.ERR_UNKNOWN_ENCODING(encoding);
   }
 
+  // deno-lint-ignore prefer-primordials
   return ops.slice(this, start, end);
 };
 
@@ -475,22 +567,29 @@ Buffer.prototype.equals = function equals(b) {
   if (this === b) {
     return true;
   }
-  return Buffer.compare(this, b) === 0;
+  return BufferCompare(this, b) === 0;
 };
 
-Buffer.prototype.inspect = function inspect() {
-  let str = "";
-  const max = INSPECT_MAX_BYTES;
-  str = this.toString("hex", 0, max).replace(/(.{2})/g, "$1 ").trim();
-  if (this.length > max) {
-    str += " ... ";
-  }
-  return "<Buffer " + str + ">";
-};
+const SPACER_PATTERN = new SafeRegExp(/(.{2})/g);
 
-if (customInspectSymbol) {
-  Buffer.prototype[customInspectSymbol] = Buffer.prototype.inspect;
-}
+Buffer.prototype[customInspectSymbol] =
+  Buffer.prototype.inspect =
+    function inspect() {
+      let str = "";
+      const max = INSPECT_MAX_BYTES;
+      str = StringPrototypeTrim(
+        StringPrototypeReplace(
+          // deno-lint-ignore prefer-primordials
+          this.toString("hex", 0, max),
+          SPACER_PATTERN,
+          "$1 ",
+        ),
+      );
+      if (this.length > max) {
+        str += " ... ";
+      }
+      return "<Buffer " + str + ">";
+    };
 
 Buffer.prototype.compare = function compare(
   target,
@@ -499,10 +598,14 @@ Buffer.prototype.compare = function compare(
   thisStart,
   thisEnd,
 ) {
-  if (isInstance(target, Uint8Array)) {
-    target = Buffer.from(target, target.offset, target.byteLength);
+  if (isUint8Array(target)) {
+    target = BufferFrom(
+      target,
+      TypedArrayPrototypeGetByteOffset(target),
+      TypedArrayPrototypeGetByteLength(target),
+    );
   }
-  if (!Buffer.isBuffer(target)) {
+  if (!BufferIsBuffer(target)) {
     throw new codes.ERR_INVALID_ARG_TYPE(
       "target",
       ["Buffer", "Uint8Array"],
@@ -559,8 +662,9 @@ Buffer.prototype.compare = function compare(
   }
   let x = thisEnd - thisStart;
   let y = end - start;
-  const len = Math.min(x, y);
-  const thisCopy = this.slice(thisStart, thisEnd);
+  const len = MathMin(x, y);
+  const thisCopy = TypedArrayPrototypeSlice(this, thisStart, thisEnd);
+  // deno-lint-ignore prefer-primordials
   const targetCopy = target.slice(start, end);
   for (let i = 0; i < len; ++i) {
     if (thisCopy[i] !== targetCopy[i]) {
@@ -590,7 +694,8 @@ function bidirectionalIndexOf(buffer, val, byteOffset, encoding, dir) {
     byteOffset = -0x80000000;
   }
   byteOffset = +byteOffset;
-  if (Number.isNaN(byteOffset)) {
+  if (NumberIsNaN(byteOffset)) {
+    // deno-lint-ignore prefer-primordials
     byteOffset = dir ? 0 : (buffer.length || buffer.byteLength);
   }
   dir = !!dir;
@@ -610,6 +715,7 @@ function bidirectionalIndexOf(buffer, val, byteOffset, encoding, dir) {
     if (ops === undefined) {
       throw new codes.ERR_UNKNOWN_ENCODING(encoding);
     }
+    // deno-lint-ignore prefer-primordials
     return ops.indexOf(buffer, val, byteOffset, dir);
   }
 
@@ -626,6 +732,7 @@ function bidirectionalIndexOf(buffer, val, byteOffset, encoding, dir) {
 }
 
 Buffer.prototype.includes = function includes(val, byteOffset, encoding) {
+  // deno-lint-ignore prefer-primordials
   return this.indexOf(val, byteOffset, encoding) !== -1;
 };
 
@@ -645,7 +752,7 @@ Buffer.prototype.asciiSlice = function asciiSlice(offset, length) {
   if (offset === 0 && length === this.length) {
     return bytesToAscii(this);
   } else {
-    return bytesToAscii(this.slice(offset, length));
+    return bytesToAscii(TypedArrayPrototypeSlice(this, offset, length));
   }
 };
 
@@ -660,7 +767,9 @@ Buffer.prototype.base64Slice = function base64Slice(
   if (offset === 0 && length === this.length) {
     return forgivingBase64Encode(this);
   } else {
-    return forgivingBase64Encode(this.slice(offset, length));
+    return forgivingBase64Encode(
+      TypedArrayPrototypeSlice(this, offset, length),
+    );
   }
 };
 
@@ -679,7 +788,9 @@ Buffer.prototype.base64urlSlice = function base64urlSlice(
   if (offset === 0 && length === this.length) {
     return forgivingBase64UrlEncode(this);
   } else {
-    return forgivingBase64UrlEncode(this.slice(offset, length));
+    return forgivingBase64UrlEncode(
+      TypedArrayPrototypeSlice(this, offset, length),
+    );
   }
 };
 
@@ -724,7 +835,7 @@ Buffer.prototype.ucs2Slice = function ucs2Slice(offset, length) {
   if (offset === 0 && length === this.length) {
     return bytesToUtf16le(this);
   } else {
-    return bytesToUtf16le(this.slice(offset, length));
+    return bytesToUtf16le(TypedArrayPrototypeSlice(this, offset, length));
   }
 };
 
@@ -743,9 +854,9 @@ Buffer.prototype.utf8Slice = function utf8Slice(string, offset, length) {
 
 Buffer.prototype.utf8Write = function utf8Write(string, offset, length) {
   offset = offset || 0;
-  const maxLength = Math.min(length || Infinity, this.length - offset);
+  const maxLength = MathMin(length || Infinity, this.length - offset);
   const buf = offset || maxLength < this.length
-    ? this.subarray(offset, maxLength + offset)
+    ? TypedArrayPrototypeSubarray(this, offset, maxLength + offset)
     : this;
   return utf8Encoder.encodeInto(string, buf).written;
 };
@@ -797,7 +908,7 @@ Buffer.prototype.write = function write(string, offset, length, encoding) {
 Buffer.prototype.toJSON = function toJSON() {
   return {
     type: "Buffer",
-    data: Array.prototype.slice.call(this._arr || this, 0),
+    data: ArrayPrototypeSlice(this._arr || this, 0),
   };
 };
 function fromArrayBuffer(obj, byteOffset, length) {
@@ -806,11 +917,12 @@ function fromArrayBuffer(obj, byteOffset, length) {
     byteOffset = 0;
   } else {
     byteOffset = +byteOffset;
-    if (Number.isNaN(byteOffset)) {
+    if (NumberIsNaN(byteOffset)) {
       byteOffset = 0;
     }
   }
 
+  // deno-lint-ignore prefer-primordials
   const maxLength = obj.byteLength - byteOffset;
 
   if (maxLength < 0) {
@@ -832,7 +944,7 @@ function fromArrayBuffer(obj, byteOffset, length) {
   }
 
   const buffer = new Uint8Array(obj, byteOffset, length);
-  Object.setPrototypeOf(buffer, Buffer.prototype);
+  ObjectSetPrototypeOf(buffer, BufferPrototype);
   return buffer;
 }
 
@@ -840,6 +952,7 @@ function _base64Slice(buf, start, end) {
   if (start === 0 && end === buf.length) {
     return forgivingBase64Encode(buf);
   } else {
+    // deno-lint-ignore prefer-primordials
     return forgivingBase64Encode(buf.slice(start, end));
   }
 }
@@ -848,9 +961,10 @@ const decoder = new TextDecoder();
 
 function _utf8Slice(buf, start, end) {
   try {
+    // deno-lint-ignore prefer-primordials
     return decoder.decode(buf.slice(start, end));
   } catch (err) {
-    if (err instanceof TypeError) {
+    if (ObjectPrototypeIsPrototypeOf(TypeErrorPrototype, err)) {
       throw new NodeError("ERR_STRING_TOO_LONG", "String too long");
     }
     throw err;
@@ -859,9 +973,9 @@ function _utf8Slice(buf, start, end) {
 
 function _latin1Slice(buf, start, end) {
   let ret = "";
-  end = Math.min(buf.length, end);
+  end = MathMin(buf.length, end);
   for (let i = start; i < end; ++i) {
-    ret += String.fromCharCode(buf[i]);
+    ret += StringFromCharCode(buf[i]);
   }
   return ret;
 }
@@ -990,42 +1104,38 @@ Buffer.prototype.readUint32BE = Buffer.prototype.readUInt32BE = readUInt32BE;
 
 Buffer.prototype.readBigUint64LE =
   Buffer.prototype.readBigUInt64LE =
-    defineBigIntMethod(
-      function readBigUInt64LE(offset) {
-        offset = offset >>> 0;
-        validateNumber(offset, "offset");
-        const first = this[offset];
-        const last = this[offset + 7];
-        if (first === void 0 || last === void 0) {
-          boundsError(offset, this.length - 8);
-        }
-        const lo = first + this[++offset] * 2 ** 8 +
-          this[++offset] * 2 ** 16 +
-          this[++offset] * 2 ** 24;
-        const hi = this[++offset] + this[++offset] * 2 ** 8 +
-          this[++offset] * 2 ** 16 + last * 2 ** 24;
-        return BigInt(lo) + (BigInt(hi) << BigInt(32));
-      },
-    );
+    function readBigUInt64LE(offset) {
+      offset = offset >>> 0;
+      validateNumber(offset, "offset");
+      const first = this[offset];
+      const last = this[offset + 7];
+      if (first === void 0 || last === void 0) {
+        boundsError(offset, this.length - 8);
+      }
+      const lo = first + this[++offset] * 2 ** 8 +
+        this[++offset] * 2 ** 16 +
+        this[++offset] * 2 ** 24;
+      const hi = this[++offset] + this[++offset] * 2 ** 8 +
+        this[++offset] * 2 ** 16 + last * 2 ** 24;
+      return BigInt(lo) + (BigInt(hi) << 32n);
+    };
 
 Buffer.prototype.readBigUint64BE =
   Buffer.prototype.readBigUInt64BE =
-    defineBigIntMethod(
-      function readBigUInt64BE(offset) {
-        offset = offset >>> 0;
-        validateNumber(offset, "offset");
-        const first = this[offset];
-        const last = this[offset + 7];
-        if (first === void 0 || last === void 0) {
-          boundsError(offset, this.length - 8);
-        }
-        const hi = first * 2 ** 24 + this[++offset] * 2 ** 16 +
-          this[++offset] * 2 ** 8 + this[++offset];
-        const lo = this[++offset] * 2 ** 24 + this[++offset] * 2 ** 16 +
-          this[++offset] * 2 ** 8 + last;
-        return (BigInt(hi) << BigInt(32)) + BigInt(lo);
-      },
-    );
+    function readBigUInt64BE(offset) {
+      offset = offset >>> 0;
+      validateNumber(offset, "offset");
+      const first = this[offset];
+      const last = this[offset + 7];
+      if (first === void 0 || last === void 0) {
+        boundsError(offset, this.length - 8);
+      }
+      const hi = first * 2 ** 24 + this[++offset] * 2 ** 16 +
+        this[++offset] * 2 ** 8 + this[++offset];
+      const lo = this[++offset] * 2 ** 24 + this[++offset] * 2 ** 16 +
+        this[++offset] * 2 ** 8 + last;
+      return (BigInt(hi) << 32n) + BigInt(lo);
+    };
 
 Buffer.prototype.readIntLE = function readIntLE(
   offset,
@@ -1144,43 +1254,39 @@ Buffer.prototype.readInt32BE = function readInt32BE(offset = 0) {
     last;
 };
 
-Buffer.prototype.readBigInt64LE = defineBigIntMethod(
-  function readBigInt64LE(offset) {
-    offset = offset >>> 0;
-    validateNumber(offset, "offset");
-    const first = this[offset];
-    const last = this[offset + 7];
-    if (first === void 0 || last === void 0) {
-      boundsError(offset, this.length - 8);
-    }
-    const val = this[offset + 4] + this[offset + 5] * 2 ** 8 +
-      this[offset + 6] * 2 ** 16 + (last << 24);
-    return (BigInt(val) << BigInt(32)) +
-      BigInt(
-        first + this[++offset] * 2 ** 8 + this[++offset] * 2 ** 16 +
-          this[++offset] * 2 ** 24,
-      );
-  },
-);
+Buffer.prototype.readBigInt64LE = function readBigInt64LE(offset) {
+  offset = offset >>> 0;
+  validateNumber(offset, "offset");
+  const first = this[offset];
+  const last = this[offset + 7];
+  if (first === void 0 || last === void 0) {
+    boundsError(offset, this.length - 8);
+  }
+  const val = this[offset + 4] + this[offset + 5] * 2 ** 8 +
+    this[offset + 6] * 2 ** 16 + (last << 24);
+  return (BigInt(val) << 32n) +
+    BigInt(
+      first + this[++offset] * 2 ** 8 + this[++offset] * 2 ** 16 +
+        this[++offset] * 2 ** 24,
+    );
+};
 
-Buffer.prototype.readBigInt64BE = defineBigIntMethod(
-  function readBigInt64BE(offset) {
-    offset = offset >>> 0;
-    validateNumber(offset, "offset");
-    const first = this[offset];
-    const last = this[offset + 7];
-    if (first === void 0 || last === void 0) {
-      boundsError(offset, this.length - 8);
-    }
-    const val = (first << 24) + this[++offset] * 2 ** 16 +
-      this[++offset] * 2 ** 8 + this[++offset];
-    return (BigInt(val) << BigInt(32)) +
-      BigInt(
-        this[++offset] * 2 ** 24 + this[++offset] * 2 ** 16 +
-          this[++offset] * 2 ** 8 + last,
-      );
-  },
-);
+Buffer.prototype.readBigInt64BE = function readBigInt64BE(offset) {
+  offset = offset >>> 0;
+  validateNumber(offset, "offset");
+  const first = this[offset];
+  const last = this[offset + 7];
+  if (first === void 0 || last === void 0) {
+    boundsError(offset, this.length - 8);
+  }
+  const val = (first << 24) + this[++offset] * 2 ** 16 +
+    this[++offset] * 2 ** 8 + this[++offset];
+  return (BigInt(val) << 32n) +
+    BigInt(
+      this[++offset] * 2 ** 24 + this[++offset] * 2 ** 16 +
+        this[++offset] * 2 ** 8 + last,
+    );
+};
 
 Buffer.prototype.readFloatLE = function readFloatLE(offset) {
   return bigEndian
@@ -1289,7 +1395,7 @@ Buffer.prototype.writeUint32BE =
 
 function wrtBigUInt64LE(buf, value, offset, min, max) {
   checkIntBI(value, min, max, buf, offset, 7);
-  let lo = Number(value & BigInt(4294967295));
+  let lo = Number(value & 4294967295n);
   buf[offset++] = lo;
   lo = lo >> 8;
   buf[offset++] = lo;
@@ -1297,7 +1403,7 @@ function wrtBigUInt64LE(buf, value, offset, min, max) {
   buf[offset++] = lo;
   lo = lo >> 8;
   buf[offset++] = lo;
-  let hi = Number(value >> BigInt(32) & BigInt(4294967295));
+  let hi = Number(value >> 32n & 4294967295n);
   buf[offset++] = hi;
   hi = hi >> 8;
   buf[offset++] = hi;
@@ -1310,7 +1416,7 @@ function wrtBigUInt64LE(buf, value, offset, min, max) {
 
 function wrtBigUInt64BE(buf, value, offset, min, max) {
   checkIntBI(value, min, max, buf, offset, 7);
-  let lo = Number(value & BigInt(4294967295));
+  let lo = Number(value & 4294967295n);
   buf[offset + 7] = lo;
   lo = lo >> 8;
   buf[offset + 6] = lo;
@@ -1318,7 +1424,7 @@ function wrtBigUInt64BE(buf, value, offset, min, max) {
   buf[offset + 5] = lo;
   lo = lo >> 8;
   buf[offset + 4] = lo;
-  let hi = Number(value >> BigInt(32) & BigInt(4294967295));
+  let hi = Number(value >> 32n & 4294967295n);
   buf[offset + 3] = hi;
   hi = hi >> 8;
   buf[offset + 2] = hi;
@@ -1331,31 +1437,27 @@ function wrtBigUInt64BE(buf, value, offset, min, max) {
 
 Buffer.prototype.writeBigUint64LE =
   Buffer.prototype.writeBigUInt64LE =
-    defineBigIntMethod(
-      function writeBigUInt64LE(value, offset = 0) {
-        return wrtBigUInt64LE(
-          this,
-          value,
-          offset,
-          BigInt(0),
-          BigInt("0xffffffffffffffff"),
-        );
-      },
-    );
+    function writeBigUInt64LE(value, offset = 0) {
+      return wrtBigUInt64LE(
+        this,
+        value,
+        offset,
+        0n,
+        0xffffffffffffffffn,
+      );
+    };
 
 Buffer.prototype.writeBigUint64BE =
   Buffer.prototype.writeBigUInt64BE =
-    defineBigIntMethod(
-      function writeBigUInt64BE(value, offset = 0) {
-        return wrtBigUInt64BE(
-          this,
-          value,
-          offset,
-          BigInt(0),
-          BigInt("0xffffffffffffffff"),
-        );
-      },
-    );
+    function writeBigUInt64BE(value, offset = 0) {
+      return wrtBigUInt64BE(
+        this,
+        value,
+        offset,
+        0n,
+        0xffffffffffffffffn,
+      );
+    };
 
 Buffer.prototype.writeIntLE = function writeIntLE(
   value,
@@ -1446,29 +1548,25 @@ Buffer.prototype.writeInt32BE = function writeInt32BE(value, offset = 0) {
   return writeU_Int32BE(this, value, offset, -0x80000000, 0x7fffffff);
 };
 
-Buffer.prototype.writeBigInt64LE = defineBigIntMethod(
-  function writeBigInt64LE(value, offset = 0) {
-    return wrtBigUInt64LE(
-      this,
-      value,
-      offset,
-      -BigInt("0x8000000000000000"),
-      BigInt("0x7fffffffffffffff"),
-    );
-  },
-);
+Buffer.prototype.writeBigInt64LE = function writeBigInt64LE(value, offset = 0) {
+  return wrtBigUInt64LE(
+    this,
+    value,
+    offset,
+    -0x8000000000000000n,
+    0x7fffffffffffffffn,
+  );
+};
 
-Buffer.prototype.writeBigInt64BE = defineBigIntMethod(
-  function writeBigInt64BE(value, offset = 0) {
-    return wrtBigUInt64BE(
-      this,
-      value,
-      offset,
-      -BigInt("0x8000000000000000"),
-      BigInt("0x7fffffffffffffff"),
-    );
-  },
-);
+Buffer.prototype.writeBigInt64BE = function writeBigInt64BE(value, offset = 0) {
+  return wrtBigUInt64BE(
+    this,
+    value,
+    offset,
+    -0x8000000000000000n,
+    0x7fffffffffffffffn,
+  );
+};
 
 Buffer.prototype.writeFloatLE = function writeFloatLE(
   value,
@@ -1596,14 +1694,12 @@ Buffer.prototype.copy = function copy(
   }
 
   const len = sourceEnd - sourceStart;
-  if (
-    this === target && typeof Uint8Array.prototype.copyWithin === "function"
-  ) {
-    this.copyWithin(targetStart, sourceStart, sourceEnd);
+  if (this === target) {
+    TypedArrayPrototypeCopyWithin(this, targetStart, sourceStart, sourceEnd);
   } else {
-    Uint8Array.prototype.set.call(
+    TypedArrayPrototypeSet(
       target,
-      this.subarray(sourceStart, sourceEnd),
+      TypedArrayPrototypeSubarray(this, sourceStart, sourceEnd),
       targetStart,
     );
   }
@@ -1623,11 +1719,11 @@ Buffer.prototype.fill = function fill(val, start, end, encoding) {
     if (encoding !== void 0 && typeof encoding !== "string") {
       throw new TypeError("encoding must be a string");
     }
-    if (typeof encoding === "string" && !Buffer.isEncoding(encoding)) {
+    if (typeof encoding === "string" && !BufferIsEncoding(encoding)) {
       throw new TypeError("Unknown encoding: " + encoding);
     }
     if (val.length === 1) {
-      const code = val.charCodeAt(0);
+      const code = StringPrototypeCharCodeAt(val, 0);
       if (encoding === "utf8" && code < 128 || encoding === "latin1") {
         val = code;
       }
@@ -1654,7 +1750,7 @@ Buffer.prototype.fill = function fill(val, start, end, encoding) {
       this[i] = val;
     }
   } else {
-    const bytes = Buffer.isBuffer(val) ? val : Buffer.from(val, encoding);
+    const bytes = BufferIsBuffer(val) ? val : BufferFrom(val, encoding);
     const len = bytes.length;
     if (len === 0) {
       throw new codes.ERR_INVALID_ARG_VALUE(
@@ -1681,7 +1777,7 @@ function checkIntBI(value, min, max, buf, offset, byteLength2) {
     const n = typeof min === "bigint" ? "n" : "";
     let range;
     if (byteLength2 > 3) {
-      if (min === 0 || min === BigInt(0)) {
+      if (min === 0 || min === 0n) {
         range = `>= 0${n} and < 2${n} ** ${(byteLength2 + 1) * 8}${n}`;
       } else {
         range = `>= -(2${n} ** ${(byteLength2 + 1) * 8 - 1}${n}) and < 2 ** ${
@@ -1706,7 +1802,7 @@ function checkIntBI(value, min, max, buf, offset, byteLength2) {
 function blitBuffer(src, dst, offset, byteLength = Infinity) {
   const srcLength = src.length;
   // Establish the number of bytes to be written
-  const bytesToWrite = Math.min(
+  const bytesToWrite = MathMin(
     // If byte length is defined in the call, then it sets an upper bound,
     // otherwise it is Infinity and is never chosen.
     byteLength,
@@ -1726,15 +1822,9 @@ function blitBuffer(src, dst, offset, byteLength = Infinity) {
   return bytesToWrite;
 }
 
-function isInstance(obj, type) {
-  return obj instanceof type ||
-    obj != null && obj.constructor != null &&
-      obj.constructor.name != null && obj.constructor.name === type.name;
-}
-
 const hexSliceLookupTable = function () {
   const alphabet = "0123456789abcdef";
-  const table = new Array(256);
+  const table = [];
   for (let i = 0; i < 16; ++i) {
     const i16 = i * 16;
     for (let j = 0; j < 16; ++j) {
@@ -1744,14 +1834,6 @@ const hexSliceLookupTable = function () {
   return table;
 }();
 
-function defineBigIntMethod(fn) {
-  return typeof BigInt === "undefined" ? BufferBigIntNotDefined : fn;
-}
-
-function BufferBigIntNotDefined() {
-  throw new Error("BigInt not supported");
-}
-
 export function readUInt48LE(buf, offset = 0) {
   validateNumber(offset, "offset");
   const first = buf[offset];
@@ -2075,10 +2157,10 @@ export function byteLengthUtf8(str) {
 
 function base64ByteLength(str, bytes) {
   // Handle padding
-  if (str.charCodeAt(bytes - 1) === 0x3D) {
+  if (StringPrototypeCharCodeAt(str, bytes - 1) === 0x3D) {
     bytes--;
   }
-  if (bytes > 1 && str.charCodeAt(bytes - 1) === 0x3D) {
+  if (bytes > 1 && StringPrototypeCharCodeAt(str, bytes - 1) === 0x3D) {
     bytes--;
   }
 
@@ -2086,7 +2168,7 @@ function base64ByteLength(str, bytes) {
   return (bytes * 3) >>> 2;
 }
 
-export const encodingsMap = Object.create(null);
+export const encodingsMap = ObjectCreate(null);
 for (let i = 0; i < encodings.length; ++i) {
   encodingsMap[encodings[i]] = i;
 }
@@ -2216,7 +2298,7 @@ export const encodingOps = {
 };
 
 export function getEncodingOps(encoding) {
-  encoding = String(encoding).toLowerCase();
+  encoding = StringPrototypeToLowerCase(String(encoding));
   switch (encoding.length) {
     case 4:
       if (encoding === "utf8") return encodingOps.utf8;
@@ -2256,6 +2338,14 @@ export function getEncodingOps(encoding) {
   }
 }
 
+/**
+ * @param {Buffer} source
+ * @param {Buffer} target
+ * @param {number} targetStart
+ * @param {number} sourceStart
+ * @param {number} sourceEnd
+ * @returns {number}
+ */
 export function _copyActual(
   source,
   target,
@@ -2274,6 +2364,7 @@ export function _copyActual(
   }
 
   if (sourceStart !== 0 || sourceEnd < source.length) {
+    // deno-lint-ignore prefer-primordials
     source = new Uint8Array(source.buffer, source.byteOffset + sourceStart, nb);
   }
 
@@ -2283,7 +2374,7 @@ export function _copyActual(
 }
 
 export function boundsError(value, length, type) {
-  if (Math.floor(value) !== value) {
+  if (MathFloor(value) !== value) {
     validateNumber(value, type);
     throw new codes.ERR_OUT_OF_RANGE(type || "offset", "an integer", value);
   }
@@ -2306,7 +2397,7 @@ export function validateNumber(value, name, min = undefined, max) {
 
   if (
     (min != null && value < min) || (max != null && value > max) ||
-    ((min != null || max != null) && Number.isNaN(value))
+    ((min != null || max != null) && NumberIsNaN(value))
   ) {
     throw new codes.ERR_OUT_OF_RANGE(
       name,
@@ -2340,11 +2431,11 @@ function checkInt(value, min, max, buf, offset, byteLength) {
 export function toInteger(n, defaultVal) {
   n = +n;
   if (
-    !Number.isNaN(n) &&
-    n >= Number.MIN_SAFE_INTEGER &&
-    n <= Number.MAX_SAFE_INTEGER
+    !NumberIsNaN(n) &&
+    n >= NumberMIN_SAFE_INTEGER &&
+    n <= NumberMAX_SAFE_INTEGER
   ) {
-    return ((n % 1) === 0 ? n : Math.floor(n));
+    return ((n % 1) === 0 ? n : MathFloor(n));
   }
   return defaultVal;
 }
@@ -2417,7 +2508,7 @@ export function writeU_Int48BE(buf, value, offset, min, max) {
   value = +value;
   checkInt(value, min, max, buf, offset, 5);
 
-  const newVal = Math.floor(value * 2 ** -32);
+  const newVal = MathFloor(value * 2 ** -32);
   buf[offset++] = newVal >>> 8;
   buf[offset++] = newVal;
   buf[offset + 3] = value;
@@ -2435,7 +2526,7 @@ export function writeU_Int40BE(buf, value, offset, min, max) {
   value = +value;
   checkInt(value, min, max, buf, offset, 4);
 
-  buf[offset++] = Math.floor(value * 2 ** -32);
+  buf[offset++] = MathFloor(value * 2 ** -32);
   buf[offset + 3] = value;
   value = value >>> 8;
   buf[offset + 2] = value;
@@ -2478,12 +2569,12 @@ export function validateOffset(
   value,
   name,
   min = 0,
-  max = Number.MAX_SAFE_INTEGER,
+  max = NumberMAX_SAFE_INTEGER,
 ) {
   if (typeof value !== "number") {
     throw new codes.ERR_INVALID_ARG_TYPE(name, "number", value);
   }
-  if (!Number.isInteger(value)) {
+  if (!NumberIsInteger(value)) {
     throw new codes.ERR_OUT_OF_RANGE(name, "an integer", value);
   }
   if (value < min || value > max) {
@@ -2496,7 +2587,7 @@ export function writeU_Int48LE(buf, value, offset, min, max) {
   value = +value;
   checkInt(value, min, max, buf, offset, 5);
 
-  const newVal = Math.floor(value * 2 ** -32);
+  const newVal = MathFloor(value * 2 ** -32);
   buf[offset++] = value;
   value = value >>> 8;
   buf[offset++] = value;
@@ -2522,7 +2613,7 @@ export function writeU_Int40LE(buf, value, offset, min, max) {
   buf[offset++] = value;
   value = value >>> 8;
   buf[offset++] = value;
-  buf[offset++] = Math.floor(newVal * 2 ** -32);
+  buf[offset++] = MathFloor(newVal * 2 ** -32);
   return offset;
 }
 
@@ -2556,14 +2647,14 @@ export function writeU_Int24LE(buf, value, offset, min, max) {
 
 export function isUtf8(input) {
   if (isTypedArray(input)) {
-    if (input.buffer.detached) {
+    if (isDetachedBuffer(TypedArrayPrototypeGetBuffer(input))) {
       throw new ERR_INVALID_STATE("Cannot validate on a detached buffer");
     }
     return op_is_utf8(input);
   }
 
   if (isAnyArrayBuffer(input)) {
-    if (input.detached) {
+    if (isDetachedBuffer(input)) {
       throw new ERR_INVALID_STATE("Cannot validate on a detached buffer");
     }
     return op_is_utf8(new Uint8Array(input));
@@ -2578,14 +2669,14 @@ export function isUtf8(input) {
 
 export function isAscii(input) {
   if (isTypedArray(input)) {
-    if (input.buffer.detached) {
+    if (isDetachedBuffer(TypedArrayPrototypeGetBuffer(input))) {
       throw new ERR_INVALID_STATE("Cannot validate on a detached buffer");
     }
     return op_is_ascii(input);
   }
 
   if (isAnyArrayBuffer(input)) {
-    if (input.detached) {
+    if (isDetachedBuffer(input)) {
       throw new ERR_INVALID_STATE("Cannot validate on a detached buffer");
     }
     return op_is_ascii(new Uint8Array(input));
@@ -2598,6 +2689,48 @@ export function isAscii(input) {
   ], input);
 }
 
+export function transcode(source, fromEnco, toEnco) {
+  if (!isUint8Array(source)) {
+    throw new codes.ERR_INVALID_ARG_TYPE(
+      "source",
+      ["Buffer", "Uint8Array"],
+      source,
+    );
+  }
+  if (source.length === 0) {
+    return Buffer.alloc(0);
+  }
+  const code = "U_ILLEGAL_ARGUMENT_ERROR";
+  const illegalArgumentError = genericNodeError(
+    `Unable to transcode Buffer [${code}]`,
+    { code: code, errno: 1 },
+  );
+  fromEnco = normalizeEncoding(fromEnco);
+  toEnco = normalizeEncoding(toEnco);
+  if (!fromEnco || !toEnco) {
+    throw illegalArgumentError;
+  }
+  // Return the provided source when transcode is not required
+  // for the from/to encoding pair.
+  const returnSource = fromEnco === toEnco ||
+    fromEnco === "ascii" && toEnco === "utf8" ||
+    fromEnco === "ascii" && toEnco === "latin1";
+  if (returnSource) {
+    return Buffer.from(source);
+  }
+
+  try {
+    const result = op_transcode(new Uint8Array(source), fromEnco, toEnco);
+    return Buffer.from(result, toEnco);
+  } catch (err) {
+    if (StringPrototypeIncludes(err.message, "Unable to transcode Buffer")) {
+      throw illegalArgumentError;
+    } else {
+      throw err;
+    }
+  }
+}
+
 export default {
   atob,
   btoa,
@@ -2610,4 +2743,5 @@ export default {
   kMaxLength,
   kStringMaxLength,
   SlowBuffer,
+  transcode,
 };
diff --git a/ext/node/polyfills/internal/child_process.ts b/ext/node/polyfills/internal/child_process.ts
index 6f209b7192..cfff1079ff 100644
--- a/ext/node/polyfills/internal/child_process.ts
+++ b/ext/node/polyfills/internal/child_process.ts
@@ -1191,8 +1191,12 @@ function toDenoArgs(args: string[]): string[] {
     }
 
     if (flagInfo === undefined) {
-      // Not a known flag that expects a value. Just copy it to the output.
-      denoArgs.push(arg);
+      if (arg === "--no-warnings") {
+        denoArgs.push("--quiet");
+      } else {
+        // Not a known flag that expects a value. Just copy it to the output.
+        denoArgs.push(arg);
+      }
       continue;
     }
 
@@ -1335,7 +1339,7 @@ export function setupChannel(target: any, ipc: number) {
           }
         }
 
-        process.nextTick(handleMessage, msg);
+        nextTick(handleMessage, msg);
       }
     } catch (err) {
       if (
@@ -1396,7 +1400,7 @@ export function setupChannel(target: any, ipc: number) {
     if (!target.connected) {
       const err = new ERR_IPC_CHANNEL_CLOSED();
       if (typeof callback === "function") {
-        process.nextTick(callback, err);
+        nextTick(callback, err);
       } else {
         nextTick(() => target.emit("error", err));
       }
@@ -1412,7 +1416,18 @@ export function setupChannel(target: any, ipc: number) {
       .then(() => {
         control.unrefCounted();
         if (callback) {
-          process.nextTick(callback, null);
+          nextTick(callback, null);
+        }
+      }, (err: Error) => {
+        control.unrefCounted();
+        if (err instanceof Deno.errors.Interrupted) {
+          // Channel closed on us mid-write.
+        } else {
+          if (typeof callback === "function") {
+            nextTick(callback, err);
+          } else {
+            nextTick(() => target.emit("error", err));
+          }
         }
       });
     return queueOk[0];
@@ -1429,7 +1444,7 @@ export function setupChannel(target: any, ipc: number) {
     target.connected = false;
     target[kCanDisconnect] = false;
     control[kControlDisconnect]();
-    process.nextTick(() => {
+    nextTick(() => {
       target.channel = null;
       core.close(ipc);
       target.emit("disconnect");
diff --git a/ext/node/polyfills/internal/crypto/_randomInt.ts b/ext/node/polyfills/internal/crypto/_randomInt.ts
index 7f4d703ad4..e08b3e9639 100644
--- a/ext/node/polyfills/internal/crypto/_randomInt.ts
+++ b/ext/node/polyfills/internal/crypto/_randomInt.ts
@@ -1,9 +1,15 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-// TODO(petamoriken): enable prefer-primordials for node polyfills
-// deno-lint-ignore-file prefer-primordials
-
 import { op_node_random_int } from "ext:core/ops";
+import { primordials } from "ext:core/mod.js";
+const {
+  Error,
+  MathCeil,
+  MathFloor,
+  MathPow,
+  NumberIsSafeInteger,
+  RangeError,
+} = primordials;
 
 export default function randomInt(max: number): number;
 export default function randomInt(min: number, max: number): number;
@@ -23,7 +29,9 @@ export default function randomInt(
   cb?: (err: Error | null, n?: number) => void,
 ): number | void {
   if (typeof max === "number" && typeof min === "number") {
-    [max, min] = [min, max];
+    const temp = max;
+    max = min;
+    min = temp;
   }
   if (min === undefined) min = 0;
   else if (typeof min === "function") {
@@ -32,13 +40,13 @@ export default function randomInt(
   }
 
   if (
-    !Number.isSafeInteger(min) ||
-    typeof max === "number" && !Number.isSafeInteger(max)
+    !NumberIsSafeInteger(min) ||
+    typeof max === "number" && !NumberIsSafeInteger(max)
   ) {
     throw new Error("max or min is not a Safe Number");
   }
 
-  if (max - min > Math.pow(2, 48)) {
+  if (max - min > MathPow(2, 48)) {
     throw new RangeError("max - min should be less than 2^48!");
   }
 
@@ -46,8 +54,8 @@ export default function randomInt(
     throw new Error("Min is bigger than Max!");
   }
 
-  min = Math.ceil(min);
-  max = Math.floor(max);
+  min = MathCeil(min);
+  max = MathFloor(max);
   const result = op_node_random_int(min, max);
 
   if (cb) {
diff --git a/ext/node/polyfills/internal/crypto/keygen.ts b/ext/node/polyfills/internal/crypto/keygen.ts
index a40c76c0d7..44bfd83277 100644
--- a/ext/node/polyfills/internal/crypto/keygen.ts
+++ b/ext/node/polyfills/internal/crypto/keygen.ts
@@ -29,6 +29,7 @@ import {
 } from "ext:deno_node/internal/validators.mjs";
 import { Buffer } from "node:buffer";
 import { KeyFormat, KeyType } from "ext:deno_node/internal/crypto/types.ts";
+import process from "node:process";
 
 import {
   op_node_generate_dh_group_key,
diff --git a/ext/node/polyfills/internal/crypto/random.ts b/ext/node/polyfills/internal/crypto/random.ts
index 4219414dc1..a41b868190 100644
--- a/ext/node/polyfills/internal/crypto/random.ts
+++ b/ext/node/polyfills/internal/crypto/random.ts
@@ -38,6 +38,7 @@ import {
   ERR_INVALID_ARG_TYPE,
   ERR_OUT_OF_RANGE,
 } from "ext:deno_node/internal/errors.ts";
+import { Buffer } from "node:buffer";
 
 export { default as randomBytes } from "ext:deno_node/internal/crypto/_randomBytes.ts";
 export {
diff --git a/ext/node/polyfills/internal/errors.ts b/ext/node/polyfills/internal/errors.ts
index 51bd7a0250..61b53fa968 100644
--- a/ext/node/polyfills/internal/errors.ts
+++ b/ext/node/polyfills/internal/errors.ts
@@ -18,7 +18,7 @@
  */
 
 import { primordials } from "ext:core/mod.js";
-const { JSONStringify, SymbolFor } = primordials;
+const { JSONStringify, SafeArrayIterator, SymbolFor } = primordials;
 import { format, inspect } from "ext:deno_node/internal/util/inspect.mjs";
 import { codes } from "ext:deno_node/internal/error_codes.ts";
 import {
@@ -1874,6 +1874,11 @@ export class ERR_SOCKET_CLOSED extends NodeError {
     super("ERR_SOCKET_CLOSED", `Socket is closed`);
   }
 }
+export class ERR_SOCKET_CONNECTION_TIMEOUT extends NodeError {
+  constructor() {
+    super("ERR_SOCKET_CONNECTION_TIMEOUT", `Socket connection timeout`);
+  }
+}
 export class ERR_SOCKET_DGRAM_IS_CONNECTED extends NodeError {
   constructor() {
     super("ERR_SOCKET_DGRAM_IS_CONNECTED", `Already connected`);
@@ -2385,6 +2390,15 @@ export class ERR_INVALID_RETURN_VALUE extends NodeTypeError {
   }
 }
 
+export class ERR_NOT_IMPLEMENTED extends NodeError {
+  constructor(message?: string) {
+    super(
+      "ERR_NOT_IMPLEMENTED",
+      message ? `Not implemented: ${message}` : "Not implemented",
+    );
+  }
+}
+
 export class ERR_INVALID_URL extends NodeTypeError {
   input: string;
   constructor(input: string) {
@@ -2558,19 +2572,6 @@ export class ERR_FS_RMDIR_ENOTDIR extends NodeSystemError {
   }
 }
 
-export class ERR_OS_NO_HOMEDIR extends NodeSystemError {
-  constructor() {
-    const code = isWindows ? "ENOENT" : "ENOTDIR";
-    const ctx: NodeSystemErrorCtx = {
-      message: "not a directory",
-      syscall: "home",
-      code,
-      errno: isWindows ? osConstants.errno.ENOENT : osConstants.errno.ENOTDIR,
-    };
-    super(code, ctx, "Path is not a directory");
-  }
-}
-
 export class ERR_HTTP_SOCKET_ASSIGNED extends NodeError {
   constructor() {
     super(
@@ -2646,11 +2647,30 @@ export function aggregateTwoErrors(
   }
   return innerError || outerError;
 }
+
+export class NodeAggregateError extends AggregateError {
+  code: string;
+  constructor(errors, message) {
+    super(new SafeArrayIterator(errors), message);
+    this.code = errors[0]?.code;
+  }
+
+  get [kIsNodeError]() {
+    return true;
+  }
+
+  // deno-lint-ignore adjacent-overload-signatures
+  get ["constructor"]() {
+    return AggregateError;
+  }
+}
+
 codes.ERR_IPC_CHANNEL_CLOSED = ERR_IPC_CHANNEL_CLOSED;
 codes.ERR_INVALID_ARG_TYPE = ERR_INVALID_ARG_TYPE;
 codes.ERR_INVALID_ARG_VALUE = ERR_INVALID_ARG_VALUE;
 codes.ERR_OUT_OF_RANGE = ERR_OUT_OF_RANGE;
 codes.ERR_SOCKET_BAD_PORT = ERR_SOCKET_BAD_PORT;
+codes.ERR_SOCKET_CONNECTION_TIMEOUT = ERR_SOCKET_CONNECTION_TIMEOUT;
 codes.ERR_BUFFER_OUT_OF_BOUNDS = ERR_BUFFER_OUT_OF_BOUNDS;
 codes.ERR_UNKNOWN_ENCODING = ERR_UNKNOWN_ENCODING;
 codes.ERR_PARSE_ARGS_INVALID_OPTION_VALUE = ERR_PARSE_ARGS_INVALID_OPTION_VALUE;
@@ -2851,6 +2871,7 @@ export default {
   ERR_INVALID_SYNC_FORK_INPUT,
   ERR_INVALID_THIS,
   ERR_INVALID_TUPLE,
+  ERR_NOT_IMPLEMENTED,
   ERR_INVALID_URI,
   ERR_INVALID_URL,
   ERR_INVALID_URL_SCHEME,
diff --git a/ext/node/polyfills/internal/net.ts b/ext/node/polyfills/internal/net.ts
index 144612626f..a3dcb3ed21 100644
--- a/ext/node/polyfills/internal/net.ts
+++ b/ext/node/polyfills/internal/net.ts
@@ -95,4 +95,5 @@ export function makeSyncWrite(fd: number) {
   };
 }
 
+export const kReinitializeHandle = Symbol("kReinitializeHandle");
 export const normalizedArgsSymbol = Symbol("normalizedArgs");
diff --git a/ext/node/polyfills/internal/util/inspect.mjs b/ext/node/polyfills/internal/util/inspect.mjs
index 3a61c387c0..ae797449bf 100644
--- a/ext/node/polyfills/internal/util/inspect.mjs
+++ b/ext/node/polyfills/internal/util/inspect.mjs
@@ -565,6 +565,19 @@ export function stripVTControlCharacters(str) {
 
 export function styleText(format, text) {
   validateString(text, "text");
+
+  if (Array.isArray(format)) {
+    for (let i = 0; i < format.length; i++) {
+      const item = format[i];
+      const formatCodes = inspect.colors[item];
+      if (formatCodes == null) {
+        validateOneOf(item, "format", Object.keys(inspect.colors));
+      }
+      text = `\u001b[${formatCodes[0]}m${text}\u001b[${formatCodes[1]}m`;
+    }
+    return text;
+  }
+
   const formatCodes = inspect.colors[format];
   if (formatCodes == null) {
     validateOneOf(format, "format", Object.keys(inspect.colors));
diff --git a/ext/node/polyfills/internal_binding/_timingSafeEqual.ts b/ext/node/polyfills/internal_binding/_timingSafeEqual.ts
index ff141fdbfc..559b7685b8 100644
--- a/ext/node/polyfills/internal_binding/_timingSafeEqual.ts
+++ b/ext/node/polyfills/internal_binding/_timingSafeEqual.ts
@@ -5,10 +5,11 @@
 
 import { Buffer } from "node:buffer";
 
-function assert(cond) {
-  if (!cond) {
-    throw new Error("assertion failed");
+function toDataView(ab: ArrayBufferLike | ArrayBufferView): DataView {
+  if (ArrayBuffer.isView(ab)) {
+    return new DataView(ab.buffer, ab.byteOffset, ab.byteLength);
   }
+  return new DataView(ab);
 }
 
 /** Compare to array buffers or data views in a way that timing based attacks
@@ -21,13 +22,11 @@ function stdTimingSafeEqual(
     return false;
   }
   if (!(a instanceof DataView)) {
-    a = new DataView(ArrayBuffer.isView(a) ? a.buffer : a);
+    a = toDataView(a);
   }
   if (!(b instanceof DataView)) {
-    b = new DataView(ArrayBuffer.isView(b) ? b.buffer : b);
+    b = toDataView(b);
   }
-  assert(a instanceof DataView);
-  assert(b instanceof DataView);
   const length = a.byteLength;
   let out = 0;
   let i = -1;
@@ -41,7 +40,11 @@ export const timingSafeEqual = (
   a: Buffer | DataView | ArrayBuffer,
   b: Buffer | DataView | ArrayBuffer,
 ): boolean => {
-  if (a instanceof Buffer) a = new DataView(a.buffer);
-  if (a instanceof Buffer) b = new DataView(a.buffer);
+  if (a instanceof Buffer) {
+    a = new DataView(a.buffer, a.byteOffset, a.byteLength);
+  }
+  if (b instanceof Buffer) {
+    b = new DataView(b.buffer, b.byteOffset, b.byteLength);
+  }
   return stdTimingSafeEqual(a, b);
 };
diff --git a/ext/node/polyfills/internal_binding/http_parser.ts b/ext/node/polyfills/internal_binding/http_parser.ts
new file mode 100644
index 0000000000..bad10d9851
--- /dev/null
+++ b/ext/node/polyfills/internal_binding/http_parser.ts
@@ -0,0 +1,160 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+// Copyright Joyent, Inc. and other Node contributors.
+//
+// Permission is hereby granted, free of charge, to any person obtaining a
+// copy of this software and associated documentation files (the
+// "Software"), to deal in the Software without restriction, including
+// without limitation the rights to use, copy, modify, merge, publish,
+// distribute, sublicense, and/or sell copies of the Software, and to permit
+// persons to whom the Software is furnished to do so, subject to the
+// following conditions:
+//
+// The above copyright notice and this permission notice shall be included
+// in all copies or substantial portions of the Software.
+//
+// THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS
+// OR IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF
+// MERCHANTABILITY, FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN
+// NO EVENT SHALL THE AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM,
+// DAMAGES OR OTHER LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR
+// OTHERWISE, ARISING FROM, OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE
+// USE OR OTHER DEALINGS IN THE SOFTWARE.
+
+import { primordials } from "ext:core/mod.js";
+import { AsyncWrap } from "ext:deno_node/internal_binding/async_wrap.ts";
+
+const {
+  ObjectDefineProperty,
+  ObjectEntries,
+  ObjectSetPrototypeOf,
+  SafeArrayIterator,
+} = primordials;
+
+export const methods = [
+  "DELETE",
+  "GET",
+  "HEAD",
+  "POST",
+  "PUT",
+  "CONNECT",
+  "OPTIONS",
+  "TRACE",
+  "COPY",
+  "LOCK",
+  "MKCOL",
+  "MOVE",
+  "PROPFIND",
+  "PROPPATCH",
+  "SEARCH",
+  "UNLOCK",
+  "BIND",
+  "REBIND",
+  "UNBIND",
+  "ACL",
+  "REPORT",
+  "MKACTIVITY",
+  "CHECKOUT",
+  "MERGE",
+  "M-SEARCH",
+  "NOTIFY",
+  "SUBSCRIBE",
+  "UNSUBSCRIBE",
+  "PATCH",
+  "PURGE",
+  "MKCALENDAR",
+  "LINK",
+  "UNLINK",
+  "SOURCE",
+  "QUERY",
+];
+
+export const allMethods = [
+  "DELETE",
+  "GET",
+  "HEAD",
+  "POST",
+  "PUT",
+  "CONNECT",
+  "OPTIONS",
+  "TRACE",
+  "COPY",
+  "LOCK",
+  "MKCOL",
+  "MOVE",
+  "PROPFIND",
+  "PROPPATCH",
+  "SEARCH",
+  "UNLOCK",
+  "BIND",
+  "REBIND",
+  "UNBIND",
+  "ACL",
+  "REPORT",
+  "MKACTIVITY",
+  "CHECKOUT",
+  "MERGE",
+  "M-SEARCH",
+  "NOTIFY",
+  "SUBSCRIBE",
+  "UNSUBSCRIBE",
+  "PATCH",
+  "PURGE",
+  "MKCALENDAR",
+  "LINK",
+  "UNLINK",
+  "SOURCE",
+  "PRI",
+  "DESCRIBE",
+  "ANNOUNCE",
+  "SETUP",
+  "PLAY",
+  "PAUSE",
+  "TEARDOWN",
+  "GET_PARAMETER",
+  "SET_PARAMETER",
+  "REDIRECT",
+  "RECORD",
+  "FLUSH",
+  "QUERY",
+];
+
+export function HTTPParser() {
+}
+
+ObjectSetPrototypeOf(HTTPParser.prototype, AsyncWrap.prototype);
+
+function defineProps(obj: object, props: Record<string, unknown>) {
+  for (const entry of new SafeArrayIterator(ObjectEntries(props))) {
+    ObjectDefineProperty(obj, entry[0], {
+      __proto__: null,
+      value: entry[1],
+      enumerable: true,
+      writable: true,
+      configurable: true,
+    });
+  }
+}
+
+defineProps(HTTPParser, {
+  REQUEST: 1,
+  RESPONSE: 2,
+  kOnMessageBegin: 0,
+  kOnHeaders: 1,
+  kOnHeadersComplete: 2,
+  kOnBody: 3,
+  kOnMessageComplete: 4,
+  kOnExecute: 5,
+  kOnTimeout: 6,
+  kLenientNone: 0,
+  kLenientHeaders: 1,
+  kLenientChunkedLength: 2,
+  kLenientKeepAlive: 4,
+  kLenientTransferEncoding: 8,
+  kLenientVersion: 16,
+  kLenientDataAfterClose: 32,
+  kLenientOptionalLFAfterCR: 64,
+  kLenientOptionalCRLFAfterChunk: 128,
+  kLenientOptionalCRBeforeLF: 256,
+  kLenientSpacesAfterChunkSize: 512,
+  kLenientAll: 1023,
+});
diff --git a/ext/node/polyfills/internal_binding/mod.ts b/ext/node/polyfills/internal_binding/mod.ts
index f2d7f55bc7..ebbfc629f1 100644
--- a/ext/node/polyfills/internal_binding/mod.ts
+++ b/ext/node/polyfills/internal_binding/mod.ts
@@ -17,6 +17,7 @@ import * as types from "ext:deno_node/internal_binding/types.ts";
 import * as udpWrap from "ext:deno_node/internal_binding/udp_wrap.ts";
 import * as util from "ext:deno_node/internal_binding/util.ts";
 import * as uv from "ext:deno_node/internal_binding/uv.ts";
+import * as httpParser from "ext:deno_node/internal_binding/http_parser.ts";
 
 const modules = {
   "async_wrap": asyncWrap,
@@ -32,7 +33,7 @@ const modules = {
   "fs_dir": {},
   "fs_event_wrap": {},
   "heap_utils": {},
-  "http_parser": {},
+  "http_parser": httpParser,
   icu: {},
   inspector: {},
   "js_stream": {},
diff --git a/ext/node/polyfills/internal_binding/tcp_wrap.ts b/ext/node/polyfills/internal_binding/tcp_wrap.ts
index 973a1d1c01..d9f1c5356a 100644
--- a/ext/node/polyfills/internal_binding/tcp_wrap.ts
+++ b/ext/node/polyfills/internal_binding/tcp_wrap.ts
@@ -299,8 +299,10 @@ export class TCP extends ConnectionWrap {
    * @param noDelay
    * @return An error status code.
    */
-  setNoDelay(_noDelay: boolean): number {
-    // TODO(bnoordhuis) https://github.com/denoland/deno/pull/13103
+  setNoDelay(noDelay: boolean): number {
+    if (this[kStreamBaseField] && "setNoDelay" in this[kStreamBaseField]) {
+      this[kStreamBaseField].setNoDelay(noDelay);
+    }
     return 0;
   }
 
diff --git a/ext/node/polyfills/internal_binding/uv.ts b/ext/node/polyfills/internal_binding/uv.ts
index aa468a0a58..6cd70a7e85 100644
--- a/ext/node/polyfills/internal_binding/uv.ts
+++ b/ext/node/polyfills/internal_binding/uv.ts
@@ -530,10 +530,12 @@ export function mapSysErrnoToUvErrno(sysErrno: number): number {
 
 export const UV_EAI_MEMORY = codeMap.get("EAI_MEMORY")!;
 export const UV_EBADF = codeMap.get("EBADF")!;
+export const UV_ECANCELED = codeMap.get("ECANCELED")!;
 export const UV_EEXIST = codeMap.get("EEXIST");
 export const UV_EINVAL = codeMap.get("EINVAL")!;
 export const UV_ENOENT = codeMap.get("ENOENT");
 export const UV_ENOTSOCK = codeMap.get("ENOTSOCK")!;
+export const UV_ETIMEDOUT = codeMap.get("ETIMEDOUT")!;
 export const UV_UNKNOWN = codeMap.get("UNKNOWN")!;
 
 export function errname(errno: number): string {
diff --git a/ext/node/polyfills/net.ts b/ext/node/polyfills/net.ts
index 48e1d0de87..2b01125190 100644
--- a/ext/node/polyfills/net.ts
+++ b/ext/node/polyfills/net.ts
@@ -31,6 +31,7 @@ import {
   isIP,
   isIPv4,
   isIPv6,
+  kReinitializeHandle,
   normalizedArgsSymbol,
 } from "ext:deno_node/internal/net.ts";
 import { Duplex } from "node:stream";
@@ -50,9 +51,11 @@ import {
   ERR_SERVER_ALREADY_LISTEN,
   ERR_SERVER_NOT_RUNNING,
   ERR_SOCKET_CLOSED,
+  ERR_SOCKET_CONNECTION_TIMEOUT,
   errnoException,
   exceptionWithHostPort,
   genericNodeError,
+  NodeAggregateError,
   uvExceptionWithHostPort,
 } from "ext:deno_node/internal/errors.ts";
 import type { ErrnoException } from "ext:deno_node/internal/errors.ts";
@@ -80,6 +83,7 @@ import { Buffer } from "node:buffer";
 import type { LookupOneOptions } from "ext:deno_node/internal/dns/utils.ts";
 import {
   validateAbortSignal,
+  validateBoolean,
   validateFunction,
   validateInt32,
   validateNumber,
@@ -100,13 +104,25 @@ import { ShutdownWrap } from "ext:deno_node/internal_binding/stream_wrap.ts";
 import { assert } from "ext:deno_node/_util/asserts.ts";
 import { isWindows } from "ext:deno_node/_util/os.ts";
 import { ADDRCONFIG, lookup as dnsLookup } from "node:dns";
-import { codeMap } from "ext:deno_node/internal_binding/uv.ts";
+import {
+  codeMap,
+  UV_ECANCELED,
+  UV_ETIMEDOUT,
+} from "ext:deno_node/internal_binding/uv.ts";
 import { guessHandleType } from "ext:deno_node/internal_binding/util.ts";
 import { debuglog } from "ext:deno_node/internal/util/debuglog.ts";
 import type { DuplexOptions } from "ext:deno_node/_stream.d.ts";
 import type { BufferEncoding } from "ext:deno_node/_global.d.ts";
 import type { Abortable } from "ext:deno_node/_events.d.ts";
 import { channel } from "node:diagnostics_channel";
+import { primordials } from "ext:core/mod.js";
+
+const {
+  ArrayPrototypeIncludes,
+  ArrayPrototypePush,
+  FunctionPrototypeBind,
+  MathMax,
+} = primordials;
 
 let debug = debuglog("net", (fn) => {
   debug = fn;
@@ -120,6 +136,9 @@ const kBytesWritten = Symbol("kBytesWritten");
 const DEFAULT_IPV4_ADDR = "0.0.0.0";
 const DEFAULT_IPV6_ADDR = "::";
 
+let autoSelectFamilyDefault = true;
+let autoSelectFamilyAttemptTimeoutDefault = 250;
+
 type Handle = TCP | Pipe;
 
 interface HandleOptions {
@@ -214,6 +233,8 @@ interface TcpSocketConnectOptions extends ConnectOptions {
   hints?: number;
   family?: number;
   lookup?: LookupFunction;
+  autoSelectFamily?: boolean | undefined;
+  autoSelectFamilyAttemptTimeout?: number | undefined;
 }
 
 interface IpcSocketConnectOptions extends ConnectOptions {
@@ -316,12 +337,6 @@ export function _normalizeArgs(args: unknown[]): NormalizedArgs {
   return arr;
 }
 
-function _isTCPConnectWrap(
-  req: TCPConnectWrap | PipeConnectWrap,
-): req is TCPConnectWrap {
-  return "localAddress" in req && "localPort" in req;
-}
-
 function _afterConnect(
   status: number,
   // deno-lint-ignore no-explicit-any
@@ -372,7 +387,7 @@ function _afterConnect(
     socket.connecting = false;
     let details;
 
-    if (_isTCPConnectWrap(req)) {
+    if (req.localAddress && req.localPort) {
       details = req.localAddress + ":" + req.localPort;
     }
 
@@ -384,7 +399,7 @@ function _afterConnect(
       details,
     );
 
-    if (_isTCPConnectWrap(req)) {
+    if (details) {
       ex.localAddress = req.localAddress;
       ex.localPort = req.localPort;
     }
@@ -393,6 +408,107 @@ function _afterConnect(
   }
 }
 
+function _createConnectionError(req, status) {
+  let details;
+
+  if (req.localAddress && req.localPort) {
+    details = req.localAddress + ":" + req.localPort;
+  }
+
+  const ex = exceptionWithHostPort(
+    status,
+    "connect",
+    req.address,
+    req.port,
+    details,
+  );
+  if (details) {
+    ex.localAddress = req.localAddress;
+    ex.localPort = req.localPort;
+  }
+
+  return ex;
+}
+
+function _afterConnectMultiple(
+  context,
+  current,
+  status,
+  handle,
+  req,
+  readable,
+  writable,
+) {
+  debug(
+    "connect/multiple: connection attempt to %s:%s completed with status %s",
+    req.address,
+    req.port,
+    status,
+  );
+
+  // Make sure another connection is not spawned
+  clearTimeout(context[kTimeout]);
+
+  // One of the connection has completed and correctly dispatched but after timeout, ignore this one
+  if (status === 0 && current !== context.current - 1) {
+    debug(
+      "connect/multiple: ignoring successful but timedout connection to %s:%s",
+      req.address,
+      req.port,
+    );
+    handle.close();
+    return;
+  }
+
+  const self = context.socket;
+
+  // Some error occurred, add to the list of exceptions
+  if (status !== 0) {
+    const ex = _createConnectionError(req, status);
+    ArrayPrototypePush(context.errors, ex);
+
+    self.emit(
+      "connectionAttemptFailed",
+      req.address,
+      req.port,
+      req.addressType,
+      ex,
+    );
+
+    // Try the next address, unless we were aborted
+    if (context.socket.connecting) {
+      _internalConnectMultiple(context, status === UV_ECANCELED);
+    }
+
+    return;
+  }
+
+  _afterConnect(status, self._handle, req, readable, writable);
+}
+
+function _internalConnectMultipleTimeout(context, req, handle) {
+  debug(
+    "connect/multiple: connection to %s:%s timed out",
+    req.address,
+    req.port,
+  );
+  context.socket.emit(
+    "connectionAttemptTimeout",
+    req.address,
+    req.port,
+    req.addressType,
+  );
+
+  req.oncomplete = undefined;
+  ArrayPrototypePush(context.errors, _createConnectionError(req, UV_ETIMEDOUT));
+  handle.close();
+
+  // Try the next address, unless we were aborted
+  if (context.socket.connecting) {
+    _internalConnectMultiple(context);
+  }
+}
+
 function _checkBindError(err: number, port: number, handle: TCP) {
   // EADDRINUSE may not be reported until we call `listen()` or `connect()`.
   // To complicate matters, a failed `bind()` followed by `listen()` or `connect()`
@@ -495,6 +611,131 @@ function _internalConnect(
   }
 }
 
+function _internalConnectMultiple(context, canceled?: boolean) {
+  clearTimeout(context[kTimeout]);
+  const self = context.socket;
+
+  // We were requested to abort. Stop all operations
+  if (self._aborted) {
+    return;
+  }
+
+  // All connections have been tried without success, destroy with error
+  if (canceled || context.current === context.addresses.length) {
+    if (context.errors.length === 0) {
+      self.destroy(new ERR_SOCKET_CONNECTION_TIMEOUT());
+      return;
+    }
+
+    self.destroy(new NodeAggregateError(context.errors));
+    return;
+  }
+
+  assert(self.connecting);
+
+  const current = context.current++;
+
+  if (current > 0) {
+    self[kReinitializeHandle](new TCP(TCPConstants.SOCKET));
+  }
+
+  const { localPort, port, flags } = context;
+  const { address, family: addressType } = context.addresses[current];
+  let localAddress;
+  let err;
+
+  if (localPort) {
+    if (addressType === 4) {
+      localAddress = DEFAULT_IPV4_ADDR;
+      err = self._handle.bind(localAddress, localPort);
+    } else { // addressType === 6
+      localAddress = DEFAULT_IPV6_ADDR;
+      err = self._handle.bind6(localAddress, localPort, flags);
+    }
+
+    debug(
+      "connect/multiple: binding to localAddress: %s and localPort: %d (addressType: %d)",
+      localAddress,
+      localPort,
+      addressType,
+    );
+
+    err = _checkBindError(err, localPort, self._handle);
+    if (err) {
+      ArrayPrototypePush(
+        context.errors,
+        exceptionWithHostPort(err, "bind", localAddress, localPort),
+      );
+      _internalConnectMultiple(context);
+      return;
+    }
+  }
+
+  debug(
+    "connect/multiple: attempting to connect to %s:%d (addressType: %d)",
+    address,
+    port,
+    addressType,
+  );
+  self.emit("connectionAttempt", address, port, addressType);
+
+  const req = new TCPConnectWrap();
+  req.oncomplete = FunctionPrototypeBind(
+    _afterConnectMultiple,
+    undefined,
+    context,
+    current,
+  );
+  req.address = address;
+  req.port = port;
+  req.localAddress = localAddress;
+  req.localPort = localPort;
+  req.addressType = addressType;
+
+  ArrayPrototypePush(
+    self.autoSelectFamilyAttemptedAddresses,
+    `${address}:${port}`,
+  );
+
+  if (addressType === 4) {
+    err = self._handle.connect(req, address, port);
+  } else {
+    err = self._handle.connect6(req, address, port);
+  }
+
+  if (err) {
+    const sockname = self._getsockname();
+    let details;
+
+    if (sockname) {
+      details = sockname.address + ":" + sockname.port;
+    }
+
+    const ex = exceptionWithHostPort(err, "connect", address, port, details);
+    ArrayPrototypePush(context.errors, ex);
+
+    self.emit("connectionAttemptFailed", address, port, addressType, ex);
+    _internalConnectMultiple(context);
+    return;
+  }
+
+  if (current < context.addresses.length - 1) {
+    debug(
+      "connect/multiple: setting the attempt timeout to %d ms",
+      context.timeout,
+    );
+
+    // If the attempt has not returned an error, start the connection timer
+    context[kTimeout] = setTimeout(
+      _internalConnectMultipleTimeout,
+      context.timeout,
+      context,
+      req,
+      self._handle,
+    );
+  }
+}
+
 // Provide a better error message when we call end() as a result
 // of the other side sending a FIN.  The standard "write after end"
 // is overly vague, and makes it seem like the user's code is to blame.
@@ -597,7 +838,7 @@ function _lookupAndConnect(
 ) {
   const { localAddress, localPort } = options;
   const host = options.host || "localhost";
-  let { port } = options;
+  let { port, autoSelectFamilyAttemptTimeout, autoSelectFamily } = options;
 
   if (localAddress && !isIP(localAddress)) {
     throw new ERR_INVALID_IP_ADDRESS(localAddress);
@@ -621,6 +862,22 @@ function _lookupAndConnect(
 
   port |= 0;
 
+  if (autoSelectFamily != null) {
+    validateBoolean(autoSelectFamily, "options.autoSelectFamily");
+  } else {
+    autoSelectFamily = autoSelectFamilyDefault;
+  }
+
+  if (autoSelectFamilyAttemptTimeout !== undefined) {
+    validateInt32(autoSelectFamilyAttemptTimeout);
+
+    if (autoSelectFamilyAttemptTimeout < 10) {
+      autoSelectFamilyAttemptTimeout = 10;
+    }
+  } else {
+    autoSelectFamilyAttemptTimeout = autoSelectFamilyAttemptTimeoutDefault;
+  }
+
   // If host is an IP, skip performing a lookup
   const addressType = isIP(host);
   if (addressType) {
@@ -649,6 +906,7 @@ function _lookupAndConnect(
   const dnsOpts = {
     family: options.family,
     hints: options.hints || 0,
+    all: false,
   };
 
   if (
@@ -665,6 +923,31 @@ function _lookupAndConnect(
   self._host = host;
   const lookup = options.lookup || dnsLookup;
 
+  if (
+    dnsOpts.family !== 4 && dnsOpts.family !== 6 && !localAddress &&
+    autoSelectFamily
+  ) {
+    debug("connect: autodetecting");
+
+    dnsOpts.all = true;
+    defaultTriggerAsyncIdScope(self[asyncIdSymbol], function () {
+      _lookupAndConnectMultiple(
+        self,
+        asyncIdSymbol,
+        lookup,
+        host,
+        options,
+        dnsOpts,
+        port,
+        localAddress,
+        localPort,
+        autoSelectFamilyAttemptTimeout,
+      );
+    });
+
+    return;
+  }
+
   defaultTriggerAsyncIdScope(self[asyncIdSymbol], function () {
     lookup(
       host,
@@ -719,6 +1002,143 @@ function _lookupAndConnect(
   });
 }
 
+function _lookupAndConnectMultiple(
+  self: Socket,
+  asyncIdSymbol: number,
+  // deno-lint-ignore no-explicit-any
+  lookup: any,
+  host: string,
+  options: TcpSocketConnectOptions,
+  dnsopts,
+  port: number,
+  localAddress: string,
+  localPort: number,
+  timeout: number | undefined,
+) {
+  defaultTriggerAsyncIdScope(self[asyncIdSymbol], function emitLookup() {
+    lookup(host, dnsopts, function emitLookup(err, addresses) {
+      // It's possible we were destroyed while looking this up.
+      // XXX it would be great if we could cancel the promise returned by
+      // the look up.
+      if (!self.connecting) {
+        return;
+      } else if (err) {
+        self.emit("lookup", err, undefined, undefined, host);
+
+        // net.createConnection() creates a net.Socket object and immediately
+        // calls net.Socket.connect() on it (that's us). There are no event
+        // listeners registered yet so defer the error event to the next tick.
+        nextTick(_connectErrorNT, self, err);
+        return;
+      }
+
+      // Filter addresses by only keeping the one which are either IPv4 or IPV6.
+      // The first valid address determines which group has preference on the
+      // alternate family sorting which happens later.
+      const validAddresses = [[], []];
+      const validIps = [[], []];
+      let destinations;
+      for (let i = 0, l = addresses.length; i < l; i++) {
+        const address = addresses[i];
+        const { address: ip, family: addressType } = address;
+        self.emit("lookup", err, ip, addressType, host);
+        // It's possible we were destroyed while looking this up.
+        if (!self.connecting) {
+          return;
+        }
+        if (isIP(ip) && (addressType === 4 || addressType === 6)) {
+          destinations ||= addressType === 6 ? { 6: 0, 4: 1 } : { 4: 0, 6: 1 };
+
+          const destination = destinations[addressType];
+
+          // Only try an address once
+          if (!ArrayPrototypeIncludes(validIps[destination], ip)) {
+            ArrayPrototypePush(validAddresses[destination], address);
+            ArrayPrototypePush(validIps[destination], ip);
+          }
+        }
+      }
+
+      // When no AAAA or A records are available, fail on the first one
+      if (!validAddresses[0].length && !validAddresses[1].length) {
+        const { address: firstIp, family: firstAddressType } = addresses[0];
+
+        if (!isIP(firstIp)) {
+          err = new ERR_INVALID_IP_ADDRESS(firstIp);
+          nextTick(_connectErrorNT, self, err);
+        } else if (firstAddressType !== 4 && firstAddressType !== 6) {
+          err = new ERR_INVALID_ADDRESS_FAMILY(
+            firstAddressType,
+            options.host,
+            options.port,
+          );
+          nextTick(_connectErrorNT, self, err);
+        }
+
+        return;
+      }
+
+      // Sort addresses alternating families
+      const toAttempt = [];
+      for (
+        let i = 0,
+          l = MathMax(validAddresses[0].length, validAddresses[1].length);
+        i < l;
+        i++
+      ) {
+        if (i in validAddresses[0]) {
+          ArrayPrototypePush(toAttempt, validAddresses[0][i]);
+        }
+        if (i in validAddresses[1]) {
+          ArrayPrototypePush(toAttempt, validAddresses[1][i]);
+        }
+      }
+
+      if (toAttempt.length === 1) {
+        debug(
+          "connect/multiple: only one address found, switching back to single connection",
+        );
+        const { address: ip, family: addressType } = toAttempt[0];
+
+        self._unrefTimer();
+        defaultTriggerAsyncIdScope(
+          self[asyncIdSymbol],
+          _internalConnect,
+          self,
+          ip,
+          port,
+          addressType,
+          localAddress,
+          localPort,
+        );
+
+        return;
+      }
+
+      self.autoSelectFamilyAttemptedAddresses = [];
+      debug("connect/multiple: will try the following addresses", toAttempt);
+
+      const context = {
+        socket: self,
+        addresses: toAttempt,
+        current: 0,
+        port,
+        localPort,
+        timeout,
+        [kTimeout]: null,
+        errors: [],
+      };
+
+      self._unrefTimer();
+      defaultTriggerAsyncIdScope(
+        self[asyncIdSymbol],
+        _internalConnectMultiple,
+        context,
+      );
+    });
+  });
+}
+
 function _afterShutdown(this: ShutdownWrap<TCP>) {
   // deno-lint-ignore no-explicit-any
   const self: any = this.handle[ownerSymbol];
@@ -777,6 +1197,7 @@ export class Socket extends Duplex {
   _host: string | null = null;
   // deno-lint-ignore no-explicit-any
   _parent: any = null;
+  autoSelectFamilyAttemptedAddresses: AddressInfo[] | undefined = undefined;
 
   constructor(options: SocketOptions | number) {
     if (typeof options === "number") {
@@ -1546,6 +1967,16 @@ export class Socket extends Duplex {
   set _handle(v: Handle | null) {
     this[kHandle] = v;
   }
+
+  // deno-lint-ignore no-explicit-any
+  [kReinitializeHandle](handle: any) {
+    this._handle?.close();
+
+    this._handle = handle;
+    this._handle[ownerSymbol] = this;
+
+    _initSocketHandle(this);
+  }
 }
 
 export const Stream = Socket;
@@ -1593,6 +2024,33 @@ export function connect(...args: unknown[]) {
 
 export const createConnection = connect;
 
+/** https://docs.deno.com/api/node/net/#namespace_getdefaultautoselectfamily */
+export function getDefaultAutoSelectFamily() {
+  return autoSelectFamilyDefault;
+}
+
+/** https://docs.deno.com/api/node/net/#namespace_setdefaultautoselectfamily */
+export function setDefaultAutoSelectFamily(value: boolean) {
+  validateBoolean(value, "value");
+  autoSelectFamilyDefault = value;
+}
+
+/** https://docs.deno.com/api/node/net/#namespace_getdefaultautoselectfamilyattempttimeout */
+export function getDefaultAutoSelectFamilyAttemptTimeout() {
+  return autoSelectFamilyAttemptTimeoutDefault;
+}
+
+/** https://docs.deno.com/api/node/net/#namespace_setdefaultautoselectfamilyattempttimeout */
+export function setDefaultAutoSelectFamilyAttemptTimeout(value: number) {
+  validateInt32(value, "value", 1);
+
+  if (value < 10) {
+    value = 10;
+  }
+
+  autoSelectFamilyAttemptTimeoutDefault = value;
+}
+
 export interface ListenOptions extends Abortable {
   fd?: number;
   port?: number | undefined;
@@ -2478,15 +2936,19 @@ export { BlockList, isIP, isIPv4, isIPv6, SocketAddress };
 export default {
   _createServerHandle,
   _normalizeArgs,
-  isIP,
-  isIPv4,
-  isIPv6,
   BlockList,
-  SocketAddress,
   connect,
   createConnection,
   createServer,
+  getDefaultAutoSelectFamily,
+  getDefaultAutoSelectFamilyAttemptTimeout,
+  isIP,
+  isIPv4,
+  isIPv6,
   Server,
+  setDefaultAutoSelectFamily,
+  setDefaultAutoSelectFamilyAttemptTimeout,
   Socket,
+  SocketAddress,
   Stream,
 };
diff --git a/ext/node/polyfills/os.ts b/ext/node/polyfills/os.ts
index e47e8679ec..edc89ed2c3 100644
--- a/ext/node/polyfills/os.ts
+++ b/ext/node/polyfills/os.ts
@@ -28,16 +28,17 @@ import {
   op_homedir,
   op_node_os_get_priority,
   op_node_os_set_priority,
-  op_node_os_username,
+  op_node_os_user_info,
 } from "ext:core/ops";
 
 import { validateIntegerRange } from "ext:deno_node/_utils.ts";
 import process from "node:process";
 import { isWindows } from "ext:deno_node/_util/os.ts";
-import { ERR_OS_NO_HOMEDIR } from "ext:deno_node/internal/errors.ts";
 import { os } from "ext:deno_node/internal_binding/constants.ts";
 import { osUptime } from "ext:runtime/30_os.js";
 import { Buffer } from "ext:deno_node/internal/buffer.mjs";
+import { primordials } from "ext:core/mod.js";
+const { StringPrototypeEndsWith, StringPrototypeSlice } = primordials;
 
 export const constants = os;
 
@@ -136,6 +137,8 @@ export function arch(): string {
 (uptime as any)[Symbol.toPrimitive] = (): number => uptime();
 // deno-lint-ignore no-explicit-any
 (machine as any)[Symbol.toPrimitive] = (): string => machine();
+// deno-lint-ignore no-explicit-any
+(tmpdir as any)[Symbol.toPrimitive] = (): string | null => tmpdir();
 
 export function cpus(): CPUCoreInfo[] {
   return op_cpus();
@@ -268,26 +271,27 @@ export function setPriority(pid: number, priority?: number) {
 export function tmpdir(): string | null {
   /* This follows the node js implementation, but has a few
      differences:
-     * On windows, if none of the environment variables are defined,
-       we return null.
-     * On unix we use a plain Deno.env.get, instead of safeGetenv,
+     * We use a plain Deno.env.get, instead of safeGetenv,
        which special cases setuid binaries.
-     * Node removes a single trailing / or \, we remove all.
   */
   if (isWindows) {
-    const temp = Deno.env.get("TEMP") || Deno.env.get("TMP");
-    if (temp) {
-      return temp.replace(/(?<!:)[/\\]*$/, "");
+    let temp = Deno.env.get("TEMP") || Deno.env.get("TMP") ||
+      (Deno.env.get("SystemRoot") || Deno.env.get("windir")) + "\\temp";
+    if (
+      temp.length > 1 && StringPrototypeEndsWith(temp, "\\") &&
+      !StringPrototypeEndsWith(temp, ":\\")
+    ) {
+      temp = StringPrototypeSlice(temp, 0, -1);
     }
-    const base = Deno.env.get("SYSTEMROOT") || Deno.env.get("WINDIR");
-    if (base) {
-      return base + "\\temp";
-    }
-    return null;
+
+    return temp;
   } else { // !isWindows
-    const temp = Deno.env.get("TMPDIR") || Deno.env.get("TMP") ||
+    let temp = Deno.env.get("TMPDIR") || Deno.env.get("TMP") ||
       Deno.env.get("TEMP") || "/tmp";
-    return temp.replace(/(?<!^)\/*$/, "");
+    if (temp.length > 1 && StringPrototypeEndsWith(temp, "/")) {
+      temp = StringPrototypeSlice(temp, 0, -1);
+    }
+    return temp;
   }
 }
 
@@ -320,7 +324,6 @@ export function uptime(): number {
   return osUptime();
 }
 
-/** Not yet implemented */
 export function userInfo(
   options: UserInfoOptions = { encoding: "utf-8" },
 ): UserInfo {
@@ -331,20 +334,10 @@ export function userInfo(
     uid = -1;
     gid = -1;
   }
-
-  // TODO(@crowlKats): figure out how to do this correctly:
-  //  The value of homedir returned by os.userInfo() is provided by the operating system.
-  //  This differs from the result of os.homedir(), which queries environment
-  //  variables for the home directory before falling back to the operating system response.
-  let _homedir = homedir();
-  if (!_homedir) {
-    throw new ERR_OS_NO_HOMEDIR();
-  }
-  let shell = isWindows ? null : (Deno.env.get("SHELL") || null);
-  let username = op_node_os_username();
+  let { username, homedir, shell } = op_node_os_user_info(uid);
 
   if (options?.encoding === "buffer") {
-    _homedir = _homedir ? Buffer.from(_homedir) : _homedir;
+    homedir = homedir ? Buffer.from(homedir) : homedir;
     shell = shell ? Buffer.from(shell) : shell;
     username = Buffer.from(username);
   }
@@ -352,7 +345,7 @@ export function userInfo(
   return {
     uid,
     gid,
-    homedir: _homedir,
+    homedir,
     shell,
     username,
   };
diff --git a/ext/node/polyfills/process.ts b/ext/node/polyfills/process.ts
index 3dc6ce61aa..647376d5cf 100644
--- a/ext/node/polyfills/process.ts
+++ b/ext/node/polyfills/process.ts
@@ -15,7 +15,7 @@ import {
 
 import { warnNotImplemented } from "ext:deno_node/_utils.ts";
 import { EventEmitter } from "node:events";
-import Module from "node:module";
+import Module, { getBuiltinModule } from "node:module";
 import { report } from "ext:deno_node/internal/process/report.ts";
 import { validateString } from "ext:deno_node/internal/validators.mjs";
 import {
@@ -38,7 +38,15 @@ import {
   versions,
 } from "ext:deno_node/_process/process.ts";
 import { _exiting } from "ext:deno_node/_process/exiting.ts";
-export { _nextTick as nextTick, chdir, cwd, env, version, versions };
+export {
+  _nextTick as nextTick,
+  chdir,
+  cwd,
+  env,
+  getBuiltinModule,
+  version,
+  versions,
+};
 import {
   createWritableStdioStream,
   initStdin,
@@ -520,9 +528,7 @@ Process.prototype.on = function (
     } else if (
       event !== "SIGBREAK" && event !== "SIGINT" && Deno.build.os === "windows"
     ) {
-      // Ignores all signals except SIGBREAK and SIGINT on windows.
-      // deno-lint-ignore no-console
-      console.warn(`Ignoring signal "${event}" on Windows`);
+      // TODO(#26331): Ignores all signals except SIGBREAK and SIGINT on windows.
     } else {
       EventEmitter.prototype.on.call(this, event, listener);
       Deno.addSignalListener(event as Deno.Signal, listener);
@@ -730,6 +736,8 @@ Process.prototype.getegid = getegid;
 /** This method is removed on Windows */
 Process.prototype.geteuid = geteuid;
 
+Process.prototype.getBuiltinModule = getBuiltinModule;
+
 // TODO(kt3k): Implement this when we added -e option to node compat mode
 Process.prototype._eval = undefined;
 
@@ -911,7 +919,7 @@ Object.defineProperty(argv, "1", {
     if (Deno.mainModule?.startsWith("file:")) {
       return pathFromURL(new URL(Deno.mainModule));
     } else {
-      return join(Deno.cwd(), "$deno$node.js");
+      return join(Deno.cwd(), "$deno$node.mjs");
     }
   },
 });
diff --git a/ext/node/polyfills/util.ts b/ext/node/polyfills/util.ts
index 586fae17e9..d82b288b03 100644
--- a/ext/node/polyfills/util.ts
+++ b/ext/node/polyfills/util.ts
@@ -39,6 +39,7 @@ import {
   formatWithOptions,
   inspect,
   stripVTControlCharacters,
+  styleText,
 } from "ext:deno_node/internal/util/inspect.mjs";
 import { codes } from "ext:deno_node/internal/error_codes.ts";
 import types from "node:util/types";
@@ -63,6 +64,7 @@ export {
   parseArgs,
   promisify,
   stripVTControlCharacters,
+  styleText,
   types,
 };
 
@@ -354,4 +356,5 @@ export default {
   debuglog,
   debug: debuglog,
   isDeepStrictEqual,
+  styleText,
 };
diff --git a/ext/node/polyfills/v8.ts b/ext/node/polyfills/v8.ts
index 5849f3ccc9..9df199865e 100644
--- a/ext/node/polyfills/v8.ts
+++ b/ext/node/polyfills/v8.ts
@@ -313,20 +313,6 @@ export class DefaultDeserializer extends Deserializer {
     );
   }
 }
-export const promiseHooks = {
-  onInit() {
-    notImplemented("v8.promiseHooks.onInit");
-  },
-  onSettled() {
-    notImplemented("v8.promiseHooks.onSetttled");
-  },
-  onBefore() {
-    notImplemented("v8.promiseHooks.onBefore");
-  },
-  createHook() {
-    notImplemented("v8.promiseHooks.createHook");
-  },
-};
 export default {
   cachedDataVersionTag,
   getHeapCodeStatistics,
@@ -343,5 +329,4 @@ export default {
   Deserializer,
   DefaultSerializer,
   DefaultDeserializer,
-  promiseHooks,
 };
diff --git a/ext/node/polyfills/vm.js b/ext/node/polyfills/vm.js
index 183ddad2f4..b64c847c58 100644
--- a/ext/node/polyfills/vm.js
+++ b/ext/node/polyfills/vm.js
@@ -182,6 +182,7 @@ function getContextOptions(options) {
 
 let defaultContextNameIndex = 1;
 export function createContext(
+  // deno-lint-ignore prefer-primordials
   contextObject = {},
   options = { __proto__: null },
 ) {
diff --git a/ext/node/polyfills/worker_threads.ts b/ext/node/polyfills/worker_threads.ts
index 5ff4446f73..d4b75fb30c 100644
--- a/ext/node/polyfills/worker_threads.ts
+++ b/ext/node/polyfills/worker_threads.ts
@@ -302,8 +302,8 @@ class NodeWorker extends EventEmitter {
     if (this.#status !== "TERMINATED") {
       this.#status = "TERMINATED";
       op_host_terminate_worker(this.#id);
+      this.emit("exit", 0);
     }
-    this.emit("exit", 0);
     return PromiseResolve(0);
   }
 
@@ -422,7 +422,11 @@ internals.__initWorkerThreads = (
 
     parentPort.once = function (this: ParentPort, name, listener) {
       // deno-lint-ignore no-explicit-any
-      const _listener = (ev: any) => listener(ev.data);
+      const _listener = (ev: any) => {
+        const message = ev.data;
+        patchMessagePortIfFound(message);
+        return listener(message);
+      };
       listeners.set(listener, _listener);
       this.addEventListener(name, _listener);
       return this;
@@ -494,7 +498,9 @@ export function receiveMessageOnPort(port: MessagePort): object | undefined {
   port[MessagePortReceiveMessageOnPortSymbol] = true;
   const data = op_message_port_recv_message_sync(port[MessagePortIdSymbol]);
   if (data === null) return undefined;
-  return { message: deserializeJsMessageData(data)[0] };
+  const message = deserializeJsMessageData(data)[0];
+  patchMessagePortIfFound(message);
+  return { message };
 }
 
 class NodeMessageChannel {
diff --git a/ext/node/polyfills/zlib.ts b/ext/node/polyfills/zlib.ts
index 3fe5f8bbd9..6e5d02b5be 100644
--- a/ext/node/polyfills/zlib.ts
+++ b/ext/node/polyfills/zlib.ts
@@ -40,6 +40,58 @@ import {
   createBrotliCompress,
   createBrotliDecompress,
 } from "ext:deno_node/_brotli.js";
+import { ERR_INVALID_ARG_TYPE } from "ext:deno_node/internal/errors.ts";
+import { validateUint32 } from "ext:deno_node/internal/validators.mjs";
+import { op_zlib_crc32 } from "ext:core/ops";
+import { core, primordials } from "ext:core/mod.js";
+import { TextEncoder } from "ext:deno_web/08_text_encoding.js";
+const {
+  Uint8Array,
+  TypedArrayPrototypeGetBuffer,
+  TypedArrayPrototypeGetByteLength,
+  TypedArrayPrototypeGetByteOffset,
+  DataViewPrototypeGetBuffer,
+  DataViewPrototypeGetByteLength,
+  DataViewPrototypeGetByteOffset,
+} = primordials;
+const { isTypedArray, isDataView } = core;
+
+const enc = new TextEncoder();
+const toU8 = (input) => {
+  if (typeof input === "string") {
+    return enc.encode(input);
+  }
+
+  if (isTypedArray(input)) {
+    return new Uint8Array(
+      TypedArrayPrototypeGetBuffer(input),
+      TypedArrayPrototypeGetByteOffset(input),
+      TypedArrayPrototypeGetByteLength(input),
+    );
+  } else if (isDataView(input)) {
+    return new Uint8Array(
+      DataViewPrototypeGetBuffer(input),
+      DataViewPrototypeGetByteOffset(input),
+      DataViewPrototypeGetByteLength(input),
+    );
+  }
+
+  return input;
+};
+
+export function crc32(data, value = 0) {
+  if (typeof data !== "string" && !isArrayBufferView(data)) {
+    throw new ERR_INVALID_ARG_TYPE("data", [
+      "Buffer",
+      "TypedArray",
+      "DataView",
+      "string",
+    ], data);
+  }
+  validateUint32(value, "value");
+
+  return op_zlib_crc32(toU8(data), value);
+}
 
 export class Options {
   constructor() {
@@ -87,6 +139,7 @@ export default {
   BrotliOptions,
   codes,
   constants,
+  crc32,
   createBrotliCompress,
   createBrotliDecompress,
   createDeflate,
diff --git a/ext/node_resolver/package_json.rs b/ext/node_resolver/package_json.rs
deleted file mode 100644
index de750f1d7e..0000000000
--- a/ext/node_resolver/package_json.rs
+++ /dev/null
@@ -1,53 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-use deno_package_json::PackageJson;
-use deno_package_json::PackageJsonRc;
-use std::cell::RefCell;
-use std::collections::HashMap;
-use std::io::ErrorKind;
-use std::path::Path;
-use std::path::PathBuf;
-
-use crate::errors::PackageJsonLoadError;
-
-// use a thread local cache so that workers have their own distinct cache
-thread_local! {
-  static CACHE: RefCell<HashMap<PathBuf, PackageJsonRc>> = RefCell::new(HashMap::new());
-}
-
-pub struct PackageJsonThreadLocalCache;
-
-impl PackageJsonThreadLocalCache {
-  pub fn clear() {
-    CACHE.with(|cache| cache.borrow_mut().clear());
-  }
-}
-
-impl deno_package_json::PackageJsonCache for PackageJsonThreadLocalCache {
-  fn get(&self, path: &Path) -> Option<PackageJsonRc> {
-    CACHE.with(|cache| cache.borrow().get(path).cloned())
-  }
-
-  fn set(&self, path: PathBuf, package_json: PackageJsonRc) {
-    CACHE.with(|cache| cache.borrow_mut().insert(path, package_json));
-  }
-}
-
-/// Helper to load a package.json file using the thread local cache
-/// in node_resolver.
-pub fn load_pkg_json(
-  fs: &dyn deno_package_json::fs::DenoPkgJsonFs,
-  path: &Path,
-) -> Result<Option<PackageJsonRc>, PackageJsonLoadError> {
-  let result =
-    PackageJson::load_from_path(path, fs, Some(&PackageJsonThreadLocalCache));
-  match result {
-    Ok(pkg_json) => Ok(Some(pkg_json)),
-    Err(deno_package_json::PackageJsonLoadError::Io { source, .. })
-      if source.kind() == ErrorKind::NotFound =>
-    {
-      Ok(None)
-    }
-    Err(err) => Err(PackageJsonLoadError(err)),
-  }
-}
diff --git a/ext/node_resolver/path.rs b/ext/node_resolver/path.rs
deleted file mode 100644
index ece270cd91..0000000000
--- a/ext/node_resolver/path.rs
+++ /dev/null
@@ -1,179 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-use std::path::Component;
-use std::path::Path;
-use std::path::PathBuf;
-
-use url::Url;
-
-/// Extension to path_clean::PathClean
-pub trait PathClean<T> {
-  fn clean(&self) -> T;
-}
-
-impl PathClean<PathBuf> for PathBuf {
-  fn clean(&self) -> PathBuf {
-    fn is_clean_path(path: &Path) -> bool {
-      let path = path.to_string_lossy();
-      let mut current_index = 0;
-      while let Some(index) = path[current_index..].find("\\.") {
-        let trailing_index = index + current_index + 2;
-        let mut trailing_chars = path[trailing_index..].chars();
-        match trailing_chars.next() {
-          Some('.') => match trailing_chars.next() {
-            Some('/') | Some('\\') | None => {
-              return false;
-            }
-            _ => {}
-          },
-          Some('/') | Some('\\') => {
-            return false;
-          }
-          _ => {}
-        }
-        current_index = trailing_index;
-      }
-      true
-    }
-
-    let path = path_clean::PathClean::clean(self);
-    if cfg!(windows) && !is_clean_path(&path) {
-      // temporary workaround because path_clean::PathClean::clean is
-      // not good enough on windows
-      let mut components = Vec::new();
-
-      for component in path.components() {
-        match component {
-          Component::CurDir => {
-            // skip
-          }
-          Component::ParentDir => {
-            let maybe_last_component = components.pop();
-            if !matches!(maybe_last_component, Some(Component::Normal(_))) {
-              panic!("Error normalizing: {}", path.display());
-            }
-          }
-          Component::Normal(_) | Component::RootDir | Component::Prefix(_) => {
-            components.push(component);
-          }
-        }
-      }
-      components.into_iter().collect::<PathBuf>()
-    } else {
-      path
-    }
-  }
-}
-
-pub(crate) fn to_file_specifier(path: &Path) -> Url {
-  match Url::from_file_path(path) {
-    Ok(url) => url,
-    Err(_) => panic!("Invalid path: {}", path.display()),
-  }
-}
-
-// todo(dsherret): we have the below code also in deno_core and it
-// would be good to somehow re-use it in both places (we don't want
-// to create a dependency on deno_core here)
-
-#[cfg(not(windows))]
-#[inline]
-pub fn strip_unc_prefix(path: PathBuf) -> PathBuf {
-  path
-}
-
-/// Strips the unc prefix (ex. \\?\) from Windows paths.
-#[cfg(windows)]
-pub fn strip_unc_prefix(path: PathBuf) -> PathBuf {
-  use std::path::Component;
-  use std::path::Prefix;
-
-  let mut components = path.components();
-  match components.next() {
-    Some(Component::Prefix(prefix)) => {
-      match prefix.kind() {
-        // \\?\device
-        Prefix::Verbatim(device) => {
-          let mut path = PathBuf::new();
-          path.push(format!(r"\\{}\", device.to_string_lossy()));
-          path.extend(components.filter(|c| !matches!(c, Component::RootDir)));
-          path
-        }
-        // \\?\c:\path
-        Prefix::VerbatimDisk(_) => {
-          let mut path = PathBuf::new();
-          path.push(prefix.as_os_str().to_string_lossy().replace(r"\\?\", ""));
-          path.extend(components);
-          path
-        }
-        // \\?\UNC\hostname\share_name\path
-        Prefix::VerbatimUNC(hostname, share_name) => {
-          let mut path = PathBuf::new();
-          path.push(format!(
-            r"\\{}\{}\",
-            hostname.to_string_lossy(),
-            share_name.to_string_lossy()
-          ));
-          path.extend(components.filter(|c| !matches!(c, Component::RootDir)));
-          path
-        }
-        _ => path,
-      }
-    }
-    _ => path,
-  }
-}
-
-#[cfg(test)]
-mod test {
-  #[cfg(windows)]
-  #[test]
-  fn test_path_clean() {
-    use super::*;
-
-    run_test("C:\\test\\./file.txt", "C:\\test\\file.txt");
-    run_test("C:\\test\\../other/file.txt", "C:\\other\\file.txt");
-    run_test("C:\\test\\../other\\file.txt", "C:\\other\\file.txt");
-
-    fn run_test(input: &str, expected: &str) {
-      assert_eq!(PathBuf::from(input).clean(), PathBuf::from(expected));
-    }
-  }
-
-  #[cfg(windows)]
-  #[test]
-  fn test_strip_unc_prefix() {
-    use std::path::PathBuf;
-
-    run_test(r"C:\", r"C:\");
-    run_test(r"C:\test\file.txt", r"C:\test\file.txt");
-
-    run_test(r"\\?\C:\", r"C:\");
-    run_test(r"\\?\C:\test\file.txt", r"C:\test\file.txt");
-
-    run_test(r"\\.\C:\", r"\\.\C:\");
-    run_test(r"\\.\C:\Test\file.txt", r"\\.\C:\Test\file.txt");
-
-    run_test(r"\\?\UNC\localhost\", r"\\localhost");
-    run_test(r"\\?\UNC\localhost\c$\", r"\\localhost\c$");
-    run_test(
-      r"\\?\UNC\localhost\c$\Windows\file.txt",
-      r"\\localhost\c$\Windows\file.txt",
-    );
-    run_test(r"\\?\UNC\wsl$\deno.json", r"\\wsl$\deno.json");
-
-    run_test(r"\\?\server1", r"\\server1");
-    run_test(r"\\?\server1\e$\", r"\\server1\e$\");
-    run_test(
-      r"\\?\server1\e$\test\file.txt",
-      r"\\server1\e$\test\file.txt",
-    );
-
-    fn run_test(input: &str, expected: &str) {
-      assert_eq!(
-        super::strip_unc_prefix(PathBuf::from(input)),
-        PathBuf::from(expected)
-      );
-    }
-  }
-}
diff --git a/ext/tls/Cargo.toml b/ext/tls/Cargo.toml
index 08a9802df5..943fc8413e 100644
--- a/ext/tls/Cargo.toml
+++ b/ext/tls/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_tls"
-version = "0.155.0"
+version = "0.164.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -21,5 +21,6 @@ rustls-pemfile.workspace = true
 rustls-tokio-stream.workspace = true
 rustls-webpki.workspace = true
 serde.workspace = true
+thiserror.workspace = true
 tokio.workspace = true
 webpki-roots.workspace = true
diff --git a/ext/tls/lib.rs b/ext/tls/lib.rs
index c4d548ccf2..883d2995e4 100644
--- a/ext/tls/lib.rs
+++ b/ext/tls/lib.rs
@@ -9,17 +9,12 @@ pub use rustls_tokio_stream::*;
 pub use webpki;
 pub use webpki_roots;
 
-use deno_core::anyhow::anyhow;
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
-
 use rustls::client::danger::HandshakeSignatureValid;
 use rustls::client::danger::ServerCertVerified;
 use rustls::client::danger::ServerCertVerifier;
 use rustls::client::WebPkiServerVerifier;
 use rustls::ClientConfig;
 use rustls::DigitallySignedStruct;
-use rustls::Error;
 use rustls::RootCertStore;
 use rustls_pemfile::certs;
 use rustls_pemfile::ec_private_keys;
@@ -35,12 +30,30 @@ use std::sync::Arc;
 mod tls_key;
 pub use tls_key::*;
 
+#[derive(Debug, thiserror::Error)]
+pub enum TlsError {
+  #[error(transparent)]
+  Rustls(#[from] rustls::Error),
+  #[error("Unable to add pem file to certificate store: {0}")]
+  UnableAddPemFileToCert(std::io::Error),
+  #[error("Unable to decode certificate")]
+  CertInvalid,
+  #[error("No certificates found in certificate data")]
+  CertsNotFound,
+  #[error("No keys found in key data")]
+  KeysNotFound,
+  #[error("Unable to decode key")]
+  KeyDecode,
+}
+
 /// Lazily resolves the root cert store.
 ///
 /// This was done because the root cert store is not needed in all cases
 /// and takes a bit of time to initialize.
 pub trait RootCertStoreProvider: Send + Sync {
-  fn get_or_try_init(&self) -> Result<&RootCertStore, AnyError>;
+  fn get_or_try_init(
+    &self,
+  ) -> Result<&RootCertStore, deno_core::error::AnyError>;
 }
 
 // This extension has no runtime apis, it only exports some shared native functions.
@@ -77,7 +90,7 @@ impl ServerCertVerifier for NoCertificateVerification {
     server_name: &rustls::pki_types::ServerName<'_>,
     ocsp_response: &[u8],
     now: rustls::pki_types::UnixTime,
-  ) -> Result<ServerCertVerified, Error> {
+  ) -> Result<ServerCertVerified, rustls::Error> {
     if self.ic_allowlist.is_empty() {
       return Ok(ServerCertVerified::assertion());
     }
@@ -89,7 +102,9 @@ impl ServerCertVerifier for NoCertificateVerification {
       _ => {
         // NOTE(bartlomieju): `ServerName` is a non-exhaustive enum
         // so we have this catch all errors here.
-        return Err(Error::General("Unknown `ServerName` variant".to_string()));
+        return Err(rustls::Error::General(
+          "Unknown `ServerName` variant".to_string(),
+        ));
       }
     };
     if self.ic_allowlist.contains(&dns_name_or_ip_address) {
@@ -110,7 +125,7 @@ impl ServerCertVerifier for NoCertificateVerification {
     message: &[u8],
     cert: &rustls::pki_types::CertificateDer,
     dss: &DigitallySignedStruct,
-  ) -> Result<HandshakeSignatureValid, Error> {
+  ) -> Result<HandshakeSignatureValid, rustls::Error> {
     if self.ic_allowlist.is_empty() {
       return Ok(HandshakeSignatureValid::assertion());
     }
@@ -126,7 +141,7 @@ impl ServerCertVerifier for NoCertificateVerification {
     message: &[u8],
     cert: &rustls::pki_types::CertificateDer,
     dss: &DigitallySignedStruct,
-  ) -> Result<HandshakeSignatureValid, Error> {
+  ) -> Result<HandshakeSignatureValid, rustls::Error> {
     if self.ic_allowlist.is_empty() {
       return Ok(HandshakeSignatureValid::assertion());
     }
@@ -178,7 +193,7 @@ pub fn create_client_config(
   unsafely_ignore_certificate_errors: Option<Vec<String>>,
   maybe_cert_chain_and_key: TlsKeys,
   socket_use: SocketUse,
-) -> Result<ClientConfig, AnyError> {
+) -> Result<ClientConfig, TlsError> {
   if let Some(ic_allowlist) = unsafely_ignore_certificate_errors {
     let client_config = ClientConfig::builder()
       .dangerous()
@@ -214,10 +229,7 @@ pub fn create_client_config(
           root_cert_store.add(cert)?;
         }
         Err(e) => {
-          return Err(anyhow!(
-            "Unable to add pem file to certificate store: {}",
-            e
-          ));
+          return Err(TlsError::UnableAddPemFileToCert(e));
         }
       }
     }
@@ -255,74 +267,61 @@ fn add_alpn(client: &mut ClientConfig, socket_use: SocketUse) {
 
 pub fn load_certs(
   reader: &mut dyn BufRead,
-) -> Result<Vec<CertificateDer<'static>>, AnyError> {
+) -> Result<Vec<CertificateDer<'static>>, TlsError> {
   let certs: Result<Vec<_>, _> = certs(reader).collect();
 
-  let certs = certs
-    .map_err(|_| custom_error("InvalidData", "Unable to decode certificate"))?;
+  let certs = certs.map_err(|_| TlsError::CertInvalid)?;
 
   if certs.is_empty() {
-    return Err(cert_not_found_err());
+    return Err(TlsError::CertsNotFound);
   }
 
   Ok(certs)
 }
 
-fn key_decode_err() -> AnyError {
-  custom_error("InvalidData", "Unable to decode key")
-}
-
-fn key_not_found_err() -> AnyError {
-  custom_error("InvalidData", "No keys found in key data")
-}
-
-fn cert_not_found_err() -> AnyError {
-  custom_error("InvalidData", "No certificates found in certificate data")
-}
-
 /// Starts with -----BEGIN RSA PRIVATE KEY-----
 fn load_rsa_keys(
   mut bytes: &[u8],
-) -> Result<Vec<PrivateKeyDer<'static>>, AnyError> {
+) -> Result<Vec<PrivateKeyDer<'static>>, TlsError> {
   let keys: Result<Vec<_>, _> = rsa_private_keys(&mut bytes).collect();
-  let keys = keys.map_err(|_| key_decode_err())?;
+  let keys = keys.map_err(|_| TlsError::KeyDecode)?;
   Ok(keys.into_iter().map(PrivateKeyDer::Pkcs1).collect())
 }
 
 /// Starts with -----BEGIN EC PRIVATE KEY-----
 fn load_ec_keys(
   mut bytes: &[u8],
-) -> Result<Vec<PrivateKeyDer<'static>>, AnyError> {
+) -> Result<Vec<PrivateKeyDer<'static>>, TlsError> {
   let keys: Result<Vec<_>, std::io::Error> =
     ec_private_keys(&mut bytes).collect();
-  let keys2 = keys.map_err(|_| key_decode_err())?;
+  let keys2 = keys.map_err(|_| TlsError::KeyDecode)?;
   Ok(keys2.into_iter().map(PrivateKeyDer::Sec1).collect())
 }
 
 /// Starts with -----BEGIN PRIVATE KEY-----
 fn load_pkcs8_keys(
   mut bytes: &[u8],
-) -> Result<Vec<PrivateKeyDer<'static>>, AnyError> {
+) -> Result<Vec<PrivateKeyDer<'static>>, TlsError> {
   let keys: Result<Vec<_>, std::io::Error> =
     pkcs8_private_keys(&mut bytes).collect();
-  let keys2 = keys.map_err(|_| key_decode_err())?;
+  let keys2 = keys.map_err(|_| TlsError::KeyDecode)?;
   Ok(keys2.into_iter().map(PrivateKeyDer::Pkcs8).collect())
 }
 
 fn filter_invalid_encoding_err(
-  to_be_filtered: Result<HandshakeSignatureValid, Error>,
-) -> Result<HandshakeSignatureValid, Error> {
+  to_be_filtered: Result<HandshakeSignatureValid, rustls::Error>,
+) -> Result<HandshakeSignatureValid, rustls::Error> {
   match to_be_filtered {
-    Err(Error::InvalidCertificate(rustls::CertificateError::BadEncoding)) => {
-      Ok(HandshakeSignatureValid::assertion())
-    }
+    Err(rustls::Error::InvalidCertificate(
+      rustls::CertificateError::BadEncoding,
+    )) => Ok(HandshakeSignatureValid::assertion()),
     res => res,
   }
 }
 
 pub fn load_private_keys(
   bytes: &[u8],
-) -> Result<Vec<PrivateKeyDer<'static>>, AnyError> {
+) -> Result<Vec<PrivateKeyDer<'static>>, TlsError> {
   let mut keys = load_rsa_keys(bytes)?;
 
   if keys.is_empty() {
@@ -334,7 +333,7 @@ pub fn load_private_keys(
   }
 
   if keys.is_empty() {
-    return Err(key_not_found_err());
+    return Err(TlsError::KeysNotFound);
   }
 
   Ok(keys)
diff --git a/ext/tls/tls_key.rs b/ext/tls/tls_key.rs
index 66fac86f87..b7baa604b9 100644
--- a/ext/tls/tls_key.rs
+++ b/ext/tls/tls_key.rs
@@ -11,8 +11,6 @@
 //! key lookup can handle closing one end of the pair, in which case they will just
 //! attempt to clean up the associated resources.
 
-use deno_core::anyhow::anyhow;
-use deno_core::error::AnyError;
 use deno_core::futures::future::poll_fn;
 use deno_core::futures::future::Either;
 use deno_core::futures::FutureExt;
@@ -33,7 +31,19 @@ use tokio::sync::oneshot;
 use webpki::types::CertificateDer;
 use webpki::types::PrivateKeyDer;
 
-type ErrorType = Rc<AnyError>;
+#[derive(Debug, thiserror::Error)]
+pub enum TlsKeyError {
+  #[error(transparent)]
+  Rustls(#[from] rustls::Error),
+  #[error("Failed: {0}")]
+  Failed(ErrorType),
+  #[error(transparent)]
+  JoinError(#[from] tokio::task::JoinError),
+  #[error(transparent)]
+  RecvError(#[from] tokio::sync::broadcast::error::RecvError),
+}
+
+type ErrorType = Arc<Box<str>>;
 
 /// A TLS certificate/private key pair.
 /// see https://docs.rs/rustls-pki-types/latest/rustls_pki_types/#cloning-private-keys
@@ -114,7 +124,7 @@ impl TlsKeyResolver {
     &self,
     sni: String,
     alpn: Vec<Vec<u8>>,
-  ) -> Result<Arc<ServerConfig>, AnyError> {
+  ) -> Result<Arc<ServerConfig>, TlsKeyError> {
     let key = self.resolve(sni).await?;
 
     let mut tls_config = ServerConfig::builder()
@@ -183,7 +193,7 @@ impl TlsKeyResolver {
   pub fn resolve(
     &self,
     sni: String,
-  ) -> impl Future<Output = Result<TlsKey, AnyError>> {
+  ) -> impl Future<Output = Result<TlsKey, TlsKeyError>> {
     let mut cache = self.inner.cache.borrow_mut();
     let mut recv = match cache.get(&sni) {
       None => {
@@ -194,7 +204,7 @@ impl TlsKeyResolver {
       }
       Some(TlsKeyState::Resolving(recv)) => recv.resubscribe(),
       Some(TlsKeyState::Resolved(res)) => {
-        return Either::Left(ready(res.clone().map_err(|_| anyhow!("Failed"))));
+        return Either::Left(ready(res.clone().map_err(TlsKeyError::Failed)));
       }
     };
     drop(cache);
@@ -212,7 +222,7 @@ impl TlsKeyResolver {
           // Someone beat us to it
         }
       }
-      res.map_err(|_| anyhow!("Failed"))
+      res.map_err(TlsKeyError::Failed)
     });
     Either::Right(async move { handle.await? })
   }
@@ -247,13 +257,13 @@ impl TlsKeyLookup {
   }
 
   /// Resolve a previously polled item.
-  pub fn resolve(&self, sni: String, res: Result<TlsKey, AnyError>) {
+  pub fn resolve(&self, sni: String, res: Result<TlsKey, String>) {
     _ = self
       .pending
       .borrow_mut()
       .remove(&sni)
       .unwrap()
-      .send(res.map_err(Rc::new));
+      .send(res.map_err(|e| Arc::new(e.into_boxed_str())));
   }
 }
 
diff --git a/ext/url/00_url.js b/ext/url/00_url.js
index 577caba902..ec875da768 100644
--- a/ext/url/00_url.js
+++ b/ext/url/00_url.js
@@ -139,7 +139,7 @@ class URLSearchParams {
           throw new TypeError(
             `${prefix}: Item ${
               i + 0
-            } in the parameter list does have length 2 exactly.`,
+            } in the parameter list does have length 2 exactly`,
           );
         }
         return [pair[0], pair[1]];
diff --git a/ext/url/01_urlpattern.js b/ext/url/01_urlpattern.js
index 58a6d6bce0..6e27563089 100644
--- a/ext/url/01_urlpattern.js
+++ b/ext/url/01_urlpattern.js
@@ -31,6 +31,7 @@ import * as webidl from "ext:deno_webidl/00_webidl.js";
 import { createFilteredInspectProxy } from "ext:deno_console/01_console.js";
 
 const _components = Symbol("components");
+const urlPatternSettings = { groupStringFallback: false };
 
 /**
  * @typedef Components
@@ -349,7 +350,11 @@ class URLPattern {
           const groups = res.groups;
           for (let i = 0; i < groupList.length; ++i) {
             // TODO(lucacasonato): this is vulnerable to override mistake
-            groups[groupList[i]] = match[i + 1] ?? ""; // TODO(@crowlKats): remove fallback for 2.0
+            if (urlPatternSettings.groupStringFallback) {
+              groups[groupList[i]] = match[i + 1] ?? "";
+            } else {
+              groups[groupList[i]] = match[i + 1];
+            }
           }
           break;
         }
@@ -422,4 +427,4 @@ webidl.converters.URLPatternOptions = webidl
     },
   ]);
 
-export { URLPattern };
+export { URLPattern, urlPatternSettings };
diff --git a/ext/url/Cargo.toml b/ext/url/Cargo.toml
index 7f86e14456..557a4669e6 100644
--- a/ext/url/Cargo.toml
+++ b/ext/url/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_url"
-version = "0.168.0"
+version = "0.177.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -15,6 +15,7 @@ path = "lib.rs"
 
 [dependencies]
 deno_core.workspace = true
+thiserror.workspace = true
 urlpattern = "0.3.0"
 
 [dev-dependencies]
diff --git a/ext/url/lib.rs b/ext/url/lib.rs
index 6869d656b5..f8946532ae 100644
--- a/ext/url/lib.rs
+++ b/ext/url/lib.rs
@@ -15,6 +15,8 @@ use std::path::PathBuf;
 use crate::urlpattern::op_urlpattern_parse;
 use crate::urlpattern::op_urlpattern_process_match_input;
 
+pub use urlpattern::UrlPatternError;
+
 deno_core::extension!(
   deno_url,
   deps = [deno_webidl],
diff --git a/ext/url/urlpattern.rs b/ext/url/urlpattern.rs
index b6d9a13828..7d4e8ee71b 100644
--- a/ext/url/urlpattern.rs
+++ b/ext/url/urlpattern.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 
 use urlpattern::quirks;
@@ -9,21 +7,23 @@ use urlpattern::quirks::MatchInput;
 use urlpattern::quirks::StringOrInit;
 use urlpattern::quirks::UrlPattern;
 
+#[derive(Debug, thiserror::Error)]
+#[error(transparent)]
+pub struct UrlPatternError(urlpattern::Error);
+
 #[op2]
 #[serde]
 pub fn op_urlpattern_parse(
   #[serde] input: StringOrInit,
   #[string] base_url: Option<String>,
   #[serde] options: urlpattern::UrlPatternOptions,
-) -> Result<UrlPattern, AnyError> {
-  let init = urlpattern::quirks::process_construct_pattern_input(
-    input,
-    base_url.as_deref(),
-  )
-  .map_err(|e| type_error(e.to_string()))?;
+) -> Result<UrlPattern, UrlPatternError> {
+  let init =
+    quirks::process_construct_pattern_input(input, base_url.as_deref())
+      .map_err(UrlPatternError)?;
 
-  let pattern = urlpattern::quirks::parse_pattern(init, options)
-    .map_err(|e| type_error(e.to_string()))?;
+  let pattern =
+    quirks::parse_pattern(init, options).map_err(UrlPatternError)?;
 
   Ok(pattern)
 }
@@ -33,14 +33,14 @@ pub fn op_urlpattern_parse(
 pub fn op_urlpattern_process_match_input(
   #[serde] input: StringOrInit,
   #[string] base_url: Option<String>,
-) -> Result<Option<(MatchInput, quirks::Inputs)>, AnyError> {
-  let res = urlpattern::quirks::process_match_input(input, base_url.as_deref())
-    .map_err(|e| type_error(e.to_string()))?;
+) -> Result<Option<(MatchInput, quirks::Inputs)>, UrlPatternError> {
+  let res = quirks::process_match_input(input, base_url.as_deref())
+    .map_err(UrlPatternError)?;
 
   let (input, inputs) = match res {
     Some((input, inputs)) => (input, inputs),
     None => return Ok(None),
   };
 
-  Ok(urlpattern::quirks::parse_match_input(input).map(|input| (input, inputs)))
+  Ok(quirks::parse_match_input(input).map(|input| (input, inputs)))
 }
diff --git a/ext/web/02_timers.js b/ext/web/02_timers.js
index 89acaca42b..6058febd59 100644
--- a/ext/web/02_timers.js
+++ b/ext/web/02_timers.js
@@ -1,12 +1,9 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 import { core, primordials } from "ext:core/mod.js";
-import { op_defer, op_now } from "ext:core/ops";
+import { op_defer } from "ext:core/ops";
 const {
-  Uint8Array,
-  Uint32Array,
   PromisePrototypeThen,
-  TypedArrayPrototypeGetBuffer,
   TypeError,
   indirectEval,
   ReflectApply,
@@ -18,13 +15,6 @@ const {
 
 import * as webidl from "ext:deno_webidl/00_webidl.js";
 
-const hrU8 = new Uint8Array(8);
-const hr = new Uint32Array(TypedArrayPrototypeGetBuffer(hrU8));
-function opNow() {
-  op_now(hrU8);
-  return (hr[0] * 1000 + hr[1] / 1e6);
-}
-
 // ---------------------------------------------------------------------------
 
 function checkThis(thisArg) {
@@ -151,7 +141,6 @@ export {
   clearInterval,
   clearTimeout,
   defer,
-  opNow,
   refTimer,
   setImmediate,
   setInterval,
diff --git a/ext/web/13_message_port.js b/ext/web/13_message_port.js
index 04697d6aa8..cf72c43e6f 100644
--- a/ext/web/13_message_port.js
+++ b/ext/web/13_message_port.js
@@ -22,6 +22,7 @@ const {
   Symbol,
   SymbolFor,
   SymbolIterator,
+  PromiseResolve,
   SafeArrayIterator,
   TypeError,
 } = primordials;
@@ -41,7 +42,10 @@ import {
 import { isDetachedBuffer } from "./06_streams.js";
 import { DOMException } from "./01_dom_exception.js";
 
-let messageEventListenerCount = 0;
+// counter of how many message ports are actively refed
+// either due to the existence of "message" event listeners or
+// explicit calls to ref/unref (in the case of node message ports)
+let refedMessagePortsCount = 0;
 
 class MessageChannel {
   /** @type {MessagePort} */
@@ -93,6 +97,7 @@ const MessagePortReceiveMessageOnPortSymbol = Symbol(
 );
 const _enabled = Symbol("enabled");
 const _refed = Symbol("refed");
+const _messageEventListenerCount = Symbol("messageEventListenerCount");
 const nodeWorkerThreadCloseCb = Symbol("nodeWorkerThreadCloseCb");
 const nodeWorkerThreadCloseCbInvoked = Symbol("nodeWorkerThreadCloseCbInvoked");
 export const refMessagePort = Symbol("refMessagePort");
@@ -109,6 +114,9 @@ function createMessagePort(id) {
   port[core.hostObjectBrand] = core.hostObjectBrand;
   setEventTargetData(port);
   port[_id] = id;
+  port[_enabled] = false;
+  port[_messageEventListenerCount] = 0;
+  port[_refed] = false;
   return port;
 }
 
@@ -122,12 +130,18 @@ function nodeWorkerThreadMaybeInvokeCloseCb(port) {
   }
 }
 
+const _isRefed = Symbol("isRefed");
+const _dataPromise = Symbol("dataPromise");
+
 class MessagePort extends EventTarget {
   /** @type {number | null} */
   [_id] = null;
   /** @type {boolean} */
   [_enabled] = false;
   [_refed] = false;
+  /** @type {Promise<any> | undefined} */
+  [_dataPromise] = undefined;
+  [_messageEventListenerCount] = 0;
 
   constructor() {
     super();
@@ -193,24 +207,21 @@ class MessagePort extends EventTarget {
       this[_enabled] = true;
       while (true) {
         if (this[_id] === null) break;
-        // Exit if no message event listeners are present in Node compat mode.
-        if (
-          typeof this[nodeWorkerThreadCloseCb] == "function" &&
-          messageEventListenerCount === 0
-        ) break;
         let data;
         try {
-          data = await op_message_port_recv_message(
+          this[_dataPromise] = op_message_port_recv_message(
             this[_id],
           );
+          if (
+            typeof this[nodeWorkerThreadCloseCb] === "function" &&
+            !this[_refed]
+          ) {
+            core.unrefOpPromise(this[_dataPromise]);
+          }
+          data = await this[_dataPromise];
+          this[_dataPromise] = undefined;
         } catch (err) {
           if (ObjectPrototypeIsPrototypeOf(InterruptedPrototype, err)) {
-            // If we were interrupted, check if the interruption is coming
-            // from `receiveMessageOnPort` API from Node compat, if so, continue.
-            if (this[MessagePortReceiveMessageOnPortSymbol]) {
-              this[MessagePortReceiveMessageOnPortSymbol] = false;
-              continue;
-            }
             break;
           }
           nodeWorkerThreadMaybeInvokeCloseCb(this);
@@ -246,12 +257,26 @@ class MessagePort extends EventTarget {
   }
 
   [refMessagePort](ref) {
-    if (ref && !this[_refed]) {
-      this[_refed] = true;
-      messageEventListenerCount++;
-    } else if (!ref && this[_refed]) {
-      this[_refed] = false;
-      messageEventListenerCount = 0;
+    if (ref) {
+      if (!this[_refed]) {
+        refedMessagePortsCount++;
+        if (
+          this[_dataPromise]
+        ) {
+          core.refOpPromise(this[_dataPromise]);
+        }
+        this[_refed] = true;
+      }
+    } else if (!ref) {
+      if (this[_refed]) {
+        refedMessagePortsCount--;
+        if (
+          this[_dataPromise]
+        ) {
+          core.unrefOpPromise(this[_dataPromise]);
+        }
+        this[_refed] = false;
+      }
     }
   }
 
@@ -266,15 +291,20 @@ class MessagePort extends EventTarget {
 
   removeEventListener(...args) {
     if (args[0] == "message") {
-      messageEventListenerCount--;
+      if (--this[_messageEventListenerCount] === 0 && this[_refed]) {
+        refedMessagePortsCount--;
+        this[_refed] = false;
+      }
     }
     super.removeEventListener(...new SafeArrayIterator(args));
   }
 
   addEventListener(...args) {
     if (args[0] == "message") {
-      messageEventListenerCount++;
-      if (!this[_refed]) this[_refed] = true;
+      if (++this[_messageEventListenerCount] === 1 && !this[_refed]) {
+        refedMessagePortsCount++;
+        this[_refed] = true;
+      }
     }
     super.addEventListener(...new SafeArrayIterator(args));
   }
@@ -295,7 +325,17 @@ class MessagePort extends EventTarget {
 }
 
 defineEventHandler(MessagePort.prototype, "message", function (self) {
-  self.start();
+  if (self[nodeWorkerThreadCloseCb]) {
+    (async () => {
+      // delay `start()` until he end of this event loop turn, to give `receiveMessageOnPort`
+      // a chance to receive a message first. this is primarily to resolve an issue with
+      // a pattern used in `npm:piscina` that results in an indefinite hang
+      await PromiseResolve();
+      self.start();
+    })();
+  } else {
+    self.start();
+  }
 });
 defineEventHandler(MessagePort.prototype, "messageerror");
 
@@ -463,12 +503,12 @@ function structuredClone(value, options) {
 export {
   deserializeJsMessageData,
   MessageChannel,
-  messageEventListenerCount,
   MessagePort,
   MessagePortIdSymbol,
   MessagePortPrototype,
   MessagePortReceiveMessageOnPortSymbol,
   nodeWorkerThreadCloseCb,
+  refedMessagePortsCount,
   serializeJsMessageData,
   structuredClone,
 };
diff --git a/ext/web/15_performance.js b/ext/web/15_performance.js
index ea55572781..9e0e310a57 100644
--- a/ext/web/15_performance.js
+++ b/ext/web/15_performance.js
@@ -1,6 +1,7 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 import { primordials } from "ext:core/mod.js";
+import { op_now, op_time_origin } from "ext:core/ops";
 const {
   ArrayPrototypeFilter,
   ArrayPrototypePush,
@@ -10,19 +11,34 @@ const {
   Symbol,
   SymbolFor,
   TypeError,
+  TypedArrayPrototypeGetBuffer,
+  Uint8Array,
+  Uint32Array,
 } = primordials;
 
 import * as webidl from "ext:deno_webidl/00_webidl.js";
 import { structuredClone } from "./02_structured_clone.js";
 import { createFilteredInspectProxy } from "ext:deno_console/01_console.js";
 import { EventTarget } from "./02_event.js";
-import { opNow } from "./02_timers.js";
 import { DOMException } from "./01_dom_exception.js";
 
 const illegalConstructorKey = Symbol("illegalConstructorKey");
 let performanceEntries = [];
 let timeOrigin;
 
+const hrU8 = new Uint8Array(8);
+const hr = new Uint32Array(TypedArrayPrototypeGetBuffer(hrU8));
+
+function setTimeOrigin() {
+  op_time_origin(hrU8);
+  timeOrigin = hr[0] * 1000 + hr[1] / 1e6;
+}
+
+function now() {
+  op_now(hrU8);
+  return hr[0] * 1000 + hr[1] / 1e6;
+}
+
 webidl.converters["PerformanceMarkOptions"] = webidl
   .createDictionaryConverter(
     "PerformanceMarkOptions",
@@ -90,10 +106,6 @@ webidl.converters["DOMString or PerformanceMeasureOptions"] = (
   return webidl.converters.DOMString(V, prefix, context, opts);
 };
 
-function setTimeOrigin(origin) {
-  timeOrigin = origin;
-}
-
 function findMostRecent(
   name,
   type,
@@ -135,8 +147,6 @@ function filterByNameType(
   );
 }
 
-const now = opNow;
-
 const _name = Symbol("[[name]]");
 const _entryType = Symbol("[[entryType]]");
 const _startTime = Symbol("[[startTime]]");
diff --git a/ext/web/Cargo.toml b/ext/web/Cargo.toml
index 7fd12632d7..db28d0e578 100644
--- a/ext/web/Cargo.toml
+++ b/ext/web/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_web"
-version = "0.199.0"
+version = "0.208.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -23,6 +23,7 @@ encoding_rs.workspace = true
 flate2 = { workspace = true, features = ["default"] }
 futures.workspace = true
 serde = "1.0.149"
+thiserror.workspace = true
 tokio.workspace = true
 uuid = { workspace = true, features = ["serde"] }
 
diff --git a/ext/web/blob.rs b/ext/web/blob.rs
index 392f36acb8..bc64a0f27e 100644
--- a/ext/web/blob.rs
+++ b/ext/web/blob.rs
@@ -7,8 +7,6 @@ use std::rc::Rc;
 use std::sync::Arc;
 
 use async_trait::async_trait;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::parking_lot::Mutex;
 use deno_core::url::Url;
@@ -19,6 +17,18 @@ use serde::Deserialize;
 use serde::Serialize;
 use uuid::Uuid;
 
+#[derive(Debug, thiserror::Error)]
+pub enum BlobError {
+  #[error("Blob part not found")]
+  BlobPartNotFound,
+  #[error("start + len can not be larger than blob part size")]
+  SizeLargerThanBlobPart,
+  #[error("Blob URLs are not supported in this context")]
+  BlobURLsNotSupported,
+  #[error(transparent)]
+  Url(#[from] deno_core::url::ParseError),
+}
+
 use crate::Location;
 
 pub type PartMap = HashMap<Uuid, Arc<dyn BlobPart + Send + Sync>>;
@@ -96,18 +106,18 @@ pub struct Blob {
 
 impl Blob {
   // TODO(lucacsonato): this should be a stream!
-  pub async fn read_all(&self) -> Result<Vec<u8>, AnyError> {
+  pub async fn read_all(&self) -> Vec<u8> {
     let size = self.size();
     let mut bytes = Vec::with_capacity(size);
 
     for part in &self.parts {
-      let chunk = part.read().await?;
+      let chunk = part.read().await;
       bytes.extend_from_slice(chunk);
     }
 
     assert_eq!(bytes.len(), size);
 
-    Ok(bytes)
+    bytes
   }
 
   fn size(&self) -> usize {
@@ -122,7 +132,7 @@ impl Blob {
 #[async_trait]
 pub trait BlobPart: Debug {
   // TODO(lucacsonato): this should be a stream!
-  async fn read(&self) -> Result<&[u8], AnyError>;
+  async fn read(&self) -> &[u8];
   fn size(&self) -> usize;
 }
 
@@ -137,8 +147,8 @@ impl From<Vec<u8>> for InMemoryBlobPart {
 
 #[async_trait]
 impl BlobPart for InMemoryBlobPart {
-  async fn read(&self) -> Result<&[u8], AnyError> {
-    Ok(&self.0)
+  async fn read(&self) -> &[u8] {
+    &self.0
   }
 
   fn size(&self) -> usize {
@@ -155,9 +165,9 @@ pub struct SlicedBlobPart {
 
 #[async_trait]
 impl BlobPart for SlicedBlobPart {
-  async fn read(&self) -> Result<&[u8], AnyError> {
-    let original = self.part.read().await?;
-    Ok(&original[self.start..self.start + self.len])
+  async fn read(&self) -> &[u8] {
+    let original = self.part.read().await;
+    &original[self.start..self.start + self.len]
   }
 
   fn size(&self) -> usize {
@@ -189,19 +199,17 @@ pub fn op_blob_slice_part(
   state: &mut OpState,
   #[serde] id: Uuid,
   #[serde] options: SliceOptions,
-) -> Result<Uuid, AnyError> {
+) -> Result<Uuid, BlobError> {
   let blob_store = state.borrow::<Arc<BlobStore>>();
   let part = blob_store
     .get_part(&id)
-    .ok_or_else(|| type_error("Blob part not found"))?;
+    .ok_or(BlobError::BlobPartNotFound)?;
 
   let SliceOptions { start, len } = options;
 
   let size = part.size();
   if start + len > size {
-    return Err(type_error(
-      "start + len can not be larger than blob part size",
-    ));
+    return Err(BlobError::SizeLargerThanBlobPart);
   }
 
   let sliced_part = SlicedBlobPart { part, start, len };
@@ -215,14 +223,14 @@ pub fn op_blob_slice_part(
 pub async fn op_blob_read_part(
   state: Rc<RefCell<OpState>>,
   #[serde] id: Uuid,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, BlobError> {
   let part = {
     let state = state.borrow();
     let blob_store = state.borrow::<Arc<BlobStore>>();
     blob_store.get_part(&id)
   }
-  .ok_or_else(|| type_error("Blob part not found"))?;
-  let buf = part.read().await?;
+  .ok_or(BlobError::BlobPartNotFound)?;
+  let buf = part.read().await;
   Ok(ToJsBuffer::from(buf.to_vec()))
 }
 
@@ -238,13 +246,13 @@ pub fn op_blob_create_object_url(
   state: &mut OpState,
   #[string] media_type: String,
   #[serde] part_ids: Vec<Uuid>,
-) -> Result<String, AnyError> {
+) -> Result<String, BlobError> {
   let mut parts = Vec::with_capacity(part_ids.len());
   let blob_store = state.borrow::<Arc<BlobStore>>();
   for part_id in part_ids {
     let part = blob_store
       .get_part(&part_id)
-      .ok_or_else(|| type_error("Blob part not found"))?;
+      .ok_or(BlobError::BlobPartNotFound)?;
     parts.push(part);
   }
 
@@ -263,7 +271,7 @@ pub fn op_blob_create_object_url(
 pub fn op_blob_revoke_object_url(
   state: &mut OpState,
   #[string] url: &str,
-) -> Result<(), AnyError> {
+) -> Result<(), BlobError> {
   let url = Url::parse(url)?;
   let blob_store = state.borrow::<Arc<BlobStore>>();
   blob_store.remove_object_url(&url);
@@ -287,15 +295,15 @@ pub struct ReturnBlobPart {
 pub fn op_blob_from_object_url(
   state: &mut OpState,
   #[string] url: String,
-) -> Result<Option<ReturnBlob>, AnyError> {
+) -> Result<Option<ReturnBlob>, BlobError> {
   let url = Url::parse(&url)?;
   if url.scheme() != "blob" {
     return Ok(None);
   }
 
-  let blob_store = state.try_borrow::<Arc<BlobStore>>().ok_or_else(|| {
-    type_error("Blob URLs are not supported in this context.")
-  })?;
+  let blob_store = state
+    .try_borrow::<Arc<BlobStore>>()
+    .ok_or(BlobError::BlobURLsNotSupported)?;
   if let Some(blob) = blob_store.get_object_url(url) {
     let parts = blob
       .parts
diff --git a/ext/web/compression.rs b/ext/web/compression.rs
index b9ae12ef17..6967009915 100644
--- a/ext/web/compression.rs
+++ b/ext/web/compression.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use flate2::write::DeflateDecoder;
 use flate2::write::DeflateEncoder;
@@ -13,6 +11,18 @@ use flate2::Compression;
 use std::cell::RefCell;
 use std::io::Write;
 
+#[derive(Debug, thiserror::Error)]
+pub enum CompressionError {
+  #[error("Unsupported format")]
+  UnsupportedFormat,
+  #[error("resource is closed")]
+  ResourceClosed,
+  #[error(transparent)]
+  IoTypeError(std::io::Error),
+  #[error(transparent)]
+  Io(std::io::Error),
+}
+
 #[derive(Debug)]
 struct CompressionResource(RefCell<Option<Inner>>);
 
@@ -34,7 +44,7 @@ enum Inner {
 pub fn op_compression_new(
   #[string] format: &str,
   is_decoder: bool,
-) -> Result<CompressionResource, AnyError> {
+) -> Result<CompressionResource, CompressionError> {
   let w = Vec::new();
   let inner = match (format, is_decoder) {
     ("deflate", true) => Inner::DeflateDecoder(ZlibDecoder::new(w)),
@@ -49,7 +59,7 @@ pub fn op_compression_new(
     ("gzip", false) => {
       Inner::GzEncoder(GzEncoder::new(w, Compression::default()))
     }
-    _ => return Err(type_error("Unsupported format")),
+    _ => return Err(CompressionError::UnsupportedFormat),
   };
   Ok(CompressionResource(RefCell::new(Some(inner))))
 }
@@ -59,40 +69,38 @@ pub fn op_compression_new(
 pub fn op_compression_write(
   #[cppgc] resource: &CompressionResource,
   #[anybuffer] input: &[u8],
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, CompressionError> {
   let mut inner = resource.0.borrow_mut();
-  let inner = inner
-    .as_mut()
-    .ok_or_else(|| type_error("resource is closed"))?;
+  let inner = inner.as_mut().ok_or(CompressionError::ResourceClosed)?;
   let out: Vec<u8> = match &mut *inner {
     Inner::DeflateDecoder(d) => {
-      d.write_all(input).map_err(|e| type_error(e.to_string()))?;
-      d.flush()?;
+      d.write_all(input).map_err(CompressionError::IoTypeError)?;
+      d.flush().map_err(CompressionError::Io)?;
       d.get_mut().drain(..)
     }
     Inner::DeflateEncoder(d) => {
-      d.write_all(input).map_err(|e| type_error(e.to_string()))?;
-      d.flush()?;
+      d.write_all(input).map_err(CompressionError::IoTypeError)?;
+      d.flush().map_err(CompressionError::Io)?;
       d.get_mut().drain(..)
     }
     Inner::DeflateRawDecoder(d) => {
-      d.write_all(input).map_err(|e| type_error(e.to_string()))?;
-      d.flush()?;
+      d.write_all(input).map_err(CompressionError::IoTypeError)?;
+      d.flush().map_err(CompressionError::Io)?;
       d.get_mut().drain(..)
     }
     Inner::DeflateRawEncoder(d) => {
-      d.write_all(input).map_err(|e| type_error(e.to_string()))?;
-      d.flush()?;
+      d.write_all(input).map_err(CompressionError::IoTypeError)?;
+      d.flush().map_err(CompressionError::Io)?;
       d.get_mut().drain(..)
     }
     Inner::GzDecoder(d) => {
-      d.write_all(input).map_err(|e| type_error(e.to_string()))?;
-      d.flush()?;
+      d.write_all(input).map_err(CompressionError::IoTypeError)?;
+      d.flush().map_err(CompressionError::Io)?;
       d.get_mut().drain(..)
     }
     Inner::GzEncoder(d) => {
-      d.write_all(input).map_err(|e| type_error(e.to_string()))?;
-      d.flush()?;
+      d.write_all(input).map_err(CompressionError::IoTypeError)?;
+      d.flush().map_err(CompressionError::Io)?;
       d.get_mut().drain(..)
     }
   }
@@ -105,27 +113,27 @@ pub fn op_compression_write(
 pub fn op_compression_finish(
   #[cppgc] resource: &CompressionResource,
   report_errors: bool,
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, CompressionError> {
   let inner = resource
     .0
     .borrow_mut()
     .take()
-    .ok_or_else(|| type_error("resource is closed"))?;
+    .ok_or(CompressionError::ResourceClosed)?;
   let out = match inner {
     Inner::DeflateDecoder(d) => {
-      d.finish().map_err(|e| type_error(e.to_string()))
+      d.finish().map_err(CompressionError::IoTypeError)
     }
     Inner::DeflateEncoder(d) => {
-      d.finish().map_err(|e| type_error(e.to_string()))
+      d.finish().map_err(CompressionError::IoTypeError)
     }
     Inner::DeflateRawDecoder(d) => {
-      d.finish().map_err(|e| type_error(e.to_string()))
+      d.finish().map_err(CompressionError::IoTypeError)
     }
     Inner::DeflateRawEncoder(d) => {
-      d.finish().map_err(|e| type_error(e.to_string()))
+      d.finish().map_err(CompressionError::IoTypeError)
     }
-    Inner::GzDecoder(d) => d.finish().map_err(|e| type_error(e.to_string())),
-    Inner::GzEncoder(d) => d.finish().map_err(|e| type_error(e.to_string())),
+    Inner::GzDecoder(d) => d.finish().map_err(CompressionError::IoTypeError),
+    Inner::GzEncoder(d) => d.finish().map_err(CompressionError::IoTypeError),
   };
   match out {
     Err(err) => {
diff --git a/ext/web/lib.rs b/ext/web/lib.rs
index 3977379a5d..af0fc2c276 100644
--- a/ext/web/lib.rs
+++ b/ext/web/lib.rs
@@ -6,9 +6,6 @@ mod message_port;
 mod stream_resource;
 mod timers;
 
-use deno_core::error::range_error;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::url::Url;
 use deno_core::v8;
@@ -22,10 +19,14 @@ use encoding_rs::DecoderResult;
 use encoding_rs::Encoding;
 use std::borrow::Cow;
 use std::cell::RefCell;
-use std::fmt;
 use std::path::PathBuf;
 use std::sync::Arc;
 
+pub use blob::BlobError;
+pub use compression::CompressionError;
+pub use message_port::MessagePortError;
+pub use stream_resource::StreamResourceError;
+
 use crate::blob::op_blob_create_object_url;
 use crate::blob::op_blob_create_part;
 use crate::blob::op_blob_from_object_url;
@@ -51,7 +52,8 @@ pub use crate::message_port::Transferable;
 
 use crate::timers::op_defer;
 use crate::timers::op_now;
-use crate::timers::StartTime;
+use crate::timers::op_time_origin;
+pub use crate::timers::StartTime;
 pub use crate::timers::TimersPermission;
 
 deno_core::extension!(deno_web,
@@ -83,6 +85,7 @@ deno_core::extension!(deno_web,
     compression::op_compression_write,
     compression::op_compression_finish,
     op_now<P>,
+    op_time_origin<P>,
     op_defer,
     stream_resource::op_readable_stream_resource_allocate,
     stream_resource::op_readable_stream_resource_allocate_sized,
@@ -122,13 +125,31 @@ deno_core::extension!(deno_web,
     if let Some(location) = options.maybe_location {
       state.put(Location(location));
     }
-    state.put(StartTime::now());
+    state.put(StartTime::default());
   }
 );
 
+#[derive(Debug, thiserror::Error)]
+pub enum WebError {
+  #[error("Failed to decode base64")]
+  Base64Decode,
+  #[error("The encoding label provided ('{0}') is invalid.")]
+  InvalidEncodingLabel(String),
+  #[error("buffer exceeds maximum length")]
+  BufferTooLong,
+  #[error("Value too large to decode")]
+  ValueTooLarge,
+  #[error("Provided buffer too small")]
+  BufferTooSmall,
+  #[error("The encoded data is not valid")]
+  DataInvalid,
+  #[error(transparent)]
+  DataError(#[from] v8::DataError),
+}
+
 #[op2]
 #[serde]
-fn op_base64_decode(#[string] input: String) -> Result<ToJsBuffer, AnyError> {
+fn op_base64_decode(#[string] input: String) -> Result<ToJsBuffer, WebError> {
   let mut s = input.into_bytes();
   let decoded_len = forgiving_base64_decode_inplace(&mut s)?;
   s.truncate(decoded_len);
@@ -137,7 +158,7 @@ fn op_base64_decode(#[string] input: String) -> Result<ToJsBuffer, AnyError> {
 
 #[op2]
 #[serde]
-fn op_base64_atob(#[serde] mut s: ByteString) -> Result<ByteString, AnyError> {
+fn op_base64_atob(#[serde] mut s: ByteString) -> Result<ByteString, WebError> {
   let decoded_len = forgiving_base64_decode_inplace(&mut s)?;
   s.truncate(decoded_len);
   Ok(s)
@@ -147,11 +168,9 @@ fn op_base64_atob(#[serde] mut s: ByteString) -> Result<ByteString, AnyError> {
 #[inline]
 fn forgiving_base64_decode_inplace(
   input: &mut [u8],
-) -> Result<usize, AnyError> {
-  let error =
-    || DomExceptionInvalidCharacterError::new("Failed to decode base64");
-  let decoded =
-    base64_simd::forgiving_decode_inplace(input).map_err(|_| error())?;
+) -> Result<usize, WebError> {
+  let decoded = base64_simd::forgiving_decode_inplace(input)
+    .map_err(|_| WebError::Base64Decode)?;
   Ok(decoded.len())
 }
 
@@ -177,13 +196,9 @@ fn forgiving_base64_encode(s: &[u8]) -> String {
 #[string]
 fn op_encoding_normalize_label(
   #[string] label: String,
-) -> Result<String, AnyError> {
+) -> Result<String, WebError> {
   let encoding = Encoding::for_label_no_replacement(label.as_bytes())
-    .ok_or_else(|| {
-      range_error(format!(
-        "The encoding label provided ('{label}') is invalid."
-      ))
-    })?;
+    .ok_or(WebError::InvalidEncodingLabel(label))?;
   Ok(encoding.name().to_lowercase())
 }
 
@@ -192,7 +207,7 @@ fn op_encoding_decode_utf8<'a>(
   scope: &mut v8::HandleScope<'a>,
   #[anybuffer] zero_copy: &[u8],
   ignore_bom: bool,
-) -> Result<v8::Local<'a, v8::String>, AnyError> {
+) -> Result<v8::Local<'a, v8::String>, WebError> {
   let buf = &zero_copy;
 
   let buf = if !ignore_bom
@@ -216,7 +231,7 @@ fn op_encoding_decode_utf8<'a>(
   // - https://github.com/v8/v8/blob/d68fb4733e39525f9ff0a9222107c02c28096e2a/include/v8.h#L3277-L3278
   match v8::String::new_from_utf8(scope, buf, v8::NewStringType::Normal) {
     Some(text) => Ok(text),
-    None => Err(type_error("buffer exceeds maximum length")),
+    None => Err(WebError::BufferTooLong),
   }
 }
 
@@ -227,12 +242,9 @@ fn op_encoding_decode_single(
   #[string] label: String,
   fatal: bool,
   ignore_bom: bool,
-) -> Result<U16String, AnyError> {
-  let encoding = Encoding::for_label(label.as_bytes()).ok_or_else(|| {
-    range_error(format!(
-      "The encoding label provided ('{label}') is invalid."
-    ))
-  })?;
+) -> Result<U16String, WebError> {
+  let encoding = Encoding::for_label(label.as_bytes())
+    .ok_or(WebError::InvalidEncodingLabel(label))?;
 
   let mut decoder = if ignore_bom {
     encoding.new_decoder_without_bom_handling()
@@ -242,7 +254,7 @@ fn op_encoding_decode_single(
 
   let max_buffer_length = decoder
     .max_utf16_buffer_length(data.len())
-    .ok_or_else(|| range_error("Value too large to decode."))?;
+    .ok_or(WebError::ValueTooLarge)?;
 
   let mut output = vec![0; max_buffer_length];
 
@@ -254,12 +266,8 @@ fn op_encoding_decode_single(
         output.truncate(written);
         Ok(output.into())
       }
-      DecoderResult::OutputFull => {
-        Err(range_error("Provided buffer too small."))
-      }
-      DecoderResult::Malformed(_, _) => {
-        Err(type_error("The encoded data is not valid."))
-      }
+      DecoderResult::OutputFull => Err(WebError::BufferTooSmall),
+      DecoderResult::Malformed(_, _) => Err(WebError::DataInvalid),
     }
   } else {
     let (result, _, written, _) =
@@ -269,7 +277,7 @@ fn op_encoding_decode_single(
         output.truncate(written);
         Ok(output.into())
       }
-      CoderResult::OutputFull => Err(range_error("Provided buffer too small.")),
+      CoderResult::OutputFull => Err(WebError::BufferTooSmall),
     }
   }
 }
@@ -280,12 +288,9 @@ fn op_encoding_new_decoder(
   #[string] label: &str,
   fatal: bool,
   ignore_bom: bool,
-) -> Result<TextDecoderResource, AnyError> {
-  let encoding = Encoding::for_label(label.as_bytes()).ok_or_else(|| {
-    range_error(format!(
-      "The encoding label provided ('{label}') is invalid."
-    ))
-  })?;
+) -> Result<TextDecoderResource, WebError> {
+  let encoding = Encoding::for_label(label.as_bytes())
+    .ok_or_else(|| WebError::InvalidEncodingLabel(label.to_string()))?;
 
   let decoder = if ignore_bom {
     encoding.new_decoder_without_bom_handling()
@@ -305,13 +310,13 @@ fn op_encoding_decode(
   #[anybuffer] data: &[u8],
   #[cppgc] resource: &TextDecoderResource,
   stream: bool,
-) -> Result<U16String, AnyError> {
+) -> Result<U16String, WebError> {
   let mut decoder = resource.decoder.borrow_mut();
   let fatal = resource.fatal;
 
   let max_buffer_length = decoder
     .max_utf16_buffer_length(data.len())
-    .ok_or_else(|| range_error("Value too large to decode."))?;
+    .ok_or(WebError::ValueTooLarge)?;
 
   let mut output = vec![0; max_buffer_length];
 
@@ -323,12 +328,8 @@ fn op_encoding_decode(
         output.truncate(written);
         Ok(output.into())
       }
-      DecoderResult::OutputFull => {
-        Err(range_error("Provided buffer too small."))
-      }
-      DecoderResult::Malformed(_, _) => {
-        Err(type_error("The encoded data is not valid."))
-      }
+      DecoderResult::OutputFull => Err(WebError::BufferTooSmall),
+      DecoderResult::Malformed(_, _) => Err(WebError::DataInvalid),
     }
   } else {
     let (result, _, written, _) =
@@ -338,7 +339,7 @@ fn op_encoding_decode(
         output.truncate(written);
         Ok(output.into())
       }
-      CoderResult::OutputFull => Err(range_error("Provided buffer too small.")),
+      CoderResult::OutputFull => Err(WebError::BufferTooSmall),
     }
   }
 }
@@ -356,7 +357,7 @@ fn op_encoding_encode_into(
   input: v8::Local<v8::Value>,
   #[buffer] buffer: &mut [u8],
   #[buffer] out_buf: &mut [u32],
-) -> Result<(), AnyError> {
+) -> Result<(), WebError> {
   let s = v8::Local::<v8::String>::try_from(input)?;
 
   let mut nchars = 0;
@@ -414,53 +415,4 @@ pub fn get_declaration() -> PathBuf {
   PathBuf::from(env!("CARGO_MANIFEST_DIR")).join("lib.deno_web.d.ts")
 }
 
-#[derive(Debug)]
-pub struct DomExceptionQuotaExceededError {
-  pub msg: String,
-}
-
-impl DomExceptionQuotaExceededError {
-  pub fn new(msg: &str) -> Self {
-    DomExceptionQuotaExceededError {
-      msg: msg.to_string(),
-    }
-  }
-}
-
-#[derive(Debug)]
-pub struct DomExceptionInvalidCharacterError {
-  pub msg: String,
-}
-
-impl DomExceptionInvalidCharacterError {
-  pub fn new(msg: &str) -> Self {
-    DomExceptionInvalidCharacterError {
-      msg: msg.to_string(),
-    }
-  }
-}
-
-impl fmt::Display for DomExceptionQuotaExceededError {
-  fn fmt(&self, f: &mut fmt::Formatter) -> fmt::Result {
-    f.pad(&self.msg)
-  }
-}
-impl fmt::Display for DomExceptionInvalidCharacterError {
-  fn fmt(&self, f: &mut fmt::Formatter) -> fmt::Result {
-    f.pad(&self.msg)
-  }
-}
-
-impl std::error::Error for DomExceptionQuotaExceededError {}
-
-impl std::error::Error for DomExceptionInvalidCharacterError {}
-
-pub fn get_error_class_name(e: &AnyError) -> Option<&'static str> {
-  e.downcast_ref::<DomExceptionQuotaExceededError>()
-    .map(|_| "DOMExceptionQuotaExceededError")
-    .or_else(|| {
-      e.downcast_ref::<DomExceptionInvalidCharacterError>()
-        .map(|_| "DOMExceptionInvalidCharacterError")
-    })
-}
 pub struct Location(pub Url);
diff --git a/ext/web/message_port.rs b/ext/web/message_port.rs
index c069037f81..1a4a09073d 100644
--- a/ext/web/message_port.rs
+++ b/ext/web/message_port.rs
@@ -4,8 +4,6 @@ use std::borrow::Cow;
 use std::cell::RefCell;
 use std::rc::Rc;
 
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 
 use deno_core::CancelFuture;
@@ -23,6 +21,20 @@ use tokio::sync::mpsc::unbounded_channel;
 use tokio::sync::mpsc::UnboundedReceiver;
 use tokio::sync::mpsc::UnboundedSender;
 
+#[derive(Debug, thiserror::Error)]
+pub enum MessagePortError {
+  #[error("Invalid message port transfer")]
+  InvalidTransfer,
+  #[error("Message port is not ready for transfer")]
+  NotReady,
+  #[error("Can not transfer self message port")]
+  TransferSelf,
+  #[error(transparent)]
+  Canceled(#[from] deno_core::Canceled),
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+}
+
 pub enum Transferable {
   MessagePort(MessagePort),
   ArrayBuffer(u32),
@@ -40,7 +52,7 @@ impl MessagePort {
     &self,
     state: &mut OpState,
     data: JsMessageData,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), MessagePortError> {
     let transferables =
       deserialize_js_transferables(state, data.transferables)?;
 
@@ -56,7 +68,7 @@ impl MessagePort {
   pub async fn recv(
     &self,
     state: Rc<RefCell<OpState>>,
-  ) -> Result<Option<JsMessageData>, AnyError> {
+  ) -> Result<Option<JsMessageData>, MessagePortError> {
     let rx = &self.rx;
 
     let maybe_data = poll_fn(|cx| {
@@ -147,7 +159,7 @@ pub enum JsTransferable {
 pub fn deserialize_js_transferables(
   state: &mut OpState,
   js_transferables: Vec<JsTransferable>,
-) -> Result<Vec<Transferable>, AnyError> {
+) -> Result<Vec<Transferable>, MessagePortError> {
   let mut transferables = Vec::with_capacity(js_transferables.len());
   for js_transferable in js_transferables {
     match js_transferable {
@@ -155,10 +167,10 @@ pub fn deserialize_js_transferables(
         let resource = state
           .resource_table
           .take::<MessagePortResource>(id)
-          .map_err(|_| type_error("Invalid message port transfer"))?;
+          .map_err(|_| MessagePortError::InvalidTransfer)?;
         resource.cancel.cancel();
-        let resource = Rc::try_unwrap(resource)
-          .map_err(|_| type_error("Message port is not ready for transfer"))?;
+        let resource =
+          Rc::try_unwrap(resource).map_err(|_| MessagePortError::NotReady)?;
         transferables.push(Transferable::MessagePort(resource.port));
       }
       JsTransferable::ArrayBuffer(id) => {
@@ -202,16 +214,19 @@ pub fn op_message_port_post_message(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   #[serde] data: JsMessageData,
-) -> Result<(), AnyError> {
+) -> Result<(), MessagePortError> {
   for js_transferable in &data.transferables {
     if let JsTransferable::MessagePort(id) = js_transferable {
       if *id == rid {
-        return Err(type_error("Can not transfer self message port"));
+        return Err(MessagePortError::TransferSelf);
       }
     }
   }
 
-  let resource = state.resource_table.get::<MessagePortResource>(rid)?;
+  let resource = state
+    .resource_table
+    .get::<MessagePortResource>(rid)
+    .map_err(MessagePortError::Resource)?;
   resource.port.send(state, data)
 }
 
@@ -220,7 +235,7 @@ pub fn op_message_port_post_message(
 pub async fn op_message_port_recv_message(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<Option<JsMessageData>, AnyError> {
+) -> Result<Option<JsMessageData>, MessagePortError> {
   let resource = {
     let state = state.borrow();
     match state.resource_table.get::<MessagePortResource>(rid) {
@@ -237,9 +252,11 @@ pub async fn op_message_port_recv_message(
 pub fn op_message_port_recv_message_sync(
   state: &mut OpState, // Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<Option<JsMessageData>, AnyError> {
-  let resource = state.resource_table.get::<MessagePortResource>(rid)?;
-  resource.cancel.cancel();
+) -> Result<Option<JsMessageData>, MessagePortError> {
+  let resource = state
+    .resource_table
+    .get::<MessagePortResource>(rid)
+    .map_err(MessagePortError::Resource)?;
   let mut rx = resource.port.rx.borrow_mut();
 
   match rx.try_recv() {
diff --git a/ext/web/stream_resource.rs b/ext/web/stream_resource.rs
index 78487883b6..c44a385ea9 100644
--- a/ext/web/stream_resource.rs
+++ b/ext/web/stream_resource.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 use bytes::BytesMut;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::external;
 use deno_core::op2;
 use deno_core::serde_v8::V8Slice;
@@ -18,6 +16,7 @@ use deno_core::RcRef;
 use deno_core::Resource;
 use deno_core::ResourceId;
 use futures::future::poll_fn;
+use futures::TryFutureExt;
 use std::borrow::Cow;
 use std::cell::RefCell;
 use std::cell::RefMut;
@@ -31,6 +30,14 @@ use std::task::Context;
 use std::task::Poll;
 use std::task::Waker;
 
+#[derive(Debug, thiserror::Error)]
+pub enum StreamResourceError {
+  #[error(transparent)]
+  Canceled(#[from] deno_core::Canceled),
+  #[error("{0}")]
+  Js(String),
+}
+
 // How many buffers we'll allow in the channel before we stop allowing writes.
 const BUFFER_CHANNEL_SIZE: u16 = 1024;
 
@@ -48,7 +55,7 @@ struct BoundedBufferChannelInner {
   buffers: [MaybeUninit<V8Slice<u8>>; BUFFER_CHANNEL_SIZE as _],
   ring_producer: u16,
   ring_consumer: u16,
-  error: Option<AnyError>,
+  error: Option<StreamResourceError>,
   current_size: usize,
   // TODO(mmastrac): we can math this field instead of accounting for it
   len: usize,
@@ -141,7 +148,10 @@ impl BoundedBufferChannelInner {
     self.len = 0;
   }
 
-  pub fn read(&mut self, limit: usize) -> Result<Option<BufView>, AnyError> {
+  pub fn read(
+    &mut self,
+    limit: usize,
+  ) -> Result<Option<BufView>, StreamResourceError> {
     // Empty buffers will return the error, if one exists, or None
     if self.len == 0 {
       if let Some(error) = self.error.take() {
@@ -230,7 +240,7 @@ impl BoundedBufferChannelInner {
     Ok(())
   }
 
-  pub fn write_error(&mut self, error: AnyError) {
+  pub fn write_error(&mut self, error: StreamResourceError) {
     self.error = Some(error);
     if let Some(waker) = self.read_waker.take() {
       waker.wake();
@@ -306,7 +316,10 @@ impl BoundedBufferChannel {
     self.inner.borrow_mut()
   }
 
-  pub fn read(&self, limit: usize) -> Result<Option<BufView>, AnyError> {
+  pub fn read(
+    &self,
+    limit: usize,
+  ) -> Result<Option<BufView>, StreamResourceError> {
     self.inner().read(limit)
   }
 
@@ -314,7 +327,7 @@ impl BoundedBufferChannel {
     self.inner().write(buffer)
   }
 
-  pub fn write_error(&self, error: AnyError) {
+  pub fn write_error(&self, error: StreamResourceError) {
     self.inner().write_error(error)
   }
 
@@ -358,7 +371,10 @@ impl ReadableStreamResource {
     RcRef::map(self, |s| &s.cancel_handle).clone()
   }
 
-  async fn read(self: Rc<Self>, limit: usize) -> Result<BufView, AnyError> {
+  async fn read(
+    self: Rc<Self>,
+    limit: usize,
+  ) -> Result<BufView, StreamResourceError> {
     let cancel_handle = self.cancel_handle();
     // Serialize all the reads using a task queue.
     let _read_permit = self.read_queue.acquire().await;
@@ -387,7 +403,7 @@ impl Resource for ReadableStreamResource {
   }
 
   fn read(self: Rc<Self>, limit: usize) -> AsyncResult<BufView> {
-    Box::pin(ReadableStreamResource::read(self, limit))
+    Box::pin(ReadableStreamResource::read(self, limit).map_err(|e| e.into()))
   }
 
   fn close(self: Rc<Self>) {
@@ -550,7 +566,7 @@ pub fn op_readable_stream_resource_write_error(
 ) -> bool {
   let sender = get_sender(sender);
   // We can always write an error, no polling required
-  sender.write_error(type_error(Cow::Owned(error)));
+  sender.write_error(StreamResourceError::Js(error));
   !sender.closed()
 }
 
diff --git a/ext/web/timers.rs b/ext/web/timers.rs
index a9ab7c97e4..06444ed34f 100644
--- a/ext/web/timers.rs
+++ b/ext/web/timers.rs
@@ -4,7 +4,10 @@
 
 use deno_core::op2;
 use deno_core::OpState;
+use std::time::Duration;
 use std::time::Instant;
+use std::time::SystemTime;
+use std::time::UNIX_EPOCH;
 
 pub trait TimersPermission {
   fn allow_hrtime(&mut self) -> bool;
@@ -17,21 +20,28 @@ impl TimersPermission for deno_permissions::PermissionsContainer {
   }
 }
 
-pub type StartTime = Instant;
+pub struct StartTime(Instant);
 
-// Returns a milliseconds and nanoseconds subsec
-// since the start time of the deno runtime.
-// If the High precision flag is not set, the
-// nanoseconds are rounded on 2ms.
-#[op2(fast)]
-pub fn op_now<TP>(state: &mut OpState, #[buffer] buf: &mut [u8])
+impl Default for StartTime {
+  fn default() -> Self {
+    Self(Instant::now())
+  }
+}
+
+impl std::ops::Deref for StartTime {
+  type Target = Instant;
+
+  fn deref(&self) -> &Self::Target {
+    &self.0
+  }
+}
+
+fn expose_time<TP>(state: &mut OpState, duration: Duration, out: &mut [u8])
 where
   TP: TimersPermission + 'static,
 {
-  let start_time = state.borrow::<StartTime>();
-  let elapsed = start_time.elapsed();
-  let seconds = elapsed.as_secs();
-  let mut subsec_nanos = elapsed.subsec_nanos();
+  let seconds = duration.as_secs() as u32;
+  let mut subsec_nanos = duration.subsec_nanos();
 
   // If the permission is not enabled
   // Round the nano result on 2 milliseconds
@@ -40,14 +50,33 @@ where
     let reduced_time_precision = 2_000_000; // 2ms in nanoseconds
     subsec_nanos -= subsec_nanos % reduced_time_precision;
   }
-  if buf.len() < 8 {
-    return;
+
+  if out.len() >= 8 {
+    out[0..4].copy_from_slice(&seconds.to_ne_bytes());
+    out[4..8].copy_from_slice(&subsec_nanos.to_ne_bytes());
   }
-  let buf: &mut [u32] =
-    // SAFETY: buffer is at least 8 bytes long.
-    unsafe { std::slice::from_raw_parts_mut(buf.as_mut_ptr() as _, 2) };
-  buf[0] = seconds as u32;
-  buf[1] = subsec_nanos;
+}
+
+#[op2(fast)]
+pub fn op_now<TP>(state: &mut OpState, #[buffer] buf: &mut [u8])
+where
+  TP: TimersPermission + 'static,
+{
+  let start_time = state.borrow::<StartTime>();
+  let elapsed = start_time.elapsed();
+  expose_time::<TP>(state, elapsed, buf);
+}
+
+#[op2(fast)]
+pub fn op_time_origin<TP>(state: &mut OpState, #[buffer] buf: &mut [u8])
+where
+  TP: TimersPermission + 'static,
+{
+  // https://w3c.github.io/hr-time/#dfn-estimated-monotonic-time-of-the-unix-epoch
+  let wall_time = SystemTime::now();
+  let monotonic_time = state.borrow::<StartTime>().elapsed();
+  let epoch = wall_time.duration_since(UNIX_EPOCH).unwrap() - monotonic_time;
+  expose_time::<TP>(state, epoch, buf);
 }
 
 #[allow(clippy::unused_async)]
diff --git a/ext/webgpu/Cargo.toml b/ext/webgpu/Cargo.toml
index b5cff59855..f23bb8371e 100644
--- a/ext/webgpu/Cargo.toml
+++ b/ext/webgpu/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_webgpu"
-version = "0.135.0"
+version = "0.144.0"
 authors = ["the Deno authors"]
 edition.workspace = true
 license = "MIT"
@@ -25,6 +25,7 @@ serde = { workspace = true, features = ["derive"] }
 tokio = { workspace = true, features = ["full"] }
 wgpu-types = { workspace = true, features = ["serde"] }
 raw-window-handle = { workspace = true }
+thiserror.workspace = true
 
 [target.'cfg(not(target_arch = "wasm32"))'.dependencies.wgpu-core]
 workspace = true
diff --git a/ext/webgpu/buffer.rs b/ext/webgpu/buffer.rs
index c6cd6f0a74..c2b53890e0 100644
--- a/ext/webgpu/buffer.rs
+++ b/ext/webgpu/buffer.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::Resource;
@@ -13,9 +11,18 @@ use std::sync::Arc;
 use std::sync::Mutex;
 use std::time::Duration;
 
-use super::error::DomExceptionOperationError;
 use super::error::WebGpuResult;
 
+#[derive(Debug, thiserror::Error)]
+pub enum BufferError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("usage is not valid")]
+  InvalidUsage,
+  #[error(transparent)]
+  Access(wgpu_core::resource::BufferAccessError),
+}
+
 pub(crate) struct WebGpuBuffer(
   pub(crate) super::Instance,
   pub(crate) wgpu_core::id::BufferId,
@@ -46,18 +53,19 @@ pub fn op_webgpu_create_buffer(
   #[number] size: u64,
   usage: u32,
   mapped_at_creation: bool,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, BufferError> {
   let instance = state.borrow::<super::Instance>();
   let device_resource = state
     .resource_table
-    .get::<super::WebGpuDevice>(device_rid)?;
+    .get::<super::WebGpuDevice>(device_rid)
+    .map_err(BufferError::Resource)?;
   let device = device_resource.1;
 
   let descriptor = wgpu_core::resource::BufferDescriptor {
     label: Some(label),
     size,
     usage: wgpu_types::BufferUsages::from_bits(usage)
-      .ok_or_else(|| type_error("usage is not valid"))?,
+      .ok_or(BufferError::InvalidUsage)?,
     mapped_at_creation,
   };
 
@@ -77,18 +85,21 @@ pub async fn op_webgpu_buffer_get_map_async(
   mode: u32,
   #[number] offset: u64,
   #[number] size: u64,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, BufferError> {
   let device;
   let done = Arc::new(Mutex::new(None));
   {
     let state_ = state.borrow();
     let instance = state_.borrow::<super::Instance>();
-    let buffer_resource =
-      state_.resource_table.get::<WebGpuBuffer>(buffer_rid)?;
+    let buffer_resource = state_
+      .resource_table
+      .get::<WebGpuBuffer>(buffer_rid)
+      .map_err(BufferError::Resource)?;
     let buffer = buffer_resource.1;
     let device_resource = state_
       .resource_table
-      .get::<super::WebGpuDevice>(device_rid)?;
+      .get::<super::WebGpuDevice>(device_rid)
+      .map_err(BufferError::Resource)?;
     device = device_resource.1;
 
     let done_ = done.clone();
@@ -120,9 +131,7 @@ pub async fn op_webgpu_buffer_get_map_async(
     let result = done.lock().unwrap().take();
     match result {
       Some(Ok(())) => return Ok(WebGpuResult::empty()),
-      Some(Err(e)) => {
-        return Err(DomExceptionOperationError::new(&e.to_string()).into())
-      }
+      Some(Err(e)) => return Err(BufferError::Access(e)),
       None => {
         {
           let state = state.borrow();
@@ -143,9 +152,12 @@ pub fn op_webgpu_buffer_get_mapped_range(
   #[number] offset: u64,
   #[number] size: Option<u64>,
   #[buffer] buf: &mut [u8],
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, BufferError> {
   let instance = state.borrow::<super::Instance>();
-  let buffer_resource = state.resource_table.get::<WebGpuBuffer>(buffer_rid)?;
+  let buffer_resource = state
+    .resource_table
+    .get::<WebGpuBuffer>(buffer_rid)
+    .map_err(BufferError::Resource)?;
   let buffer = buffer_resource.1;
 
   let (slice_pointer, range_size) =
@@ -154,7 +166,7 @@ pub fn op_webgpu_buffer_get_mapped_range(
       offset,
       size
     ))
-    .map_err(|e| DomExceptionOperationError::new(&e.to_string()))?;
+    .map_err(BufferError::Access)?;
 
   // SAFETY: guarantee to be safe from wgpu
   let slice = unsafe {
@@ -176,12 +188,16 @@ pub fn op_webgpu_buffer_unmap(
   #[smi] buffer_rid: ResourceId,
   #[smi] mapped_rid: ResourceId,
   #[buffer] buf: Option<&[u8]>,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, BufferError> {
   let mapped_resource = state
     .resource_table
-    .take::<WebGpuBufferMapped>(mapped_rid)?;
+    .take::<WebGpuBufferMapped>(mapped_rid)
+    .map_err(BufferError::Resource)?;
   let instance = state.borrow::<super::Instance>();
-  let buffer_resource = state.resource_table.get::<WebGpuBuffer>(buffer_rid)?;
+  let buffer_resource = state
+    .resource_table
+    .get::<WebGpuBuffer>(buffer_rid)
+    .map_err(BufferError::Resource)?;
   let buffer = buffer_resource.1;
 
   if let Some(buf) = buf {
diff --git a/ext/webgpu/bundle.rs b/ext/webgpu/bundle.rs
index 57158271cc..d9a5b29539 100644
--- a/ext/webgpu/bundle.rs
+++ b/ext/webgpu/bundle.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::Resource;
@@ -13,6 +11,14 @@ use std::rc::Rc;
 
 use super::error::WebGpuResult;
 
+#[derive(Debug, thiserror::Error)]
+pub enum BundleError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("size must be larger than 0")]
+  InvalidSize,
+}
+
 struct WebGpuRenderBundleEncoder(
   RefCell<wgpu_core::command::RenderBundleEncoder>,
 );
@@ -53,7 +59,7 @@ pub struct CreateRenderBundleEncoderArgs {
 pub fn op_webgpu_create_render_bundle_encoder(
   state: &mut OpState,
   #[serde] args: CreateRenderBundleEncoderArgs,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let device_resource = state
     .resource_table
     .get::<super::WebGpuDevice>(args.device_rid)?;
@@ -100,7 +106,7 @@ pub fn op_webgpu_render_bundle_encoder_finish(
   state: &mut OpState,
   #[smi] render_bundle_encoder_rid: ResourceId,
   #[string] label: Cow<str>,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_bundle_encoder_resource =
     state
       .resource_table
@@ -131,7 +137,7 @@ pub fn op_webgpu_render_bundle_encoder_set_bind_group(
   #[buffer] dynamic_offsets_data: &[u32],
   #[number] dynamic_offsets_data_start: usize,
   #[number] dynamic_offsets_data_length: usize,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let bind_group_resource =
     state
       .resource_table
@@ -171,7 +177,7 @@ pub fn op_webgpu_render_bundle_encoder_push_debug_group(
   state: &mut OpState,
   #[smi] render_bundle_encoder_rid: ResourceId,
   #[string] group_label: &str,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_bundle_encoder_resource =
     state
       .resource_table
@@ -195,7 +201,7 @@ pub fn op_webgpu_render_bundle_encoder_push_debug_group(
 pub fn op_webgpu_render_bundle_encoder_pop_debug_group(
   state: &mut OpState,
   #[smi] render_bundle_encoder_rid: ResourceId,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_bundle_encoder_resource =
     state
       .resource_table
@@ -214,7 +220,7 @@ pub fn op_webgpu_render_bundle_encoder_insert_debug_marker(
   state: &mut OpState,
   #[smi] render_bundle_encoder_rid: ResourceId,
   #[string] marker_label: &str,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_bundle_encoder_resource =
     state
       .resource_table
@@ -239,7 +245,7 @@ pub fn op_webgpu_render_bundle_encoder_set_pipeline(
   state: &mut OpState,
   #[smi] render_bundle_encoder_rid: ResourceId,
   #[smi] pipeline: ResourceId,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pipeline_resource =
     state
       .resource_table
@@ -266,18 +272,17 @@ pub fn op_webgpu_render_bundle_encoder_set_index_buffer(
   #[serde] index_format: wgpu_types::IndexFormat,
   #[number] offset: u64,
   #[number] size: u64,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, BundleError> {
   let buffer_resource = state
     .resource_table
-    .get::<super::buffer::WebGpuBuffer>(buffer)?;
-  let render_bundle_encoder_resource =
-    state
-      .resource_table
-      .get::<WebGpuRenderBundleEncoder>(render_bundle_encoder_rid)?;
-  let size = Some(
-    std::num::NonZeroU64::new(size)
-      .ok_or_else(|| type_error("size must be larger than 0"))?,
-  );
+    .get::<super::buffer::WebGpuBuffer>(buffer)
+    .map_err(BundleError::Resource)?;
+  let render_bundle_encoder_resource = state
+    .resource_table
+    .get::<WebGpuRenderBundleEncoder>(render_bundle_encoder_rid)
+    .map_err(BundleError::Resource)?;
+  let size =
+    Some(std::num::NonZeroU64::new(size).ok_or(BundleError::InvalidSize)?);
 
   render_bundle_encoder_resource
     .0
@@ -296,19 +301,17 @@ pub fn op_webgpu_render_bundle_encoder_set_vertex_buffer(
   #[smi] buffer: ResourceId,
   #[number] offset: u64,
   #[number] size: Option<u64>,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, BundleError> {
   let buffer_resource = state
     .resource_table
-    .get::<super::buffer::WebGpuBuffer>(buffer)?;
-  let render_bundle_encoder_resource =
-    state
-      .resource_table
-      .get::<WebGpuRenderBundleEncoder>(render_bundle_encoder_rid)?;
+    .get::<super::buffer::WebGpuBuffer>(buffer)
+    .map_err(BundleError::Resource)?;
+  let render_bundle_encoder_resource = state
+    .resource_table
+    .get::<WebGpuRenderBundleEncoder>(render_bundle_encoder_rid)
+    .map_err(BundleError::Resource)?;
   let size = if let Some(size) = size {
-    Some(
-      std::num::NonZeroU64::new(size)
-        .ok_or_else(|| type_error("size must be larger than 0"))?,
-    )
+    Some(std::num::NonZeroU64::new(size).ok_or(BundleError::InvalidSize)?)
   } else {
     None
   };
@@ -333,7 +336,7 @@ pub fn op_webgpu_render_bundle_encoder_draw(
   instance_count: u32,
   first_vertex: u32,
   first_instance: u32,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_bundle_encoder_resource =
     state
       .resource_table
@@ -360,7 +363,7 @@ pub fn op_webgpu_render_bundle_encoder_draw_indexed(
   first_index: u32,
   base_vertex: i32,
   first_instance: u32,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_bundle_encoder_resource =
     state
       .resource_table
@@ -385,7 +388,7 @@ pub fn op_webgpu_render_bundle_encoder_draw_indirect(
   #[smi] render_bundle_encoder_rid: ResourceId,
   #[smi] indirect_buffer: ResourceId,
   #[number] indirect_offset: u64,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let buffer_resource = state
     .resource_table
     .get::<super::buffer::WebGpuBuffer>(indirect_buffer)?;
diff --git a/ext/webgpu/byow.rs b/ext/webgpu/byow.rs
index 3a43f416e5..c9e1177b1e 100644
--- a/ext/webgpu/byow.rs
+++ b/ext/webgpu/byow.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::ResourceId;
@@ -16,6 +14,47 @@ use std::ptr::NonNull;
 
 use crate::surface::WebGpuSurface;
 
+#[derive(Debug, thiserror::Error)]
+pub enum ByowError {
+  #[error("Cannot create surface outside of WebGPU context. Did you forget to call `navigator.gpu.requestAdapter()`?")]
+  WebGPUNotInitiated,
+  #[error("Invalid parameters")]
+  InvalidParameters,
+  #[error(transparent)]
+  CreateSurface(wgpu_core::instance::CreateSurfaceError),
+  #[cfg(target_os = "windows")]
+  #[error("Invalid system on Windows")]
+  InvalidSystem,
+  #[cfg(target_os = "macos")]
+  #[error("Invalid system on macOS")]
+  InvalidSystem,
+  #[cfg(any(
+    target_os = "linux",
+    target_os = "freebsd",
+    target_os = "openbsd"
+  ))]
+  #[error("Invalid system on Linux/BSD")]
+  InvalidSystem,
+  #[cfg(any(
+    target_os = "windows",
+    target_os = "linux",
+    target_os = "freebsd",
+    target_os = "openbsd"
+  ))]
+  #[error("window is null")]
+  NullWindow,
+  #[cfg(any(
+    target_os = "linux",
+    target_os = "freebsd",
+    target_os = "openbsd"
+  ))]
+  #[error("display is null")]
+  NullDisplay,
+  #[cfg(target_os = "macos")]
+  #[error("ns_view is null")]
+  NSViewDisplay,
+}
+
 #[op2(fast)]
 #[smi]
 pub fn op_webgpu_surface_create(
@@ -23,10 +62,10 @@ pub fn op_webgpu_surface_create(
   #[string] system: &str,
   p1: *const c_void,
   p2: *const c_void,
-) -> Result<ResourceId, AnyError> {
-  let instance = state.try_borrow::<super::Instance>().ok_or_else(|| {
-    type_error("Cannot create surface outside of WebGPU context. Did you forget to call `navigator.gpu.requestAdapter()`?")
-  })?;
+) -> Result<ResourceId, ByowError> {
+  let instance = state
+    .try_borrow::<super::Instance>()
+    .ok_or(ByowError::WebGPUNotInitiated)?;
   // Security note:
   //
   // The `p1` and `p2` parameters are pointers to platform-specific window
@@ -41,13 +80,15 @@ pub fn op_webgpu_surface_create(
   //
   // - Only FFI can export v8::External to user code.
   if p1.is_null() {
-    return Err(type_error("Invalid parameters"));
+    return Err(ByowError::InvalidParameters);
   }
 
   let (win_handle, display_handle) = raw_window(system, p1, p2)?;
   // SAFETY: see above comment
   let surface = unsafe {
-    instance.instance_create_surface(display_handle, win_handle, None)?
+    instance
+      .instance_create_surface(display_handle, win_handle, None)
+      .map_err(ByowError::CreateSurface)?
   };
 
   let rid = state
@@ -66,15 +107,14 @@ fn raw_window(
   system: &str,
   _ns_window: *const c_void,
   ns_view: *const c_void,
-) -> Result<RawHandles, AnyError> {
+) -> Result<RawHandles, ByowError> {
   if system != "cocoa" {
-    return Err(type_error("Invalid system on macOS"));
+    return Err(ByowError::InvalidSystem);
   }
 
   let win_handle = raw_window_handle::RawWindowHandle::AppKit(
     raw_window_handle::AppKitWindowHandle::new(
-      NonNull::new(ns_view as *mut c_void)
-        .ok_or(type_error("ns_view is null"))?,
+      NonNull::new(ns_view as *mut c_void).ok_or(ByowError::NSViewDisplay)?,
     ),
   );
 
@@ -89,16 +129,16 @@ fn raw_window(
   system: &str,
   window: *const c_void,
   hinstance: *const c_void,
-) -> Result<RawHandles, AnyError> {
+) -> Result<RawHandles, ByowError> {
   use raw_window_handle::WindowsDisplayHandle;
   if system != "win32" {
-    return Err(type_error("Invalid system on Windows"));
+    return Err(ByowError::InvalidSystem);
   }
 
   let win_handle = {
     let mut handle = raw_window_handle::Win32WindowHandle::new(
       std::num::NonZeroIsize::new(window as isize)
-        .ok_or(type_error("window is null"))?,
+        .ok_or(ByowError::NullWindow)?,
     );
     handle.hinstance = std::num::NonZeroIsize::new(hinstance as isize);
 
@@ -115,7 +155,7 @@ fn raw_window(
   system: &str,
   window: *const c_void,
   display: *const c_void,
-) -> Result<RawHandles, AnyError> {
+) -> Result<RawHandles, ByowError> {
   let (win_handle, display_handle);
   if system == "x11" {
     win_handle = raw_window_handle::RawWindowHandle::Xlib(
@@ -131,19 +171,17 @@ fn raw_window(
   } else if system == "wayland" {
     win_handle = raw_window_handle::RawWindowHandle::Wayland(
       raw_window_handle::WaylandWindowHandle::new(
-        NonNull::new(window as *mut c_void)
-          .ok_or(type_error("window is null"))?,
+        NonNull::new(window as *mut c_void).ok_or(ByowError::NullWindow)?,
       ),
     );
 
     display_handle = raw_window_handle::RawDisplayHandle::Wayland(
       raw_window_handle::WaylandDisplayHandle::new(
-        NonNull::new(display as *mut c_void)
-          .ok_or(type_error("display is null"))?,
+        NonNull::new(display as *mut c_void).ok_or(ByowError::NullDisplay)?,
       ),
     );
   } else {
-    return Err(type_error("Invalid system on Linux/BSD"));
+    return Err(ByowError::InvalidSystem);
   }
 
   Ok((win_handle, display_handle))
@@ -160,6 +198,6 @@ fn raw_window(
   _system: &str,
   _window: *const c_void,
   _display: *const c_void,
-) -> Result<RawHandles, AnyError> {
-  Err(type_error("Unsupported platform"))
+) -> Result<RawHandles, deno_core::error::AnyError> {
+  Err(deno_core::error::type_error("Unsupported platform"))
 }
diff --git a/ext/webgpu/error.rs b/ext/webgpu/error.rs
index 5b55d506ad..f08f765386 100644
--- a/ext/webgpu/error.rs
+++ b/ext/webgpu/error.rs
@@ -1,11 +1,9 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::ResourceId;
 use serde::Serialize;
 use std::convert::From;
 use std::error::Error;
-use std::fmt;
 use wgpu_core::binding_model::CreateBindGroupError;
 use wgpu_core::binding_model::CreateBindGroupLayoutError;
 use wgpu_core::binding_model::CreatePipelineLayoutError;
@@ -286,29 +284,3 @@ impl From<ConfigureSurfaceError> for WebGpuError {
     WebGpuError::Validation(fmt_err(&err))
   }
 }
-
-#[derive(Debug)]
-pub struct DomExceptionOperationError {
-  pub msg: String,
-}
-
-impl DomExceptionOperationError {
-  pub fn new(msg: &str) -> Self {
-    DomExceptionOperationError {
-      msg: msg.to_string(),
-    }
-  }
-}
-
-impl fmt::Display for DomExceptionOperationError {
-  fn fmt(&self, f: &mut fmt::Formatter) -> fmt::Result {
-    f.pad(&self.msg)
-  }
-}
-
-impl std::error::Error for DomExceptionOperationError {}
-
-pub fn get_error_class_name(e: &AnyError) -> Option<&'static str> {
-  e.downcast_ref::<DomExceptionOperationError>()
-    .map(|_| "DOMExceptionOperationError")
-}
diff --git a/ext/webgpu/lib.rs b/ext/webgpu/lib.rs
index df2ab323af..5dc8278e41 100644
--- a/ext/webgpu/lib.rs
+++ b/ext/webgpu/lib.rs
@@ -2,7 +2,6 @@
 #![cfg(not(target_arch = "wasm32"))]
 #![warn(unsafe_op_in_unsafe_fn)]
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::Resource;
@@ -16,7 +15,6 @@ use std::rc::Rc;
 pub use wgpu_core;
 pub use wgpu_types;
 
-use error::DomExceptionOperationError;
 use error::WebGpuResult;
 
 pub const UNSTABLE_FEATURE_NAME: &str = "webgpu";
@@ -44,7 +42,7 @@ mod macros {
         #[cfg(all(not(target_arch = "wasm32"), windows))]
         wgpu_types::Backend::Dx12 => $($c)*.$method::<wgpu_core::api::Dx12> $params,
         #[cfg(any(
-            all(unix, not(target_os = "macos"), not(target_os = "ios")),
+            all(not(target_os = "macos"), not(target_os = "ios")),
             feature = "angle",
             target_arch = "wasm32"
         ))]
@@ -85,6 +83,18 @@ pub mod shader;
 pub mod surface;
 pub mod texture;
 
+#[derive(Debug, thiserror::Error)]
+pub enum InitError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  InvalidAdapter(wgpu_core::instance::InvalidAdapter),
+  #[error(transparent)]
+  RequestDevice(wgpu_core::instance::RequestDeviceError),
+  #[error(transparent)]
+  InvalidDevice(wgpu_core::device::InvalidDevice),
+}
+
 pub type Instance = std::sync::Arc<wgpu_core::global::Global>;
 
 struct WebGpuAdapter(Instance, wgpu_core::id::AdapterId);
@@ -400,7 +410,7 @@ pub fn op_webgpu_request_adapter(
   state: Rc<RefCell<OpState>>,
   #[serde] power_preference: Option<wgpu_types::PowerPreference>,
   force_fallback_adapter: bool,
-) -> Result<GpuAdapterResOrErr, AnyError> {
+) -> Result<GpuAdapterResOrErr, InitError> {
   let mut state = state.borrow_mut();
 
   let backends = std::env::var("DENO_WEBGPU_BACKEND").map_or_else(
@@ -441,10 +451,11 @@ pub fn op_webgpu_request_adapter(
     }
   };
   let adapter_features =
-    gfx_select!(adapter => instance.adapter_features(adapter))?;
+    gfx_select!(adapter => instance.adapter_features(adapter))
+      .map_err(InitError::InvalidAdapter)?;
   let features = deserialize_features(&adapter_features);
-  let adapter_limits =
-    gfx_select!(adapter => instance.adapter_limits(adapter))?;
+  let adapter_limits = gfx_select!(adapter => instance.adapter_limits(adapter))
+    .map_err(InitError::InvalidAdapter)?;
 
   let instance = instance.clone();
 
@@ -663,10 +674,12 @@ pub fn op_webgpu_request_device(
   #[string] label: String,
   #[serde] required_features: GpuRequiredFeatures,
   #[serde] required_limits: Option<wgpu_types::Limits>,
-) -> Result<GpuDeviceRes, AnyError> {
+) -> Result<GpuDeviceRes, InitError> {
   let mut state = state.borrow_mut();
-  let adapter_resource =
-    state.resource_table.take::<WebGpuAdapter>(adapter_rid)?;
+  let adapter_resource = state
+    .resource_table
+    .take::<WebGpuAdapter>(adapter_rid)
+    .map_err(InitError::Resource)?;
   let adapter = adapter_resource.1;
   let instance = state.borrow::<Instance>();
 
@@ -685,13 +698,14 @@ pub fn op_webgpu_request_device(
   ));
   adapter_resource.close();
   if let Some(err) = maybe_err {
-    return Err(DomExceptionOperationError::new(&err.to_string()).into());
+    return Err(InitError::RequestDevice(err));
   }
 
-  let device_features =
-    gfx_select!(device => instance.device_features(device))?;
+  let device_features = gfx_select!(device => instance.device_features(device))
+    .map_err(InitError::InvalidDevice)?;
   let features = deserialize_features(&device_features);
-  let limits = gfx_select!(device => instance.device_limits(device))?;
+  let limits = gfx_select!(device => instance.device_limits(device))
+    .map_err(InitError::InvalidDevice)?;
 
   let instance = instance.clone();
   let instance2 = instance.clone();
@@ -722,14 +736,17 @@ pub struct GPUAdapterInfo {
 pub fn op_webgpu_request_adapter_info(
   state: Rc<RefCell<OpState>>,
   #[smi] adapter_rid: ResourceId,
-) -> Result<GPUAdapterInfo, AnyError> {
+) -> Result<GPUAdapterInfo, InitError> {
   let state = state.borrow_mut();
-  let adapter_resource =
-    state.resource_table.get::<WebGpuAdapter>(adapter_rid)?;
+  let adapter_resource = state
+    .resource_table
+    .get::<WebGpuAdapter>(adapter_rid)
+    .map_err(InitError::Resource)?;
   let adapter = adapter_resource.1;
   let instance = state.borrow::<Instance>();
 
-  let info = gfx_select!(adapter => instance.adapter_get_info(adapter))?;
+  let info = gfx_select!(adapter => instance.adapter_get_info(adapter))
+    .map_err(InitError::InvalidAdapter)?;
 
   Ok(GPUAdapterInfo {
     vendor: info.vendor.to_string(),
@@ -770,9 +787,11 @@ impl From<GpuQueryType> for wgpu_types::QueryType {
 pub fn op_webgpu_create_query_set(
   state: &mut OpState,
   #[serde] args: CreateQuerySetArgs,
-) -> Result<WebGpuResult, AnyError> {
-  let device_resource =
-    state.resource_table.get::<WebGpuDevice>(args.device_rid)?;
+) -> Result<WebGpuResult, InitError> {
+  let device_resource = state
+    .resource_table
+    .get::<WebGpuDevice>(args.device_rid)
+    .map_err(InitError::Resource)?;
   let device = device_resource.1;
   let instance = state.borrow::<Instance>();
 
diff --git a/ext/webgpu/render_pass.rs b/ext/webgpu/render_pass.rs
index c68be3d99a..9b9d87d9fc 100644
--- a/ext/webgpu/render_pass.rs
+++ b/ext/webgpu/render_pass.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::Resource;
@@ -12,6 +10,14 @@ use std::cell::RefCell;
 
 use super::error::WebGpuResult;
 
+#[derive(Debug, thiserror::Error)]
+pub enum RenderPassError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("size must be larger than 0")]
+  InvalidSize,
+}
+
 pub(crate) struct WebGpuRenderPass(
   pub(crate) RefCell<wgpu_core::command::RenderPass>,
 );
@@ -38,7 +44,7 @@ pub struct RenderPassSetViewportArgs {
 pub fn op_webgpu_render_pass_set_viewport(
   state: &mut OpState,
   #[serde] args: RenderPassSetViewportArgs,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(args.render_pass_rid)?;
@@ -65,7 +71,7 @@ pub fn op_webgpu_render_pass_set_scissor_rect(
   y: u32,
   width: u32,
   height: u32,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -87,7 +93,7 @@ pub fn op_webgpu_render_pass_set_blend_constant(
   state: &mut OpState,
   #[smi] render_pass_rid: ResourceId,
   #[serde] color: wgpu_types::Color,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -106,7 +112,7 @@ pub fn op_webgpu_render_pass_set_stencil_reference(
   state: &mut OpState,
   #[smi] render_pass_rid: ResourceId,
   reference: u32,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -125,7 +131,7 @@ pub fn op_webgpu_render_pass_begin_occlusion_query(
   state: &mut OpState,
   #[smi] render_pass_rid: ResourceId,
   query_index: u32,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -143,7 +149,7 @@ pub fn op_webgpu_render_pass_begin_occlusion_query(
 pub fn op_webgpu_render_pass_end_occlusion_query(
   state: &mut OpState,
   #[smi] render_pass_rid: ResourceId,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -161,7 +167,7 @@ pub fn op_webgpu_render_pass_execute_bundles(
   state: &mut OpState,
   #[smi] render_pass_rid: ResourceId,
   #[serde] bundles: Vec<u32>,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let bundles = bundles
     .iter()
     .map(|rid| {
@@ -171,7 +177,7 @@ pub fn op_webgpu_render_pass_execute_bundles(
           .get::<super::bundle::WebGpuRenderBundle>(*rid)?;
       Ok(render_bundle_resource.1)
     })
-    .collect::<Result<Vec<_>, AnyError>>()?;
+    .collect::<Result<Vec<_>, deno_core::error::AnyError>>()?;
 
   let render_pass_resource = state
     .resource_table
@@ -191,7 +197,7 @@ pub fn op_webgpu_render_pass_end(
   state: &mut OpState,
   #[smi] command_encoder_rid: ResourceId,
   #[smi] render_pass_rid: ResourceId,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let command_encoder_resource = state
     .resource_table
     .get::<super::command_encoder::WebGpuCommandEncoder>(
@@ -217,7 +223,7 @@ pub fn op_webgpu_render_pass_set_bind_group(
   #[buffer] dynamic_offsets_data: &[u32],
   #[number] dynamic_offsets_data_start: usize,
   #[number] dynamic_offsets_data_length: usize,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let bind_group_resource =
     state
       .resource_table
@@ -251,7 +257,7 @@ pub fn op_webgpu_render_pass_push_debug_group(
   state: &mut OpState,
   #[smi] render_pass_rid: ResourceId,
   #[string] group_label: &str,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -270,7 +276,7 @@ pub fn op_webgpu_render_pass_push_debug_group(
 pub fn op_webgpu_render_pass_pop_debug_group(
   state: &mut OpState,
   #[smi] render_pass_rid: ResourceId,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -288,7 +294,7 @@ pub fn op_webgpu_render_pass_insert_debug_marker(
   state: &mut OpState,
   #[smi] render_pass_rid: ResourceId,
   #[string] marker_label: &str,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -308,7 +314,7 @@ pub fn op_webgpu_render_pass_set_pipeline(
   state: &mut OpState,
   #[smi] render_pass_rid: ResourceId,
   pipeline: u32,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pipeline_resource =
     state
       .resource_table
@@ -334,19 +340,18 @@ pub fn op_webgpu_render_pass_set_index_buffer(
   #[serde] index_format: wgpu_types::IndexFormat,
   #[number] offset: u64,
   #[number] size: Option<u64>,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, RenderPassError> {
   let buffer_resource = state
     .resource_table
-    .get::<super::buffer::WebGpuBuffer>(buffer)?;
+    .get::<super::buffer::WebGpuBuffer>(buffer)
+    .map_err(RenderPassError::Resource)?;
   let render_pass_resource = state
     .resource_table
-    .get::<WebGpuRenderPass>(render_pass_rid)?;
+    .get::<WebGpuRenderPass>(render_pass_rid)
+    .map_err(RenderPassError::Resource)?;
 
   let size = if let Some(size) = size {
-    Some(
-      std::num::NonZeroU64::new(size)
-        .ok_or_else(|| type_error("size must be larger than 0"))?,
-    )
+    Some(std::num::NonZeroU64::new(size).ok_or(RenderPassError::InvalidSize)?)
   } else {
     None
   };
@@ -370,19 +375,18 @@ pub fn op_webgpu_render_pass_set_vertex_buffer(
   buffer: u32,
   #[number] offset: u64,
   #[number] size: Option<u64>,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, RenderPassError> {
   let buffer_resource = state
     .resource_table
-    .get::<super::buffer::WebGpuBuffer>(buffer)?;
+    .get::<super::buffer::WebGpuBuffer>(buffer)
+    .map_err(RenderPassError::Resource)?;
   let render_pass_resource = state
     .resource_table
-    .get::<WebGpuRenderPass>(render_pass_rid)?;
+    .get::<WebGpuRenderPass>(render_pass_rid)
+    .map_err(RenderPassError::Resource)?;
 
   let size = if let Some(size) = size {
-    Some(
-      std::num::NonZeroU64::new(size)
-        .ok_or_else(|| type_error("size must be larger than 0"))?,
-    )
+    Some(std::num::NonZeroU64::new(size).ok_or(RenderPassError::InvalidSize)?)
   } else {
     None
   };
@@ -407,7 +411,7 @@ pub fn op_webgpu_render_pass_draw(
   instance_count: u32,
   first_vertex: u32,
   first_instance: u32,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -433,7 +437,7 @@ pub fn op_webgpu_render_pass_draw_indexed(
   first_index: u32,
   base_vertex: i32,
   first_instance: u32,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -457,7 +461,7 @@ pub fn op_webgpu_render_pass_draw_indirect(
   #[smi] render_pass_rid: ResourceId,
   indirect_buffer: u32,
   #[number] indirect_offset: u64,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let buffer_resource = state
     .resource_table
     .get::<super::buffer::WebGpuBuffer>(indirect_buffer)?;
@@ -481,7 +485,7 @@ pub fn op_webgpu_render_pass_draw_indexed_indirect(
   #[smi] render_pass_rid: ResourceId,
   indirect_buffer: u32,
   #[number] indirect_offset: u64,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let buffer_resource = state
     .resource_table
     .get::<super::buffer::WebGpuBuffer>(indirect_buffer)?;
diff --git a/ext/webgpu/sampler.rs b/ext/webgpu/sampler.rs
index 27c36802e6..9fc1269ea7 100644
--- a/ext/webgpu/sampler.rs
+++ b/ext/webgpu/sampler.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::Resource;
@@ -47,7 +46,7 @@ pub struct CreateSamplerArgs {
 pub fn op_webgpu_create_sampler(
   state: &mut OpState,
   #[serde] args: CreateSamplerArgs,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let instance = state.borrow::<super::Instance>();
   let device_resource = state
     .resource_table
diff --git a/ext/webgpu/shader.rs b/ext/webgpu/shader.rs
index 0b3991c5de..4653bd85bf 100644
--- a/ext/webgpu/shader.rs
+++ b/ext/webgpu/shader.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::Resource;
@@ -31,7 +30,7 @@ pub fn op_webgpu_create_shader_module(
   #[smi] device_rid: ResourceId,
   #[string] label: Cow<str>,
   #[string] code: Cow<str>,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let instance = state.borrow::<super::Instance>();
   let device_resource = state
     .resource_table
diff --git a/ext/webgpu/surface.rs b/ext/webgpu/surface.rs
index 1f6d2c87d2..297eaeb008 100644
--- a/ext/webgpu/surface.rs
+++ b/ext/webgpu/surface.rs
@@ -1,7 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 use super::WebGpuResult;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::Resource;
@@ -11,6 +10,16 @@ use std::borrow::Cow;
 use std::rc::Rc;
 use wgpu_types::SurfaceStatus;
 
+#[derive(Debug, thiserror::Error)]
+pub enum SurfaceError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("Invalid Surface Status")]
+  InvalidStatus,
+  #[error(transparent)]
+  Surface(wgpu_core::present::SurfaceError),
+}
+
 pub struct WebGpuSurface(pub crate::Instance, pub wgpu_core::id::SurfaceId);
 impl Resource for WebGpuSurface {
   fn name(&self) -> Cow<str> {
@@ -41,7 +50,7 @@ pub struct SurfaceConfigureArgs {
 pub fn op_webgpu_surface_configure(
   state: &mut OpState,
   #[serde] args: SurfaceConfigureArgs,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let instance = state.borrow::<super::Instance>();
   let device_resource = state
     .resource_table
@@ -75,18 +84,22 @@ pub fn op_webgpu_surface_get_current_texture(
   state: &mut OpState,
   #[smi] device_rid: ResourceId,
   #[smi] surface_rid: ResourceId,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, SurfaceError> {
   let instance = state.borrow::<super::Instance>();
   let device_resource = state
     .resource_table
-    .get::<super::WebGpuDevice>(device_rid)?;
+    .get::<super::WebGpuDevice>(device_rid)
+    .map_err(SurfaceError::Resource)?;
   let device = device_resource.1;
-  let surface_resource =
-    state.resource_table.get::<WebGpuSurface>(surface_rid)?;
+  let surface_resource = state
+    .resource_table
+    .get::<WebGpuSurface>(surface_rid)
+    .map_err(SurfaceError::Resource)?;
   let surface = surface_resource.1;
 
   let output =
-    gfx_select!(device => instance.surface_get_current_texture(surface, None))?;
+    gfx_select!(device => instance.surface_get_current_texture(surface, None))
+      .map_err(SurfaceError::Surface)?;
 
   match output.status {
     SurfaceStatus::Good | SurfaceStatus::Suboptimal => {
@@ -98,7 +111,7 @@ pub fn op_webgpu_surface_get_current_texture(
       });
       Ok(WebGpuResult::rid(rid))
     }
-    _ => Err(AnyError::msg("Invalid Surface Status")),
+    _ => Err(SurfaceError::InvalidStatus),
   }
 }
 
@@ -107,17 +120,21 @@ pub fn op_webgpu_surface_present(
   state: &mut OpState,
   #[smi] device_rid: ResourceId,
   #[smi] surface_rid: ResourceId,
-) -> Result<(), AnyError> {
+) -> Result<(), SurfaceError> {
   let instance = state.borrow::<super::Instance>();
   let device_resource = state
     .resource_table
-    .get::<super::WebGpuDevice>(device_rid)?;
+    .get::<super::WebGpuDevice>(device_rid)
+    .map_err(SurfaceError::Resource)?;
   let device = device_resource.1;
-  let surface_resource =
-    state.resource_table.get::<WebGpuSurface>(surface_rid)?;
+  let surface_resource = state
+    .resource_table
+    .get::<WebGpuSurface>(surface_rid)
+    .map_err(SurfaceError::Resource)?;
   let surface = surface_resource.1;
 
-  let _ = gfx_select!(device => instance.surface_present(surface))?;
+  let _ = gfx_select!(device => instance.surface_present(surface))
+    .map_err(SurfaceError::Surface)?;
 
   Ok(())
 }
diff --git a/ext/webgpu/texture.rs b/ext/webgpu/texture.rs
index 44edd1a887..f8a5e05a3e 100644
--- a/ext/webgpu/texture.rs
+++ b/ext/webgpu/texture.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::Resource;
@@ -62,7 +61,7 @@ pub struct CreateTextureArgs {
 pub fn op_webgpu_create_texture(
   state: &mut OpState,
   #[serde] args: CreateTextureArgs,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let instance = state.borrow::<super::Instance>();
   let device_resource = state
     .resource_table
@@ -111,7 +110,7 @@ pub struct CreateTextureViewArgs {
 pub fn op_webgpu_create_texture_view(
   state: &mut OpState,
   #[serde] args: CreateTextureViewArgs,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let instance = state.borrow::<super::Instance>();
   let texture_resource = state
     .resource_table
diff --git a/ext/webidl/Cargo.toml b/ext/webidl/Cargo.toml
index 2f87dc2197..8c3f6f6128 100644
--- a/ext/webidl/Cargo.toml
+++ b/ext/webidl/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_webidl"
-version = "0.168.0"
+version = "0.177.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/websocket/01_websocket.js b/ext/websocket/01_websocket.js
index 58f4773101..468999b95d 100644
--- a/ext/websocket/01_websocket.js
+++ b/ext/websocket/01_websocket.js
@@ -28,6 +28,7 @@ const {
   ArrayPrototypePush,
   ArrayPrototypeShift,
   ArrayPrototypeSome,
+  Error,
   ErrorPrototypeToString,
   ObjectDefineProperties,
   ObjectPrototypeIsPrototypeOf,
@@ -488,8 +489,11 @@ class WebSocket extends EventTarget {
           /* error */
           this[_readyState] = CLOSED;
 
+          const message = op_ws_get_error(rid);
+          const error = new Error(message);
           const errorEv = new ErrorEvent("error", {
-            message: op_ws_get_error(rid),
+            error,
+            message,
           });
           this.dispatchEvent(errorEv);
 
diff --git a/ext/websocket/Cargo.toml b/ext/websocket/Cargo.toml
index 3fc9025466..61f1f5959c 100644
--- a/ext/websocket/Cargo.toml
+++ b/ext/websocket/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_websocket"
-version = "0.173.0"
+version = "0.182.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -28,4 +28,5 @@ hyper-util.workspace = true
 once_cell.workspace = true
 rustls-tokio-stream.workspace = true
 serde.workspace = true
+thiserror.workspace = true
 tokio.workspace = true
diff --git a/ext/websocket/lib.rs b/ext/websocket/lib.rs
index 9e320040b9..a5734271cf 100644
--- a/ext/websocket/lib.rs
+++ b/ext/websocket/lib.rs
@@ -1,10 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 use crate::stream::WebSocketStream;
 use bytes::Bytes;
-use deno_core::anyhow::bail;
-use deno_core::error::invalid_hostname;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::futures::TryFutureExt;
 use deno_core::op2;
 use deno_core::unsync::spawn;
@@ -43,7 +39,6 @@ use serde::Serialize;
 use std::borrow::Cow;
 use std::cell::Cell;
 use std::cell::RefCell;
-use std::fmt;
 use std::future::Future;
 use std::num::NonZeroUsize;
 use std::path::PathBuf;
@@ -55,6 +50,7 @@ use tokio::io::ReadHalf;
 use tokio::io::WriteHalf;
 use tokio::net::TcpStream;
 
+use deno_permissions::PermissionCheckError;
 use fastwebsockets::CloseCode;
 use fastwebsockets::FragmentCollectorRead;
 use fastwebsockets::Frame;
@@ -75,11 +71,33 @@ static USE_WRITEV: Lazy<bool> = Lazy::new(|| {
   false
 });
 
+#[derive(Debug, thiserror::Error)]
+pub enum WebsocketError {
+  #[error(transparent)]
+  Url(url::ParseError),
+  #[error(transparent)]
+  Permission(#[from] PermissionCheckError),
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  Uri(#[from] http::uri::InvalidUri),
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[error(transparent)]
+  WebSocket(#[from] fastwebsockets::WebSocketError),
+  #[error("failed to connect to WebSocket: {0}")]
+  ConnectionFailed(#[from] HandshakeError),
+  #[error(transparent)]
+  Canceled(#[from] deno_core::Canceled),
+}
+
 #[derive(Clone)]
 pub struct WsRootStoreProvider(Option<Arc<dyn RootCertStoreProvider>>);
 
 impl WsRootStoreProvider {
-  pub fn get_or_try_init(&self) -> Result<Option<RootCertStore>, AnyError> {
+  pub fn get_or_try_init(
+    &self,
+  ) -> Result<Option<RootCertStore>, deno_core::error::AnyError> {
     Ok(match &self.0 {
       Some(provider) => Some(provider.get_or_try_init()?.clone()),
       None => None,
@@ -95,7 +113,7 @@ pub trait WebSocketPermissions {
     &mut self,
     _url: &url::Url,
     _api_name: &str,
-  ) -> Result<(), AnyError>;
+  ) -> Result<(), PermissionCheckError>;
 }
 
 impl WebSocketPermissions for deno_permissions::PermissionsContainer {
@@ -104,7 +122,7 @@ impl WebSocketPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     url: &url::Url,
     api_name: &str,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_net_url(self, url, api_name)
   }
 }
@@ -137,13 +155,14 @@ pub fn op_ws_check_permission_and_cancel_handle<WP>(
   #[string] api_name: String,
   #[string] url: String,
   cancel_handle: bool,
-) -> Result<Option<ResourceId>, AnyError>
+) -> Result<Option<ResourceId>, WebsocketError>
 where
   WP: WebSocketPermissions + 'static,
 {
-  state
-    .borrow_mut::<WP>()
-    .check_net_url(&url::Url::parse(&url)?, &api_name)?;
+  state.borrow_mut::<WP>().check_net_url(
+    &url::Url::parse(&url).map_err(WebsocketError::Url)?,
+    &api_name,
+  )?;
 
   if cancel_handle {
     let rid = state
@@ -163,16 +182,46 @@ pub struct CreateResponse {
   extensions: String,
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum HandshakeError {
+  #[error("Missing path in url")]
+  MissingPath,
+  #[error("Invalid status code {0}")]
+  InvalidStatusCode(StatusCode),
+  #[error(transparent)]
+  Http(#[from] http::Error),
+  #[error(transparent)]
+  WebSocket(#[from] fastwebsockets::WebSocketError),
+  #[error("Didn't receive h2 alpn, aborting connection")]
+  NoH2Alpn,
+  #[error(transparent)]
+  Rustls(#[from] deno_tls::rustls::Error),
+  #[error(transparent)]
+  Io(#[from] std::io::Error),
+  #[error(transparent)]
+  H2(#[from] h2::Error),
+  #[error("Invalid hostname: '{0}'")]
+  InvalidHostname(String),
+  #[error(transparent)]
+  RootStoreError(deno_core::error::AnyError),
+  #[error(transparent)]
+  Tls(deno_tls::TlsError),
+  #[error(transparent)]
+  HeaderName(#[from] http::header::InvalidHeaderName),
+  #[error(transparent)]
+  HeaderValue(#[from] http::header::InvalidHeaderValue),
+}
+
 async fn handshake_websocket(
   state: &Rc<RefCell<OpState>>,
   uri: &Uri,
   protocols: &str,
   headers: Option<Vec<(ByteString, ByteString)>>,
-) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), AnyError> {
+) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), HandshakeError> {
   let mut request = Request::builder().method(Method::GET).uri(
     uri
       .path_and_query()
-      .ok_or(type_error("Missing path in url".to_string()))?
+      .ok_or(HandshakeError::MissingPath)?
       .as_str(),
   );
 
@@ -194,7 +243,9 @@ async fn handshake_websocket(
   request =
     populate_common_request_headers(request, &user_agent, protocols, &headers)?;
 
-  let request = request.body(http_body_util::Empty::new())?;
+  let request = request
+    .body(http_body_util::Empty::new())
+    .map_err(HandshakeError::Http)?;
   let domain = &uri.host().unwrap().to_string();
   let port = &uri.port_u16().unwrap_or(match uri.scheme_str() {
     Some("wss") => 443,
@@ -231,7 +282,7 @@ async fn handshake_websocket(
 async fn handshake_http1_ws(
   request: Request<http_body_util::Empty<Bytes>>,
   addr: &String,
-) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), AnyError> {
+) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), HandshakeError> {
   let tcp_socket = TcpStream::connect(addr).await?;
   handshake_connection(request, tcp_socket).await
 }
@@ -241,11 +292,11 @@ async fn handshake_http1_wss(
   request: Request<http_body_util::Empty<Bytes>>,
   domain: &str,
   addr: &str,
-) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), AnyError> {
+) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), HandshakeError> {
   let tcp_socket = TcpStream::connect(addr).await?;
   let tls_config = create_ws_client_config(state, SocketUse::Http1Only)?;
   let dnsname = ServerName::try_from(domain.to_string())
-    .map_err(|_| invalid_hostname(domain))?;
+    .map_err(|_| HandshakeError::InvalidHostname(domain.to_string()))?;
   let mut tls_connector = TlsStream::new_client_side(
     tcp_socket,
     ClientConnection::new(tls_config.into(), dnsname)?,
@@ -266,11 +317,11 @@ async fn handshake_http2_wss(
   domain: &str,
   headers: &Option<Vec<(ByteString, ByteString)>>,
   addr: &str,
-) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), AnyError> {
+) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), HandshakeError> {
   let tcp_socket = TcpStream::connect(addr).await?;
   let tls_config = create_ws_client_config(state, SocketUse::Http2Only)?;
   let dnsname = ServerName::try_from(domain.to_string())
-    .map_err(|_| invalid_hostname(domain))?;
+    .map_err(|_| HandshakeError::InvalidHostname(domain.to_string()))?;
   // We need to better expose the underlying errors here
   let mut tls_connector = TlsStream::new_client_side(
     tcp_socket,
@@ -279,7 +330,7 @@ async fn handshake_http2_wss(
   );
   let handshake = tls_connector.handshake().await?;
   if handshake.alpn.is_none() {
-    bail!("Didn't receive h2 alpn, aborting connection");
+    return Err(HandshakeError::NoH2Alpn);
   }
   let h2 = h2::client::Builder::new();
   let (mut send, conn) = h2.handshake::<_, Bytes>(tls_connector).await?;
@@ -298,7 +349,7 @@ async fn handshake_http2_wss(
   let (resp, send) = send.send_request(request.body(())?, false)?;
   let resp = resp.await?;
   if resp.status() != StatusCode::OK {
-    bail!("Invalid status code: {}", resp.status());
+    return Err(HandshakeError::InvalidStatusCode(resp.status()));
   }
   let (http::response::Parts { headers, .. }, recv) = resp.into_parts();
   let mut stream = WebSocket::after_handshake(
@@ -317,7 +368,7 @@ async fn handshake_connection<
 >(
   request: Request<http_body_util::Empty<Bytes>>,
   socket: S,
-) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), AnyError> {
+) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), HandshakeError> {
   let (upgraded, response) =
     fastwebsockets::handshake::client(&LocalExecutor, request, socket).await?;
 
@@ -332,7 +383,7 @@ async fn handshake_connection<
 pub fn create_ws_client_config(
   state: &Rc<RefCell<OpState>>,
   socket_use: SocketUse,
-) -> Result<ClientConfig, AnyError> {
+) -> Result<ClientConfig, HandshakeError> {
   let unsafely_ignore_certificate_errors: Option<Vec<String>> = state
     .borrow()
     .try_borrow::<UnsafelyIgnoreCertificateErrors>()
@@ -340,7 +391,8 @@ pub fn create_ws_client_config(
   let root_cert_store = state
     .borrow()
     .borrow::<WsRootStoreProvider>()
-    .get_or_try_init()?;
+    .get_or_try_init()
+    .map_err(HandshakeError::RootStoreError)?;
 
   create_client_config(
     root_cert_store,
@@ -349,6 +401,7 @@ pub fn create_ws_client_config(
     TlsKeys::Null,
     socket_use,
   )
+  .map_err(HandshakeError::Tls)
 }
 
 /// Headers common to both http/1.1 and h2 requests.
@@ -357,7 +410,7 @@ fn populate_common_request_headers(
   user_agent: &str,
   protocols: &str,
   headers: &Option<Vec<(ByteString, ByteString)>>,
-) -> Result<http::request::Builder, AnyError> {
+) -> Result<http::request::Builder, HandshakeError> {
   request = request
     .header("User-Agent", user_agent)
     .header("Sec-WebSocket-Version", "13");
@@ -368,10 +421,8 @@ fn populate_common_request_headers(
 
   if let Some(headers) = headers {
     for (key, value) in headers {
-      let name = HeaderName::from_bytes(key)
-        .map_err(|err| type_error(err.to_string()))?;
-      let v = HeaderValue::from_bytes(value)
-        .map_err(|err| type_error(err.to_string()))?;
+      let name = HeaderName::from_bytes(key)?;
+      let v = HeaderValue::from_bytes(value)?;
 
       let is_disallowed_header = matches!(
         name,
@@ -401,14 +452,17 @@ pub async fn op_ws_create<WP>(
   #[string] protocols: String,
   #[smi] cancel_handle: Option<ResourceId>,
   #[serde] headers: Option<Vec<(ByteString, ByteString)>>,
-) -> Result<CreateResponse, AnyError>
+) -> Result<CreateResponse, WebsocketError>
 where
   WP: WebSocketPermissions + 'static,
 {
   {
     let mut s = state.borrow_mut();
     s.borrow_mut::<WP>()
-      .check_net_url(&url::Url::parse(&url)?, &api_name)
+      .check_net_url(
+        &url::Url::parse(&url).map_err(WebsocketError::Url)?,
+        &api_name,
+      )
       .expect(
         "Permission check should have been done in op_ws_check_permission",
       );
@@ -418,7 +472,8 @@ where
     let r = state
       .borrow_mut()
       .resource_table
-      .get::<WsCancelResource>(cancel_rid)?;
+      .get::<WsCancelResource>(cancel_rid)
+      .map_err(WebsocketError::Resource)?;
     Some(r.0.clone())
   } else {
     None
@@ -427,15 +482,11 @@ where
   let uri: Uri = url.parse()?;
 
   let handshake = handshake_websocket(&state, &uri, &protocols, headers)
-    .map_err(|err| {
-      AnyError::from(DomExceptionNetworkError::new(&format!(
-        "failed to connect to WebSocket: {err}"
-      )))
-    });
+    .map_err(WebsocketError::ConnectionFailed);
   let (stream, response) = match cancel_resource {
-    Some(rc) => handshake.try_or_cancel(rc).await,
-    None => handshake.await,
-  }?;
+    Some(rc) => handshake.try_or_cancel(rc).await?,
+    None => handshake.await?,
+  };
 
   if let Some(cancel_rid) = cancel_handle {
     if let Ok(res) = state.borrow_mut().resource_table.take_any(cancel_rid) {
@@ -520,14 +571,12 @@ impl ServerWebSocket {
     self: &Rc<Self>,
     lock: AsyncMutFuture<WebSocketWrite<WriteHalf<WebSocketStream>>>,
     frame: Frame<'_>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), WebsocketError> {
     let mut ws = lock.await;
     if ws.is_closed() {
       return Ok(());
     }
-    ws.write_frame(frame)
-      .await
-      .map_err(|err| type_error(err.to_string()))?;
+    ws.write_frame(frame).await?;
     Ok(())
   }
 }
@@ -542,7 +591,7 @@ pub fn ws_create_server_stream(
   state: &mut OpState,
   transport: NetworkStream,
   read_buf: Bytes,
-) -> Result<ResourceId, AnyError> {
+) -> ResourceId {
   let mut ws = WebSocket::after_handshake(
     WebSocketStream::new(
       stream::WsStreamKind::Network(transport),
@@ -554,8 +603,7 @@ pub fn ws_create_server_stream(
   ws.set_auto_close(true);
   ws.set_auto_pong(true);
 
-  let rid = state.resource_table.add(ServerWebSocket::new(ws));
-  Ok(rid)
+  state.resource_table.add(ServerWebSocket::new(ws))
 }
 
 fn send_binary(state: &mut OpState, rid: ResourceId, data: &[u8]) {
@@ -625,11 +673,12 @@ pub async fn op_ws_send_binary_async(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[buffer] data: JsBuffer,
-) -> Result<(), AnyError> {
+) -> Result<(), WebsocketError> {
   let resource = state
     .borrow_mut()
     .resource_table
-    .get::<ServerWebSocket>(rid)?;
+    .get::<ServerWebSocket>(rid)
+    .map_err(WebsocketError::Resource)?;
   let data = data.to_vec();
   let lock = resource.reserve_lock();
   resource
@@ -643,11 +692,12 @@ pub async fn op_ws_send_text_async(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[string] data: String,
-) -> Result<(), AnyError> {
+) -> Result<(), WebsocketError> {
   let resource = state
     .borrow_mut()
     .resource_table
-    .get::<ServerWebSocket>(rid)?;
+    .get::<ServerWebSocket>(rid)
+    .map_err(WebsocketError::Resource)?;
   let lock = resource.reserve_lock();
   resource
     .write_frame(
@@ -677,11 +727,12 @@ pub fn op_ws_get_buffered_amount(
 pub async fn op_ws_send_ping(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
+) -> Result<(), WebsocketError> {
   let resource = state
     .borrow_mut()
     .resource_table
-    .get::<ServerWebSocket>(rid)?;
+    .get::<ServerWebSocket>(rid)
+    .map_err(WebsocketError::Resource)?;
   let lock = resource.reserve_lock();
   resource
     .write_frame(
@@ -697,7 +748,7 @@ pub async fn op_ws_close(
   #[smi] rid: ResourceId,
   #[smi] code: Option<u16>,
   #[string] reason: Option<String>,
-) -> Result<(), AnyError> {
+) -> Result<(), WebsocketError> {
   let Ok(resource) = state
     .borrow_mut()
     .resource_table
@@ -712,8 +763,7 @@ pub async fn op_ws_close(
 
   resource.closed.set(true);
   let lock = resource.reserve_lock();
-  resource.write_frame(lock, frame).await?;
-  Ok(())
+  resource.write_frame(lock, frame).await
 }
 
 #[op2]
@@ -867,32 +917,6 @@ pub fn get_declaration() -> PathBuf {
   PathBuf::from(env!("CARGO_MANIFEST_DIR")).join("lib.deno_websocket.d.ts")
 }
 
-#[derive(Debug)]
-pub struct DomExceptionNetworkError {
-  pub msg: String,
-}
-
-impl DomExceptionNetworkError {
-  pub fn new(msg: &str) -> Self {
-    DomExceptionNetworkError {
-      msg: msg.to_string(),
-    }
-  }
-}
-
-impl fmt::Display for DomExceptionNetworkError {
-  fn fmt(&self, f: &mut fmt::Formatter) -> fmt::Result {
-    f.pad(&self.msg)
-  }
-}
-
-impl std::error::Error for DomExceptionNetworkError {}
-
-pub fn get_network_error_class_name(e: &AnyError) -> Option<&'static str> {
-  e.downcast_ref::<DomExceptionNetworkError>()
-    .map(|_| "DOMExceptionNetworkError")
-}
-
 // Needed so hyper can use non Send futures
 #[derive(Clone)]
 struct LocalExecutor;
diff --git a/ext/webstorage/01_webstorage.js b/ext/webstorage/01_webstorage.js
index 3cbdd708dd..9e86366563 100644
--- a/ext/webstorage/01_webstorage.js
+++ b/ext/webstorage/01_webstorage.js
@@ -143,6 +143,9 @@ function createStorage(persistent) {
       if (ReflectHas(target, key)) {
         return undefined;
       }
+      if (typeof key === "symbol") {
+        return undefined;
+      }
       const value = target.getItem(key);
       if (value === null) {
         return undefined;
diff --git a/ext/webstorage/Cargo.toml b/ext/webstorage/Cargo.toml
index fbcd17edf9..01e23ab839 100644
--- a/ext/webstorage/Cargo.toml
+++ b/ext/webstorage/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_webstorage"
-version = "0.163.0"
+version = "0.172.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -17,3 +17,4 @@ path = "lib.rs"
 deno_core.workspace = true
 deno_web.workspace = true
 rusqlite.workspace = true
+thiserror.workspace = true
diff --git a/ext/webstorage/lib.rs b/ext/webstorage/lib.rs
index 99e61a1804..40946f05a7 100644
--- a/ext/webstorage/lib.rs
+++ b/ext/webstorage/lib.rs
@@ -2,10 +2,8 @@
 
 // NOTE to all: use **cached** prepared statements when interfacing with SQLite.
 
-use std::fmt;
 use std::path::PathBuf;
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use rusqlite::params;
@@ -14,6 +12,18 @@ use rusqlite::OptionalExtension;
 
 pub use rusqlite;
 
+#[derive(Debug, thiserror::Error)]
+pub enum WebStorageError {
+  #[error("LocalStorage is not supported in this context.")]
+  ContextNotSupported,
+  #[error(transparent)]
+  Sqlite(#[from] rusqlite::Error),
+  #[error(transparent)]
+  Io(std::io::Error),
+  #[error("Exceeded maximum storage size")]
+  StorageExceeded,
+}
+
 #[derive(Clone)]
 struct OriginStorageDir(PathBuf);
 
@@ -51,15 +61,13 @@ struct SessionStorage(Connection);
 fn get_webstorage(
   state: &mut OpState,
   persistent: bool,
-) -> Result<&Connection, AnyError> {
+) -> Result<&Connection, WebStorageError> {
   let conn = if persistent {
     if state.try_borrow::<LocalStorage>().is_none() {
-      let path = state.try_borrow::<OriginStorageDir>().ok_or_else(|| {
-        DomExceptionNotSupportedError::new(
-          "LocalStorage is not supported in this context.",
-        )
-      })?;
-      std::fs::create_dir_all(&path.0)?;
+      let path = state
+        .try_borrow::<OriginStorageDir>()
+        .ok_or(WebStorageError::ContextNotSupported)?;
+      std::fs::create_dir_all(&path.0).map_err(WebStorageError::Io)?;
       let conn = Connection::open(path.0.join("local_storage"))?;
       // Enable write-ahead-logging and tweak some other stuff.
       let initial_pragmas = "
@@ -106,7 +114,7 @@ fn get_webstorage(
 pub fn op_webstorage_length(
   state: &mut OpState,
   persistent: bool,
-) -> Result<u32, AnyError> {
+) -> Result<u32, WebStorageError> {
   let conn = get_webstorage(state, persistent)?;
 
   let mut stmt = conn.prepare_cached("SELECT COUNT(*) FROM data")?;
@@ -121,7 +129,7 @@ pub fn op_webstorage_key(
   state: &mut OpState,
   #[smi] index: u32,
   persistent: bool,
-) -> Result<Option<String>, AnyError> {
+) -> Result<Option<String>, WebStorageError> {
   let conn = get_webstorage(state, persistent)?;
 
   let mut stmt =
@@ -135,14 +143,9 @@ pub fn op_webstorage_key(
 }
 
 #[inline]
-fn size_check(input: usize) -> Result<(), AnyError> {
+fn size_check(input: usize) -> Result<(), WebStorageError> {
   if input >= MAX_STORAGE_BYTES {
-    return Err(
-      deno_web::DomExceptionQuotaExceededError::new(
-        "Exceeded maximum storage size",
-      )
-      .into(),
-    );
+    return Err(WebStorageError::StorageExceeded);
   }
 
   Ok(())
@@ -154,7 +157,7 @@ pub fn op_webstorage_set(
   #[string] key: &str,
   #[string] value: &str,
   persistent: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), WebStorageError> {
   let conn = get_webstorage(state, persistent)?;
 
   size_check(key.len() + value.len())?;
@@ -178,7 +181,7 @@ pub fn op_webstorage_get(
   state: &mut OpState,
   #[string] key_name: String,
   persistent: bool,
-) -> Result<Option<String>, AnyError> {
+) -> Result<Option<String>, WebStorageError> {
   let conn = get_webstorage(state, persistent)?;
 
   let mut stmt = conn.prepare_cached("SELECT value FROM data WHERE key = ?")?;
@@ -194,7 +197,7 @@ pub fn op_webstorage_remove(
   state: &mut OpState,
   #[string] key_name: &str,
   persistent: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), WebStorageError> {
   let conn = get_webstorage(state, persistent)?;
 
   let mut stmt = conn.prepare_cached("DELETE FROM data WHERE key = ?")?;
@@ -207,7 +210,7 @@ pub fn op_webstorage_remove(
 pub fn op_webstorage_clear(
   state: &mut OpState,
   persistent: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), WebStorageError> {
   let conn = get_webstorage(state, persistent)?;
 
   let mut stmt = conn.prepare_cached("DELETE FROM data")?;
@@ -221,7 +224,7 @@ pub fn op_webstorage_clear(
 pub fn op_webstorage_iterate_keys(
   state: &mut OpState,
   persistent: bool,
-) -> Result<Vec<String>, AnyError> {
+) -> Result<Vec<String>, WebStorageError> {
   let conn = get_webstorage(state, persistent)?;
 
   let mut stmt = conn.prepare_cached("SELECT key FROM data")?;
@@ -232,31 +235,3 @@ pub fn op_webstorage_iterate_keys(
 
   Ok(keys)
 }
-
-#[derive(Debug)]
-pub struct DomExceptionNotSupportedError {
-  pub msg: String,
-}
-
-impl DomExceptionNotSupportedError {
-  pub fn new(msg: &str) -> Self {
-    DomExceptionNotSupportedError {
-      msg: msg.to_string(),
-    }
-  }
-}
-
-impl fmt::Display for DomExceptionNotSupportedError {
-  fn fmt(&self, f: &mut fmt::Formatter) -> fmt::Result {
-    f.pad(&self.msg)
-  }
-}
-
-impl std::error::Error for DomExceptionNotSupportedError {}
-
-pub fn get_not_supported_error_class_name(
-  e: &AnyError,
-) -> Option<&'static str> {
-  e.downcast_ref::<DomExceptionNotSupportedError>()
-    .map(|_| "DOMExceptionNotSupportedError")
-}
diff --git a/resolvers/deno/Cargo.toml b/resolvers/deno/Cargo.toml
new file mode 100644
index 0000000000..89c0232dc9
--- /dev/null
+++ b/resolvers/deno/Cargo.toml
@@ -0,0 +1,31 @@
+# Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+[package]
+name = "deno_resolver"
+version = "0.9.0"
+authors.workspace = true
+edition.workspace = true
+license.workspace = true
+readme = "README.md"
+repository.workspace = true
+description = "Deno resolution algorithm"
+
+[lib]
+path = "lib.rs"
+
+[dependencies]
+anyhow.workspace = true
+base32.workspace = true
+dashmap.workspace = true
+deno_config.workspace = true
+deno_media_type.workspace = true
+deno_package_json.workspace = true
+deno_package_json.features = ["sync"]
+deno_path_util.workspace = true
+deno_semver.workspace = true
+node_resolver.workspace = true
+thiserror.workspace = true
+url.workspace = true
+
+[dev-dependencies]
+test_util.workspace = true
diff --git a/resolvers/deno/README.md b/resolvers/deno/README.md
new file mode 100644
index 0000000000..f51619a314
--- /dev/null
+++ b/resolvers/deno/README.md
@@ -0,0 +1,3 @@
+# deno_resolver
+
+Deno resolution algorithm.
diff --git a/resolvers/deno/cjs.rs b/resolvers/deno/cjs.rs
new file mode 100644
index 0000000000..dbcbd8b6bf
--- /dev/null
+++ b/resolvers/deno/cjs.rs
@@ -0,0 +1,272 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+use std::sync::Arc;
+
+use dashmap::DashMap;
+use deno_media_type::MediaType;
+use node_resolver::env::NodeResolverEnv;
+use node_resolver::errors::ClosestPkgJsonError;
+use node_resolver::InNpmPackageChecker;
+use node_resolver::NodeModuleKind;
+use node_resolver::PackageJsonResolver;
+use url::Url;
+
+/// Keeps track of what module specifiers were resolved as CJS.
+///
+/// Modules that are `.js`, `.ts`, `.jsx`, and `tsx` are only known to
+/// be CJS or ESM after they're loaded based on their contents. So these
+/// files will be "maybe CJS" until they're loaded.
+#[derive(Debug)]
+pub struct CjsTracker<TEnv: NodeResolverEnv> {
+  is_cjs_resolver: IsCjsResolver<TEnv>,
+  known: DashMap<Url, NodeModuleKind>,
+}
+
+impl<TEnv: NodeResolverEnv> CjsTracker<TEnv> {
+  pub fn new(
+    in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+    pkg_json_resolver: Arc<PackageJsonResolver<TEnv>>,
+    options: IsCjsResolverOptions,
+  ) -> Self {
+    Self {
+      is_cjs_resolver: IsCjsResolver::new(
+        in_npm_pkg_checker,
+        pkg_json_resolver,
+        options,
+      ),
+      known: Default::default(),
+    }
+  }
+
+  /// Checks whether the file might be treated as CJS, but it's not for sure
+  /// yet because the source hasn't been loaded to see whether it contains
+  /// imports or exports.
+  pub fn is_maybe_cjs(
+    &self,
+    specifier: &Url,
+    media_type: MediaType,
+  ) -> Result<bool, ClosestPkgJsonError> {
+    self.treat_as_cjs_with_is_script(specifier, media_type, None)
+  }
+
+  /// Gets whether the file is CJS. If true, this is for sure
+  /// cjs because `is_script` is provided.
+  ///
+  /// `is_script` should be `true` when the contents of the file at the
+  /// provided specifier are known to be a script and not an ES module.
+  pub fn is_cjs_with_known_is_script(
+    &self,
+    specifier: &Url,
+    media_type: MediaType,
+    is_script: bool,
+  ) -> Result<bool, ClosestPkgJsonError> {
+    self.treat_as_cjs_with_is_script(specifier, media_type, Some(is_script))
+  }
+
+  fn treat_as_cjs_with_is_script(
+    &self,
+    specifier: &Url,
+    media_type: MediaType,
+    is_script: Option<bool>,
+  ) -> Result<bool, ClosestPkgJsonError> {
+    let kind = match self
+      .get_known_kind_with_is_script(specifier, media_type, is_script)
+    {
+      Some(kind) => kind,
+      None => self.is_cjs_resolver.check_based_on_pkg_json(specifier)?,
+    };
+    Ok(kind == NodeModuleKind::Cjs)
+  }
+
+  /// Gets the referrer for the specified module specifier.
+  ///
+  /// Generally the referrer should already be tracked by calling
+  /// `is_cjs_with_known_is_script` before calling this method.
+  pub fn get_referrer_kind(&self, specifier: &Url) -> NodeModuleKind {
+    if specifier.scheme() != "file" {
+      return NodeModuleKind::Esm;
+    }
+    self
+      .get_known_kind(specifier, MediaType::from_specifier(specifier))
+      .unwrap_or(NodeModuleKind::Esm)
+  }
+
+  fn get_known_kind(
+    &self,
+    specifier: &Url,
+    media_type: MediaType,
+  ) -> Option<NodeModuleKind> {
+    self.get_known_kind_with_is_script(specifier, media_type, None)
+  }
+
+  fn get_known_kind_with_is_script(
+    &self,
+    specifier: &Url,
+    media_type: MediaType,
+    is_script: Option<bool>,
+  ) -> Option<NodeModuleKind> {
+    self.is_cjs_resolver.get_known_kind_with_is_script(
+      specifier,
+      media_type,
+      is_script,
+      &self.known,
+    )
+  }
+}
+
+#[derive(Debug)]
+pub struct IsCjsResolverOptions {
+  pub detect_cjs: bool,
+  pub is_node_main: bool,
+}
+
+/// Resolves whether a module is CJS or ESM.
+#[derive(Debug)]
+pub struct IsCjsResolver<TEnv: NodeResolverEnv> {
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+  pkg_json_resolver: Arc<PackageJsonResolver<TEnv>>,
+  options: IsCjsResolverOptions,
+}
+
+impl<TEnv: NodeResolverEnv> IsCjsResolver<TEnv> {
+  pub fn new(
+    in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+    pkg_json_resolver: Arc<PackageJsonResolver<TEnv>>,
+    options: IsCjsResolverOptions,
+  ) -> Self {
+    Self {
+      in_npm_pkg_checker,
+      pkg_json_resolver,
+      options,
+    }
+  }
+
+  /// Gets the referrer kind for a script in the LSP.
+  pub fn get_lsp_referrer_kind(
+    &self,
+    specifier: &Url,
+    is_script: Option<bool>,
+  ) -> NodeModuleKind {
+    if specifier.scheme() != "file" {
+      return NodeModuleKind::Esm;
+    }
+    match MediaType::from_specifier(specifier) {
+      MediaType::Mts | MediaType::Mjs | MediaType::Dmts => NodeModuleKind::Esm,
+      MediaType::Cjs | MediaType::Cts | MediaType::Dcts => NodeModuleKind::Cjs,
+      MediaType::Dts => {
+        // dts files are always determined based on the package.json because
+        // they contain imports/exports even when considered CJS
+        self.check_based_on_pkg_json(specifier).unwrap_or(NodeModuleKind::Esm)
+      }
+      MediaType::Wasm |
+      MediaType::Json => NodeModuleKind::Esm,
+      MediaType::JavaScript
+      | MediaType::Jsx
+      | MediaType::TypeScript
+      | MediaType::Tsx
+      // treat these as unknown
+      | MediaType::Css
+      | MediaType::SourceMap
+      | MediaType::Unknown => {
+        match is_script {
+          Some(true) => self.check_based_on_pkg_json(specifier).unwrap_or(NodeModuleKind::Esm),
+          Some(false) | None => NodeModuleKind::Esm,
+        }
+      }
+    }
+  }
+
+  fn get_known_kind_with_is_script(
+    &self,
+    specifier: &Url,
+    media_type: MediaType,
+    is_script: Option<bool>,
+    known_cache: &DashMap<Url, NodeModuleKind>,
+  ) -> Option<NodeModuleKind> {
+    if specifier.scheme() != "file" {
+      return Some(NodeModuleKind::Esm);
+    }
+
+    match media_type {
+      MediaType::Mts | MediaType::Mjs | MediaType::Dmts => Some(NodeModuleKind::Esm),
+      MediaType::Cjs | MediaType::Cts | MediaType::Dcts => Some(NodeModuleKind::Cjs),
+      MediaType::Dts => {
+        // dts files are always determined based on the package.json because
+        // they contain imports/exports even when considered CJS
+        if let Some(value) = known_cache.get(specifier).map(|v| *v) {
+          Some(value)
+        } else {
+          let value = self.check_based_on_pkg_json(specifier).ok();
+          if let Some(value) = value {
+            known_cache.insert(specifier.clone(), value);
+          }
+          Some(value.unwrap_or(NodeModuleKind::Esm))
+        }
+      }
+      MediaType::Wasm |
+      MediaType::Json => Some(NodeModuleKind::Esm),
+      MediaType::JavaScript
+      | MediaType::Jsx
+      | MediaType::TypeScript
+      | MediaType::Tsx
+      // treat these as unknown
+      | MediaType::Css
+      | MediaType::SourceMap
+      | MediaType::Unknown => {
+        if let Some(value) = known_cache.get(specifier).map(|v| *v) {
+          if value == NodeModuleKind::Cjs && is_script == Some(false) {
+            // we now know this is actually esm
+            known_cache.insert(specifier.clone(), NodeModuleKind::Esm);
+            Some(NodeModuleKind::Esm)
+          } else {
+            Some(value)
+          }
+        } else if is_script == Some(false) {
+          // we know this is esm
+            known_cache.insert(specifier.clone(), NodeModuleKind::Esm);
+          Some(NodeModuleKind::Esm)
+        } else {
+          None
+        }
+      }
+    }
+  }
+
+  fn check_based_on_pkg_json(
+    &self,
+    specifier: &Url,
+  ) -> Result<NodeModuleKind, ClosestPkgJsonError> {
+    if self.in_npm_pkg_checker.in_npm_package(specifier) {
+      if let Some(pkg_json) =
+        self.pkg_json_resolver.get_closest_package_json(specifier)?
+      {
+        let is_file_location_cjs = pkg_json.typ != "module";
+        Ok(if is_file_location_cjs {
+          NodeModuleKind::Cjs
+        } else {
+          NodeModuleKind::Esm
+        })
+      } else {
+        Ok(NodeModuleKind::Cjs)
+      }
+    } else if self.options.detect_cjs || self.options.is_node_main {
+      if let Some(pkg_json) =
+        self.pkg_json_resolver.get_closest_package_json(specifier)?
+      {
+        let is_cjs_type = pkg_json.typ == "commonjs"
+          || self.options.is_node_main && pkg_json.typ == "none";
+        Ok(if is_cjs_type {
+          NodeModuleKind::Cjs
+        } else {
+          NodeModuleKind::Esm
+        })
+      } else if self.options.is_node_main {
+        Ok(NodeModuleKind::Cjs)
+      } else {
+        Ok(NodeModuleKind::Esm)
+      }
+    } else {
+      Ok(NodeModuleKind::Esm)
+    }
+  }
+}
diff --git a/resolvers/deno/clippy.toml b/resolvers/deno/clippy.toml
new file mode 100644
index 0000000000..733ac83da1
--- /dev/null
+++ b/resolvers/deno/clippy.toml
@@ -0,0 +1,52 @@
+disallowed-methods = [
+  { path = "std::env::current_dir", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::Path::canonicalize", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::Path::is_dir", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::Path::is_file", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::Path::is_symlink", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::Path::metadata", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::Path::read_dir", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::Path::read_link", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::Path::symlink_metadata", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::Path::try_exists", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::PathBuf::exists", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::PathBuf::canonicalize", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::PathBuf::is_dir", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::PathBuf::is_file", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::PathBuf::is_symlink", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::PathBuf::metadata", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::PathBuf::read_dir", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::PathBuf::read_link", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::PathBuf::symlink_metadata", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::PathBuf::try_exists", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::env::set_current_dir", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::env::temp_dir", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::canonicalize", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::copy", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::create_dir_all", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::create_dir", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::DirBuilder::new", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::hard_link", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::metadata", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::OpenOptions::new", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::read_dir", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::read_link", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::read_to_string", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::read", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::remove_dir_all", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::remove_dir", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::remove_file", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::rename", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::set_permissions", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::symlink_metadata", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::fs::write", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::Path::canonicalize", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "std::path::Path::exists", reason = "File system operations should be done using DenoResolverFs trait" },
+  { path = "url::Url::to_file_path", reason = "Use deno_path_util instead so it works in Wasm" },
+  { path = "url::Url::from_file_path", reason = "Use deno_path_util instead so it works in Wasm" },
+  { path = "url::Url::from_directory_path", reason = "Use deno_path_util instead so it works in Wasm" },
+]
+disallowed-types = [
+  # todo(dsherret): consider for the future
+  # { path = "std::sync::Arc", reason = "use crate::sync::MaybeArc instead" },
+]
diff --git a/resolvers/deno/fs.rs b/resolvers/deno/fs.rs
new file mode 100644
index 0000000000..4929f4508e
--- /dev/null
+++ b/resolvers/deno/fs.rs
@@ -0,0 +1,18 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+use std::path::Path;
+use std::path::PathBuf;
+
+pub struct DirEntry {
+  pub name: String,
+  pub is_file: bool,
+  pub is_directory: bool,
+}
+
+pub trait DenoResolverFs {
+  fn read_to_string_lossy(&self, path: &Path) -> std::io::Result<String>;
+  fn realpath_sync(&self, path: &Path) -> std::io::Result<PathBuf>;
+  fn exists_sync(&self, path: &Path) -> bool;
+  fn is_dir_sync(&self, path: &Path) -> bool;
+  fn read_dir_sync(&self, dir_path: &Path) -> std::io::Result<Vec<DirEntry>>;
+}
diff --git a/resolvers/deno/lib.rs b/resolvers/deno/lib.rs
new file mode 100644
index 0000000000..a2b6b642fc
--- /dev/null
+++ b/resolvers/deno/lib.rs
@@ -0,0 +1,439 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+#![deny(clippy::print_stderr)]
+#![deny(clippy::print_stdout)]
+
+use std::path::PathBuf;
+use std::sync::Arc;
+
+use deno_config::workspace::MappedResolution;
+use deno_config::workspace::MappedResolutionDiagnostic;
+use deno_config::workspace::MappedResolutionError;
+use deno_config::workspace::WorkspaceResolvePkgJsonFolderError;
+use deno_config::workspace::WorkspaceResolver;
+use deno_package_json::PackageJsonDepValue;
+use deno_package_json::PackageJsonDepValueParseError;
+use deno_semver::npm::NpmPackageReqReference;
+use fs::DenoResolverFs;
+use node_resolver::env::NodeResolverEnv;
+use node_resolver::errors::NodeResolveError;
+use node_resolver::errors::PackageSubpathResolveError;
+use node_resolver::InNpmPackageChecker;
+use node_resolver::NodeModuleKind;
+use node_resolver::NodeResolution;
+use node_resolver::NodeResolutionMode;
+use node_resolver::NodeResolver;
+use npm::MissingPackageNodeModulesFolderError;
+use npm::NodeModulesOutOfDateError;
+use npm::NpmReqResolver;
+use npm::ResolveIfForNpmPackageError;
+use npm::ResolvePkgFolderFromDenoReqError;
+use npm::ResolveReqWithSubPathError;
+use sloppy_imports::SloppyImportResolverFs;
+use sloppy_imports::SloppyImportsResolutionMode;
+use sloppy_imports::SloppyImportsResolver;
+use thiserror::Error;
+use url::Url;
+
+pub mod cjs;
+pub mod fs;
+pub mod npm;
+pub mod sloppy_imports;
+
+#[derive(Debug, Clone)]
+pub struct DenoResolution {
+  pub url: Url,
+  pub maybe_diagnostic: Option<Box<MappedResolutionDiagnostic>>,
+  pub found_package_json_dep: bool,
+}
+
+#[derive(Debug, Error)]
+pub enum DenoResolveErrorKind {
+  #[error("Importing from the vendor directory is not permitted. Use a remote specifier instead or disable vendoring.")]
+  InvalidVendorFolderImport,
+  #[error(transparent)]
+  MappedResolution(#[from] MappedResolutionError),
+  #[error(transparent)]
+  MissingPackageNodeModulesFolder(#[from] MissingPackageNodeModulesFolderError),
+  #[error(transparent)]
+  Node(#[from] NodeResolveError),
+  #[error(transparent)]
+  NodeModulesOutOfDate(#[from] NodeModulesOutOfDateError),
+  #[error(transparent)]
+  PackageJsonDepValueParse(#[from] PackageJsonDepValueParseError),
+  #[error(transparent)]
+  PackageJsonDepValueUrlParse(url::ParseError),
+  #[error(transparent)]
+  PackageSubpathResolve(#[from] PackageSubpathResolveError),
+  #[error(transparent)]
+  ResolvePkgFolderFromDenoReq(#[from] ResolvePkgFolderFromDenoReqError),
+  #[error(transparent)]
+  WorkspaceResolvePkgJsonFolder(#[from] WorkspaceResolvePkgJsonFolderError),
+}
+
+impl DenoResolveErrorKind {
+  pub fn into_box(self) -> DenoResolveError {
+    DenoResolveError(Box::new(self))
+  }
+}
+
+#[derive(Error, Debug)]
+#[error(transparent)]
+pub struct DenoResolveError(pub Box<DenoResolveErrorKind>);
+
+impl DenoResolveError {
+  pub fn as_kind(&self) -> &DenoResolveErrorKind {
+    &self.0
+  }
+
+  pub fn into_kind(self) -> DenoResolveErrorKind {
+    *self.0
+  }
+}
+
+impl<E> From<E> for DenoResolveError
+where
+  DenoResolveErrorKind: From<E>,
+{
+  fn from(err: E) -> Self {
+    DenoResolveError(Box::new(DenoResolveErrorKind::from(err)))
+  }
+}
+
+#[derive(Debug)]
+pub struct NodeAndNpmReqResolver<
+  Fs: DenoResolverFs,
+  TNodeResolverEnv: NodeResolverEnv,
+> {
+  pub node_resolver: Arc<NodeResolver<TNodeResolverEnv>>,
+  pub npm_req_resolver: Arc<NpmReqResolver<Fs, TNodeResolverEnv>>,
+}
+
+pub struct DenoResolverOptions<
+  'a,
+  Fs: DenoResolverFs,
+  TNodeResolverEnv: NodeResolverEnv,
+  TSloppyImportResolverFs: SloppyImportResolverFs,
+> {
+  pub in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+  pub node_and_req_resolver:
+    Option<NodeAndNpmReqResolver<Fs, TNodeResolverEnv>>,
+  pub sloppy_imports_resolver:
+    Option<Arc<SloppyImportsResolver<TSloppyImportResolverFs>>>,
+  pub workspace_resolver: Arc<WorkspaceResolver>,
+  /// Whether "bring your own node_modules" is enabled where Deno does not
+  /// setup the node_modules directories automatically, but instead uses
+  /// what already exists on the file system.
+  pub is_byonm: bool,
+  pub maybe_vendor_dir: Option<&'a PathBuf>,
+}
+
+/// A resolver that takes care of resolution, taking into account loaded
+/// import map, JSX settings.
+#[derive(Debug)]
+pub struct DenoResolver<
+  Fs: DenoResolverFs,
+  TNodeResolverEnv: NodeResolverEnv,
+  TSloppyImportResolverFs: SloppyImportResolverFs,
+> {
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+  node_and_npm_resolver: Option<NodeAndNpmReqResolver<Fs, TNodeResolverEnv>>,
+  sloppy_imports_resolver:
+    Option<Arc<SloppyImportsResolver<TSloppyImportResolverFs>>>,
+  workspace_resolver: Arc<WorkspaceResolver>,
+  is_byonm: bool,
+  maybe_vendor_specifier: Option<Url>,
+}
+
+impl<
+    Fs: DenoResolverFs,
+    TNodeResolverEnv: NodeResolverEnv,
+    TSloppyImportResolverFs: SloppyImportResolverFs,
+  > DenoResolver<Fs, TNodeResolverEnv, TSloppyImportResolverFs>
+{
+  pub fn new(
+    options: DenoResolverOptions<Fs, TNodeResolverEnv, TSloppyImportResolverFs>,
+  ) -> Self {
+    Self {
+      in_npm_pkg_checker: options.in_npm_pkg_checker,
+      node_and_npm_resolver: options.node_and_req_resolver,
+      sloppy_imports_resolver: options.sloppy_imports_resolver,
+      workspace_resolver: options.workspace_resolver,
+      is_byonm: options.is_byonm,
+      maybe_vendor_specifier: options
+        .maybe_vendor_dir
+        .and_then(|v| deno_path_util::url_from_directory_path(v).ok()),
+    }
+  }
+
+  pub fn resolve(
+    &self,
+    raw_specifier: &str,
+    referrer: &Url,
+    referrer_kind: NodeModuleKind,
+    mode: NodeResolutionMode,
+  ) -> Result<DenoResolution, DenoResolveError> {
+    let mut found_package_json_dep = false;
+    let mut maybe_diagnostic = None;
+    // Use node resolution if we're in an npm package
+    if let Some(node_and_npm_resolver) = self.node_and_npm_resolver.as_ref() {
+      let node_resolver = &node_and_npm_resolver.node_resolver;
+      if referrer.scheme() == "file"
+        && self.in_npm_pkg_checker.in_npm_package(referrer)
+      {
+        return node_resolver
+          .resolve(raw_specifier, referrer, referrer_kind, mode)
+          .map(|res| DenoResolution {
+            url: res.into_url(),
+            found_package_json_dep,
+            maybe_diagnostic,
+          })
+          .map_err(|e| e.into());
+      }
+    }
+
+    // Attempt to resolve with the workspace resolver
+    let result: Result<_, DenoResolveError> = self
+      .workspace_resolver
+      .resolve(raw_specifier, referrer)
+      .map_err(|err| err.into());
+    let result = match result {
+      Ok(resolution) => match resolution {
+        MappedResolution::Normal {
+          specifier,
+          maybe_diagnostic: current_diagnostic,
+        }
+        | MappedResolution::ImportMap {
+          specifier,
+          maybe_diagnostic: current_diagnostic,
+        } => {
+          maybe_diagnostic = current_diagnostic;
+          // do sloppy imports resolution if enabled
+          if let Some(sloppy_imports_resolver) = &self.sloppy_imports_resolver {
+            Ok(
+              sloppy_imports_resolver
+                .resolve(
+                  &specifier,
+                  match mode {
+                    NodeResolutionMode::Execution => {
+                      SloppyImportsResolutionMode::Execution
+                    }
+                    NodeResolutionMode::Types => {
+                      SloppyImportsResolutionMode::Types
+                    }
+                  },
+                )
+                .map(|s| s.into_specifier())
+                .unwrap_or(specifier),
+            )
+          } else {
+            Ok(specifier)
+          }
+        }
+        MappedResolution::WorkspaceJsrPackage { specifier, .. } => {
+          Ok(specifier)
+        }
+        MappedResolution::WorkspaceNpmPackage {
+          target_pkg_json: pkg_json,
+          sub_path,
+          ..
+        } => self
+          .node_and_npm_resolver
+          .as_ref()
+          .unwrap()
+          .node_resolver
+          .resolve_package_subpath_from_deno_module(
+            pkg_json.dir_path(),
+            sub_path.as_deref(),
+            Some(referrer),
+            referrer_kind,
+            mode,
+          )
+          .map_err(|e| e.into()),
+        MappedResolution::PackageJson {
+          dep_result,
+          alias,
+          sub_path,
+          ..
+        } => {
+          // found a specifier in the package.json, so mark that
+          // we need to do an "npm install" later
+          found_package_json_dep = true;
+
+          dep_result
+            .as_ref()
+            .map_err(|e| {
+              DenoResolveErrorKind::PackageJsonDepValueParse(e.clone())
+                .into_box()
+            })
+            .and_then(|dep| match dep {
+              // todo(dsherret): it seems bad that we're converting this
+              // to a url because the req might not be a valid url.
+              PackageJsonDepValue::Req(req) => Url::parse(&format!(
+                "npm:{}{}",
+                req,
+                sub_path.map(|s| format!("/{}", s)).unwrap_or_default()
+              ))
+              .map_err(|e| {
+                DenoResolveErrorKind::PackageJsonDepValueUrlParse(e).into_box()
+              }),
+              PackageJsonDepValue::Workspace(version_req) => self
+                .workspace_resolver
+                .resolve_workspace_pkg_json_folder_for_pkg_json_dep(
+                  alias,
+                  version_req,
+                )
+                .map_err(|e| {
+                  DenoResolveErrorKind::WorkspaceResolvePkgJsonFolder(e)
+                    .into_box()
+                })
+                .and_then(|pkg_folder| {
+                  self
+                    .node_and_npm_resolver
+                    .as_ref()
+                    .unwrap()
+                    .node_resolver
+                    .resolve_package_subpath_from_deno_module(
+                      pkg_folder,
+                      sub_path.as_deref(),
+                      Some(referrer),
+                      referrer_kind,
+                      mode,
+                    )
+                    .map_err(|e| {
+                      DenoResolveErrorKind::PackageSubpathResolve(e).into_box()
+                    })
+                }),
+            })
+        }
+      },
+      Err(err) => Err(err),
+    };
+
+    // When the user is vendoring, don't allow them to import directly from the vendor/ directory
+    // as it might cause them confusion or duplicate dependencies. Additionally, this folder has
+    // special treatment in the language server so it will definitely cause issues/confusion there
+    // if they do this.
+    if let Some(vendor_specifier) = &self.maybe_vendor_specifier {
+      if let Ok(specifier) = &result {
+        if specifier.as_str().starts_with(vendor_specifier.as_str()) {
+          return Err(
+            DenoResolveErrorKind::InvalidVendorFolderImport.into_box(),
+          );
+        }
+      }
+    }
+
+    let Some(NodeAndNpmReqResolver {
+      node_resolver,
+      npm_req_resolver,
+    }) = &self.node_and_npm_resolver
+    else {
+      return Ok(DenoResolution {
+        url: result?,
+        maybe_diagnostic,
+        found_package_json_dep,
+      });
+    };
+
+    match result {
+      Ok(specifier) => {
+        if let Ok(npm_req_ref) =
+          NpmPackageReqReference::from_specifier(&specifier)
+        {
+          // check if the npm specifier resolves to a workspace member
+          if let Some(pkg_folder) = self
+            .workspace_resolver
+            .resolve_workspace_pkg_json_folder_for_npm_specifier(
+              npm_req_ref.req(),
+            )
+          {
+            return node_resolver
+              .resolve_package_subpath_from_deno_module(
+                pkg_folder,
+                npm_req_ref.sub_path(),
+                Some(referrer),
+                referrer_kind,
+                mode,
+              )
+              .map(|url| DenoResolution {
+                url,
+                maybe_diagnostic,
+                found_package_json_dep,
+              })
+              .map_err(|e| e.into());
+          }
+
+          // do npm resolution for byonm
+          if self.is_byonm {
+            return npm_req_resolver
+              .resolve_req_reference(
+                &npm_req_ref,
+                referrer,
+                referrer_kind,
+                mode,
+              )
+              .map(|url| DenoResolution {
+                url,
+                maybe_diagnostic,
+                found_package_json_dep,
+              })
+              .map_err(|err| match err {
+                ResolveReqWithSubPathError::MissingPackageNodeModulesFolder(
+                  err,
+                ) => err.into(),
+                ResolveReqWithSubPathError::ResolvePkgFolderFromDenoReq(
+                  err,
+                ) => err.into(),
+                ResolveReqWithSubPathError::PackageSubpathResolve(err) => {
+                  err.into()
+                }
+              });
+          }
+        }
+
+        Ok(DenoResolution {
+          url: node_resolver
+            .handle_if_in_node_modules(&specifier)
+            .unwrap_or(specifier),
+          maybe_diagnostic,
+          found_package_json_dep,
+        })
+      }
+      Err(err) => {
+        // If byonm, check if the bare specifier resolves to an npm package
+        if self.is_byonm && referrer.scheme() == "file" {
+          let maybe_resolution = npm_req_resolver
+            .resolve_if_for_npm_pkg(
+              raw_specifier,
+              referrer,
+              referrer_kind,
+              mode,
+            )
+            .map_err(|e| match e {
+              ResolveIfForNpmPackageError::NodeResolve(e) => {
+                DenoResolveErrorKind::Node(e).into_box()
+              }
+              ResolveIfForNpmPackageError::NodeModulesOutOfDate(e) => e.into(),
+            })?;
+          if let Some(res) = maybe_resolution {
+            match res {
+              NodeResolution::Module(url) => {
+                return Ok(DenoResolution {
+                  url,
+                  maybe_diagnostic,
+                  found_package_json_dep,
+                })
+              }
+              NodeResolution::BuiltIn(_) => {
+                // don't resolve bare specifiers for built-in modules via node resolution
+              }
+            }
+          }
+        }
+
+        Err(err)
+      }
+    }
+  }
+}
diff --git a/resolvers/deno/npm/byonm.rs b/resolvers/deno/npm/byonm.rs
new file mode 100644
index 0000000000..e9182d47a1
--- /dev/null
+++ b/resolvers/deno/npm/byonm.rs
@@ -0,0 +1,398 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+use std::borrow::Cow;
+use std::path::Path;
+use std::path::PathBuf;
+use std::sync::Arc;
+
+use deno_package_json::PackageJson;
+use deno_package_json::PackageJsonDepValue;
+use deno_path_util::url_to_file_path;
+use deno_semver::package::PackageReq;
+use deno_semver::Version;
+use node_resolver::env::NodeResolverEnv;
+use node_resolver::errors::PackageFolderResolveError;
+use node_resolver::errors::PackageFolderResolveIoError;
+use node_resolver::errors::PackageJsonLoadError;
+use node_resolver::errors::PackageNotFoundError;
+use node_resolver::InNpmPackageChecker;
+use node_resolver::NpmPackageFolderResolver;
+use node_resolver::PackageJsonResolverRc;
+use thiserror::Error;
+use url::Url;
+
+use crate::fs::DenoResolverFs;
+
+use super::local::normalize_pkg_name_for_node_modules_deno_folder;
+use super::CliNpmReqResolver;
+use super::ResolvePkgFolderFromDenoReqError;
+
+#[derive(Debug, Error)]
+pub enum ByonmResolvePkgFolderFromDenoReqError {
+  #[error("Could not find \"{}\" in a node_modules folder. Deno expects the node_modules/ directory to be up to date. Did you forget to run `deno install`?", .0)]
+  MissingAlias(String),
+  #[error(transparent)]
+  PackageJson(#[from] PackageJsonLoadError),
+  #[error("Could not find a matching package for 'npm:{}' in the node_modules directory. Ensure you have all your JSR and npm dependencies listed in your deno.json or package.json, then run `deno install`. Alternatively, turn on auto-install by specifying `\"nodeModulesDir\": \"auto\"` in your deno.json file.", .0)]
+  UnmatchedReq(PackageReq),
+  #[error(transparent)]
+  Io(#[from] std::io::Error),
+}
+
+pub struct ByonmNpmResolverCreateOptions<
+  Fs: DenoResolverFs,
+  TEnv: NodeResolverEnv,
+> {
+  // todo(dsherret): investigate removing this
+  pub root_node_modules_dir: Option<PathBuf>,
+  pub fs: Fs,
+  pub pkg_json_resolver: PackageJsonResolverRc<TEnv>,
+}
+
+#[derive(Debug)]
+pub struct ByonmNpmResolver<Fs: DenoResolverFs, TEnv: NodeResolverEnv> {
+  fs: Fs,
+  pkg_json_resolver: PackageJsonResolverRc<TEnv>,
+  root_node_modules_dir: Option<PathBuf>,
+}
+
+impl<Fs: DenoResolverFs + Clone, TEnv: NodeResolverEnv> Clone
+  for ByonmNpmResolver<Fs, TEnv>
+{
+  fn clone(&self) -> Self {
+    Self {
+      fs: self.fs.clone(),
+      pkg_json_resolver: self.pkg_json_resolver.clone(),
+      root_node_modules_dir: self.root_node_modules_dir.clone(),
+    }
+  }
+}
+
+impl<Fs: DenoResolverFs, TEnv: NodeResolverEnv> ByonmNpmResolver<Fs, TEnv> {
+  pub fn new(options: ByonmNpmResolverCreateOptions<Fs, TEnv>) -> Self {
+    Self {
+      root_node_modules_dir: options.root_node_modules_dir,
+      fs: options.fs,
+      pkg_json_resolver: options.pkg_json_resolver,
+    }
+  }
+
+  pub fn root_node_modules_dir(&self) -> Option<&Path> {
+    self.root_node_modules_dir.as_deref()
+  }
+
+  fn load_pkg_json(
+    &self,
+    path: &Path,
+  ) -> Result<Option<Arc<PackageJson>>, PackageJsonLoadError> {
+    self.pkg_json_resolver.load_package_json(path)
+  }
+
+  /// Finds the ancestor package.json that contains the specified dependency.
+  pub fn find_ancestor_package_json_with_dep(
+    &self,
+    dep_name: &str,
+    referrer: &Url,
+  ) -> Option<Arc<PackageJson>> {
+    let referrer_path = url_to_file_path(referrer).ok()?;
+    let mut current_folder = referrer_path.parent()?;
+    loop {
+      let pkg_json_path = current_folder.join("package.json");
+      if let Ok(Some(pkg_json)) = self.load_pkg_json(&pkg_json_path) {
+        if let Some(deps) = &pkg_json.dependencies {
+          if deps.contains_key(dep_name) {
+            return Some(pkg_json);
+          }
+        }
+        if let Some(deps) = &pkg_json.dev_dependencies {
+          if deps.contains_key(dep_name) {
+            return Some(pkg_json);
+          }
+        }
+      }
+
+      if let Some(parent) = current_folder.parent() {
+        current_folder = parent;
+      } else {
+        return None;
+      }
+    }
+  }
+
+  pub fn resolve_pkg_folder_from_deno_module_req(
+    &self,
+    req: &PackageReq,
+    referrer: &Url,
+  ) -> Result<PathBuf, ByonmResolvePkgFolderFromDenoReqError> {
+    fn node_resolve_dir<Fs: DenoResolverFs>(
+      fs: &Fs,
+      alias: &str,
+      start_dir: &Path,
+    ) -> std::io::Result<Option<PathBuf>> {
+      for ancestor in start_dir.ancestors() {
+        let node_modules_folder = ancestor.join("node_modules");
+        let sub_dir = join_package_name(&node_modules_folder, alias);
+        if fs.is_dir_sync(&sub_dir) {
+          return Ok(Some(deno_path_util::canonicalize_path_maybe_not_exists(
+            &sub_dir,
+            &|path| fs.realpath_sync(path),
+          )?));
+        }
+      }
+      Ok(None)
+    }
+
+    // now attempt to resolve if it's found in any package.json
+    let maybe_pkg_json_and_alias =
+      self.resolve_pkg_json_and_alias_for_req(req, referrer)?;
+    match maybe_pkg_json_and_alias {
+      Some((pkg_json, alias)) => {
+        // now try node resolution
+        if let Some(resolved) =
+          node_resolve_dir(&self.fs, &alias, pkg_json.dir_path())?
+        {
+          return Ok(resolved);
+        }
+
+        Err(ByonmResolvePkgFolderFromDenoReqError::MissingAlias(alias))
+      }
+      None => {
+        // now check if node_modules/.deno/ matches this constraint
+        if let Some(folder) = self.resolve_folder_in_root_node_modules(req) {
+          return Ok(folder);
+        }
+
+        Err(ByonmResolvePkgFolderFromDenoReqError::UnmatchedReq(
+          req.clone(),
+        ))
+      }
+    }
+  }
+
+  fn resolve_pkg_json_and_alias_for_req(
+    &self,
+    req: &PackageReq,
+    referrer: &Url,
+  ) -> Result<Option<(Arc<PackageJson>, String)>, PackageJsonLoadError> {
+    fn resolve_alias_from_pkg_json(
+      req: &PackageReq,
+      pkg_json: &PackageJson,
+    ) -> Option<String> {
+      let deps = pkg_json.resolve_local_package_json_deps();
+      for (key, value) in deps {
+        if let Ok(value) = value {
+          match value {
+            PackageJsonDepValue::Req(dep_req) => {
+              if dep_req.name == req.name
+                && dep_req.version_req.intersects(&req.version_req)
+              {
+                return Some(key);
+              }
+            }
+            PackageJsonDepValue::Workspace(_workspace) => {
+              if key == req.name && req.version_req.tag() == Some("workspace") {
+                return Some(key);
+              }
+            }
+          }
+        }
+      }
+      None
+    }
+
+    // attempt to resolve the npm specifier from the referrer's package.json,
+    if let Ok(file_path) = url_to_file_path(referrer) {
+      let mut current_path = file_path.as_path();
+      while let Some(dir_path) = current_path.parent() {
+        let package_json_path = dir_path.join("package.json");
+        if let Some(pkg_json) = self.load_pkg_json(&package_json_path)? {
+          if let Some(alias) =
+            resolve_alias_from_pkg_json(req, pkg_json.as_ref())
+          {
+            return Ok(Some((pkg_json, alias)));
+          }
+        }
+        current_path = dir_path;
+      }
+    }
+
+    // otherwise, fall fallback to the project's package.json
+    if let Some(root_node_modules_dir) = &self.root_node_modules_dir {
+      let root_pkg_json_path =
+        root_node_modules_dir.parent().unwrap().join("package.json");
+      if let Some(pkg_json) = self.load_pkg_json(&root_pkg_json_path)? {
+        if let Some(alias) = resolve_alias_from_pkg_json(req, pkg_json.as_ref())
+        {
+          return Ok(Some((pkg_json, alias)));
+        }
+      }
+    }
+
+    Ok(None)
+  }
+
+  fn resolve_folder_in_root_node_modules(
+    &self,
+    req: &PackageReq,
+  ) -> Option<PathBuf> {
+    // now check if node_modules/.deno/ matches this constraint
+    let root_node_modules_dir = self.root_node_modules_dir.as_ref()?;
+    let node_modules_deno_dir = root_node_modules_dir.join(".deno");
+    let Ok(entries) = self.fs.read_dir_sync(&node_modules_deno_dir) else {
+      return None;
+    };
+    let search_prefix = format!(
+      "{}@",
+      normalize_pkg_name_for_node_modules_deno_folder(&req.name)
+    );
+    let mut best_version = None;
+
+    // example entries:
+    // - @denotest+add@1.0.0
+    // - @denotest+add@1.0.0_1
+    for entry in entries {
+      if !entry.is_directory {
+        continue;
+      }
+      let Some(version_and_copy_idx) = entry.name.strip_prefix(&search_prefix)
+      else {
+        continue;
+      };
+      let version = version_and_copy_idx
+        .rsplit_once('_')
+        .map(|(v, _)| v)
+        .unwrap_or(version_and_copy_idx);
+      let Ok(version) = Version::parse_from_npm(version) else {
+        continue;
+      };
+      if let Some(tag) = req.version_req.tag() {
+        let initialized_file =
+          node_modules_deno_dir.join(&entry.name).join(".initialized");
+        let Ok(contents) = self.fs.read_to_string_lossy(&initialized_file)
+        else {
+          continue;
+        };
+        let mut tags = contents.split(',').map(str::trim);
+        if tags.any(|t| t == tag) {
+          if let Some((best_version_version, _)) = &best_version {
+            if version > *best_version_version {
+              best_version = Some((version, entry.name));
+            }
+          } else {
+            best_version = Some((version, entry.name));
+          }
+        }
+      } else if req.version_req.matches(&version) {
+        if let Some((best_version_version, _)) = &best_version {
+          if version > *best_version_version {
+            best_version = Some((version, entry.name));
+          }
+        } else {
+          best_version = Some((version, entry.name));
+        }
+      }
+    }
+
+    best_version.map(|(_version, entry_name)| {
+      join_package_name(
+        &node_modules_deno_dir.join(entry_name).join("node_modules"),
+        &req.name,
+      )
+    })
+  }
+}
+
+impl<
+    Fs: DenoResolverFs + Send + Sync + std::fmt::Debug,
+    TEnv: NodeResolverEnv,
+  > CliNpmReqResolver for ByonmNpmResolver<Fs, TEnv>
+{
+  fn resolve_pkg_folder_from_deno_module_req(
+    &self,
+    req: &PackageReq,
+    referrer: &Url,
+  ) -> Result<PathBuf, ResolvePkgFolderFromDenoReqError> {
+    ByonmNpmResolver::resolve_pkg_folder_from_deno_module_req(
+      self, req, referrer,
+    )
+    .map_err(ResolvePkgFolderFromDenoReqError::Byonm)
+  }
+}
+
+impl<
+    Fs: DenoResolverFs + Send + Sync + std::fmt::Debug,
+    TEnv: NodeResolverEnv,
+  > NpmPackageFolderResolver for ByonmNpmResolver<Fs, TEnv>
+{
+  fn resolve_package_folder_from_package(
+    &self,
+    name: &str,
+    referrer: &Url,
+  ) -> Result<PathBuf, PackageFolderResolveError> {
+    fn inner<Fs: DenoResolverFs>(
+      fs: &Fs,
+      name: &str,
+      referrer: &Url,
+    ) -> Result<PathBuf, PackageFolderResolveError> {
+      let maybe_referrer_file = url_to_file_path(referrer).ok();
+      let maybe_start_folder =
+        maybe_referrer_file.as_ref().and_then(|f| f.parent());
+      if let Some(start_folder) = maybe_start_folder {
+        for current_folder in start_folder.ancestors() {
+          let node_modules_folder = if current_folder.ends_with("node_modules")
+          {
+            Cow::Borrowed(current_folder)
+          } else {
+            Cow::Owned(current_folder.join("node_modules"))
+          };
+
+          let sub_dir = join_package_name(&node_modules_folder, name);
+          if fs.is_dir_sync(&sub_dir) {
+            return Ok(sub_dir);
+          }
+        }
+      }
+
+      Err(
+        PackageNotFoundError {
+          package_name: name.to_string(),
+          referrer: referrer.clone(),
+          referrer_extra: None,
+        }
+        .into(),
+      )
+    }
+
+    let path = inner(&self.fs, name, referrer)?;
+    self.fs.realpath_sync(&path).map_err(|err| {
+      PackageFolderResolveIoError {
+        package_name: name.to_string(),
+        referrer: referrer.clone(),
+        source: err,
+      }
+      .into()
+    })
+  }
+}
+
+#[derive(Debug)]
+pub struct ByonmInNpmPackageChecker;
+
+impl InNpmPackageChecker for ByonmInNpmPackageChecker {
+  fn in_npm_package(&self, specifier: &Url) -> bool {
+    specifier.scheme() == "file"
+      && specifier
+        .path()
+        .to_ascii_lowercase()
+        .contains("/node_modules/")
+  }
+}
+
+fn join_package_name(path: &Path, package_name: &str) -> PathBuf {
+  let mut path = path.to_path_buf();
+  // ensure backslashes are used on windows
+  for part in package_name.split('/') {
+    path = path.join(part);
+  }
+  path
+}
diff --git a/resolvers/deno/npm/local.rs b/resolvers/deno/npm/local.rs
new file mode 100644
index 0000000000..aef476ad94
--- /dev/null
+++ b/resolvers/deno/npm/local.rs
@@ -0,0 +1,27 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+use std::borrow::Cow;
+
+/// Normalizes a package name for use at `node_modules/.deno/<pkg-name>@<version>[_<copy_index>]`
+pub fn normalize_pkg_name_for_node_modules_deno_folder(name: &str) -> Cow<str> {
+  let name = if name.to_lowercase() == name {
+    Cow::Borrowed(name)
+  } else {
+    Cow::Owned(format!("_{}", mixed_case_package_name_encode(name)))
+  };
+  if name.starts_with('@') {
+    name.replace('/', "+").into()
+  } else {
+    name
+  }
+}
+
+fn mixed_case_package_name_encode(name: &str) -> String {
+  // use base32 encoding because it's reversible and the character set
+  // only includes the characters within 0-9 and A-Z so it can be lower cased
+  base32::encode(
+    base32::Alphabet::Rfc4648Lower { padding: false },
+    name.as_bytes(),
+  )
+  .to_lowercase()
+}
diff --git a/resolvers/deno/npm/mod.rs b/resolvers/deno/npm/mod.rs
new file mode 100644
index 0000000000..b0aec71b08
--- /dev/null
+++ b/resolvers/deno/npm/mod.rs
@@ -0,0 +1,256 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+use std::fmt::Debug;
+use std::path::PathBuf;
+use std::sync::Arc;
+
+use deno_semver::npm::NpmPackageReqReference;
+use deno_semver::package::PackageReq;
+use node_resolver::env::NodeResolverEnv;
+use node_resolver::errors::NodeResolveError;
+use node_resolver::errors::NodeResolveErrorKind;
+use node_resolver::errors::PackageFolderResolveErrorKind;
+use node_resolver::errors::PackageFolderResolveIoError;
+use node_resolver::errors::PackageNotFoundError;
+use node_resolver::errors::PackageResolveErrorKind;
+use node_resolver::errors::PackageSubpathResolveError;
+use node_resolver::InNpmPackageChecker;
+use node_resolver::NodeModuleKind;
+use node_resolver::NodeResolution;
+use node_resolver::NodeResolutionMode;
+use node_resolver::NodeResolver;
+use thiserror::Error;
+use url::Url;
+
+use crate::fs::DenoResolverFs;
+
+pub use byonm::ByonmInNpmPackageChecker;
+pub use byonm::ByonmNpmResolver;
+pub use byonm::ByonmNpmResolverCreateOptions;
+pub use byonm::ByonmResolvePkgFolderFromDenoReqError;
+pub use local::normalize_pkg_name_for_node_modules_deno_folder;
+
+mod byonm;
+mod local;
+
+#[derive(Debug, Error)]
+#[error("Could not resolve \"{}\", but found it in a package.json. Deno expects the node_modules/ directory to be up to date. Did you forget to run `deno install`?", specifier)]
+pub struct NodeModulesOutOfDateError {
+  pub specifier: String,
+}
+
+#[derive(Debug, Error)]
+#[error("Could not find '{}'. Deno expects the node_modules/ directory to be up to date. Did you forget to run `deno install`?", package_json_path.display())]
+pub struct MissingPackageNodeModulesFolderError {
+  pub package_json_path: PathBuf,
+}
+
+#[derive(Debug, Error)]
+pub enum ResolveIfForNpmPackageError {
+  #[error(transparent)]
+  NodeResolve(#[from] NodeResolveError),
+  #[error(transparent)]
+  NodeModulesOutOfDate(#[from] NodeModulesOutOfDateError),
+}
+
+#[derive(Debug, Error)]
+pub enum ResolveReqWithSubPathError {
+  #[error(transparent)]
+  MissingPackageNodeModulesFolder(#[from] MissingPackageNodeModulesFolderError),
+  #[error(transparent)]
+  ResolvePkgFolderFromDenoReq(#[from] ResolvePkgFolderFromDenoReqError),
+  #[error(transparent)]
+  PackageSubpathResolve(#[from] PackageSubpathResolveError),
+}
+
+#[derive(Debug, Error)]
+pub enum ResolvePkgFolderFromDenoReqError {
+  // todo(dsherret): don't use anyhow here
+  #[error(transparent)]
+  Managed(anyhow::Error),
+  #[error(transparent)]
+  Byonm(#[from] ByonmResolvePkgFolderFromDenoReqError),
+}
+
+// todo(dsherret): a temporary trait until we extract
+// out the CLI npm resolver into here
+pub trait CliNpmReqResolver: Debug + Send + Sync {
+  fn resolve_pkg_folder_from_deno_module_req(
+    &self,
+    req: &PackageReq,
+    referrer: &Url,
+  ) -> Result<PathBuf, ResolvePkgFolderFromDenoReqError>;
+}
+
+pub struct NpmReqResolverOptions<
+  Fs: DenoResolverFs,
+  TNodeResolverEnv: NodeResolverEnv,
+> {
+  /// The resolver when "bring your own node_modules" is enabled where Deno
+  /// does not setup the node_modules directories automatically, but instead
+  /// uses what already exists on the file system.
+  pub byonm_resolver: Option<Arc<ByonmNpmResolver<Fs, TNodeResolverEnv>>>,
+  pub fs: Fs,
+  pub in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+  pub node_resolver: Arc<NodeResolver<TNodeResolverEnv>>,
+  pub npm_req_resolver: Arc<dyn CliNpmReqResolver>,
+}
+
+#[derive(Debug)]
+pub struct NpmReqResolver<Fs: DenoResolverFs, TNodeResolverEnv: NodeResolverEnv>
+{
+  byonm_resolver: Option<Arc<ByonmNpmResolver<Fs, TNodeResolverEnv>>>,
+  fs: Fs,
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+  node_resolver: Arc<NodeResolver<TNodeResolverEnv>>,
+  npm_resolver: Arc<dyn CliNpmReqResolver>,
+}
+
+impl<Fs: DenoResolverFs, TNodeResolverEnv: NodeResolverEnv>
+  NpmReqResolver<Fs, TNodeResolverEnv>
+{
+  pub fn new(options: NpmReqResolverOptions<Fs, TNodeResolverEnv>) -> Self {
+    Self {
+      byonm_resolver: options.byonm_resolver,
+      fs: options.fs,
+      in_npm_pkg_checker: options.in_npm_pkg_checker,
+      node_resolver: options.node_resolver,
+      npm_resolver: options.npm_req_resolver,
+    }
+  }
+
+  pub fn resolve_req_reference(
+    &self,
+    req_ref: &NpmPackageReqReference,
+    referrer: &Url,
+    referrer_kind: NodeModuleKind,
+    mode: NodeResolutionMode,
+  ) -> Result<Url, ResolveReqWithSubPathError> {
+    self.resolve_req_with_sub_path(
+      req_ref.req(),
+      req_ref.sub_path(),
+      referrer,
+      referrer_kind,
+      mode,
+    )
+  }
+
+  pub fn resolve_req_with_sub_path(
+    &self,
+    req: &PackageReq,
+    sub_path: Option<&str>,
+    referrer: &Url,
+    referrer_kind: NodeModuleKind,
+    mode: NodeResolutionMode,
+  ) -> Result<Url, ResolveReqWithSubPathError> {
+    let package_folder = self
+      .npm_resolver
+      .resolve_pkg_folder_from_deno_module_req(req, referrer)?;
+    let resolution_result =
+      self.node_resolver.resolve_package_subpath_from_deno_module(
+        &package_folder,
+        sub_path,
+        Some(referrer),
+        referrer_kind,
+        mode,
+      );
+    match resolution_result {
+      Ok(url) => Ok(url),
+      Err(err) => {
+        if self.byonm_resolver.is_some() {
+          let package_json_path = package_folder.join("package.json");
+          if !self.fs.exists_sync(&package_json_path) {
+            return Err(
+              MissingPackageNodeModulesFolderError { package_json_path }.into(),
+            );
+          }
+        }
+        Err(err.into())
+      }
+    }
+  }
+
+  pub fn resolve_if_for_npm_pkg(
+    &self,
+    specifier: &str,
+    referrer: &Url,
+    referrer_kind: NodeModuleKind,
+    mode: NodeResolutionMode,
+  ) -> Result<Option<NodeResolution>, ResolveIfForNpmPackageError> {
+    let resolution_result =
+      self
+        .node_resolver
+        .resolve(specifier, referrer, referrer_kind, mode);
+    match resolution_result {
+      Ok(res) => Ok(Some(res)),
+      Err(err) => {
+        let err = err.into_kind();
+        match err {
+          NodeResolveErrorKind::RelativeJoin(_)
+          | NodeResolveErrorKind::PackageImportsResolve(_)
+          | NodeResolveErrorKind::UnsupportedEsmUrlScheme(_)
+          | NodeResolveErrorKind::DataUrlReferrer(_)
+          | NodeResolveErrorKind::TypesNotFound(_)
+          | NodeResolveErrorKind::FinalizeResolution(_) => {
+            Err(ResolveIfForNpmPackageError::NodeResolve(err.into()))
+          }
+          NodeResolveErrorKind::PackageResolve(err) => {
+            let err = err.into_kind();
+            match err {
+              PackageResolveErrorKind::ClosestPkgJson(_)
+              | PackageResolveErrorKind::InvalidModuleSpecifier(_)
+              | PackageResolveErrorKind::ExportsResolve(_)
+              | PackageResolveErrorKind::SubpathResolve(_) => {
+                Err(ResolveIfForNpmPackageError::NodeResolve(
+                  NodeResolveErrorKind::PackageResolve(err.into()).into(),
+                ))
+              }
+              PackageResolveErrorKind::PackageFolderResolve(err) => {
+                match err.as_kind() {
+                  PackageFolderResolveErrorKind::Io(
+                    PackageFolderResolveIoError { package_name, .. },
+                  )
+                  | PackageFolderResolveErrorKind::PackageNotFound(
+                    PackageNotFoundError { package_name, .. },
+                  ) => {
+                    if self.in_npm_pkg_checker.in_npm_package(referrer) {
+                      return Err(ResolveIfForNpmPackageError::NodeResolve(
+                        NodeResolveErrorKind::PackageResolve(err.into()).into(),
+                      ));
+                    }
+                    if let Some(byonm_npm_resolver) = &self.byonm_resolver {
+                      if byonm_npm_resolver
+                        .find_ancestor_package_json_with_dep(
+                          package_name,
+                          referrer,
+                        )
+                        .is_some()
+                      {
+                        return Err(
+                          ResolveIfForNpmPackageError::NodeModulesOutOfDate(
+                            NodeModulesOutOfDateError {
+                              specifier: specifier.to_string(),
+                            },
+                          ),
+                        );
+                      }
+                    }
+                    Ok(None)
+                  }
+                  PackageFolderResolveErrorKind::ReferrerNotFound(_) => {
+                    if self.in_npm_pkg_checker.in_npm_package(referrer) {
+                      return Err(ResolveIfForNpmPackageError::NodeResolve(
+                        NodeResolveErrorKind::PackageResolve(err.into()).into(),
+                      ));
+                    }
+                    Ok(None)
+                  }
+                }
+              }
+            }
+          }
+        }
+      }
+    }
+  }
+}
diff --git a/resolvers/deno/sloppy_imports.rs b/resolvers/deno/sloppy_imports.rs
new file mode 100644
index 0000000000..7aba5b771a
--- /dev/null
+++ b/resolvers/deno/sloppy_imports.rs
@@ -0,0 +1,513 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+use std::borrow::Cow;
+use std::path::Path;
+use std::path::PathBuf;
+
+use deno_media_type::MediaType;
+use deno_path_util::url_from_file_path;
+use deno_path_util::url_to_file_path;
+use url::Url;
+
+#[derive(Debug, Clone, Copy, PartialEq, Eq)]
+pub enum SloppyImportsFsEntry {
+  File,
+  Dir,
+}
+
+#[derive(Debug, Clone, PartialEq, Eq)]
+pub enum SloppyImportsResolution {
+  /// Ex. `./file.js` to `./file.ts`
+  JsToTs(Url),
+  /// Ex. `./file` to `./file.ts`
+  NoExtension(Url),
+  /// Ex. `./dir` to `./dir/index.ts`
+  Directory(Url),
+}
+
+impl SloppyImportsResolution {
+  pub fn as_specifier(&self) -> &Url {
+    match self {
+      Self::JsToTs(specifier) => specifier,
+      Self::NoExtension(specifier) => specifier,
+      Self::Directory(specifier) => specifier,
+    }
+  }
+
+  pub fn into_specifier(self) -> Url {
+    match self {
+      Self::JsToTs(specifier) => specifier,
+      Self::NoExtension(specifier) => specifier,
+      Self::Directory(specifier) => specifier,
+    }
+  }
+
+  pub fn as_suggestion_message(&self) -> String {
+    format!("Maybe {}", self.as_base_message())
+  }
+
+  pub fn as_quick_fix_message(&self) -> String {
+    let message = self.as_base_message();
+    let mut chars = message.chars();
+    format!(
+      "{}{}.",
+      chars.next().unwrap().to_uppercase(),
+      chars.as_str()
+    )
+  }
+
+  fn as_base_message(&self) -> String {
+    match self {
+      SloppyImportsResolution::JsToTs(specifier) => {
+        let media_type = MediaType::from_specifier(specifier);
+        format!("change the extension to '{}'", media_type.as_ts_extension())
+      }
+      SloppyImportsResolution::NoExtension(specifier) => {
+        let media_type = MediaType::from_specifier(specifier);
+        format!("add a '{}' extension", media_type.as_ts_extension())
+      }
+      SloppyImportsResolution::Directory(specifier) => {
+        let file_name = specifier
+          .path()
+          .rsplit_once('/')
+          .map(|(_, file_name)| file_name)
+          .unwrap_or(specifier.path());
+        format!("specify path to '{}' file in directory instead", file_name)
+      }
+    }
+  }
+}
+
+/// The kind of resolution currently being done.
+#[derive(Debug, Clone, Copy, PartialEq, Eq)]
+pub enum SloppyImportsResolutionMode {
+  /// Resolving for code that will be executed.
+  Execution,
+  /// Resolving for code that will be used for type information.
+  Types,
+}
+
+impl SloppyImportsResolutionMode {
+  pub fn is_types(&self) -> bool {
+    *self == SloppyImportsResolutionMode::Types
+  }
+}
+
+pub trait SloppyImportResolverFs {
+  fn stat_sync(&self, path: &Path) -> Option<SloppyImportsFsEntry>;
+
+  fn is_file(&self, path: &Path) -> bool {
+    self.stat_sync(path) == Some(SloppyImportsFsEntry::File)
+  }
+}
+
+#[derive(Debug)]
+pub struct SloppyImportsResolver<Fs: SloppyImportResolverFs> {
+  fs: Fs,
+}
+
+impl<Fs: SloppyImportResolverFs> SloppyImportsResolver<Fs> {
+  pub fn new(fs: Fs) -> Self {
+    Self { fs }
+  }
+
+  pub fn resolve(
+    &self,
+    specifier: &Url,
+    mode: SloppyImportsResolutionMode,
+  ) -> Option<SloppyImportsResolution> {
+    fn path_without_ext(
+      path: &Path,
+      media_type: MediaType,
+    ) -> Option<Cow<str>> {
+      let old_path_str = path.to_string_lossy();
+      match media_type {
+        MediaType::Unknown => Some(old_path_str),
+        _ => old_path_str
+          .strip_suffix(media_type.as_ts_extension())
+          .map(|s| Cow::Owned(s.to_string())),
+      }
+    }
+
+    fn media_types_to_paths(
+      path_no_ext: &str,
+      original_media_type: MediaType,
+      probe_media_type_types: Vec<MediaType>,
+      reason: SloppyImportsResolutionReason,
+    ) -> Vec<(PathBuf, SloppyImportsResolutionReason)> {
+      probe_media_type_types
+        .into_iter()
+        .filter(|media_type| *media_type != original_media_type)
+        .map(|media_type| {
+          (
+            PathBuf::from(format!(
+              "{}{}",
+              path_no_ext,
+              media_type.as_ts_extension()
+            )),
+            reason,
+          )
+        })
+        .collect::<Vec<_>>()
+    }
+
+    if specifier.scheme() != "file" {
+      return None;
+    }
+
+    let path = url_to_file_path(specifier).ok()?;
+
+    #[derive(Clone, Copy)]
+    enum SloppyImportsResolutionReason {
+      JsToTs,
+      NoExtension,
+      Directory,
+    }
+
+    let probe_paths: Vec<(PathBuf, SloppyImportsResolutionReason)> =
+      match self.fs.stat_sync(&path) {
+        Some(SloppyImportsFsEntry::File) => {
+          if mode.is_types() {
+            let media_type = MediaType::from_specifier(specifier);
+            // attempt to resolve the .d.ts file before the .js file
+            let probe_media_type_types = match media_type {
+              MediaType::JavaScript => {
+                vec![(MediaType::Dts), MediaType::JavaScript]
+              }
+              MediaType::Mjs => {
+                vec![MediaType::Dmts, MediaType::Dts, MediaType::Mjs]
+              }
+              MediaType::Cjs => {
+                vec![MediaType::Dcts, MediaType::Dts, MediaType::Cjs]
+              }
+              _ => return None,
+            };
+            let path_no_ext = path_without_ext(&path, media_type)?;
+            media_types_to_paths(
+              &path_no_ext,
+              media_type,
+              probe_media_type_types,
+              SloppyImportsResolutionReason::JsToTs,
+            )
+          } else {
+            return None;
+          }
+        }
+        entry @ None | entry @ Some(SloppyImportsFsEntry::Dir) => {
+          let media_type = MediaType::from_specifier(specifier);
+          let probe_media_type_types = match media_type {
+            MediaType::JavaScript => (
+              if mode.is_types() {
+                vec![MediaType::TypeScript, MediaType::Tsx, MediaType::Dts]
+              } else {
+                vec![MediaType::TypeScript, MediaType::Tsx]
+              },
+              SloppyImportsResolutionReason::JsToTs,
+            ),
+            MediaType::Jsx => {
+              (vec![MediaType::Tsx], SloppyImportsResolutionReason::JsToTs)
+            }
+            MediaType::Mjs => (
+              if mode.is_types() {
+                vec![MediaType::Mts, MediaType::Dmts, MediaType::Dts]
+              } else {
+                vec![MediaType::Mts]
+              },
+              SloppyImportsResolutionReason::JsToTs,
+            ),
+            MediaType::Cjs => (
+              if mode.is_types() {
+                vec![MediaType::Cts, MediaType::Dcts, MediaType::Dts]
+              } else {
+                vec![MediaType::Cts]
+              },
+              SloppyImportsResolutionReason::JsToTs,
+            ),
+            MediaType::TypeScript
+            | MediaType::Mts
+            | MediaType::Cts
+            | MediaType::Dts
+            | MediaType::Dmts
+            | MediaType::Dcts
+            | MediaType::Tsx
+            | MediaType::Json
+            | MediaType::Wasm
+            | MediaType::Css
+            | MediaType::SourceMap => {
+              return None;
+            }
+            MediaType::Unknown => (
+              if mode.is_types() {
+                vec![
+                  MediaType::TypeScript,
+                  MediaType::Tsx,
+                  MediaType::Mts,
+                  MediaType::Dts,
+                  MediaType::Dmts,
+                  MediaType::Dcts,
+                  MediaType::JavaScript,
+                  MediaType::Jsx,
+                  MediaType::Mjs,
+                ]
+              } else {
+                vec![
+                  MediaType::TypeScript,
+                  MediaType::JavaScript,
+                  MediaType::Tsx,
+                  MediaType::Jsx,
+                  MediaType::Mts,
+                  MediaType::Mjs,
+                ]
+              },
+              SloppyImportsResolutionReason::NoExtension,
+            ),
+          };
+          let mut probe_paths = match path_without_ext(&path, media_type) {
+            Some(path_no_ext) => media_types_to_paths(
+              &path_no_ext,
+              media_type,
+              probe_media_type_types.0,
+              probe_media_type_types.1,
+            ),
+            None => vec![],
+          };
+
+          if matches!(entry, Some(SloppyImportsFsEntry::Dir)) {
+            // try to resolve at the index file
+            if mode.is_types() {
+              probe_paths.push((
+                path.join("index.ts"),
+                SloppyImportsResolutionReason::Directory,
+              ));
+
+              probe_paths.push((
+                path.join("index.mts"),
+                SloppyImportsResolutionReason::Directory,
+              ));
+              probe_paths.push((
+                path.join("index.d.ts"),
+                SloppyImportsResolutionReason::Directory,
+              ));
+              probe_paths.push((
+                path.join("index.d.mts"),
+                SloppyImportsResolutionReason::Directory,
+              ));
+              probe_paths.push((
+                path.join("index.js"),
+                SloppyImportsResolutionReason::Directory,
+              ));
+              probe_paths.push((
+                path.join("index.mjs"),
+                SloppyImportsResolutionReason::Directory,
+              ));
+              probe_paths.push((
+                path.join("index.tsx"),
+                SloppyImportsResolutionReason::Directory,
+              ));
+              probe_paths.push((
+                path.join("index.jsx"),
+                SloppyImportsResolutionReason::Directory,
+              ));
+            } else {
+              probe_paths.push((
+                path.join("index.ts"),
+                SloppyImportsResolutionReason::Directory,
+              ));
+              probe_paths.push((
+                path.join("index.mts"),
+                SloppyImportsResolutionReason::Directory,
+              ));
+              probe_paths.push((
+                path.join("index.tsx"),
+                SloppyImportsResolutionReason::Directory,
+              ));
+              probe_paths.push((
+                path.join("index.js"),
+                SloppyImportsResolutionReason::Directory,
+              ));
+              probe_paths.push((
+                path.join("index.mjs"),
+                SloppyImportsResolutionReason::Directory,
+              ));
+              probe_paths.push((
+                path.join("index.jsx"),
+                SloppyImportsResolutionReason::Directory,
+              ));
+            }
+          }
+          if probe_paths.is_empty() {
+            return None;
+          }
+          probe_paths
+        }
+      };
+
+    for (probe_path, reason) in probe_paths {
+      if self.fs.is_file(&probe_path) {
+        if let Ok(specifier) = url_from_file_path(&probe_path) {
+          match reason {
+            SloppyImportsResolutionReason::JsToTs => {
+              return Some(SloppyImportsResolution::JsToTs(specifier));
+            }
+            SloppyImportsResolutionReason::NoExtension => {
+              return Some(SloppyImportsResolution::NoExtension(specifier));
+            }
+            SloppyImportsResolutionReason::Directory => {
+              return Some(SloppyImportsResolution::Directory(specifier));
+            }
+          }
+        }
+      }
+    }
+
+    None
+  }
+}
+
+#[cfg(test)]
+mod test {
+  use test_util::TestContext;
+
+  use super::*;
+
+  #[test]
+  fn test_unstable_sloppy_imports() {
+    fn resolve(specifier: &Url) -> Option<SloppyImportsResolution> {
+      resolve_with_mode(specifier, SloppyImportsResolutionMode::Execution)
+    }
+
+    fn resolve_types(specifier: &Url) -> Option<SloppyImportsResolution> {
+      resolve_with_mode(specifier, SloppyImportsResolutionMode::Types)
+    }
+
+    fn resolve_with_mode(
+      specifier: &Url,
+      mode: SloppyImportsResolutionMode,
+    ) -> Option<SloppyImportsResolution> {
+      struct RealSloppyImportsResolverFs;
+      impl SloppyImportResolverFs for RealSloppyImportsResolverFs {
+        fn stat_sync(&self, path: &Path) -> Option<SloppyImportsFsEntry> {
+          #[allow(clippy::disallowed_methods)]
+          let stat = std::fs::metadata(path).ok()?;
+          if stat.is_dir() {
+            Some(SloppyImportsFsEntry::Dir)
+          } else if stat.is_file() {
+            Some(SloppyImportsFsEntry::File)
+          } else {
+            None
+          }
+        }
+      }
+
+      SloppyImportsResolver::new(RealSloppyImportsResolverFs)
+        .resolve(specifier, mode)
+    }
+
+    let context = TestContext::default();
+    let temp_dir = context.temp_dir().path();
+
+    // scenarios like resolving ./example.js to ./example.ts
+    for (ext_from, ext_to) in [("js", "ts"), ("js", "tsx"), ("mjs", "mts")] {
+      let ts_file = temp_dir.join(format!("file.{}", ext_to));
+      ts_file.write("");
+      assert_eq!(resolve(&ts_file.url_file()), None);
+      assert_eq!(
+        resolve(
+          &temp_dir
+            .url_dir()
+            .join(&format!("file.{}", ext_from))
+            .unwrap()
+        ),
+        Some(SloppyImportsResolution::JsToTs(ts_file.url_file())),
+      );
+      ts_file.remove_file();
+    }
+
+    // no extension scenarios
+    for ext in ["js", "ts", "js", "tsx", "jsx", "mjs", "mts"] {
+      let file = temp_dir.join(format!("file.{}", ext));
+      file.write("");
+      assert_eq!(
+        resolve(
+          &temp_dir
+            .url_dir()
+            .join("file") // no ext
+            .unwrap()
+        ),
+        Some(SloppyImportsResolution::NoExtension(file.url_file()))
+      );
+      file.remove_file();
+    }
+
+    // .ts and .js exists, .js specified (goes to specified)
+    {
+      let ts_file = temp_dir.join("file.ts");
+      ts_file.write("");
+      let js_file = temp_dir.join("file.js");
+      js_file.write("");
+      assert_eq!(resolve(&js_file.url_file()), None);
+    }
+
+    // only js exists, .js specified
+    {
+      let js_only_file = temp_dir.join("js_only.js");
+      js_only_file.write("");
+      assert_eq!(resolve(&js_only_file.url_file()), None);
+      assert_eq!(resolve_types(&js_only_file.url_file()), None);
+    }
+
+    // resolving a directory to an index file
+    {
+      let routes_dir = temp_dir.join("routes");
+      routes_dir.create_dir_all();
+      let index_file = routes_dir.join("index.ts");
+      index_file.write("");
+      assert_eq!(
+        resolve(&routes_dir.url_file()),
+        Some(SloppyImportsResolution::Directory(index_file.url_file())),
+      );
+    }
+
+    // both a directory and a file with specifier is present
+    {
+      let api_dir = temp_dir.join("api");
+      api_dir.create_dir_all();
+      let bar_file = api_dir.join("bar.ts");
+      bar_file.write("");
+      let api_file = temp_dir.join("api.ts");
+      api_file.write("");
+      assert_eq!(
+        resolve(&api_dir.url_file()),
+        Some(SloppyImportsResolution::NoExtension(api_file.url_file())),
+      );
+    }
+  }
+
+  #[test]
+  fn test_sloppy_import_resolution_suggestion_message() {
+    // directory
+    assert_eq!(
+      SloppyImportsResolution::Directory(
+        Url::parse("file:///dir/index.js").unwrap()
+      )
+      .as_suggestion_message(),
+      "Maybe specify path to 'index.js' file in directory instead"
+    );
+    // no ext
+    assert_eq!(
+      SloppyImportsResolution::NoExtension(
+        Url::parse("file:///dir/index.mjs").unwrap()
+      )
+      .as_suggestion_message(),
+      "Maybe add a '.mjs' extension"
+    );
+    // js to ts
+    assert_eq!(
+      SloppyImportsResolution::JsToTs(
+        Url::parse("file:///dir/index.mts").unwrap()
+      )
+      .as_suggestion_message(),
+      "Maybe change the extension to '.mts'"
+    );
+  }
+}
diff --git a/ext/node_resolver/Cargo.toml b/resolvers/node/Cargo.toml
similarity index 93%
rename from ext/node_resolver/Cargo.toml
rename to resolvers/node/Cargo.toml
index 1042045692..6c2407ad9f 100644
--- a/ext/node_resolver/Cargo.toml
+++ b/resolvers/node/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "node_resolver"
-version = "0.7.0"
+version = "0.16.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -21,6 +21,7 @@ anyhow.workspace = true
 async-trait.workspace = true
 deno_media_type.workspace = true
 deno_package_json.workspace = true
+deno_path_util.workspace = true
 futures.workspace = true
 lazy-regex.workspace = true
 once_cell.workspace = true
diff --git a/ext/node_resolver/README.md b/resolvers/node/README.md
similarity index 100%
rename from ext/node_resolver/README.md
rename to resolvers/node/README.md
diff --git a/ext/node_resolver/analyze.rs b/resolvers/node/analyze.rs
similarity index 87%
rename from ext/node_resolver/analyze.rs
rename to resolvers/node/analyze.rs
index deb56d064e..9126890805 100644
--- a/ext/node_resolver/analyze.rs
+++ b/resolvers/node/analyze.rs
@@ -6,6 +6,8 @@ use std::collections::HashSet;
 use std::path::Path;
 use std::path::PathBuf;
 
+use deno_path_util::url_from_file_path;
+use deno_path_util::url_to_file_path;
 use futures::future::LocalBoxFuture;
 use futures::stream::FuturesUnordered;
 use futures::FutureExt;
@@ -17,19 +19,19 @@ use anyhow::Error as AnyError;
 use url::Url;
 
 use crate::env::NodeResolverEnv;
-use crate::package_json::load_pkg_json;
-use crate::path::to_file_specifier;
+use crate::npm::InNpmPackageCheckerRc;
 use crate::resolution::NodeResolverRc;
 use crate::NodeModuleKind;
 use crate::NodeResolutionMode;
-use crate::NpmResolverRc;
+use crate::NpmPackageFolderResolverRc;
+use crate::PackageJsonResolverRc;
 use crate::PathClean;
 
 #[derive(Debug, Clone)]
-pub enum CjsAnalysis {
+pub enum CjsAnalysis<'a> {
   /// File was found to be an ES module and the translator should
   /// load the code as ESM.
-  Esm(String),
+  Esm(Cow<'a, str>),
   Cjs(CjsAnalysisExports),
 }
 
@@ -49,11 +51,11 @@ pub trait CjsCodeAnalyzer {
   /// already has it. If the source is needed by the implementation,
   /// then it can use the provided source, or otherwise load it if
   /// necessary.
-  async fn analyze_cjs(
+  async fn analyze_cjs<'a>(
     &self,
     specifier: &Url,
-    maybe_source: Option<String>,
-  ) -> Result<CjsAnalysis, AnyError>;
+    maybe_source: Option<Cow<'a, str>>,
+  ) -> Result<CjsAnalysis<'a>, AnyError>;
 }
 
 pub struct NodeCodeTranslator<
@@ -62,8 +64,10 @@ pub struct NodeCodeTranslator<
 > {
   cjs_code_analyzer: TCjsCodeAnalyzer,
   env: TNodeResolverEnv,
+  in_npm_pkg_checker: InNpmPackageCheckerRc,
   node_resolver: NodeResolverRc<TNodeResolverEnv>,
-  npm_resolver: NpmResolverRc,
+  npm_resolver: NpmPackageFolderResolverRc,
+  pkg_json_resolver: PackageJsonResolverRc<TNodeResolverEnv>,
 }
 
 impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
@@ -72,14 +76,18 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
   pub fn new(
     cjs_code_analyzer: TCjsCodeAnalyzer,
     env: TNodeResolverEnv,
+    in_npm_pkg_checker: InNpmPackageCheckerRc,
     node_resolver: NodeResolverRc<TNodeResolverEnv>,
-    npm_resolver: NpmResolverRc,
+    npm_resolver: NpmPackageFolderResolverRc,
+    pkg_json_resolver: PackageJsonResolverRc<TNodeResolverEnv>,
   ) -> Self {
     Self {
       cjs_code_analyzer,
       env,
+      in_npm_pkg_checker,
       node_resolver,
       npm_resolver,
+      pkg_json_resolver,
     }
   }
 
@@ -89,11 +97,11 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
   /// For all discovered reexports the analysis will be performed recursively.
   ///
   /// If successful a source code for equivalent ES module is returned.
-  pub async fn translate_cjs_to_esm(
+  pub async fn translate_cjs_to_esm<'a>(
     &self,
     entry_specifier: &Url,
-    source: Option<String>,
-  ) -> Result<String, AnyError> {
+    source: Option<Cow<'a, str>>,
+  ) -> Result<Cow<'a, str>, AnyError> {
     let mut temp_var_count = 0;
 
     let analysis = self
@@ -107,7 +115,7 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
     };
 
     let mut source = vec![
-      r#"import {createRequire as __internalCreateRequire} from "node:module";
+      r#"import {createRequire as __internalCreateRequire, Module as __internalModule } from "node:module";
       const require = __internalCreateRequire(import.meta.url);"#
         .to_string(),
     ];
@@ -134,9 +142,13 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
     }
 
     source.push(format!(
-      "const mod = require(\"{}\");",
-      entry_specifier
-        .to_file_path()
+      r#"let mod;
+      if (import.meta.main) {{
+        mod = __internalModule._load("{0}", null, true)
+      }} else {{
+        mod = require("{0}");
+      }}"#,
+      url_to_file_path(entry_specifier)
         .unwrap()
         .to_str()
         .unwrap()
@@ -159,7 +171,7 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
     source.push("export default mod;".to_string());
 
     let translated_source = source.join("\n");
-    Ok(translated_source)
+    Ok(Cow::Owned(translated_source))
   }
 
   async fn analyze_reexports<'a>(
@@ -174,7 +186,7 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
     struct Analysis {
       reexport_specifier: url::Url,
       referrer: url::Url,
-      analysis: CjsAnalysis,
+      analysis: CjsAnalysis<'static>,
     }
 
     type AnalysisFuture<'a> = LocalBoxFuture<'a, Result<Analysis, AnyError>>;
@@ -297,15 +309,13 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
       todo!();
     }
 
-    let referrer_path = referrer.to_file_path().unwrap();
+    let referrer_path = url_to_file_path(referrer).unwrap();
     if specifier.starts_with("./") || specifier.starts_with("../") {
       if let Some(parent) = referrer_path.parent() {
-        return Some(
-          self
-            .file_extension_probe(parent.join(specifier), &referrer_path)
-            .map(|p| to_file_specifier(&p)),
-        )
-        .transpose();
+        return self
+          .file_extension_probe(parent.join(specifier), &referrer_path)
+          .and_then(|p| url_from_file_path(&p).map_err(AnyError::from))
+          .map(Some);
       } else {
         todo!();
       }
@@ -331,8 +341,9 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
     }?;
 
     let package_json_path = module_dir.join("package.json");
-    let maybe_package_json =
-      load_pkg_json(self.env.pkg_json_fs(), &package_json_path)?;
+    let maybe_package_json = self
+      .pkg_json_resolver
+      .load_package_json(&package_json_path)?;
     if let Some(package_json) = maybe_package_json {
       if let Some(exports) = &package_json.exports {
         return Some(
@@ -358,35 +369,34 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
         if self.env.is_dir_sync(&d) {
           // subdir might have a package.json that specifies the entrypoint
           let package_json_path = d.join("package.json");
-          let maybe_package_json =
-            load_pkg_json(self.env.pkg_json_fs(), &package_json_path)?;
+          let maybe_package_json = self
+            .pkg_json_resolver
+            .load_package_json(&package_json_path)?;
           if let Some(package_json) = maybe_package_json {
             if let Some(main) = package_json.main(NodeModuleKind::Cjs) {
-              return Ok(Some(to_file_specifier(&d.join(main).clean())));
+              return Ok(Some(url_from_file_path(&d.join(main).clean())?));
             }
           }
 
-          return Ok(Some(to_file_specifier(&d.join("index.js").clean())));
+          return Ok(Some(url_from_file_path(&d.join("index.js").clean())?));
         }
-        return Some(
-          self
-            .file_extension_probe(d, &referrer_path)
-            .map(|p| to_file_specifier(&p)),
-        )
-        .transpose();
+        return self
+          .file_extension_probe(d, &referrer_path)
+          .and_then(|p| url_from_file_path(&p).map_err(AnyError::from))
+          .map(Some);
       } else if let Some(main) = package_json.main(NodeModuleKind::Cjs) {
-        return Ok(Some(to_file_specifier(&module_dir.join(main).clean())));
+        return Ok(Some(url_from_file_path(&module_dir.join(main).clean())?));
       } else {
-        return Ok(Some(to_file_specifier(
+        return Ok(Some(url_from_file_path(
           &module_dir.join("index.js").clean(),
-        )));
+        )?));
       }
     }
 
     // as a fallback, attempt to resolve it via the ancestor directories
     let mut last = referrer_path.as_path();
     while let Some(parent) = last.parent() {
-      if !self.npm_resolver.in_npm_package_at_dir_path(parent) {
+      if !self.in_npm_pkg_checker.in_npm_package_at_dir_path(parent) {
         break;
       }
       let path = if parent.ends_with("node_modules") {
@@ -395,7 +405,7 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
         parent.join("node_modules").join(specifier)
       };
       if let Ok(path) = self.file_extension_probe(path, &referrer_path) {
-        return Ok(Some(to_file_specifier(&path)));
+        return Ok(Some(url_from_file_path(&path)?));
       }
       last = parent;
     }
diff --git a/ext/node_resolver/clippy.toml b/resolvers/node/clippy.toml
similarity index 94%
rename from ext/node_resolver/clippy.toml
rename to resolvers/node/clippy.toml
index 86150781bb..90eaba3fae 100644
--- a/ext/node_resolver/clippy.toml
+++ b/resolvers/node/clippy.toml
@@ -42,6 +42,9 @@ disallowed-methods = [
   { path = "std::fs::write", reason = "File system operations should be done using NodeResolverFs trait" },
   { path = "std::path::Path::canonicalize", reason = "File system operations should be done using NodeResolverFs trait" },
   { path = "std::path::Path::exists", reason = "File system operations should be done using NodeResolverFs trait" },
+  { path = "url::Url::to_file_path", reason = "Use deno_path_util instead so it works in Wasm" },
+  { path = "url::Url::from_file_path", reason = "Use deno_path_util instead so it works in Wasm" },
+  { path = "url::Url::from_directory_path", reason = "Use deno_path_util instead so it works in Wasm" },
 ]
 disallowed-types = [
   { path = "std::sync::Arc", reason = "use crate::sync::MaybeArc instead" },
diff --git a/ext/node_resolver/env.rs b/resolvers/node/env.rs
similarity index 100%
rename from ext/node_resolver/env.rs
rename to resolvers/node/env.rs
diff --git a/ext/node_resolver/errors.rs b/resolvers/node/errors.rs
similarity index 92%
rename from ext/node_resolver/errors.rs
rename to resolvers/node/errors.rs
index 4ba829eda5..aacbecefb4 100644
--- a/ext/node_resolver/errors.rs
+++ b/resolvers/node/errors.rs
@@ -81,29 +81,6 @@ pub trait NodeJsErrorCoded {
   fn code(&self) -> NodeJsErrorCode;
 }
 
-kinded_err!(
-  ResolvePkgSubpathFromDenoModuleError,
-  ResolvePkgSubpathFromDenoModuleErrorKind
-);
-
-impl NodeJsErrorCoded for ResolvePkgSubpathFromDenoModuleError {
-  fn code(&self) -> NodeJsErrorCode {
-    use ResolvePkgSubpathFromDenoModuleErrorKind::*;
-    match self.as_kind() {
-      PackageSubpathResolve(e) => e.code(),
-      UrlToNodeResolution(e) => e.code(),
-    }
-  }
-}
-
-#[derive(Debug, Error)]
-pub enum ResolvePkgSubpathFromDenoModuleErrorKind {
-  #[error(transparent)]
-  PackageSubpathResolve(#[from] PackageSubpathResolveError),
-  #[error(transparent)]
-  UrlToNodeResolution(#[from] UrlToNodeResolutionError),
-}
-
 // todo(https://github.com/denoland/deno_core/issues/810): make this a TypeError
 #[derive(Debug, Clone, Error)]
 #[error(
@@ -394,37 +371,6 @@ impl NodeJsErrorCoded for CanonicalizingPkgJsonDirError {
   }
 }
 
-#[derive(Debug, Error)]
-#[error("TypeScript files are not supported in npm packages: {specifier}")]
-pub struct TypeScriptNotSupportedInNpmError {
-  pub specifier: Url,
-}
-
-impl NodeJsErrorCoded for TypeScriptNotSupportedInNpmError {
-  fn code(&self) -> NodeJsErrorCode {
-    NodeJsErrorCode::ERR_UNKNOWN_FILE_EXTENSION
-  }
-}
-
-kinded_err!(UrlToNodeResolutionError, UrlToNodeResolutionErrorKind);
-
-impl NodeJsErrorCoded for UrlToNodeResolutionError {
-  fn code(&self) -> NodeJsErrorCode {
-    match self.as_kind() {
-      UrlToNodeResolutionErrorKind::TypeScriptNotSupported(e) => e.code(),
-      UrlToNodeResolutionErrorKind::ClosestPkgJson(e) => e.code(),
-    }
-  }
-}
-
-#[derive(Debug, Error)]
-pub enum UrlToNodeResolutionErrorKind {
-  #[error(transparent)]
-  TypeScriptNotSupported(#[from] TypeScriptNotSupportedInNpmError),
-  #[error(transparent)]
-  ClosestPkgJson(#[from] ClosestPkgJsonError),
-}
-
 // todo(https://github.com/denoland/deno_core/issues/810): make this a TypeError
 #[derive(Debug, Error)]
 #[error(
@@ -533,8 +479,6 @@ pub enum NodeResolveErrorKind {
   TypesNotFound(#[from] TypesNotFoundError),
   #[error(transparent)]
   FinalizeResolution(#[from] FinalizeResolutionError),
-  #[error(transparent)]
-  UrlToNodeResolution(#[from] UrlToNodeResolutionError),
 }
 
 kinded_err!(FinalizeResolutionError, FinalizeResolutionErrorKind);
@@ -728,8 +672,6 @@ pub enum ResolvePkgJsonBinExportError {
   MissingPkgJson { pkg_json_path: PathBuf },
   #[error("Failed resolving binary export. {message}")]
   InvalidBinProperty { message: String },
-  #[error(transparent)]
-  UrlToNodeResolution(#[from] UrlToNodeResolutionError),
 }
 
 #[derive(Debug, Error)]
diff --git a/ext/node_resolver/lib.rs b/resolvers/node/lib.rs
similarity index 68%
rename from ext/node_resolver/lib.rs
rename to resolvers/node/lib.rs
index f03f770486..87bd629946 100644
--- a/ext/node_resolver/lib.rs
+++ b/resolvers/node/lib.rs
@@ -13,12 +13,16 @@ mod resolution;
 mod sync;
 
 pub use deno_package_json::PackageJson;
-pub use npm::NpmResolver;
-pub use npm::NpmResolverRc;
-pub use package_json::load_pkg_json;
+pub use npm::InNpmPackageChecker;
+pub use npm::InNpmPackageCheckerRc;
+pub use npm::NpmPackageFolderResolver;
+pub use npm::NpmPackageFolderResolverRc;
+pub use package_json::PackageJsonResolver;
+pub use package_json::PackageJsonResolverRc;
 pub use package_json::PackageJsonThreadLocalCache;
 pub use path::PathClean;
 pub use resolution::parse_npm_pkg_name;
+pub use resolution::resolve_specifier_into_node_modules;
 pub use resolution::NodeModuleKind;
 pub use resolution::NodeResolution;
 pub use resolution::NodeResolutionMode;
diff --git a/ext/node_resolver/npm.rs b/resolvers/node/npm.rs
similarity index 54%
rename from ext/node_resolver/npm.rs
rename to resolvers/node/npm.rs
index 77df57c489..ab3a179426 100644
--- a/ext/node_resolver/npm.rs
+++ b/resolvers/node/npm.rs
@@ -3,6 +3,8 @@
 use std::path::Path;
 use std::path::PathBuf;
 
+use deno_path_util::url_from_directory_path;
+use deno_path_util::url_from_file_path;
 use url::Url;
 
 use crate::errors;
@@ -11,20 +13,29 @@ use crate::sync::MaybeSend;
 use crate::sync::MaybeSync;
 
 #[allow(clippy::disallowed_types)]
-pub type NpmResolverRc = crate::sync::MaybeArc<dyn NpmResolver>;
+pub type NpmPackageFolderResolverRc =
+  crate::sync::MaybeArc<dyn NpmPackageFolderResolver>;
 
-pub trait NpmResolver: std::fmt::Debug + MaybeSend + MaybeSync {
-  /// Resolves an npm package folder path from an npm package referrer.
+pub trait NpmPackageFolderResolver:
+  std::fmt::Debug + MaybeSend + MaybeSync
+{
+  /// Resolves an npm package folder path from the specified referrer.
   fn resolve_package_folder_from_package(
     &self,
     specifier: &str,
     referrer: &Url,
   ) -> Result<PathBuf, errors::PackageFolderResolveError>;
+}
 
+#[allow(clippy::disallowed_types)]
+pub type InNpmPackageCheckerRc = crate::sync::MaybeArc<dyn InNpmPackageChecker>;
+
+/// Checks if a provided specifier is in an npm package.
+pub trait InNpmPackageChecker: std::fmt::Debug + MaybeSend + MaybeSync {
   fn in_npm_package(&self, specifier: &Url) -> bool;
 
   fn in_npm_package_at_dir_path(&self, path: &Path) -> bool {
-    let specifier = match Url::from_directory_path(path.to_path_buf().clean()) {
+    let specifier = match url_from_directory_path(&path.to_path_buf().clean()) {
       Ok(p) => p,
       Err(_) => return false,
     };
@@ -32,7 +43,7 @@ pub trait NpmResolver: std::fmt::Debug + MaybeSend + MaybeSync {
   }
 
   fn in_npm_package_at_file_path(&self, path: &Path) -> bool {
-    let specifier = match Url::from_file_path(path.to_path_buf().clean()) {
+    let specifier = match url_from_file_path(&path.to_path_buf().clean()) {
       Ok(p) => p,
       Err(_) => return false,
     };
diff --git a/resolvers/node/package_json.rs b/resolvers/node/package_json.rs
new file mode 100644
index 0000000000..ae016ebe3e
--- /dev/null
+++ b/resolvers/node/package_json.rs
@@ -0,0 +1,129 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+use deno_package_json::PackageJson;
+use deno_package_json::PackageJsonRc;
+use deno_path_util::strip_unc_prefix;
+use std::cell::RefCell;
+use std::collections::HashMap;
+use std::io::ErrorKind;
+use std::path::Path;
+use std::path::PathBuf;
+use url::Url;
+
+use crate::env::NodeResolverEnv;
+use crate::errors::CanonicalizingPkgJsonDirError;
+use crate::errors::ClosestPkgJsonError;
+use crate::errors::PackageJsonLoadError;
+
+// it would be nice if this was passed down as a ctor arg to the package.json resolver,
+// but it's a little bit complicated to do that, so we just maintain a thread local cache
+thread_local! {
+  static CACHE: RefCell<HashMap<PathBuf, PackageJsonRc>> = RefCell::new(HashMap::new());
+}
+
+pub struct PackageJsonThreadLocalCache;
+
+impl PackageJsonThreadLocalCache {
+  pub fn clear() {
+    CACHE.with(|cache| cache.borrow_mut().clear());
+  }
+}
+
+impl deno_package_json::PackageJsonCache for PackageJsonThreadLocalCache {
+  fn get(&self, path: &Path) -> Option<PackageJsonRc> {
+    CACHE.with(|cache| cache.borrow().get(path).cloned())
+  }
+
+  fn set(&self, path: PathBuf, package_json: PackageJsonRc) {
+    CACHE.with(|cache| cache.borrow_mut().insert(path, package_json));
+  }
+}
+
+#[allow(clippy::disallowed_types)]
+pub type PackageJsonResolverRc<TEnv> =
+  crate::sync::MaybeArc<PackageJsonResolver<TEnv>>;
+
+#[derive(Debug)]
+pub struct PackageJsonResolver<TEnv: NodeResolverEnv> {
+  env: TEnv,
+}
+
+impl<TEnv: NodeResolverEnv> PackageJsonResolver<TEnv> {
+  pub fn new(env: TEnv) -> Self {
+    Self { env }
+  }
+
+  pub fn get_closest_package_json(
+    &self,
+    url: &Url,
+  ) -> Result<Option<PackageJsonRc>, ClosestPkgJsonError> {
+    let Ok(file_path) = deno_path_util::url_to_file_path(url) else {
+      return Ok(None);
+    };
+    self.get_closest_package_json_from_path(&file_path)
+  }
+
+  pub fn get_closest_package_json_from_path(
+    &self,
+    file_path: &Path,
+  ) -> Result<Option<PackageJsonRc>, ClosestPkgJsonError> {
+    // we use this for deno compile using byonm because the script paths
+    // won't be in virtual file system, but the package.json paths will be
+    fn canonicalize_first_ancestor_exists<TEnv: NodeResolverEnv>(
+      dir_path: &Path,
+      env: &TEnv,
+    ) -> Result<Option<PathBuf>, std::io::Error> {
+      for ancestor in dir_path.ancestors() {
+        match env.realpath_sync(ancestor) {
+          Ok(dir_path) => return Ok(Some(dir_path)),
+          Err(err) if err.kind() == std::io::ErrorKind::NotFound => {
+            // keep searching
+          }
+          Err(err) => return Err(err),
+        }
+      }
+      Ok(None)
+    }
+
+    let parent_dir = file_path.parent().unwrap();
+    let Some(start_dir) = canonicalize_first_ancestor_exists(
+      parent_dir, &self.env,
+    )
+    .map_err(|source| CanonicalizingPkgJsonDirError {
+      dir_path: parent_dir.to_path_buf(),
+      source,
+    })?
+    else {
+      return Ok(None);
+    };
+    let start_dir = strip_unc_prefix(start_dir);
+    for current_dir in start_dir.ancestors() {
+      let package_json_path = current_dir.join("package.json");
+      if let Some(pkg_json) = self.load_package_json(&package_json_path)? {
+        return Ok(Some(pkg_json));
+      }
+    }
+
+    Ok(None)
+  }
+
+  pub fn load_package_json(
+    &self,
+    path: &Path,
+  ) -> Result<Option<PackageJsonRc>, PackageJsonLoadError> {
+    let result = PackageJson::load_from_path(
+      path,
+      self.env.pkg_json_fs(),
+      Some(&PackageJsonThreadLocalCache),
+    );
+    match result {
+      Ok(pkg_json) => Ok(Some(pkg_json)),
+      Err(deno_package_json::PackageJsonLoadError::Io { source, .. })
+        if source.kind() == ErrorKind::NotFound =>
+      {
+        Ok(None)
+      }
+      Err(err) => Err(PackageJsonLoadError(err)),
+    }
+  }
+}
diff --git a/resolvers/node/path.rs b/resolvers/node/path.rs
new file mode 100644
index 0000000000..8c2d35fadf
--- /dev/null
+++ b/resolvers/node/path.rs
@@ -0,0 +1,81 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+use std::path::Component;
+use std::path::Path;
+use std::path::PathBuf;
+
+/// Extension to path_clean::PathClean
+pub trait PathClean<T> {
+  fn clean(&self) -> T;
+}
+
+impl PathClean<PathBuf> for PathBuf {
+  fn clean(&self) -> PathBuf {
+    fn is_clean_path(path: &Path) -> bool {
+      let path = path.to_string_lossy();
+      let mut current_index = 0;
+      while let Some(index) = path[current_index..].find("\\.") {
+        let trailing_index = index + current_index + 2;
+        let mut trailing_chars = path[trailing_index..].chars();
+        match trailing_chars.next() {
+          Some('.') => match trailing_chars.next() {
+            Some('/') | Some('\\') | None => {
+              return false;
+            }
+            _ => {}
+          },
+          Some('/') | Some('\\') => {
+            return false;
+          }
+          _ => {}
+        }
+        current_index = trailing_index;
+      }
+      true
+    }
+
+    let path = path_clean::PathClean::clean(self);
+    if cfg!(windows) && !is_clean_path(&path) {
+      // temporary workaround because path_clean::PathClean::clean is
+      // not good enough on windows
+      let mut components = Vec::new();
+
+      for component in path.components() {
+        match component {
+          Component::CurDir => {
+            // skip
+          }
+          Component::ParentDir => {
+            let maybe_last_component = components.pop();
+            if !matches!(maybe_last_component, Some(Component::Normal(_))) {
+              panic!("Error normalizing: {}", path.display());
+            }
+          }
+          Component::Normal(_) | Component::RootDir | Component::Prefix(_) => {
+            components.push(component);
+          }
+        }
+      }
+      components.into_iter().collect::<PathBuf>()
+    } else {
+      path
+    }
+  }
+}
+
+#[cfg(test)]
+mod test {
+  #[cfg(windows)]
+  #[test]
+  fn test_path_clean() {
+    use super::*;
+
+    run_test("C:\\test\\./file.txt", "C:\\test\\file.txt");
+    run_test("C:\\test\\../other/file.txt", "C:\\other\\file.txt");
+    run_test("C:\\test\\../other\\file.txt", "C:\\other\\file.txt");
+
+    fn run_test(input: &str, expected: &str) {
+      assert_eq!(PathBuf::from(input).clean(), PathBuf::from(expected));
+    }
+  }
+}
diff --git a/ext/node_resolver/resolution.rs b/resolvers/node/resolution.rs
similarity index 88%
rename from ext/node_resolver/resolution.rs
rename to resolvers/node/resolution.rs
index ad9dbb7100..673a61abe6 100644
--- a/ext/node_resolver/resolution.rs
+++ b/resolvers/node/resolution.rs
@@ -6,16 +6,13 @@ use std::path::PathBuf;
 
 use anyhow::bail;
 use anyhow::Error as AnyError;
-use deno_media_type::MediaType;
-use deno_package_json::PackageJsonRc;
+use deno_path_util::url_from_file_path;
 use serde_json::Map;
 use serde_json::Value;
 use url::Url;
 
 use crate::env::NodeResolverEnv;
 use crate::errors;
-use crate::errors::CanonicalizingPkgJsonDirError;
-use crate::errors::ClosestPkgJsonError;
 use crate::errors::DataUrlReferrerError;
 use crate::errors::FinalizeResolutionError;
 use crate::errors::InvalidModuleSpecifierError;
@@ -30,7 +27,6 @@ use crate::errors::PackageExportsResolveError;
 use crate::errors::PackageImportNotDefinedError;
 use crate::errors::PackageImportsResolveError;
 use crate::errors::PackageImportsResolveErrorKind;
-use crate::errors::PackageJsonLoadError;
 use crate::errors::PackagePathNotExportedError;
 use crate::errors::PackageResolveError;
 use crate::errors::PackageSubpathResolveError;
@@ -40,16 +36,13 @@ use crate::errors::PackageTargetResolveError;
 use crate::errors::PackageTargetResolveErrorKind;
 use crate::errors::ResolveBinaryCommandsError;
 use crate::errors::ResolvePkgJsonBinExportError;
-use crate::errors::ResolvePkgSubpathFromDenoModuleError;
-use crate::errors::TypeScriptNotSupportedInNpmError;
 use crate::errors::TypesNotFoundError;
 use crate::errors::TypesNotFoundErrorData;
 use crate::errors::UnsupportedDirImportError;
 use crate::errors::UnsupportedEsmUrlSchemeError;
-use crate::errors::UrlToNodeResolutionError;
-use crate::path::strip_unc_prefix;
-use crate::path::to_file_specifier;
-use crate::NpmResolverRc;
+use crate::npm::InNpmPackageCheckerRc;
+use crate::NpmPackageFolderResolverRc;
+use crate::PackageJsonResolverRc;
 use crate::PathClean;
 use deno_package_json::PackageJson;
 
@@ -57,6 +50,15 @@ pub static DEFAULT_CONDITIONS: &[&str] = &["deno", "node", "import"];
 pub static REQUIRE_CONDITIONS: &[&str] = &["require", "node"];
 static TYPES_ONLY_CONDITIONS: &[&str] = &["types"];
 
+fn conditions_from_module_kind(
+  kind: NodeModuleKind,
+) -> &'static [&'static str] {
+  match kind {
+    NodeModuleKind::Esm => DEFAULT_CONDITIONS,
+    NodeModuleKind::Cjs => REQUIRE_CONDITIONS,
+  }
+}
+
 pub type NodeModuleKind = deno_package_json::NodeModuleKind;
 
 #[derive(Debug, Clone, Copy, PartialEq, Eq)]
@@ -73,16 +75,14 @@ impl NodeResolutionMode {
 
 #[derive(Debug)]
 pub enum NodeResolution {
-  Esm(Url),
-  CommonJs(Url),
+  Module(Url),
   BuiltIn(String),
 }
 
 impl NodeResolution {
   pub fn into_url(self) -> Url {
     match self {
-      Self::Esm(u) => u,
-      Self::CommonJs(u) => u,
+      Self::Module(u) => u,
       Self::BuiltIn(specifier) => {
         if specifier.starts_with("node:") {
           Url::parse(&specifier).unwrap()
@@ -92,42 +92,6 @@ impl NodeResolution {
       }
     }
   }
-
-  pub fn into_specifier_and_media_type(
-    resolution: Option<Self>,
-  ) -> (Url, MediaType) {
-    match resolution {
-      Some(NodeResolution::CommonJs(specifier)) => {
-        let media_type = MediaType::from_specifier(&specifier);
-        (
-          specifier,
-          match media_type {
-            MediaType::JavaScript | MediaType::Jsx => MediaType::Cjs,
-            MediaType::TypeScript | MediaType::Tsx => MediaType::Cts,
-            MediaType::Dts => MediaType::Dcts,
-            _ => media_type,
-          },
-        )
-      }
-      Some(NodeResolution::Esm(specifier)) => {
-        let media_type = MediaType::from_specifier(&specifier);
-        (
-          specifier,
-          match media_type {
-            MediaType::JavaScript | MediaType::Jsx => MediaType::Mjs,
-            MediaType::TypeScript | MediaType::Tsx => MediaType::Mts,
-            MediaType::Dts => MediaType::Dmts,
-            _ => media_type,
-          },
-        )
-      }
-      Some(resolution) => (resolution.into_url(), MediaType::Dts),
-      None => (
-        Url::parse("internal:///missing_dependency.d.ts").unwrap(),
-        MediaType::Dts,
-      ),
-    }
-  }
 }
 
 #[allow(clippy::disallowed_types)]
@@ -136,16 +100,28 @@ pub type NodeResolverRc<TEnv> = crate::sync::MaybeArc<NodeResolver<TEnv>>;
 #[derive(Debug)]
 pub struct NodeResolver<TEnv: NodeResolverEnv> {
   env: TEnv,
-  npm_resolver: NpmResolverRc,
+  in_npm_pkg_checker: InNpmPackageCheckerRc,
+  npm_pkg_folder_resolver: NpmPackageFolderResolverRc,
+  pkg_json_resolver: PackageJsonResolverRc<TEnv>,
 }
 
 impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
-  pub fn new(env: TEnv, npm_resolver: NpmResolverRc) -> Self {
-    Self { env, npm_resolver }
+  pub fn new(
+    env: TEnv,
+    in_npm_pkg_checker: InNpmPackageCheckerRc,
+    npm_pkg_folder_resolver: NpmPackageFolderResolverRc,
+    pkg_json_resolver: PackageJsonResolverRc<TEnv>,
+  ) -> Self {
+    Self {
+      env,
+      in_npm_pkg_checker,
+      npm_pkg_folder_resolver,
+      pkg_json_resolver,
+    }
   }
 
   pub fn in_npm_package(&self, specifier: &Url) -> bool {
-    self.npm_resolver.in_npm_package(specifier)
+    self.in_npm_pkg_checker.in_npm_package(specifier)
   }
 
   /// This function is an implementation of `defaultResolve` in
@@ -166,7 +142,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
 
     if let Ok(url) = Url::parse(specifier) {
       if url.scheme() == "data" {
-        return Ok(NodeResolution::Esm(url));
+        return Ok(NodeResolution::Module(url));
       }
 
       if let Some(module_name) =
@@ -191,7 +167,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
         let url = referrer
           .join(specifier)
           .map_err(|source| DataUrlReferrerError { source })?;
-        return Ok(NodeResolution::Esm(url));
+        return Ok(NodeResolution::Module(url));
       }
     }
 
@@ -199,8 +175,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
       specifier,
       referrer,
       referrer_kind,
-      // even though the referrer may be CJS, if we're here that means we're doing ESM resolution
-      DEFAULT_CONDITIONS,
+      conditions_from_module_kind(referrer_kind),
       mode,
     )?;
 
@@ -212,7 +187,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     };
 
     let url = self.finalize_resolution(url, Some(referrer))?;
-    let resolve_response = self.url_to_node_resolution(url)?;
+    let resolve_response = NodeResolution::Module(url);
     // TODO(bartlomieju): skipped checking errors for commonJS resolution and
     // "preserveSymlinksMain"/"preserveSymlinks" options.
     Ok(resolve_response)
@@ -236,6 +211,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
       })?)
     } else if specifier.starts_with('#') {
       let pkg_config = self
+        .pkg_json_resolver
         .get_closest_package_json(referrer)
         .map_err(PackageImportsResolveErrorKind::ClosestPkgJson)
         .map_err(|err| PackageImportsResolveError(Box::new(err)))?;
@@ -331,9 +307,9 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     package_dir: &Path,
     package_subpath: Option<&str>,
     maybe_referrer: Option<&Url>,
+    referrer_kind: NodeModuleKind,
     mode: NodeResolutionMode,
-  ) -> Result<NodeResolution, ResolvePkgSubpathFromDenoModuleError> {
-    let node_module_kind = NodeModuleKind::Esm;
+  ) -> Result<Url, PackageSubpathResolveError> {
     let package_subpath = package_subpath
       .map(|s| format!("./{s}"))
       .unwrap_or_else(|| ".".to_string());
@@ -341,14 +317,13 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
       package_dir,
       &package_subpath,
       maybe_referrer,
-      node_module_kind,
-      DEFAULT_CONDITIONS,
+      referrer_kind,
+      conditions_from_module_kind(referrer_kind),
       mode,
     )?;
-    let resolve_response = self.url_to_node_resolution(resolved_url)?;
     // TODO(bartlomieju): skipped checking errors for commonJS resolution and
     // "preserveSymlinksMain"/"preserveSymlinks" options.
-    Ok(resolve_response)
+    Ok(resolved_url)
   }
 
   pub fn resolve_binary_commands(
@@ -356,7 +331,9 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     package_folder: &Path,
   ) -> Result<Vec<String>, ResolveBinaryCommandsError> {
     let pkg_json_path = package_folder.join("package.json");
-    let Some(package_json) = self.load_package_json(&pkg_json_path)? else {
+    let Some(package_json) =
+      self.pkg_json_resolver.load_package_json(&pkg_json_path)?
+    else {
       return Ok(Vec::new());
     };
 
@@ -381,9 +358,11 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     &self,
     package_folder: &Path,
     sub_path: Option<&str>,
-  ) -> Result<NodeResolution, ResolvePkgJsonBinExportError> {
+  ) -> Result<Url, ResolvePkgJsonBinExportError> {
     let pkg_json_path = package_folder.join("package.json");
-    let Some(package_json) = self.load_package_json(&pkg_json_path)? else {
+    let Some(package_json) =
+      self.pkg_json_resolver.load_package_json(&pkg_json_path)?
+    else {
       return Err(ResolvePkgJsonBinExportError::MissingPkgJson {
         pkg_json_path,
       });
@@ -394,39 +373,11 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
           message: err.to_string(),
         }
       })?;
-    let url = to_file_specifier(&package_folder.join(bin_entry));
+    let url = url_from_file_path(&package_folder.join(bin_entry)).unwrap();
 
-    let resolve_response = self.url_to_node_resolution(url)?;
     // TODO(bartlomieju): skipped checking errors for commonJS resolution and
     // "preserveSymlinksMain"/"preserveSymlinks" options.
-    Ok(resolve_response)
-  }
-
-  pub fn url_to_node_resolution(
-    &self,
-    url: Url,
-  ) -> Result<NodeResolution, UrlToNodeResolutionError> {
-    let url_str = url.as_str().to_lowercase();
-    if url_str.starts_with("http") || url_str.ends_with(".json") {
-      Ok(NodeResolution::Esm(url))
-    } else if url_str.ends_with(".js") || url_str.ends_with(".d.ts") {
-      let maybe_package_config = self.get_closest_package_json(&url)?;
-      match maybe_package_config {
-        Some(c) if c.typ == "module" => Ok(NodeResolution::Esm(url)),
-        Some(_) => Ok(NodeResolution::CommonJs(url)),
-        None => Ok(NodeResolution::Esm(url)),
-      }
-    } else if url_str.ends_with(".mjs") || url_str.ends_with(".d.mts") {
-      Ok(NodeResolution::Esm(url))
-    } else if url_str.ends_with(".ts") || url_str.ends_with(".mts") {
-      if self.in_npm_package(&url) {
-        Err(TypeScriptNotSupportedInNpmError { specifier: url }.into())
-      } else {
-        Ok(NodeResolution::Esm(url))
-      }
-    } else {
-      Ok(NodeResolution::CommonJs(url))
-    }
+    Ok(url)
   }
 
   /// Checks if the resolved file has a corresponding declaration file.
@@ -485,12 +436,12 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
       || lowercase_path.ends_with(".d.cts")
       || lowercase_path.ends_with(".d.mts")
     {
-      return Ok(to_file_specifier(path));
+      return Ok(url_from_file_path(path).unwrap());
     }
     if let Some(path) =
       probe_extensions(&self.env, path, &lowercase_path, referrer_kind)
     {
-      return Ok(to_file_specifier(&path));
+      return Ok(url_from_file_path(&path).unwrap());
     }
     if self.env.is_dir_sync(path) {
       let resolution_result = self.resolve_package_dir_subpath(
@@ -498,10 +449,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
         /* sub path */ ".",
         maybe_referrer,
         referrer_kind,
-        match referrer_kind {
-          NodeModuleKind::Esm => DEFAULT_CONDITIONS,
-          NodeModuleKind::Cjs => REQUIRE_CONDITIONS,
-        },
+        conditions_from_module_kind(referrer_kind),
         NodeResolutionMode::Types,
       );
       if let Ok(resolution) = resolution_result {
@@ -514,15 +462,15 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
         &index_path.to_string_lossy().to_lowercase(),
         referrer_kind,
       ) {
-        return Ok(to_file_specifier(&path));
+        return Ok(url_from_file_path(&path).unwrap());
       }
     }
     // allow resolving .css files for types resolution
     if lowercase_path.ends_with(".css") {
-      return Ok(to_file_specifier(path));
+      return Ok(url_from_file_path(path).unwrap());
     }
     Err(TypesNotFoundError(Box::new(TypesNotFoundErrorData {
-      code_specifier: to_file_specifier(path),
+      code_specifier: url_from_file_path(path).unwrap(),
       maybe_referrer: maybe_referrer.cloned(),
     })))
   }
@@ -673,7 +621,8 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
             } else {
               format!("{target}{subpath}")
             };
-            let package_json_url = to_file_specifier(package_json_path);
+            let package_json_url =
+              url_from_file_path(package_json_path).unwrap();
             let result = match self.package_resolve(
               &export_target,
               &package_json_url,
@@ -760,7 +709,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
       );
     }
     if subpath.is_empty() {
-      return Ok(to_file_specifier(&resolved_path));
+      return Ok(url_from_file_path(&resolved_path).unwrap());
     }
     if invalid_segment_re.is_match(subpath) {
       let request = if pattern {
@@ -782,9 +731,11 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
       let resolved_path_str = resolved_path.to_string_lossy();
       let replaced = pattern_re
         .replace(&resolved_path_str, |_caps: &regex::Captures| subpath);
-      return Ok(to_file_specifier(&PathBuf::from(replaced.to_string())));
+      return Ok(
+        url_from_file_path(&PathBuf::from(replaced.to_string())).unwrap(),
+      );
     }
-    Ok(to_file_specifier(&resolved_path.join(subpath).clean()))
+    Ok(url_from_file_path(&resolved_path.join(subpath).clean()).unwrap())
   }
 
   #[allow(clippy::too_many_arguments)]
@@ -871,7 +822,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
         mode,
       )?;
       if mode.is_types() && url.scheme() == "file" {
-        let path = url.to_file_path().unwrap();
+        let path = deno_path_util::url_to_file_path(&url).unwrap();
         return Ok(Some(self.path_to_declaration_url(
           &path,
           maybe_referrer,
@@ -1098,7 +1049,9 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     let (package_name, package_subpath, _is_scoped) =
       parse_npm_pkg_name(specifier, referrer)?;
 
-    if let Some(package_config) = self.get_closest_package_json(referrer)? {
+    if let Some(package_config) =
+      self.pkg_json_resolver.get_closest_package_json(referrer)?
+    {
       // ResolveSelf
       if package_config.name.as_ref() == Some(&package_name) {
         if let Some(exports) = &package_config.exports {
@@ -1173,7 +1126,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     mode: NodeResolutionMode,
   ) -> Result<Url, PackageResolveError> {
     let package_dir_path = self
-      .npm_resolver
+      .npm_pkg_folder_resolver
       .resolve_package_folder_from_package(package_name, referrer)?;
 
     // todo: error with this instead when can't find package
@@ -1213,7 +1166,10 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     mode: NodeResolutionMode,
   ) -> Result<Url, PackageSubpathResolveError> {
     let package_json_path = package_dir_path.join("package.json");
-    match self.load_package_json(&package_json_path)? {
+    match self
+      .pkg_json_resolver
+      .load_package_json(&package_json_path)?
+    {
       Some(pkg_json) => self.resolve_package_subpath(
         &pkg_json,
         package_subpath,
@@ -1307,7 +1263,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     if mode.is_types() {
       Ok(self.path_to_declaration_url(&file_path, referrer, referrer_kind)?)
     } else {
-      Ok(to_file_specifier(&file_path))
+      Ok(url_from_file_path(&file_path).unwrap())
     }
   }
 
@@ -1334,70 +1290,6 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     }
   }
 
-  pub fn get_closest_package_json(
-    &self,
-    url: &Url,
-  ) -> Result<Option<PackageJsonRc>, ClosestPkgJsonError> {
-    let Ok(file_path) = url.to_file_path() else {
-      return Ok(None);
-    };
-    self.get_closest_package_json_from_path(&file_path)
-  }
-
-  pub fn get_closest_package_json_from_path(
-    &self,
-    file_path: &Path,
-  ) -> Result<Option<PackageJsonRc>, ClosestPkgJsonError> {
-    // we use this for deno compile using byonm because the script paths
-    // won't be in virtual file system, but the package.json paths will be
-    fn canonicalize_first_ancestor_exists(
-      dir_path: &Path,
-      env: &dyn NodeResolverEnv,
-    ) -> Result<Option<PathBuf>, std::io::Error> {
-      for ancestor in dir_path.ancestors() {
-        match env.realpath_sync(ancestor) {
-          Ok(dir_path) => return Ok(Some(dir_path)),
-          Err(err) if err.kind() == std::io::ErrorKind::NotFound => {
-            // keep searching
-          }
-          Err(err) => return Err(err),
-        }
-      }
-      Ok(None)
-    }
-
-    let parent_dir = file_path.parent().unwrap();
-    let Some(start_dir) = canonicalize_first_ancestor_exists(
-      parent_dir, &self.env,
-    )
-    .map_err(|source| CanonicalizingPkgJsonDirError {
-      dir_path: parent_dir.to_path_buf(),
-      source,
-    })?
-    else {
-      return Ok(None);
-    };
-    let start_dir = strip_unc_prefix(start_dir);
-    for current_dir in start_dir.ancestors() {
-      let package_json_path = current_dir.join("package.json");
-      if let Some(pkg_json) = self.load_package_json(&package_json_path)? {
-        return Ok(Some(pkg_json));
-      }
-    }
-
-    Ok(None)
-  }
-
-  pub fn load_package_json(
-    &self,
-    package_json_path: &Path,
-  ) -> Result<Option<PackageJsonRc>, PackageJsonLoadError> {
-    crate::package_json::load_pkg_json(
-      self.env.pkg_json_fs(),
-      package_json_path,
-    )
-  }
-
   pub(super) fn legacy_main_resolve(
     &self,
     package_json: &PackageJson,
@@ -1433,7 +1325,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     if let Some(main) = maybe_main {
       let guess = package_json.path.parent().unwrap().join(main).clean();
       if self.env.is_file_sync(&guess) {
-        return Ok(to_file_specifier(&guess));
+        return Ok(url_from_file_path(&guess).unwrap());
       }
 
       // todo(dsherret): investigate exactly how node and typescript handles this
@@ -1463,7 +1355,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
           .clean();
         if self.env.is_file_sync(&guess) {
           // TODO(bartlomieju): emitLegacyIndexDeprecation()
-          return Ok(to_file_specifier(&guess));
+          return Ok(url_from_file_path(&guess).unwrap());
         }
       }
     }
@@ -1496,14 +1388,15 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
       let guess = directory.join(index_file_name).clean();
       if self.env.is_file_sync(&guess) {
         // TODO(bartlomieju): emitLegacyIndexDeprecation()
-        return Ok(to_file_specifier(&guess));
+        return Ok(url_from_file_path(&guess).unwrap());
       }
     }
 
     if mode.is_types() {
       Err(
         TypesNotFoundError(Box::new(TypesNotFoundErrorData {
-          code_specifier: to_file_specifier(&directory.join("index.js")),
+          code_specifier: url_from_file_path(&directory.join("index.js"))
+            .unwrap(),
           maybe_referrer: maybe_referrer.cloned(),
         }))
         .into(),
@@ -1511,7 +1404,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     } else {
       Err(
         ModuleNotFoundError {
-          specifier: to_file_specifier(&directory.join("index.js")),
+          specifier: url_from_file_path(&directory.join("index.js")).unwrap(),
           typ: "module",
           maybe_referrer: maybe_referrer.cloned(),
         }
@@ -1519,6 +1412,25 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
       )
     }
   }
+
+  /// Resolves a specifier that is pointing into a node_modules folder by canonicalizing it.
+  ///
+  /// Returns `None` when the specifier is not in a node_modules folder.
+  pub fn handle_if_in_node_modules(&self, specifier: &Url) -> Option<Url> {
+    // skip canonicalizing if we definitely know it's unnecessary
+    if specifier.scheme() == "file"
+      && specifier.path().contains("/node_modules/")
+    {
+      // Specifiers in the node_modules directory are canonicalized
+      // so canoncalize then check if it's in the node_modules directory.
+      let specifier = resolve_specifier_into_node_modules(specifier, &|path| {
+        self.env.realpath_sync(path)
+      });
+      return Some(specifier);
+    }
+
+    None
+  }
 }
 
 fn resolve_bin_entry_value<'a>(
@@ -1611,9 +1523,7 @@ fn resolve_bin_entry_value<'a>(
 }
 
 fn to_file_path(url: &Url) -> PathBuf {
-  url
-    .to_file_path()
-    .unwrap_or_else(|_| panic!("Provided URL was not file:// URL: {url}"))
+  deno_path_util::url_to_file_path(url).unwrap()
 }
 
 fn to_file_path_string(url: &Url) -> String {
@@ -1692,7 +1602,7 @@ fn with_known_extension(path: &Path, ext: &str) -> PathBuf {
 }
 
 fn to_specifier_display_string(url: &Url) -> String {
-  if let Ok(path) = url.to_file_path() {
+  if let Ok(path) = deno_path_util::url_to_file_path(url) {
     path.display().to_string()
   } else {
     url.to_string()
@@ -1769,6 +1679,28 @@ pub fn parse_npm_pkg_name(
   Ok((package_name, package_subpath, is_scoped))
 }
 
+/// Resolves a specifier that is pointing into a node_modules folder.
+///
+/// Note: This should be called whenever getting the specifier from
+/// a Module::External(module) reference because that module might
+/// not be fully resolved at the time deno_graph is analyzing it
+/// because the node_modules folder might not exist at that time.
+pub fn resolve_specifier_into_node_modules(
+  specifier: &Url,
+  canonicalize: &impl Fn(&Path) -> std::io::Result<PathBuf>,
+) -> Url {
+  deno_path_util::url_to_file_path(specifier)
+    .ok()
+    // this path might not exist at the time the graph is being created
+    // because the node_modules folder might not yet exist
+    .and_then(|path| {
+      deno_path_util::canonicalize_path_maybe_not_exists(&path, canonicalize)
+        .ok()
+    })
+    .and_then(|path| deno_path_util::url_from_file_path(&path).ok())
+    .unwrap_or_else(|| specifier.clone())
+}
+
 fn pattern_key_compare(a: &str, b: &str) -> i32 {
   let a_pattern_index = a.find('*');
   let b_pattern_index = b.find('*');
diff --git a/ext/node_resolver/sync.rs b/resolvers/node/sync.rs
similarity index 100%
rename from ext/node_resolver/sync.rs
rename to resolvers/node/sync.rs
diff --git a/runtime/Cargo.toml b/runtime/Cargo.toml
index ea2978c49b..b59cd14fa9 100644
--- a/runtime/Cargo.toml
+++ b/runtime/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_runtime"
-version = "0.177.0"
+version = "0.186.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -88,6 +88,7 @@ deno_kv.workspace = true
 deno_napi.workspace = true
 deno_net.workspace = true
 deno_node.workspace = true
+deno_path_util.workspace = true
 deno_permissions.workspace = true
 deno_terminal.workspace = true
 deno_tls.workspace = true
@@ -99,6 +100,8 @@ deno_websocket.workspace = true
 deno_webstorage.workspace = true
 node_resolver = { workspace = true, features = ["sync"] }
 
+async-trait.workspace = true
+color-print.workspace = true
 dlopen2.workspace = true
 encoding_rs.workspace = true
 fastwebsockets.workspace = true
@@ -112,13 +115,21 @@ log.workspace = true
 netif = "0.1.6"
 notify.workspace = true
 once_cell.workspace = true
+opentelemetry.workspace = true
+opentelemetry-http.workspace = true
+opentelemetry-otlp.workspace = true
+opentelemetry-semantic-conventions.workspace = true
+opentelemetry_sdk.workspace = true
 percent-encoding.workspace = true
+pin-project.workspace = true
 regex.workspace = true
 rustyline = { workspace = true, features = ["custom-bindings"] }
+same-file = "1.0.6"
 serde.workspace = true
 signal-hook = "0.3.17"
 signal-hook-registry = "1.4.0"
 tempfile.workspace = true
+thiserror.workspace = true
 tokio.workspace = true
 tokio-metrics.workspace = true
 twox-hash.workspace = true
diff --git a/runtime/clippy.toml b/runtime/clippy.toml
index 53676a90e6..79e6bbd083 100644
--- a/runtime/clippy.toml
+++ b/runtime/clippy.toml
@@ -42,4 +42,5 @@ disallowed-methods = [
   { path = "std::fs::write", reason = "File system operations should be done using FileSystem trait" },
   { path = "std::path::Path::canonicalize", reason = "File system operations should be done using FileSystem trait" },
   { path = "std::path::Path::exists", reason = "File system operations should be done using FileSystem trait" },
+  { path = "std::process::exit", reason = "use deno_runtime::exit instead" },
 ]
diff --git a/runtime/errors.rs b/runtime/errors.rs
index 694402773e..0c26e0e47a 100644
--- a/runtime/errors.rs
+++ b/runtime/errors.rs
@@ -9,15 +9,116 @@
 //!   Diagnostics are compile-time type errors, whereas JsErrors are runtime
 //!   exceptions.
 
+use crate::ops::fs_events::FsEventsError;
+use crate::ops::http::HttpStartError;
+use crate::ops::os::OsError;
+use crate::ops::permissions::PermissionError;
+use crate::ops::process::CheckRunPermissionError;
+use crate::ops::process::ProcessError;
+use crate::ops::signal::SignalError;
+use crate::ops::tty::TtyError;
+use crate::ops::web_worker::SyncFetchError;
+use crate::ops::worker_host::CreateWorkerError;
+use deno_broadcast_channel::BroadcastChannelError;
+use deno_cache::CacheError;
+use deno_canvas::CanvasError;
 use deno_core::error::AnyError;
 use deno_core::serde_json;
 use deno_core::url;
 use deno_core::ModuleResolutionError;
+use deno_cron::CronError;
+use deno_crypto::DecryptError;
+use deno_crypto::EncryptError;
+use deno_crypto::ExportKeyError;
+use deno_crypto::GenerateKeyError;
+use deno_crypto::ImportKeyError;
+use deno_fetch::FetchError;
+use deno_fetch::HttpClientCreateError;
+use deno_ffi::CallError;
+use deno_ffi::CallbackError;
+use deno_ffi::DlfcnError;
+use deno_ffi::IRError;
+use deno_ffi::ReprError;
+use deno_ffi::StaticError;
+use deno_fs::FsOpsError;
+use deno_http::HttpError;
+use deno_http::HttpNextError;
+use deno_http::WebSocketUpgradeError;
+use deno_io::fs::FsError;
+use deno_kv::KvCheckError;
+use deno_kv::KvError;
+use deno_kv::KvMutationError;
+use deno_napi::NApiError;
+use deno_net::ops::NetError;
+use deno_permissions::ChildPermissionError;
+use deno_permissions::NetDescriptorFromUrlParseError;
+use deno_permissions::PathResolveError;
+use deno_permissions::PermissionCheckError;
+use deno_permissions::RunDescriptorParseError;
+use deno_permissions::SysDescriptorParseError;
+use deno_tls::TlsError;
+use deno_web::BlobError;
+use deno_web::CompressionError;
+use deno_web::MessagePortError;
+use deno_web::StreamResourceError;
+use deno_web::WebError;
+use deno_websocket::HandshakeError;
+use deno_websocket::WebsocketError;
+use deno_webstorage::WebStorageError;
+use rustyline::error::ReadlineError;
 use std::env;
 use std::error::Error;
 use std::io;
 use std::sync::Arc;
 
+fn get_run_descriptor_parse_error(e: &RunDescriptorParseError) -> &'static str {
+  match e {
+    RunDescriptorParseError::Which(_) => "Error",
+    RunDescriptorParseError::PathResolve(e) => get_path_resolve_error(e),
+    RunDescriptorParseError::EmptyRunQuery => "Error",
+  }
+}
+
+fn get_sys_descriptor_parse_error(e: &SysDescriptorParseError) -> &'static str {
+  match e {
+    SysDescriptorParseError::InvalidKind(_) => "TypeError",
+    SysDescriptorParseError::Empty => "Error",
+  }
+}
+
+fn get_path_resolve_error(e: &PathResolveError) -> &'static str {
+  match e {
+    PathResolveError::CwdResolve(e) => get_io_error_class(e),
+    PathResolveError::EmptyPath => "Error",
+  }
+}
+
+fn get_permission_error_class(e: &PermissionError) -> &'static str {
+  match e {
+    PermissionError::InvalidPermissionName(_) => "ReferenceError",
+    PermissionError::PathResolve(e) => get_path_resolve_error(e),
+    PermissionError::NetDescriptorParse(_) => "URIError",
+    PermissionError::SysDescriptorParse(e) => get_sys_descriptor_parse_error(e),
+    PermissionError::RunDescriptorParse(e) => get_run_descriptor_parse_error(e),
+  }
+}
+
+fn get_permission_check_error_class(e: &PermissionCheckError) -> &'static str {
+  match e {
+    PermissionCheckError::PermissionDenied(_) => "NotCapable",
+    PermissionCheckError::InvalidFilePath(_) => "URIError",
+    PermissionCheckError::NetDescriptorForUrlParse(e) => match e {
+      NetDescriptorFromUrlParseError::MissingHost(_) => "TypeError",
+      NetDescriptorFromUrlParseError::Host(_) => "URIError",
+    },
+    PermissionCheckError::SysDescriptorParse(e) => {
+      get_sys_descriptor_parse_error(e)
+    }
+    PermissionCheckError::PathResolve(e) => get_path_resolve_error(e),
+    PermissionCheckError::HostParse(_) => "URIError",
+  }
+}
+
 fn get_dlopen_error_class(error: &dlopen2::Error) -> &'static str {
   use dlopen2::Error::*;
   match error {
@@ -153,12 +254,1624 @@ pub fn get_nix_error_class(error: &nix::Error) -> &'static str {
   }
 }
 
+fn get_webgpu_error_class(e: &deno_webgpu::InitError) -> &'static str {
+  match e {
+    deno_webgpu::InitError::Resource(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    deno_webgpu::InitError::InvalidAdapter(_) => "Error",
+    deno_webgpu::InitError::RequestDevice(_) => "DOMExceptionOperationError",
+    deno_webgpu::InitError::InvalidDevice(_) => "Error",
+  }
+}
+
+fn get_webgpu_buffer_error_class(
+  e: &deno_webgpu::buffer::BufferError,
+) -> &'static str {
+  match e {
+    deno_webgpu::buffer::BufferError::Resource(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    deno_webgpu::buffer::BufferError::InvalidUsage => "TypeError",
+    deno_webgpu::buffer::BufferError::Access(_) => "DOMExceptionOperationError",
+  }
+}
+
+fn get_webgpu_bundle_error_class(
+  e: &deno_webgpu::bundle::BundleError,
+) -> &'static str {
+  match e {
+    deno_webgpu::bundle::BundleError::Resource(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    deno_webgpu::bundle::BundleError::InvalidSize => "TypeError",
+  }
+}
+
+fn get_webgpu_byow_error_class(
+  e: &deno_webgpu::byow::ByowError,
+) -> &'static str {
+  match e {
+    deno_webgpu::byow::ByowError::WebGPUNotInitiated => "TypeError",
+    deno_webgpu::byow::ByowError::InvalidParameters => "TypeError",
+    deno_webgpu::byow::ByowError::CreateSurface(_) => "Error",
+    deno_webgpu::byow::ByowError::InvalidSystem => "TypeError",
+    #[cfg(any(
+      target_os = "windows",
+      target_os = "linux",
+      target_os = "freebsd",
+      target_os = "openbsd"
+    ))]
+    deno_webgpu::byow::ByowError::NullWindow => "TypeError",
+    #[cfg(any(
+      target_os = "linux",
+      target_os = "freebsd",
+      target_os = "openbsd"
+    ))]
+    deno_webgpu::byow::ByowError::NullDisplay => "TypeError",
+    #[cfg(target_os = "macos")]
+    deno_webgpu::byow::ByowError::NSViewDisplay => "TypeError",
+  }
+}
+
+fn get_webgpu_render_pass_error_class(
+  e: &deno_webgpu::render_pass::RenderPassError,
+) -> &'static str {
+  match e {
+    deno_webgpu::render_pass::RenderPassError::Resource(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    deno_webgpu::render_pass::RenderPassError::InvalidSize => "TypeError",
+  }
+}
+
+fn get_webgpu_surface_error_class(
+  e: &deno_webgpu::surface::SurfaceError,
+) -> &'static str {
+  match e {
+    deno_webgpu::surface::SurfaceError::Resource(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    deno_webgpu::surface::SurfaceError::Surface(_) => "Error",
+    deno_webgpu::surface::SurfaceError::InvalidStatus => "Error",
+  }
+}
+
+fn get_crypto_decrypt_error_class(e: &DecryptError) -> &'static str {
+  match e {
+    DecryptError::General(e) => get_crypto_shared_error_class(e),
+    DecryptError::Pkcs1(_) => "Error",
+    DecryptError::Failed => "DOMExceptionOperationError",
+    DecryptError::InvalidLength => "TypeError",
+    DecryptError::InvalidCounterLength => "TypeError",
+    DecryptError::InvalidTagLength => "TypeError",
+    DecryptError::InvalidKeyOrIv => "DOMExceptionOperationError",
+    DecryptError::TooMuchData => "DOMExceptionOperationError",
+    DecryptError::InvalidIvLength => "TypeError",
+    DecryptError::Rsa(_) => "DOMExceptionOperationError",
+  }
+}
+
+fn get_crypto_encrypt_error_class(e: &EncryptError) -> &'static str {
+  match e {
+    EncryptError::General(e) => get_crypto_shared_error_class(e),
+    EncryptError::InvalidKeyOrIv => "DOMExceptionOperationError",
+    EncryptError::Failed => "DOMExceptionOperationError",
+    EncryptError::InvalidLength => "TypeError",
+    EncryptError::InvalidIvLength => "TypeError",
+    EncryptError::InvalidCounterLength => "TypeError",
+    EncryptError::TooMuchData => "DOMExceptionOperationError",
+  }
+}
+
+fn get_crypto_shared_error_class(e: &deno_crypto::SharedError) -> &'static str {
+  match e {
+    deno_crypto::SharedError::ExpectedValidPrivateKey => "TypeError",
+    deno_crypto::SharedError::ExpectedValidPublicKey => "TypeError",
+    deno_crypto::SharedError::ExpectedValidPrivateECKey => "TypeError",
+    deno_crypto::SharedError::ExpectedValidPublicECKey => "TypeError",
+    deno_crypto::SharedError::ExpectedPrivateKey => "TypeError",
+    deno_crypto::SharedError::ExpectedPublicKey => "TypeError",
+    deno_crypto::SharedError::ExpectedSecretKey => "TypeError",
+    deno_crypto::SharedError::FailedDecodePrivateKey => {
+      "DOMExceptionOperationError"
+    }
+    deno_crypto::SharedError::FailedDecodePublicKey => {
+      "DOMExceptionOperationError"
+    }
+    deno_crypto::SharedError::UnsupportedFormat => {
+      "DOMExceptionNotSupportedError"
+    }
+  }
+}
+
+fn get_crypto_ed25519_error_class(
+  e: &deno_crypto::Ed25519Error,
+) -> &'static str {
+  match e {
+    deno_crypto::Ed25519Error::FailedExport => "DOMExceptionOperationError",
+    deno_crypto::Ed25519Error::Der(_) => "Error",
+    deno_crypto::Ed25519Error::KeyRejected(_) => "Error",
+  }
+}
+
+fn get_crypto_export_key_error_class(e: &ExportKeyError) -> &'static str {
+  match e {
+    ExportKeyError::General(e) => get_crypto_shared_error_class(e),
+    ExportKeyError::Der(_) => "Error",
+    ExportKeyError::UnsupportedNamedCurve => "DOMExceptionNotSupportedError",
+  }
+}
+
+fn get_crypto_generate_key_error_class(e: &GenerateKeyError) -> &'static str {
+  match e {
+    GenerateKeyError::General(e) => get_crypto_shared_error_class(e),
+    GenerateKeyError::BadPublicExponent => "DOMExceptionOperationError",
+    GenerateKeyError::InvalidHMACKeyLength => "DOMExceptionOperationError",
+    GenerateKeyError::FailedRSAKeySerialization => "DOMExceptionOperationError",
+    GenerateKeyError::InvalidAESKeyLength => "DOMExceptionOperationError",
+    GenerateKeyError::FailedRSAKeyGeneration => "DOMExceptionOperationError",
+    GenerateKeyError::FailedECKeyGeneration => "DOMExceptionOperationError",
+    GenerateKeyError::FailedKeyGeneration => "DOMExceptionOperationError",
+  }
+}
+
+fn get_crypto_import_key_error_class(e: &ImportKeyError) -> &'static str {
+  match e {
+    ImportKeyError::General(e) => get_crypto_shared_error_class(e),
+    ImportKeyError::InvalidModulus => "DOMExceptionDataError",
+    ImportKeyError::InvalidPublicExponent => "DOMExceptionDataError",
+    ImportKeyError::InvalidPrivateExponent => "DOMExceptionDataError",
+    ImportKeyError::InvalidFirstPrimeFactor => "DOMExceptionDataError",
+    ImportKeyError::InvalidSecondPrimeFactor => "DOMExceptionDataError",
+    ImportKeyError::InvalidFirstCRTExponent => "DOMExceptionDataError",
+    ImportKeyError::InvalidSecondCRTExponent => "DOMExceptionDataError",
+    ImportKeyError::InvalidCRTCoefficient => "DOMExceptionDataError",
+    ImportKeyError::InvalidB64Coordinate => "DOMExceptionDataError",
+    ImportKeyError::InvalidRSAPublicKey => "DOMExceptionDataError",
+    ImportKeyError::InvalidRSAPrivateKey => "DOMExceptionDataError",
+    ImportKeyError::UnsupportedAlgorithm => "DOMExceptionDataError",
+    ImportKeyError::PublicKeyTooLong => "DOMExceptionDataError",
+    ImportKeyError::PrivateKeyTooLong => "DOMExceptionDataError",
+    ImportKeyError::InvalidP256ECPoint => "DOMExceptionDataError",
+    ImportKeyError::InvalidP384ECPoint => "DOMExceptionDataError",
+    ImportKeyError::InvalidP521ECPoint => "DOMExceptionDataError",
+    ImportKeyError::UnsupportedNamedCurve => "DOMExceptionDataError",
+    ImportKeyError::CurveMismatch => "DOMExceptionDataError",
+    ImportKeyError::InvalidKeyData => "DOMExceptionDataError",
+    ImportKeyError::InvalidJWKPrivateKey => "DOMExceptionDataError",
+    ImportKeyError::EllipticCurve(_) => "DOMExceptionDataError",
+    ImportKeyError::ExpectedValidPkcs8Data => "DOMExceptionDataError",
+    ImportKeyError::MalformedParameters => "DOMExceptionDataError",
+    ImportKeyError::Spki(_) => "DOMExceptionDataError",
+    ImportKeyError::InvalidP256ECSPKIData => "DOMExceptionDataError",
+    ImportKeyError::InvalidP384ECSPKIData => "DOMExceptionDataError",
+    ImportKeyError::InvalidP521ECSPKIData => "DOMExceptionDataError",
+    ImportKeyError::Der(_) => "DOMExceptionDataError",
+  }
+}
+
+fn get_crypto_x448_error_class(e: &deno_crypto::X448Error) -> &'static str {
+  match e {
+    deno_crypto::X448Error::FailedExport => "DOMExceptionOperationError",
+    deno_crypto::X448Error::Der(_) => "Error",
+  }
+}
+
+fn get_crypto_x25519_error_class(e: &deno_crypto::X25519Error) -> &'static str {
+  match e {
+    deno_crypto::X25519Error::FailedExport => "DOMExceptionOperationError",
+    deno_crypto::X25519Error::Der(_) => "Error",
+  }
+}
+
+fn get_crypto_error_class(e: &deno_crypto::Error) -> &'static str {
+  match e {
+    deno_crypto::Error::Der(_) => "Error",
+    deno_crypto::Error::JoinError(_) => "Error",
+    deno_crypto::Error::MissingArgumentHash => "TypeError",
+    deno_crypto::Error::MissingArgumentSaltLength => "TypeError",
+    deno_crypto::Error::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+    deno_crypto::Error::UnsupportedAlgorithm => "TypeError",
+    deno_crypto::Error::KeyRejected(_) => "Error",
+    deno_crypto::Error::RSA(_) => "Error",
+    deno_crypto::Error::Pkcs1(_) => "Error",
+    deno_crypto::Error::Unspecified(_) => "Error",
+    deno_crypto::Error::InvalidKeyFormat => "TypeError",
+    deno_crypto::Error::MissingArgumentPublicKey => "TypeError",
+    deno_crypto::Error::P256Ecdsa(_) => "Error",
+    deno_crypto::Error::DecodePrivateKey => "TypeError",
+    deno_crypto::Error::MissingArgumentNamedCurve => "TypeError",
+    deno_crypto::Error::MissingArgumentInfo => "TypeError",
+    deno_crypto::Error::HKDFLengthTooLarge => "DOMExceptionOperationError",
+    deno_crypto::Error::General(e) => get_crypto_shared_error_class(e),
+    deno_crypto::Error::Base64Decode(_) => "Error",
+    deno_crypto::Error::DataInvalidSize => "TypeError",
+    deno_crypto::Error::InvalidKeyLength => "TypeError",
+    deno_crypto::Error::EncryptionError => "DOMExceptionOperationError",
+    deno_crypto::Error::DecryptionError => "DOMExceptionOperationError",
+    deno_crypto::Error::ArrayBufferViewLengthExceeded(_) => {
+      "DOMExceptionQuotaExceededError"
+    }
+  }
+}
+
+fn get_napi_error_class(e: &NApiError) -> &'static str {
+  match e {
+    NApiError::InvalidPath
+    | NApiError::LibLoading(_)
+    | NApiError::ModuleNotFound(_) => "TypeError",
+    NApiError::Permission(e) => get_permission_check_error_class(e),
+  }
+}
+
+fn get_web_error_class(e: &WebError) -> &'static str {
+  match e {
+    WebError::Base64Decode => "DOMExceptionInvalidCharacterError",
+    WebError::InvalidEncodingLabel(_) => "RangeError",
+    WebError::BufferTooLong => "TypeError",
+    WebError::ValueTooLarge => "RangeError",
+    WebError::BufferTooSmall => "RangeError",
+    WebError::DataInvalid => "TypeError",
+    WebError::DataError(_) => "Error",
+  }
+}
+
+fn get_web_compression_error_class(e: &CompressionError) -> &'static str {
+  match e {
+    CompressionError::UnsupportedFormat => "TypeError",
+    CompressionError::ResourceClosed => "TypeError",
+    CompressionError::IoTypeError(_) => "TypeError",
+    CompressionError::Io(e) => get_io_error_class(e),
+  }
+}
+
+fn get_web_message_port_error_class(e: &MessagePortError) -> &'static str {
+  match e {
+    MessagePortError::InvalidTransfer => "TypeError",
+    MessagePortError::NotReady => "TypeError",
+    MessagePortError::TransferSelf => "TypeError",
+    MessagePortError::Canceled(e) => {
+      let io_err: io::Error = e.to_owned().into();
+      get_io_error_class(&io_err)
+    }
+    MessagePortError::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+  }
+}
+
+fn get_web_stream_resource_error_class(
+  e: &StreamResourceError,
+) -> &'static str {
+  match e {
+    StreamResourceError::Canceled(e) => {
+      let io_err: io::Error = e.to_owned().into();
+      get_io_error_class(&io_err)
+    }
+    StreamResourceError::Js(_) => "TypeError",
+  }
+}
+
+fn get_web_blob_error_class(e: &BlobError) -> &'static str {
+  match e {
+    BlobError::BlobPartNotFound => "TypeError",
+    BlobError::SizeLargerThanBlobPart => "TypeError",
+    BlobError::BlobURLsNotSupported => "TypeError",
+    BlobError::Url(_) => "Error",
+  }
+}
+
+fn get_ffi_repr_error_class(e: &ReprError) -> &'static str {
+  match e {
+    ReprError::InvalidOffset => "TypeError",
+    ReprError::InvalidArrayBuffer => "TypeError",
+    ReprError::DestinationLengthTooShort => "RangeError",
+    ReprError::InvalidCString => "TypeError",
+    ReprError::CStringTooLong => "TypeError",
+    ReprError::InvalidBool => "TypeError",
+    ReprError::InvalidU8 => "TypeError",
+    ReprError::InvalidI8 => "TypeError",
+    ReprError::InvalidU16 => "TypeError",
+    ReprError::InvalidI16 => "TypeError",
+    ReprError::InvalidU32 => "TypeError",
+    ReprError::InvalidI32 => "TypeError",
+    ReprError::InvalidU64 => "TypeError",
+    ReprError::InvalidI64 => "TypeError",
+    ReprError::InvalidF32 => "TypeError",
+    ReprError::InvalidF64 => "TypeError",
+    ReprError::InvalidPointer => "TypeError",
+    ReprError::Permission(e) => get_permission_check_error_class(e),
+  }
+}
+
+fn get_ffi_dlfcn_error_class(e: &DlfcnError) -> &'static str {
+  match e {
+    DlfcnError::RegisterSymbol { .. } => "Error",
+    DlfcnError::Dlopen(_) => "Error",
+    DlfcnError::Permission(e) => get_permission_check_error_class(e),
+    DlfcnError::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+  }
+}
+
+fn get_ffi_static_error_class(e: &StaticError) -> &'static str {
+  match e {
+    StaticError::Dlfcn(e) => get_ffi_dlfcn_error_class(e),
+    StaticError::InvalidTypeVoid => "TypeError",
+    StaticError::InvalidTypeStruct => "TypeError",
+    StaticError::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+  }
+}
+
+fn get_ffi_callback_error_class(e: &CallbackError) -> &'static str {
+  match e {
+    CallbackError::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+    CallbackError::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+    CallbackError::Permission(e) => get_permission_check_error_class(e),
+  }
+}
+
+fn get_ffi_call_error_class(e: &CallError) -> &'static str {
+  match e {
+    CallError::IR(_) => "TypeError",
+    CallError::NonblockingCallFailure(_) => "Error",
+    CallError::InvalidSymbol(_) => "TypeError",
+    CallError::Permission(e) => get_permission_check_error_class(e),
+    CallError::Callback(e) => get_ffi_callback_error_class(e),
+    CallError::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+  }
+}
+
+fn get_webstorage_class_name(e: &WebStorageError) -> &'static str {
+  match e {
+    WebStorageError::ContextNotSupported => "DOMExceptionNotSupportedError",
+    WebStorageError::Sqlite(_) => "Error",
+    WebStorageError::Io(e) => get_io_error_class(e),
+    WebStorageError::StorageExceeded => "DOMExceptionQuotaExceededError",
+  }
+}
+
+fn get_tls_error_class(e: &TlsError) -> &'static str {
+  match e {
+    TlsError::Rustls(_) => "Error",
+    TlsError::UnableAddPemFileToCert(e) => get_io_error_class(e),
+    TlsError::CertInvalid
+    | TlsError::CertsNotFound
+    | TlsError::KeysNotFound
+    | TlsError::KeyDecode => "InvalidData",
+  }
+}
+
+pub fn get_cron_error_class(e: &CronError) -> &'static str {
+  match e {
+    CronError::Resource(e) => {
+      deno_core::error::get_custom_error_class(e).unwrap_or("Error")
+    }
+    CronError::NameExceeded(_) => "TypeError",
+    CronError::NameInvalid => "TypeError",
+    CronError::AlreadyExists => "TypeError",
+    CronError::TooManyCrons => "TypeError",
+    CronError::InvalidCron => "TypeError",
+    CronError::InvalidBackoff => "TypeError",
+    CronError::AcquireError(_) => "Error",
+    CronError::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+  }
+}
+
+fn get_canvas_error(e: &CanvasError) -> &'static str {
+  match e {
+    CanvasError::UnsupportedColorType(_) => "TypeError",
+    CanvasError::Image(_) => "Error",
+  }
+}
+
+pub fn get_cache_error(error: &CacheError) -> &'static str {
+  match error {
+    CacheError::Sqlite(_) => "Error",
+    CacheError::JoinError(_) => "Error",
+    CacheError::Resource(err) => {
+      deno_core::error::get_custom_error_class(err).unwrap_or("Error")
+    }
+    CacheError::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+    CacheError::Io(err) => get_io_error_class(err),
+  }
+}
+
+fn get_broadcast_channel_error(error: &BroadcastChannelError) -> &'static str {
+  match error {
+    BroadcastChannelError::Resource(err) => {
+      deno_core::error::get_custom_error_class(err).unwrap()
+    }
+    BroadcastChannelError::MPSCSendError(_) => "Error",
+    BroadcastChannelError::BroadcastSendError(_) => "Error",
+    BroadcastChannelError::Other(err) => {
+      get_error_class_name(err).unwrap_or("Error")
+    }
+  }
+}
+
+fn get_fetch_error(error: &FetchError) -> &'static str {
+  match error {
+    FetchError::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+    FetchError::Permission(e) => get_permission_check_error_class(e),
+    FetchError::NetworkError => "TypeError",
+    FetchError::FsNotGet(_) => "TypeError",
+    FetchError::InvalidUrl(_) => "TypeError",
+    FetchError::InvalidHeaderName(_) => "TypeError",
+    FetchError::InvalidHeaderValue(_) => "TypeError",
+    FetchError::DataUrl(_) => "TypeError",
+    FetchError::Base64(_) => "TypeError",
+    FetchError::BlobNotFound => "TypeError",
+    FetchError::SchemeNotSupported(_) => "TypeError",
+    FetchError::RequestCanceled => "TypeError",
+    FetchError::Http(_) => "Error",
+    FetchError::ClientCreate(e) => get_http_client_create_error(e),
+    FetchError::Url(e) => get_url_parse_error_class(e),
+    FetchError::Method(_) => "TypeError",
+    FetchError::ClientSend(_) => "TypeError",
+    FetchError::RequestBuilderHook(_) => "TypeError",
+    FetchError::Io(e) => get_io_error_class(e),
+    FetchError::Hyper(e) => get_hyper_error_class(e),
+  }
+}
+
+fn get_http_client_create_error(error: &HttpClientCreateError) -> &'static str {
+  match error {
+    HttpClientCreateError::Tls(_) => "TypeError",
+    HttpClientCreateError::InvalidUserAgent(_) => "TypeError",
+    HttpClientCreateError::InvalidProxyUrl => "TypeError",
+    HttpClientCreateError::HttpVersionSelectionInvalid => "TypeError",
+    HttpClientCreateError::RootCertStore(_) => "TypeError",
+  }
+}
+
+fn get_websocket_error(error: &WebsocketError) -> &'static str {
+  match error {
+    WebsocketError::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+    WebsocketError::Permission(e) => get_permission_check_error_class(e),
+    WebsocketError::Url(e) => get_url_parse_error_class(e),
+    WebsocketError::Io(e) => get_io_error_class(e),
+    WebsocketError::WebSocket(_) => "TypeError",
+    WebsocketError::ConnectionFailed(_) => "DOMExceptionNetworkError",
+    WebsocketError::Uri(_) => "Error",
+    WebsocketError::Canceled(e) => {
+      let io_err: io::Error = e.to_owned().into();
+      get_io_error_class(&io_err)
+    }
+  }
+}
+
+fn get_websocket_handshake_error(error: &HandshakeError) -> &'static str {
+  match error {
+    HandshakeError::RootStoreError(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    HandshakeError::Tls(e) => get_tls_error_class(e),
+    HandshakeError::MissingPath => "TypeError",
+    HandshakeError::Http(_) => "Error",
+    HandshakeError::InvalidHostname(_) => "TypeError",
+    HandshakeError::Io(e) => get_io_error_class(e),
+    HandshakeError::Rustls(_) => "Error",
+    HandshakeError::H2(_) => "Error",
+    HandshakeError::NoH2Alpn => "Error",
+    HandshakeError::InvalidStatusCode(_) => "Error",
+    HandshakeError::WebSocket(_) => "TypeError",
+    HandshakeError::HeaderName(_) => "TypeError",
+    HandshakeError::HeaderValue(_) => "TypeError",
+  }
+}
+
+fn get_fs_ops_error(error: &FsOpsError) -> &'static str {
+  match error {
+    FsOpsError::Io(e) => get_io_error_class(e),
+    FsOpsError::OperationError(e) => get_fs_error(&e.err),
+    FsOpsError::Permission(e) => get_permission_check_error_class(e),
+    FsOpsError::Resource(e) | FsOpsError::Other(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    FsOpsError::InvalidUtf8(_) => "InvalidData",
+    FsOpsError::StripPrefix(_) => "Error",
+    FsOpsError::Canceled(e) => {
+      let io_err: io::Error = e.to_owned().into();
+      get_io_error_class(&io_err)
+    }
+    FsOpsError::InvalidSeekMode(_) => "TypeError",
+    FsOpsError::InvalidControlCharacter(_) => "Error",
+    FsOpsError::InvalidCharacter(_) => "Error",
+    #[cfg(windows)]
+    FsOpsError::InvalidTrailingCharacter => "Error",
+    FsOpsError::NotCapableAccess { .. } => "NotCapable",
+    FsOpsError::NotCapable(_) => "NotCapable",
+  }
+}
+
+fn get_kv_error(error: &KvError) -> &'static str {
+  match error {
+    KvError::DatabaseHandler(e) | KvError::Resource(e) | KvError::Kv(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    KvError::TooManyRanges(_) => "TypeError",
+    KvError::TooManyEntries(_) => "TypeError",
+    KvError::TooManyChecks(_) => "TypeError",
+    KvError::TooManyMutations(_) => "TypeError",
+    KvError::TooManyKeys(_) => "TypeError",
+    KvError::InvalidLimit => "TypeError",
+    KvError::InvalidBoundaryKey => "TypeError",
+    KvError::KeyTooLargeToRead(_) => "TypeError",
+    KvError::KeyTooLargeToWrite(_) => "TypeError",
+    KvError::TotalMutationTooLarge(_) => "TypeError",
+    KvError::TotalKeyTooLarge(_) => "TypeError",
+    KvError::Io(e) => get_io_error_class(e),
+    KvError::QueueMessageNotFound => "TypeError",
+    KvError::StartKeyNotInKeyspace => "TypeError",
+    KvError::EndKeyNotInKeyspace => "TypeError",
+    KvError::StartKeyGreaterThanEndKey => "TypeError",
+    KvError::InvalidCheck(e) => match e {
+      KvCheckError::InvalidVersionstamp => "TypeError",
+      KvCheckError::Io(e) => get_io_error_class(e),
+    },
+    KvError::InvalidMutation(e) => match e {
+      KvMutationError::BigInt(_) => "Error",
+      KvMutationError::Io(e) => get_io_error_class(e),
+      KvMutationError::InvalidMutationWithValue(_) => "TypeError",
+      KvMutationError::InvalidMutationWithoutValue(_) => "TypeError",
+    },
+    KvError::InvalidEnqueue(e) => get_io_error_class(e),
+    KvError::EmptyKey => "TypeError",
+    KvError::ValueTooLarge(_) => "TypeError",
+    KvError::EnqueuePayloadTooLarge(_) => "TypeError",
+    KvError::InvalidCursor => "TypeError",
+    KvError::CursorOutOfBounds => "TypeError",
+    KvError::InvalidRange => "TypeError",
+  }
+}
+
+fn get_net_error(error: &NetError) -> &'static str {
+  match error {
+    NetError::ListenerClosed => "BadResource",
+    NetError::ListenerBusy => "Busy",
+    NetError::SocketClosed => "BadResource",
+    NetError::SocketClosedNotConnected => "NotConnected",
+    NetError::SocketBusy => "Busy",
+    NetError::Io(e) => get_io_error_class(e),
+    NetError::AcceptTaskOngoing => "Busy",
+    NetError::RootCertStore(e) | NetError::Resource(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    NetError::Permission(e) => get_permission_check_error_class(e),
+    NetError::NoResolvedAddress => "Error",
+    NetError::AddrParse(_) => "Error",
+    NetError::Map(e) => get_net_map_error(e),
+    NetError::Canceled(e) => {
+      let io_err: io::Error = e.to_owned().into();
+      get_io_error_class(&io_err)
+    }
+    NetError::DnsNotFound(_) => "NotFound",
+    NetError::DnsNotConnected(_) => "NotConnected",
+    NetError::DnsTimedOut(_) => "TimedOut",
+    NetError::Dns(_) => "Error",
+    NetError::UnsupportedRecordType => "NotSupported",
+    NetError::InvalidUtf8(_) => "InvalidData",
+    NetError::UnexpectedKeyType => "Error",
+    NetError::InvalidHostname(_) => "TypeError",
+    NetError::TcpStreamBusy => "Busy",
+    NetError::Rustls(_) => "Error",
+    NetError::Tls(e) => get_tls_error_class(e),
+    NetError::ListenTlsRequiresKey => "InvalidData",
+    NetError::Reunite(_) => "Error",
+  }
+}
+
+fn get_net_map_error(error: &deno_net::io::MapError) -> &'static str {
+  match error {
+    deno_net::io::MapError::Io(e) => get_io_error_class(e),
+    deno_net::io::MapError::NoResources => "Error",
+  }
+}
+
+fn get_child_permission_error(e: &ChildPermissionError) -> &'static str {
+  match e {
+    ChildPermissionError::Escalation => "NotCapable",
+    ChildPermissionError::PathResolve(e) => get_path_resolve_error(e),
+    ChildPermissionError::NetDescriptorParse(_) => "URIError",
+    ChildPermissionError::EnvDescriptorParse(_) => "Error",
+    ChildPermissionError::SysDescriptorParse(e) => {
+      get_sys_descriptor_parse_error(e)
+    }
+    ChildPermissionError::RunDescriptorParse(e) => {
+      get_run_descriptor_parse_error(e)
+    }
+  }
+}
+
+fn get_create_worker_error(error: &CreateWorkerError) -> &'static str {
+  match error {
+    CreateWorkerError::ClassicWorkers => "DOMExceptionNotSupportedError",
+    CreateWorkerError::Permission(e) => get_child_permission_error(e),
+    CreateWorkerError::ModuleResolution(e) => {
+      get_module_resolution_error_class(e)
+    }
+    CreateWorkerError::Io(e) => get_io_error_class(e),
+    CreateWorkerError::MessagePort(e) => get_web_message_port_error_class(e),
+  }
+}
+
+fn get_tty_error(error: &TtyError) -> &'static str {
+  match error {
+    TtyError::Resource(e) | TtyError::Other(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    TtyError::Io(e) => get_io_error_class(e),
+    #[cfg(unix)]
+    TtyError::Nix(e) => get_nix_error_class(e),
+  }
+}
+
+fn get_readline_error(error: &ReadlineError) -> &'static str {
+  match error {
+    ReadlineError::Io(e) => get_io_error_class(e),
+    ReadlineError::Eof => "Error",
+    ReadlineError::Interrupted => "Error",
+    #[cfg(unix)]
+    ReadlineError::Errno(e) => get_nix_error_class(e),
+    ReadlineError::WindowResized => "Error",
+    #[cfg(windows)]
+    ReadlineError::Decode(_) => "Error",
+    #[cfg(windows)]
+    ReadlineError::SystemError(_) => "Error",
+    _ => "Error",
+  }
+}
+
+fn get_signal_error(error: &SignalError) -> &'static str {
+  match error {
+    SignalError::InvalidSignalStr(_) => "TypeError",
+    SignalError::InvalidSignalInt(_) => "TypeError",
+    SignalError::SignalNotAllowed(_) => "TypeError",
+    SignalError::Io(e) => get_io_error_class(e),
+  }
+}
+
+fn get_fs_events_error(error: &FsEventsError) -> &'static str {
+  match error {
+    FsEventsError::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+    FsEventsError::Permission(e) => get_permission_check_error_class(e),
+    FsEventsError::Notify(e) => get_notify_error_class(e),
+    FsEventsError::Canceled(e) => {
+      let io_err: io::Error = e.to_owned().into();
+      get_io_error_class(&io_err)
+    }
+  }
+}
+
+fn get_http_start_error(error: &HttpStartError) -> &'static str {
+  match error {
+    HttpStartError::TcpStreamInUse => "Busy",
+    HttpStartError::TlsStreamInUse => "Busy",
+    HttpStartError::UnixSocketInUse => "Busy",
+    HttpStartError::ReuniteTcp(_) => "Error",
+    #[cfg(unix)]
+    HttpStartError::ReuniteUnix(_) => "Error",
+    HttpStartError::Io(e) => get_io_error_class(e),
+    HttpStartError::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+  }
+}
+
+fn get_process_error(error: &ProcessError) -> &'static str {
+  match error {
+    ProcessError::SpawnFailed { error, .. } => get_process_error(error),
+    ProcessError::FailedResolvingCwd(e) | ProcessError::Io(e) => {
+      get_io_error_class(e)
+    }
+    ProcessError::Permission(e) => get_permission_check_error_class(e),
+    ProcessError::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+    ProcessError::BorrowMut(_) => "Error",
+    ProcessError::Which(_) => "Error",
+    ProcessError::ChildProcessAlreadyTerminated => "TypeError",
+    ProcessError::Signal(e) => get_signal_error(e),
+    ProcessError::MissingCmd => "Error",
+    ProcessError::InvalidPid => "TypeError",
+    #[cfg(unix)]
+    ProcessError::Nix(e) => get_nix_error_class(e),
+    ProcessError::RunPermission(e) => match e {
+      CheckRunPermissionError::Permission(e) => {
+        get_permission_check_error_class(e)
+      }
+      CheckRunPermissionError::Other(e) => {
+        get_error_class_name(e).unwrap_or("Error")
+      }
+    },
+  }
+}
+
+fn get_http_error(error: &HttpError) -> &'static str {
+  match error {
+    HttpError::Canceled(e) => {
+      let io_err: io::Error = e.to_owned().into();
+      get_io_error_class(&io_err)
+    }
+    HttpError::HyperV014(e) => get_hyper_v014_error_class(e),
+    HttpError::InvalidHeaderName(_) => "Error",
+    HttpError::InvalidHeaderValue(_) => "Error",
+    HttpError::Http(_) => "Error",
+    HttpError::ResponseHeadersAlreadySent => "Http",
+    HttpError::ConnectionClosedWhileSendingResponse => "Http",
+    HttpError::AlreadyInUse => "Http",
+    HttpError::Io(e) => get_io_error_class(e),
+    HttpError::NoResponseHeaders => "Http",
+    HttpError::ResponseAlreadyCompleted => "Http",
+    HttpError::UpgradeBodyUsed => "Http",
+    HttpError::Resource(e) | HttpError::Other(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+  }
+}
+
+fn get_http_next_error(error: &HttpNextError) -> &'static str {
+  match error {
+    HttpNextError::Io(e) => get_io_error_class(e),
+    HttpNextError::WebSocketUpgrade(e) => get_websocket_upgrade_error(e),
+    HttpNextError::Hyper(e) => get_hyper_error_class(e),
+    HttpNextError::JoinError(_) => "Error",
+    HttpNextError::Canceled(e) => {
+      let io_err: io::Error = e.to_owned().into();
+      get_io_error_class(&io_err)
+    }
+    HttpNextError::UpgradeUnavailable(_) => "Error",
+    HttpNextError::HttpPropertyExtractor(e) | HttpNextError::Resource(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+  }
+}
+
+fn get_websocket_upgrade_error(error: &WebSocketUpgradeError) -> &'static str {
+  match error {
+    WebSocketUpgradeError::InvalidHeaders => "Http",
+    WebSocketUpgradeError::HttpParse(_) => "Error",
+    WebSocketUpgradeError::Http(_) => "Error",
+    WebSocketUpgradeError::Utf8(_) => "Error",
+    WebSocketUpgradeError::InvalidHeaderName(_) => "Error",
+    WebSocketUpgradeError::InvalidHeaderValue(_) => "Error",
+    WebSocketUpgradeError::InvalidHttpStatusLine => "Http",
+    WebSocketUpgradeError::UpgradeBufferAlreadyCompleted => "Http",
+  }
+}
+
+fn get_fs_error(e: &FsError) -> &'static str {
+  match &e {
+    FsError::Io(e) => get_io_error_class(e),
+    FsError::FileBusy => "Busy",
+    FsError::NotSupported => "NotSupported",
+    FsError::NotCapable(_) => "NotCapable",
+  }
+}
+
+mod node {
+  use super::get_error_class_name;
+  use super::get_io_error_class;
+  use super::get_permission_check_error_class;
+  use super::get_serde_json_error_class;
+  use super::get_url_parse_error_class;
+  pub use deno_node::ops::blocklist::BlocklistError;
+  pub use deno_node::ops::crypto::cipher::CipherContextError;
+  pub use deno_node::ops::crypto::cipher::CipherError;
+  pub use deno_node::ops::crypto::cipher::DecipherContextError;
+  pub use deno_node::ops::crypto::cipher::DecipherError;
+  pub use deno_node::ops::crypto::digest::HashError;
+  pub use deno_node::ops::crypto::keys::AsymmetricPrivateKeyDerError;
+  pub use deno_node::ops::crypto::keys::AsymmetricPrivateKeyError;
+  pub use deno_node::ops::crypto::keys::AsymmetricPublicKeyDerError;
+  pub use deno_node::ops::crypto::keys::AsymmetricPublicKeyError;
+  pub use deno_node::ops::crypto::keys::AsymmetricPublicKeyJwkError;
+  pub use deno_node::ops::crypto::keys::EcJwkError;
+  pub use deno_node::ops::crypto::keys::EdRawError;
+  pub use deno_node::ops::crypto::keys::ExportPrivateKeyPemError;
+  pub use deno_node::ops::crypto::keys::ExportPublicKeyPemError;
+  pub use deno_node::ops::crypto::keys::GenerateRsaPssError;
+  pub use deno_node::ops::crypto::keys::RsaJwkError;
+  pub use deno_node::ops::crypto::keys::RsaPssParamsParseError;
+  pub use deno_node::ops::crypto::keys::X509PublicKeyError;
+  pub use deno_node::ops::crypto::sign::KeyObjectHandlePrehashedSignAndVerifyError;
+  pub use deno_node::ops::crypto::x509::X509Error;
+  pub use deno_node::ops::crypto::DiffieHellmanError;
+  pub use deno_node::ops::crypto::EcdhEncodePubKey;
+  pub use deno_node::ops::crypto::HkdfError;
+  pub use deno_node::ops::crypto::Pbkdf2Error;
+  pub use deno_node::ops::crypto::PrivateEncryptDecryptError;
+  pub use deno_node::ops::crypto::ScryptAsyncError;
+  pub use deno_node::ops::crypto::SignEd25519Error;
+  pub use deno_node::ops::crypto::VerifyEd25519Error;
+  pub use deno_node::ops::fs::FsError;
+  pub use deno_node::ops::http2::Http2Error;
+  pub use deno_node::ops::idna::IdnaError;
+  pub use deno_node::ops::ipc::IpcError;
+  pub use deno_node::ops::ipc::IpcJsonStreamError;
+  use deno_node::ops::os::priority::PriorityError;
+  pub use deno_node::ops::os::OsError;
+  pub use deno_node::ops::require::RequireError;
+  pub use deno_node::ops::worker_threads::WorkerThreadsFilenameError;
+  pub use deno_node::ops::zlib::brotli::BrotliError;
+  pub use deno_node::ops::zlib::mode::ModeError;
+  pub use deno_node::ops::zlib::ZlibError;
+
+  pub fn get_blocklist_error(error: &BlocklistError) -> &'static str {
+    match error {
+      BlocklistError::AddrParse(_) => "Error",
+      BlocklistError::IpNetwork(_) => "Error",
+      BlocklistError::InvalidAddress => "Error",
+      BlocklistError::IpVersionMismatch => "Error",
+    }
+  }
+
+  pub fn get_fs_error(error: &FsError) -> &'static str {
+    match error {
+      FsError::Permission(e) => get_permission_check_error_class(e),
+      FsError::Io(e) => get_io_error_class(e),
+      #[cfg(windows)]
+      FsError::PathHasNoRoot => "Error",
+      #[cfg(not(any(unix, windows)))]
+      FsError::UnsupportedPlatform => "Error",
+      FsError::Fs(e) => super::get_fs_error(e),
+    }
+  }
+
+  pub fn get_idna_error(error: &IdnaError) -> &'static str {
+    match error {
+      IdnaError::InvalidInput => "RangeError",
+      IdnaError::InputTooLong => "Error",
+      IdnaError::IllegalInput => "RangeError",
+    }
+  }
+
+  pub fn get_ipc_json_stream_error(error: &IpcJsonStreamError) -> &'static str {
+    match error {
+      IpcJsonStreamError::Io(e) => get_io_error_class(e),
+      IpcJsonStreamError::SimdJson(_) => "Error",
+    }
+  }
+
+  pub fn get_ipc_error(error: &IpcError) -> &'static str {
+    match error {
+      IpcError::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+      IpcError::IpcJsonStream(e) => get_ipc_json_stream_error(e),
+      IpcError::Canceled(e) => {
+        let io_err: std::io::Error = e.to_owned().into();
+        get_io_error_class(&io_err)
+      }
+      IpcError::SerdeJson(e) => get_serde_json_error_class(e),
+    }
+  }
+
+  pub fn get_worker_threads_filename_error(
+    error: &WorkerThreadsFilenameError,
+  ) -> &'static str {
+    match error {
+      WorkerThreadsFilenameError::Permission(e) => {
+        get_error_class_name(e).unwrap_or("Error")
+      }
+      WorkerThreadsFilenameError::UrlParse(e) => get_url_parse_error_class(e),
+      WorkerThreadsFilenameError::InvalidRelativeUrl => "Error",
+      WorkerThreadsFilenameError::UrlFromPathString => "Error",
+      WorkerThreadsFilenameError::UrlToPathString => "Error",
+      WorkerThreadsFilenameError::UrlToPath => "Error",
+      WorkerThreadsFilenameError::FileNotFound(_) => "Error",
+      WorkerThreadsFilenameError::Fs(e) => super::get_fs_error(e),
+    }
+  }
+
+  pub fn get_require_error(error: &RequireError) -> &'static str {
+    match error {
+      RequireError::UrlParse(e) => get_url_parse_error_class(e),
+      RequireError::Permission(e) => get_error_class_name(e).unwrap_or("Error"),
+      RequireError::PackageExportsResolve(_)
+      | RequireError::PackageJsonLoad(_)
+      | RequireError::ClosestPkgJson(_)
+      | RequireError::FilePathConversion(_)
+      | RequireError::UrlConversion(_)
+      | RequireError::ReadModule(_)
+      | RequireError::PackageImportsResolve(_) => "Error",
+      RequireError::Fs(e) | RequireError::UnableToGetCwd(e) => {
+        super::get_fs_error(e)
+      }
+    }
+  }
+
+  pub fn get_http2_error(error: &Http2Error) -> &'static str {
+    match error {
+      Http2Error::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+      Http2Error::UrlParse(e) => get_url_parse_error_class(e),
+      Http2Error::H2(_) => "Error",
+    }
+  }
+
+  pub fn get_os_error(error: &OsError) -> &'static str {
+    match error {
+      OsError::Priority(e) => match e {
+        PriorityError::Io(e) => get_io_error_class(e),
+        #[cfg(windows)]
+        PriorityError::InvalidPriority => "TypeError",
+      },
+      OsError::Permission(e) => get_permission_check_error_class(e),
+      OsError::FailedToGetCpuInfo => "TypeError",
+      OsError::FailedToGetUserInfo(e) => get_io_error_class(e),
+    }
+  }
+
+  pub fn get_brotli_error(error: &BrotliError) -> &'static str {
+    match error {
+      BrotliError::InvalidEncoderMode => "TypeError",
+      BrotliError::CompressFailed => "TypeError",
+      BrotliError::DecompressFailed => "TypeError",
+      BrotliError::Join(_) => "Error",
+      BrotliError::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+      BrotliError::Io(e) => get_io_error_class(e),
+    }
+  }
+
+  pub fn get_mode_error(_: &ModeError) -> &'static str {
+    "Error"
+  }
+
+  pub fn get_zlib_error(e: &ZlibError) -> &'static str {
+    match e {
+      ZlibError::NotInitialized => "TypeError",
+      ZlibError::Mode(e) => get_mode_error(e),
+      ZlibError::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+    }
+  }
+
+  pub fn get_crypto_cipher_context_error(
+    e: &CipherContextError,
+  ) -> &'static str {
+    match e {
+      CipherContextError::ContextInUse => "TypeError",
+      CipherContextError::Cipher(e) => get_crypto_cipher_error(e),
+      CipherContextError::Resource(e) => {
+        get_error_class_name(e).unwrap_or("Error")
+      }
+    }
+  }
+
+  pub fn get_crypto_cipher_error(e: &CipherError) -> &'static str {
+    match e {
+      CipherError::InvalidIvLength => "TypeError",
+      CipherError::InvalidKeyLength => "RangeError",
+      CipherError::InvalidInitializationVector => "TypeError",
+      CipherError::CannotPadInputData => "TypeError",
+      CipherError::UnknownCipher(_) => "TypeError",
+    }
+  }
+
+  pub fn get_crypto_decipher_context_error(
+    e: &DecipherContextError,
+  ) -> &'static str {
+    match e {
+      DecipherContextError::ContextInUse => "TypeError",
+      DecipherContextError::Decipher(e) => get_crypto_decipher_error(e),
+      DecipherContextError::Resource(e) => {
+        get_error_class_name(e).unwrap_or("Error")
+      }
+    }
+  }
+
+  pub fn get_crypto_decipher_error(e: &DecipherError) -> &'static str {
+    match e {
+      DecipherError::InvalidIvLength => "TypeError",
+      DecipherError::InvalidKeyLength => "RangeError",
+      DecipherError::InvalidInitializationVector => "TypeError",
+      DecipherError::CannotUnpadInputData => "TypeError",
+      DecipherError::DataAuthenticationFailed => "TypeError",
+      DecipherError::SetAutoPaddingFalseAes128GcmUnsupported => "TypeError",
+      DecipherError::SetAutoPaddingFalseAes256GcmUnsupported => "TypeError",
+      DecipherError::UnknownCipher(_) => "TypeError",
+    }
+  }
+
+  pub fn get_x509_error(_: &X509Error) -> &'static str {
+    "Error"
+  }
+
+  pub fn get_crypto_key_object_handle_prehashed_sign_and_verify_error(
+    e: &KeyObjectHandlePrehashedSignAndVerifyError,
+  ) -> &'static str {
+    match e {
+      KeyObjectHandlePrehashedSignAndVerifyError::InvalidDsaSignatureEncoding => "TypeError",
+      KeyObjectHandlePrehashedSignAndVerifyError::KeyIsNotPrivate => "TypeError",
+      KeyObjectHandlePrehashedSignAndVerifyError::DigestNotAllowedForRsaSignature(_) => "TypeError",
+      KeyObjectHandlePrehashedSignAndVerifyError::FailedToSignDigestWithRsa => "Error",
+      KeyObjectHandlePrehashedSignAndVerifyError::DigestNotAllowedForRsaPssSignature(_) => "TypeError",
+      KeyObjectHandlePrehashedSignAndVerifyError::FailedToSignDigestWithRsaPss => "Error",
+      KeyObjectHandlePrehashedSignAndVerifyError::FailedToSignDigestWithDsa => "TypeError",
+      KeyObjectHandlePrehashedSignAndVerifyError::RsaPssHashAlgorithmUnsupported => "TypeError",
+      KeyObjectHandlePrehashedSignAndVerifyError::PrivateKeyDisallowsUsage { .. } => "TypeError",
+      KeyObjectHandlePrehashedSignAndVerifyError::FailedToSignDigest => "TypeError",
+      KeyObjectHandlePrehashedSignAndVerifyError::X25519KeyCannotBeUsedForSigning => "TypeError",
+      KeyObjectHandlePrehashedSignAndVerifyError::Ed25519KeyCannotBeUsedForPrehashedSigning => "TypeError",
+      KeyObjectHandlePrehashedSignAndVerifyError::DhKeyCannotBeUsedForSigning => "TypeError",
+      KeyObjectHandlePrehashedSignAndVerifyError::KeyIsNotPublicOrPrivate => "TypeError",
+      KeyObjectHandlePrehashedSignAndVerifyError::InvalidDsaSignature => "TypeError",
+      KeyObjectHandlePrehashedSignAndVerifyError::X25519KeyCannotBeUsedForVerification => "TypeError",
+      KeyObjectHandlePrehashedSignAndVerifyError::Ed25519KeyCannotBeUsedForPrehashedVerification => "TypeError",
+      KeyObjectHandlePrehashedSignAndVerifyError::DhKeyCannotBeUsedForVerification => "TypeError",
+    }
+  }
+
+  pub fn get_crypto_hash_error(_: &HashError) -> &'static str {
+    "Error"
+  }
+
+  pub fn get_asymmetric_public_key_jwk_error(
+    e: &AsymmetricPublicKeyJwkError,
+  ) -> &'static str {
+    match e {
+      AsymmetricPublicKeyJwkError::UnsupportedJwkEcCurveP224 => "TypeError",
+      AsymmetricPublicKeyJwkError::JwkExportNotImplementedForKeyType => {
+        "TypeError"
+      }
+      AsymmetricPublicKeyJwkError::KeyIsNotAsymmetricPublicKey => "TypeError",
+    }
+  }
+
+  pub fn get_generate_rsa_pss_error(_: &GenerateRsaPssError) -> &'static str {
+    "TypeError"
+  }
+
+  pub fn get_asymmetric_private_key_der_error(
+    e: &AsymmetricPrivateKeyDerError,
+  ) -> &'static str {
+    match e {
+      AsymmetricPrivateKeyDerError::KeyIsNotAsymmetricPrivateKey => "TypeError",
+      AsymmetricPrivateKeyDerError::InvalidRsaPrivateKey => "TypeError",
+      AsymmetricPrivateKeyDerError::ExportingNonRsaPrivateKeyAsPkcs1Unsupported => "TypeError",
+      AsymmetricPrivateKeyDerError::InvalidEcPrivateKey => "TypeError",
+      AsymmetricPrivateKeyDerError::ExportingNonEcPrivateKeyAsSec1Unsupported => "TypeError",
+      AsymmetricPrivateKeyDerError::ExportingNonRsaPssPrivateKeyAsPkcs8Unsupported => "Error",
+      AsymmetricPrivateKeyDerError::InvalidDsaPrivateKey => "TypeError",
+      AsymmetricPrivateKeyDerError::InvalidX25519PrivateKey => "TypeError",
+      AsymmetricPrivateKeyDerError::InvalidEd25519PrivateKey => "TypeError",
+      AsymmetricPrivateKeyDerError::InvalidDhPrivateKey => "TypeError",
+      AsymmetricPrivateKeyDerError::UnsupportedKeyType(_) => "TypeError",
+    }
+  }
+
+  pub fn get_asymmetric_public_key_der_error(
+    _: &AsymmetricPublicKeyDerError,
+  ) -> &'static str {
+    "TypeError"
+  }
+
+  pub fn get_export_public_key_pem_error(
+    e: &ExportPublicKeyPemError,
+  ) -> &'static str {
+    match e {
+      ExportPublicKeyPemError::AsymmetricPublicKeyDer(e) => {
+        get_asymmetric_public_key_der_error(e)
+      }
+      ExportPublicKeyPemError::VeryLargeData => "TypeError",
+      ExportPublicKeyPemError::Der(_) => "Error",
+    }
+  }
+
+  pub fn get_export_private_key_pem_error(
+    e: &ExportPrivateKeyPemError,
+  ) -> &'static str {
+    match e {
+      ExportPrivateKeyPemError::AsymmetricPublicKeyDer(e) => {
+        get_asymmetric_private_key_der_error(e)
+      }
+      ExportPrivateKeyPemError::VeryLargeData => "TypeError",
+      ExportPrivateKeyPemError::Der(_) => "Error",
+    }
+  }
+
+  pub fn get_x509_public_key_error(e: &X509PublicKeyError) -> &'static str {
+    match e {
+      X509PublicKeyError::X509(_) => "Error",
+      X509PublicKeyError::Rsa(_) => "Error",
+      X509PublicKeyError::Asn1(_) => "Error",
+      X509PublicKeyError::Ec(_) => "Error",
+      X509PublicKeyError::UnsupportedEcNamedCurve => "TypeError",
+      X509PublicKeyError::MissingEcParameters => "TypeError",
+      X509PublicKeyError::MalformedDssPublicKey => "TypeError",
+      X509PublicKeyError::UnsupportedX509KeyType => "TypeError",
+    }
+  }
+
+  pub fn get_rsa_jwk_error(e: &RsaJwkError) -> &'static str {
+    match e {
+      RsaJwkError::Base64(_) => "Error",
+      RsaJwkError::Rsa(_) => "Error",
+      RsaJwkError::MissingRsaPrivateComponent => "TypeError",
+    }
+  }
+
+  pub fn get_ec_jwk_error(e: &EcJwkError) -> &'static str {
+    match e {
+      EcJwkError::Ec(_) => "Error",
+      EcJwkError::UnsupportedCurve(_) => "TypeError",
+    }
+  }
+
+  pub fn get_ed_raw_error(e: &EdRawError) -> &'static str {
+    match e {
+      EdRawError::Ed25519Signature(_) => "Error",
+      EdRawError::InvalidEd25519Key => "TypeError",
+      EdRawError::UnsupportedCurve => "TypeError",
+    }
+  }
+
+  pub fn get_pbkdf2_error(e: &Pbkdf2Error) -> &'static str {
+    match e {
+      Pbkdf2Error::UnsupportedDigest(_) => "TypeError",
+      Pbkdf2Error::Join(_) => "Error",
+    }
+  }
+
+  pub fn get_scrypt_async_error(e: &ScryptAsyncError) -> &'static str {
+    match e {
+      ScryptAsyncError::Join(_) => "Error",
+      ScryptAsyncError::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+    }
+  }
+
+  pub fn get_hkdf_error_error(e: &HkdfError) -> &'static str {
+    match e {
+      HkdfError::ExpectedSecretKey => "TypeError",
+      HkdfError::HkdfExpandFailed => "TypeError",
+      HkdfError::UnsupportedDigest(_) => "TypeError",
+      HkdfError::Join(_) => "Error",
+    }
+  }
+
+  pub fn get_rsa_pss_params_parse_error(
+    _: &RsaPssParamsParseError,
+  ) -> &'static str {
+    "TypeError"
+  }
+
+  pub fn get_asymmetric_private_key_error(
+    e: &AsymmetricPrivateKeyError,
+  ) -> &'static str {
+    match e {
+      AsymmetricPrivateKeyError::InvalidPemPrivateKeyInvalidUtf8(_) => "TypeError",
+      AsymmetricPrivateKeyError::InvalidEncryptedPemPrivateKey => "TypeError",
+      AsymmetricPrivateKeyError::InvalidPemPrivateKey => "TypeError",
+      AsymmetricPrivateKeyError::EncryptedPrivateKeyRequiresPassphraseToDecrypt => "TypeError",
+      AsymmetricPrivateKeyError::InvalidPkcs1PrivateKey => "TypeError",
+      AsymmetricPrivateKeyError::InvalidSec1PrivateKey => "TypeError",
+      AsymmetricPrivateKeyError::UnsupportedPemLabel(_) => "TypeError",
+      AsymmetricPrivateKeyError::RsaPssParamsParse(e) => get_rsa_pss_params_parse_error(e),
+      AsymmetricPrivateKeyError::InvalidEncryptedPkcs8PrivateKey => "TypeError",
+      AsymmetricPrivateKeyError::InvalidPkcs8PrivateKey => "TypeError",
+      AsymmetricPrivateKeyError::Pkcs1PrivateKeyDoesNotSupportEncryptionWithPassphrase => "TypeError",
+      AsymmetricPrivateKeyError::Sec1PrivateKeyDoesNotSupportEncryptionWithPassphrase => "TypeError",
+      AsymmetricPrivateKeyError::UnsupportedEcNamedCurve => "TypeError",
+      AsymmetricPrivateKeyError::InvalidPrivateKey => "TypeError",
+      AsymmetricPrivateKeyError::InvalidDsaPrivateKey => "TypeError",
+      AsymmetricPrivateKeyError::MalformedOrMissingNamedCurveInEcParameters => "TypeError",
+      AsymmetricPrivateKeyError::UnsupportedKeyType(_) => "TypeError",
+      AsymmetricPrivateKeyError::UnsupportedKeyFormat(_) => "TypeError",
+      AsymmetricPrivateKeyError::InvalidX25519PrivateKey => "TypeError",
+      AsymmetricPrivateKeyError::X25519PrivateKeyIsWrongLength => "TypeError",
+      AsymmetricPrivateKeyError::InvalidEd25519PrivateKey => "TypeError",
+      AsymmetricPrivateKeyError::MissingDhParameters => "TypeError",
+      AsymmetricPrivateKeyError::UnsupportedPrivateKeyOid => "TypeError",
+    }
+  }
+
+  pub fn get_asymmetric_public_key_error(
+    e: &AsymmetricPublicKeyError,
+  ) -> &'static str {
+    match e {
+      AsymmetricPublicKeyError::InvalidPemPrivateKeyInvalidUtf8(_) => {
+        "TypeError"
+      }
+      AsymmetricPublicKeyError::InvalidPemPublicKey => "TypeError",
+      AsymmetricPublicKeyError::InvalidPkcs1PublicKey => "TypeError",
+      AsymmetricPublicKeyError::AsymmetricPrivateKey(e) => {
+        get_asymmetric_private_key_error(e)
+      }
+      AsymmetricPublicKeyError::InvalidX509Certificate => "TypeError",
+      AsymmetricPublicKeyError::X509(_) => "Error",
+      AsymmetricPublicKeyError::X509PublicKey(e) => {
+        get_x509_public_key_error(e)
+      }
+      AsymmetricPublicKeyError::UnsupportedPemLabel(_) => "TypeError",
+      AsymmetricPublicKeyError::InvalidSpkiPublicKey => "TypeError",
+      AsymmetricPublicKeyError::UnsupportedKeyType(_) => "TypeError",
+      AsymmetricPublicKeyError::UnsupportedKeyFormat(_) => "TypeError",
+      AsymmetricPublicKeyError::Spki(_) => "Error",
+      AsymmetricPublicKeyError::Pkcs1(_) => "Error",
+      AsymmetricPublicKeyError::RsaPssParamsParse(_) => "TypeError",
+      AsymmetricPublicKeyError::MalformedDssPublicKey => "TypeError",
+      AsymmetricPublicKeyError::MalformedOrMissingNamedCurveInEcParameters => {
+        "TypeError"
+      }
+      AsymmetricPublicKeyError::MalformedOrMissingPublicKeyInEcSpki => {
+        "TypeError"
+      }
+      AsymmetricPublicKeyError::Ec(_) => "Error",
+      AsymmetricPublicKeyError::UnsupportedEcNamedCurve => "TypeError",
+      AsymmetricPublicKeyError::MalformedOrMissingPublicKeyInX25519Spki => {
+        "TypeError"
+      }
+      AsymmetricPublicKeyError::X25519PublicKeyIsTooShort => "TypeError",
+      AsymmetricPublicKeyError::InvalidEd25519PublicKey => "TypeError",
+      AsymmetricPublicKeyError::MissingDhParameters => "TypeError",
+      AsymmetricPublicKeyError::MalformedDhParameters => "TypeError",
+      AsymmetricPublicKeyError::MalformedOrMissingPublicKeyInDhSpki => {
+        "TypeError"
+      }
+      AsymmetricPublicKeyError::UnsupportedPrivateKeyOid => "TypeError",
+    }
+  }
+
+  pub fn get_private_encrypt_decrypt_error(
+    e: &PrivateEncryptDecryptError,
+  ) -> &'static str {
+    match e {
+      PrivateEncryptDecryptError::Pkcs8(_) => "Error",
+      PrivateEncryptDecryptError::Spki(_) => "Error",
+      PrivateEncryptDecryptError::Utf8(_) => "Error",
+      PrivateEncryptDecryptError::Rsa(_) => "Error",
+      PrivateEncryptDecryptError::UnknownPadding => "TypeError",
+    }
+  }
+
+  pub fn get_ecdh_encode_pub_key_error(e: &EcdhEncodePubKey) -> &'static str {
+    match e {
+      EcdhEncodePubKey::InvalidPublicKey => "TypeError",
+      EcdhEncodePubKey::UnsupportedCurve => "TypeError",
+      EcdhEncodePubKey::Sec1(_) => "Error",
+    }
+  }
+
+  pub fn get_diffie_hellman_error(_: &DiffieHellmanError) -> &'static str {
+    "TypeError"
+  }
+
+  pub fn get_sign_ed25519_error(_: &SignEd25519Error) -> &'static str {
+    "TypeError"
+  }
+
+  pub fn get_verify_ed25519_error(_: &VerifyEd25519Error) -> &'static str {
+    "TypeError"
+  }
+}
+
+fn get_os_error(error: &OsError) -> &'static str {
+  match error {
+    OsError::Permission(e) => get_permission_check_error_class(e),
+    OsError::InvalidUtf8(_) => "InvalidData",
+    OsError::EnvEmptyKey => "TypeError",
+    OsError::EnvInvalidKey(_) => "TypeError",
+    OsError::EnvInvalidValue(_) => "TypeError",
+    OsError::Io(e) => get_io_error_class(e),
+    OsError::Var(e) => get_env_var_error_class(e),
+  }
+}
+
+fn get_sync_fetch_error(error: &SyncFetchError) -> &'static str {
+  match error {
+    SyncFetchError::BlobUrlsNotSupportedInContext => "TypeError",
+    SyncFetchError::Io(e) => get_io_error_class(e),
+    SyncFetchError::InvalidScriptUrl => "TypeError",
+    SyncFetchError::InvalidStatusCode(_) => "TypeError",
+    SyncFetchError::ClassicScriptSchemeUnsupportedInWorkers(_) => "TypeError",
+    SyncFetchError::InvalidUri(_) => "Error",
+    SyncFetchError::InvalidMimeType(_) => "DOMExceptionNetworkError",
+    SyncFetchError::MissingMimeType => "DOMExceptionNetworkError",
+    SyncFetchError::Fetch(e) => get_fetch_error(e),
+    SyncFetchError::Join(_) => "Error",
+    SyncFetchError::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+  }
+}
+
 pub fn get_error_class_name(e: &AnyError) -> Option<&'static str> {
   deno_core::error::get_custom_error_class(e)
-    .or_else(|| deno_webgpu::error::get_error_class_name(e))
-    .or_else(|| deno_web::get_error_class_name(e))
-    .or_else(|| deno_webstorage::get_not_supported_error_class_name(e))
-    .or_else(|| deno_websocket::get_network_error_class_name(e))
+    .or_else(|| {
+      e.downcast_ref::<ChildPermissionError>()
+        .map(get_child_permission_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<PermissionCheckError>()
+        .map(get_permission_check_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<PermissionError>()
+        .map(get_permission_error_class)
+    })
+    .or_else(|| e.downcast_ref::<FsError>().map(get_fs_error))
+    .or_else(|| {
+      e.downcast_ref::<node::BlocklistError>()
+        .map(node::get_blocklist_error)
+    })
+    .or_else(|| e.downcast_ref::<node::FsError>().map(node::get_fs_error))
+    .or_else(|| {
+      e.downcast_ref::<node::IdnaError>()
+        .map(node::get_idna_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::IpcJsonStreamError>()
+        .map(node::get_ipc_json_stream_error)
+    })
+    .or_else(|| e.downcast_ref::<node::IpcError>().map(node::get_ipc_error))
+    .or_else(|| {
+      e.downcast_ref::<node::WorkerThreadsFilenameError>()
+        .map(node::get_worker_threads_filename_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::RequireError>()
+        .map(node::get_require_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::Http2Error>()
+        .map(node::get_http2_error)
+    })
+    .or_else(|| e.downcast_ref::<node::OsError>().map(node::get_os_error))
+    .or_else(|| {
+      e.downcast_ref::<node::BrotliError>()
+        .map(node::get_brotli_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::ModeError>()
+        .map(node::get_mode_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::ZlibError>()
+        .map(node::get_zlib_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::CipherError>()
+        .map(node::get_crypto_cipher_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::CipherContextError>()
+        .map(node::get_crypto_cipher_context_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::DecipherError>()
+        .map(node::get_crypto_decipher_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::DecipherContextError>()
+        .map(node::get_crypto_decipher_context_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::X509Error>()
+        .map(node::get_x509_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::KeyObjectHandlePrehashedSignAndVerifyError>()
+        .map(node::get_crypto_key_object_handle_prehashed_sign_and_verify_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::HashError>()
+        .map(node::get_crypto_hash_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::AsymmetricPublicKeyJwkError>()
+        .map(node::get_asymmetric_public_key_jwk_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::GenerateRsaPssError>()
+        .map(node::get_generate_rsa_pss_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::AsymmetricPrivateKeyDerError>()
+        .map(node::get_asymmetric_private_key_der_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::AsymmetricPublicKeyDerError>()
+        .map(node::get_asymmetric_public_key_der_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::ExportPublicKeyPemError>()
+        .map(node::get_export_public_key_pem_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::ExportPrivateKeyPemError>()
+        .map(node::get_export_private_key_pem_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::RsaJwkError>()
+        .map(node::get_rsa_jwk_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::EcJwkError>()
+        .map(node::get_ec_jwk_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::EdRawError>()
+        .map(node::get_ed_raw_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::Pbkdf2Error>()
+        .map(node::get_pbkdf2_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::ScryptAsyncError>()
+        .map(node::get_scrypt_async_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::HkdfError>()
+        .map(node::get_hkdf_error_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::RsaPssParamsParseError>()
+        .map(node::get_rsa_pss_params_parse_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::AsymmetricPrivateKeyError>()
+        .map(node::get_asymmetric_private_key_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::AsymmetricPublicKeyError>()
+        .map(node::get_asymmetric_public_key_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::PrivateEncryptDecryptError>()
+        .map(node::get_private_encrypt_decrypt_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::EcdhEncodePubKey>()
+        .map(node::get_ecdh_encode_pub_key_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::DiffieHellmanError>()
+        .map(node::get_diffie_hellman_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::SignEd25519Error>()
+        .map(node::get_sign_ed25519_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::VerifyEd25519Error>()
+        .map(node::get_verify_ed25519_error)
+    })
+    .or_else(|| e.downcast_ref::<NApiError>().map(get_napi_error_class))
+    .or_else(|| e.downcast_ref::<WebError>().map(get_web_error_class))
+    .or_else(|| {
+      e.downcast_ref::<CreateWorkerError>()
+        .map(get_create_worker_error)
+    })
+    .or_else(|| e.downcast_ref::<TtyError>().map(get_tty_error))
+    .or_else(|| e.downcast_ref::<ReadlineError>().map(get_readline_error))
+    .or_else(|| e.downcast_ref::<SignalError>().map(get_signal_error))
+    .or_else(|| e.downcast_ref::<FsEventsError>().map(get_fs_events_error))
+    .or_else(|| e.downcast_ref::<HttpStartError>().map(get_http_start_error))
+    .or_else(|| e.downcast_ref::<ProcessError>().map(get_process_error))
+    .or_else(|| e.downcast_ref::<OsError>().map(get_os_error))
+    .or_else(|| e.downcast_ref::<SyncFetchError>().map(get_sync_fetch_error))
+    .or_else(|| {
+      e.downcast_ref::<CompressionError>()
+        .map(get_web_compression_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<MessagePortError>()
+        .map(get_web_message_port_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<StreamResourceError>()
+        .map(get_web_stream_resource_error_class)
+    })
+    .or_else(|| e.downcast_ref::<BlobError>().map(get_web_blob_error_class))
+    .or_else(|| e.downcast_ref::<IRError>().map(|_| "TypeError"))
+    .or_else(|| e.downcast_ref::<ReprError>().map(get_ffi_repr_error_class))
+    .or_else(|| e.downcast_ref::<HttpError>().map(get_http_error))
+    .or_else(|| e.downcast_ref::<HttpNextError>().map(get_http_next_error))
+    .or_else(|| {
+      e.downcast_ref::<WebSocketUpgradeError>()
+        .map(get_websocket_upgrade_error)
+    })
+    .or_else(|| e.downcast_ref::<FsOpsError>().map(get_fs_ops_error))
+    .or_else(|| {
+      e.downcast_ref::<DlfcnError>()
+        .map(get_ffi_dlfcn_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<StaticError>()
+        .map(get_ffi_static_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<CallbackError>()
+        .map(get_ffi_callback_error_class)
+    })
+    .or_else(|| e.downcast_ref::<CallError>().map(get_ffi_call_error_class))
+    .or_else(|| e.downcast_ref::<TlsError>().map(get_tls_error_class))
+    .or_else(|| e.downcast_ref::<CronError>().map(get_cron_error_class))
+    .or_else(|| e.downcast_ref::<CanvasError>().map(get_canvas_error))
+    .or_else(|| e.downcast_ref::<CacheError>().map(get_cache_error))
+    .or_else(|| e.downcast_ref::<WebsocketError>().map(get_websocket_error))
+    .or_else(|| {
+      e.downcast_ref::<HandshakeError>()
+        .map(get_websocket_handshake_error)
+    })
+    .or_else(|| e.downcast_ref::<KvError>().map(get_kv_error))
+    .or_else(|| e.downcast_ref::<FetchError>().map(get_fetch_error))
+    .or_else(|| {
+      e.downcast_ref::<HttpClientCreateError>()
+        .map(get_http_client_create_error)
+    })
+    .or_else(|| e.downcast_ref::<NetError>().map(get_net_error))
+    .or_else(|| {
+      e.downcast_ref::<deno_net::io::MapError>()
+        .map(get_net_map_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<BroadcastChannelError>()
+        .map(get_broadcast_channel_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_webgpu::InitError>()
+        .map(get_webgpu_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_webgpu::buffer::BufferError>()
+        .map(get_webgpu_buffer_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_webgpu::bundle::BundleError>()
+        .map(get_webgpu_bundle_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_webgpu::byow::ByowError>()
+        .map(get_webgpu_byow_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_webgpu::render_pass::RenderPassError>()
+        .map(get_webgpu_render_pass_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_webgpu::surface::SurfaceError>()
+        .map(get_webgpu_surface_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<DecryptError>()
+        .map(get_crypto_decrypt_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<EncryptError>()
+        .map(get_crypto_encrypt_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_crypto::SharedError>()
+        .map(get_crypto_shared_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_crypto::Ed25519Error>()
+        .map(get_crypto_ed25519_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<ExportKeyError>()
+        .map(get_crypto_export_key_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<GenerateKeyError>()
+        .map(get_crypto_generate_key_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<ImportKeyError>()
+        .map(get_crypto_import_key_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_crypto::X448Error>()
+        .map(get_crypto_x448_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_crypto::X25519Error>()
+        .map(get_crypto_x25519_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_crypto::Error>()
+        .map(get_crypto_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<WebStorageError>()
+        .map(get_webstorage_class_name)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_url::UrlPatternError>()
+        .map(|_| "TypeError")
+    })
     .or_else(|| {
       e.downcast_ref::<dlopen2::Error>()
         .map(get_dlopen_error_class)
diff --git a/runtime/examples/extension/main.rs b/runtime/examples/extension/main.rs
index 6f4f02508b..9889b28dcf 100644
--- a/runtime/examples/extension/main.rs
+++ b/runtime/examples/extension/main.rs
@@ -16,6 +16,7 @@ use deno_runtime::deno_permissions::PermissionsContainer;
 use deno_runtime::permissions::RuntimePermissionDescriptorParser;
 use deno_runtime::worker::MainWorker;
 use deno_runtime::worker::WorkerOptions;
+use deno_runtime::worker::WorkerServiceOptions;
 
 #[op2(fast)]
 fn op_hello(#[string] text: &str) {
@@ -35,13 +36,26 @@ async fn main() -> Result<(), AnyError> {
     Path::new(env!("CARGO_MANIFEST_DIR")).join("examples/extension/main.js");
   let main_module = ModuleSpecifier::from_file_path(js_path).unwrap();
   eprintln!("Running {main_module}...");
+  let fs = Arc::new(RealFs);
+  let permission_desc_parser =
+    Arc::new(RuntimePermissionDescriptorParser::new(fs.clone()));
   let mut worker = MainWorker::bootstrap_from_options(
     main_module.clone(),
-    PermissionsContainer::allow_all(Arc::new(
-      RuntimePermissionDescriptorParser::new(Arc::new(RealFs)),
-    )),
-    WorkerOptions {
+    WorkerServiceOptions {
       module_loader: Rc::new(FsModuleLoader),
+      permissions: PermissionsContainer::allow_all(permission_desc_parser),
+      blob_store: Default::default(),
+      broadcast_channel: Default::default(),
+      feature_checker: Default::default(),
+      node_services: Default::default(),
+      npm_process_state_provider: Default::default(),
+      root_cert_store_provider: Default::default(),
+      shared_array_buffer_store: Default::default(),
+      compiled_wasm_module_store: Default::default(),
+      v8_code_cache: Default::default(),
+      fs,
+    },
+    WorkerOptions {
       extensions: vec![hello_runtime::init_ops_and_esm()],
       ..Default::default()
     },
diff --git a/runtime/fmt_errors.rs b/runtime/fmt_errors.rs
index b2cec2a5a6..6c05fbc633 100644
--- a/runtime/fmt_errors.rs
+++ b/runtime/fmt_errors.rs
@@ -1,11 +1,10 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 //! This mod provides DenoError to unify errors across Deno.
+use color_print::cformat;
+use color_print::cstr;
 use deno_core::error::format_frame;
 use deno_core::error::JsError;
-use deno_terminal::colors::cyan;
-use deno_terminal::colors::italic_bold;
-use deno_terminal::colors::red;
-use deno_terminal::colors::yellow;
+use deno_terminal::colors;
 use std::fmt::Write as _;
 
 #[derive(Debug, Clone)]
@@ -24,26 +23,54 @@ struct IndexedErrorReference<'a> {
 enum FixSuggestionKind {
   Info,
   Hint,
+  Docs,
+}
+
+#[derive(Debug)]
+enum FixSuggestionMessage<'a> {
+  Single(&'a str),
+  Multiline(&'a [&'a str]),
 }
 
 #[derive(Debug)]
 pub struct FixSuggestion<'a> {
   kind: FixSuggestionKind,
-  message: &'a str,
+  message: FixSuggestionMessage<'a>,
 }
 
 impl<'a> FixSuggestion<'a> {
   pub fn info(message: &'a str) -> Self {
     Self {
       kind: FixSuggestionKind::Info,
-      message,
+      message: FixSuggestionMessage::Single(message),
+    }
+  }
+
+  pub fn info_multiline(messages: &'a [&'a str]) -> Self {
+    Self {
+      kind: FixSuggestionKind::Info,
+      message: FixSuggestionMessage::Multiline(messages),
     }
   }
 
   pub fn hint(message: &'a str) -> Self {
     Self {
       kind: FixSuggestionKind::Hint,
-      message,
+      message: FixSuggestionMessage::Single(message),
+    }
+  }
+
+  pub fn hint_multiline(messages: &'a [&'a str]) -> Self {
+    Self {
+      kind: FixSuggestionKind::Hint,
+      message: FixSuggestionMessage::Multiline(messages),
+    }
+  }
+
+  pub fn docs(url: &'a str) -> Self {
+    Self {
+      kind: FixSuggestionKind::Docs,
+      message: FixSuggestionMessage::Single(url),
     }
   }
 }
@@ -58,10 +85,10 @@ impl deno_core::error::ErrorFormat for AnsiColors {
     use deno_core::error::ErrorElement::*;
     match element {
       Anonymous | NativeFrame | FileName | EvalOrigin => {
-        cyan(s).to_string().into()
+        colors::cyan(s).to_string().into()
       }
-      LineNumber | ColumnNumber => yellow(s).to_string().into(),
-      FunctionName | PromiseAll => italic_bold(s).to_string().into(),
+      LineNumber | ColumnNumber => colors::yellow(s).to_string().into(),
+      FunctionName | PromiseAll => colors::italic_bold(s).to_string().into(),
     }
   }
 }
@@ -94,7 +121,7 @@ fn format_maybe_source_line(
   if column_number as usize > source_line.len() {
     return format!(
       "\n{} Couldn't format source line: Column {} is out of bounds (source may have changed at runtime)",
-      yellow("Warning"), column_number,
+      colors::yellow("Warning"), column_number,
     );
   }
 
@@ -107,9 +134,9 @@ fn format_maybe_source_line(
   }
   s.push('^');
   let color_underline = if is_error {
-    red(&s).to_string()
+    colors::red(&s).to_string()
   } else {
-    cyan(&s).to_string()
+    colors::cyan(&s).to_string()
   };
 
   let indent = format!("{:indent$}", "", indent = level);
@@ -180,7 +207,8 @@ fn format_js_error_inner(
 
   if let Some(circular) = &circular {
     if js_error.is_same_error(circular.reference.to) {
-      write!(s, " {}", cyan(format!("<ref *{}>", circular.index))).unwrap();
+      write!(s, " {}", colors::cyan(format!("<ref *{}>", circular.index)))
+        .unwrap();
     }
   }
 
@@ -218,7 +246,8 @@ fn format_js_error_inner(
       .unwrap_or(false);
 
     let error_string = if is_caused_by_circular {
-      cyan(format!("[Circular *{}]", circular.unwrap().index)).to_string()
+      colors::cyan(format!("[Circular *{}]", circular.unwrap().index))
+        .to_string()
     } else {
       format_js_error_inner(cause, circular, false, vec![])
     };
@@ -235,10 +264,35 @@ fn format_js_error_inner(
     for (index, suggestion) in suggestions.iter().enumerate() {
       write!(s, "    ").unwrap();
       match suggestion.kind {
-        FixSuggestionKind::Hint => write!(s, "{} ", cyan("hint:")).unwrap(),
-        FixSuggestionKind::Info => write!(s, "{} ", yellow("info:")).unwrap(),
+        FixSuggestionKind::Hint => {
+          write!(s, "{} ", colors::cyan("hint:")).unwrap()
+        }
+        FixSuggestionKind::Info => {
+          write!(s, "{} ", colors::yellow("info:")).unwrap()
+        }
+        FixSuggestionKind::Docs => {
+          write!(s, "{} ", colors::green("docs:")).unwrap()
+        }
       };
-      write!(s, "{}", suggestion.message).unwrap();
+      match suggestion.message {
+        FixSuggestionMessage::Single(msg) => {
+          if matches!(suggestion.kind, FixSuggestionKind::Docs) {
+            write!(s, "{}", cformat!("<u>{}</>", msg)).unwrap();
+          } else {
+            write!(s, "{}", msg).unwrap();
+          }
+        }
+        FixSuggestionMessage::Multiline(messages) => {
+          for (idx, message) in messages.iter().enumerate() {
+            if idx != 0 {
+              writeln!(s).unwrap();
+              write!(s, "          ").unwrap();
+            }
+            write!(s, "{}", message).unwrap();
+          }
+        }
+      }
+
       if index != (suggestions.len() - 1) {
         writeln!(s).unwrap();
       }
@@ -248,6 +302,166 @@ fn format_js_error_inner(
   s
 }
 
+fn get_suggestions_for_terminal_errors(e: &JsError) -> Vec<FixSuggestion> {
+  if let Some(msg) = &e.message {
+    if msg.contains("module is not defined")
+      || msg.contains("exports is not defined")
+      || msg.contains("require is not defined")
+    {
+      return vec![
+        FixSuggestion::info_multiline(&[
+          cstr!("Deno supports CommonJS modules in <u>.cjs</> files, or when the closest"),
+          cstr!("<u>package.json</> has a <i>\"type\": \"commonjs\"</> option.")
+        ]),
+        FixSuggestion::hint_multiline(&[
+          "Rewrite this module to ESM,",
+          cstr!("or change the file extension to <u>.cjs</u>,"),
+          cstr!("or add <u>package.json</> next to the file with <i>\"type\": \"commonjs\"</> option."),
+        ]),
+        FixSuggestion::docs("https://docs.deno.com/go/commonjs"),
+      ];
+    } else if msg.contains("__filename is not defined") {
+      return vec![
+        FixSuggestion::info(cstr!(
+          "<u>__filename</> global is not available in ES modules."
+        )),
+        FixSuggestion::hint(cstr!("Use <u>import.meta.filename</> instead.")),
+      ];
+    } else if msg.contains("__dirname is not defined") {
+      return vec![
+        FixSuggestion::info(cstr!(
+          "<u>__dirname</> global is not available in ES modules."
+        )),
+        FixSuggestion::hint(cstr!("Use <u>import.meta.dirname</> instead.")),
+      ];
+    } else if msg.contains("Buffer is not defined") {
+      return vec![
+        FixSuggestion::info(cstr!(
+          "<u>Buffer</> is not available in the global scope in Deno."
+        )),
+        FixSuggestion::hint_multiline(&[
+          cstr!("Import it explicitly with <u>import { Buffer } from \"node:buffer\";</>,"),
+          cstr!("or run again with <u>--unstable-node-globals</> flag to add this global."),
+        ]),
+      ];
+    } else if msg.contains("clearImmediate is not defined") {
+      return vec![
+        FixSuggestion::info(cstr!(
+          "<u>clearImmediate</> is not available in the global scope in Deno."
+        )),
+        FixSuggestion::hint_multiline(&[
+          cstr!("Import it explicitly with <u>import { clearImmediate } from \"node:timers\";</>,"),
+          cstr!("or run again with <u>--unstable-node-globals</> flag to add this global."),
+        ]),
+      ];
+    } else if msg.contains("setImmediate is not defined") {
+      return vec![
+        FixSuggestion::info(cstr!(
+          "<u>setImmediate</> is not available in the global scope in Deno."
+        )),
+        FixSuggestion::hint_multiline(
+          &[cstr!("Import it explicitly with <u>import { setImmediate } from \"node:timers\";</>,"),
+          cstr!("or run again with <u>--unstable-node-globals</> flag to add this global."),
+        ]),
+      ];
+    } else if msg.contains("global is not defined") {
+      return vec![
+        FixSuggestion::info(cstr!(
+          "<u>global</> is not available in the global scope in Deno."
+        )),
+        FixSuggestion::hint_multiline(&[
+          cstr!("Use <u>globalThis</> instead, or assign <u>globalThis.global = globalThis</>,"),
+          cstr!("or run again with <u>--unstable-node-globals</> flag to add this global."),
+        ]),
+      ];
+    } else if msg.contains("openKv is not a function") {
+      return vec![
+        FixSuggestion::info("Deno.openKv() is an unstable API."),
+        FixSuggestion::hint(
+          "Run again with `--unstable-kv` flag to enable this API.",
+        ),
+      ];
+    } else if msg.contains("cron is not a function") {
+      return vec![
+        FixSuggestion::info("Deno.cron() is an unstable API."),
+        FixSuggestion::hint(
+          "Run again with `--unstable-cron` flag to enable this API.",
+        ),
+      ];
+    } else if msg.contains("WebSocketStream is not defined") {
+      return vec![
+        FixSuggestion::info("new WebSocketStream() is an unstable API."),
+        FixSuggestion::hint(
+          "Run again with `--unstable-net` flag to enable this API.",
+        ),
+      ];
+    } else if msg.contains("Temporal is not defined") {
+      return vec![
+        FixSuggestion::info("Temporal is an unstable API."),
+        FixSuggestion::hint(
+          "Run again with `--unstable-temporal` flag to enable this API.",
+        ),
+      ];
+    } else if msg.contains("BroadcastChannel is not defined") {
+      return vec![
+        FixSuggestion::info("BroadcastChannel is an unstable API."),
+        FixSuggestion::hint(
+          "Run again with `--unstable-broadcast-channel` flag to enable this API.",
+        ),
+      ];
+    } else if msg.contains("window is not defined") {
+      return vec![
+        FixSuggestion::info("window global is not available in Deno 2."),
+        FixSuggestion::hint("Replace `window` with `globalThis`."),
+      ];
+    } else if msg.contains("UnsafeWindowSurface is not a constructor") {
+      return vec![
+        FixSuggestion::info("Deno.UnsafeWindowSurface is an unstable API."),
+        FixSuggestion::hint(
+          "Run again with `--unstable-webgpu` flag to enable this API.",
+        ),
+      ];
+    // Try to capture errors like:
+    // ```
+    // Uncaught Error: Cannot find module '../build/Release/canvas.node'
+    // Require stack:
+    // - /.../deno/npm/registry.npmjs.org/canvas/2.11.2/lib/bindings.js
+    // - /.../.cache/deno/npm/registry.npmjs.org/canvas/2.11.2/lib/canvas.js
+    // ```
+    } else if msg.contains("Cannot find module")
+      && msg.contains("Require stack")
+      && msg.contains(".node'")
+    {
+      return vec![
+        FixSuggestion::info_multiline(
+          &[
+            "Trying to execute an npm package using Node-API addons,",
+            "these packages require local `node_modules` directory to be present."
+          ]
+        ),
+        FixSuggestion::hint_multiline(
+          &[
+            "Add `\"nodeModulesDir\": \"auto\" option to `deno.json`, and then run",
+            "`deno install --allow-scripts=npm:<package> --entrypoint <script>` to setup `node_modules` directory."
+          ]
+        )
+      ];
+    } else if msg.contains("document is not defined") {
+      return vec![
+        FixSuggestion::info(cstr!(
+          "<u>document</> global is not available in Deno."
+        )),
+        FixSuggestion::hint_multiline(&[
+          cstr!("Use a library like <u>happy-dom</>, <u>deno_dom</>, <u>linkedom</> or <u>JSDom</>"),
+          cstr!("and setup the <u>document</> global according to the library documentation."),
+        ]),
+      ];
+    }
+  }
+
+  vec![]
+}
+
 /// Format a [`JsError`] for terminal output.
 pub fn format_js_error(js_error: &JsError) -> String {
   let circular =
@@ -255,21 +469,7 @@ pub fn format_js_error(js_error: &JsError) -> String {
       reference,
       index: 1,
     });
-
-  format_js_error_inner(js_error, circular, true, vec![])
-}
-
-/// Format a [`JsError`] for terminal output, printing additional suggestions.
-pub fn format_js_error_with_suggestions(
-  js_error: &JsError,
-  suggestions: Vec<FixSuggestion>,
-) -> String {
-  let circular =
-    find_recursive_cause(js_error).map(|reference| IndexedErrorReference {
-      reference,
-      index: 1,
-    });
-
+  let suggestions = get_suggestions_for_terminal_errors(js_error);
   format_js_error_inner(js_error, circular, true, suggestions)
 }
 
diff --git a/runtime/fs_util.rs b/runtime/fs_util.rs
index 15ebafdf61..a858e9770d 100644
--- a/runtime/fs_util.rs
+++ b/runtime/fs_util.rs
@@ -2,12 +2,10 @@
 
 use deno_core::anyhow::Context;
 use deno_core::error::AnyError;
+use deno_path_util::normalize_path;
 use std::path::Path;
 use std::path::PathBuf;
 
-pub use deno_core::normalize_path;
-pub use deno_permissions::specifier_to_file_path;
-
 #[inline]
 pub fn resolve_from_cwd(path: &Path) -> Result<PathBuf, AnyError> {
   if path.is_absolute() {
diff --git a/runtime/inspector_server.rs b/runtime/inspector_server.rs
index 1f8cd5e714..a789dd3dca 100644
--- a/runtime/inspector_server.rs
+++ b/runtime/inspector_server.rs
@@ -19,6 +19,8 @@ use deno_core::serde_json::Value;
 use deno_core::unsync::spawn;
 use deno_core::url::Url;
 use deno_core::InspectorMsg;
+use deno_core::InspectorSessionKind;
+use deno_core::InspectorSessionOptions;
 use deno_core::InspectorSessionProxy;
 use deno_core::JsRuntime;
 use fastwebsockets::Frame;
@@ -192,6 +194,11 @@ fn handle_ws_request(
     let inspector_session_proxy = InspectorSessionProxy {
       tx: outbound_tx,
       rx: inbound_rx,
+      options: InspectorSessionOptions {
+        kind: InspectorSessionKind::NonBlocking {
+          wait_for_disconnect: true,
+        },
+      },
     };
 
     log::info!("Debugger session started.");
diff --git a/runtime/js/10_permissions.js b/runtime/js/10_permissions.js
index ef31358687..831b6bf2ae 100644
--- a/runtime/js/10_permissions.js
+++ b/runtime/js/10_permissions.js
@@ -269,7 +269,13 @@ function serializePermissions(permissions) {
   if (typeof permissions == "object" && permissions != null) {
     const serializedPermissions = { __proto__: null };
     for (
-      const key of new SafeArrayIterator(["read", "write", "run", "ffi"])
+      const key of new SafeArrayIterator([
+        "read",
+        "write",
+        "run",
+        "ffi",
+        "import",
+      ])
     ) {
       if (ArrayIsArray(permissions[key])) {
         serializedPermissions[key] = ArrayPrototypeMap(
diff --git a/runtime/js/40_fs_events.js b/runtime/js/40_fs_events.js
index ec2474c0ad..322ee6b3ca 100644
--- a/runtime/js/40_fs_events.js
+++ b/runtime/js/40_fs_events.js
@@ -21,7 +21,7 @@ class FsWatcher {
 
   constructor(paths, options) {
     const { recursive } = options;
-    this.#rid = op_fs_events_open({ recursive, paths });
+    this.#rid = op_fs_events_open(recursive, paths);
   }
 
   unref() {
diff --git a/runtime/js/90_deno_ns.js b/runtime/js/90_deno_ns.js
index fd2ac00f20..079338510b 100644
--- a/runtime/js/90_deno_ns.js
+++ b/runtime/js/90_deno_ns.js
@@ -29,6 +29,7 @@ import * as tty from "ext:runtime/40_tty.js";
 import * as kv from "ext:deno_kv/01_db.ts";
 import * as cron from "ext:deno_cron/01_cron.ts";
 import * as webgpuSurface from "ext:deno_webgpu/02_surface.js";
+import * as telemetry from "ext:runtime/telemetry.js";
 
 const denoNs = {
   Process: process.Process,
@@ -134,7 +135,7 @@ const denoNs = {
   createHttpClient: httpClient.createHttpClient,
 };
 
-// NOTE(bartlomieju): keep IDs in sync with `cli/main.rs`
+// NOTE(bartlomieju): keep IDs in sync with `runtime/lib.rs`
 const unstableIds = {
   broadcastChannel: 1,
   cron: 2,
@@ -143,11 +144,13 @@ const unstableIds = {
   http: 5,
   kv: 6,
   net: 7,
-  process: 8,
-  temporal: 9,
-  unsafeProto: 10,
-  webgpu: 11,
-  workerOptions: 12,
+  nodeGlobals: 8,
+  otel: 9,
+  process: 10,
+  temporal: 11,
+  unsafeProto: 12,
+  webgpu: 13,
+  workerOptions: 14,
 };
 
 const denoNsUnstableById = { __proto__: null };
@@ -181,4 +184,9 @@ denoNsUnstableById[unstableIds.webgpu] = {
 
 // denoNsUnstableById[unstableIds.workerOptions] = { __proto__: null }
 
+denoNsUnstableById[unstableIds.otel] = {
+  tracing: telemetry.tracing,
+  metrics: telemetry.metrics,
+};
+
 export { denoNs, denoNsUnstableById, unstableIds };
diff --git a/runtime/js/98_global_scope_shared.js b/runtime/js/98_global_scope_shared.js
index 7a27238996..f8e76b7ce7 100644
--- a/runtime/js/98_global_scope_shared.js
+++ b/runtime/js/98_global_scope_shared.js
@@ -32,6 +32,8 @@ import { DOMException } from "ext:deno_web/01_dom_exception.js";
 import * as abortSignal from "ext:deno_web/03_abort_signal.js";
 import * as imageData from "ext:deno_web/16_image_data.js";
 import process from "node:process";
+import Buffer from "node:buffer";
+import { clearImmediate, setImmediate } from "node:timers";
 import { loadWebGPU } from "ext:deno_webgpu/00_init.js";
 import * as webgpuSurface from "ext:deno_webgpu/02_surface.js";
 import { unstableIds } from "ext:runtime/90_deno_ns.js";
@@ -300,4 +302,15 @@ unstableForWindowOrWorkerGlobalScope[unstableIds.net] = {
 
 unstableForWindowOrWorkerGlobalScope[unstableIds.webgpu] = {};
 
+unstableForWindowOrWorkerGlobalScope[unstableIds.nodeGlobals] = {
+  Buffer: core.propWritable(Buffer),
+  setImmediate: core.propWritable(setImmediate),
+  clearImmediate: core.propWritable(clearImmediate),
+  global: {
+    enumerable: true,
+    configurable: true,
+    get: () => globalThis,
+  },
+};
+
 export { unstableForWindowOrWorkerGlobalScope, windowOrWorkerGlobalScope };
diff --git a/runtime/js/99_main.js b/runtime/js/99_main.js
index 0da2072b84..2da5c5398c 100644
--- a/runtime/js/99_main.js
+++ b/runtime/js/99_main.js
@@ -27,7 +27,6 @@ const {
   ArrayPrototypeForEach,
   ArrayPrototypeIncludes,
   ArrayPrototypeMap,
-  DateNow,
   Error,
   ErrorPrototype,
   FunctionPrototypeBind,
@@ -87,6 +86,8 @@ import {
   workerRuntimeGlobalProperties,
 } from "ext:runtime/98_global_scope_worker.js";
 import { SymbolDispose, SymbolMetadata } from "ext:deno_web/00_infra.js";
+import { bootstrap as bootstrapOtel } from "ext:runtime/telemetry.js";
+
 // deno-lint-ignore prefer-primordials
 if (Symbol.metadata) {
   throw "V8 supports Symbol.metadata now, no need to shim it";
@@ -169,8 +170,11 @@ let isClosing = false;
 let globalDispatchEvent;
 
 function hasMessageEventListener() {
+  // the function name is kind of a misnomer, but we want to behave
+  // as if we have message event listeners if a node message port is explicitly
+  // refed (and the inverse as well)
   return event.listenerCount(globalThis, "message") > 0 ||
-    messagePort.messageEventListenerCount > 0;
+    messagePort.refedMessagePortsCount > 0;
 }
 
 async function pollForMessages() {
@@ -571,6 +575,7 @@ function bootstrapMainRuntime(runtimeOptions, warmup = false) {
       10: serveHost,
       11: serveIsMain,
       12: serveWorkerCount,
+      13: otelConfig,
     } = runtimeOptions;
 
     if (mode === executionModes.serve) {
@@ -639,7 +644,7 @@ function bootstrapMainRuntime(runtimeOptions, warmup = false) {
 
     removeImportedOps();
 
-    performance.setTimeOrigin(DateNow());
+    performance.setTimeOrigin();
     globalThis_ = globalThis;
 
     // Remove bootstrapping data from the global scope
@@ -671,9 +676,10 @@ function bootstrapMainRuntime(runtimeOptions, warmup = false) {
     });
     ObjectSetPrototypeOf(globalThis, Window.prototype);
 
+    bootstrapOtel(otelConfig);
+
     if (inspectFlag) {
-      const consoleFromDeno = globalThis.console;
-      core.wrapConsole(consoleFromDeno, core.v8Console);
+      core.wrapConsole(globalThis.console, core.v8Console);
     }
 
     event.defineEventHandler(globalThis, "error");
@@ -693,6 +699,7 @@ function bootstrapMainRuntime(runtimeOptions, warmup = false) {
     // are lost.
     let jupyterNs = undefined;
     ObjectDefineProperty(finalDenoNs, "jupyter", {
+      __proto__: null,
       get() {
         if (jupyterNs) {
           return jupyterNs;
@@ -852,9 +859,10 @@ function bootstrapWorkerRuntime(
       5: hasNodeModulesDir,
       6: argv0,
       7: nodeDebug,
+      13: otelConfig,
     } = runtimeOptions;
 
-    performance.setTimeOrigin(DateNow());
+    performance.setTimeOrigin();
     globalThis_ = globalThis;
 
     // Remove bootstrapping data from the global scope
@@ -879,8 +887,9 @@ function bootstrapWorkerRuntime(
     }
     ObjectSetPrototypeOf(globalThis, DedicatedWorkerGlobalScope.prototype);
 
-    const consoleFromDeno = globalThis.console;
-    core.wrapConsole(consoleFromDeno, core.v8Console);
+    bootstrapOtel(otelConfig);
+
+    core.wrapConsole(globalThis.console, core.v8Console);
 
     event.defineEventHandler(self, "message");
     event.defineEventHandler(self, "error", undefined, true);
diff --git a/runtime/js/telemetry.js b/runtime/js/telemetry.js
new file mode 100644
index 0000000000..195839fb15
--- /dev/null
+++ b/runtime/js/telemetry.js
@@ -0,0 +1,409 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+import { core, primordials } from "ext:core/mod.js";
+import {
+  op_otel_log,
+  op_otel_span_attribute,
+  op_otel_span_attribute2,
+  op_otel_span_attribute3,
+  op_otel_span_continue,
+  op_otel_span_flush,
+  op_otel_span_start,
+} from "ext:core/ops";
+import { Console } from "ext:deno_console/01_console.js";
+import { performance } from "ext:deno_web/15_performance.js";
+
+const {
+  SymbolDispose,
+  MathRandom,
+  Array,
+  ObjectEntries,
+  SafeMap,
+  ReflectApply,
+  SymbolFor,
+  Error,
+  NumberPrototypeToString,
+  StringPrototypePadStart,
+} = primordials;
+const { AsyncVariable, setAsyncContext } = core;
+
+const CURRENT = new AsyncVariable();
+let TRACING_ENABLED = false;
+let DETERMINISTIC = false;
+
+const SPAN_ID_BYTES = 8;
+const TRACE_ID_BYTES = 16;
+
+const TRACE_FLAG_SAMPLED = 1 << 0;
+
+const hexSliceLookupTable = (function () {
+  const alphabet = "0123456789abcdef";
+  const table = new Array(256);
+  for (let i = 0; i < 16; ++i) {
+    const i16 = i * 16;
+    for (let j = 0; j < 16; ++j) {
+      table[i16 + j] = alphabet[i] + alphabet[j];
+    }
+  }
+  return table;
+})();
+
+let counter = 1;
+
+const INVALID_SPAN_ID = "0000000000000000";
+const INVALID_TRACE_ID = "00000000000000000000000000000000";
+
+function generateId(bytes) {
+  if (DETERMINISTIC) {
+    return StringPrototypePadStart(
+      NumberPrototypeToString(counter++, 16),
+      bytes * 2,
+      "0",
+    );
+  }
+  let out = "";
+  for (let i = 0; i < bytes / 4; i += 1) {
+    const r32 = (MathRandom() * 2 ** 32) >>> 0;
+    out += hexSliceLookupTable[(r32 >> 24) & 0xff];
+    out += hexSliceLookupTable[(r32 >> 16) & 0xff];
+    out += hexSliceLookupTable[(r32 >> 8) & 0xff];
+    out += hexSliceLookupTable[r32 & 0xff];
+  }
+  return out;
+}
+
+function submit(span) {
+  if (!(span.traceFlags & TRACE_FLAG_SAMPLED)) return;
+
+  op_otel_span_start(
+    span.traceId,
+    span.spanId,
+    span.parentSpanId ?? "",
+    span.kind,
+    span.name,
+    span.startTime,
+    span.endTime,
+  );
+
+  if (span.status !== null && span.status.code !== 0) {
+    op_otel_span_continue(span.code, span.message ?? "");
+  }
+
+  const attributes = ObjectEntries(span.attributes);
+  let i = 0;
+  while (i < attributes.length) {
+    if (i + 2 < attributes.length) {
+      op_otel_span_attribute3(
+        attributes.length,
+        attributes[i][0],
+        attributes[i][1],
+        attributes[i + 1][0],
+        attributes[i + 1][1],
+        attributes[i + 2][0],
+        attributes[i + 2][1],
+      );
+      i += 3;
+    } else if (i + 1 < attributes.length) {
+      op_otel_span_attribute2(
+        attributes.length,
+        attributes[i][0],
+        attributes[i][1],
+        attributes[i + 1][0],
+        attributes[i + 1][1],
+      );
+      i += 2;
+    } else {
+      op_otel_span_attribute(
+        attributes.length,
+        attributes[i][0],
+        attributes[i][1],
+      );
+      i += 1;
+    }
+  }
+
+  op_otel_span_flush();
+}
+
+const now = () => (performance.timeOrigin + performance.now()) / 1000;
+
+const NO_ASYNC_CONTEXT = {};
+
+class Span {
+  traceId;
+  spanId;
+  parentSpanId;
+  kind;
+  name;
+  startTime;
+  endTime;
+  status = null;
+  attributes = { __proto__: null };
+  traceFlags = TRACE_FLAG_SAMPLED;
+
+  enabled = TRACING_ENABLED;
+  #asyncContext = NO_ASYNC_CONTEXT;
+
+  constructor(name, kind = "internal") {
+    if (!this.enabled) {
+      this.traceId = INVALID_TRACE_ID;
+      this.spanId = INVALID_SPAN_ID;
+      this.parentSpanId = INVALID_SPAN_ID;
+      return;
+    }
+
+    this.startTime = now();
+
+    this.spanId = generateId(SPAN_ID_BYTES);
+
+    let traceId;
+    let parentSpanId;
+    const parent = Span.current();
+    if (parent) {
+      if (parent.spanId !== undefined) {
+        parentSpanId = parent.spanId;
+        traceId = parent.traceId;
+      } else {
+        const context = parent.spanContext();
+        parentSpanId = context.spanId;
+        traceId = context.traceId;
+      }
+    }
+    if (
+      traceId && traceId !== INVALID_TRACE_ID && parentSpanId &&
+      parentSpanId !== INVALID_SPAN_ID
+    ) {
+      this.traceId = traceId;
+      this.parentSpanId = parentSpanId;
+    } else {
+      this.traceId = generateId(TRACE_ID_BYTES);
+      this.parentSpanId = INVALID_SPAN_ID;
+    }
+
+    this.name = name;
+
+    switch (kind) {
+      case "internal":
+        this.kind = 0;
+        break;
+      case "server":
+        this.kind = 1;
+        break;
+      case "client":
+        this.kind = 2;
+        break;
+      case "producer":
+        this.kind = 3;
+        break;
+      case "consumer":
+        this.kind = 4;
+        break;
+      default:
+        throw new Error(`Invalid span kind: ${kind}`);
+    }
+
+    this.enter();
+  }
+
+  // helper function to match otel js api
+  spanContext() {
+    return {
+      traceId: this.traceId,
+      spanId: this.spanId,
+      traceFlags: this.traceFlags,
+    };
+  }
+
+  setAttribute(name, value) {
+    if (!this.enabled) return;
+    this.attributes[name] = value;
+  }
+
+  enter() {
+    if (!this.enabled) return;
+    const context = (CURRENT.get() || ROOT_CONTEXT).setValue(SPAN_KEY, this);
+    this.#asyncContext = CURRENT.enter(context);
+  }
+
+  exit() {
+    if (!this.enabled || this.#asyncContext === NO_ASYNC_CONTEXT) return;
+    setAsyncContext(this.#asyncContext);
+    this.#asyncContext = NO_ASYNC_CONTEXT;
+  }
+
+  end() {
+    if (!this.enabled || this.endTime !== undefined) return;
+    this.exit();
+    this.endTime = now();
+    submit(this);
+  }
+
+  [SymbolDispose]() {
+    this.end();
+  }
+
+  static current() {
+    return CURRENT.get()?.getValue(SPAN_KEY);
+  }
+}
+
+function hrToSecs(hr) {
+  return ((hr[0] * 1e3 + hr[1] / 1e6) / 1000);
+}
+
+// Exporter compatible with opentelemetry js library
+class SpanExporter {
+  export(spans, resultCallback) {
+    try {
+      for (let i = 0; i < spans.length; i += 1) {
+        const span = spans[i];
+        const context = span.spanContext();
+        submit({
+          spanId: context.spanId,
+          traceId: context.traceId,
+          traceFlags: context.traceFlags,
+          name: span.name,
+          kind: span.kind,
+          parentSpanId: span.parentSpanId,
+          startTime: hrToSecs(span.startTime),
+          endTime: hrToSecs(span.endTime),
+          status: span.status,
+          attributes: span.attributes,
+        });
+      }
+      resultCallback({ code: 0 });
+    } catch (error) {
+      resultCallback({ code: 1, error });
+    }
+  }
+
+  async shutdown() {}
+
+  async forceFlush() {}
+}
+
+// SPAN_KEY matches symbol in otel-js library
+const SPAN_KEY = SymbolFor("OpenTelemetry Context Key SPAN");
+
+// Context tracker compatible with otel-js api
+class Context {
+  #data = new SafeMap();
+
+  constructor(data) {
+    this.#data = data ? new SafeMap(data) : new SafeMap();
+  }
+
+  getValue(key) {
+    return this.#data.get(key);
+  }
+
+  setValue(key, value) {
+    const c = new Context(this.#data);
+    c.#data.set(key, value);
+    return c;
+  }
+
+  deleteValue(key) {
+    const c = new Context(this.#data);
+    c.#data.delete(key);
+    return c;
+  }
+}
+
+const ROOT_CONTEXT = new Context();
+
+// Context manager for opentelemetry js library
+class ContextManager {
+  active() {
+    return CURRENT.get() ?? ROOT_CONTEXT;
+  }
+
+  with(context, fn, thisArg, ...args) {
+    const ctx = CURRENT.enter(context);
+    try {
+      return ReflectApply(fn, thisArg, args);
+    } finally {
+      setAsyncContext(ctx);
+    }
+  }
+
+  bind(context, f) {
+    return (...args) => {
+      const ctx = CURRENT.enter(context);
+      try {
+        return ReflectApply(f, thisArg, args);
+      } finally {
+        setAsyncContext(ctx);
+      }
+    };
+  }
+
+  enable() {
+    return this;
+  }
+
+  disable() {
+    return this;
+  }
+}
+
+function otelLog(message, level) {
+  let traceId = "";
+  let spanId = "";
+  let traceFlags = 0;
+  const span = Span.current();
+  if (span) {
+    if (span.spanId !== undefined) {
+      spanId = span.spanId;
+      traceId = span.traceId;
+      traceFlags = span.traceFlags;
+    } else {
+      const context = span.spanContext();
+      spanId = context.spanId;
+      traceId = context.traceId;
+      traceFlags = context.traceFlags;
+    }
+  }
+  return op_otel_log(message, level, traceId, spanId, traceFlags);
+}
+
+const otelConsoleConfig = {
+  ignore: 0,
+  capture: 1,
+  replace: 2,
+};
+
+export function bootstrap(config) {
+  if (config.length === 0) return;
+  const { 0: consoleConfig, 1: deterministic } = config;
+
+  TRACING_ENABLED = true;
+  DETERMINISTIC = deterministic === 1;
+
+  switch (consoleConfig) {
+    case otelConsoleConfig.capture:
+      core.wrapConsole(globalThis.console, new Console(otelLog));
+      break;
+    case otelConsoleConfig.replace:
+      ObjectDefineProperty(
+        globalThis,
+        "console",
+        core.propNonEnumerable(new Console(otelLog)),
+      );
+      break;
+    default:
+      break;
+  }
+}
+
+export const tracing = {
+  get enabled() {
+    return TRACING_ENABLED;
+  },
+  Span,
+  SpanExporter,
+  ContextManager,
+};
+
+// TODO(devsnek): implement metrics
+export const metrics = {};
diff --git a/runtime/lib.rs b/runtime/lib.rs
index f0b1129ce3..a6e60ced18 100644
--- a/runtime/lib.rs
+++ b/runtime/lib.rs
@@ -35,6 +35,7 @@ pub mod js;
 pub mod ops;
 pub mod permissions;
 pub mod snapshot;
+pub mod sys_info;
 pub mod tokio_util;
 pub mod web_worker;
 pub mod worker;
@@ -99,18 +100,30 @@ pub static UNSTABLE_GRANULAR_FLAGS: &[UnstableGranularFlag] = &[
     show_in_help: true,
     id: 7,
   },
+  UnstableGranularFlag {
+    name: "node-globals",
+    help_text: "Expose Node globals everywhere",
+    show_in_help: true,
+    id: 8,
+  },
+  UnstableGranularFlag {
+    name: "otel",
+    help_text: "Enable unstable OpenTelemetry features",
+    show_in_help: false,
+    id: 9,
+  },
   // TODO(bartlomieju): consider removing it
   UnstableGranularFlag {
     name: ops::process::UNSTABLE_FEATURE_NAME,
     help_text: "Enable unstable process APIs",
     show_in_help: false,
-    id: 8,
+    id: 10,
   },
   UnstableGranularFlag {
     name: "temporal",
     help_text: "Enable unstable Temporal API",
     show_in_help: true,
-    id: 9,
+    id: 11,
   },
   UnstableGranularFlag {
     name: "unsafe-proto",
@@ -118,22 +131,28 @@ pub static UNSTABLE_GRANULAR_FLAGS: &[UnstableGranularFlag] = &[
     show_in_help: true,
     // This number is used directly in the JS code. Search
     // for "unstableIds" to see where it's used.
-    id: 10,
+    id: 12,
   },
   UnstableGranularFlag {
     name: deno_webgpu::UNSTABLE_FEATURE_NAME,
     help_text: "Enable unstable `WebGPU` APIs",
     show_in_help: true,
-    id: 11,
+    id: 13,
   },
   UnstableGranularFlag {
     name: ops::worker_host::UNSTABLE_FEATURE_NAME,
     help_text: "Enable unstable Web Worker APIs",
     show_in_help: true,
-    id: 12,
+    id: 14,
   },
 ];
 
+pub fn exit(code: i32) -> ! {
+  crate::ops::otel::flush();
+  #[allow(clippy::disallowed_methods)]
+  std::process::exit(code);
+}
+
 #[cfg(test)]
 mod test {
   use super::*;
diff --git a/runtime/ops/fs_events.rs b/runtime/ops/fs_events.rs
index d88a32d917..c8e0228bc0 100644
--- a/runtime/ops/fs_events.rs
+++ b/runtime/ops/fs_events.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::parking_lot::Mutex;
 use deno_core::AsyncRefCell;
 use deno_core::CancelFuture;
@@ -20,13 +19,14 @@ use notify::EventKind;
 use notify::RecommendedWatcher;
 use notify::RecursiveMode;
 use notify::Watcher;
-use serde::Deserialize;
 use serde::Serialize;
 use std::borrow::Cow;
 use std::cell::RefCell;
 use std::convert::From;
+use std::path::Path;
 use std::path::PathBuf;
 use std::rc::Rc;
+use std::sync::Arc;
 use tokio::sync::mpsc;
 
 deno_core::extension!(
@@ -35,9 +35,7 @@ deno_core::extension!(
 );
 
 struct FsEventsResource {
-  #[allow(unused)]
-  watcher: RecommendedWatcher,
-  receiver: AsyncRefCell<mpsc::Receiver<Result<FsEvent, AnyError>>>,
+  receiver: AsyncRefCell<mpsc::Receiver<Result<FsEvent, NotifyError>>>,
   cancel: CancelHandle,
 }
 
@@ -59,7 +57,7 @@ impl Resource for FsEventsResource {
 ///
 /// Feel free to expand this struct as long as you can add tests to demonstrate
 /// the complexity.
-#[derive(Serialize, Debug)]
+#[derive(Serialize, Debug, Clone)]
 struct FsEvent {
   kind: &'static str,
   paths: Vec<PathBuf>,
@@ -93,43 +91,102 @@ impl From<NotifyEvent> for FsEvent {
   }
 }
 
-#[derive(Deserialize)]
-pub struct OpenArgs {
-  recursive: bool,
+type WatchSender = (Vec<String>, mpsc::Sender<Result<FsEvent, NotifyError>>);
+
+struct WatcherState {
+  senders: Arc<Mutex<Vec<WatchSender>>>,
+  watcher: RecommendedWatcher,
+}
+
+fn starts_with_canonicalized(path: &Path, prefix: &str) -> bool {
+  #[allow(clippy::disallowed_methods)]
+  let path = path.canonicalize().ok();
+  #[allow(clippy::disallowed_methods)]
+  let prefix = std::fs::canonicalize(prefix).ok();
+  match (path, prefix) {
+    (Some(path), Some(prefix)) => path.starts_with(prefix),
+    _ => false,
+  }
+}
+
+#[derive(Debug, thiserror::Error)]
+pub enum FsEventsError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  Permission(#[from] deno_permissions::PermissionCheckError),
+  #[error(transparent)]
+  Notify(#[from] NotifyError),
+  #[error(transparent)]
+  Canceled(#[from] deno_core::Canceled),
+}
+
+fn start_watcher(
+  state: &mut OpState,
   paths: Vec<String>,
+  sender: mpsc::Sender<Result<FsEvent, NotifyError>>,
+) -> Result<(), FsEventsError> {
+  if let Some(watcher) = state.try_borrow_mut::<WatcherState>() {
+    watcher.senders.lock().push((paths, sender));
+    return Ok(());
+  }
+
+  let senders = Arc::new(Mutex::new(vec![(paths, sender)]));
+
+  let sender_clone = senders.clone();
+  let watcher: RecommendedWatcher = Watcher::new(
+    move |res: Result<NotifyEvent, NotifyError>| {
+      let res2 = res.map(FsEvent::from).map_err(FsEventsError::Notify);
+      for (paths, sender) in sender_clone.lock().iter() {
+        // Ignore result, if send failed it means that watcher was already closed,
+        // but not all messages have been flushed.
+
+        // Only send the event if the path matches one of the paths that the user is watching
+        if let Ok(event) = &res2 {
+          if paths.iter().any(|path| {
+            event.paths.iter().any(|event_path| {
+              same_file::is_same_file(event_path, path).unwrap_or(false)
+                || starts_with_canonicalized(event_path, path)
+            })
+          }) {
+            let _ = sender.try_send(Ok(event.clone()));
+          }
+        }
+      }
+    },
+    Default::default(),
+  )?;
+
+  state.put::<WatcherState>(WatcherState { watcher, senders });
+
+  Ok(())
 }
 
 #[op2]
 #[smi]
 fn op_fs_events_open(
   state: &mut OpState,
-  #[serde] args: OpenArgs,
-) -> Result<ResourceId, AnyError> {
-  let (sender, receiver) = mpsc::channel::<Result<FsEvent, AnyError>>(16);
-  let sender = Mutex::new(sender);
-  let mut watcher: RecommendedWatcher = Watcher::new(
-    move |res: Result<NotifyEvent, NotifyError>| {
-      let res2 = res.map(FsEvent::from).map_err(AnyError::from);
-      let sender = sender.lock();
-      // Ignore result, if send failed it means that watcher was already closed,
-      // but not all messages have been flushed.
-      let _ = sender.try_send(res2);
-    },
-    Default::default(),
-  )?;
-  let recursive_mode = if args.recursive {
+  recursive: bool,
+  #[serde] paths: Vec<String>,
+) -> Result<ResourceId, FsEventsError> {
+  let (sender, receiver) = mpsc::channel::<Result<FsEvent, NotifyError>>(16);
+
+  start_watcher(state, paths.clone(), sender)?;
+
+  let recursive_mode = if recursive {
     RecursiveMode::Recursive
   } else {
     RecursiveMode::NonRecursive
   };
-  for path in &args.paths {
+  for path in &paths {
     let path = state
       .borrow_mut::<PermissionsContainer>()
       .check_read(path, "Deno.watchFs()")?;
-    watcher.watch(&path, recursive_mode)?;
+
+    let watcher = state.borrow_mut::<WatcherState>();
+    watcher.watcher.watch(&path, recursive_mode)?;
   }
   let resource = FsEventsResource {
-    watcher,
     receiver: AsyncRefCell::new(receiver),
     cancel: Default::default(),
   };
@@ -142,14 +199,18 @@ fn op_fs_events_open(
 async fn op_fs_events_poll(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<Option<FsEvent>, AnyError> {
-  let resource = state.borrow().resource_table.get::<FsEventsResource>(rid)?;
+) -> Result<Option<FsEvent>, FsEventsError> {
+  let resource = state
+    .borrow()
+    .resource_table
+    .get::<FsEventsResource>(rid)
+    .map_err(FsEventsError::Resource)?;
   let mut receiver = RcRef::map(&resource, |r| &r.receiver).borrow_mut().await;
   let cancel = RcRef::map(resource, |r| &r.cancel);
   let maybe_result = receiver.recv().or_cancel(cancel).await?;
   match maybe_result {
     Some(Ok(value)) => Ok(Some(value)),
-    Some(Err(err)) => Err(err),
+    Some(Err(err)) => Err(FsEventsError::Notify(err)),
     None => Ok(None),
   }
 }
diff --git a/runtime/ops/http.rs b/runtime/ops/http.rs
index cec8b0ef8f..6e31576686 100644
--- a/runtime/ops/http.rs
+++ b/runtime/ops/http.rs
@@ -2,9 +2,6 @@
 
 use std::rc::Rc;
 
-use deno_core::error::bad_resource_id;
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::ResourceId;
@@ -16,12 +13,31 @@ pub const UNSTABLE_FEATURE_NAME: &str = "http";
 
 deno_core::extension!(deno_http_runtime, ops = [op_http_start],);
 
+#[derive(Debug, thiserror::Error)]
+pub enum HttpStartError {
+  #[error("TCP stream is currently in use")]
+  TcpStreamInUse,
+  #[error("TLS stream is currently in use")]
+  TlsStreamInUse,
+  #[error("Unix socket is currently in use")]
+  UnixSocketInUse,
+  #[error(transparent)]
+  ReuniteTcp(#[from] tokio::net::tcp::ReuniteError),
+  #[cfg(unix)]
+  #[error(transparent)]
+  ReuniteUnix(#[from] tokio::net::unix::ReuniteError),
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
 #[op2(fast)]
 #[smi]
 fn op_http_start(
   state: &mut OpState,
   #[smi] tcp_stream_rid: ResourceId,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, HttpStartError> {
   if let Ok(resource_rc) = state
     .resource_table
     .take::<TcpStreamResource>(tcp_stream_rid)
@@ -30,11 +46,11 @@ fn op_http_start(
     // process of starting a HTTP server on top of this TCP connection, so we just return a Busy error.
     // See also: https://github.com/denoland/deno/pull/16242
     let resource = Rc::try_unwrap(resource_rc)
-      .map_err(|_| custom_error("Busy", "TCP stream is currently in use"))?;
+      .map_err(|_| HttpStartError::TcpStreamInUse)?;
     let (read_half, write_half) = resource.into_inner();
     let tcp_stream = read_half.reunite(write_half)?;
     let addr = tcp_stream.local_addr()?;
-    return http_create_conn_resource(state, tcp_stream, addr, "http");
+    return Ok(http_create_conn_resource(state, tcp_stream, addr, "http"));
   }
 
   if let Ok(resource_rc) = state
@@ -45,11 +61,11 @@ fn op_http_start(
     // process of starting a HTTP server on top of this TLS connection, so we just return a Busy error.
     // See also: https://github.com/denoland/deno/pull/16242
     let resource = Rc::try_unwrap(resource_rc)
-      .map_err(|_| custom_error("Busy", "TLS stream is currently in use"))?;
+      .map_err(|_| HttpStartError::TlsStreamInUse)?;
     let (read_half, write_half) = resource.into_inner();
     let tls_stream = read_half.unsplit(write_half);
     let addr = tls_stream.local_addr()?;
-    return http_create_conn_resource(state, tls_stream, addr, "https");
+    return Ok(http_create_conn_resource(state, tls_stream, addr, "https"));
   }
 
   #[cfg(unix)]
@@ -61,12 +77,17 @@ fn op_http_start(
     // process of starting a HTTP server on top of this UNIX socket, so we just return a Busy error.
     // See also: https://github.com/denoland/deno/pull/16242
     let resource = Rc::try_unwrap(resource_rc)
-      .map_err(|_| custom_error("Busy", "Unix socket is currently in use"))?;
+      .map_err(|_| HttpStartError::UnixSocketInUse)?;
     let (read_half, write_half) = resource.into_inner();
     let unix_stream = read_half.reunite(write_half)?;
     let addr = unix_stream.local_addr()?;
-    return http_create_conn_resource(state, unix_stream, addr, "http+unix");
+    return Ok(http_create_conn_resource(
+      state,
+      unix_stream,
+      addr,
+      "http+unix",
+    ));
   }
 
-  Err(bad_resource_id())
+  Err(HttpStartError::Other(deno_core::error::bad_resource_id()))
 }
diff --git a/runtime/ops/mod.rs b/runtime/ops/mod.rs
index feed5052bb..c2e402f33c 100644
--- a/runtime/ops/mod.rs
+++ b/runtime/ops/mod.rs
@@ -4,12 +4,12 @@ pub mod bootstrap;
 pub mod fs_events;
 pub mod http;
 pub mod os;
+pub mod otel;
 pub mod permissions;
 pub mod process;
 pub mod runtime;
 pub mod signal;
 pub mod tty;
-mod utils;
 pub mod web_worker;
 pub mod worker_host;
 
diff --git a/runtime/ops/os/mod.rs b/runtime/ops/os/mod.rs
index 544031dd7b..74c708c532 100644
--- a/runtime/ops/os/mod.rs
+++ b/runtime/ops/os/mod.rs
@@ -1,21 +1,17 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use super::utils::into_string;
+use crate::sys_info;
 use crate::worker::ExitCode;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
-use deno_core::normalize_path;
 use deno_core::op2;
 use deno_core::v8;
 use deno_core::OpState;
 use deno_node::NODE_ENV_VAR_ALLOWLIST;
+use deno_path_util::normalize_path;
 use deno_permissions::PermissionsContainer;
 use serde::Serialize;
 use std::collections::HashMap;
 use std::env;
 
-mod sys_info;
-
 deno_core::extension!(
   deno_os,
   ops = [
@@ -73,9 +69,27 @@ deno_core::extension!(
   },
 );
 
+#[derive(Debug, thiserror::Error)]
+pub enum OsError {
+  #[error(transparent)]
+  Permission(#[from] deno_permissions::PermissionCheckError),
+  #[error("File name or path {0:?} is not valid UTF-8")]
+  InvalidUtf8(std::ffi::OsString),
+  #[error("Key is an empty string.")]
+  EnvEmptyKey,
+  #[error("Key contains invalid characters: {0:?}")]
+  EnvInvalidKey(String),
+  #[error("Value contains invalid characters: {0:?}")]
+  EnvInvalidValue(String),
+  #[error(transparent)]
+  Var(#[from] env::VarError),
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+}
+
 #[op2]
 #[string]
-fn op_exec_path(state: &mut OpState) -> Result<String, AnyError> {
+fn op_exec_path(state: &mut OpState) -> Result<String, OsError> {
   let current_exe = env::current_exe().unwrap();
   state
     .borrow_mut::<PermissionsContainer>()
@@ -83,7 +97,10 @@ fn op_exec_path(state: &mut OpState) -> Result<String, AnyError> {
   // normalize path so it doesn't include '.' or '..' components
   let path = normalize_path(current_exe);
 
-  into_string(path.into_os_string())
+  path
+    .into_os_string()
+    .into_string()
+    .map_err(OsError::InvalidUtf8)
 }
 
 #[op2(fast)]
@@ -91,20 +108,16 @@ fn op_set_env(
   state: &mut OpState,
   #[string] key: &str,
   #[string] value: &str,
-) -> Result<(), AnyError> {
+) -> Result<(), OsError> {
   state.borrow_mut::<PermissionsContainer>().check_env(key)?;
   if key.is_empty() {
-    return Err(type_error("Key is an empty string."));
+    return Err(OsError::EnvEmptyKey);
   }
   if key.contains(&['=', '\0'] as &[char]) {
-    return Err(type_error(format!(
-      "Key contains invalid characters: {key:?}"
-    )));
+    return Err(OsError::EnvInvalidKey(key.to_string()));
   }
   if value.contains('\0') {
-    return Err(type_error(format!(
-      "Value contains invalid characters: {value:?}"
-    )));
+    return Err(OsError::EnvInvalidValue(value.to_string()));
   }
   env::set_var(key, value);
   Ok(())
@@ -112,7 +125,9 @@ fn op_set_env(
 
 #[op2]
 #[serde]
-fn op_env(state: &mut OpState) -> Result<HashMap<String, String>, AnyError> {
+fn op_env(
+  state: &mut OpState,
+) -> Result<HashMap<String, String>, deno_core::error::AnyError> {
   state.borrow_mut::<PermissionsContainer>().check_env_all()?;
   Ok(env::vars().collect())
 }
@@ -122,7 +137,7 @@ fn op_env(state: &mut OpState) -> Result<HashMap<String, String>, AnyError> {
 fn op_get_env(
   state: &mut OpState,
   #[string] key: String,
-) -> Result<Option<String>, AnyError> {
+) -> Result<Option<String>, OsError> {
   let skip_permission_check = NODE_ENV_VAR_ALLOWLIST.contains(&key);
 
   if !skip_permission_check {
@@ -130,13 +145,11 @@ fn op_get_env(
   }
 
   if key.is_empty() {
-    return Err(type_error("Key is an empty string."));
+    return Err(OsError::EnvEmptyKey);
   }
 
   if key.contains(&['=', '\0'] as &[char]) {
-    return Err(type_error(format!(
-      "Key contains invalid characters: {key:?}"
-    )));
+    return Err(OsError::EnvInvalidKey(key.to_string()));
   }
 
   let r = match env::var(key) {
@@ -150,10 +163,10 @@ fn op_get_env(
 fn op_delete_env(
   state: &mut OpState,
   #[string] key: String,
-) -> Result<(), AnyError> {
+) -> Result<(), OsError> {
   state.borrow_mut::<PermissionsContainer>().check_env(&key)?;
   if key.is_empty() || key.contains(&['=', '\0'] as &[char]) {
-    return Err(type_error("Key contains invalid characters."));
+    return Err(OsError::EnvInvalidKey(key.to_string()));
   }
   env::remove_var(key);
   Ok(())
@@ -173,12 +186,14 @@ fn op_get_exit_code(state: &mut OpState) -> i32 {
 #[op2(fast)]
 fn op_exit(state: &mut OpState) {
   let code = state.borrow::<ExitCode>().get();
-  std::process::exit(code)
+  crate::exit(code)
 }
 
 #[op2]
 #[serde]
-fn op_loadavg(state: &mut OpState) -> Result<(f64, f64, f64), AnyError> {
+fn op_loadavg(
+  state: &mut OpState,
+) -> Result<(f64, f64, f64), deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("loadavg", "Deno.loadavg()")?;
@@ -187,7 +202,9 @@ fn op_loadavg(state: &mut OpState) -> Result<(f64, f64, f64), AnyError> {
 
 #[op2]
 #[string]
-fn op_hostname(state: &mut OpState) -> Result<String, AnyError> {
+fn op_hostname(
+  state: &mut OpState,
+) -> Result<String, deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("hostname", "Deno.hostname()")?;
@@ -196,7 +213,9 @@ fn op_hostname(state: &mut OpState) -> Result<String, AnyError> {
 
 #[op2]
 #[string]
-fn op_os_release(state: &mut OpState) -> Result<String, AnyError> {
+fn op_os_release(
+  state: &mut OpState,
+) -> Result<String, deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("osRelease", "Deno.osRelease()")?;
@@ -207,7 +226,7 @@ fn op_os_release(state: &mut OpState) -> Result<String, AnyError> {
 #[serde]
 fn op_network_interfaces(
   state: &mut OpState,
-) -> Result<Vec<NetworkInterface>, AnyError> {
+) -> Result<Vec<NetworkInterface>, OsError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("networkInterfaces", "Deno.networkInterfaces()")?;
@@ -259,7 +278,7 @@ impl From<netif::Interface> for NetworkInterface {
 #[serde]
 fn op_system_memory_info(
   state: &mut OpState,
-) -> Result<Option<sys_info::MemInfo>, AnyError> {
+) -> Result<Option<sys_info::MemInfo>, deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("systemMemoryInfo", "Deno.systemMemoryInfo()")?;
@@ -269,7 +288,9 @@ fn op_system_memory_info(
 #[cfg(not(windows))]
 #[op2]
 #[smi]
-fn op_gid(state: &mut OpState) -> Result<Option<u32>, AnyError> {
+fn op_gid(
+  state: &mut OpState,
+) -> Result<Option<u32>, deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("gid", "Deno.gid()")?;
@@ -283,7 +304,9 @@ fn op_gid(state: &mut OpState) -> Result<Option<u32>, AnyError> {
 #[cfg(windows)]
 #[op2]
 #[smi]
-fn op_gid(state: &mut OpState) -> Result<Option<u32>, AnyError> {
+fn op_gid(
+  state: &mut OpState,
+) -> Result<Option<u32>, deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("gid", "Deno.gid()")?;
@@ -293,7 +316,9 @@ fn op_gid(state: &mut OpState) -> Result<Option<u32>, AnyError> {
 #[cfg(not(windows))]
 #[op2]
 #[smi]
-fn op_uid(state: &mut OpState) -> Result<Option<u32>, AnyError> {
+fn op_uid(
+  state: &mut OpState,
+) -> Result<Option<u32>, deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("uid", "Deno.uid()")?;
@@ -307,7 +332,9 @@ fn op_uid(state: &mut OpState) -> Result<Option<u32>, AnyError> {
 #[cfg(windows)]
 #[op2]
 #[smi]
-fn op_uid(state: &mut OpState) -> Result<Option<u32>, AnyError> {
+fn op_uid(
+  state: &mut OpState,
+) -> Result<Option<u32>, deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("uid", "Deno.uid()")?;
@@ -485,7 +512,7 @@ fn rss() -> usize {
   }
 }
 
-fn os_uptime(state: &mut OpState) -> Result<u64, AnyError> {
+fn os_uptime(state: &mut OpState) -> Result<u64, deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("osUptime", "Deno.osUptime()")?;
@@ -494,6 +521,8 @@ fn os_uptime(state: &mut OpState) -> Result<u64, AnyError> {
 
 #[op2(fast)]
 #[number]
-fn op_os_uptime(state: &mut OpState) -> Result<u64, AnyError> {
+fn op_os_uptime(
+  state: &mut OpState,
+) -> Result<u64, deno_core::error::AnyError> {
   os_uptime(state)
 }
diff --git a/runtime/ops/otel.rs b/runtime/ops/otel.rs
new file mode 100644
index 0000000000..b32764d7f8
--- /dev/null
+++ b/runtime/ops/otel.rs
@@ -0,0 +1,744 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+use crate::tokio_util::create_basic_runtime;
+use deno_core::anyhow::anyhow;
+use deno_core::anyhow::{self};
+use deno_core::futures::channel::mpsc;
+use deno_core::futures::channel::mpsc::UnboundedSender;
+use deno_core::futures::future::BoxFuture;
+use deno_core::futures::stream;
+use deno_core::futures::Stream;
+use deno_core::futures::StreamExt;
+use deno_core::op2;
+use deno_core::v8;
+use deno_core::OpState;
+use once_cell::sync::Lazy;
+use once_cell::sync::OnceCell;
+use opentelemetry::logs::AnyValue;
+use opentelemetry::logs::LogRecord as LogRecordTrait;
+use opentelemetry::logs::Severity;
+use opentelemetry::trace::SpanContext;
+use opentelemetry::trace::SpanId;
+use opentelemetry::trace::SpanKind;
+use opentelemetry::trace::Status as SpanStatus;
+use opentelemetry::trace::TraceFlags;
+use opentelemetry::trace::TraceId;
+use opentelemetry::InstrumentationScope;
+use opentelemetry::Key;
+use opentelemetry::KeyValue;
+use opentelemetry::StringValue;
+use opentelemetry::Value;
+use opentelemetry_otlp::HttpExporterBuilder;
+use opentelemetry_otlp::Protocol;
+use opentelemetry_otlp::WithExportConfig;
+use opentelemetry_otlp::WithHttpConfig;
+use opentelemetry_sdk::export::trace::SpanData;
+use opentelemetry_sdk::logs::BatchLogProcessor;
+use opentelemetry_sdk::logs::LogProcessor as LogProcessorTrait;
+use opentelemetry_sdk::logs::LogRecord;
+use opentelemetry_sdk::trace::BatchSpanProcessor;
+use opentelemetry_sdk::trace::SpanProcessor as SpanProcessorTrait;
+use opentelemetry_sdk::Resource;
+use opentelemetry_semantic_conventions::resource::PROCESS_RUNTIME_NAME;
+use opentelemetry_semantic_conventions::resource::PROCESS_RUNTIME_VERSION;
+use opentelemetry_semantic_conventions::resource::TELEMETRY_SDK_LANGUAGE;
+use opentelemetry_semantic_conventions::resource::TELEMETRY_SDK_NAME;
+use opentelemetry_semantic_conventions::resource::TELEMETRY_SDK_VERSION;
+use serde::Deserialize;
+use serde::Serialize;
+use std::borrow::Cow;
+use std::env;
+use std::fmt::Debug;
+use std::pin::Pin;
+use std::task::Context;
+use std::task::Poll;
+use std::thread;
+use std::time::Duration;
+use std::time::SystemTime;
+
+type SpanProcessor = BatchSpanProcessor<OtelSharedRuntime>;
+type LogProcessor = BatchLogProcessor<OtelSharedRuntime>;
+
+deno_core::extension!(
+  deno_otel,
+  ops = [
+    op_otel_log,
+    op_otel_span_start,
+    op_otel_span_continue,
+    op_otel_span_attribute,
+    op_otel_span_attribute2,
+    op_otel_span_attribute3,
+    op_otel_span_flush,
+  ],
+);
+
+#[derive(Debug, Clone, Serialize, Deserialize)]
+pub struct OtelConfig {
+  pub runtime_name: Cow<'static, str>,
+  pub runtime_version: Cow<'static, str>,
+  pub console: OtelConsoleConfig,
+  pub deterministic: bool,
+}
+
+#[derive(Debug, Clone, Copy, Serialize, Deserialize)]
+#[repr(u8)]
+pub enum OtelConsoleConfig {
+  Ignore = 0,
+  Capture = 1,
+  Replace = 2,
+}
+
+impl Default for OtelConfig {
+  fn default() -> Self {
+    Self {
+      runtime_name: Cow::Borrowed(env!("CARGO_PKG_NAME")),
+      runtime_version: Cow::Borrowed(env!("CARGO_PKG_VERSION")),
+      console: OtelConsoleConfig::Capture,
+      deterministic: false,
+    }
+  }
+}
+
+static OTEL_SHARED_RUNTIME_SPAWN_TASK_TX: Lazy<
+  UnboundedSender<BoxFuture<'static, ()>>,
+> = Lazy::new(otel_create_shared_runtime);
+
+fn otel_create_shared_runtime() -> UnboundedSender<BoxFuture<'static, ()>> {
+  let (spawn_task_tx, mut spawn_task_rx) =
+    mpsc::unbounded::<BoxFuture<'static, ()>>();
+
+  thread::spawn(move || {
+    let rt = create_basic_runtime();
+    rt.block_on(async move {
+      while let Some(task) = spawn_task_rx.next().await {
+        tokio::spawn(task);
+      }
+    });
+  });
+
+  spawn_task_tx
+}
+
+#[derive(Clone, Copy)]
+struct OtelSharedRuntime;
+
+impl hyper::rt::Executor<BoxFuture<'static, ()>> for OtelSharedRuntime {
+  fn execute(&self, fut: BoxFuture<'static, ()>) {
+    (*OTEL_SHARED_RUNTIME_SPAWN_TASK_TX)
+      .unbounded_send(fut)
+      .expect("failed to send task to shared OpenTelemetry runtime");
+  }
+}
+
+impl opentelemetry_sdk::runtime::Runtime for OtelSharedRuntime {
+  type Interval = Pin<Box<dyn Stream<Item = ()> + Send + 'static>>;
+  type Delay = Pin<Box<tokio::time::Sleep>>;
+
+  fn interval(&self, period: Duration) -> Self::Interval {
+    stream::repeat(())
+      .then(move |_| tokio::time::sleep(period))
+      .boxed()
+  }
+
+  fn spawn(&self, future: BoxFuture<'static, ()>) {
+    (*OTEL_SHARED_RUNTIME_SPAWN_TASK_TX)
+      .unbounded_send(future)
+      .expect("failed to send task to shared OpenTelemetry runtime");
+  }
+
+  fn delay(&self, duration: Duration) -> Self::Delay {
+    Box::pin(tokio::time::sleep(duration))
+  }
+}
+
+impl opentelemetry_sdk::runtime::RuntimeChannel for OtelSharedRuntime {
+  type Receiver<T: Debug + Send> = BatchMessageChannelReceiver<T>;
+  type Sender<T: Debug + Send> = BatchMessageChannelSender<T>;
+
+  fn batch_message_channel<T: Debug + Send>(
+    &self,
+    capacity: usize,
+  ) -> (Self::Sender<T>, Self::Receiver<T>) {
+    let (batch_tx, batch_rx) = tokio::sync::mpsc::channel::<T>(capacity);
+    (batch_tx.into(), batch_rx.into())
+  }
+}
+
+#[derive(Debug)]
+pub struct BatchMessageChannelSender<T: Send> {
+  sender: tokio::sync::mpsc::Sender<T>,
+}
+
+impl<T: Send> From<tokio::sync::mpsc::Sender<T>>
+  for BatchMessageChannelSender<T>
+{
+  fn from(sender: tokio::sync::mpsc::Sender<T>) -> Self {
+    Self { sender }
+  }
+}
+
+impl<T: Send> opentelemetry_sdk::runtime::TrySend
+  for BatchMessageChannelSender<T>
+{
+  type Message = T;
+
+  fn try_send(
+    &self,
+    item: Self::Message,
+  ) -> Result<(), opentelemetry_sdk::runtime::TrySendError> {
+    self.sender.try_send(item).map_err(|err| match err {
+      tokio::sync::mpsc::error::TrySendError::Full(_) => {
+        opentelemetry_sdk::runtime::TrySendError::ChannelFull
+      }
+      tokio::sync::mpsc::error::TrySendError::Closed(_) => {
+        opentelemetry_sdk::runtime::TrySendError::ChannelClosed
+      }
+    })
+  }
+}
+
+pub struct BatchMessageChannelReceiver<T> {
+  receiver: tokio::sync::mpsc::Receiver<T>,
+}
+
+impl<T> From<tokio::sync::mpsc::Receiver<T>>
+  for BatchMessageChannelReceiver<T>
+{
+  fn from(receiver: tokio::sync::mpsc::Receiver<T>) -> Self {
+    Self { receiver }
+  }
+}
+
+impl<T> Stream for BatchMessageChannelReceiver<T> {
+  type Item = T;
+
+  fn poll_next(
+    mut self: Pin<&mut Self>,
+    cx: &mut Context<'_>,
+  ) -> Poll<Option<Self::Item>> {
+    self.receiver.poll_recv(cx)
+  }
+}
+
+mod hyper_client {
+  use http_body_util::BodyExt;
+  use http_body_util::Full;
+  use hyper::body::Body as HttpBody;
+  use hyper::body::Frame;
+  use hyper_util::client::legacy::connect::HttpConnector;
+  use hyper_util::client::legacy::Client;
+  use opentelemetry_http::Bytes;
+  use opentelemetry_http::HttpError;
+  use opentelemetry_http::Request;
+  use opentelemetry_http::Response;
+  use opentelemetry_http::ResponseExt;
+  use std::fmt::Debug;
+  use std::pin::Pin;
+  use std::task::Poll;
+  use std::task::{self};
+
+  use super::OtelSharedRuntime;
+
+  // same as opentelemetry_http::HyperClient except it uses OtelSharedRuntime
+  #[derive(Debug, Clone)]
+  pub struct HyperClient {
+    inner: Client<HttpConnector, Body>,
+  }
+
+  impl HyperClient {
+    pub fn new() -> Self {
+      Self {
+        inner: Client::builder(OtelSharedRuntime).build(HttpConnector::new()),
+      }
+    }
+  }
+
+  #[async_trait::async_trait]
+  impl opentelemetry_http::HttpClient for HyperClient {
+    async fn send(
+      &self,
+      request: Request<Vec<u8>>,
+    ) -> Result<Response<Bytes>, HttpError> {
+      let (parts, body) = request.into_parts();
+      let request = Request::from_parts(parts, Body(Full::from(body)));
+      let mut response = self.inner.request(request).await?;
+      let headers = std::mem::take(response.headers_mut());
+
+      let mut http_response = Response::builder()
+        .status(response.status())
+        .body(response.into_body().collect().await?.to_bytes())?;
+      *http_response.headers_mut() = headers;
+
+      Ok(http_response.error_for_status()?)
+    }
+  }
+
+  #[pin_project::pin_project]
+  pub struct Body(#[pin] Full<Bytes>);
+
+  impl HttpBody for Body {
+    type Data = Bytes;
+    type Error = Box<dyn std::error::Error + Send + Sync + 'static>;
+
+    #[inline]
+    fn poll_frame(
+      self: Pin<&mut Self>,
+      cx: &mut task::Context<'_>,
+    ) -> Poll<Option<Result<Frame<Self::Data>, Self::Error>>> {
+      self.project().0.poll_frame(cx).map_err(Into::into)
+    }
+
+    #[inline]
+    fn is_end_stream(&self) -> bool {
+      self.0.is_end_stream()
+    }
+
+    #[inline]
+    fn size_hint(&self) -> hyper::body::SizeHint {
+      self.0.size_hint()
+    }
+  }
+}
+
+static OTEL_PROCESSORS: OnceCell<(SpanProcessor, LogProcessor)> =
+  OnceCell::new();
+
+pub fn init(config: OtelConfig) -> anyhow::Result<()> {
+  // Parse the `OTEL_EXPORTER_OTLP_PROTOCOL` variable. The opentelemetry_*
+  // crates don't do this automatically.
+  // TODO(piscisaureus): enable GRPC support.
+  let protocol = match env::var("OTEL_EXPORTER_OTLP_PROTOCOL").as_deref() {
+    Ok("http/protobuf") => Protocol::HttpBinary,
+    Ok("http/json") => Protocol::HttpJson,
+    Ok("") | Err(env::VarError::NotPresent) => {
+      return Ok(());
+    }
+    Ok(protocol) => {
+      return Err(anyhow!(
+        "Env var OTEL_EXPORTER_OTLP_PROTOCOL specifies an unsupported protocol: {}",
+        protocol
+      ));
+    }
+    Err(err) => {
+      return Err(anyhow!(
+        "Failed to read env var OTEL_EXPORTER_OTLP_PROTOCOL: {}",
+        err
+      ));
+    }
+  };
+
+  // Define the resource attributes that will be attached to all log records.
+  // These attributes are sourced as follows (in order of precedence):
+  //   * The `service.name` attribute from the `OTEL_SERVICE_NAME` env var.
+  //   * Additional attributes from the `OTEL_RESOURCE_ATTRIBUTES` env var.
+  //   * Default attribute values defined here.
+  // TODO(piscisaureus): add more default attributes (e.g. script path).
+  let mut resource = Resource::default();
+
+  // Add the runtime name and version to the resource attributes. Also override
+  // the `telemetry.sdk` attributes to include the Deno runtime.
+  resource = resource.merge(&Resource::new(vec![
+    KeyValue::new(PROCESS_RUNTIME_NAME, config.runtime_name),
+    KeyValue::new(PROCESS_RUNTIME_VERSION, config.runtime_version.clone()),
+    KeyValue::new(
+      TELEMETRY_SDK_LANGUAGE,
+      format!(
+        "deno-{}",
+        resource.get(Key::new(TELEMETRY_SDK_LANGUAGE)).unwrap()
+      ),
+    ),
+    KeyValue::new(
+      TELEMETRY_SDK_NAME,
+      format!(
+        "deno-{}",
+        resource.get(Key::new(TELEMETRY_SDK_NAME)).unwrap()
+      ),
+    ),
+    KeyValue::new(
+      TELEMETRY_SDK_VERSION,
+      format!(
+        "{}-{}",
+        config.runtime_version,
+        resource.get(Key::new(TELEMETRY_SDK_VERSION)).unwrap()
+      ),
+    ),
+  ]));
+
+  // The OTLP endpoint is automatically picked up from the
+  // `OTEL_EXPORTER_OTLP_ENDPOINT` environment variable. Additional headers can
+  // be specified using `OTEL_EXPORTER_OTLP_HEADERS`.
+
+  let client = hyper_client::HyperClient::new();
+
+  let span_exporter = HttpExporterBuilder::default()
+    .with_http_client(client.clone())
+    .with_protocol(protocol)
+    .build_span_exporter()?;
+  let mut span_processor =
+    BatchSpanProcessor::builder(span_exporter, OtelSharedRuntime).build();
+  span_processor.set_resource(&resource);
+
+  let log_exporter = HttpExporterBuilder::default()
+    .with_http_client(client)
+    .with_protocol(protocol)
+    .build_log_exporter()?;
+  let log_processor =
+    BatchLogProcessor::builder(log_exporter, OtelSharedRuntime).build();
+  log_processor.set_resource(&resource);
+
+  OTEL_PROCESSORS
+    .set((span_processor, log_processor))
+    .map_err(|_| anyhow!("failed to init otel"))?;
+
+  Ok(())
+}
+
+/// This function is called by the runtime whenever it is about to call
+/// `process::exit()`, to ensure that all OpenTelemetry logs are properly
+/// flushed before the process terminates.
+pub fn flush() {
+  if let Some((span_processor, log_processor)) = OTEL_PROCESSORS.get() {
+    let _ = span_processor.force_flush();
+    let _ = log_processor.force_flush();
+  }
+}
+
+pub fn handle_log(record: &log::Record) {
+  use log::Level;
+
+  let Some((_, log_processor)) = OTEL_PROCESSORS.get() else {
+    return;
+  };
+
+  let mut log_record = LogRecord::default();
+
+  log_record.set_observed_timestamp(SystemTime::now());
+  log_record.set_severity_number(match record.level() {
+    Level::Error => Severity::Error,
+    Level::Warn => Severity::Warn,
+    Level::Info => Severity::Info,
+    Level::Debug => Severity::Debug,
+    Level::Trace => Severity::Trace,
+  });
+  log_record.set_severity_text(record.level().as_str());
+  log_record.set_body(record.args().to_string().into());
+  log_record.set_target(record.metadata().target().to_string());
+
+  struct Visitor<'s>(&'s mut LogRecord);
+
+  impl<'s, 'kvs> log::kv::VisitSource<'kvs> for Visitor<'s> {
+    fn visit_pair(
+      &mut self,
+      key: log::kv::Key<'kvs>,
+      value: log::kv::Value<'kvs>,
+    ) -> Result<(), log::kv::Error> {
+      #[allow(clippy::manual_map)]
+      let value = if let Some(v) = value.to_bool() {
+        Some(AnyValue::Boolean(v))
+      } else if let Some(v) = value.to_borrowed_str() {
+        Some(AnyValue::String(v.to_owned().into()))
+      } else if let Some(v) = value.to_f64() {
+        Some(AnyValue::Double(v))
+      } else if let Some(v) = value.to_i64() {
+        Some(AnyValue::Int(v))
+      } else {
+        None
+      };
+
+      if let Some(value) = value {
+        let key = Key::from(key.as_str().to_owned());
+        self.0.add_attribute(key, value);
+      }
+
+      Ok(())
+    }
+  }
+
+  let _ = record.key_values().visit(&mut Visitor(&mut log_record));
+
+  log_processor.emit(
+    &mut log_record,
+    &InstrumentationScope::builder("deno").build(),
+  );
+}
+
+#[op2(fast)]
+fn op_otel_log(
+  #[string] message: String,
+  #[smi] level: i32,
+  #[string] trace_id: &str,
+  #[string] span_id: &str,
+  #[smi] trace_flags: u8,
+) {
+  let Some((_, log_processor)) = OTEL_PROCESSORS.get() else {
+    return;
+  };
+
+  // Convert the integer log level that ext/console uses to the corresponding
+  // OpenTelemetry log severity.
+  let severity = match level {
+    ..=0 => Severity::Debug,
+    1 => Severity::Info,
+    2 => Severity::Warn,
+    3.. => Severity::Error,
+  };
+
+  let mut log_record = LogRecord::default();
+
+  log_record.set_observed_timestamp(SystemTime::now());
+  log_record.set_body(message.into());
+  log_record.set_severity_number(severity);
+  log_record.set_severity_text(severity.name());
+  if let (Ok(trace_id), Ok(span_id)) =
+    (TraceId::from_hex(trace_id), SpanId::from_hex(span_id))
+  {
+    log_record.set_trace_context(
+      trace_id,
+      span_id,
+      Some(TraceFlags::new(trace_flags)),
+    );
+  }
+
+  log_processor.emit(
+    &mut log_record,
+    &InstrumentationScope::builder("deno").build(),
+  );
+}
+
+struct TemporarySpan(SpanData);
+
+#[allow(clippy::too_many_arguments)]
+#[op2(fast)]
+fn op_otel_span_start<'s>(
+  scope: &mut v8::HandleScope<'s>,
+  state: &mut OpState,
+  trace_id: v8::Local<'s, v8::Value>,
+  span_id: v8::Local<'s, v8::Value>,
+  parent_span_id: v8::Local<'s, v8::Value>,
+  #[smi] span_kind: u8,
+  name: v8::Local<'s, v8::Value>,
+  start_time: f64,
+  end_time: f64,
+) -> Result<(), anyhow::Error> {
+  if let Some(temporary_span) = state.try_take::<TemporarySpan>() {
+    let Some((span_processor, _)) = OTEL_PROCESSORS.get() else {
+      return Ok(());
+    };
+    span_processor.on_end(temporary_span.0);
+  };
+
+  let trace_id = {
+    let x = v8::ValueView::new(scope, trace_id.try_cast()?);
+    match x.data() {
+      v8::ValueViewData::OneByte(bytes) => {
+        TraceId::from_hex(&String::from_utf8_lossy(bytes))?
+      }
+      _ => return Err(anyhow!("invalid trace_id")),
+    }
+  };
+
+  let span_id = {
+    let x = v8::ValueView::new(scope, span_id.try_cast()?);
+    match x.data() {
+      v8::ValueViewData::OneByte(bytes) => {
+        SpanId::from_hex(&String::from_utf8_lossy(bytes))?
+      }
+      _ => return Err(anyhow!("invalid span_id")),
+    }
+  };
+
+  let parent_span_id = {
+    let x = v8::ValueView::new(scope, parent_span_id.try_cast()?);
+    match x.data() {
+      v8::ValueViewData::OneByte(bytes) => {
+        let s = String::from_utf8_lossy(bytes);
+        if s.is_empty() {
+          SpanId::INVALID
+        } else {
+          SpanId::from_hex(&s)?
+        }
+      }
+      _ => return Err(anyhow!("invalid parent_span_id")),
+    }
+  };
+
+  let name = {
+    let x = v8::ValueView::new(scope, name.try_cast()?);
+    match x.data() {
+      v8::ValueViewData::OneByte(bytes) => {
+        String::from_utf8_lossy(bytes).into_owned()
+      }
+      v8::ValueViewData::TwoByte(bytes) => String::from_utf16_lossy(bytes),
+    }
+  };
+
+  let temporary_span = TemporarySpan(SpanData {
+    span_context: SpanContext::new(
+      trace_id,
+      span_id,
+      TraceFlags::SAMPLED,
+      false,
+      Default::default(),
+    ),
+    parent_span_id,
+    span_kind: match span_kind {
+      0 => SpanKind::Internal,
+      1 => SpanKind::Server,
+      2 => SpanKind::Client,
+      3 => SpanKind::Producer,
+      4 => SpanKind::Consumer,
+      _ => return Err(anyhow!("invalid span kind")),
+    },
+    name: Cow::Owned(name),
+    start_time: SystemTime::UNIX_EPOCH
+      .checked_add(std::time::Duration::from_secs_f64(start_time))
+      .ok_or_else(|| anyhow!("invalid start time"))?,
+    end_time: SystemTime::UNIX_EPOCH
+      .checked_add(std::time::Duration::from_secs_f64(end_time))
+      .ok_or_else(|| anyhow!("invalid start time"))?,
+    attributes: Vec::new(),
+    dropped_attributes_count: 0,
+    events: Default::default(),
+    links: Default::default(),
+    status: SpanStatus::Unset,
+    instrumentation_scope: InstrumentationScope::builder("deno").build(),
+  });
+  state.put(temporary_span);
+
+  Ok(())
+}
+
+#[op2(fast)]
+fn op_otel_span_continue(
+  state: &mut OpState,
+  #[smi] status: u8,
+  #[string] error_description: Cow<'_, str>,
+) {
+  if let Some(temporary_span) = state.try_borrow_mut::<TemporarySpan>() {
+    temporary_span.0.status = match status {
+      0 => SpanStatus::Unset,
+      1 => SpanStatus::Ok,
+      2 => SpanStatus::Error {
+        description: Cow::Owned(error_description.into_owned()),
+      },
+      _ => return,
+    };
+  }
+}
+
+macro_rules! attr {
+  ($scope:ident, $temporary_span:ident, $name:ident, $value:ident) => {
+    let name = if let Ok(name) = $name.try_cast() {
+      let view = v8::ValueView::new($scope, name);
+      match view.data() {
+        v8::ValueViewData::OneByte(bytes) => {
+          Some(String::from_utf8_lossy(bytes).into_owned())
+        }
+        v8::ValueViewData::TwoByte(bytes) => {
+          Some(String::from_utf16_lossy(bytes))
+        }
+      }
+    } else {
+      None
+    };
+    let value = if let Ok(string) = $value.try_cast::<v8::String>() {
+      Some(Value::String(StringValue::from({
+        let x = v8::ValueView::new($scope, string);
+        match x.data() {
+          v8::ValueViewData::OneByte(bytes) => {
+            String::from_utf8_lossy(bytes).into_owned()
+          }
+          v8::ValueViewData::TwoByte(bytes) => String::from_utf16_lossy(bytes),
+        }
+      })))
+    } else if let Ok(number) = $value.try_cast::<v8::Number>() {
+      Some(Value::F64(number.value()))
+    } else if let Ok(boolean) = $value.try_cast::<v8::Boolean>() {
+      Some(Value::Bool(boolean.is_true()))
+    } else if let Ok(bigint) = $value.try_cast::<v8::BigInt>() {
+      let (i64_value, _lossless) = bigint.i64_value();
+      Some(Value::I64(i64_value))
+    } else {
+      None
+    };
+    if let (Some(name), Some(value)) = (name, value) {
+      $temporary_span
+        .0
+        .attributes
+        .push(KeyValue::new(name, value));
+    } else {
+      $temporary_span.0.dropped_attributes_count += 1;
+    }
+  };
+}
+
+#[op2(fast)]
+fn op_otel_span_attribute<'s>(
+  scope: &mut v8::HandleScope<'s>,
+  state: &mut OpState,
+  #[smi] capacity: u32,
+  key: v8::Local<'s, v8::Value>,
+  value: v8::Local<'s, v8::Value>,
+) {
+  if let Some(temporary_span) = state.try_borrow_mut::<TemporarySpan>() {
+    temporary_span.0.attributes.reserve_exact(
+      (capacity as usize) - temporary_span.0.attributes.capacity(),
+    );
+    attr!(scope, temporary_span, key, value);
+  }
+}
+
+#[op2(fast)]
+fn op_otel_span_attribute2<'s>(
+  scope: &mut v8::HandleScope<'s>,
+  state: &mut OpState,
+  #[smi] capacity: u32,
+  key1: v8::Local<'s, v8::Value>,
+  value1: v8::Local<'s, v8::Value>,
+  key2: v8::Local<'s, v8::Value>,
+  value2: v8::Local<'s, v8::Value>,
+) {
+  if let Some(temporary_span) = state.try_borrow_mut::<TemporarySpan>() {
+    temporary_span.0.attributes.reserve_exact(
+      (capacity as usize) - temporary_span.0.attributes.capacity(),
+    );
+    attr!(scope, temporary_span, key1, value1);
+    attr!(scope, temporary_span, key2, value2);
+  }
+}
+
+#[allow(clippy::too_many_arguments)]
+#[op2(fast)]
+fn op_otel_span_attribute3<'s>(
+  scope: &mut v8::HandleScope<'s>,
+  state: &mut OpState,
+  #[smi] capacity: u32,
+  key1: v8::Local<'s, v8::Value>,
+  value1: v8::Local<'s, v8::Value>,
+  key2: v8::Local<'s, v8::Value>,
+  value2: v8::Local<'s, v8::Value>,
+  key3: v8::Local<'s, v8::Value>,
+  value3: v8::Local<'s, v8::Value>,
+) {
+  if let Some(temporary_span) = state.try_borrow_mut::<TemporarySpan>() {
+    temporary_span.0.attributes.reserve_exact(
+      (capacity as usize) - temporary_span.0.attributes.capacity(),
+    );
+    attr!(scope, temporary_span, key1, value1);
+    attr!(scope, temporary_span, key2, value2);
+    attr!(scope, temporary_span, key3, value3);
+  }
+}
+
+#[op2(fast)]
+fn op_otel_span_flush(state: &mut OpState) {
+  let Some(temporary_span) = state.try_take::<TemporarySpan>() else {
+    return;
+  };
+
+  let Some((span_processor, _)) = OTEL_PROCESSORS.get() else {
+    return;
+  };
+
+  span_processor.on_end(temporary_span.0);
+}
diff --git a/runtime/ops/permissions.rs b/runtime/ops/permissions.rs
index 9b46dd0193..9ad963f3bc 100644
--- a/runtime/ops/permissions.rs
+++ b/runtime/ops/permissions.rs
@@ -1,16 +1,11 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use ::deno_permissions::parse_sys_kind;
-use ::deno_permissions::PermissionDescriptorParser;
 use ::deno_permissions::PermissionState;
 use ::deno_permissions::PermissionsContainer;
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use serde::Deserialize;
 use serde::Serialize;
-use std::sync::Arc;
 
 deno_core::extension!(
   deno_permissions,
@@ -19,12 +14,6 @@ deno_core::extension!(
     op_revoke_permission,
     op_request_permission,
   ],
-  options = {
-    permission_desc_parser: Arc<dyn PermissionDescriptorParser>,
-  },
-  state = |state, options| {
-    state.put(options.permission_desc_parser);
-  },
 );
 
 #[derive(Deserialize)]
@@ -56,74 +45,36 @@ impl From<PermissionState> for PermissionStatus {
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum PermissionError {
+  #[error("No such permission name: {0}")]
+  InvalidPermissionName(String),
+  #[error("{0}")]
+  PathResolve(#[from] ::deno_permissions::PathResolveError),
+  #[error("{0}")]
+  NetDescriptorParse(#[from] ::deno_permissions::NetDescriptorParseError),
+  #[error("{0}")]
+  SysDescriptorParse(#[from] ::deno_permissions::SysDescriptorParseError),
+  #[error("{0}")]
+  RunDescriptorParse(#[from] ::deno_permissions::RunDescriptorParseError),
+}
+
 #[op2]
 #[serde]
 pub fn op_query_permission(
   state: &mut OpState,
   #[serde] args: PermissionArgs,
-) -> Result<PermissionStatus, AnyError> {
-  let permissions_container = state.borrow::<PermissionsContainer>();
-  // todo(dsherret): don't have this function use the properties of
-  // permission container
-  let desc_parser = &permissions_container.descriptor_parser;
-  let permissions = permissions_container.inner.lock();
-  let path = args.path.as_deref();
+) -> Result<PermissionStatus, PermissionError> {
+  let permissions = state.borrow::<PermissionsContainer>();
   let perm = match args.name.as_ref() {
-    "read" => permissions.read.query(
-      path
-        .map(|path| {
-          Result::<_, AnyError>::Ok(
-            desc_parser.parse_path_query(path)?.into_read(),
-          )
-        })
-        .transpose()?
-        .as_ref(),
-    ),
-    "write" => permissions.write.query(
-      path
-        .map(|path| {
-          Result::<_, AnyError>::Ok(
-            desc_parser.parse_path_query(path)?.into_write(),
-          )
-        })
-        .transpose()?
-        .as_ref(),
-    ),
-    "net" => permissions.net.query(
-      match args.host.as_deref() {
-        None => None,
-        Some(h) => Some(desc_parser.parse_net_descriptor(h)?),
-      }
-      .as_ref(),
-    ),
-    "env" => permissions.env.query(args.variable.as_deref()),
-    "sys" => permissions
-      .sys
-      .query(args.kind.as_deref().map(parse_sys_kind).transpose()?),
-    "run" => permissions.run.query(
-      args
-        .command
-        .as_deref()
-        .map(|request| desc_parser.parse_run_query(request))
-        .transpose()?
-        .as_ref(),
-    ),
-    "ffi" => permissions.ffi.query(
-      path
-        .map(|path| {
-          Result::<_, AnyError>::Ok(
-            desc_parser.parse_path_query(path)?.into_ffi(),
-          )
-        })
-        .transpose()?
-        .as_ref(),
-    ),
-    n => {
-      return Err(custom_error(
-        "ReferenceError",
-        format!("No such permission name: {n}"),
-      ))
-    }
+    "read" => permissions.query_read(args.path.as_deref())?,
+    "write" => permissions.query_write(args.path.as_deref())?,
+    "net" => permissions.query_net(args.host.as_deref())?,
+    "env" => permissions.query_env(args.variable.as_deref()),
+    "sys" => permissions.query_sys(args.kind.as_deref())?,
+    "run" => permissions.query_run(args.command.as_deref())?,
+    "ffi" => permissions.query_ffi(args.path.as_deref())?,
+    _ => return Err(PermissionError::InvalidPermissionName(args.name)),
   };
   Ok(PermissionStatus::from(perm))
 }
@@ -133,69 +84,17 @@ pub fn op_query_permission(
 pub fn op_revoke_permission(
   state: &mut OpState,
   #[serde] args: PermissionArgs,
-) -> Result<PermissionStatus, AnyError> {
-  // todo(dsherret): don't have this function use the properties of
-  // permission container
-  let permissions_container = state.borrow_mut::<PermissionsContainer>();
-  let desc_parser = &permissions_container.descriptor_parser;
-  let mut permissions = permissions_container.inner.lock();
-  let path = args.path.as_deref();
+) -> Result<PermissionStatus, PermissionError> {
+  let permissions = state.borrow::<PermissionsContainer>();
   let perm = match args.name.as_ref() {
-    "read" => permissions.read.revoke(
-      path
-        .map(|path| {
-          Result::<_, AnyError>::Ok(
-            desc_parser.parse_path_query(path)?.into_read(),
-          )
-        })
-        .transpose()?
-        .as_ref(),
-    ),
-    "write" => permissions.write.revoke(
-      path
-        .map(|path| {
-          Result::<_, AnyError>::Ok(
-            desc_parser.parse_path_query(path)?.into_write(),
-          )
-        })
-        .transpose()?
-        .as_ref(),
-    ),
-    "net" => permissions.net.revoke(
-      match args.host.as_deref() {
-        None => None,
-        Some(h) => Some(desc_parser.parse_net_descriptor(h)?),
-      }
-      .as_ref(),
-    ),
-    "env" => permissions.env.revoke(args.variable.as_deref()),
-    "sys" => permissions
-      .sys
-      .revoke(args.kind.as_deref().map(parse_sys_kind).transpose()?),
-    "run" => permissions.run.revoke(
-      args
-        .command
-        .as_deref()
-        .map(|request| desc_parser.parse_run_query(request))
-        .transpose()?
-        .as_ref(),
-    ),
-    "ffi" => permissions.ffi.revoke(
-      path
-        .map(|path| {
-          Result::<_, AnyError>::Ok(
-            desc_parser.parse_path_query(path)?.into_ffi(),
-          )
-        })
-        .transpose()?
-        .as_ref(),
-    ),
-    n => {
-      return Err(custom_error(
-        "ReferenceError",
-        format!("No such permission name: {n}"),
-      ))
-    }
+    "read" => permissions.revoke_read(args.path.as_deref())?,
+    "write" => permissions.revoke_write(args.path.as_deref())?,
+    "net" => permissions.revoke_net(args.host.as_deref())?,
+    "env" => permissions.revoke_env(args.variable.as_deref()),
+    "sys" => permissions.revoke_sys(args.kind.as_deref())?,
+    "run" => permissions.revoke_run(args.command.as_deref())?,
+    "ffi" => permissions.revoke_ffi(args.path.as_deref())?,
+    _ => return Err(PermissionError::InvalidPermissionName(args.name)),
   };
   Ok(PermissionStatus::from(perm))
 }
@@ -205,69 +104,17 @@ pub fn op_revoke_permission(
 pub fn op_request_permission(
   state: &mut OpState,
   #[serde] args: PermissionArgs,
-) -> Result<PermissionStatus, AnyError> {
-  // todo(dsherret): don't have this function use the properties of
-  // permission container
-  let permissions_container = state.borrow_mut::<PermissionsContainer>();
-  let desc_parser = &permissions_container.descriptor_parser;
-  let mut permissions = permissions_container.inner.lock();
-  let path = args.path.as_deref();
+) -> Result<PermissionStatus, PermissionError> {
+  let permissions = state.borrow::<PermissionsContainer>();
   let perm = match args.name.as_ref() {
-    "read" => permissions.read.request(
-      path
-        .map(|path| {
-          Result::<_, AnyError>::Ok(
-            desc_parser.parse_path_query(path)?.into_read(),
-          )
-        })
-        .transpose()?
-        .as_ref(),
-    ),
-    "write" => permissions.write.request(
-      path
-        .map(|path| {
-          Result::<_, AnyError>::Ok(
-            desc_parser.parse_path_query(path)?.into_write(),
-          )
-        })
-        .transpose()?
-        .as_ref(),
-    ),
-    "net" => permissions.net.request(
-      match args.host.as_deref() {
-        None => None,
-        Some(h) => Some(desc_parser.parse_net_descriptor(h)?),
-      }
-      .as_ref(),
-    ),
-    "env" => permissions.env.request(args.variable.as_deref()),
-    "sys" => permissions
-      .sys
-      .request(args.kind.as_deref().map(parse_sys_kind).transpose()?),
-    "run" => permissions.run.request(
-      args
-        .command
-        .as_deref()
-        .map(|request| desc_parser.parse_run_query(request))
-        .transpose()?
-        .as_ref(),
-    ),
-    "ffi" => permissions.ffi.request(
-      path
-        .map(|path| {
-          Result::<_, AnyError>::Ok(
-            desc_parser.parse_path_query(path)?.into_ffi(),
-          )
-        })
-        .transpose()?
-        .as_ref(),
-    ),
-    n => {
-      return Err(custom_error(
-        "ReferenceError",
-        format!("No such permission name: {n}"),
-      ))
-    }
+    "read" => permissions.request_read(args.path.as_deref())?,
+    "write" => permissions.request_write(args.path.as_deref())?,
+    "net" => permissions.request_net(args.host.as_deref())?,
+    "env" => permissions.request_env(args.variable.as_deref()),
+    "sys" => permissions.request_sys(args.kind.as_deref())?,
+    "run" => permissions.request_run(args.command.as_deref())?,
+    "ffi" => permissions.request_ffi(args.path.as_deref())?,
+    _ => return Err(PermissionError::InvalidPermissionName(args.name)),
   };
   Ok(PermissionStatus::from(perm))
 }
diff --git a/runtime/ops/process.rs b/runtime/ops/process.rs
index 530dcf49be..ee2f660dcc 100644
--- a/runtime/ops/process.rs
+++ b/runtime/ops/process.rs
@@ -1,8 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::anyhow::Context;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::serde_json;
 use deno_core::AsyncMutFuture;
@@ -35,6 +32,7 @@ use tokio::process::Command;
 #[cfg(windows)]
 use std::os::windows::process::CommandExt;
 
+use crate::ops::signal::SignalError;
 #[cfg(unix)]
 use std::os::unix::prelude::ExitStatusExt;
 #[cfg(unix)]
@@ -105,11 +103,12 @@ impl StdioOrRid {
   pub fn as_stdio(
     &self,
     state: &mut OpState,
-  ) -> Result<std::process::Stdio, AnyError> {
+  ) -> Result<std::process::Stdio, ProcessError> {
     match &self {
       StdioOrRid::Stdio(val) => Ok(val.as_stdio()),
       StdioOrRid::Rid(rid) => {
         FileResource::with_file(state, *rid, |file| Ok(file.as_stdio()?))
+          .map_err(ProcessError::Resource)
       }
     }
   }
@@ -191,6 +190,41 @@ pub struct SpawnArgs {
   needs_npm_process_state: bool,
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum ProcessError {
+  #[error("Failed to spawn '{command}': {error}")]
+  SpawnFailed {
+    command: String,
+    #[source]
+    error: Box<ProcessError>,
+  },
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[cfg(unix)]
+  #[error(transparent)]
+  Nix(nix::Error),
+  #[error("failed resolving cwd: {0}")]
+  FailedResolvingCwd(#[source] std::io::Error),
+  #[error(transparent)]
+  Permission(#[from] deno_permissions::PermissionCheckError),
+  #[error(transparent)]
+  RunPermission(#[from] CheckRunPermissionError),
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  BorrowMut(std::cell::BorrowMutError),
+  #[error(transparent)]
+  Which(which::Error),
+  #[error("Child process has already terminated.")]
+  ChildProcessAlreadyTerminated,
+  #[error("Invalid pid")]
+  InvalidPid,
+  #[error(transparent)]
+  Signal(#[from] SignalError),
+  #[error("Missing cmd")]
+  MissingCmd, // only for Deno.run
+}
+
 #[derive(Deserialize)]
 #[serde(rename_all = "camelCase")]
 pub struct ChildStdio {
@@ -208,7 +242,7 @@ pub struct ChildStatus {
 }
 
 impl TryFrom<ExitStatus> for ChildStatus {
-  type Error = AnyError;
+  type Error = SignalError;
 
   fn try_from(status: ExitStatus) -> Result<Self, Self::Error> {
     let code = status.code();
@@ -259,7 +293,7 @@ type CreateCommand = (
 
 pub fn npm_process_state_tempfile(
   contents: &[u8],
-) -> Result<deno_io::RawIoHandle, AnyError> {
+) -> Result<deno_io::RawIoHandle, std::io::Error> {
   let mut temp_file = tempfile::tempfile()?;
   temp_file.write_all(contents)?;
   let handle = temp_file.into_raw_io_handle();
@@ -301,7 +335,7 @@ fn create_command(
   state: &mut OpState,
   mut args: SpawnArgs,
   api_name: &str,
-) -> Result<CreateCommand, AnyError> {
+) -> Result<CreateCommand, ProcessError> {
   let maybe_npm_process_state = if args.needs_npm_process_state {
     let provider = state.borrow::<NpmProcessStateProviderRc>();
     let process_state = provider.get_npm_process_state();
@@ -505,7 +539,7 @@ fn spawn_child(
   ipc_pipe_rid: Option<ResourceId>,
   extra_pipe_rids: Vec<Option<ResourceId>>,
   detached: bool,
-) -> Result<Child, AnyError> {
+) -> Result<Child, ProcessError> {
   let mut command = tokio::process::Command::from(command);
   // TODO(@crowlkats): allow detaching processes.
   //  currently deno will orphan a process when exiting with an error or Deno.exit()
@@ -554,10 +588,10 @@ fn spawn_child(
         }
       }
 
-      return Err(AnyError::from(err).context(format!(
-        "Failed to spawn '{}'",
-        command.get_program().to_string_lossy()
-      )));
+      return Err(ProcessError::SpawnFailed {
+        command: command.get_program().to_string_lossy().to_string(),
+        error: Box::new(err.into()),
+      });
     }
   };
 
@@ -600,11 +634,19 @@ fn compute_run_cmd_and_check_permissions(
   arg_clear_env: bool,
   state: &mut OpState,
   api_name: &str,
-) -> Result<(PathBuf, RunEnv), AnyError> {
-  let run_env = compute_run_env(arg_cwd, arg_envs, arg_clear_env)
-    .with_context(|| format!("Failed to spawn '{}'", arg_cmd))?;
-  let cmd = resolve_cmd(arg_cmd, &run_env)
-    .with_context(|| format!("Failed to spawn '{}'", arg_cmd))?;
+) -> Result<(PathBuf, RunEnv), ProcessError> {
+  let run_env =
+    compute_run_env(arg_cwd, arg_envs, arg_clear_env).map_err(|e| {
+      ProcessError::SpawnFailed {
+        command: arg_cmd.to_string(),
+        error: Box::new(e),
+      }
+    })?;
+  let cmd =
+    resolve_cmd(arg_cmd, &run_env).map_err(|e| ProcessError::SpawnFailed {
+      command: arg_cmd.to_string(),
+      error: Box::new(e),
+    })?;
   check_run_permission(
     state,
     &RunQueryDescriptor::Path {
@@ -631,9 +673,10 @@ fn compute_run_env(
   arg_cwd: Option<&str>,
   arg_envs: &[(String, String)],
   arg_clear_env: bool,
-) -> Result<RunEnv, AnyError> {
+) -> Result<RunEnv, ProcessError> {
   #[allow(clippy::disallowed_methods)]
-  let cwd = std::env::current_dir().context("failed resolving cwd")?;
+  let cwd =
+    std::env::current_dir().map_err(ProcessError::FailedResolvingCwd)?;
   let cwd = arg_cwd
     .map(|cwd_arg| resolve_path(cwd_arg, &cwd))
     .unwrap_or(cwd);
@@ -670,7 +713,7 @@ fn compute_run_env(
   Ok(RunEnv { envs, cwd })
 }
 
-fn resolve_cmd(cmd: &str, env: &RunEnv) -> Result<PathBuf, AnyError> {
+fn resolve_cmd(cmd: &str, env: &RunEnv) -> Result<PathBuf, ProcessError> {
   let is_path = cmd.contains('/');
   #[cfg(windows)]
   let is_path = is_path || cmd.contains('\\') || Path::new(&cmd).is_absolute();
@@ -683,13 +726,21 @@ fn resolve_cmd(cmd: &str, env: &RunEnv) -> Result<PathBuf, AnyError> {
       Err(which::Error::CannotFindBinaryPath) => {
         Err(std::io::Error::from(std::io::ErrorKind::NotFound).into())
       }
-      Err(err) => Err(err.into()),
+      Err(err) => Err(ProcessError::Which(err)),
     }
   }
 }
 
 fn resolve_path(path: &str, cwd: &Path) -> PathBuf {
-  deno_core::normalize_path(cwd.join(path))
+  deno_path_util::normalize_path(cwd.join(path))
+}
+
+#[derive(Debug, thiserror::Error)]
+pub enum CheckRunPermissionError {
+  #[error(transparent)]
+  Permission(#[from] deno_permissions::PermissionCheckError),
+  #[error("{0}")]
+  Other(deno_core::error::AnyError),
 }
 
 fn check_run_permission(
@@ -697,7 +748,7 @@ fn check_run_permission(
   cmd: &RunQueryDescriptor,
   run_env: &RunEnv,
   api_name: &str,
-) -> Result<(), AnyError> {
+) -> Result<(), CheckRunPermissionError> {
   let permissions = state.borrow_mut::<PermissionsContainer>();
   if !permissions.query_run_all(api_name) {
     // error the same on all platforms
@@ -705,13 +756,16 @@ fn check_run_permission(
     if !env_var_names.is_empty() {
       // we don't allow users to launch subprocesses with any LD_ or DYLD_*
       // env vars set because this allows executing code (ex. LD_PRELOAD)
-      return Err(deno_core::error::custom_error(
-        "NotCapable",
-        format!(
-          "Requires --allow-all permissions to spawn subprocess with {} environment variable{}.",
-          env_var_names.join(", "),
-          if env_var_names.len() != 1 { "s" } else { "" }
-        )
+      return Err(CheckRunPermissionError::Other(
+        deno_core::error::custom_error(
+          "NotCapable",
+          format!(
+            "Requires --allow-run permissions to spawn subprocess with {0} environment variable{1}. Alternatively, spawn with {2} environment variable{1} unset.",
+            env_var_names.join(", "),
+            if env_var_names.len() != 1 { "s" } else { "" },
+            if env_var_names.len() != 1 { "these" } else { "the" }
+          ),
+        ),
       ));
     }
     permissions.check_run(cmd, api_name)?;
@@ -754,7 +808,7 @@ fn op_spawn_child(
   state: &mut OpState,
   #[serde] args: SpawnArgs,
   #[string] api_name: String,
-) -> Result<Child, AnyError> {
+) -> Result<Child, ProcessError> {
   let detached = args.detached;
   let (command, pipe_rid, extra_pipe_rids, handles_to_close) =
     create_command(state, args, &api_name)?;
@@ -771,16 +825,23 @@ fn op_spawn_child(
 async fn op_spawn_wait(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<ChildStatus, AnyError> {
+) -> Result<ChildStatus, ProcessError> {
   let resource = state
     .borrow_mut()
     .resource_table
-    .get::<ChildResource>(rid)?;
-  let result = resource.0.try_borrow_mut()?.wait().await?.try_into();
+    .get::<ChildResource>(rid)
+    .map_err(ProcessError::Resource)?;
+  let result = resource
+    .0
+    .try_borrow_mut()
+    .map_err(ProcessError::BorrowMut)?
+    .wait()
+    .await?
+    .try_into()?;
   if let Ok(resource) = state.borrow_mut().resource_table.take_any(rid) {
     resource.close();
   }
-  result
+  Ok(result)
 }
 
 #[op2]
@@ -788,16 +849,14 @@ async fn op_spawn_wait(
 fn op_spawn_sync(
   state: &mut OpState,
   #[serde] args: SpawnArgs,
-) -> Result<SpawnOutput, AnyError> {
+) -> Result<SpawnOutput, ProcessError> {
   let stdout = matches!(args.stdio.stdout, StdioOrRid::Stdio(Stdio::Piped));
   let stderr = matches!(args.stdio.stderr, StdioOrRid::Stdio(Stdio::Piped));
   let (mut command, _, _, _) =
     create_command(state, args, "Deno.Command().outputSync()")?;
-  let output = command.output().with_context(|| {
-    format!(
-      "Failed to spawn '{}'",
-      command.get_program().to_string_lossy()
-    )
+  let output = command.output().map_err(|e| ProcessError::SpawnFailed {
+    command: command.get_program().to_string_lossy().to_string(),
+    error: Box::new(e.into()),
   })?;
 
   Ok(SpawnOutput {
@@ -820,17 +879,15 @@ fn op_spawn_kill(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   #[string] signal: String,
-) -> Result<(), AnyError> {
+) -> Result<(), ProcessError> {
   if let Ok(child_resource) = state.resource_table.get::<ChildResource>(rid) {
     deprecated::kill(child_resource.1 as i32, &signal)?;
     return Ok(());
   }
-  Err(type_error("Child process has already terminated."))
+  Err(ProcessError::ChildProcessAlreadyTerminated)
 }
 
 mod deprecated {
-  use deno_core::anyhow;
-
   use super::*;
 
   #[derive(Deserialize)]
@@ -876,9 +933,9 @@ mod deprecated {
   pub fn op_run(
     state: &mut OpState,
     #[serde] run_args: RunArgs,
-  ) -> Result<RunInfo, AnyError> {
+  ) -> Result<RunInfo, ProcessError> {
     let args = run_args.cmd;
-    let cmd = args.first().ok_or_else(|| anyhow::anyhow!("Missing cmd"))?;
+    let cmd = args.first().ok_or(ProcessError::MissingCmd)?;
     let (cmd, run_env) = compute_run_cmd_and_check_permissions(
       cmd,
       run_args.cwd.as_deref(),
@@ -990,11 +1047,12 @@ mod deprecated {
   pub async fn op_run_status(
     state: Rc<RefCell<OpState>>,
     #[smi] rid: ResourceId,
-  ) -> Result<ProcessStatus, AnyError> {
+  ) -> Result<ProcessStatus, ProcessError> {
     let resource = state
       .borrow_mut()
       .resource_table
-      .get::<ChildResource>(rid)?;
+      .get::<ChildResource>(rid)
+      .map_err(ProcessError::Resource)?;
     let mut child = resource.borrow_mut().await;
     let run_status = child.wait().await?;
     let code = run_status.code();
@@ -1017,17 +1075,17 @@ mod deprecated {
   }
 
   #[cfg(unix)]
-  pub fn kill(pid: i32, signal: &str) -> Result<(), AnyError> {
+  pub fn kill(pid: i32, signal: &str) -> Result<(), ProcessError> {
     let signo = super::super::signal::signal_str_to_int(signal)?;
     use nix::sys::signal::kill as unix_kill;
     use nix::sys::signal::Signal;
     use nix::unistd::Pid;
-    let sig = Signal::try_from(signo)?;
-    unix_kill(Pid::from_raw(pid), Option::Some(sig)).map_err(AnyError::from)
+    let sig = Signal::try_from(signo).map_err(ProcessError::Nix)?;
+    unix_kill(Pid::from_raw(pid), Some(sig)).map_err(ProcessError::Nix)
   }
 
   #[cfg(not(unix))]
-  pub fn kill(pid: i32, signal: &str) -> Result<(), AnyError> {
+  pub fn kill(pid: i32, signal: &str) -> Result<(), ProcessError> {
     use std::io::Error;
     use std::io::ErrorKind::NotFound;
     use winapi::shared::minwindef::DWORD;
@@ -1041,9 +1099,9 @@ mod deprecated {
     use winapi::um::winnt::PROCESS_TERMINATE;
 
     if !matches!(signal, "SIGKILL" | "SIGTERM") {
-      Err(type_error(format!("Invalid signal: {signal}")))
+      Err(SignalError::InvalidSignalStr(signal.to_string()).into())
     } else if pid <= 0 {
-      Err(type_error("Invalid pid"))
+      Err(ProcessError::InvalidPid)
     } else {
       let handle =
         // SAFETY: winapi call
@@ -1077,11 +1135,10 @@ mod deprecated {
     #[smi] pid: i32,
     #[string] signal: String,
     #[string] api_name: String,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), ProcessError> {
     state
       .borrow_mut::<PermissionsContainer>()
       .check_run_all(&api_name)?;
-    kill(pid, &signal)?;
-    Ok(())
+    kill(pid, &signal)
   }
 }
diff --git a/runtime/ops/runtime.rs b/runtime/ops/runtime.rs
index 419274ebd9..8d54783fc9 100644
--- a/runtime/ops/runtime.rs
+++ b/runtime/ops/runtime.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::ModuleSpecifier;
 use deno_core::OpState;
@@ -16,10 +15,9 @@ deno_core::extension!(
 
 #[op2]
 #[string]
-fn op_main_module(state: &mut OpState) -> Result<String, AnyError> {
+fn op_main_module(state: &mut OpState) -> String {
   let main_url = state.borrow::<ModuleSpecifier>();
-  let main_path = main_url.to_string();
-  Ok(main_path)
+  main_url.to_string()
 }
 
 /// This is an op instead of being done at initialization time because
diff --git a/runtime/ops/signal.rs b/runtime/ops/signal.rs
index ebc6db6d1b..e1e4ab68bc 100644
--- a/runtime/ops/signal.rs
+++ b/runtime/ops/signal.rs
@@ -1,6 +1,4 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::AsyncRefCell;
 use deno_core::CancelFuture;
@@ -46,6 +44,42 @@ deno_core::extension!(
   }
 );
 
+#[derive(Debug, thiserror::Error)]
+pub enum SignalError {
+  #[cfg(any(
+    target_os = "android",
+    target_os = "linux",
+    target_os = "openbsd",
+    target_os = "openbsd",
+    target_os = "macos",
+    target_os = "solaris",
+    target_os = "illumos"
+  ))]
+  #[error("Invalid signal: {0}")]
+  InvalidSignalStr(String),
+  #[cfg(any(
+    target_os = "android",
+    target_os = "linux",
+    target_os = "openbsd",
+    target_os = "openbsd",
+    target_os = "macos",
+    target_os = "solaris",
+    target_os = "illumos"
+  ))]
+  #[error("Invalid signal: {0}")]
+  InvalidSignalInt(libc::c_int),
+  #[cfg(target_os = "windows")]
+  #[error("Windows only supports ctrl-c (SIGINT) and ctrl-break (SIGBREAK), but got {0}")]
+  InvalidSignalStr(String),
+  #[cfg(target_os = "windows")]
+  #[error("Windows only supports ctrl-c (SIGINT) and ctrl-break (SIGBREAK), but got {0}")]
+  InvalidSignalInt(libc::c_int),
+  #[error("Binding to signal '{0}' is not allowed")]
+  SignalNotAllowed(String),
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+}
+
 #[cfg(unix)]
 #[derive(Default)]
 struct SignalState {
@@ -147,438 +181,217 @@ impl Resource for SignalStreamResource {
   }
 }
 
-#[cfg(target_os = "freebsd")]
-pub fn signal_str_to_int(s: &str) -> Result<libc::c_int, AnyError> {
-  match s {
-    "SIGHUP" => Ok(1),
-    "SIGINT" => Ok(2),
-    "SIGQUIT" => Ok(3),
-    "SIGILL" => Ok(4),
-    "SIGTRAP" => Ok(5),
-    "SIGIOT" => Ok(6),
-    "SIGABRT" => Ok(6),
-    "SIGEMT" => Ok(7),
-    "SIGFPE" => Ok(8),
-    "SIGKILL" => Ok(9),
-    "SIGBUS" => Ok(10),
-    "SIGSEGV" => Ok(11),
-    "SIGSYS" => Ok(12),
-    "SIGPIPE" => Ok(13),
-    "SIGALRM" => Ok(14),
-    "SIGTERM" => Ok(15),
-    "SIGURG" => Ok(16),
-    "SIGSTOP" => Ok(17),
-    "SIGTSTP" => Ok(18),
-    "SIGCONT" => Ok(19),
-    "SIGCHLD" => Ok(20),
-    "SIGTTIN" => Ok(21),
-    "SIGTTOU" => Ok(22),
-    "SIGIO" => Ok(23),
-    "SIGXCPU" => Ok(24),
-    "SIGXFSZ" => Ok(25),
-    "SIGVTALRM" => Ok(26),
-    "SIGPROF" => Ok(27),
-    "SIGWINCH" => Ok(28),
-    "SIGINFO" => Ok(29),
-    "SIGUSR1" => Ok(30),
-    "SIGUSR2" => Ok(31),
-    "SIGTHR" => Ok(32),
-    "SIGLIBRT" => Ok(33),
-    _ => Err(type_error(format!("Invalid signal : {}", s))),
+macro_rules! first_literal {
+  ($head:literal $(, $tail:literal)*) => {
+    $head
+  };
+}
+macro_rules! signal_dict {
+  ($(($number:literal, $($name:literal)|+)),*) => {
+    pub fn signal_str_to_int(s: &str) -> Result<libc::c_int, SignalError> {
+      match s {
+        $($($name)|* => Ok($number),)*
+        _ => Err(SignalError::InvalidSignalStr(s.to_string())),
+      }
+    }
+
+    pub fn signal_int_to_str(s: libc::c_int) -> Result<&'static str, SignalError> {
+      match s {
+        $($number => Ok(first_literal!($($name),+)),)*
+        _ => Err(SignalError::InvalidSignalInt(s)),
+      }
+    }
   }
 }
 
 #[cfg(target_os = "freebsd")]
-pub fn signal_int_to_str(s: libc::c_int) -> Result<&'static str, AnyError> {
-  match s {
-    1 => Ok("SIGHUP"),
-    2 => Ok("SIGINT"),
-    3 => Ok("SIGQUIT"),
-    4 => Ok("SIGILL"),
-    5 => Ok("SIGTRAP"),
-    6 => Ok("SIGABRT"),
-    7 => Ok("SIGEMT"),
-    8 => Ok("SIGFPE"),
-    9 => Ok("SIGKILL"),
-    10 => Ok("SIGBUS"),
-    11 => Ok("SIGSEGV"),
-    12 => Ok("SIGSYS"),
-    13 => Ok("SIGPIPE"),
-    14 => Ok("SIGALRM"),
-    15 => Ok("SIGTERM"),
-    16 => Ok("SIGURG"),
-    17 => Ok("SIGSTOP"),
-    18 => Ok("SIGTSTP"),
-    19 => Ok("SIGCONT"),
-    20 => Ok("SIGCHLD"),
-    21 => Ok("SIGTTIN"),
-    22 => Ok("SIGTTOU"),
-    23 => Ok("SIGIO"),
-    24 => Ok("SIGXCPU"),
-    25 => Ok("SIGXFSZ"),
-    26 => Ok("SIGVTALRM"),
-    27 => Ok("SIGPROF"),
-    28 => Ok("SIGWINCH"),
-    29 => Ok("SIGINFO"),
-    30 => Ok("SIGUSR1"),
-    31 => Ok("SIGUSR2"),
-    32 => Ok("SIGTHR"),
-    33 => Ok("SIGLIBRT"),
-    _ => Err(type_error(format!("Invalid signal : {}", s))),
-  }
-}
+signal_dict!(
+  (1, "SIGHUP"),
+  (2, "SIGINT"),
+  (3, "SIGQUIT"),
+  (4, "SIGILL"),
+  (5, "SIGTRAP"),
+  (6, "SIGABRT" | "SIGIOT"),
+  (7, "SIGEMT"),
+  (8, "SIGFPE"),
+  (9, "SIGKILL"),
+  (10, "SIGBUS"),
+  (11, "SIGSEGV"),
+  (12, "SIGSYS"),
+  (13, "SIGPIPE"),
+  (14, "SIGALRM"),
+  (15, "SIGTERM"),
+  (16, "SIGURG"),
+  (17, "SIGSTOP"),
+  (18, "SIGTSTP"),
+  (19, "SIGCONT"),
+  (20, "SIGCHLD"),
+  (21, "SIGTTIN"),
+  (22, "SIGTTOU"),
+  (23, "SIGIO"),
+  (24, "SIGXCPU"),
+  (25, "SIGXFSZ"),
+  (26, "SIGVTALRM"),
+  (27, "SIGPROF"),
+  (28, "SIGWINCH"),
+  (29, "SIGINFO"),
+  (30, "SIGUSR1"),
+  (31, "SIGUSR2"),
+  (32, "SIGTHR"),
+  (33, "SIGLIBRT")
+);
 
 #[cfg(target_os = "openbsd")]
-pub fn signal_str_to_int(s: &str) -> Result<libc::c_int, AnyError> {
-  match s {
-    "SIGHUP" => Ok(1),
-    "SIGINT" => Ok(2),
-    "SIGQUIT" => Ok(3),
-    "SIGILL" => Ok(4),
-    "SIGTRAP" => Ok(5),
-    "SIGIOT" => Ok(6),
-    "SIGABRT" => Ok(6),
-    "SIGEMT" => Ok(7),
-    "SIGFPE" => Ok(8),
-    "SIGKILL" => Ok(9),
-    "SIGBUS" => Ok(10),
-    "SIGSEGV" => Ok(11),
-    "SIGSYS" => Ok(12),
-    "SIGPIPE" => Ok(13),
-    "SIGALRM" => Ok(14),
-    "SIGTERM" => Ok(15),
-    "SIGURG" => Ok(16),
-    "SIGSTOP" => Ok(17),
-    "SIGTSTP" => Ok(18),
-    "SIGCONT" => Ok(19),
-    "SIGCHLD" => Ok(20),
-    "SIGTTIN" => Ok(21),
-    "SIGTTOU" => Ok(22),
-    "SIGIO" => Ok(23),
-    "SIGXCPU" => Ok(24),
-    "SIGXFSZ" => Ok(25),
-    "SIGVTALRM" => Ok(26),
-    "SIGPROF" => Ok(27),
-    "SIGWINCH" => Ok(28),
-    "SIGINFO" => Ok(29),
-    "SIGUSR1" => Ok(30),
-    "SIGUSR2" => Ok(31),
-    "SIGTHR" => Ok(32),
-    _ => Err(type_error(format!("Invalid signal : {}", s))),
-  }
-}
-
-#[cfg(target_os = "openbsd")]
-pub fn signal_int_to_str(s: libc::c_int) -> Result<&'static str, AnyError> {
-  match s {
-    1 => Ok("SIGHUP"),
-    2 => Ok("SIGINT"),
-    3 => Ok("SIGQUIT"),
-    4 => Ok("SIGILL"),
-    5 => Ok("SIGTRAP"),
-    6 => Ok("SIGABRT"),
-    7 => Ok("SIGEMT"),
-    8 => Ok("SIGFPE"),
-    9 => Ok("SIGKILL"),
-    10 => Ok("SIGBUS"),
-    11 => Ok("SIGSEGV"),
-    12 => Ok("SIGSYS"),
-    13 => Ok("SIGPIPE"),
-    14 => Ok("SIGALRM"),
-    15 => Ok("SIGTERM"),
-    16 => Ok("SIGURG"),
-    17 => Ok("SIGSTOP"),
-    18 => Ok("SIGTSTP"),
-    19 => Ok("SIGCONT"),
-    20 => Ok("SIGCHLD"),
-    21 => Ok("SIGTTIN"),
-    22 => Ok("SIGTTOU"),
-    23 => Ok("SIGIO"),
-    24 => Ok("SIGXCPU"),
-    25 => Ok("SIGXFSZ"),
-    26 => Ok("SIGVTALRM"),
-    27 => Ok("SIGPROF"),
-    28 => Ok("SIGWINCH"),
-    29 => Ok("SIGINFO"),
-    30 => Ok("SIGUSR1"),
-    31 => Ok("SIGUSR2"),
-    32 => Ok("SIGTHR"),
-    _ => Err(type_error(format!("Invalid signal : {}", s))),
-  }
-}
+signal_dict!(
+  (1, "SIGHUP"),
+  (2, "SIGINT"),
+  (3, "SIGQUIT"),
+  (4, "SIGILL"),
+  (5, "SIGTRAP"),
+  (6, "SIGABRT" | "SIGIOT"),
+  (7, "SIGEMT"),
+  (8, "SIGKILL"),
+  (10, "SIGBUS"),
+  (11, "SIGSEGV"),
+  (12, "SIGSYS"),
+  (13, "SIGPIPE"),
+  (14, "SIGALRM"),
+  (15, "SIGTERM"),
+  (16, "SIGURG"),
+  (17, "SIGSTOP"),
+  (18, "SIGTSTP"),
+  (19, "SIGCONT"),
+  (20, "SIGCHLD"),
+  (21, "SIGTTIN"),
+  (22, "SIGTTOU"),
+  (23, "SIGIO"),
+  (24, "SIGXCPU"),
+  (25, "SIGXFSZ"),
+  (26, "SIGVTALRM"),
+  (27, "SIGPROF"),
+  (28, "SIGWINCH"),
+  (29, "SIGINFO"),
+  (30, "SIGUSR1"),
+  (31, "SIGUSR2"),
+  (32, "SIGTHR")
+);
 
 #[cfg(any(target_os = "android", target_os = "linux"))]
-pub fn signal_str_to_int(s: &str) -> Result<libc::c_int, AnyError> {
-  match s {
-    "SIGHUP" => Ok(1),
-    "SIGINT" => Ok(2),
-    "SIGQUIT" => Ok(3),
-    "SIGILL" => Ok(4),
-    "SIGTRAP" => Ok(5),
-    "SIGIOT" => Ok(6),
-    "SIGABRT" => Ok(6),
-    "SIGBUS" => Ok(7),
-    "SIGFPE" => Ok(8),
-    "SIGKILL" => Ok(9),
-    "SIGUSR1" => Ok(10),
-    "SIGSEGV" => Ok(11),
-    "SIGUSR2" => Ok(12),
-    "SIGPIPE" => Ok(13),
-    "SIGALRM" => Ok(14),
-    "SIGTERM" => Ok(15),
-    "SIGSTKFLT" => Ok(16),
-    "SIGCHLD" => Ok(17),
-    "SIGCONT" => Ok(18),
-    "SIGSTOP" => Ok(19),
-    "SIGTSTP" => Ok(20),
-    "SIGTTIN" => Ok(21),
-    "SIGTTOU" => Ok(22),
-    "SIGURG" => Ok(23),
-    "SIGXCPU" => Ok(24),
-    "SIGXFSZ" => Ok(25),
-    "SIGVTALRM" => Ok(26),
-    "SIGPROF" => Ok(27),
-    "SIGWINCH" => Ok(28),
-    "SIGIO" | "SIGPOLL" => Ok(29),
-    "SIGPWR" => Ok(30),
-    "SIGSYS" | "SIGUNUSED" => Ok(31),
-    _ => Err(type_error(format!("Invalid signal : {s}"))),
-  }
-}
-
-#[cfg(any(target_os = "android", target_os = "linux"))]
-pub fn signal_int_to_str(s: libc::c_int) -> Result<&'static str, AnyError> {
-  match s {
-    1 => Ok("SIGHUP"),
-    2 => Ok("SIGINT"),
-    3 => Ok("SIGQUIT"),
-    4 => Ok("SIGILL"),
-    5 => Ok("SIGTRAP"),
-    6 => Ok("SIGABRT"),
-    7 => Ok("SIGBUS"),
-    8 => Ok("SIGFPE"),
-    9 => Ok("SIGKILL"),
-    10 => Ok("SIGUSR1"),
-    11 => Ok("SIGSEGV"),
-    12 => Ok("SIGUSR2"),
-    13 => Ok("SIGPIPE"),
-    14 => Ok("SIGALRM"),
-    15 => Ok("SIGTERM"),
-    16 => Ok("SIGSTKFLT"),
-    17 => Ok("SIGCHLD"),
-    18 => Ok("SIGCONT"),
-    19 => Ok("SIGSTOP"),
-    20 => Ok("SIGTSTP"),
-    21 => Ok("SIGTTIN"),
-    22 => Ok("SIGTTOU"),
-    23 => Ok("SIGURG"),
-    24 => Ok("SIGXCPU"),
-    25 => Ok("SIGXFSZ"),
-    26 => Ok("SIGVTALRM"),
-    27 => Ok("SIGPROF"),
-    28 => Ok("SIGWINCH"),
-    29 => Ok("SIGIO"),
-    30 => Ok("SIGPWR"),
-    31 => Ok("SIGSYS"),
-    _ => Err(type_error(format!("Invalid signal : {s}"))),
-  }
-}
+signal_dict!(
+  (1, "SIGHUP"),
+  (2, "SIGINT"),
+  (3, "SIGQUIT"),
+  (4, "SIGILL"),
+  (5, "SIGTRAP"),
+  (6, "SIGABRT" | "SIGIOT"),
+  (7, "SIGBUS"),
+  (8, "SIGFPE"),
+  (9, "SIGKILL"),
+  (10, "SIGUSR1"),
+  (11, "SIGSEGV"),
+  (12, "SIGUSR2"),
+  (13, "SIGPIPE"),
+  (14, "SIGALRM"),
+  (15, "SIGTERM"),
+  (16, "SIGSTKFLT"),
+  (17, "SIGCHLD"),
+  (18, "SIGCONT"),
+  (19, "SIGSTOP"),
+  (20, "SIGTSTP"),
+  (21, "SIGTTIN"),
+  (22, "SIGTTOU"),
+  (23, "SIGURG"),
+  (24, "SIGXCPU"),
+  (25, "SIGXFSZ"),
+  (26, "SIGVTALRM"),
+  (27, "SIGPROF"),
+  (28, "SIGWINCH"),
+  (29, "SIGIO" | "SIGPOLL"),
+  (30, "SIGPWR"),
+  (31, "SIGSYS" | "SIGUNUSED")
+);
 
 #[cfg(target_os = "macos")]
-pub fn signal_str_to_int(s: &str) -> Result<libc::c_int, AnyError> {
-  match s {
-    "SIGHUP" => Ok(1),
-    "SIGINT" => Ok(2),
-    "SIGQUIT" => Ok(3),
-    "SIGILL" => Ok(4),
-    "SIGTRAP" => Ok(5),
-    "SIGIOT" => Ok(6),
-    "SIGABRT" => Ok(6),
-    "SIGEMT" => Ok(7),
-    "SIGFPE" => Ok(8),
-    "SIGKILL" => Ok(9),
-    "SIGBUS" => Ok(10),
-    "SIGSEGV" => Ok(11),
-    "SIGSYS" => Ok(12),
-    "SIGPIPE" => Ok(13),
-    "SIGALRM" => Ok(14),
-    "SIGTERM" => Ok(15),
-    "SIGURG" => Ok(16),
-    "SIGSTOP" => Ok(17),
-    "SIGTSTP" => Ok(18),
-    "SIGCONT" => Ok(19),
-    "SIGCHLD" => Ok(20),
-    "SIGTTIN" => Ok(21),
-    "SIGTTOU" => Ok(22),
-    "SIGIO" => Ok(23),
-    "SIGXCPU" => Ok(24),
-    "SIGXFSZ" => Ok(25),
-    "SIGVTALRM" => Ok(26),
-    "SIGPROF" => Ok(27),
-    "SIGWINCH" => Ok(28),
-    "SIGINFO" => Ok(29),
-    "SIGUSR1" => Ok(30),
-    "SIGUSR2" => Ok(31),
-    _ => Err(type_error(format!("Invalid signal: {s}"))),
-  }
-}
-
-#[cfg(target_os = "macos")]
-pub fn signal_int_to_str(s: libc::c_int) -> Result<&'static str, AnyError> {
-  match s {
-    1 => Ok("SIGHUP"),
-    2 => Ok("SIGINT"),
-    3 => Ok("SIGQUIT"),
-    4 => Ok("SIGILL"),
-    5 => Ok("SIGTRAP"),
-    6 => Ok("SIGABRT"),
-    7 => Ok("SIGEMT"),
-    8 => Ok("SIGFPE"),
-    9 => Ok("SIGKILL"),
-    10 => Ok("SIGBUS"),
-    11 => Ok("SIGSEGV"),
-    12 => Ok("SIGSYS"),
-    13 => Ok("SIGPIPE"),
-    14 => Ok("SIGALRM"),
-    15 => Ok("SIGTERM"),
-    16 => Ok("SIGURG"),
-    17 => Ok("SIGSTOP"),
-    18 => Ok("SIGTSTP"),
-    19 => Ok("SIGCONT"),
-    20 => Ok("SIGCHLD"),
-    21 => Ok("SIGTTIN"),
-    22 => Ok("SIGTTOU"),
-    23 => Ok("SIGIO"),
-    24 => Ok("SIGXCPU"),
-    25 => Ok("SIGXFSZ"),
-    26 => Ok("SIGVTALRM"),
-    27 => Ok("SIGPROF"),
-    28 => Ok("SIGWINCH"),
-    29 => Ok("SIGINFO"),
-    30 => Ok("SIGUSR1"),
-    31 => Ok("SIGUSR2"),
-    _ => Err(type_error(format!("Invalid signal: {s}"))),
-  }
-}
+signal_dict!(
+  (1, "SIGHUP"),
+  (2, "SIGINT"),
+  (3, "SIGQUIT"),
+  (4, "SIGILL"),
+  (5, "SIGTRAP"),
+  (6, "SIGABRT" | "SIGIOT"),
+  (7, "SIGEMT"),
+  (8, "SIGFPE"),
+  (9, "SIGKILL"),
+  (10, "SIGBUS"),
+  (11, "SIGSEGV"),
+  (12, "SIGSYS"),
+  (13, "SIGPIPE"),
+  (14, "SIGALRM"),
+  (15, "SIGTERM"),
+  (16, "SIGURG"),
+  (17, "SIGSTOP"),
+  (18, "SIGTSTP"),
+  (19, "SIGCONT"),
+  (20, "SIGCHLD"),
+  (21, "SIGTTIN"),
+  (22, "SIGTTOU"),
+  (23, "SIGIO"),
+  (24, "SIGXCPU"),
+  (25, "SIGXFSZ"),
+  (26, "SIGVTALRM"),
+  (27, "SIGPROF"),
+  (28, "SIGWINCH"),
+  (29, "SIGINFO"),
+  (30, "SIGUSR1"),
+  (31, "SIGUSR2")
+);
 
 #[cfg(any(target_os = "solaris", target_os = "illumos"))]
-pub fn signal_str_to_int(s: &str) -> Result<libc::c_int, AnyError> {
-  match s {
-    "SIGHUP" => Ok(1),
-    "SIGINT" => Ok(2),
-    "SIGQUIT" => Ok(3),
-    "SIGILL" => Ok(4),
-    "SIGTRAP" => Ok(5),
-    "SIGIOT" => Ok(6),
-    "SIGABRT" => Ok(6),
-    "SIGEMT" => Ok(7),
-    "SIGFPE" => Ok(8),
-    "SIGKILL" => Ok(9),
-    "SIGBUS" => Ok(10),
-    "SIGSEGV" => Ok(11),
-    "SIGSYS" => Ok(12),
-    "SIGPIPE" => Ok(13),
-    "SIGALRM" => Ok(14),
-    "SIGTERM" => Ok(15),
-    "SIGUSR1" => Ok(16),
-    "SIGUSR2" => Ok(17),
-    "SIGCLD" => Ok(18),
-    "SIGCHLD" => Ok(18),
-    "SIGPWR" => Ok(19),
-    "SIGWINCH" => Ok(20),
-    "SIGURG" => Ok(21),
-    "SIGPOLL" => Ok(22),
-    "SIGIO" => Ok(22),
-    "SIGSTOP" => Ok(23),
-    "SIGTSTP" => Ok(24),
-    "SIGCONT" => Ok(25),
-    "SIGTTIN" => Ok(26),
-    "SIGTTOU" => Ok(27),
-    "SIGVTALRM" => Ok(28),
-    "SIGPROF" => Ok(29),
-    "SIGXCPU" => Ok(30),
-    "SIGXFSZ" => Ok(31),
-    "SIGWAITING" => Ok(32),
-    "SIGLWP" => Ok(33),
-    "SIGFREEZE" => Ok(34),
-    "SIGTHAW" => Ok(35),
-    "SIGCANCEL" => Ok(36),
-    "SIGLOST" => Ok(37),
-    "SIGXRES" => Ok(38),
-    "SIGJVM1" => Ok(39),
-    "SIGJVM2" => Ok(40),
-    _ => Err(type_error(format!("Invalid signal : {}", s))),
-  }
-}
-
-#[cfg(any(target_os = "solaris", target_os = "illumos"))]
-pub fn signal_int_to_str(s: libc::c_int) -> Result<&'static str, AnyError> {
-  match s {
-    1 => Ok("SIGHUP"),
-    2 => Ok("SIGINT"),
-    3 => Ok("SIGQUIT"),
-    4 => Ok("SIGILL"),
-    5 => Ok("SIGTRAP"),
-    6 => Ok("SIGABRT"),
-    7 => Ok("SIGEMT"),
-    8 => Ok("SIGFPE"),
-    9 => Ok("SIGKILL"),
-    10 => Ok("SIGBUS"),
-    11 => Ok("SIGSEGV"),
-    12 => Ok("SIGSYS"),
-    13 => Ok("SIGPIPE"),
-    14 => Ok("SIGALRM"),
-    15 => Ok("SIGTERM"),
-    16 => Ok("SIGUSR1"),
-    17 => Ok("SIGUSR2"),
-    18 => Ok("SIGCHLD"),
-    19 => Ok("SIGPWR"),
-    20 => Ok("SIGWINCH"),
-    21 => Ok("SIGURG"),
-    22 => Ok("SIGPOLL"),
-    23 => Ok("SIGSTOP"),
-    24 => Ok("SIGTSTP"),
-    25 => Ok("SIGCONT"),
-    26 => Ok("SIGTTIN"),
-    27 => Ok("SIGTTOU"),
-    28 => Ok("SIGVTALRM"),
-    29 => Ok("SIGPROF"),
-    30 => Ok("SIGXCPU"),
-    31 => Ok("SIGXFSZ"),
-    32 => Ok("SIGWAITING"),
-    33 => Ok("SIGLWP"),
-    34 => Ok("SIGFREEZE"),
-    35 => Ok("SIGTHAW"),
-    36 => Ok("SIGCANCEL"),
-    37 => Ok("SIGLOST"),
-    38 => Ok("SIGXRES"),
-    39 => Ok("SIGJVM1"),
-    40 => Ok("SIGJVM2"),
-    _ => Err(type_error(format!("Invalid signal : {}", s))),
-  }
-}
+signal_dict!(
+  (1, "SIGHUP"),
+  (2, "SIGINT"),
+  (3, "SIGQUIT"),
+  (4, "SIGILL"),
+  (5, "SIGTRAP"),
+  (6, "SIGABRT" | "SIGIOT"),
+  (7, "SIGEMT"),
+  (8, "SIGFPE"),
+  (9, "SIGKILL"),
+  (10, "SIGBUS"),
+  (11, "SIGSEGV"),
+  (12, "SIGSYS"),
+  (13, "SIGPIPE"),
+  (14, "SIGALRM"),
+  (15, "SIGTERM"),
+  (16, "SIGUSR1"),
+  (17, "SIGUSR2"),
+  (18, "SIGCHLD"),
+  (19, "SIGPWR"),
+  (20, "SIGWINCH"),
+  (21, "SIGURG"),
+  (22, "SIGPOLL"),
+  (23, "SIGSTOP"),
+  (24, "SIGTSTP"),
+  (25, "SIGCONT"),
+  (26, "SIGTTIN"),
+  (27, "SIGTTOU"),
+  (28, "SIGVTALRM"),
+  (29, "SIGPROF"),
+  (30, "SIGXCPU"),
+  (31, "SIGXFSZ"),
+  (32, "SIGWAITING"),
+  (33, "SIGLWP"),
+  (34, "SIGFREEZE"),
+  (35, "SIGTHAW"),
+  (36, "SIGCANCEL"),
+  (37, "SIGLOST"),
+  (38, "SIGXRES"),
+  (39, "SIGJVM1"),
+  (40, "SIGJVM2")
+);
 
 #[cfg(target_os = "windows")]
-pub fn signal_str_to_int(s: &str) -> Result<libc::c_int, AnyError> {
-  match s {
-    "SIGINT" => Ok(2),
-    "SIGBREAK" => Ok(21),
-    _ => Err(type_error(
-      "Windows only supports ctrl-c (SIGINT) and ctrl-break (SIGBREAK).",
-    )),
-  }
-}
-
-#[cfg(target_os = "windows")]
-pub fn signal_int_to_str(s: libc::c_int) -> Result<&'static str, AnyError> {
-  match s {
-    2 => Ok("SIGINT"),
-    21 => Ok("SIGBREAK"),
-    _ => Err(type_error(
-      "Windows only supports ctrl-c (SIGINT) and ctrl-break (SIGBREAK).",
-    )),
-  }
-}
+signal_dict!((2, "SIGINT"), (21, "SIGBREAK"));
 
 #[cfg(unix)]
 #[op2(fast)]
@@ -586,12 +399,10 @@ pub fn signal_int_to_str(s: libc::c_int) -> Result<&'static str, AnyError> {
 fn op_signal_bind(
   state: &mut OpState,
   #[string] sig: &str,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, SignalError> {
   let signo = signal_str_to_int(sig)?;
   if signal_hook_registry::FORBIDDEN.contains(&signo) {
-    return Err(type_error(format!(
-      "Binding to signal '{sig}' is not allowed",
-    )));
+    return Err(SignalError::SignalNotAllowed(sig.to_string()));
   }
 
   let signal = AsyncRefCell::new(signal(SignalKind::from_raw(signo))?);
@@ -625,7 +436,7 @@ fn op_signal_bind(
 fn op_signal_bind(
   state: &mut OpState,
   #[string] sig: &str,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, SignalError> {
   let signo = signal_str_to_int(sig)?;
   let resource = SignalStreamResource {
     signal: AsyncRefCell::new(match signo {
@@ -649,7 +460,7 @@ fn op_signal_bind(
 async fn op_signal_poll(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<bool, AnyError> {
+) -> Result<bool, deno_core::error::AnyError> {
   let resource = state
     .borrow_mut()
     .resource_table
@@ -668,7 +479,7 @@ async fn op_signal_poll(
 pub fn op_signal_unbind(
   state: &mut OpState,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
+) -> Result<(), deno_core::error::AnyError> {
   let resource = state.resource_table.take::<SignalStreamResource>(rid)?;
 
   #[cfg(unix)]
diff --git a/runtime/ops/tty.rs b/runtime/ops/tty.rs
index 5b49e3a248..7849185faa 100644
--- a/runtime/ops/tty.rs
+++ b/runtime/ops/tty.rs
@@ -2,7 +2,6 @@
 
 use std::io::Error;
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use rustyline::config::Configurer;
@@ -64,6 +63,19 @@ deno_core::extension!(
   },
 );
 
+#[derive(Debug, thiserror::Error)]
+pub enum TtyError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[cfg(unix)]
+  #[error(transparent)]
+  Nix(nix::Error),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
 // ref: <https://learn.microsoft.com/en-us/windows/console/setconsolemode>
 #[cfg(windows)]
 const COOKED_MODE: DWORD =
@@ -90,8 +102,11 @@ fn op_set_raw(
   rid: u32,
   is_raw: bool,
   cbreak: bool,
-) -> Result<(), AnyError> {
-  let handle_or_fd = state.resource_table.get_fd(rid)?;
+) -> Result<(), TtyError> {
+  let handle_or_fd = state
+    .resource_table
+    .get_fd(rid)
+    .map_err(TtyError::Resource)?;
 
   // From https://github.com/kkawakam/rustyline/blob/master/src/tty/windows.rs
   // and https://github.com/kkawakam/rustyline/blob/master/src/tty/unix.rs
@@ -107,7 +122,7 @@ fn op_set_raw(
     let handle = handle_or_fd;
 
     if cbreak {
-      return Err(deno_core::error::not_supported());
+      return Err(TtyError::Other(deno_core::error::not_supported()));
     }
 
     let mut original_mode: DWORD = 0;
@@ -115,7 +130,7 @@ fn op_set_raw(
     if unsafe { consoleapi::GetConsoleMode(handle, &mut original_mode) }
       == FALSE
     {
-      return Err(Error::last_os_error().into());
+      return Err(TtyError::Io(Error::last_os_error()));
     }
 
     let new_mode = if is_raw {
@@ -185,7 +200,7 @@ fn op_set_raw(
           winapi::um::wincon::WriteConsoleInputW(handle, &record, 1, &mut 0)
         } == FALSE
         {
-          return Err(Error::last_os_error().into());
+          return Err(TtyError::Io(Error::last_os_error()));
         }
 
         /* Wait for read thread to acknowledge the cancellation to ensure that nothing
@@ -199,7 +214,7 @@ fn op_set_raw(
 
     // SAFETY: winapi call
     if unsafe { consoleapi::SetConsoleMode(handle, new_mode) } == FALSE {
-      return Err(Error::last_os_error().into());
+      return Err(TtyError::Io(Error::last_os_error()));
     }
 
     Ok(())
@@ -244,14 +259,16 @@ fn op_set_raw(
     let tty_mode_store = state.borrow::<TtyModeStore>().clone();
     let previous_mode = tty_mode_store.get(rid);
 
-    let raw_fd = handle_or_fd;
+    // SAFETY: Nix crate requires value to implement the AsFd trait
+    let raw_fd = unsafe { std::os::fd::BorrowedFd::borrow_raw(handle_or_fd) };
 
     if is_raw {
       let mut raw = match previous_mode {
         Some(mode) => mode,
         None => {
           // Save original mode.
-          let original_mode = termios::tcgetattr(raw_fd)?;
+          let original_mode =
+            termios::tcgetattr(raw_fd).map_err(TtyError::Nix)?;
           tty_mode_store.set(rid, original_mode.clone());
           original_mode
         }
@@ -273,11 +290,13 @@ fn op_set_raw(
       }
       raw.control_chars[termios::SpecialCharacterIndices::VMIN as usize] = 1;
       raw.control_chars[termios::SpecialCharacterIndices::VTIME as usize] = 0;
-      termios::tcsetattr(raw_fd, termios::SetArg::TCSADRAIN, &raw)?;
+      termios::tcsetattr(raw_fd, termios::SetArg::TCSADRAIN, &raw)
+        .map_err(TtyError::Nix)?;
     } else {
       // Try restore saved mode.
       if let Some(mode) = tty_mode_store.take(rid) {
-        termios::tcsetattr(raw_fd, termios::SetArg::TCSADRAIN, &mode)?;
+        termios::tcsetattr(raw_fd, termios::SetArg::TCSADRAIN, &mode)
+          .map_err(TtyError::Nix)?;
       }
     }
 
@@ -289,13 +308,16 @@ fn op_set_raw(
 fn op_console_size(
   state: &mut OpState,
   #[buffer] result: &mut [u32],
-) -> Result<(), AnyError> {
+) -> Result<(), TtyError> {
   fn check_console_size(
     state: &mut OpState,
     result: &mut [u32],
     rid: u32,
-  ) -> Result<(), AnyError> {
-    let fd = state.resource_table.get_fd(rid)?;
+  ) -> Result<(), TtyError> {
+    let fd = state
+      .resource_table
+      .get_fd(rid)
+      .map_err(TtyError::Resource)?;
     let size = console_size_from_fd(fd)?;
     result[0] = size.cols;
     result[1] = size.rows;
@@ -418,7 +440,7 @@ mod tests {
 pub fn op_read_line_prompt(
   #[string] prompt_text: &str,
   #[string] default_value: &str,
-) -> Result<Option<String>, AnyError> {
+) -> Result<Option<String>, ReadlineError> {
   let mut editor = Editor::<(), rustyline::history::DefaultHistory>::new()
     .expect("Failed to create editor.");
 
@@ -438,6 +460,6 @@ pub fn op_read_line_prompt(
       Ok(None)
     }
     Err(ReadlineError::Eof) => Ok(None),
-    Err(err) => Err(err.into()),
+    Err(err) => Err(err),
   }
 }
diff --git a/runtime/ops/utils.rs b/runtime/ops/utils.rs
deleted file mode 100644
index d5ce61c1fa..0000000000
--- a/runtime/ops/utils.rs
+++ /dev/null
@@ -1,12 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
-
-/// A utility function to map OsStrings to Strings
-pub fn into_string(s: std::ffi::OsString) -> Result<String, AnyError> {
-  s.into_string().map_err(|s| {
-    let message = format!("File name or path {s:?} is not valid UTF-8");
-    custom_error("InvalidData", message)
-  })
-}
diff --git a/runtime/ops/web_worker.rs b/runtime/ops/web_worker.rs
index 0ed76ebd50..d0c3eea668 100644
--- a/runtime/ops/web_worker.rs
+++ b/runtime/ops/web_worker.rs
@@ -4,15 +4,16 @@ mod sync_fetch;
 
 use crate::web_worker::WebWorkerInternalHandle;
 use crate::web_worker::WebWorkerType;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::CancelFuture;
 use deno_core::OpState;
 use deno_web::JsMessageData;
+use deno_web::MessagePortError;
 use std::cell::RefCell;
 use std::rc::Rc;
 
 use self::sync_fetch::op_worker_sync_fetch;
+pub use sync_fetch::SyncFetchError;
 
 deno_core::extension!(
   deno_web_worker,
@@ -30,17 +31,16 @@ deno_core::extension!(
 fn op_worker_post_message(
   state: &mut OpState,
   #[serde] data: JsMessageData,
-) -> Result<(), AnyError> {
+) -> Result<(), MessagePortError> {
   let handle = state.borrow::<WebWorkerInternalHandle>().clone();
-  handle.port.send(state, data)?;
-  Ok(())
+  handle.port.send(state, data)
 }
 
 #[op2(async(lazy), fast)]
 #[serde]
 async fn op_worker_recv_message(
   state: Rc<RefCell<OpState>>,
-) -> Result<Option<JsMessageData>, AnyError> {
+) -> Result<Option<JsMessageData>, MessagePortError> {
   let handle = {
     let state = state.borrow();
     state.borrow::<WebWorkerInternalHandle>().clone()
diff --git a/runtime/ops/web_worker/sync_fetch.rs b/runtime/ops/web_worker/sync_fetch.rs
index cdb151a86f..d1f133d3d2 100644
--- a/runtime/ops/web_worker/sync_fetch.rs
+++ b/runtime/ops/web_worker/sync_fetch.rs
@@ -4,15 +4,13 @@ use std::sync::Arc;
 
 use crate::web_worker::WebWorkerInternalHandle;
 use crate::web_worker::WebWorkerType;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::futures::StreamExt;
 use deno_core::op2;
 use deno_core::url::Url;
 use deno_core::OpState;
 use deno_fetch::data_url::DataUrl;
+use deno_fetch::FetchError;
 use deno_web::BlobStore;
-use deno_websocket::DomExceptionNetworkError;
 use http_body_util::BodyExt;
 use hyper::body::Bytes;
 use serde::Deserialize;
@@ -27,6 +25,32 @@ fn mime_type_essence(mime_type: &str) -> String {
   essence.trim().to_ascii_lowercase()
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum SyncFetchError {
+  #[error("Blob URLs are not supported in this context.")]
+  BlobUrlsNotSupportedInContext,
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[error("Invalid script URL")]
+  InvalidScriptUrl,
+  #[error("http status error: {0}")]
+  InvalidStatusCode(http::StatusCode),
+  #[error("Classic scripts with scheme {0}: are not supported in workers")]
+  ClassicScriptSchemeUnsupportedInWorkers(String),
+  #[error("{0}")]
+  InvalidUri(#[from] http::uri::InvalidUri),
+  #[error("Invalid MIME type {0:?}.")]
+  InvalidMimeType(String),
+  #[error("Missing MIME type.")]
+  MissingMimeType,
+  #[error(transparent)]
+  Fetch(#[from] FetchError),
+  #[error(transparent)]
+  Join(#[from] tokio::task::JoinError),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
 #[derive(Serialize, Deserialize)]
 #[serde(rename_all = "camelCase")]
 pub struct SyncFetchScript {
@@ -40,21 +64,22 @@ pub fn op_worker_sync_fetch(
   state: &mut OpState,
   #[serde] scripts: Vec<String>,
   loose_mime_checks: bool,
-) -> Result<Vec<SyncFetchScript>, AnyError> {
+) -> Result<Vec<SyncFetchScript>, SyncFetchError> {
   let handle = state.borrow::<WebWorkerInternalHandle>().clone();
   assert_eq!(handle.worker_type, WebWorkerType::Classic);
 
   // it's not safe to share a client across tokio runtimes, so create a fresh one
   // https://github.com/seanmonstar/reqwest/issues/1148#issuecomment-910868788
   let options = state.borrow::<deno_fetch::Options>().clone();
-  let client = deno_fetch::create_client_from_options(&options)?;
+  let client = deno_fetch::create_client_from_options(&options)
+    .map_err(FetchError::ClientCreate)?;
 
   // TODO(andreubotella) It's not good to throw an exception related to blob
   // URLs when none of the script URLs use the blob scheme.
   // Also, in which contexts are blob URLs not supported?
   let blob_store = state
     .try_borrow::<Arc<BlobStore>>()
-    .ok_or_else(|| type_error("Blob URLs are not supported in this context."))?
+    .ok_or(SyncFetchError::BlobUrlsNotSupportedInContext)?
     .clone();
 
   // TODO(andreubotella): make the below thread into a resource that can be
@@ -74,7 +99,7 @@ pub fn op_worker_sync_fetch(
           let blob_store = blob_store.clone();
           deno_core::unsync::spawn(async move {
             let script_url = Url::parse(&script)
-              .map_err(|_| type_error("Invalid script URL"))?;
+              .map_err(|_| SyncFetchError::InvalidScriptUrl)?;
             let mut loose_mime_checks = loose_mime_checks;
 
             let (body, mime_type, res_url) = match script_url.scheme() {
@@ -86,15 +111,13 @@ pub fn op_worker_sync_fetch(
                 );
                 *req.uri_mut() = script_url.as_str().parse()?;
 
-                let resp = client.send(req).await?;
+                let resp =
+                  client.send(req).await.map_err(FetchError::ClientSend)?;
 
                 if resp.status().is_client_error()
                   || resp.status().is_server_error()
                 {
-                  return Err(type_error(format!(
-                    "http status error: {}",
-                    resp.status()
-                  )));
+                  return Err(SyncFetchError::InvalidStatusCode(resp.status()));
                 }
 
                 // TODO(andreubotella) Properly run fetch's "extract a MIME type".
@@ -107,42 +130,45 @@ pub fn op_worker_sync_fetch(
                 // Always check the MIME type with HTTP(S).
                 loose_mime_checks = false;
 
-                let body = resp.collect().await?.to_bytes();
+                let body = resp
+                  .collect()
+                  .await
+                  .map_err(SyncFetchError::Other)?
+                  .to_bytes();
 
                 (body, mime_type, script)
               }
               "data" => {
-                let data_url = DataUrl::process(&script)
-                  .map_err(|e| type_error(format!("{e:?}")))?;
+                let data_url =
+                  DataUrl::process(&script).map_err(FetchError::DataUrl)?;
 
                 let mime_type = {
                   let mime = data_url.mime_type();
                   format!("{}/{}", mime.type_, mime.subtype)
                 };
 
-                let (body, _) = data_url
-                  .decode_to_vec()
-                  .map_err(|e| type_error(format!("{e:?}")))?;
+                let (body, _) =
+                  data_url.decode_to_vec().map_err(FetchError::Base64)?;
 
                 (Bytes::from(body), Some(mime_type), script)
               }
               "blob" => {
-                let blob =
-                  blob_store.get_object_url(script_url).ok_or_else(|| {
-                    type_error("Blob for the given URL not found.")
-                  })?;
+                let blob = blob_store
+                  .get_object_url(script_url)
+                  .ok_or(FetchError::BlobNotFound)?;
 
                 let mime_type = mime_type_essence(&blob.media_type);
 
-                let body = blob.read_all().await?;
+                let body = blob.read_all().await;
 
                 (Bytes::from(body), Some(mime_type), script)
               }
               _ => {
-                return Err(type_error(format!(
-              "Classic scripts with scheme {}: are not supported in workers.",
-              script_url.scheme()
-            )))
+                return Err(
+                  SyncFetchError::ClassicScriptSchemeUnsupportedInWorkers(
+                    script_url.scheme().to_string(),
+                  ),
+                )
               }
             };
 
@@ -151,18 +177,11 @@ pub fn op_worker_sync_fetch(
               match mime_type.as_deref() {
                 Some("application/javascript" | "text/javascript") => {}
                 Some(mime_type) => {
-                  return Err(
-                    DomExceptionNetworkError {
-                      msg: format!("Invalid MIME type {mime_type:?}."),
-                    }
-                    .into(),
-                  )
-                }
-                None => {
-                  return Err(
-                    DomExceptionNetworkError::new("Missing MIME type.").into(),
-                  )
+                  return Err(SyncFetchError::InvalidMimeType(
+                    mime_type.to_string(),
+                  ))
                 }
+                None => return Err(SyncFetchError::MissingMimeType),
               }
             }
 
diff --git a/runtime/ops/worker_host.rs b/runtime/ops/worker_host.rs
index 3c00356455..521284a6a0 100644
--- a/runtime/ops/worker_host.rs
+++ b/runtime/ops/worker_host.rs
@@ -10,19 +10,17 @@ use crate::web_worker::WorkerControlEvent;
 use crate::web_worker::WorkerId;
 use crate::web_worker::WorkerMetadata;
 use crate::worker::FormatJsErrorFn;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::serde::Deserialize;
 use deno_core::CancelFuture;
 use deno_core::CancelHandle;
 use deno_core::ModuleSpecifier;
 use deno_core::OpState;
-use deno_permissions::create_child_permissions;
 use deno_permissions::ChildPermissionsArg;
-use deno_permissions::PermissionDescriptorParser;
 use deno_permissions::PermissionsContainer;
 use deno_web::deserialize_js_transferables;
 use deno_web::JsMessageData;
+use deno_web::MessagePortError;
 use log::debug;
 use std::cell::RefCell;
 use std::collections::HashMap;
@@ -120,6 +118,20 @@ pub struct CreateWorkerArgs {
   close_on_idle: bool,
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum CreateWorkerError {
+  #[error("Classic workers are not supported.")]
+  ClassicWorkers,
+  #[error(transparent)]
+  Permission(deno_permissions::ChildPermissionError),
+  #[error(transparent)]
+  ModuleResolution(#[from] deno_core::ModuleResolutionError),
+  #[error(transparent)]
+  MessagePort(#[from] MessagePortError),
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+}
+
 /// Create worker as the host
 #[op2]
 #[serde]
@@ -127,7 +139,7 @@ fn op_create_worker(
   state: &mut OpState,
   #[serde] args: CreateWorkerArgs,
   #[serde] maybe_worker_metadata: Option<JsMessageData>,
-) -> Result<WorkerId, AnyError> {
+) -> Result<WorkerId, CreateWorkerError> {
   let specifier = args.specifier.clone();
   let maybe_source_code = if args.has_source_code {
     Some(args.source_code.clone())
@@ -138,12 +150,7 @@ fn op_create_worker(
   let worker_type = args.worker_type;
   if let WebWorkerType::Classic = worker_type {
     if let TestingFeaturesEnabled(false) = state.borrow() {
-      return Err(
-        deno_webstorage::DomExceptionNotSupportedError::new(
-          "Classic workers are not supported.",
-        )
-        .into(),
-      );
+      return Err(CreateWorkerError::ClassicWorkers);
     }
   }
 
@@ -154,19 +161,12 @@ fn op_create_worker(
       "Worker.deno.permissions",
     );
   }
-  let permission_desc_parser = state
-    .borrow::<Arc<dyn PermissionDescriptorParser>>()
-    .clone();
   let parent_permissions = state.borrow_mut::<PermissionsContainer>();
   let worker_permissions = if let Some(child_permissions_arg) = args.permissions
   {
-    let mut parent_permissions = parent_permissions.inner.lock();
-    let perms = create_child_permissions(
-      permission_desc_parser.as_ref(),
-      &mut parent_permissions,
-      child_permissions_arg,
-    )?;
-    PermissionsContainer::new(permission_desc_parser, perms)
+    parent_permissions
+      .create_child_permissions(child_permissions_arg)
+      .map_err(CreateWorkerError::Permission)?
   } else {
     parent_permissions.clone()
   };
@@ -178,9 +178,8 @@ fn op_create_worker(
   let module_specifier = deno_core::resolve_url(&specifier)?;
   let worker_name = args_name.unwrap_or_default();
 
-  let (handle_sender, handle_receiver) = std::sync::mpsc::sync_channel::<
-    Result<SendableWebWorkerHandle, AnyError>,
-  >(1);
+  let (handle_sender, handle_receiver) =
+    std::sync::mpsc::sync_channel::<SendableWebWorkerHandle>(1);
 
   // Setup new thread
   let thread_builder = std::thread::Builder::new().name(format!("{worker_id}"));
@@ -214,7 +213,7 @@ fn op_create_worker(
       });
 
     // Send thread safe handle from newly created worker to host thread
-    handle_sender.send(Ok(external_handle)).unwrap();
+    handle_sender.send(external_handle).unwrap();
     drop(handle_sender);
 
     // At this point the only method of communication with host
@@ -230,7 +229,7 @@ fn op_create_worker(
   })?;
 
   // Receive WebWorkerHandle from newly created worker
-  let worker_handle = handle_receiver.recv().unwrap()?;
+  let worker_handle = handle_receiver.recv().unwrap();
 
   let worker_thread = WorkerThread {
     worker_handle: worker_handle.into(),
@@ -303,7 +302,7 @@ fn close_channel(
 async fn op_host_recv_ctrl(
   state: Rc<RefCell<OpState>>,
   #[serde] id: WorkerId,
-) -> Result<WorkerControlEvent, AnyError> {
+) -> WorkerControlEvent {
   let (worker_handle, cancel_handle) = {
     let state = state.borrow();
     let workers_table = state.borrow::<WorkersTable>();
@@ -312,7 +311,7 @@ async fn op_host_recv_ctrl(
       (handle.worker_handle.clone(), handle.cancel_handle.clone())
     } else {
       // If handle was not found it means worker has already shutdown
-      return Ok(WorkerControlEvent::Close);
+      return WorkerControlEvent::Close;
     }
   };
 
@@ -321,22 +320,21 @@ async fn op_host_recv_ctrl(
     .or_cancel(cancel_handle)
     .await;
   match maybe_event {
-    Ok(Ok(Some(event))) => {
+    Ok(Some(event)) => {
       // Terminal error means that worker should be removed from worker table.
       if let WorkerControlEvent::TerminalError(_) = &event {
         close_channel(state, id, WorkerChannel::Ctrl);
       }
-      Ok(event)
+      event
     }
-    Ok(Ok(None)) => {
+    Ok(None) => {
       // If there was no event from worker it means it has already been closed.
       close_channel(state, id, WorkerChannel::Ctrl);
-      Ok(WorkerControlEvent::Close)
+      WorkerControlEvent::Close
     }
-    Ok(Err(err)) => Err(err),
     Err(_) => {
       // The worker was terminated.
-      Ok(WorkerControlEvent::Close)
+      WorkerControlEvent::Close
     }
   }
 }
@@ -346,7 +344,7 @@ async fn op_host_recv_ctrl(
 async fn op_host_recv_message(
   state: Rc<RefCell<OpState>>,
   #[serde] id: WorkerId,
-) -> Result<Option<JsMessageData>, AnyError> {
+) -> Result<Option<JsMessageData>, MessagePortError> {
   let (worker_handle, cancel_handle) = {
     let s = state.borrow();
     let workers_table = s.borrow::<WorkersTable>();
@@ -385,7 +383,7 @@ fn op_host_post_message(
   state: &mut OpState,
   #[serde] id: WorkerId,
   #[serde] data: JsMessageData,
-) -> Result<(), AnyError> {
+) -> Result<(), MessagePortError> {
   if let Some(worker_thread) = state.borrow::<WorkersTable>().get(&id) {
     debug!("post message to worker {}", id);
     let worker_handle = worker_thread.worker_handle.clone();
diff --git a/runtime/permissions.rs b/runtime/permissions.rs
index 9b2737b4fc..e8460e03f8 100644
--- a/runtime/permissions.rs
+++ b/runtime/permissions.rs
@@ -3,10 +3,7 @@
 use std::path::Path;
 use std::path::PathBuf;
 
-use deno_core::anyhow::bail;
-use deno_core::anyhow::Context;
-use deno_core::error::AnyError;
-use deno_core::normalize_path;
+use deno_path_util::normalize_path;
 use deno_permissions::AllowRunDescriptor;
 use deno_permissions::AllowRunDescriptorParseResult;
 use deno_permissions::DenyRunDescriptor;
@@ -15,9 +12,12 @@ use deno_permissions::FfiDescriptor;
 use deno_permissions::ImportDescriptor;
 use deno_permissions::NetDescriptor;
 use deno_permissions::PathQueryDescriptor;
+use deno_permissions::PathResolveError;
 use deno_permissions::ReadDescriptor;
+use deno_permissions::RunDescriptorParseError;
 use deno_permissions::RunQueryDescriptor;
 use deno_permissions::SysDescriptor;
+use deno_permissions::SysDescriptorParseError;
 use deno_permissions::WriteDescriptor;
 
 #[derive(Debug)]
@@ -30,9 +30,9 @@ impl RuntimePermissionDescriptorParser {
     Self { fs }
   }
 
-  fn resolve_from_cwd(&self, path: &str) -> Result<PathBuf, AnyError> {
+  fn resolve_from_cwd(&self, path: &str) -> Result<PathBuf, PathResolveError> {
     if path.is_empty() {
-      bail!("Empty path is not allowed");
+      return Err(PathResolveError::EmptyPath);
     }
     let path = Path::new(path);
     if path.is_absolute() {
@@ -43,12 +43,11 @@ impl RuntimePermissionDescriptorParser {
     }
   }
 
-  fn resolve_cwd(&self) -> Result<PathBuf, AnyError> {
+  fn resolve_cwd(&self) -> Result<PathBuf, PathResolveError> {
     self
       .fs
       .cwd()
-      .map_err(|e| e.into_io_error())
-      .context("failed resolving cwd")
+      .map_err(|e| PathResolveError::CwdResolve(e.into_io_error()))
   }
 }
 
@@ -58,37 +57,37 @@ impl deno_permissions::PermissionDescriptorParser
   fn parse_read_descriptor(
     &self,
     text: &str,
-  ) -> Result<ReadDescriptor, AnyError> {
+  ) -> Result<ReadDescriptor, PathResolveError> {
     Ok(ReadDescriptor(self.resolve_from_cwd(text)?))
   }
 
   fn parse_write_descriptor(
     &self,
     text: &str,
-  ) -> Result<WriteDescriptor, AnyError> {
+  ) -> Result<WriteDescriptor, PathResolveError> {
     Ok(WriteDescriptor(self.resolve_from_cwd(text)?))
   }
 
   fn parse_net_descriptor(
     &self,
     text: &str,
-  ) -> Result<NetDescriptor, AnyError> {
+  ) -> Result<NetDescriptor, deno_permissions::NetDescriptorParseError> {
     NetDescriptor::parse(text)
   }
 
   fn parse_import_descriptor(
     &self,
     text: &str,
-  ) -> Result<ImportDescriptor, AnyError> {
+  ) -> Result<ImportDescriptor, deno_permissions::NetDescriptorParseError> {
     ImportDescriptor::parse(text)
   }
 
   fn parse_env_descriptor(
     &self,
     text: &str,
-  ) -> Result<EnvDescriptor, AnyError> {
+  ) -> Result<EnvDescriptor, deno_permissions::EnvDescriptorParseError> {
     if text.is_empty() {
-      Err(AnyError::msg("Empty env not allowed"))
+      Err(deno_permissions::EnvDescriptorParseError)
     } else {
       Ok(EnvDescriptor::new(text))
     }
@@ -97,32 +96,32 @@ impl deno_permissions::PermissionDescriptorParser
   fn parse_sys_descriptor(
     &self,
     text: &str,
-  ) -> Result<deno_permissions::SysDescriptor, AnyError> {
+  ) -> Result<SysDescriptor, SysDescriptorParseError> {
     if text.is_empty() {
-      Err(AnyError::msg("Empty sys not allowed"))
+      Err(SysDescriptorParseError::Empty)
     } else {
-      Ok(SysDescriptor(text.to_string()))
+      Ok(SysDescriptor::parse(text.to_string())?)
     }
   }
 
   fn parse_allow_run_descriptor(
     &self,
     text: &str,
-  ) -> Result<AllowRunDescriptorParseResult, AnyError> {
+  ) -> Result<AllowRunDescriptorParseResult, RunDescriptorParseError> {
     Ok(AllowRunDescriptor::parse(text, &self.resolve_cwd()?)?)
   }
 
   fn parse_deny_run_descriptor(
     &self,
     text: &str,
-  ) -> Result<DenyRunDescriptor, AnyError> {
+  ) -> Result<DenyRunDescriptor, PathResolveError> {
     Ok(DenyRunDescriptor::parse(text, &self.resolve_cwd()?))
   }
 
   fn parse_ffi_descriptor(
     &self,
     text: &str,
-  ) -> Result<deno_permissions::FfiDescriptor, AnyError> {
+  ) -> Result<FfiDescriptor, PathResolveError> {
     Ok(FfiDescriptor(self.resolve_from_cwd(text)?))
   }
 
@@ -131,7 +130,7 @@ impl deno_permissions::PermissionDescriptorParser
   fn parse_path_query(
     &self,
     path: &str,
-  ) -> Result<PathQueryDescriptor, AnyError> {
+  ) -> Result<PathQueryDescriptor, PathResolveError> {
     Ok(PathQueryDescriptor {
       resolved: self.resolve_from_cwd(path)?,
       requested: path.to_string(),
@@ -141,11 +140,12 @@ impl deno_permissions::PermissionDescriptorParser
   fn parse_run_query(
     &self,
     requested: &str,
-  ) -> Result<RunQueryDescriptor, AnyError> {
+  ) -> Result<RunQueryDescriptor, RunDescriptorParseError> {
     if requested.is_empty() {
-      bail!("Empty run query is not allowed");
+      return Err(RunDescriptorParseError::EmptyRunQuery);
     }
     RunQueryDescriptor::parse(requested)
+      .map_err(RunDescriptorParseError::PathResolve)
   }
 }
 
diff --git a/runtime/permissions/Cargo.toml b/runtime/permissions/Cargo.toml
index 9821b61484..e088eb8ce5 100644
--- a/runtime/permissions/Cargo.toml
+++ b/runtime/permissions/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_permissions"
-version = "0.28.0"
+version = "0.37.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -15,6 +15,7 @@ path = "lib.rs"
 
 [dependencies]
 deno_core.workspace = true
+deno_path_util.workspace = true
 deno_terminal.workspace = true
 fqdn = "0.3.4"
 libc.workspace = true
@@ -22,6 +23,7 @@ log.workspace = true
 once_cell.workspace = true
 percent-encoding = { version = "2.3.1", features = [] }
 serde.workspace = true
+thiserror.workspace = true
 which.workspace = true
 
 [target.'cfg(windows)'.dependencies]
diff --git a/runtime/permissions/lib.rs b/runtime/permissions/lib.rs
index 5d8e76125e..71ef7d2289 100644
--- a/runtime/permissions/lib.rs
+++ b/runtime/permissions/lib.rs
@@ -1,12 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::anyhow::bail;
-use deno_core::anyhow::Context;
-use deno_core::error::custom_error;
-use deno_core::error::type_error;
-use deno_core::error::uri_error;
-use deno_core::error::AnyError;
-use deno_core::normalize_path;
 use deno_core::parking_lot::Mutex;
 use deno_core::serde::de;
 use deno_core::serde::Deserialize;
@@ -16,6 +9,8 @@ use deno_core::serde_json;
 use deno_core::unsync::sync::AtomicFlag;
 use deno_core::url::Url;
 use deno_core::ModuleSpecifier;
+use deno_path_util::normalize_path;
+use deno_path_util::url_to_file_path;
 use deno_terminal::colors;
 use fqdn::FQDN;
 use once_cell::sync::Lazy;
@@ -34,11 +29,28 @@ use std::sync::Arc;
 
 pub mod prompter;
 use prompter::permission_prompt;
-use prompter::PromptResponse;
 use prompter::PERMISSION_EMOJI;
 
 pub use prompter::set_prompt_callbacks;
+pub use prompter::set_prompter;
+pub use prompter::PermissionPrompter;
 pub use prompter::PromptCallback;
+pub use prompter::PromptResponse;
+
+#[derive(Debug, thiserror::Error)]
+#[error("Requires {access}, {}", format_permission_error(.name))]
+pub struct PermissionDeniedError {
+  pub access: String,
+  pub name: &'static str,
+}
+
+fn format_permission_error(name: &'static str) -> String {
+  if is_standalone() {
+    format!("specify the required permissions during compilation using `deno compile --allow-{name}`")
+  } else {
+    format!("run again with the --allow-{name} flag")
+  }
+}
 
 /// Fast exit from permission check routines if this permission
 /// is in the "fully-granted" state.
@@ -101,7 +113,10 @@ impl From<bool> for AllowPartial {
 
 impl PermissionState {
   #[inline(always)]
-  fn log_perm_access(name: &str, info: impl FnOnce() -> Option<String>) {
+  fn log_perm_access(
+    name: &'static str,
+    info: impl FnOnce() -> Option<String>,
+  ) {
     // Eliminates log overhead (when logging is disabled),
     // log_enabled!(Debug) check in a hot path still has overhead
     // TODO(AaronO): generalize or upstream this optimization
@@ -117,53 +132,47 @@ impl PermissionState {
     }
   }
 
-  fn fmt_access(name: &str, info: impl FnOnce() -> Option<String>) -> String {
+  fn fmt_access(
+    name: &'static str,
+    info: impl FnOnce() -> Option<String>,
+  ) -> String {
     format!(
       "{} access{}",
       name,
-      info()
-        .map(|info| { format!(" to {info}") })
-        .unwrap_or_default(),
+      info().map(|info| format!(" to {info}")).unwrap_or_default(),
     )
   }
 
-  fn error(name: &str, info: impl FnOnce() -> Option<String>) -> AnyError {
-    let msg = if is_standalone() {
-      format!(
-        "Requires {}, specify the required permissions during compilation using `deno compile --allow-{}`",
-        Self::fmt_access(name, info),
-        name
-      )
-    } else {
-      format!(
-        "Requires {}, run again with the --allow-{} flag",
-        Self::fmt_access(name, info),
-        name
-      )
-    };
-    custom_error("NotCapable", msg)
+  fn error(
+    name: &'static str,
+    info: impl FnOnce() -> Option<String>,
+  ) -> PermissionDeniedError {
+    PermissionDeniedError {
+      access: Self::fmt_access(name, info),
+      name,
+    }
   }
 
   /// Check the permission state. bool is whether a prompt was issued.
   #[inline]
   fn check(
     self,
-    name: &str,
+    name: &'static str,
     api_name: Option<&str>,
     info: Option<&str>,
     prompt: bool,
-  ) -> (Result<(), AnyError>, bool, bool) {
+  ) -> (Result<(), PermissionDeniedError>, bool, bool) {
     self.check2(name, api_name, || info.map(|s| s.to_string()), prompt)
   }
 
   #[inline]
   fn check2(
     self,
-    name: &str,
+    name: &'static str,
     api_name: Option<&str>,
     info: impl Fn() -> Option<String>,
     prompt: bool,
-  ) -> (Result<(), AnyError>, bool, bool) {
+  ) -> (Result<(), PermissionDeniedError>, bool, bool) {
     match self {
       PermissionState::Granted => {
         Self::log_perm_access(name, info);
@@ -243,7 +252,7 @@ impl UnitPermission {
     self.state
   }
 
-  pub fn check(&mut self) -> Result<(), AnyError> {
+  pub fn check(&mut self) -> Result<(), PermissionDeniedError> {
     let (result, prompted, _is_allow_all) =
       self.state.check(self.name, None, None, self.prompt);
     if prompted {
@@ -259,7 +268,7 @@ impl UnitPermission {
   fn create_child_permissions(
     &mut self,
     flag: ChildUnitPermissionArg,
-  ) -> Result<Self, AnyError> {
+  ) -> Result<Self, ChildPermissionError> {
     let mut perm = self.clone();
     match flag {
       ChildUnitPermissionArg::Inherit => {
@@ -267,7 +276,7 @@ impl UnitPermission {
       }
       ChildUnitPermissionArg::Granted => {
         if self.check().is_err() {
-          return Err(escalation_error());
+          return Err(ChildPermissionError::Escalation);
         }
         perm.state = PermissionState::Granted;
       }
@@ -324,7 +333,7 @@ pub trait QueryDescriptor: Debug {
     &self,
     perm: &mut UnaryPermission<Self>,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError>;
+  ) -> Result<(), PermissionDeniedError>;
 
   fn matches_allow(&self, other: &Self::AllowDesc) -> bool;
   fn matches_deny(&self, other: &Self::DenyDesc) -> bool;
@@ -399,7 +408,7 @@ impl<TQuery: QueryDescriptor> UnaryPermission<TQuery> {
   pub fn check_all_api(
     &mut self,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
     self.check_desc(None, false, api_name)
   }
@@ -409,7 +418,7 @@ impl<TQuery: QueryDescriptor> UnaryPermission<TQuery> {
     desc: Option<&TQuery>,
     assert_non_partial: bool,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     let (result, prompted, is_allow_all) = self
       .query_desc(desc, AllowPartial::from(!assert_non_partial))
       .check2(
@@ -475,6 +484,9 @@ impl<TQuery: QueryDescriptor> UnaryPermission<TQuery> {
     if state != PermissionState::Prompt {
       return state;
     }
+    if !self.prompt {
+      return PermissionState::Denied;
+    }
     let mut message = String::with_capacity(40);
     message.push_str(&format!("{} access", TQuery::flag_name()));
     if let Some(desc) = desc {
@@ -593,11 +605,14 @@ impl<TQuery: QueryDescriptor> UnaryPermission<TQuery> {
     }
   }
 
-  fn create_child_permissions(
+  fn create_child_permissions<E>(
     &mut self,
     flag: ChildUnaryPermissionArg,
-    parse: impl Fn(&str) -> Result<Option<TQuery::AllowDesc>, AnyError>,
-  ) -> Result<UnaryPermission<TQuery>, AnyError> {
+    parse: impl Fn(&str) -> Result<Option<TQuery::AllowDesc>, E>,
+  ) -> Result<UnaryPermission<TQuery>, ChildPermissionError>
+  where
+    ChildPermissionError: From<E>,
+  {
     let mut perms = Self::default();
 
     match flag {
@@ -606,7 +621,7 @@ impl<TQuery: QueryDescriptor> UnaryPermission<TQuery> {
       }
       ChildUnaryPermissionArg::Granted => {
         if self.check_all_api(None).is_err() {
-          return Err(escalation_error());
+          return Err(ChildPermissionError::Escalation);
         }
         perms.granted_global = true;
       }
@@ -615,13 +630,13 @@ impl<TQuery: QueryDescriptor> UnaryPermission<TQuery> {
         perms.granted_list = granted_list
           .iter()
           .filter_map(|i| parse(i).transpose())
-          .collect::<Result<_, _>>()?;
+          .collect::<Result<_, E>>()?;
         if !perms.granted_list.iter().all(|desc| {
           TQuery::from_allow(desc)
             .check_in_permission(self, None)
             .is_ok()
         }) {
-          return Err(escalation_error());
+          return Err(ChildPermissionError::Escalation);
         }
       }
     }
@@ -692,7 +707,7 @@ impl QueryDescriptor for ReadQueryDescriptor {
     &self,
     perm: &mut UnaryPermission<Self>,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(perm);
     perm.check_desc(Some(self), true, api_name)
   }
@@ -755,7 +770,7 @@ impl QueryDescriptor for WriteQueryDescriptor {
     &self,
     perm: &mut UnaryPermission<Self>,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(perm);
     perm.check_desc(Some(self), true, api_name)
   }
@@ -790,22 +805,37 @@ pub enum Host {
   Ip(IpAddr),
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum HostParseError {
+  #[error("invalid IPv6 address: '{0}'")]
+  InvalidIpv6(String),
+  #[error("invalid host: '{0}'")]
+  InvalidHost(String),
+  #[error("invalid empty host: '{0}'")]
+  InvalidEmptyHost(String),
+  #[error("invalid host '{host}': {error}")]
+  Fqdn {
+    #[source]
+    error: fqdn::Error,
+    host: String,
+  },
+}
+
 impl Host {
-  // TODO(bartlomieju): rewrite to not use `AnyError` but a specific error implementations
-  fn parse(s: &str) -> Result<Self, AnyError> {
+  fn parse(s: &str) -> Result<Self, HostParseError> {
     if s.starts_with('[') && s.ends_with(']') {
       let ip = s[1..s.len() - 1]
         .parse::<Ipv6Addr>()
-        .map_err(|_| uri_error(format!("invalid IPv6 address: '{s}'")))?;
+        .map_err(|_| HostParseError::InvalidIpv6(s.to_string()))?;
       return Ok(Host::Ip(IpAddr::V6(ip)));
     }
     let (without_trailing_dot, has_trailing_dot) =
       s.strip_suffix('.').map_or((s, false), |s| (s, true));
     if let Ok(ip) = without_trailing_dot.parse::<IpAddr>() {
       if has_trailing_dot {
-        return Err(uri_error(format!(
-          "invalid host: '{without_trailing_dot}'"
-        )));
+        return Err(HostParseError::InvalidHost(
+          without_trailing_dot.to_string(),
+        ));
       }
       Ok(Host::Ip(ip))
     } else {
@@ -816,11 +846,13 @@ impl Host {
       };
       let fqdn = {
         use std::str::FromStr;
-        FQDN::from_str(&lower)
-          .with_context(|| format!("invalid host: '{s}'"))?
+        FQDN::from_str(&lower).map_err(|e| HostParseError::Fqdn {
+          error: e,
+          host: s.to_string(),
+        })?
       };
       if fqdn.is_root() {
-        return Err(uri_error(format!("invalid empty host: '{s}'")));
+        return Err(HostParseError::InvalidEmptyHost(s.to_string()));
       }
       Ok(Host::Fqdn(fqdn))
     }
@@ -864,7 +896,7 @@ impl QueryDescriptor for NetDescriptor {
     &self,
     perm: &mut UnaryPermission<Self>,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(perm);
     perm.check_desc(Some(self), false, api_name)
   }
@@ -890,39 +922,72 @@ impl QueryDescriptor for NetDescriptor {
   }
 }
 
-// TODO(bartlomieju): rewrite to not use `AnyError` but a specific error implementations
+#[derive(Debug, thiserror::Error)]
+pub enum NetDescriptorParseError {
+  #[error("invalid value '{0}': URLs are not supported, only domains and ips")]
+  Url(String),
+  #[error("invalid IPv6 address in '{hostname}': '{ip}'")]
+  InvalidIpv6 { hostname: String, ip: String },
+  #[error("invalid port in '{hostname}': '{port}'")]
+  InvalidPort { hostname: String, port: String },
+  #[error("invalid host: '{0}'")]
+  InvalidHost(String),
+  #[error("invalid empty port in '{0}'")]
+  EmptyPort(String),
+  #[error("ipv6 addresses must be enclosed in square brackets: '{0}'")]
+  Ipv6MissingSquareBrackets(String),
+  #[error("{0}")]
+  Host(#[from] HostParseError),
+}
+
+#[derive(Debug, thiserror::Error)]
+pub enum NetDescriptorFromUrlParseError {
+  #[error("Missing host in url: '{0}'")]
+  MissingHost(Url),
+  #[error("{0}")]
+  Host(#[from] HostParseError),
+}
+
 impl NetDescriptor {
-  pub fn parse(hostname: &str) -> Result<Self, AnyError> {
+  pub fn parse(hostname: &str) -> Result<Self, NetDescriptorParseError> {
     if hostname.starts_with("http://") || hostname.starts_with("https://") {
-      return Err(uri_error(format!("invalid value '{hostname}': URLs are not supported, only domains and ips")));
+      return Err(NetDescriptorParseError::Url(hostname.to_string()));
     }
 
     // If this is a IPv6 address enclosed in square brackets, parse it as such.
     if hostname.starts_with('[') {
       if let Some((ip, after)) = hostname.split_once(']') {
         let ip = ip[1..].parse::<Ipv6Addr>().map_err(|_| {
-          uri_error(format!("invalid IPv6 address in '{hostname}': '{ip}'"))
+          NetDescriptorParseError::InvalidIpv6 {
+            hostname: hostname.to_string(),
+            ip: ip.to_string(),
+          }
         })?;
         let port = if let Some(port) = after.strip_prefix(':') {
           let port = port.parse::<u16>().map_err(|_| {
-            uri_error(format!("invalid port in '{hostname}': '{port}'"))
+            NetDescriptorParseError::InvalidPort {
+              hostname: hostname.to_string(),
+              port: port.to_string(),
+            }
           })?;
           Some(port)
         } else if after.is_empty() {
           None
         } else {
-          return Err(uri_error(format!("invalid host: '{hostname}'")));
+          return Err(NetDescriptorParseError::InvalidHost(
+            hostname.to_string(),
+          ));
         };
         return Ok(NetDescriptor(Host::Ip(IpAddr::V6(ip)), port));
       } else {
-        return Err(uri_error(format!("invalid host: '{hostname}'")));
+        return Err(NetDescriptorParseError::InvalidHost(hostname.to_string()));
       }
     }
 
     // Otherwise it is an IPv4 address or a FQDN with an optional port.
     let (host, port) = match hostname.split_once(':') {
       Some((_, "")) => {
-        return Err(uri_error(format!("invalid empty port in '{hostname}'")));
+        return Err(NetDescriptorParseError::EmptyPort(hostname.to_string()));
       }
       Some((host, port)) => (host, port),
       None => (hostname, ""),
@@ -937,11 +1002,14 @@ impl NetDescriptor {
         // should give them a hint. There are always at least two colons in an
         // IPv6 address, so this heuristic finds likely a bare IPv6 address.
         if port.contains(':') {
-          uri_error(format!(
-            "ipv6 addresses must be enclosed in square brackets: '{hostname}'"
-          ))
+          NetDescriptorParseError::Ipv6MissingSquareBrackets(
+            hostname.to_string(),
+          )
         } else {
-          uri_error(format!("invalid port in '{hostname}': '{port}'"))
+          NetDescriptorParseError::InvalidPort {
+            hostname: hostname.to_string(),
+            port: port.to_string(),
+          }
         }
       })?;
       Some(port)
@@ -950,10 +1018,10 @@ impl NetDescriptor {
     Ok(NetDescriptor(host, port))
   }
 
-  pub fn from_url(url: &Url) -> Result<Self, AnyError> {
-    let host = url
-      .host_str()
-      .ok_or_else(|| type_error(format!("Missing host in url: '{}'", url)))?;
+  pub fn from_url(url: &Url) -> Result<Self, NetDescriptorFromUrlParseError> {
+    let host = url.host_str().ok_or_else(|| {
+      NetDescriptorFromUrlParseError::MissingHost(url.clone())
+    })?;
     let host = Host::parse(host)?;
     let port = url.port_or_known_default();
     Ok(NetDescriptor(host, port))
@@ -1005,7 +1073,7 @@ impl QueryDescriptor for ImportDescriptor {
     &self,
     perm: &mut UnaryPermission<Self>,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(perm);
     perm.check_desc(Some(self), false, api_name)
   }
@@ -1032,15 +1100,19 @@ impl QueryDescriptor for ImportDescriptor {
 }
 
 impl ImportDescriptor {
-  pub fn parse(specifier: &str) -> Result<Self, AnyError> {
+  pub fn parse(specifier: &str) -> Result<Self, NetDescriptorParseError> {
     Ok(ImportDescriptor(NetDescriptor::parse(specifier)?))
   }
 
-  pub fn from_url(url: &Url) -> Result<Self, AnyError> {
+  pub fn from_url(url: &Url) -> Result<Self, NetDescriptorFromUrlParseError> {
     Ok(ImportDescriptor(NetDescriptor::from_url(url)?))
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+#[error("Empty env not allowed")]
+pub struct EnvDescriptorParseError;
+
 #[derive(Clone, Eq, PartialEq, Hash, Debug)]
 pub struct EnvDescriptor(EnvVarName);
 
@@ -1078,7 +1150,7 @@ impl QueryDescriptor for EnvDescriptor {
     &self,
     perm: &mut UnaryPermission<Self>,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(perm);
     perm.check_desc(Some(self), false, api_name)
   }
@@ -1125,14 +1197,25 @@ pub enum RunQueryDescriptor {
   Name(String),
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum PathResolveError {
+  #[error("failed resolving cwd: {0}")]
+  CwdResolve(#[source] std::io::Error),
+  #[error("Empty path is not allowed")]
+  EmptyPath,
+}
+
 impl RunQueryDescriptor {
-  pub fn parse(requested: &str) -> Result<RunQueryDescriptor, AnyError> {
+  pub fn parse(
+    requested: &str,
+  ) -> Result<RunQueryDescriptor, PathResolveError> {
     if is_path(requested) {
       let path = PathBuf::from(requested);
       let resolved = if path.is_absolute() {
         normalize_path(path)
       } else {
-        let cwd = std::env::current_dir().context("failed resolving cwd")?;
+        let cwd =
+          std::env::current_dir().map_err(PathResolveError::CwdResolve)?;
         normalize_path(cwd.join(path))
       };
       Ok(RunQueryDescriptor::Path {
@@ -1204,7 +1287,7 @@ impl QueryDescriptor for RunQueryDescriptor {
     &self,
     perm: &mut UnaryPermission<Self>,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(perm);
     perm.check_desc(Some(self), false, api_name)
   }
@@ -1274,6 +1357,16 @@ pub enum AllowRunDescriptorParseResult {
   Descriptor(AllowRunDescriptor),
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum RunDescriptorParseError {
+  #[error("{0}")]
+  Which(#[from] which::Error),
+  #[error("{0}")]
+  PathResolve(#[from] PathResolveError),
+  #[error("Empty run query is not allowed")]
+  EmptyRunQuery,
+}
+
 #[derive(Debug, Clone, Hash, Eq, PartialEq)]
 pub struct AllowRunDescriptor(pub PathBuf);
 
@@ -1354,8 +1447,36 @@ fn denies_run_name(name: &str, cmd_path: &Path) -> bool {
   suffix.is_empty() || suffix.starts_with('.')
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum SysDescriptorParseError {
+  #[error("unknown system info kind \"{0}\"")]
+  InvalidKind(String), // TypeError
+  #[error("Empty sys not allowed")]
+  Empty, // Error
+}
+
 #[derive(Clone, Eq, PartialEq, Hash, Debug)]
-pub struct SysDescriptor(pub String);
+pub struct SysDescriptor(String);
+
+impl SysDescriptor {
+  pub fn parse(kind: String) -> Result<Self, SysDescriptorParseError> {
+    match kind.as_str() {
+      "hostname" | "inspector" | "osRelease" | "osUptime" | "loadavg"
+      | "networkInterfaces" | "systemMemoryInfo" | "uid" | "gid" | "cpus"
+      | "homedir" | "getegid" | "statfs" | "getPriority" | "setPriority"
+      | "userInfo" => Ok(Self(kind)),
+
+      // the underlying permission check changed to `userInfo` to better match the API,
+      // alias this to avoid breaking existing projects with `--allow-sys=username`
+      "username" => Ok(Self("userInfo".into())),
+      _ => Err(SysDescriptorParseError::InvalidKind(kind)),
+    }
+  }
+
+  pub fn into_string(self) -> String {
+    self.0
+  }
+}
 
 impl QueryDescriptor for SysDescriptor {
   type AllowDesc = SysDescriptor;
@@ -1385,7 +1506,7 @@ impl QueryDescriptor for SysDescriptor {
     &self,
     perm: &mut UnaryPermission<Self>,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(perm);
     perm.check_desc(Some(self), false, api_name)
   }
@@ -1411,15 +1532,6 @@ impl QueryDescriptor for SysDescriptor {
   }
 }
 
-pub fn parse_sys_kind(kind: &str) -> Result<&str, AnyError> {
-  match kind {
-    "hostname" | "osRelease" | "osUptime" | "loadavg" | "networkInterfaces"
-    | "systemMemoryInfo" | "uid" | "gid" | "cpus" | "homedir" | "getegid"
-    | "username" | "statfs" | "getPriority" | "setPriority" => Ok(kind),
-    _ => Err(type_error(format!("unknown system info kind \"{kind}\""))),
-  }
-}
-
 #[derive(Clone, Eq, PartialEq, Hash, Debug)]
 pub struct FfiQueryDescriptor(pub PathQueryDescriptor);
 
@@ -1455,7 +1567,7 @@ impl QueryDescriptor for FfiQueryDescriptor {
     &self,
     perm: &mut UnaryPermission<Self>,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(perm);
     perm.check_desc(Some(self), true, api_name)
   }
@@ -1507,7 +1619,7 @@ impl UnaryPermission<ReadQueryDescriptor> {
     &mut self,
     desc: &ReadQueryDescriptor,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
     self.check_desc(Some(desc), true, api_name)
   }
@@ -1517,12 +1629,15 @@ impl UnaryPermission<ReadQueryDescriptor> {
     &mut self,
     desc: &ReadQueryDescriptor,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
     self.check_desc(Some(desc), false, api_name)
   }
 
-  pub fn check_all(&mut self, api_name: Option<&str>) -> Result<(), AnyError> {
+  pub fn check_all(
+    &mut self,
+    api_name: Option<&str>,
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
     self.check_desc(None, false, api_name)
   }
@@ -1551,7 +1666,7 @@ impl UnaryPermission<WriteQueryDescriptor> {
     &mut self,
     path: &WriteQueryDescriptor,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
     self.check_desc(Some(path), true, api_name)
   }
@@ -1561,12 +1676,15 @@ impl UnaryPermission<WriteQueryDescriptor> {
     &mut self,
     path: &WriteQueryDescriptor,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
     self.check_desc(Some(path), false, api_name)
   }
 
-  pub fn check_all(&mut self, api_name: Option<&str>) -> Result<(), AnyError> {
+  pub fn check_all(
+    &mut self,
+    api_name: Option<&str>,
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
     self.check_desc(None, false, api_name)
   }
@@ -1589,12 +1707,12 @@ impl UnaryPermission<NetDescriptor> {
     &mut self,
     host: &NetDescriptor,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
     self.check_desc(Some(host), false, api_name)
   }
 
-  pub fn check_all(&mut self) -> Result<(), AnyError> {
+  pub fn check_all(&mut self) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
     self.check_desc(None, false, None)
   }
@@ -1620,12 +1738,12 @@ impl UnaryPermission<ImportDescriptor> {
     &mut self,
     host: &ImportDescriptor,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
     self.check_desc(Some(host), false, api_name)
   }
 
-  pub fn check_all(&mut self) -> Result<(), AnyError> {
+  pub fn check_all(&mut self) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
     self.check_desc(None, false, None)
   }
@@ -1651,43 +1769,40 @@ impl UnaryPermission<EnvDescriptor> {
     &mut self,
     env: &str,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
     self.check_desc(Some(&EnvDescriptor::new(env)), false, api_name)
   }
 
-  pub fn check_all(&mut self) -> Result<(), AnyError> {
+  pub fn check_all(&mut self) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
     self.check_desc(None, false, None)
   }
 }
 
 impl UnaryPermission<SysDescriptor> {
-  pub fn query(&self, kind: Option<&str>) -> PermissionState {
-    self.query_desc(
-      kind.map(|k| SysDescriptor(k.to_string())).as_ref(),
-      AllowPartial::TreatAsPartialGranted,
-    )
+  pub fn query(&self, kind: Option<&SysDescriptor>) -> PermissionState {
+    self.query_desc(kind, AllowPartial::TreatAsPartialGranted)
   }
 
-  pub fn request(&mut self, kind: Option<&str>) -> PermissionState {
-    self.request_desc(kind.map(|k| SysDescriptor(k.to_string())).as_ref())
+  pub fn request(&mut self, kind: Option<&SysDescriptor>) -> PermissionState {
+    self.request_desc(kind)
   }
 
-  pub fn revoke(&mut self, kind: Option<&str>) -> PermissionState {
-    self.revoke_desc(kind.map(|k| SysDescriptor(k.to_string())).as_ref())
+  pub fn revoke(&mut self, kind: Option<&SysDescriptor>) -> PermissionState {
+    self.revoke_desc(kind)
   }
 
   pub fn check(
     &mut self,
-    kind: &str,
+    kind: &SysDescriptor,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
-    self.check_desc(Some(&SysDescriptor(kind.to_string())), false, api_name)
+    self.check_desc(Some(kind), false, api_name)
   }
 
-  pub fn check_all(&mut self) -> Result<(), AnyError> {
+  pub fn check_all(&mut self) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
     self.check_desc(None, false, None)
   }
@@ -1716,11 +1831,14 @@ impl UnaryPermission<RunQueryDescriptor> {
     &mut self,
     cmd: &RunQueryDescriptor,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     self.check_desc(Some(cmd), false, api_name)
   }
 
-  pub fn check_all(&mut self, api_name: Option<&str>) -> Result<(), AnyError> {
+  pub fn check_all(
+    &mut self,
+    api_name: Option<&str>,
+  ) -> Result<(), PermissionDeniedError> {
     self.check_desc(None, false, api_name)
   }
 
@@ -1763,7 +1881,7 @@ impl UnaryPermission<FfiQueryDescriptor> {
     &mut self,
     path: &FfiQueryDescriptor,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
     self.check_desc(Some(path), true, api_name)
   }
@@ -1771,12 +1889,12 @@ impl UnaryPermission<FfiQueryDescriptor> {
   pub fn check_partial(
     &mut self,
     path: Option<&FfiQueryDescriptor>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
     self.check_desc(path, false, None)
   }
 
-  pub fn check_all(&mut self) -> Result<(), AnyError> {
+  pub fn check_all(&mut self) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
     self.check_desc(None, false, Some("all"))
   }
@@ -1816,23 +1934,39 @@ pub struct PermissionsOptions {
   pub prompt: bool,
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum PermissionsFromOptionsError {
+  #[error("{0}")]
+  PathResolve(#[from] PathResolveError),
+  #[error("{0}")]
+  SysDescriptorParse(#[from] SysDescriptorParseError),
+  #[error("{0}")]
+  NetDescriptorParse(#[from] NetDescriptorParseError),
+  #[error("{0}")]
+  EnvDescriptorParse(#[from] EnvDescriptorParseError),
+  #[error("{0}")]
+  RunDescriptorParse(#[from] RunDescriptorParseError),
+  #[error("Empty command name not allowed in --allow-run=...")]
+  RunEmptyCommandName,
+}
+
 impl Permissions {
   pub fn new_unary<TQuery>(
     allow_list: Option<HashSet<TQuery::AllowDesc>>,
     deny_list: Option<HashSet<TQuery::DenyDesc>>,
     prompt: bool,
-  ) -> Result<UnaryPermission<TQuery>, AnyError>
+  ) -> UnaryPermission<TQuery>
   where
     TQuery: QueryDescriptor,
   {
-    Ok(UnaryPermission::<TQuery> {
+    UnaryPermission::<TQuery> {
       granted_global: global_from_option(allow_list.as_ref()),
       granted_list: allow_list.unwrap_or_default(),
       flag_denied_global: global_from_option(deny_list.as_ref()),
       flag_denied_list: deny_list.unwrap_or_default(),
       prompt,
       ..Default::default()
-    })
+    }
   }
 
   pub const fn new_all(allow_state: bool) -> UnitPermission {
@@ -1848,15 +1982,15 @@ impl Permissions {
   pub fn from_options(
     parser: &dyn PermissionDescriptorParser,
     opts: &PermissionsOptions,
-  ) -> Result<Self, AnyError> {
+  ) -> Result<Self, PermissionsFromOptionsError> {
     fn resolve_allow_run(
       parser: &dyn PermissionDescriptorParser,
       allow_run: &[String],
-    ) -> Result<HashSet<AllowRunDescriptor>, AnyError> {
+    ) -> Result<HashSet<AllowRunDescriptor>, PermissionsFromOptionsError> {
       let mut new_allow_run = HashSet::with_capacity(allow_run.len());
       for unresolved in allow_run {
         if unresolved.is_empty() {
-          bail!("Empty command name not allowed in --allow-run=...")
+          return Err(PermissionsFromOptionsError::RunEmptyCommandName);
         }
         match parser.parse_allow_run_descriptor(unresolved)? {
           AllowRunDescriptorParseResult::Descriptor(descriptor) => {
@@ -1875,10 +2009,13 @@ impl Permissions {
       Ok(new_allow_run)
     }
 
-    fn parse_maybe_vec<T: Eq + PartialEq + Hash>(
+    fn parse_maybe_vec<T: Eq + PartialEq + Hash, E>(
       items: Option<&[String]>,
-      parse: impl Fn(&str) -> Result<T, AnyError>,
-    ) -> Result<Option<HashSet<T>>, AnyError> {
+      parse: impl Fn(&str) -> Result<T, E>,
+    ) -> Result<Option<HashSet<T>>, PermissionsFromOptionsError>
+    where
+      PermissionsFromOptionsError: From<E>,
+    {
       match items {
         Some(items) => Ok(Some(
           items
@@ -1930,14 +2067,14 @@ impl Permissions {
           parser.parse_read_descriptor(item)
         })?,
         opts.prompt,
-      )?,
+      ),
       write: Permissions::new_unary(
         parse_maybe_vec(opts.allow_write.as_deref(), |item| {
           parser.parse_write_descriptor(item)
         })?,
         deny_write,
         opts.prompt,
-      )?,
+      ),
       net: Permissions::new_unary(
         parse_maybe_vec(opts.allow_net.as_deref(), |item| {
           parser.parse_net_descriptor(item)
@@ -1946,7 +2083,7 @@ impl Permissions {
           parser.parse_net_descriptor(item)
         })?,
         opts.prompt,
-      )?,
+      ),
       env: Permissions::new_unary(
         parse_maybe_vec(opts.allow_env.as_deref(), |item| {
           parser.parse_env_descriptor(item)
@@ -1955,7 +2092,7 @@ impl Permissions {
           parser.parse_env_descriptor(text)
         })?,
         opts.prompt,
-      )?,
+      ),
       sys: Permissions::new_unary(
         parse_maybe_vec(opts.allow_sys.as_deref(), |text| {
           parser.parse_sys_descriptor(text)
@@ -1964,14 +2101,14 @@ impl Permissions {
           parser.parse_sys_descriptor(text)
         })?,
         opts.prompt,
-      )?,
+      ),
       run: Permissions::new_unary(
         allow_run,
         parse_maybe_vec(opts.deny_run.as_deref(), |text| {
           parser.parse_deny_run_descriptor(text)
         })?,
         opts.prompt,
-      )?,
+      ),
       ffi: Permissions::new_unary(
         parse_maybe_vec(opts.allow_ffi.as_deref(), |text| {
           parser.parse_ffi_descriptor(text)
@@ -1980,14 +2117,14 @@ impl Permissions {
           parser.parse_ffi_descriptor(text)
         })?,
         opts.prompt,
-      )?,
+      ),
       import: Permissions::new_unary(
         parse_maybe_vec(opts.allow_import.as_deref(), |item| {
           parser.parse_import_descriptor(item)
         })?,
         None,
         opts.prompt,
-      )?,
+      ),
       all: Permissions::new_all(opts.allow_all),
     })
   }
@@ -2019,71 +2156,57 @@ impl Permissions {
 
   fn none(prompt: bool) -> Self {
     Self {
-      read: Permissions::new_unary(None, None, prompt).unwrap(),
-      write: Permissions::new_unary(None, None, prompt).unwrap(),
-      net: Permissions::new_unary(None, None, prompt).unwrap(),
-      env: Permissions::new_unary(None, None, prompt).unwrap(),
-      sys: Permissions::new_unary(None, None, prompt).unwrap(),
-      run: Permissions::new_unary(None, None, prompt).unwrap(),
-      ffi: Permissions::new_unary(None, None, prompt).unwrap(),
-      import: Permissions::new_unary(None, None, prompt).unwrap(),
+      read: Permissions::new_unary(None, None, prompt),
+      write: Permissions::new_unary(None, None, prompt),
+      net: Permissions::new_unary(None, None, prompt),
+      env: Permissions::new_unary(None, None, prompt),
+      sys: Permissions::new_unary(None, None, prompt),
+      run: Permissions::new_unary(None, None, prompt),
+      ffi: Permissions::new_unary(None, None, prompt),
+      import: Permissions::new_unary(None, None, prompt),
       all: Permissions::new_all(false),
     }
   }
 }
 
-/// Attempts to convert a specifier to a file path. By default, uses the Url
-/// crate's `to_file_path()` method, but falls back to try and resolve unix-style
-/// paths on Windows.
-pub fn specifier_to_file_path(
-  specifier: &ModuleSpecifier,
-) -> Result<PathBuf, AnyError> {
-  let result = if specifier.scheme() != "file" {
-    Err(())
-  } else if cfg!(windows) {
-    if specifier.host().is_some() {
-      Err(())
-    } else {
-      match specifier.to_file_path() {
-        Ok(path) => Ok(path),
-        Err(()) => {
-          // This might be a unix-style path which is used in the tests even on Windows.
-          // Attempt to see if we can convert it to a `PathBuf`. This code should be removed
-          // once/if https://github.com/servo/rust-url/issues/730 is implemented.
-          if specifier.scheme() == "file"
-            && specifier.port().is_none()
-            && specifier.path_segments().is_some()
-          {
-            let path_str = specifier.path();
-            match String::from_utf8(
-              percent_encoding::percent_decode(path_str.as_bytes()).collect(),
-            ) {
-              Ok(path_str) => Ok(PathBuf::from(path_str)),
-              Err(_) => Err(()),
-            }
-          } else {
-            Err(())
-          }
-        }
-      }
-    }
-  } else {
-    specifier.to_file_path()
-  };
-  match result {
-    Ok(path) => Ok(path),
-    Err(()) => Err(uri_error(format!(
-      "Invalid file path.\n  Specifier: {specifier}"
-    ))),
-  }
-}
-
 #[derive(Debug, Clone, Copy, Eq, PartialEq)]
 pub enum CheckSpecifierKind {
   Static,
   Dynamic,
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum ChildPermissionError {
+  #[error("Can't escalate parent thread permissions")]
+  Escalation,
+  #[error("{0}")]
+  PathResolve(#[from] PathResolveError),
+  #[error("{0}")]
+  NetDescriptorParse(#[from] NetDescriptorParseError),
+  #[error("{0}")]
+  EnvDescriptorParse(#[from] EnvDescriptorParseError),
+  #[error("{0}")]
+  SysDescriptorParse(#[from] SysDescriptorParseError),
+  #[error("{0}")]
+  RunDescriptorParse(#[from] RunDescriptorParseError),
+}
+
+#[derive(Debug, thiserror::Error)]
+pub enum PermissionCheckError {
+  #[error(transparent)]
+  PermissionDenied(#[from] PermissionDeniedError),
+  #[error("Invalid file path.\n  Specifier: {0}")]
+  InvalidFilePath(Url),
+  #[error(transparent)]
+  NetDescriptorForUrlParse(#[from] NetDescriptorFromUrlParseError),
+  #[error(transparent)]
+  SysDescriptorParse(#[from] SysDescriptorParseError),
+  #[error(transparent)]
+  PathResolve(#[from] PathResolveError),
+  #[error(transparent)]
+  HostParse(#[from] HostParseError),
+}
+
 /// Wrapper struct for `Permissions` that can be shared across threads.
 ///
 /// We need a way to have internal mutability for permissions as they might get
@@ -2092,12 +2215,8 @@ pub enum CheckSpecifierKind {
 /// to send permissions to a new thread.
 #[derive(Clone, Debug)]
 pub struct PermissionsContainer {
-  // todo(dsherret): make both of these private as the functionality
-  // can just be methods on PermissionsContainer. Additionally, a separate
-  // struct should be created in here that handles creating child permissions
-  // so that the code is not so verbose elsewhere.
-  pub descriptor_parser: Arc<dyn PermissionDescriptorParser>,
-  pub inner: Arc<Mutex<Permissions>>,
+  descriptor_parser: Arc<dyn PermissionDescriptorParser>,
+  inner: Arc<Mutex<Permissions>>,
 }
 
 impl PermissionsContainer {
@@ -2117,12 +2236,125 @@ impl PermissionsContainer {
     Self::new(descriptor_parser, Permissions::allow_all())
   }
 
+  pub fn create_child_permissions(
+    &self,
+    child_permissions_arg: ChildPermissionsArg,
+  ) -> Result<PermissionsContainer, ChildPermissionError> {
+    fn is_granted_unary(arg: &ChildUnaryPermissionArg) -> bool {
+      match arg {
+        ChildUnaryPermissionArg::Inherit | ChildUnaryPermissionArg::Granted => {
+          true
+        }
+        ChildUnaryPermissionArg::NotGranted
+        | ChildUnaryPermissionArg::GrantedList(_) => false,
+      }
+    }
+
+    let mut worker_perms = Permissions::none_without_prompt();
+
+    let mut inner = self.inner.lock();
+    worker_perms.all = inner
+      .all
+      .create_child_permissions(ChildUnitPermissionArg::Inherit)?;
+
+    // downgrade the `worker_perms.all` based on the other values
+    if worker_perms.all.query() == PermissionState::Granted {
+      let unary_perms = [
+        &child_permissions_arg.read,
+        &child_permissions_arg.write,
+        &child_permissions_arg.net,
+        &child_permissions_arg.import,
+        &child_permissions_arg.env,
+        &child_permissions_arg.sys,
+        &child_permissions_arg.run,
+        &child_permissions_arg.ffi,
+      ];
+      let allow_all = unary_perms.into_iter().all(is_granted_unary);
+      if !allow_all {
+        worker_perms.all.revoke();
+      }
+    }
+
+    // WARNING: When adding a permission here, ensure it is handled
+    // in the worker_perms.all block above
+    worker_perms.read = inner.read.create_child_permissions(
+      child_permissions_arg.read,
+      |text| {
+        Ok::<_, PathResolveError>(Some(
+          self.descriptor_parser.parse_read_descriptor(text)?,
+        ))
+      },
+    )?;
+    worker_perms.write = inner.write.create_child_permissions(
+      child_permissions_arg.write,
+      |text| {
+        Ok::<_, PathResolveError>(Some(
+          self.descriptor_parser.parse_write_descriptor(text)?,
+        ))
+      },
+    )?;
+    worker_perms.import = inner.import.create_child_permissions(
+      child_permissions_arg.import,
+      |text| {
+        Ok::<_, NetDescriptorParseError>(Some(
+          self.descriptor_parser.parse_import_descriptor(text)?,
+        ))
+      },
+    )?;
+    worker_perms.net = inner.net.create_child_permissions(
+      child_permissions_arg.net,
+      |text| {
+        Ok::<_, NetDescriptorParseError>(Some(
+          self.descriptor_parser.parse_net_descriptor(text)?,
+        ))
+      },
+    )?;
+    worker_perms.env = inner.env.create_child_permissions(
+      child_permissions_arg.env,
+      |text| {
+        Ok::<_, EnvDescriptorParseError>(Some(
+          self.descriptor_parser.parse_env_descriptor(text)?,
+        ))
+      },
+    )?;
+    worker_perms.sys = inner.sys.create_child_permissions(
+      child_permissions_arg.sys,
+      |text| {
+        Ok::<_, SysDescriptorParseError>(Some(
+          self.descriptor_parser.parse_sys_descriptor(text)?,
+        ))
+      },
+    )?;
+    worker_perms.run = inner.run.create_child_permissions(
+      child_permissions_arg.run,
+      |text| match self.descriptor_parser.parse_allow_run_descriptor(text)? {
+        AllowRunDescriptorParseResult::Unresolved(_) => {
+          Ok::<_, RunDescriptorParseError>(None)
+        }
+        AllowRunDescriptorParseResult::Descriptor(desc) => Ok(Some(desc)),
+      },
+    )?;
+    worker_perms.ffi = inner.ffi.create_child_permissions(
+      child_permissions_arg.ffi,
+      |text| {
+        Ok::<_, PathResolveError>(Some(
+          self.descriptor_parser.parse_ffi_descriptor(text)?,
+        ))
+      },
+    )?;
+
+    Ok(PermissionsContainer::new(
+      self.descriptor_parser.clone(),
+      worker_perms,
+    ))
+  }
+
   #[inline(always)]
   pub fn check_specifier(
     &self,
     specifier: &ModuleSpecifier,
     kind: CheckSpecifierKind,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     let mut inner = self.inner.lock();
     match specifier.scheme() {
       "file" => {
@@ -2130,18 +2362,21 @@ impl PermissionsContainer {
           return Ok(());
         }
 
-        match specifier_to_file_path(specifier) {
-          Ok(path) => inner.read.check(
-            &PathQueryDescriptor {
-              requested: path.to_string_lossy().into_owned(),
-              resolved: path,
-            }
-            .into_read(),
-            Some("import()"),
-          ),
-          Err(_) => Err(uri_error(format!(
-            "Invalid file path.\n  Specifier: {specifier}"
-          ))),
+        match url_to_file_path(specifier) {
+          Ok(path) => inner
+            .read
+            .check(
+              &PathQueryDescriptor {
+                requested: path.to_string_lossy().into_owned(),
+                resolved: path,
+              }
+              .into_read(),
+              Some("import()"),
+            )
+            .map_err(PermissionCheckError::PermissionDenied),
+          Err(_) => {
+            Err(PermissionCheckError::InvalidFilePath(specifier.clone()))
+          }
         }
       }
       "data" => Ok(()),
@@ -2166,7 +2401,7 @@ impl PermissionsContainer {
     &self,
     path: &str,
     api_name: &str,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     self.check_read_with_api_name(path, Some(api_name))
   }
 
@@ -2176,7 +2411,7 @@ impl PermissionsContainer {
     &self,
     path: &str,
     api_name: Option<&str>,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     let mut inner = self.inner.lock();
     let inner = &mut inner.read;
     if inner.is_allow_all() {
@@ -2194,7 +2429,7 @@ impl PermissionsContainer {
     &self,
     path: &'a Path,
     api_name: Option<&str>,
-  ) -> Result<Cow<'a, Path>, AnyError> {
+  ) -> Result<Cow<'a, Path>, PermissionCheckError> {
     let mut inner = self.inner.lock();
     let inner = &mut inner.read;
     if inner.is_allow_all() {
@@ -2218,7 +2453,7 @@ impl PermissionsContainer {
     path: &Path,
     display: &str,
     api_name: &str,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     let mut inner = self.inner.lock();
     let inner = &mut inner.read;
     skip_check_if_is_permission_fully_granted!(inner);
@@ -2229,12 +2464,22 @@ impl PermissionsContainer {
       }
       .into_read(),
       Some(api_name),
-    )
+    )?;
+    Ok(())
   }
 
   #[inline(always)]
-  pub fn check_read_all(&self, api_name: &str) -> Result<(), AnyError> {
-    self.inner.lock().read.check_all(Some(api_name))
+  pub fn check_read_all(
+    &self,
+    api_name: &str,
+  ) -> Result<(), PermissionCheckError> {
+    self.inner.lock().read.check_all(Some(api_name))?;
+    Ok(())
+  }
+
+  #[inline(always)]
+  pub fn query_read_all(&self) -> bool {
+    self.inner.lock().read.query(None) == PermissionState::Granted
   }
 
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
@@ -2243,7 +2488,7 @@ impl PermissionsContainer {
     &self,
     path: &str,
     api_name: &str,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     self.check_write_with_api_name(path, Some(api_name))
   }
 
@@ -2253,7 +2498,7 @@ impl PermissionsContainer {
     &self,
     path: &str,
     api_name: Option<&str>,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     let mut inner = self.inner.lock();
     let inner = &mut inner.write;
     if inner.is_allow_all() {
@@ -2271,7 +2516,7 @@ impl PermissionsContainer {
     &self,
     path: &'a Path,
     api_name: &str,
-  ) -> Result<Cow<'a, Path>, AnyError> {
+  ) -> Result<Cow<'a, Path>, PermissionCheckError> {
     let mut inner = self.inner.lock();
     let inner = &mut inner.write;
     if inner.is_allow_all() {
@@ -2288,8 +2533,12 @@ impl PermissionsContainer {
   }
 
   #[inline(always)]
-  pub fn check_write_all(&self, api_name: &str) -> Result<(), AnyError> {
-    self.inner.lock().write.check_all(Some(api_name))
+  pub fn check_write_all(
+    &self,
+    api_name: &str,
+  ) -> Result<(), PermissionCheckError> {
+    self.inner.lock().write.check_all(Some(api_name))?;
+    Ok(())
   }
 
   /// As `check_write()`, but permission error messages will anonymize the path
@@ -2300,7 +2549,7 @@ impl PermissionsContainer {
     path: &Path,
     display: &str,
     api_name: &str,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     let mut inner = self.inner.lock();
     let inner = &mut inner.write;
     skip_check_if_is_permission_fully_granted!(inner);
@@ -2311,7 +2560,8 @@ impl PermissionsContainer {
       }
       .into_write(),
       Some(api_name),
-    )
+    )?;
+    Ok(())
   }
 
   #[inline(always)]
@@ -2319,7 +2569,7 @@ impl PermissionsContainer {
     &mut self,
     path: &str,
     api_name: &str,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     let mut inner = self.inner.lock();
     let inner = &mut inner.write;
     if inner.is_allow_all() {
@@ -2336,13 +2586,18 @@ impl PermissionsContainer {
     &mut self,
     cmd: &RunQueryDescriptor,
     api_name: &str,
-  ) -> Result<(), AnyError> {
-    self.inner.lock().run.check(cmd, Some(api_name))
+  ) -> Result<(), PermissionCheckError> {
+    self.inner.lock().run.check(cmd, Some(api_name))?;
+    Ok(())
   }
 
   #[inline(always)]
-  pub fn check_run_all(&mut self, api_name: &str) -> Result<(), AnyError> {
-    self.inner.lock().run.check_all(Some(api_name))
+  pub fn check_run_all(
+    &mut self,
+    api_name: &str,
+  ) -> Result<(), PermissionCheckError> {
+    self.inner.lock().run.check_all(Some(api_name))?;
+    Ok(())
   }
 
   #[inline(always)]
@@ -2351,35 +2606,50 @@ impl PermissionsContainer {
   }
 
   #[inline(always)]
-  pub fn check_sys(&self, kind: &str, api_name: &str) -> Result<(), AnyError> {
-    self.inner.lock().sys.check(kind, Some(api_name))
+  pub fn check_sys(
+    &self,
+    kind: &str,
+    api_name: &str,
+  ) -> Result<(), PermissionCheckError> {
+    self.inner.lock().sys.check(
+      &self.descriptor_parser.parse_sys_descriptor(kind)?,
+      Some(api_name),
+    )?;
+    Ok(())
   }
 
   #[inline(always)]
-  pub fn check_env(&mut self, var: &str) -> Result<(), AnyError> {
-    self.inner.lock().env.check(var, None)
+  pub fn check_env(&mut self, var: &str) -> Result<(), PermissionCheckError> {
+    self.inner.lock().env.check(var, None)?;
+    Ok(())
   }
 
   #[inline(always)]
-  pub fn check_env_all(&mut self) -> Result<(), AnyError> {
-    self.inner.lock().env.check_all()
+  pub fn check_env_all(&mut self) -> Result<(), PermissionCheckError> {
+    self.inner.lock().env.check_all()?;
+    Ok(())
   }
 
   #[inline(always)]
-  pub fn check_sys_all(&mut self) -> Result<(), AnyError> {
-    self.inner.lock().sys.check_all()
+  pub fn check_sys_all(&mut self) -> Result<(), PermissionCheckError> {
+    self.inner.lock().sys.check_all()?;
+    Ok(())
   }
 
   #[inline(always)]
-  pub fn check_ffi_all(&mut self) -> Result<(), AnyError> {
-    self.inner.lock().ffi.check_all()
+  pub fn check_ffi_all(&mut self) -> Result<(), PermissionCheckError> {
+    self.inner.lock().ffi.check_all()?;
+    Ok(())
   }
 
   /// This checks to see if the allow-all flag was passed, not whether all
   /// permissions are enabled!
   #[inline(always)]
-  pub fn check_was_allow_all_flag_passed(&mut self) -> Result<(), AnyError> {
-    self.inner.lock().all.check()
+  pub fn check_was_allow_all_flag_passed(
+    &mut self,
+  ) -> Result<(), PermissionCheckError> {
+    self.inner.lock().all.check()?;
+    Ok(())
   }
 
   /// Checks special file access, returning the failed permission type if
@@ -2491,13 +2761,14 @@ impl PermissionsContainer {
     &mut self,
     url: &Url,
     api_name: &str,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     let mut inner = self.inner.lock();
     if inner.net.is_allow_all() {
       return Ok(());
     }
     let desc = self.descriptor_parser.parse_net_descriptor_from_url(url)?;
-    inner.net.check(&desc, Some(api_name))
+    inner.net.check(&desc, Some(api_name))?;
+    Ok(())
   }
 
   #[inline(always)]
@@ -2505,17 +2776,21 @@ impl PermissionsContainer {
     &mut self,
     host: &(T, Option<u16>),
     api_name: &str,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     let mut inner = self.inner.lock();
     let inner = &mut inner.net;
     skip_check_if_is_permission_fully_granted!(inner);
     let hostname = Host::parse(host.0.as_ref())?;
     let descriptor = NetDescriptor(hostname, host.1);
-    inner.check(&descriptor, Some(api_name))
+    inner.check(&descriptor, Some(api_name))?;
+    Ok(())
   }
 
   #[inline(always)]
-  pub fn check_ffi(&mut self, path: &str) -> Result<PathBuf, AnyError> {
+  pub fn check_ffi(
+    &mut self,
+    path: &str,
+  ) -> Result<PathBuf, PermissionCheckError> {
     let mut inner = self.inner.lock();
     let inner = &mut inner.ffi;
     if inner.is_allow_all() {
@@ -2529,14 +2804,15 @@ impl PermissionsContainer {
 
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
   #[inline(always)]
-  pub fn check_ffi_partial_no_path(&mut self) -> Result<(), AnyError> {
+  pub fn check_ffi_partial_no_path(
+    &mut self,
+  ) -> Result<(), PermissionCheckError> {
     let mut inner = self.inner.lock();
     let inner = &mut inner.ffi;
-    if inner.is_allow_all() {
-      Ok(())
-    } else {
-      inner.check_partial(None)
+    if !inner.is_allow_all() {
+      inner.check_partial(None)?;
     }
+    Ok(())
   }
 
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
@@ -2544,7 +2820,7 @@ impl PermissionsContainer {
   pub fn check_ffi_partial_with_path(
     &mut self,
     path: &str,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     let mut inner = self.inner.lock();
     let inner = &mut inner.ffi;
     if inner.is_allow_all() {
@@ -2555,6 +2831,371 @@ impl PermissionsContainer {
       Ok(desc.0.resolved)
     }
   }
+
+  // query
+
+  #[inline(always)]
+  pub fn query_read(
+    &self,
+    path: Option<&str>,
+  ) -> Result<PermissionState, PathResolveError> {
+    let inner = self.inner.lock();
+    let permission = &inner.read;
+    if permission.is_allow_all() {
+      return Ok(PermissionState::Granted);
+    }
+    Ok(
+      permission.query(
+        path
+          .map(|path| {
+            Ok::<_, PathResolveError>(
+              self.descriptor_parser.parse_path_query(path)?.into_read(),
+            )
+          })
+          .transpose()?
+          .as_ref(),
+      ),
+    )
+  }
+
+  #[inline(always)]
+  pub fn query_write(
+    &self,
+    path: Option<&str>,
+  ) -> Result<PermissionState, PathResolveError> {
+    let inner = self.inner.lock();
+    let permission = &inner.write;
+    if permission.is_allow_all() {
+      return Ok(PermissionState::Granted);
+    }
+    Ok(
+      permission.query(
+        path
+          .map(|path| {
+            Ok::<_, PathResolveError>(
+              self.descriptor_parser.parse_path_query(path)?.into_write(),
+            )
+          })
+          .transpose()?
+          .as_ref(),
+      ),
+    )
+  }
+
+  #[inline(always)]
+  pub fn query_net(
+    &self,
+    host: Option<&str>,
+  ) -> Result<PermissionState, NetDescriptorParseError> {
+    let inner = self.inner.lock();
+    let permission = &inner.net;
+    if permission.is_allow_all() {
+      return Ok(PermissionState::Granted);
+    }
+    Ok(
+      permission.query(
+        match host {
+          None => None,
+          Some(h) => Some(self.descriptor_parser.parse_net_descriptor(h)?),
+        }
+        .as_ref(),
+      ),
+    )
+  }
+
+  #[inline(always)]
+  pub fn query_env(&self, var: Option<&str>) -> PermissionState {
+    let inner = self.inner.lock();
+    let permission = &inner.env;
+    if permission.is_allow_all() {
+      return PermissionState::Granted;
+    }
+    permission.query(var)
+  }
+
+  #[inline(always)]
+  pub fn query_sys(
+    &self,
+    kind: Option<&str>,
+  ) -> Result<PermissionState, SysDescriptorParseError> {
+    let inner = self.inner.lock();
+    let permission = &inner.sys;
+    if permission.is_allow_all() {
+      return Ok(PermissionState::Granted);
+    }
+    Ok(
+      permission.query(
+        kind
+          .map(|kind| self.descriptor_parser.parse_sys_descriptor(kind))
+          .transpose()?
+          .as_ref(),
+      ),
+    )
+  }
+
+  #[inline(always)]
+  pub fn query_run(
+    &self,
+    cmd: Option<&str>,
+  ) -> Result<PermissionState, RunDescriptorParseError> {
+    let inner = self.inner.lock();
+    let permission = &inner.run;
+    if permission.is_allow_all() {
+      return Ok(PermissionState::Granted);
+    }
+    Ok(
+      permission.query(
+        cmd
+          .map(|request| self.descriptor_parser.parse_run_query(request))
+          .transpose()?
+          .as_ref(),
+      ),
+    )
+  }
+
+  #[inline(always)]
+  pub fn query_ffi(
+    &self,
+    path: Option<&str>,
+  ) -> Result<PermissionState, PathResolveError> {
+    let inner = self.inner.lock();
+    let permission = &inner.ffi;
+    if permission.is_allow_all() {
+      return Ok(PermissionState::Granted);
+    }
+    Ok(
+      permission.query(
+        path
+          .map(|path| {
+            Ok::<_, PathResolveError>(
+              self.descriptor_parser.parse_path_query(path)?.into_ffi(),
+            )
+          })
+          .transpose()?
+          .as_ref(),
+      ),
+    )
+  }
+
+  // revoke
+
+  #[inline(always)]
+  pub fn revoke_read(
+    &self,
+    path: Option<&str>,
+  ) -> Result<PermissionState, PathResolveError> {
+    Ok(
+      self.inner.lock().read.revoke(
+        path
+          .map(|path| {
+            Ok::<_, PathResolveError>(
+              self.descriptor_parser.parse_path_query(path)?.into_read(),
+            )
+          })
+          .transpose()?
+          .as_ref(),
+      ),
+    )
+  }
+
+  #[inline(always)]
+  pub fn revoke_write(
+    &self,
+    path: Option<&str>,
+  ) -> Result<PermissionState, PathResolveError> {
+    Ok(
+      self.inner.lock().write.revoke(
+        path
+          .map(|path| {
+            Ok::<_, PathResolveError>(
+              self.descriptor_parser.parse_path_query(path)?.into_write(),
+            )
+          })
+          .transpose()?
+          .as_ref(),
+      ),
+    )
+  }
+
+  #[inline(always)]
+  pub fn revoke_net(
+    &self,
+    host: Option<&str>,
+  ) -> Result<PermissionState, NetDescriptorParseError> {
+    Ok(
+      self.inner.lock().net.revoke(
+        match host {
+          None => None,
+          Some(h) => Some(self.descriptor_parser.parse_net_descriptor(h)?),
+        }
+        .as_ref(),
+      ),
+    )
+  }
+
+  #[inline(always)]
+  pub fn revoke_env(&self, var: Option<&str>) -> PermissionState {
+    self.inner.lock().env.revoke(var)
+  }
+
+  #[inline(always)]
+  pub fn revoke_sys(
+    &self,
+    kind: Option<&str>,
+  ) -> Result<PermissionState, SysDescriptorParseError> {
+    Ok(
+      self.inner.lock().sys.revoke(
+        kind
+          .map(|kind| self.descriptor_parser.parse_sys_descriptor(kind))
+          .transpose()?
+          .as_ref(),
+      ),
+    )
+  }
+
+  #[inline(always)]
+  pub fn revoke_run(
+    &self,
+    cmd: Option<&str>,
+  ) -> Result<PermissionState, RunDescriptorParseError> {
+    Ok(
+      self.inner.lock().run.revoke(
+        cmd
+          .map(|request| self.descriptor_parser.parse_run_query(request))
+          .transpose()?
+          .as_ref(),
+      ),
+    )
+  }
+
+  #[inline(always)]
+  pub fn revoke_ffi(
+    &self,
+    path: Option<&str>,
+  ) -> Result<PermissionState, PathResolveError> {
+    Ok(
+      self.inner.lock().ffi.revoke(
+        path
+          .map(|path| {
+            Ok::<_, PathResolveError>(
+              self.descriptor_parser.parse_path_query(path)?.into_ffi(),
+            )
+          })
+          .transpose()?
+          .as_ref(),
+      ),
+    )
+  }
+
+  // request
+
+  #[inline(always)]
+  pub fn request_read(
+    &self,
+    path: Option<&str>,
+  ) -> Result<PermissionState, PathResolveError> {
+    Ok(
+      self.inner.lock().read.request(
+        path
+          .map(|path| {
+            Ok::<_, PathResolveError>(
+              self.descriptor_parser.parse_path_query(path)?.into_read(),
+            )
+          })
+          .transpose()?
+          .as_ref(),
+      ),
+    )
+  }
+
+  #[inline(always)]
+  pub fn request_write(
+    &self,
+    path: Option<&str>,
+  ) -> Result<PermissionState, PathResolveError> {
+    Ok(
+      self.inner.lock().write.request(
+        path
+          .map(|path| {
+            Ok::<_, PathResolveError>(
+              self.descriptor_parser.parse_path_query(path)?.into_write(),
+            )
+          })
+          .transpose()?
+          .as_ref(),
+      ),
+    )
+  }
+
+  #[inline(always)]
+  pub fn request_net(
+    &self,
+    host: Option<&str>,
+  ) -> Result<PermissionState, NetDescriptorParseError> {
+    Ok(
+      self.inner.lock().net.request(
+        match host {
+          None => None,
+          Some(h) => Some(self.descriptor_parser.parse_net_descriptor(h)?),
+        }
+        .as_ref(),
+      ),
+    )
+  }
+
+  #[inline(always)]
+  pub fn request_env(&self, var: Option<&str>) -> PermissionState {
+    self.inner.lock().env.request(var)
+  }
+
+  #[inline(always)]
+  pub fn request_sys(
+    &self,
+    kind: Option<&str>,
+  ) -> Result<PermissionState, SysDescriptorParseError> {
+    Ok(
+      self.inner.lock().sys.request(
+        kind
+          .map(|kind| self.descriptor_parser.parse_sys_descriptor(kind))
+          .transpose()?
+          .as_ref(),
+      ),
+    )
+  }
+
+  #[inline(always)]
+  pub fn request_run(
+    &self,
+    cmd: Option<&str>,
+  ) -> Result<PermissionState, RunDescriptorParseError> {
+    Ok(
+      self.inner.lock().run.request(
+        cmd
+          .map(|request| self.descriptor_parser.parse_run_query(request))
+          .transpose()?
+          .as_ref(),
+      ),
+    )
+  }
+
+  #[inline(always)]
+  pub fn request_ffi(
+    &self,
+    path: Option<&str>,
+  ) -> Result<PermissionState, PathResolveError> {
+    Ok(
+      self.inner.lock().ffi.request(
+        path
+          .map(|path| {
+            Ok::<_, PathResolveError>(
+              self.descriptor_parser.parse_path_query(path)?.into_ffi(),
+            )
+          })
+          .transpose()?
+          .as_ref(),
+      ),
+    )
+  }
 }
 
 const fn unit_permission_from_flag_bools(
@@ -2582,10 +3223,6 @@ fn global_from_option<T>(flag: Option<&HashSet<T>>) -> bool {
   matches!(flag, Some(v) if v.is_empty())
 }
 
-fn escalation_error() -> AnyError {
-  custom_error("NotCapable", "Can't escalate parent thread permissions")
-}
-
 #[derive(Debug, Eq, PartialEq)]
 pub enum ChildUnitPermissionArg {
   Inherit,
@@ -2846,152 +3483,73 @@ pub trait PermissionDescriptorParser: Debug + Send + Sync {
   fn parse_read_descriptor(
     &self,
     text: &str,
-  ) -> Result<ReadDescriptor, AnyError>;
+  ) -> Result<ReadDescriptor, PathResolveError>;
 
   fn parse_write_descriptor(
     &self,
     text: &str,
-  ) -> Result<WriteDescriptor, AnyError>;
+  ) -> Result<WriteDescriptor, PathResolveError>;
 
-  fn parse_net_descriptor(&self, text: &str)
-    -> Result<NetDescriptor, AnyError>;
+  fn parse_net_descriptor(
+    &self,
+    text: &str,
+  ) -> Result<NetDescriptor, NetDescriptorParseError>;
 
   fn parse_net_descriptor_from_url(
     &self,
     url: &Url,
-  ) -> Result<NetDescriptor, AnyError> {
+  ) -> Result<NetDescriptor, NetDescriptorFromUrlParseError> {
     NetDescriptor::from_url(url)
   }
 
   fn parse_import_descriptor(
     &self,
     text: &str,
-  ) -> Result<ImportDescriptor, AnyError>;
+  ) -> Result<ImportDescriptor, NetDescriptorParseError>;
 
   fn parse_import_descriptor_from_url(
     &self,
     url: &Url,
-  ) -> Result<ImportDescriptor, AnyError> {
+  ) -> Result<ImportDescriptor, NetDescriptorFromUrlParseError> {
     ImportDescriptor::from_url(url)
   }
 
-  fn parse_env_descriptor(&self, text: &str)
-    -> Result<EnvDescriptor, AnyError>;
+  fn parse_env_descriptor(
+    &self,
+    text: &str,
+  ) -> Result<EnvDescriptor, EnvDescriptorParseError>;
 
-  fn parse_sys_descriptor(&self, text: &str)
-    -> Result<SysDescriptor, AnyError>;
+  fn parse_sys_descriptor(
+    &self,
+    text: &str,
+  ) -> Result<SysDescriptor, SysDescriptorParseError>;
 
   fn parse_allow_run_descriptor(
     &self,
     text: &str,
-  ) -> Result<AllowRunDescriptorParseResult, AnyError>;
+  ) -> Result<AllowRunDescriptorParseResult, RunDescriptorParseError>;
 
   fn parse_deny_run_descriptor(
     &self,
     text: &str,
-  ) -> Result<DenyRunDescriptor, AnyError>;
+  ) -> Result<DenyRunDescriptor, PathResolveError>;
 
-  fn parse_ffi_descriptor(&self, text: &str)
-    -> Result<FfiDescriptor, AnyError>;
+  fn parse_ffi_descriptor(
+    &self,
+    text: &str,
+  ) -> Result<FfiDescriptor, PathResolveError>;
 
   // queries
 
   fn parse_path_query(
     &self,
     path: &str,
-  ) -> Result<PathQueryDescriptor, AnyError>;
+  ) -> Result<PathQueryDescriptor, PathResolveError>;
 
   fn parse_run_query(
     &self,
     requested: &str,
-  ) -> Result<RunQueryDescriptor, AnyError>;
-}
-
-pub fn create_child_permissions(
-  parser: &dyn PermissionDescriptorParser,
-  main_perms: &mut Permissions,
-  child_permissions_arg: ChildPermissionsArg,
-) -> Result<Permissions, AnyError> {
-  fn is_granted_unary(arg: &ChildUnaryPermissionArg) -> bool {
-    match arg {
-      ChildUnaryPermissionArg::Inherit | ChildUnaryPermissionArg::Granted => {
-        true
-      }
-      ChildUnaryPermissionArg::NotGranted
-      | ChildUnaryPermissionArg::GrantedList(_) => false,
-    }
-  }
-
-  let mut worker_perms = Permissions::none_without_prompt();
-
-  worker_perms.all = main_perms
-    .all
-    .create_child_permissions(ChildUnitPermissionArg::Inherit)?;
-
-  // downgrade the `worker_perms.all` based on the other values
-  if worker_perms.all.query() == PermissionState::Granted {
-    let unary_perms = [
-      &child_permissions_arg.read,
-      &child_permissions_arg.write,
-      &child_permissions_arg.net,
-      &child_permissions_arg.import,
-      &child_permissions_arg.env,
-      &child_permissions_arg.sys,
-      &child_permissions_arg.run,
-      &child_permissions_arg.ffi,
-    ];
-    let allow_all = unary_perms.into_iter().all(is_granted_unary);
-    if !allow_all {
-      worker_perms.all.revoke();
-    }
-  }
-
-  // WARNING: When adding a permission here, ensure it is handled
-  // in the worker_perms.all block above
-  worker_perms.read = main_perms
-    .read
-    .create_child_permissions(child_permissions_arg.read, |text| {
-      Ok(Some(parser.parse_read_descriptor(text)?))
-    })?;
-  worker_perms.write = main_perms
-    .write
-    .create_child_permissions(child_permissions_arg.write, |text| {
-      Ok(Some(parser.parse_write_descriptor(text)?))
-    })?;
-  worker_perms.import = main_perms
-    .import
-    .create_child_permissions(child_permissions_arg.import, |text| {
-      Ok(Some(parser.parse_import_descriptor(text)?))
-    })?;
-  worker_perms.net = main_perms
-    .net
-    .create_child_permissions(child_permissions_arg.net, |text| {
-      Ok(Some(parser.parse_net_descriptor(text)?))
-    })?;
-  worker_perms.env = main_perms
-    .env
-    .create_child_permissions(child_permissions_arg.env, |text| {
-      Ok(Some(parser.parse_env_descriptor(text)?))
-    })?;
-  worker_perms.sys = main_perms
-    .sys
-    .create_child_permissions(child_permissions_arg.sys, |text| {
-      Ok(Some(parser.parse_sys_descriptor(text)?))
-    })?;
-  worker_perms.run = main_perms.run.create_child_permissions(
-    child_permissions_arg.run,
-    |text| match parser.parse_allow_run_descriptor(text)? {
-      AllowRunDescriptorParseResult::Unresolved(_) => Ok(None),
-      AllowRunDescriptorParseResult::Descriptor(desc) => Ok(Some(desc)),
-    },
-  )?;
-  worker_perms.ffi = main_perms
-    .ffi
-    .create_child_permissions(child_permissions_arg.ffi, |text| {
-      Ok(Some(parser.parse_ffi_descriptor(text)?))
-    })?;
-
-  Ok(worker_perms)
+  ) -> Result<RunQueryDescriptor, RunDescriptorParseError>;
 }
 
 static IS_STANDALONE: AtomicFlag = AtomicFlag::lowered();
@@ -3017,7 +3575,7 @@ mod tests {
       ($($x:expr),*) => (vec![$($x.to_string()),*]);
   }
 
-  #[derive(Debug)]
+  #[derive(Debug, Clone)]
   struct TestPermissionDescriptorParser;
 
   impl TestPermissionDescriptorParser {
@@ -3034,49 +3592,49 @@ mod tests {
     fn parse_read_descriptor(
       &self,
       text: &str,
-    ) -> Result<ReadDescriptor, AnyError> {
+    ) -> Result<ReadDescriptor, PathResolveError> {
       Ok(ReadDescriptor(self.join_path_with_root(text)))
     }
 
     fn parse_write_descriptor(
       &self,
       text: &str,
-    ) -> Result<WriteDescriptor, AnyError> {
+    ) -> Result<WriteDescriptor, PathResolveError> {
       Ok(WriteDescriptor(self.join_path_with_root(text)))
     }
 
     fn parse_net_descriptor(
       &self,
       text: &str,
-    ) -> Result<NetDescriptor, AnyError> {
+    ) -> Result<NetDescriptor, NetDescriptorParseError> {
       NetDescriptor::parse(text)
     }
 
     fn parse_import_descriptor(
       &self,
       text: &str,
-    ) -> Result<ImportDescriptor, AnyError> {
+    ) -> Result<ImportDescriptor, NetDescriptorParseError> {
       ImportDescriptor::parse(text)
     }
 
     fn parse_env_descriptor(
       &self,
       text: &str,
-    ) -> Result<EnvDescriptor, AnyError> {
+    ) -> Result<EnvDescriptor, EnvDescriptorParseError> {
       Ok(EnvDescriptor::new(text))
     }
 
     fn parse_sys_descriptor(
       &self,
       text: &str,
-    ) -> Result<SysDescriptor, AnyError> {
-      Ok(SysDescriptor(text.to_string()))
+    ) -> Result<SysDescriptor, SysDescriptorParseError> {
+      SysDescriptor::parse(text.to_string())
     }
 
     fn parse_allow_run_descriptor(
       &self,
       text: &str,
-    ) -> Result<AllowRunDescriptorParseResult, AnyError> {
+    ) -> Result<AllowRunDescriptorParseResult, RunDescriptorParseError> {
       Ok(AllowRunDescriptorParseResult::Descriptor(
         AllowRunDescriptor(self.join_path_with_root(text)),
       ))
@@ -3085,7 +3643,7 @@ mod tests {
     fn parse_deny_run_descriptor(
       &self,
       text: &str,
-    ) -> Result<DenyRunDescriptor, AnyError> {
+    ) -> Result<DenyRunDescriptor, PathResolveError> {
       if text.contains("/") {
         Ok(DenyRunDescriptor::Path(self.join_path_with_root(text)))
       } else {
@@ -3096,14 +3654,14 @@ mod tests {
     fn parse_ffi_descriptor(
       &self,
       text: &str,
-    ) -> Result<FfiDescriptor, AnyError> {
+    ) -> Result<FfiDescriptor, PathResolveError> {
       Ok(FfiDescriptor(self.join_path_with_root(text)))
     }
 
     fn parse_path_query(
       &self,
       path: &str,
-    ) -> Result<PathQueryDescriptor, AnyError> {
+    ) -> Result<PathQueryDescriptor, PathResolveError> {
       Ok(PathQueryDescriptor {
         resolved: self.join_path_with_root(path),
         requested: path.to_string(),
@@ -3113,8 +3671,8 @@ mod tests {
     fn parse_run_query(
       &self,
       requested: &str,
-    ) -> Result<RunQueryDescriptor, AnyError> {
-      RunQueryDescriptor::parse(requested)
+    ) -> Result<RunQueryDescriptor, RunDescriptorParseError> {
+      RunQueryDescriptor::parse(requested).map_err(Into::into)
     }
   }
 
@@ -3579,15 +4137,16 @@ mod tests {
       assert_eq!(perms4.env.query(None), PermissionState::GrantedPartial);
       assert_eq!(perms4.env.query(Some("HOME")), PermissionState::Denied);
       assert_eq!(perms4.env.query(Some("AWAY")), PermissionState::Granted);
+      let sys_desc = |name: &str| SysDescriptor::parse(name.to_string()).unwrap();
       assert_eq!(perms1.sys.query(None), PermissionState::Granted);
-      assert_eq!(perms1.sys.query(Some("HOME")), PermissionState::Granted);
+      assert_eq!(perms1.sys.query(Some(&sys_desc("osRelease"))), PermissionState::Granted);
       assert_eq!(perms2.sys.query(None), PermissionState::Prompt);
-      assert_eq!(perms2.sys.query(Some("hostname")), PermissionState::Granted);
+      assert_eq!(perms2.sys.query(Some(&sys_desc("hostname"))), PermissionState::Granted);
       assert_eq!(perms3.sys.query(None), PermissionState::Prompt);
-      assert_eq!(perms3.sys.query(Some("hostname")), PermissionState::Denied);
+      assert_eq!(perms3.sys.query(Some(&sys_desc("hostname"))), PermissionState::Denied);
       assert_eq!(perms4.sys.query(None), PermissionState::GrantedPartial);
-      assert_eq!(perms4.sys.query(Some("hostname")), PermissionState::Denied);
-      assert_eq!(perms4.sys.query(Some("uid")), PermissionState::Granted);
+      assert_eq!(perms4.sys.query(Some(&sys_desc("hostname"))), PermissionState::Denied);
+      assert_eq!(perms4.sys.query(Some(&sys_desc("uid"))), PermissionState::Granted);
       assert_eq!(perms1.run.query(None), PermissionState::Granted);
       let deno_run_query = RunQueryDescriptor::Path {
         requested: "deno".to_string(),
@@ -3614,7 +4173,8 @@ mod tests {
   fn test_request() {
     set_prompter(Box::new(TestPrompter));
     let parser = TestPermissionDescriptorParser;
-    let mut perms: Permissions = Permissions::none_without_prompt();
+    let mut perms: Permissions = Permissions::none_with_prompt();
+    let mut perms_no_prompt: Permissions = Permissions::none_without_prompt();
     let read_query =
       |path: &str| parser.parse_path_query(path).unwrap().into_read();
     let write_query =
@@ -3649,10 +4209,11 @@ mod tests {
       prompt_value.set(false);
       assert_eq!(perms.env.request(Some("HOME")), PermissionState::Granted);
       prompt_value.set(true);
-      assert_eq!(perms.sys.request(Some("hostname")), PermissionState::Granted);
+      let sys_desc = |name: &str| SysDescriptor::parse(name.to_string()).unwrap();
+      assert_eq!(perms.sys.request(Some(&sys_desc("hostname"))), PermissionState::Granted);
       assert_eq!(perms.sys.query(None), PermissionState::Prompt);
       prompt_value.set(false);
-      assert_eq!(perms.sys.request(Some("hostname")), PermissionState::Granted);
+      assert_eq!(perms.sys.request(Some(&sys_desc("hostname"))), PermissionState::Granted);
       prompt_value.set(true);
       let run_query = RunQueryDescriptor::Path {
         requested: "deno".to_string(),
@@ -3662,6 +4223,7 @@ mod tests {
       assert_eq!(perms.run.query(None), PermissionState::Prompt);
       prompt_value.set(false);
       assert_eq!(perms.run.request(Some(&run_query)), PermissionState::Granted);
+      assert_eq!(perms_no_prompt.read.request(Some(&read_query("/foo"))), PermissionState::Denied);
     };
   }
 
@@ -3969,12 +4531,13 @@ mod tests {
     assert!(perms.env.check("PATH", None).is_ok());
 
     prompt_value.set(false);
-    assert!(perms.sys.check("hostname", None).is_err());
+    let sys_desc = |name: &str| SysDescriptor::parse(name.to_string()).unwrap();
+    assert!(perms.sys.check(&sys_desc("hostname"), None).is_err());
     prompt_value.set(true);
-    assert!(perms.sys.check("hostname", None).is_err());
-    assert!(perms.sys.check("osRelease", None).is_ok());
+    assert!(perms.sys.check(&sys_desc("hostname"), None).is_err());
+    assert!(perms.sys.check(&sys_desc("osRelease"), None).is_ok());
     prompt_value.set(false);
-    assert!(perms.sys.check("osRelease", None).is_ok());
+    assert!(perms.sys.check(&sys_desc("osRelease"), None).is_ok());
   }
 
   #[test]
@@ -3990,7 +4553,6 @@ mod tests {
         None,
         false,
       )
-      .unwrap()
     };
 
     prompt_value.set(true);
@@ -4194,7 +4756,7 @@ mod tests {
   fn test_create_child_permissions() {
     set_prompter(Box::new(TestPrompter));
     let parser = TestPermissionDescriptorParser;
-    let mut main_perms = Permissions::from_options(
+    let main_perms = Permissions::from_options(
       &parser,
       &PermissionsOptions {
         allow_env: Some(vec![]),
@@ -4203,63 +4765,54 @@ mod tests {
       },
     )
     .unwrap();
+    let main_perms = PermissionsContainer::new(Arc::new(parser), main_perms);
     assert_eq!(
-      create_child_permissions(
-        &parser,
-        &mut main_perms.clone(),
-        ChildPermissionsArg {
+      main_perms
+        .create_child_permissions(ChildPermissionsArg {
           env: ChildUnaryPermissionArg::Inherit,
           net: ChildUnaryPermissionArg::GrantedList(svec!["foo"]),
           ffi: ChildUnaryPermissionArg::NotGranted,
           ..ChildPermissionsArg::none()
-        }
-      )
-      .unwrap(),
+        })
+        .unwrap()
+        .inner
+        .lock()
+        .clone(),
       Permissions {
-        env: Permissions::new_unary(Some(HashSet::new()), None, false).unwrap(),
+        env: Permissions::new_unary(Some(HashSet::new()), None, false),
         net: Permissions::new_unary(
           Some(HashSet::from([NetDescriptor::parse("foo").unwrap()])),
           None,
           false
-        )
-        .unwrap(),
+        ),
         ..Permissions::none_without_prompt()
       }
     );
-    assert!(create_child_permissions(
-      &parser,
-      &mut main_perms.clone(),
-      ChildPermissionsArg {
+    assert!(main_perms
+      .create_child_permissions(ChildPermissionsArg {
         net: ChildUnaryPermissionArg::Granted,
         ..ChildPermissionsArg::none()
-      }
-    )
-    .is_err());
-    assert!(create_child_permissions(
-      &parser,
-      &mut main_perms.clone(),
-      ChildPermissionsArg {
+      })
+      .is_err());
+    assert!(main_perms
+      .create_child_permissions(ChildPermissionsArg {
         net: ChildUnaryPermissionArg::GrantedList(svec!["foo", "bar", "baz"]),
         ..ChildPermissionsArg::none()
-      }
-    )
-    .is_err());
-    assert!(create_child_permissions(
-      &parser,
-      &mut main_perms,
-      ChildPermissionsArg {
+      })
+      .is_err());
+    assert!(main_perms
+      .create_child_permissions(ChildPermissionsArg {
         ffi: ChildUnaryPermissionArg::GrantedList(svec!["foo"]),
         ..ChildPermissionsArg::none()
-      }
-    )
-    .is_err());
+      })
+      .is_err());
   }
 
   #[test]
   fn test_create_child_permissions_with_prompt() {
     set_prompter(Box::new(TestPrompter));
     let prompt_value = PERMISSION_PROMPT_STUB_VALUE_SETTER.lock();
-    let mut main_perms = Permissions::from_options(
+    let main_perms = Permissions::from_options(
       &TestPermissionDescriptorParser,
       &PermissionsOptions {
         prompt: true,
@@ -4267,20 +4820,24 @@ mod tests {
       },
     )
     .unwrap();
+    let main_perms = PermissionsContainer::new(
+      Arc::new(TestPermissionDescriptorParser),
+      main_perms,
+    );
     prompt_value.set(true);
-    let worker_perms = create_child_permissions(
-      &TestPermissionDescriptorParser,
-      &mut main_perms,
-      ChildPermissionsArg {
+    let worker_perms = main_perms
+      .create_child_permissions(ChildPermissionsArg {
         read: ChildUnaryPermissionArg::Granted,
         run: ChildUnaryPermissionArg::GrantedList(svec!["foo", "bar"]),
         ..ChildPermissionsArg::none()
-      },
-    )
-    .unwrap();
-    assert_eq!(main_perms, worker_perms);
+      })
+      .unwrap();
     assert_eq!(
-      main_perms.run.granted_list,
+      main_perms.inner.lock().clone(),
+      worker_perms.inner.lock().clone()
+    );
+    assert_eq!(
+      main_perms.inner.lock().run.granted_list,
       HashSet::from([
         AllowRunDescriptor(PathBuf::from("/bar")),
         AllowRunDescriptor(PathBuf::from("/foo")),
@@ -4293,7 +4850,7 @@ mod tests {
     set_prompter(Box::new(TestPrompter));
     let prompt_value = PERMISSION_PROMPT_STUB_VALUE_SETTER.lock();
     let parser = TestPermissionDescriptorParser;
-    let mut main_perms = Permissions::from_options(
+    let main_perms = Permissions::from_options(
       &parser,
       &PermissionsOptions {
         prompt: true,
@@ -4301,20 +4858,21 @@ mod tests {
       },
     )
     .unwrap();
+    let main_perms =
+      PermissionsContainer::new(Arc::new(parser.clone()), main_perms);
     prompt_value.set(false);
     assert!(main_perms
+      .inner
+      .lock()
       .write
       .check(&parser.parse_path_query("foo").unwrap().into_write(), None)
       .is_err());
-    let worker_perms = create_child_permissions(
-      &TestPermissionDescriptorParser,
-      &mut main_perms.clone(),
-      ChildPermissionsArg::none(),
-    )
-    .unwrap();
+    let worker_perms = main_perms
+      .create_child_permissions(ChildPermissionsArg::none())
+      .unwrap();
     assert_eq!(
-      worker_perms.write.flag_denied_list,
-      main_perms.write.flag_denied_list
+      worker_perms.inner.lock().write.flag_denied_list.clone(),
+      main_perms.inner.lock().write.flag_denied_list
     );
   }
 
@@ -4453,38 +5011,4 @@ mod tests {
       );
     }
   }
-
-  #[test]
-  fn test_specifier_to_file_path() {
-    run_success_test("file:///", "/");
-    run_success_test("file:///test", "/test");
-    run_success_test("file:///dir/test/test.txt", "/dir/test/test.txt");
-    run_success_test(
-      "file:///dir/test%20test/test.txt",
-      "/dir/test test/test.txt",
-    );
-
-    assert_no_panic_specifier_to_file_path("file:/");
-    assert_no_panic_specifier_to_file_path("file://");
-    assert_no_panic_specifier_to_file_path("file://asdf/");
-    assert_no_panic_specifier_to_file_path("file://asdf/66666/a.ts");
-
-    fn run_success_test(specifier: &str, expected_path: &str) {
-      let result =
-        specifier_to_file_path(&ModuleSpecifier::parse(specifier).unwrap())
-          .unwrap();
-      assert_eq!(result, PathBuf::from(expected_path));
-    }
-    fn assert_no_panic_specifier_to_file_path(specifier: &str) {
-      let result =
-        specifier_to_file_path(&ModuleSpecifier::parse(specifier).unwrap());
-      match result {
-        Ok(_) => (),
-        Err(err) => assert_eq!(
-          err.to_string(),
-          format!("Invalid file path.\n  Specifier: {specifier}")
-        ),
-      }
-    }
-  }
 }
diff --git a/runtime/permissions/prompter.rs b/runtime/permissions/prompter.rs
index e48e0af10d..168a845a29 100644
--- a/runtime/permissions/prompter.rs
+++ b/runtime/permissions/prompter.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::parking_lot::Mutex;
 use deno_terminal::colors;
 use once_cell::sync::Lazy;
@@ -80,6 +79,10 @@ pub fn set_prompt_callbacks(
   *MAYBE_AFTER_PROMPT_CALLBACK.lock() = Some(after_callback);
 }
 
+pub fn set_prompter(prompter: Box<dyn PermissionPrompter>) {
+  *PERMISSION_PROMPTER.lock() = prompter;
+}
+
 pub type PromptCallback = Box<dyn FnMut() + Send + Sync>;
 
 pub trait PermissionPrompter: Send + Sync {
@@ -97,8 +100,7 @@ pub struct TtyPrompter;
 fn clear_stdin(
   _stdin_lock: &mut StdinLock,
   _stderr_lock: &mut StderrLock,
-) -> Result<(), AnyError> {
-  use deno_core::anyhow::bail;
+) -> Result<(), std::io::Error> {
   use std::mem::MaybeUninit;
 
   const STDIN_FD: i32 = 0;
@@ -113,7 +115,10 @@ fn clear_stdin(
     loop {
       let r = libc::tcflush(STDIN_FD, libc::TCIFLUSH);
       if r != 0 {
-        bail!("clear_stdin failed (tcflush)");
+        return Err(std::io::Error::new(
+          std::io::ErrorKind::Other,
+          "clear_stdin failed (tcflush)",
+        ));
       }
 
       // Initialize timeout for select to be 100ms
@@ -133,7 +138,10 @@ fn clear_stdin(
 
       // Check if select returned an error
       if r < 0 {
-        bail!("clear_stdin failed (select)");
+        return Err(std::io::Error::new(
+          std::io::ErrorKind::Other,
+          "clear_stdin failed (select)",
+        ));
       }
 
       // Check if select returned due to timeout (stdin is quiescent)
@@ -152,8 +160,7 @@ fn clear_stdin(
 fn clear_stdin(
   stdin_lock: &mut StdinLock,
   stderr_lock: &mut StderrLock,
-) -> Result<(), AnyError> {
-  use deno_core::anyhow::bail;
+) -> Result<(), std::io::Error> {
   use winapi::shared::minwindef::TRUE;
   use winapi::shared::minwindef::UINT;
   use winapi::shared::minwindef::WORD;
@@ -190,18 +197,23 @@ fn clear_stdin(
 
   return Ok(());
 
-  unsafe fn flush_input_buffer(stdin: HANDLE) -> Result<(), AnyError> {
+  unsafe fn flush_input_buffer(stdin: HANDLE) -> Result<(), std::io::Error> {
     let success = FlushConsoleInputBuffer(stdin);
     if success != TRUE {
-      bail!(
-        "Could not flush the console input buffer: {}",
-        std::io::Error::last_os_error()
-      )
+      return Err(std::io::Error::new(
+        std::io::ErrorKind::Other,
+        format!(
+          "Could not flush the console input buffer: {}",
+          std::io::Error::last_os_error()
+        ),
+      ));
     }
     Ok(())
   }
 
-  unsafe fn emulate_enter_key_press(stdin: HANDLE) -> Result<(), AnyError> {
+  unsafe fn emulate_enter_key_press(
+    stdin: HANDLE,
+  ) -> Result<(), std::io::Error> {
     // https://github.com/libuv/libuv/blob/a39009a5a9252a566ca0704d02df8dabc4ce328f/src/win/tty.c#L1121-L1131
     let mut input_record: INPUT_RECORD = std::mem::zeroed();
     input_record.EventType = KEY_EVENT;
@@ -216,34 +228,43 @@ fn clear_stdin(
     let success =
       WriteConsoleInputW(stdin, &input_record, 1, &mut record_written);
     if success != TRUE {
-      bail!(
-        "Could not emulate enter key press: {}",
-        std::io::Error::last_os_error()
-      );
+      return Err(std::io::Error::new(
+        std::io::ErrorKind::Other,
+        format!(
+          "Could not emulate enter key press: {}",
+          std::io::Error::last_os_error()
+        ),
+      ));
     }
     Ok(())
   }
 
-  unsafe fn is_input_buffer_empty(stdin: HANDLE) -> Result<bool, AnyError> {
+  unsafe fn is_input_buffer_empty(
+    stdin: HANDLE,
+  ) -> Result<bool, std::io::Error> {
     let mut buffer = Vec::with_capacity(1);
     let mut events_read = 0;
     let success =
       PeekConsoleInputW(stdin, buffer.as_mut_ptr(), 1, &mut events_read);
     if success != TRUE {
-      bail!(
-        "Could not peek the console input buffer: {}",
-        std::io::Error::last_os_error()
-      )
+      return Err(std::io::Error::new(
+        std::io::ErrorKind::Other,
+        format!(
+          "Could not peek the console input buffer: {}",
+          std::io::Error::last_os_error()
+        ),
+      ));
     }
     Ok(events_read == 0)
   }
 
-  fn move_cursor_up(stderr_lock: &mut StderrLock) -> Result<(), AnyError> {
-    write!(stderr_lock, "\x1B[1A")?;
-    Ok(())
+  fn move_cursor_up(
+    stderr_lock: &mut StderrLock,
+  ) -> Result<(), std::io::Error> {
+    write!(stderr_lock, "\x1B[1A")
   }
 
-  fn read_stdin_line(stdin_lock: &mut StdinLock) -> Result<(), AnyError> {
+  fn read_stdin_line(stdin_lock: &mut StdinLock) -> Result<(), std::io::Error> {
     let mut input = String::new();
     stdin_lock.read_line(&mut input)?;
     Ok(())
@@ -265,7 +286,7 @@ fn get_stdin_metadata() -> std::io::Result<std::fs::Metadata> {
   unsafe {
     let stdin = std::fs::File::from_raw_fd(0);
     let metadata = stdin.metadata().unwrap();
-    stdin.into_raw_fd();
+    let _ = stdin.into_raw_fd();
     Ok(metadata)
   }
 }
@@ -366,7 +387,7 @@ impl PermissionPrompter for TtyPrompter {
 
       let mut input = String::new();
       let result = stdin_lock.read_line(&mut input);
-      let input = input.trim_end_matches(|c| c == '\r' || c == '\n');
+      let input = input.trim_end_matches(['\r', '\n']);
       if result.is_err() || input.len() != 1 {
         break PromptResponse::Deny;
       };
@@ -476,8 +497,4 @@ pub mod tests {
       STUB_PROMPT_VALUE.store(value, Ordering::SeqCst);
     }
   }
-
-  pub fn set_prompter(prompter: Box<dyn PermissionPrompter>) {
-    *PERMISSION_PROMPTER.lock() = prompter;
-  }
 }
diff --git a/runtime/shared.rs b/runtime/shared.rs
index 02dfd18719..c05f352f1c 100644
--- a/runtime/shared.rs
+++ b/runtime/shared.rs
@@ -47,6 +47,7 @@ extension!(runtime,
     "40_signals.js",
     "40_tty.js",
     "41_prompt.js",
+    "telemetry.js",
     "90_deno_ns.js",
     "98_global_scope_shared.js",
     "98_global_scope_window.js",
@@ -98,6 +99,7 @@ pub fn maybe_transpile_source(
         imports_not_used_as_values: deno_ast::ImportsNotUsedAsValues::Remove,
         ..Default::default()
       },
+      &deno_ast::TranspileModuleOptions::default(),
       &deno_ast::EmitOptions {
         source_map: if cfg!(debug_assertions) {
           SourceMapOption::Separate
@@ -109,9 +111,9 @@ pub fn maybe_transpile_source(
     )?
     .into_source();
 
-  let maybe_source_map: Option<SourceMapData> =
-    transpiled_source.source_map.map(|sm| sm.into());
-  let source_text = String::from_utf8(transpiled_source.source)?;
-
+  let maybe_source_map: Option<SourceMapData> = transpiled_source
+    .source_map
+    .map(|sm| sm.into_bytes().into());
+  let source_text = transpiled_source.text;
   Ok((source_text.into(), maybe_source_map))
 }
diff --git a/runtime/snapshot.rs b/runtime/snapshot.rs
index f20c04f082..7f6e6b8ab6 100644
--- a/runtime/snapshot.rs
+++ b/runtime/snapshot.rs
@@ -2,16 +2,15 @@
 
 use crate::ops;
 use crate::ops::bootstrap::SnapshotOptions;
-use crate::permissions::RuntimePermissionDescriptorParser;
 use crate::shared::maybe_transpile_source;
 use crate::shared::runtime;
 use deno_cache::SqliteBackedCache;
-use deno_core::error::AnyError;
 use deno_core::snapshot::*;
 use deno_core::v8;
 use deno_core::Extension;
 use deno_http::DefaultHttpPropertyExtractor;
 use deno_io::fs::FsError;
+use deno_permissions::PermissionCheckError;
 use std::borrow::Cow;
 use std::io::Write;
 use std::path::Path;
@@ -27,7 +26,7 @@ impl deno_websocket::WebSocketPermissions for Permissions {
     &mut self,
     _url: &deno_core::url::Url,
     _api_name: &str,
-  ) -> Result<(), deno_core::error::AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 }
@@ -43,7 +42,7 @@ impl deno_fetch::FetchPermissions for Permissions {
     &mut self,
     _url: &deno_core::url::Url,
     _api_name: &str,
-  ) -> Result<(), deno_core::error::AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 
@@ -51,28 +50,26 @@ impl deno_fetch::FetchPermissions for Permissions {
     &mut self,
     _p: &'a Path,
     _api_name: &str,
-  ) -> Result<Cow<'a, Path>, AnyError> {
+  ) -> Result<Cow<'a, Path>, PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 }
 
 impl deno_ffi::FfiPermissions for Permissions {
-  fn check_partial_no_path(
-    &mut self,
-  ) -> Result<(), deno_core::error::AnyError> {
+  fn check_partial_no_path(&mut self) -> Result<(), PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 
   fn check_partial_with_path(
     &mut self,
     _path: &str,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 }
 
 impl deno_napi::NapiPermissions for Permissions {
-  fn check(&mut self, _path: &str) -> std::result::Result<PathBuf, AnyError> {
+  fn check(&mut self, _path: &str) -> Result<PathBuf, PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 }
@@ -82,34 +79,44 @@ impl deno_node::NodePermissions for Permissions {
     &mut self,
     _url: &deno_core::url::Url,
     _api_name: &str,
-  ) -> Result<(), deno_core::error::AnyError> {
+  ) -> Result<(), PermissionCheckError> {
+    unreachable!("snapshotting!")
+  }
+  fn check_net(
+    &mut self,
+    _host: (&str, Option<u16>),
+    _api_name: &str,
+  ) -> Result<(), PermissionCheckError> {
     unreachable!("snapshotting!")
   }
   fn check_read_path<'a>(
     &mut self,
     _path: &'a Path,
-  ) -> Result<Cow<'a, Path>, AnyError> {
+  ) -> Result<Cow<'a, Path>, PermissionCheckError> {
     unreachable!("snapshotting!")
   }
   fn check_read_with_api_name(
     &mut self,
     _p: &str,
     _api_name: Option<&str>,
-  ) -> Result<PathBuf, deno_core::error::AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
+    unreachable!("snapshotting!")
+  }
+  fn query_read_all(&mut self) -> bool {
     unreachable!("snapshotting!")
   }
   fn check_write_with_api_name(
     &mut self,
     _p: &str,
     _api_name: Option<&str>,
-  ) -> Result<PathBuf, deno_core::error::AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     unreachable!("snapshotting!")
   }
   fn check_sys(
     &mut self,
     _kind: &str,
     _api_name: &str,
-  ) -> Result<(), deno_core::error::AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 }
@@ -119,7 +126,7 @@ impl deno_net::NetPermissions for Permissions {
     &mut self,
     _host: &(T, Option<u16>),
     _api_name: &str,
-  ) -> Result<(), deno_core::error::AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 
@@ -127,7 +134,7 @@ impl deno_net::NetPermissions for Permissions {
     &mut self,
     _p: &str,
     _api_name: &str,
-  ) -> Result<PathBuf, deno_core::error::AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 
@@ -135,7 +142,7 @@ impl deno_net::NetPermissions for Permissions {
     &mut self,
     _p: &str,
     _api_name: &str,
-  ) -> Result<PathBuf, deno_core::error::AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 
@@ -143,7 +150,7 @@ impl deno_net::NetPermissions for Permissions {
     &mut self,
     _p: &'a Path,
     _api_name: &str,
-  ) -> Result<std::borrow::Cow<'a, Path>, AnyError> {
+  ) -> Result<Cow<'a, Path>, PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 }
@@ -156,7 +163,7 @@ impl deno_fs::FsPermissions for Permissions {
     _write: bool,
     _path: &'a Path,
     _api_name: &str,
-  ) -> Result<std::borrow::Cow<'a, Path>, FsError> {
+  ) -> Result<Cow<'a, Path>, FsError> {
     unreachable!("snapshotting!")
   }
 
@@ -164,11 +171,14 @@ impl deno_fs::FsPermissions for Permissions {
     &mut self,
     _path: &str,
     _api_name: &str,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 
-  fn check_read_all(&mut self, _api_name: &str) -> Result<(), AnyError> {
+  fn check_read_all(
+    &mut self,
+    _api_name: &str,
+  ) -> Result<(), PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 
@@ -177,7 +187,7 @@ impl deno_fs::FsPermissions for Permissions {
     _path: &Path,
     _display: &str,
     _api_name: &str,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 
@@ -185,7 +195,7 @@ impl deno_fs::FsPermissions for Permissions {
     &mut self,
     _path: &str,
     _api_name: &str,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 
@@ -193,11 +203,14 @@ impl deno_fs::FsPermissions for Permissions {
     &mut self,
     _path: &str,
     _api_name: &str,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 
-  fn check_write_all(&mut self, _api_name: &str) -> Result<(), AnyError> {
+  fn check_write_all(
+    &mut self,
+    _api_name: &str,
+  ) -> Result<(), PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 
@@ -206,7 +219,7 @@ impl deno_fs::FsPermissions for Permissions {
     _path: &Path,
     _display: &str,
     _api_name: &str,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 
@@ -214,7 +227,7 @@ impl deno_fs::FsPermissions for Permissions {
     &mut self,
     _path: &'a Path,
     _api_name: &str,
-  ) -> Result<std::borrow::Cow<'a, Path>, AnyError> {
+  ) -> Result<Cow<'a, Path>, PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 
@@ -222,7 +235,7 @@ impl deno_fs::FsPermissions for Permissions {
     &mut self,
     _path: &'a Path,
     _api_name: &str,
-  ) -> Result<std::borrow::Cow<'a, Path>, AnyError> {
+  ) -> Result<Cow<'a, Path>, PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 }
@@ -232,7 +245,7 @@ impl deno_kv::sqlite::SqliteDbHandlerPermissions for Permissions {
     &mut self,
     _path: &str,
     _api_name: &str,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 
@@ -240,7 +253,7 @@ impl deno_kv::sqlite::SqliteDbHandlerPermissions for Permissions {
     &mut self,
     _path: &'a Path,
     _api_name: &str,
-  ) -> Result<Cow<'a, Path>, AnyError> {
+  ) -> Result<Cow<'a, Path>, PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 }
@@ -299,9 +312,8 @@ pub fn create_runtime_snapshot(
     ),
     ops::fs_events::deno_fs_events::init_ops(),
     ops::os::deno_os::init_ops(Default::default()),
-    ops::permissions::deno_permissions::init_ops(Arc::new(
-      RuntimePermissionDescriptorParser::new(fs),
-    )),
+    ops::otel::deno_otel::init_ops(),
+    ops::permissions::deno_permissions::init_ops(),
     ops::process::deno_process::init_ops(None),
     ops::signal::deno_signal::init_ops(),
     ops::tty::deno_tty::init_ops(),
diff --git a/runtime/ops/os/sys_info.rs b/runtime/sys_info.rs
similarity index 100%
rename from runtime/ops/os/sys_info.rs
rename to runtime/sys_info.rs
diff --git a/runtime/tokio_util.rs b/runtime/tokio_util.rs
index 0d81f6e235..aa0282ece8 100644
--- a/runtime/tokio_util.rs
+++ b/runtime/tokio_util.rs
@@ -43,7 +43,15 @@ pub fn create_basic_runtime() -> tokio::runtime::Runtime {
     // parallel for deno fmt.
     // The default value is 512, which is an unhelpfully large thread pool. We
     // don't ever want to have more than a couple dozen threads.
-    .max_blocking_threads(32)
+    .max_blocking_threads(if cfg!(windows) {
+      // on windows, tokio uses blocking tasks for child process IO, make sure
+      // we have enough available threads for other tasks to run
+      4 * std::thread::available_parallelism()
+        .map(|n| n.get())
+        .unwrap_or(8)
+    } else {
+      32
+    })
     .build()
     .unwrap()
 }
diff --git a/runtime/web_worker.rs b/runtime/web_worker.rs
index 8892d5bc6e..8e0c870d1a 100644
--- a/runtime/web_worker.rs
+++ b/runtime/web_worker.rs
@@ -1,16 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-use crate::inspector_server::InspectorServer;
-use crate::ops;
-use crate::ops::process::NpmProcessStateProviderRc;
-use crate::ops::worker_host::WorkersTable;
-use crate::shared::maybe_transpile_source;
-use crate::shared::runtime;
-use crate::tokio_util::create_and_run_current_thread;
-use crate::worker::create_op_metrics;
-use crate::worker::import_meta_resolve_callback;
-use crate::worker::validate_import_attributes_callback;
-use crate::worker::FormatJsErrorFn;
-use crate::BootstrapOptions;
+
 use deno_broadcast_channel::InMemoryBroadcastChannel;
 use deno_cache::CreateCache;
 use deno_cache::SqliteBackedCache;
@@ -45,7 +34,6 @@ use deno_http::DefaultHttpPropertyExtractor;
 use deno_io::Stdio;
 use deno_kv::dynamic::MultiBackendDbHandler;
 use deno_node::NodeExtInitServices;
-use deno_permissions::PermissionDescriptorParser;
 use deno_permissions::PermissionsContainer;
 use deno_terminal::colors;
 use deno_tls::RootCertStoreProvider;
@@ -67,6 +55,19 @@ use std::sync::Arc;
 use std::task::Context;
 use std::task::Poll;
 
+use crate::inspector_server::InspectorServer;
+use crate::ops;
+use crate::ops::process::NpmProcessStateProviderRc;
+use crate::ops::worker_host::WorkersTable;
+use crate::shared::maybe_transpile_source;
+use crate::shared::runtime;
+use crate::tokio_util::create_and_run_current_thread;
+use crate::worker::create_op_metrics;
+use crate::worker::import_meta_resolve_callback;
+use crate::worker::validate_import_attributes_callback;
+use crate::worker::FormatJsErrorFn;
+use crate::BootstrapOptions;
+
 pub struct WorkerMetadata {
   pub buffer: DetachedBuffer,
   pub transferables: Vec<Transferable>,
@@ -165,7 +166,10 @@ pub struct WebWorkerInternalHandle {
 
 impl WebWorkerInternalHandle {
   /// Post WorkerEvent to parent as a worker
-  pub fn post_event(&self, event: WorkerControlEvent) -> Result<(), AnyError> {
+  pub fn post_event(
+    &self,
+    event: WorkerControlEvent,
+  ) -> Result<(), mpsc::TrySendError<WorkerControlEvent>> {
     let mut sender = self.sender.clone();
     // If the channel is closed,
     // the worker must have terminated but the termination message has not yet been received.
@@ -175,8 +179,7 @@ impl WebWorkerInternalHandle {
       self.has_terminated.store(true, Ordering::SeqCst);
       return Ok(());
     }
-    sender.try_send(event)?;
-    Ok(())
+    sender.try_send(event)
   }
 
   /// Check if this worker is terminated or being terminated
@@ -262,11 +265,9 @@ impl WebWorkerHandle {
   /// Get the WorkerEvent with lock
   /// Return error if more than one listener tries to get event
   #[allow(clippy::await_holding_refcell_ref)] // TODO(ry) remove!
-  pub async fn get_control_event(
-    &self,
-  ) -> Result<Option<WorkerControlEvent>, AnyError> {
+  pub async fn get_control_event(&self) -> Option<WorkerControlEvent> {
     let mut receiver = self.receiver.borrow_mut();
-    Ok(receiver.next().await)
+    receiver.next().await
   }
 
   /// Terminate the worker
@@ -337,6 +338,43 @@ fn create_handles(
   (internal_handle, external_handle)
 }
 
+pub struct WebWorkerServiceOptions {
+  pub blob_store: Arc<BlobStore>,
+  pub broadcast_channel: InMemoryBroadcastChannel,
+  pub compiled_wasm_module_store: Option<CompiledWasmModuleStore>,
+  pub feature_checker: Arc<FeatureChecker>,
+  pub fs: Arc<dyn FileSystem>,
+  pub maybe_inspector_server: Option<Arc<InspectorServer>>,
+  pub module_loader: Rc<dyn ModuleLoader>,
+  pub node_services: Option<NodeExtInitServices>,
+  pub npm_process_state_provider: Option<NpmProcessStateProviderRc>,
+  pub permissions: PermissionsContainer,
+  pub root_cert_store_provider: Option<Arc<dyn RootCertStoreProvider>>,
+  pub shared_array_buffer_store: Option<SharedArrayBufferStore>,
+}
+
+pub struct WebWorkerOptions {
+  pub name: String,
+  pub main_module: ModuleSpecifier,
+  pub worker_id: WorkerId,
+  pub bootstrap: BootstrapOptions,
+  pub extensions: Vec<Extension>,
+  pub startup_snapshot: Option<&'static [u8]>,
+  pub unsafely_ignore_certificate_errors: Option<Vec<String>>,
+  /// Optional isolate creation parameters, such as heap limits.
+  pub create_params: Option<v8::CreateParams>,
+  pub seed: Option<u64>,
+  pub create_web_worker_cb: Arc<ops::worker_host::CreateWebWorkerCb>,
+  pub format_js_error_fn: Option<Arc<FormatJsErrorFn>>,
+  pub worker_type: WebWorkerType,
+  pub get_error_class_fn: Option<GetErrorClassFn>,
+  pub cache_storage_dir: Option<std::path::PathBuf>,
+  pub stdio: Stdio,
+  pub strace_ops: Option<Vec<String>>,
+  pub close_on_idle: bool,
+  pub maybe_worker_metadata: Option<WorkerMetadata>,
+}
+
 /// This struct is an implementation of `Worker` Web API
 ///
 /// Each `WebWorker` is either a child of `MainWorker` or other
@@ -357,58 +395,28 @@ pub struct WebWorker {
   maybe_worker_metadata: Option<WorkerMetadata>,
 }
 
-pub struct WebWorkerOptions {
-  // todo(dsherret): extract out the service structs from this options bag
-  pub bootstrap: BootstrapOptions,
-  pub extensions: Vec<Extension>,
-  pub startup_snapshot: Option<&'static [u8]>,
-  pub unsafely_ignore_certificate_errors: Option<Vec<String>>,
-  pub root_cert_store_provider: Option<Arc<dyn RootCertStoreProvider>>,
-  pub seed: Option<u64>,
-  pub fs: Arc<dyn FileSystem>,
-  pub module_loader: Rc<dyn ModuleLoader>,
-  pub node_services: Option<NodeExtInitServices>,
-  pub create_web_worker_cb: Arc<ops::worker_host::CreateWebWorkerCb>,
-  pub format_js_error_fn: Option<Arc<FormatJsErrorFn>>,
-  pub worker_type: WebWorkerType,
-  pub maybe_inspector_server: Option<Arc<InspectorServer>>,
-  pub get_error_class_fn: Option<GetErrorClassFn>,
-  pub blob_store: Arc<BlobStore>,
-  pub broadcast_channel: InMemoryBroadcastChannel,
-  pub shared_array_buffer_store: Option<SharedArrayBufferStore>,
-  pub compiled_wasm_module_store: Option<CompiledWasmModuleStore>,
-  pub cache_storage_dir: Option<std::path::PathBuf>,
-  pub stdio: Stdio,
-  pub feature_checker: Arc<FeatureChecker>,
-  pub permission_desc_parser: Arc<dyn PermissionDescriptorParser>,
-  pub strace_ops: Option<Vec<String>>,
-  pub close_on_idle: bool,
-  pub maybe_worker_metadata: Option<WorkerMetadata>,
-  pub npm_process_state_provider: Option<NpmProcessStateProviderRc>,
+impl Drop for WebWorker {
+  fn drop(&mut self) {
+    // clean up the package.json thread local cache
+    node_resolver::PackageJsonThreadLocalCache::clear();
+  }
 }
 
 impl WebWorker {
   pub fn bootstrap_from_options(
-    name: String,
-    permissions: PermissionsContainer,
-    main_module: ModuleSpecifier,
-    worker_id: WorkerId,
+    services: WebWorkerServiceOptions,
     options: WebWorkerOptions,
   ) -> (Self, SendableWebWorkerHandle) {
-    let bootstrap_options = options.bootstrap.clone();
-    let (mut worker, handle) =
-      Self::from_options(name, permissions, main_module, worker_id, options);
+    let (mut worker, handle, bootstrap_options) =
+      Self::from_options(services, options);
     worker.bootstrap(&bootstrap_options);
     (worker, handle)
   }
 
-  pub fn from_options(
-    name: String,
-    permissions: PermissionsContainer,
-    main_module: ModuleSpecifier,
-    worker_id: WorkerId,
+  fn from_options(
+    services: WebWorkerServiceOptions,
     mut options: WebWorkerOptions,
-  ) -> (Self, SendableWebWorkerHandle) {
+  ) -> (Self, SendableWebWorkerHandle, BootstrapOptions) {
     deno_core::extension!(deno_permissions_web_worker,
       options = {
         permissions: PermissionsContainer,
@@ -436,15 +444,15 @@ impl WebWorker {
       deno_console::deno_console::init_ops_and_esm(),
       deno_url::deno_url::init_ops_and_esm(),
       deno_web::deno_web::init_ops_and_esm::<PermissionsContainer>(
-        options.blob_store.clone(),
-        Some(main_module.clone()),
+        services.blob_store,
+        Some(options.main_module.clone()),
       ),
       deno_webgpu::deno_webgpu::init_ops_and_esm(),
       deno_canvas::deno_canvas::init_ops_and_esm(),
       deno_fetch::deno_fetch::init_ops_and_esm::<PermissionsContainer>(
         deno_fetch::Options {
           user_agent: options.bootstrap.user_agent.clone(),
-          root_cert_store_provider: options.root_cert_store_provider.clone(),
+          root_cert_store_provider: services.root_cert_store_provider.clone(),
           unsafely_ignore_certificate_errors: options
             .unsafely_ignore_certificate_errors
             .clone(),
@@ -457,17 +465,17 @@ impl WebWorker {
       ),
       deno_websocket::deno_websocket::init_ops_and_esm::<PermissionsContainer>(
         options.bootstrap.user_agent.clone(),
-        options.root_cert_store_provider.clone(),
+        services.root_cert_store_provider.clone(),
         options.unsafely_ignore_certificate_errors.clone(),
       ),
       deno_webstorage::deno_webstorage::init_ops_and_esm(None).disable(),
       deno_crypto::deno_crypto::init_ops_and_esm(options.seed),
       deno_broadcast_channel::deno_broadcast_channel::init_ops_and_esm(
-        options.broadcast_channel.clone(),
+        services.broadcast_channel,
       ),
       deno_ffi::deno_ffi::init_ops_and_esm::<PermissionsContainer>(),
       deno_net::deno_net::init_ops_and_esm::<PermissionsContainer>(
-        options.root_cert_store_provider.clone(),
+        services.root_cert_store_provider.clone(),
         options.unsafely_ignore_certificate_errors.clone(),
       ),
       deno_tls::deno_tls::init_ops_and_esm(),
@@ -477,7 +485,7 @@ impl WebWorker {
           options.seed,
           deno_kv::remote::HttpOptions {
             user_agent: options.bootstrap.user_agent.clone(),
-            root_cert_store_provider: options.root_cert_store_provider.clone(),
+            root_cert_store_provider: services.root_cert_store_provider,
             unsafely_ignore_certificate_errors: options
               .unsafely_ignore_certificate_errors
               .clone(),
@@ -492,25 +500,24 @@ impl WebWorker {
       deno_http::deno_http::init_ops_and_esm::<DefaultHttpPropertyExtractor>(),
       deno_io::deno_io::init_ops_and_esm(Some(options.stdio)),
       deno_fs::deno_fs::init_ops_and_esm::<PermissionsContainer>(
-        options.fs.clone(),
+        services.fs.clone(),
       ),
       deno_node::deno_node::init_ops_and_esm::<PermissionsContainer>(
-        options.node_services,
-        options.fs,
+        services.node_services,
+        services.fs,
       ),
       // Runtime ops that are always initialized for WebWorkers
-      ops::runtime::deno_runtime::init_ops_and_esm(main_module.clone()),
+      ops::runtime::deno_runtime::init_ops_and_esm(options.main_module.clone()),
       ops::worker_host::deno_worker_host::init_ops_and_esm(
-        options.create_web_worker_cb.clone(),
-        options.format_js_error_fn.clone(),
+        options.create_web_worker_cb,
+        options.format_js_error_fn,
       ),
       ops::fs_events::deno_fs_events::init_ops_and_esm(),
       ops::os::deno_os_worker::init_ops_and_esm(),
-      ops::permissions::deno_permissions::init_ops_and_esm(
-        options.permission_desc_parser.clone(),
-      ),
+      ops::otel::deno_otel::init_ops_and_esm(),
+      ops::permissions::deno_permissions::init_ops_and_esm(),
       ops::process::deno_process::init_ops_and_esm(
-        options.npm_process_state_provider,
+        services.npm_process_state_provider,
       ),
       ops::signal::deno_signal::init_ops_and_esm(),
       ops::tty::deno_tty::init_ops_and_esm(),
@@ -523,7 +530,7 @@ impl WebWorker {
         },
       ),
       deno_permissions_web_worker::init_ops_and_esm(
-        permissions,
+        services.permissions,
         enable_testing_features,
       ),
       runtime::init_ops_and_esm(),
@@ -556,17 +563,18 @@ impl WebWorker {
     );
 
     let mut js_runtime = JsRuntime::new(RuntimeOptions {
-      module_loader: Some(options.module_loader.clone()),
+      module_loader: Some(services.module_loader),
       startup_snapshot: options.startup_snapshot,
+      create_params: options.create_params,
       get_error_class_fn: options.get_error_class_fn,
-      shared_array_buffer_store: options.shared_array_buffer_store.clone(),
-      compiled_wasm_module_store: options.compiled_wasm_module_store.clone(),
+      shared_array_buffer_store: services.shared_array_buffer_store,
+      compiled_wasm_module_store: services.compiled_wasm_module_store,
       extensions,
       extension_transpiler: Some(Rc::new(|specifier, source| {
         maybe_transpile_source(specifier, source)
       })),
-      inspector: options.maybe_inspector_server.is_some(),
-      feature_checker: Some(options.feature_checker.clone()),
+      inspector: true,
+      feature_checker: Some(services.feature_checker),
       op_metrics_factory_fn,
       import_meta_resolve_callback: Some(Box::new(
         import_meta_resolve_callback,
@@ -582,24 +590,24 @@ impl WebWorker {
       js_runtime.op_state().borrow_mut().put(op_summary_metrics);
     }
 
-    if let Some(server) = options.maybe_inspector_server.clone() {
+    // Put inspector handle into the op state so we can put a breakpoint when
+    // executing a CJS entrypoint.
+    let op_state = js_runtime.op_state();
+    let inspector = js_runtime.inspector();
+    op_state.borrow_mut().put(inspector);
+
+    if let Some(server) = services.maybe_inspector_server {
       server.register_inspector(
-        main_module.to_string(),
+        options.main_module.to_string(),
         &mut js_runtime,
         false,
       );
-
-      // Put inspector handle into the op state so we can put a breakpoint when
-      // executing a CJS entrypoint.
-      let op_state = js_runtime.op_state();
-      let inspector = js_runtime.inspector();
-      op_state.borrow_mut().put(inspector);
     }
 
     let (internal_handle, external_handle) = {
       let handle = js_runtime.v8_isolate().thread_safe_handle();
       let (internal_handle, external_handle) =
-        create_handles(handle, name.clone(), options.worker_type);
+        create_handles(handle, options.name.clone(), options.worker_type);
       let op_state = js_runtime.op_state();
       let mut op_state = op_state.borrow_mut();
       op_state.put(internal_handle.clone());
@@ -630,12 +638,12 @@ impl WebWorker {
 
     (
       Self {
-        id: worker_id,
+        id: options.worker_id,
         js_runtime,
-        name,
+        name: options.name,
         internal_handle,
         worker_type: options.worker_type,
-        main_module,
+        main_module: options.main_module,
         poll_for_messages_fn: None,
         has_message_event_listener_fn: None,
         bootstrap_fn_global: Some(bootstrap_fn_global),
@@ -644,6 +652,7 @@ impl WebWorker {
         maybe_worker_metadata: options.maybe_worker_metadata,
       },
       external_handle,
+      options.bootstrap,
     )
   }
 
@@ -823,13 +832,12 @@ impl WebWorker {
 
         // TODO(mmastrac): we don't want to test this w/classic workers because
         // WPT triggers a failure here. This is only exposed via --enable-testing-features-do-not-use.
-        #[allow(clippy::print_stderr)]
         if self.worker_type == WebWorkerType::Module {
           panic!(
             "coding error: either js is polling or the worker is terminated"
           );
         } else {
-          eprintln!("classic worker terminated unexpectedly");
+          log::error!("classic worker terminated unexpectedly");
           Poll::Ready(Ok(()))
         }
       }
@@ -897,7 +905,6 @@ impl WebWorker {
   }
 }
 
-#[allow(clippy::print_stderr)]
 fn print_worker_error(
   error: &AnyError,
   name: &str,
@@ -910,7 +917,7 @@ fn print_worker_error(
     },
     None => error.to_string(),
   };
-  eprintln!(
+  log::error!(
     "{}: Uncaught (in worker \"{}\") {}",
     colors::red_bold("error"),
     name,
diff --git a/runtime/worker.rs b/runtime/worker.rs
index f72e6d7c09..c7bfb1c5f3 100644
--- a/runtime/worker.rs
+++ b/runtime/worker.rs
@@ -19,8 +19,9 @@ use deno_core::v8;
 use deno_core::CompiledWasmModuleStore;
 use deno_core::Extension;
 use deno_core::FeatureChecker;
-use deno_core::FsModuleLoader;
 use deno_core::GetErrorClassFn;
+use deno_core::InspectorSessionKind;
+use deno_core::InspectorSessionOptions;
 use deno_core::JsRuntime;
 use deno_core::LocalInspectorSession;
 use deno_core::ModuleCodeString;
@@ -50,7 +51,6 @@ use crate::code_cache::CodeCacheType;
 use crate::inspector_server::InspectorServer;
 use crate::ops;
 use crate::ops::process::NpmProcessStateProviderRc;
-use crate::permissions::RuntimePermissionDescriptorParser;
 use crate::shared::maybe_transpile_source;
 use crate::shared::runtime;
 use crate::BootstrapOptions;
@@ -128,6 +128,41 @@ pub struct MainWorker {
   dispatch_process_exit_event_fn_global: v8::Global<v8::Function>,
 }
 
+pub struct WorkerServiceOptions {
+  pub blob_store: Arc<BlobStore>,
+  pub broadcast_channel: InMemoryBroadcastChannel,
+  pub feature_checker: Arc<FeatureChecker>,
+  pub fs: Arc<dyn FileSystem>,
+  /// Implementation of `ModuleLoader` which will be
+  /// called when V8 requests to load ES modules.
+  ///
+  /// If not provided runtime will error if code being
+  /// executed tries to load modules.
+  pub module_loader: Rc<dyn ModuleLoader>,
+  pub node_services: Option<NodeExtInitServices>,
+  pub npm_process_state_provider: Option<NpmProcessStateProviderRc>,
+  pub permissions: PermissionsContainer,
+  pub root_cert_store_provider: Option<Arc<dyn RootCertStoreProvider>>,
+
+  /// The store to use for transferring SharedArrayBuffers between isolates.
+  /// If multiple isolates should have the possibility of sharing
+  /// SharedArrayBuffers, they should use the same [SharedArrayBufferStore]. If
+  /// no [SharedArrayBufferStore] is specified, SharedArrayBuffer can not be
+  /// serialized.
+  pub shared_array_buffer_store: Option<SharedArrayBufferStore>,
+
+  /// The store to use for transferring `WebAssembly.Module` objects between
+  /// isolates.
+  /// If multiple isolates should have the possibility of sharing
+  /// `WebAssembly.Module` objects, they should use the same
+  /// [CompiledWasmModuleStore]. If no [CompiledWasmModuleStore] is specified,
+  /// `WebAssembly.Module` objects cannot be serialized.
+  pub compiled_wasm_module_store: Option<CompiledWasmModuleStore>,
+
+  /// V8 code cache for module and script source code.
+  pub v8_code_cache: Option<Arc<dyn CodeCache>>,
+}
+
 pub struct WorkerOptions {
   pub bootstrap: BootstrapOptions,
 
@@ -148,20 +183,8 @@ pub struct WorkerOptions {
   pub create_params: Option<v8::CreateParams>,
 
   pub unsafely_ignore_certificate_errors: Option<Vec<String>>,
-  pub root_cert_store_provider: Option<Arc<dyn RootCertStoreProvider>>,
   pub seed: Option<u64>,
 
-  pub fs: Arc<dyn FileSystem>,
-  /// Implementation of `ModuleLoader` which will be
-  /// called when V8 requests to load ES modules.
-  ///
-  /// If not provided runtime will error if code being
-  /// executed tries to load modules.
-  pub module_loader: Rc<dyn ModuleLoader>,
-  pub node_services: Option<NodeExtInitServices>,
-  pub npm_process_state_provider: Option<NpmProcessStateProviderRc>,
-  pub permission_desc_parser:
-    Arc<dyn deno_permissions::PermissionDescriptorParser>,
   // Callbacks invoked when creating new instance of WebWorker
   pub create_web_worker_cb: Arc<ops::worker_host::CreateWebWorkerCb>,
   pub format_js_error_fn: Option<Arc<FormatJsErrorFn>>,
@@ -182,69 +205,31 @@ pub struct WorkerOptions {
   pub get_error_class_fn: Option<GetErrorClassFn>,
   pub cache_storage_dir: Option<std::path::PathBuf>,
   pub origin_storage_dir: Option<std::path::PathBuf>,
-  pub blob_store: Arc<BlobStore>,
-  pub broadcast_channel: InMemoryBroadcastChannel,
-
-  /// The store to use for transferring SharedArrayBuffers between isolates.
-  /// If multiple isolates should have the possibility of sharing
-  /// SharedArrayBuffers, they should use the same [SharedArrayBufferStore]. If
-  /// no [SharedArrayBufferStore] is specified, SharedArrayBuffer can not be
-  /// serialized.
-  pub shared_array_buffer_store: Option<SharedArrayBufferStore>,
-
-  /// The store to use for transferring `WebAssembly.Module` objects between
-  /// isolates.
-  /// If multiple isolates should have the possibility of sharing
-  /// `WebAssembly.Module` objects, they should use the same
-  /// [CompiledWasmModuleStore]. If no [CompiledWasmModuleStore] is specified,
-  /// `WebAssembly.Module` objects cannot be serialized.
-  pub compiled_wasm_module_store: Option<CompiledWasmModuleStore>,
   pub stdio: Stdio,
-  pub feature_checker: Arc<FeatureChecker>,
-
-  /// V8 code cache for module and script source code.
-  pub v8_code_cache: Option<Arc<dyn CodeCache>>,
 }
 
-// todo(dsherret): this is error prone to use. We should separate
-// out the WorkerOptions from the services.
 impl Default for WorkerOptions {
   fn default() -> Self {
-    let real_fs = Arc::new(deno_fs::RealFs);
     Self {
       create_web_worker_cb: Arc::new(|_| {
         unimplemented!("web workers are not supported")
       }),
-      fs: real_fs.clone(),
-      module_loader: Rc::new(FsModuleLoader),
       skip_op_registration: false,
       seed: None,
       unsafely_ignore_certificate_errors: Default::default(),
       should_break_on_first_statement: Default::default(),
       should_wait_for_inspector_session: Default::default(),
       strace_ops: Default::default(),
-      compiled_wasm_module_store: Default::default(),
-      shared_array_buffer_store: Default::default(),
       maybe_inspector_server: Default::default(),
       format_js_error_fn: Default::default(),
       get_error_class_fn: Default::default(),
       origin_storage_dir: Default::default(),
       cache_storage_dir: Default::default(),
-      broadcast_channel: Default::default(),
-      root_cert_store_provider: Default::default(),
-      node_services: Default::default(),
-      blob_store: Default::default(),
       extensions: Default::default(),
       startup_snapshot: Default::default(),
       create_params: Default::default(),
-      npm_process_state_provider: Default::default(),
       bootstrap: Default::default(),
       stdio: Default::default(),
-      feature_checker: Default::default(),
-      permission_desc_parser: Arc::new(RuntimePermissionDescriptorParser::new(
-        real_fs,
-      )),
-      v8_code_cache: Default::default(),
     }
   }
 }
@@ -318,20 +303,20 @@ pub fn create_op_metrics(
 impl MainWorker {
   pub fn bootstrap_from_options(
     main_module: ModuleSpecifier,
-    permissions: PermissionsContainer,
+    services: WorkerServiceOptions,
     options: WorkerOptions,
   ) -> Self {
-    let bootstrap_options = options.bootstrap.clone();
-    let mut worker = Self::from_options(main_module, permissions, options);
+    let (mut worker, bootstrap_options) =
+      Self::from_options(main_module, services, options);
     worker.bootstrap(bootstrap_options);
     worker
   }
 
-  pub fn from_options(
+  fn from_options(
     main_module: ModuleSpecifier,
-    permissions: PermissionsContainer,
+    services: WorkerServiceOptions,
     mut options: WorkerOptions,
-  ) -> Self {
+  ) -> (Self, BootstrapOptions) {
     deno_core::extension!(deno_permissions_worker,
       options = {
         permissions: PermissionsContainer,
@@ -365,7 +350,7 @@ impl MainWorker {
       deno_console::deno_console::init_ops_and_esm(),
       deno_url::deno_url::init_ops_and_esm(),
       deno_web::deno_web::init_ops_and_esm::<PermissionsContainer>(
-        options.blob_store.clone(),
+        services.blob_store.clone(),
         options.bootstrap.location.clone(),
       ),
       deno_webgpu::deno_webgpu::init_ops_and_esm(),
@@ -373,7 +358,7 @@ impl MainWorker {
       deno_fetch::deno_fetch::init_ops_and_esm::<PermissionsContainer>(
         deno_fetch::Options {
           user_agent: options.bootstrap.user_agent.clone(),
-          root_cert_store_provider: options.root_cert_store_provider.clone(),
+          root_cert_store_provider: services.root_cert_store_provider.clone(),
           unsafely_ignore_certificate_errors: options
             .unsafely_ignore_certificate_errors
             .clone(),
@@ -386,7 +371,7 @@ impl MainWorker {
       ),
       deno_websocket::deno_websocket::init_ops_and_esm::<PermissionsContainer>(
         options.bootstrap.user_agent.clone(),
-        options.root_cert_store_provider.clone(),
+        services.root_cert_store_provider.clone(),
         options.unsafely_ignore_certificate_errors.clone(),
       ),
       deno_webstorage::deno_webstorage::init_ops_and_esm(
@@ -394,11 +379,11 @@ impl MainWorker {
       ),
       deno_crypto::deno_crypto::init_ops_and_esm(options.seed),
       deno_broadcast_channel::deno_broadcast_channel::init_ops_and_esm(
-        options.broadcast_channel.clone(),
+        services.broadcast_channel.clone(),
       ),
       deno_ffi::deno_ffi::init_ops_and_esm::<PermissionsContainer>(),
       deno_net::deno_net::init_ops_and_esm::<PermissionsContainer>(
-        options.root_cert_store_provider.clone(),
+        services.root_cert_store_provider.clone(),
         options.unsafely_ignore_certificate_errors.clone(),
       ),
       deno_tls::deno_tls::init_ops_and_esm(),
@@ -408,7 +393,7 @@ impl MainWorker {
           options.seed,
           deno_kv::remote::HttpOptions {
             user_agent: options.bootstrap.user_agent.clone(),
-            root_cert_store_provider: options.root_cert_store_provider.clone(),
+            root_cert_store_provider: services.root_cert_store_provider.clone(),
             unsafely_ignore_certificate_errors: options
               .unsafely_ignore_certificate_errors
               .clone(),
@@ -423,11 +408,11 @@ impl MainWorker {
       deno_http::deno_http::init_ops_and_esm::<DefaultHttpPropertyExtractor>(),
       deno_io::deno_io::init_ops_and_esm(Some(options.stdio)),
       deno_fs::deno_fs::init_ops_and_esm::<PermissionsContainer>(
-        options.fs.clone(),
+        services.fs.clone(),
       ),
       deno_node::deno_node::init_ops_and_esm::<PermissionsContainer>(
-        options.node_services,
-        options.fs,
+        services.node_services,
+        services.fs,
       ),
       // Ops from this crate
       ops::runtime::deno_runtime::init_ops_and_esm(main_module.clone()),
@@ -437,11 +422,10 @@ impl MainWorker {
       ),
       ops::fs_events::deno_fs_events::init_ops_and_esm(),
       ops::os::deno_os::init_ops_and_esm(exit_code.clone()),
-      ops::permissions::deno_permissions::init_ops_and_esm(
-        options.permission_desc_parser,
-      ),
+      ops::otel::deno_otel::init_ops_and_esm(),
+      ops::permissions::deno_permissions::init_ops_and_esm(),
       ops::process::deno_process::init_ops_and_esm(
-        options.npm_process_state_provider,
+        services.npm_process_state_provider,
       ),
       ops::signal::deno_signal::init_ops_and_esm(),
       ops::tty::deno_tty::init_ops_and_esm(),
@@ -454,7 +438,7 @@ impl MainWorker {
         },
       ),
       deno_permissions_worker::init_ops_and_esm(
-        permissions,
+        services.permissions,
         enable_testing_features,
       ),
       runtime::init_ops_and_esm(),
@@ -494,20 +478,20 @@ impl MainWorker {
     });
 
     let mut js_runtime = JsRuntime::new(RuntimeOptions {
-      module_loader: Some(options.module_loader.clone()),
+      module_loader: Some(services.module_loader.clone()),
       startup_snapshot: options.startup_snapshot,
       create_params: options.create_params,
       skip_op_registration: options.skip_op_registration,
       get_error_class_fn: options.get_error_class_fn,
-      shared_array_buffer_store: options.shared_array_buffer_store.clone(),
-      compiled_wasm_module_store: options.compiled_wasm_module_store.clone(),
+      shared_array_buffer_store: services.shared_array_buffer_store.clone(),
+      compiled_wasm_module_store: services.compiled_wasm_module_store.clone(),
       extensions,
       extension_transpiler: Some(Rc::new(|specifier, source| {
         maybe_transpile_source(specifier, source)
       })),
-      inspector: options.maybe_inspector_server.is_some(),
+      inspector: true,
       is_main: true,
-      feature_checker: Some(options.feature_checker.clone()),
+      feature_checker: Some(services.feature_checker.clone()),
       op_metrics_factory_fn,
       wait_for_inspector_disconnect_callback: Some(
         wait_for_inspector_disconnect_callback,
@@ -519,7 +503,7 @@ impl MainWorker {
         validate_import_attributes_callback,
       )),
       import_assertions_support: deno_core::ImportAssertionsSupport::Error,
-      eval_context_code_cache_cbs: options.v8_code_cache.map(|cache| {
+      eval_context_code_cache_cbs: services.v8_code_cache.map(|cache| {
         let cache_clone = cache.clone();
         (
           Box::new(move |specifier: &ModuleSpecifier, code: &v8::String| {
@@ -563,6 +547,12 @@ impl MainWorker {
       js_runtime.op_state().borrow_mut().put(op_summary_metrics);
     }
 
+    // Put inspector handle into the op state so we can put a breakpoint when
+    // executing a CJS entrypoint.
+    let op_state = js_runtime.op_state();
+    let inspector = js_runtime.inspector();
+    op_state.borrow_mut().put(inspector);
+
     if let Some(server) = options.maybe_inspector_server.clone() {
       server.register_inspector(
         main_module.to_string(),
@@ -570,13 +560,8 @@ impl MainWorker {
         options.should_break_on_first_statement
           || options.should_wait_for_inspector_session,
       );
-
-      // Put inspector handle into the op state so we can put a breakpoint when
-      // executing a CJS entrypoint.
-      let op_state = js_runtime.op_state();
-      let inspector = js_runtime.inspector();
-      op_state.borrow_mut().put(inspector);
     }
+
     let (
       bootstrap_fn_global,
       dispatch_load_event_fn_global,
@@ -666,7 +651,7 @@ impl MainWorker {
       )
     };
 
-    Self {
+    let worker = Self {
       js_runtime,
       should_break_on_first_statement: options.should_break_on_first_statement,
       should_wait_for_inspector_session: options
@@ -678,7 +663,8 @@ impl MainWorker {
       dispatch_unload_event_fn_global,
       dispatch_process_beforeexit_event_fn_global,
       dispatch_process_exit_event_fn_global,
-    }
+    };
+    (worker, options.bootstrap)
   }
 
   pub fn bootstrap(&mut self, options: BootstrapOptions) {
@@ -810,7 +796,11 @@ impl MainWorker {
   /// was not configured to create inspector.
   pub fn create_inspector_session(&mut self) -> LocalInspectorSession {
     self.js_runtime.maybe_init_inspector();
-    self.js_runtime.inspector().borrow().create_local_session()
+    self.js_runtime.inspector().borrow().create_local_session(
+      InspectorSessionOptions {
+        kind: InspectorSessionKind::Blocking,
+      },
+    )
   }
 
   pub async fn run_event_loop(
diff --git a/runtime/worker_bootstrap.rs b/runtime/worker_bootstrap.rs
index 3f3c25c5ea..3f5c245a0f 100644
--- a/runtime/worker_bootstrap.rs
+++ b/runtime/worker_bootstrap.rs
@@ -1,5 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
+use crate::ops::otel::OtelConfig;
 use deno_core::v8;
 use deno_core::ModuleSpecifier;
 use serde::Serialize;
@@ -118,6 +119,8 @@ pub struct BootstrapOptions {
   // Used by `deno serve`
   pub serve_port: Option<u16>,
   pub serve_host: Option<String>,
+  // OpenTelemetry output options. If `None`, OpenTelemetry is disabled.
+  pub otel_config: Option<OtelConfig>,
 }
 
 impl Default for BootstrapOptions {
@@ -152,6 +155,7 @@ impl Default for BootstrapOptions {
       mode: WorkerExecutionMode::None,
       serve_port: Default::default(),
       serve_host: Default::default(),
+      otel_config: None,
     }
   }
 }
@@ -193,6 +197,8 @@ struct BootstrapV8<'a>(
   Option<bool>,
   // serve worker count
   Option<usize>,
+  // OTEL config
+  Box<[u8]>,
 );
 
 impl BootstrapOptions {
@@ -219,6 +225,11 @@ impl BootstrapOptions {
       self.serve_host.as_deref(),
       serve_is_main,
       serve_worker_count,
+      if let Some(otel_config) = self.otel_config.as_ref() {
+        Box::new([otel_config.console as u8, otel_config.deterministic as u8])
+      } else {
+        Box::new([])
+      },
     );
 
     bootstrap.serialize(ser).unwrap()
diff --git a/rust-toolchain.toml b/rust-toolchain.toml
index e8d3cddd18..3d572e0d69 100644
--- a/rust-toolchain.toml
+++ b/rust-toolchain.toml
@@ -1,3 +1,3 @@
 [toolchain]
-channel = "1.80.1"
+channel = "1.82.0"
 components = ["rustfmt", "clippy"]
diff --git a/tests/Cargo.toml b/tests/Cargo.toml
index bb84c22496..ede509e380 100644
--- a/tests/Cargo.toml
+++ b/tests/Cargo.toml
@@ -47,6 +47,8 @@ deno_tls.workspace = true
 fastwebsockets = { workspace = true, features = ["upgrade", "unstable-split"] }
 file_test_runner = "0.7.2"
 flaky_test = "=0.2.2"
+hickory-client = "=0.24"
+hickory-server = "=0.24"
 http.workspace = true
 http-body-util.workspace = true
 hyper.workspace = true
@@ -60,8 +62,6 @@ serde.workspace = true
 test_util.workspace = true
 tokio.workspace = true
 tower-lsp.workspace = true
-trust-dns-client = "=0.23.2"
-trust-dns-server = "=0.23.2"
 url.workspace = true
 uuid = { workspace = true, features = ["serde"] }
 zeromq.workspace = true
diff --git a/tests/ffi/tests/integration_tests.rs b/tests/ffi/tests/integration_tests.rs
index c84a1b820d..dbc0036bc2 100644
--- a/tests/ffi/tests/integration_tests.rs
+++ b/tests/ffi/tests/integration_tests.rs
@@ -95,10 +95,10 @@ fn basic() {
     579.912\n\
     579.912\n\
     579\n\
-    8589934590\n\
-    -8589934590\n\
-    8589934590\n\
-    -8589934590\n\
+    8589934590n\n\
+    -8589934590n\n\
+    8589934590n\n\
+    -8589934590n\n\
     9007199254740992n\n\
     9007199254740992n\n\
     -9007199254740992n\n\
diff --git a/tests/integration/check_tests.rs b/tests/integration/check_tests.rs
index f30828a665..178ac6493f 100644
--- a/tests/integration/check_tests.rs
+++ b/tests/integration/check_tests.rs
@@ -4,7 +4,6 @@ use deno_lockfile::NewLockfileOptions;
 use deno_semver::jsr::JsrDepPackageReq;
 use test_util as util;
 use test_util::itest;
-use util::env_vars_for_npm_tests;
 use util::TestContext;
 use util::TestContextBuilder;
 
@@ -21,104 +20,6 @@ itest!(check_all_local {
   http_server: true,
 });
 
-itest!(module_detection_force {
-  args: "check --quiet check/module_detection_force/main.ts",
-  output_str: Some(""),
-});
-
-// Regression test for https://github.com/denoland/deno/issues/14937.
-itest!(declaration_header_file_with_no_exports {
-  args: "check --quiet check/declaration_header_file_with_no_exports.ts",
-  output_str: Some(""),
-});
-
-itest!(check_jsximportsource_importmap_config {
-  args: "check --quiet --config check/jsximportsource_importmap_config/deno.json check/jsximportsource_importmap_config/main.tsx",
-  output_str: Some(""),
-});
-
-itest!(jsx_not_checked {
-  args: "check check/jsx_not_checked/main.jsx",
-  output: "check/jsx_not_checked/main.out",
-  envs: env_vars_for_npm_tests(),
-  http_server: true,
-  exit_code: 1,
-});
-
-itest!(check_npm_install_diagnostics {
-  args: "check --quiet check/npm_install_diagnostics/main.ts",
-  output: "check/npm_install_diagnostics/main.out",
-  envs: vec![("NO_COLOR".to_string(), "1".to_string())],
-  exit_code: 1,
-});
-
-itest!(check_static_response_json {
-  args: "check --quiet check/response_json.ts",
-  exit_code: 0,
-});
-
-itest!(check_node_builtin_modules_ts {
-  args: "check --quiet check/node_builtin_modules/mod.ts",
-  output: "check/node_builtin_modules/mod.ts.out",
-  envs: env_vars_for_npm_tests(),
-  exit_code: 1,
-  http_server: true,
-});
-
-itest!(check_node_builtin_modules_js {
-  args: "check --quiet check/node_builtin_modules/mod.js",
-  output: "check/node_builtin_modules/mod.js.out",
-  envs: env_vars_for_npm_tests(),
-  exit_code: 1,
-  http_server: true,
-});
-
-itest!(check_no_error_truncation {
-  args: "check --quiet check/no_error_truncation/main.ts --config check/no_error_truncation/deno.json",
-  output: "check/no_error_truncation/main.out",
-  envs: vec![("NO_COLOR".to_string(), "1".to_string())],
-  exit_code: 1,
-});
-
-itest!(check_broadcast_channel {
-  args: "check --quiet check/broadcast_channel.ts",
-  exit_code: 0,
-});
-
-itest!(check_deno_not_found {
-  args: "check --quiet check/deno_not_found/main.ts",
-  output: "check/deno_not_found/main.out",
-  exit_code: 1,
-});
-
-itest!(check_with_exclude_option_by_dir {
-  args:
-    "check --quiet --config check/exclude_option/deno.exclude_dir.json check/exclude_option/ignored/index.ts",
-  output_str: Some(""),
-  exit_code: 0,
-});
-
-itest!(check_with_exclude_option_by_glob {
-  args:
-    "check --quiet --config check/exclude_option/deno.exclude_glob.json check/exclude_option/ignored/index.ts",
-  output_str: Some(""),
-  exit_code: 0,
-});
-
-itest!(check_without_exclude_option {
-  args:
-    "check --quiet --config check/exclude_option/deno.json check/exclude_option/ignored/index.ts",
-  output: "check/exclude_option/exclude_option.ts.error.out",
-  exit_code: 1,
-});
-
-itest!(check_imported_files_listed_in_exclude_option {
-  args:
-    "check --quiet --config check/exclude_option/deno.exclude_dir.json check/exclude_option/index.ts",
-  output: "check/exclude_option/exclude_option.ts.error.out",
-  exit_code: 1,
-});
-
 #[test]
 fn cache_switching_config_then_no_config() {
   let context = TestContext::default();
@@ -241,12 +142,6 @@ fn ts_no_recheck_on_redirect() {
   output.assert_matches_text("Hello\n");
 }
 
-itest!(check_dts {
-  args: "check --quiet check/dts/check_dts.d.ts",
-  output: "check/dts/check_dts.out",
-  exit_code: 1,
-});
-
 #[test]
 fn check_error_in_dep_then_fix() {
   let test_context = TestContextBuilder::new().use_temp_cwd().build();
diff --git a/tests/integration/compile_tests.rs b/tests/integration/compile_tests.rs
index 0a5916f6f7..fa6364a136 100644
--- a/tests/integration/compile_tests.rs
+++ b/tests/integration/compile_tests.rs
@@ -241,7 +241,7 @@ fn compile_with_file_exists_error() {
       "./compile/args.ts",
     ])
     .run()
-    .assert_matches_text(&format!(
+    .assert_matches_text(format!(
       concat!(
         "[WILDCARD]error: Could not compile to file '{}' because its parent directory ",
         "is an existing file. You can use the `--output <file-path>` flag to ",
@@ -269,7 +269,7 @@ fn compile_with_directory_exists_error() {
       &exe.to_string_lossy(),
       "./compile/args.ts"
     ]).run()
-    .assert_matches_text(&format!(
+    .assert_matches_text(format!(
       concat!(
         "[WILDCARD]error: Could not compile to file '{}' because a directory exists with ",
         "the same name. You can use the `--output <file-path>` flag to ",
@@ -297,7 +297,7 @@ fn compile_with_conflict_file_exists_error() {
       &exe.to_string_lossy(),
       "./compile/args.ts"
     ]).run()
-    .assert_matches_text(&format!(
+    .assert_matches_text(format!(
       concat!(
         "[WILDCARD]error: Could not compile to file '{}' because the file already exists ",
         "and cannot be overwritten. Please delete the existing file or ",
@@ -1111,7 +1111,7 @@ console.log(getValue());"#,
     .run();
   output.assert_exit_code(0);
   output.assert_matches_text(
-    r#"Download http://localhost:4260/@denotest/esm-basic
+    r#"Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 Check file:///[WILDCARD]/main.ts
diff --git a/tests/integration/flags_tests.rs b/tests/integration/flags_tests.rs
index 160de3ec1d..663da363da 100644
--- a/tests/integration/flags_tests.rs
+++ b/tests/integration/flags_tests.rs
@@ -18,10 +18,9 @@ fn help_output() {
     "Start an interactive Read-Eval-Print Loop (REPL) for Deno",
     "Evaluate a script from the command line",
     "Add dependencies",
-    "Install script as an executable",
-    "Uninstall a script previously installed with deno install",
+    "Installs dependencies either in the local project or globally to a bin directory",
+    "Uninstalls a dependency or an executable script in the installation root's bin directory",
     "Run benchmarks",
-    "Cache the dependencies",
     "Type-check the dependencies",
     "Compile the script into a self contained executable",
     "Print coverage reports",
diff --git a/tests/integration/jsr_tests.rs b/tests/integration/jsr_tests.rs
index af5b24fe41..c4812e6bfb 100644
--- a/tests/integration/jsr_tests.rs
+++ b/tests/integration/jsr_tests.rs
@@ -191,7 +191,7 @@ fn reload_info_not_found_cache_but_exists_remote() {
       Url::parse(&format!("http://127.0.0.1:4250/{}/meta.json", package))
         .unwrap();
     let cache = deno_cache_dir::GlobalHttpCache::new(
-      deno_dir.path().join("deps").to_path_buf(),
+      deno_dir.path().join("remote").to_path_buf(),
       deno_cache_dir::TestRealDenoCacheEnv,
     );
     let entry = cache
diff --git a/tests/integration/jupyter_tests.rs b/tests/integration/jupyter_tests.rs
index 1b2c213118..e99780a276 100644
--- a/tests/integration/jupyter_tests.rs
+++ b/tests/integration/jupyter_tests.rs
@@ -628,3 +628,37 @@ async fn jupyter_store_history_false() -> Result<()> {
 
   Ok(())
 }
+
+#[tokio::test]
+async fn jupyter_http_server() -> Result<()> {
+  let (_ctx, client, _process) = setup().await;
+  client
+    .send(
+      Shell,
+      "execute_request",
+      json!({
+        "silent": false,
+        "store_history": false,
+        "code": r#"Deno.serve({ port: 10234 }, (req) => Response.json({ hello: "world" }))"#,
+      }),
+    )
+    .await?;
+
+  let reply = client.recv(Shell).await?;
+  assert_eq!(reply.header.msg_type, "execute_reply");
+  assert_json_subset(
+    reply.content,
+    json!({
+      "status": "ok",
+      "execution_count": 0,
+    }),
+  );
+
+  for _ in 0..3 {
+    let resp = reqwest::get("http://localhost:10234").await.unwrap();
+    let text: serde_json::Value = resp.json().await.unwrap();
+    assert_eq!(text, json!({ "hello": "world" }));
+  }
+
+  Ok(())
+}
diff --git a/tests/integration/lsp_tests.rs b/tests/integration/lsp_tests.rs
index 539e3cc7e2..dcef696084 100644
--- a/tests/integration/lsp_tests.rs
+++ b/tests/integration/lsp_tests.rs
@@ -1049,6 +1049,191 @@ fn lsp_workspace_enable_paths_no_workspace_configuration() {
   client.shutdown();
 }
 
+#[test]
+fn lsp_did_refresh_deno_configuration_tree_notification() {
+  let context = TestContextBuilder::new().use_temp_cwd().build();
+  let temp_dir = context.temp_dir();
+  temp_dir.create_dir_all("workspace/member1");
+  temp_dir.create_dir_all("workspace/member2");
+  temp_dir.create_dir_all("non_workspace1");
+  temp_dir.create_dir_all("non_workspace2");
+  temp_dir.write(
+    "workspace/deno.json",
+    json!({
+      "workspace": [
+        "member1",
+        "member2",
+      ],
+    })
+    .to_string(),
+  );
+  temp_dir.write("workspace/member1/deno.json", json!({}).to_string());
+  temp_dir.write("workspace/member1/package.json", json!({}).to_string());
+  temp_dir.write("workspace/member2/package.json", json!({}).to_string());
+  temp_dir.write("non_workspace1/deno.json", json!({}).to_string());
+  let mut client = context.new_lsp_command().build();
+  client.initialize_default();
+  let res = client
+    .read_notification_with_method::<Value>(
+      "deno/didRefreshDenoConfigurationTree",
+    )
+    .unwrap();
+  assert_eq!(
+    res,
+    json!({
+      "data": [
+        {
+          "scopeUri": temp_dir.url().join("non_workspace1/").unwrap(),
+          "workspaceRootScopeUri": null,
+          "denoJson": {
+            "uri": temp_dir.url().join("non_workspace1/deno.json").unwrap(),
+          },
+          "packageJson": null,
+        },
+        {
+          "scopeUri": temp_dir.url().join("workspace/").unwrap(),
+          "workspaceRootScopeUri": null,
+          "denoJson": {
+            "uri": temp_dir.url().join("workspace/deno.json").unwrap(),
+          },
+          "packageJson": null,
+        },
+        {
+          "scopeUri": temp_dir.url().join("workspace/member1/").unwrap(),
+          "workspaceRootScopeUri": temp_dir.url().join("workspace/").unwrap(),
+          "denoJson": {
+            "uri": temp_dir.url().join("workspace/member1/deno.json").unwrap(),
+          },
+          "packageJson": {
+            "uri": temp_dir.url().join("workspace/member1/package.json").unwrap(),
+          },
+        },
+        {
+          "scopeUri": temp_dir.url().join("workspace/member2/").unwrap(),
+          "workspaceRootScopeUri": temp_dir.url().join("workspace/").unwrap(),
+          "denoJson": null,
+          "packageJson": {
+            "uri": temp_dir.url().join("workspace/member2/package.json").unwrap(),
+          },
+        },
+      ],
+    }),
+  );
+  temp_dir.write("non_workspace2/deno.json", json!({}).to_string());
+  client.did_change_watched_files(json!({
+    "changes": [{
+      "uri": temp_dir.url().join("non_workspace2/deno.json").unwrap(),
+      "type": 1,
+    }],
+  }));
+  let res = client
+    .read_notification_with_method::<Value>(
+      "deno/didRefreshDenoConfigurationTree",
+    )
+    .unwrap();
+  assert_eq!(
+    res,
+    json!({
+      "data": [
+        {
+          "scopeUri": temp_dir.url().join("non_workspace1/").unwrap(),
+          "workspaceRootScopeUri": null,
+          "denoJson": {
+            "uri": temp_dir.url().join("non_workspace1/deno.json").unwrap(),
+          },
+          "packageJson": null,
+        },
+        {
+          "scopeUri": temp_dir.url().join("non_workspace2/").unwrap(),
+          "workspaceRootScopeUri": null,
+          "denoJson": {
+            "uri": temp_dir.url().join("non_workspace2/deno.json").unwrap(),
+          },
+          "packageJson": null,
+        },
+        {
+          "scopeUri": temp_dir.url().join("workspace/").unwrap(),
+          "workspaceRootScopeUri": null,
+          "denoJson": {
+            "uri": temp_dir.url().join("workspace/deno.json").unwrap(),
+          },
+          "packageJson": null,
+        },
+        {
+          "scopeUri": temp_dir.url().join("workspace/member1/").unwrap(),
+          "workspaceRootScopeUri": temp_dir.url().join("workspace/").unwrap(),
+          "denoJson": {
+            "uri": temp_dir.url().join("workspace/member1/deno.json").unwrap(),
+          },
+          "packageJson": {
+            "uri": temp_dir.url().join("workspace/member1/package.json").unwrap(),
+          },
+        },
+        {
+          "scopeUri": temp_dir.url().join("workspace/member2/").unwrap(),
+          "workspaceRootScopeUri": temp_dir.url().join("workspace/").unwrap(),
+          "denoJson": null,
+          "packageJson": {
+            "uri": temp_dir.url().join("workspace/member2/package.json").unwrap(),
+          },
+        },
+      ],
+    }),
+  );
+  client.change_configuration(json!({
+    "deno": {
+      "disablePaths": ["non_workspace1"],
+    },
+  }));
+  let res = client
+    .read_notification_with_method::<Value>(
+      "deno/didRefreshDenoConfigurationTree",
+    )
+    .unwrap();
+  assert_eq!(
+    res,
+    json!({
+      "data": [
+        {
+          "scopeUri": temp_dir.url().join("non_workspace2/").unwrap(),
+          "workspaceRootScopeUri": null,
+          "denoJson": {
+            "uri": temp_dir.url().join("non_workspace2/deno.json").unwrap(),
+          },
+          "packageJson": null,
+        },
+        {
+          "scopeUri": temp_dir.url().join("workspace/").unwrap(),
+          "workspaceRootScopeUri": null,
+          "denoJson": {
+            "uri": temp_dir.url().join("workspace/deno.json").unwrap(),
+          },
+          "packageJson": null,
+        },
+        {
+          "scopeUri": temp_dir.url().join("workspace/member1/").unwrap(),
+          "workspaceRootScopeUri": temp_dir.url().join("workspace/").unwrap(),
+          "denoJson": {
+            "uri": temp_dir.url().join("workspace/member1/deno.json").unwrap(),
+          },
+          "packageJson": {
+            "uri": temp_dir.url().join("workspace/member1/package.json").unwrap(),
+          },
+        },
+        {
+          "scopeUri": temp_dir.url().join("workspace/member2/").unwrap(),
+          "workspaceRootScopeUri": temp_dir.url().join("workspace/").unwrap(),
+          "denoJson": null,
+          "packageJson": {
+            "uri": temp_dir.url().join("workspace/member2/package.json").unwrap(),
+          },
+        },
+      ],
+    }),
+  );
+  client.shutdown();
+}
+
 #[test]
 fn lsp_did_change_deno_configuration_notification() {
   let context = TestContextBuilder::new().use_temp_cwd().build();
@@ -1342,6 +1527,7 @@ fn lsp_import_map_import_completions() {
         "/#/": "./src/",
         "fs": "https://example.com/fs/index.js",
         "std/": "https://example.com/std@0.123.0/",
+        "lib/": "./lib/",
       },
       "scopes": {
         "file:///": {
@@ -1364,17 +1550,18 @@ fn lsp_import_map_import_completions() {
       "uri": uri,
       "languageId": "typescript",
       "version": 1,
-      "text": "import * as a from \"/~/b.ts\";\nimport * as b from \"\""
-    }
+      "text": r#"
+        import * as b from "";
+        import * as b from "/~/";
+        import * as b from "lib/";
+      "#,
+    },
   }));
 
   let res = client.get_completion(
     &uri,
-    (1, 20),
-    json!({
-      "triggerKind": 2,
-      "triggerCharacter": "\""
-    }),
+    (1, 28),
+    json!({ "triggerKind": 2, "triggerCharacter": "\"" }),
   );
   assert_eq!(
     json!(res),
@@ -1409,6 +1596,13 @@ fn lsp_import_map_import_completions() {
           "sortText": "std",
           "insertText": "std",
           "commitCharacters": ["\"", "'"],
+        }, {
+          "label": "lib",
+          "kind": 19,
+          "detail": "(import map)",
+          "sortText": "lib",
+          "insertText": "lib",
+          "commitCharacters": ["\"", "'"],
         }, {
           "label": "fs",
           "kind": 17,
@@ -1435,32 +1629,10 @@ fn lsp_import_map_import_completions() {
     })
   );
 
-  client.write_notification(
-    "textDocument/didChange",
-    json!({
-      "textDocument": {
-        "uri": uri,
-        "version": 2
-      },
-      "contentChanges": [
-        {
-          "range": {
-            "start": { "line": 1, "character": 20 },
-            "end": { "line": 1, "character": 20 }
-          },
-          "text": "/~/"
-        }
-      ]
-    }),
-  );
-
   let res = client.get_completion(
-    uri,
-    (1, 23),
-    json!({
-      "triggerKind": 2,
-      "triggerCharacter": "/"
-    }),
+    &uri,
+    (2, 31),
+    json!({ "triggerKind": 2, "triggerCharacter": "/" }),
   );
   assert_eq!(
     json!(res),
@@ -1475,15 +1647,44 @@ fn lsp_import_map_import_completions() {
           "filterText": "/~/b.ts",
           "textEdit": {
             "range": {
-              "start": { "line": 1, "character": 20 },
-              "end": { "line": 1, "character": 23 }
+              "start": { "line": 2, "character": 28 },
+              "end": { "line": 2, "character": 31 },
             },
-            "newText": "/~/b.ts"
+            "newText": "/~/b.ts",
           },
           "commitCharacters": ["\"", "'"],
-        }
-      ]
-    })
+        },
+      ],
+    }),
+  );
+
+  let res = client.get_completion(
+    &uri,
+    (3, 32),
+    json!({ "triggerKind": 2, "triggerCharacter": "/" }),
+  );
+  assert_eq!(
+    json!(res),
+    json!({
+      "isIncomplete": false,
+      "items": [
+        {
+          "label": "b.ts",
+          "kind": 17,
+          "detail": "(local)",
+          "sortText": "1",
+          "filterText": "lib/b.ts",
+          "textEdit": {
+            "range": {
+              "start": { "line": 3, "character": 28 },
+              "end": { "line": 3, "character": 32 },
+            },
+            "newText": "lib/b.ts",
+          },
+          "commitCharacters": ["\"", "'"],
+        },
+      ],
+    }),
   );
 
   client.shutdown();
@@ -1626,15 +1827,41 @@ fn lsp_hover_disabled() {
 fn lsp_inlay_hints() {
   let context = TestContextBuilder::new().use_temp_cwd().build();
   let mut client = context.new_lsp_command().build();
-  client.initialize(|builder| {
-    builder.enable_inlay_hints();
-  });
+  client.initialize_default();
+  client.change_configuration(json!({
+    "deno": {
+      "enable": true,
+    },
+    "typescript": {
+      "inlayHints": {
+        "parameterNames": {
+          "enabled": "all",
+        },
+        "parameterTypes": {
+          "enabled": true,
+        },
+        "variableTypes": {
+          "enabled": true,
+        },
+        "propertyDeclarationTypes": {
+          "enabled": true,
+        },
+        "functionLikeReturnTypes": {
+          "enabled": true,
+        },
+        "enumMemberValues": {
+          "enabled": true,
+        },
+      },
+    },
+  }));
   client.did_open(json!({
     "textDocument": {
       "uri": "file:///a/file.ts",
       "languageId": "typescript",
       "version": 1,
-      "text": r#"function a(b: string) {
+      "text": r#"
+        function a(b: string) {
           return b;
         }
 
@@ -1653,8 +1880,19 @@ fn lsp_inlay_hints() {
         }
 
         ["a"].map((v) => v + v);
-        "#
-    }
+
+        interface Bar {
+          someField: string;
+        }
+        function getBar(): Bar {
+          return { someField: "foo" };
+        }
+        // This shouldn't have a type hint because the variable name makes it
+        // redundant.
+        const bar = getBar();
+        const someValue = getBar();
+      "#,
+    },
   }));
   let res = client.write_request(
     "textDocument/inlayHint",
@@ -1663,65 +1901,130 @@ fn lsp_inlay_hints() {
         "uri": "file:///a/file.ts",
       },
       "range": {
-        "start": { "line": 0, "character": 0 },
-        "end": { "line": 19, "character": 0, }
-      }
+        "start": { "line": 1, "character": 0 },
+        "end": { "line": 31, "character": 0, },
+      },
     }),
   );
   assert_eq!(
     res,
     json!([
       {
-        "position": { "line": 0, "character": 21 },
-        "label": ": string",
+        "position": { "line": 1, "character": 29 },
+        "label": [{ "value": ": " }, { "value": "string" }],
         "kind": 1,
-        "paddingLeft": true
+        "paddingLeft": true,
       }, {
-        "position": { "line": 4, "character": 10 },
-        "label": "b:",
+        "position": { "line": 5, "character": 10 },
+        "label": [
+          {
+            "value": "b",
+            "location": {
+              "uri": "file:///a/file.ts",
+              "range": {
+                "start": { "line": 1, "character": 19 },
+                "end": { "line": 1, "character": 20 },
+              },
+            },
+          },
+          { "value": ":" },
+        ],
         "kind": 2,
-        "paddingRight": true
+        "paddingRight": true,
       }, {
-        "position": { "line": 7, "character": 11 },
+        "position": { "line": 8, "character": 11 },
         "label": "= 0",
-        "paddingLeft": true
+        "paddingLeft": true,
       }, {
-        "position": { "line": 10, "character": 17 },
-        "label": "string:",
+        "position": { "line": 11, "character": 17 },
+        "label": [
+          {
+            "value": "string",
+            "location": {
+              "uri": "deno:/asset/lib.es5.d.ts",
+              "range": {
+                "start": { "line": 41, "character": 26 },
+                "end": { "line": 41, "character": 32 },
+              },
+            },
+          },
+          { "value": ":" },
+        ],
         "kind": 2,
-        "paddingRight": true
+        "paddingRight": true,
       }, {
-        "position": { "line": 10, "character": 24 },
-        "label": "radix:",
+        "position": { "line": 11, "character": 24 },
+        "label": [
+          {
+            "value": "radix",
+            "location": {
+              "uri": "deno:/asset/lib.es5.d.ts",
+              "range": {
+                "start": { "line": 41, "character": 42 },
+                "end": { "line": 41, "character": 47 },
+              },
+            },
+          },
+          { "value": ":" },
+        ],
         "kind": 2,
-        "paddingRight": true
+        "paddingRight": true,
       }, {
-        "position": { "line": 12, "character": 15 },
-        "label": ": number",
+        "position": { "line": 13, "character": 15 },
+        "label": [{ "value": ": " }, { "value": "number" }],
         "kind": 1,
-        "paddingLeft": true
+        "paddingLeft": true,
       }, {
-        "position": { "line": 15, "character": 11 },
-        "label": ": number",
+        "position": { "line": 16, "character": 11 },
+        "label": [{ "value": ": " }, { "value": "number" }],
         "kind": 1,
-        "paddingLeft": true
+        "paddingLeft": true,
       }, {
-        "position": { "line": 18, "character": 18 },
-        "label": "callbackfn:",
+        "position": { "line": 19, "character": 18 },
+        "label": [
+          {
+            "value": "callbackfn",
+            "location": {
+              "uri": "deno:/asset/lib.es5.d.ts",
+              "range": {
+                "start": { "line": 1462, "character": 11 },
+                "end": { "line": 1462, "character": 21 },
+              },
+            },
+          },
+          { "value": ":" },
+        ],
         "kind": 2,
-        "paddingRight": true
+        "paddingRight": true,
       }, {
-        "position": { "line": 18, "character": 20 },
-        "label": ": string",
+        "position": { "line": 19, "character": 20 },
+        "label": [{ "value": ": " }, { "value": "string" }],
         "kind": 1,
-        "paddingLeft": true
+        "paddingLeft": true,
       }, {
-        "position": { "line": 18, "character": 21 },
-        "label": ": string",
+        "position": { "line": 19, "character": 21 },
+        "label": [{ "value": ": " }, { "value": "string" }],
         "kind": 1,
-        "paddingLeft": true
-      }
-    ])
+        "paddingLeft": true,
+      }, {
+        "position": { "line": 30, "character": 23 },
+        "label": [
+          { "value": ": " },
+          {
+            "value": "Bar",
+            "location": {
+              "uri": "file:///a/file.ts",
+              "range": {
+                "start": { "line": 21, "character": 18 },
+                "end": { "line": 21, "character": 21 },
+              },
+            },
+          },
+        ],
+        "kind": 1,
+        "paddingLeft": true,
+      },
+    ]),
   );
   client.shutdown();
 }
@@ -5652,7 +5955,7 @@ fn lsp_jsr_code_action_missing_declaration() {
                       "character": 6,
                     },
                   },
-                  "newText": "import type { ReturnType } from \"jsr:@denotest/types-file/types\";\n",
+                  "newText": "import { ReturnType } from \"jsr:@denotest/types-file/types\";\n",
                 },
                 {
                   "range": {
@@ -5906,6 +6209,135 @@ fn lsp_code_actions_deno_cache_all() {
   client.shutdown();
 }
 
+#[test]
+fn lsp_code_actions_deno_types_for_npm() {
+  let context = TestContextBuilder::new()
+    .use_http_server()
+    .use_temp_cwd()
+    .add_npm_env_vars()
+    .build();
+  let temp_dir = context.temp_dir();
+  temp_dir.write("deno.json", json!({}).to_string());
+  temp_dir.write(
+    "package.json",
+    json!({
+      "dependencies": {
+        "react": "^18.2.0",
+        "@types/react": "^18.3.10",
+      },
+    })
+    .to_string(),
+  );
+  temp_dir.create_dir_all("managed_node_modules");
+  temp_dir.write(
+    "managed_node_modules/deno.json",
+    json!({
+      "nodeModulesDir": false,
+    })
+    .to_string(),
+  );
+  context.run_npm("install");
+  let mut client = context.new_lsp_command().build();
+  client.initialize_default();
+  client.did_open(json!({
+    "textDocument": {
+      "uri": temp_dir.url().join("file.ts").unwrap(),
+      "languageId": "typescript",
+      "version": 1,
+      "text": "import \"react\";\n",
+    }
+  }));
+  let res = client.write_request(
+    "textDocument/codeAction",
+    json!({
+      "textDocument": {
+        "uri": temp_dir.url().join("file.ts").unwrap(),
+      },
+      "range": {
+        "start": { "line": 0, "character": 7 },
+        "end": { "line": 0, "character": 7 },
+      },
+      "context": { "diagnostics": [], "only": ["quickfix"] },
+    }),
+  );
+  assert_eq!(
+    res,
+    json!([
+      {
+        "title": "Add @deno-types directive for \"@types/react\"",
+        "kind": "quickfix",
+        "edit": {
+          "changes": {
+            temp_dir.url().join("file.ts").unwrap(): [
+              {
+                "range": {
+                  "start": { "line": 0, "character": 0 },
+                  "end": { "line": 0, "character": 0 },
+                },
+                "newText": "// @deno-types=\"@types/react\"\n",
+              },
+            ],
+          },
+        },
+      },
+    ]),
+  );
+  client.did_open(json!({
+    "textDocument": {
+      "uri": temp_dir.url().join("managed_node_modules/file.ts").unwrap(),
+      "languageId": "typescript",
+      "version": 1,
+      "text": "import \"npm:react\";\n",
+    }
+  }));
+  client.write_request(
+    "workspace/executeCommand",
+    json!({
+      "command": "deno.cache",
+      "arguments": [
+        [],
+        temp_dir.url().join("managed_node_modules/file.ts").unwrap(),
+      ],
+    }),
+  );
+  let res = client.write_request(
+    "textDocument/codeAction",
+    json!({
+      "textDocument": {
+        "uri": temp_dir.url().join("managed_node_modules/file.ts").unwrap(),
+      },
+      "range": {
+        "start": { "line": 0, "character": 7 },
+        "end": { "line": 0, "character": 7 },
+      },
+      "context": { "diagnostics": [], "only": ["quickfix"] },
+    }),
+  );
+  assert_eq!(
+    res,
+    json!([
+      {
+        "title": "Add @deno-types directive for \"npm:@types/react@^18.3.10\"",
+        "kind": "quickfix",
+        "edit": {
+          "changes": {
+            temp_dir.url().join("managed_node_modules/file.ts").unwrap(): [
+              {
+                "range": {
+                  "start": { "line": 0, "character": 0 },
+                  "end": { "line": 0, "character": 0 },
+                },
+                "newText": "// @deno-types=\"npm:@types/react@^18.3.10\"\n",
+              },
+            ],
+          },
+        },
+      },
+    ]),
+  );
+  client.shutdown();
+}
+
 #[test]
 fn lsp_cache_on_save() {
   let context = TestContextBuilder::new()
@@ -5964,6 +6396,45 @@ fn lsp_cache_on_save() {
   client.shutdown();
 }
 
+// Regression test for https://github.com/denoland/deno/issues/25999.
+#[test]
+fn lsp_asset_document_dom_code_action() {
+  let context = TestContextBuilder::new().use_temp_cwd().build();
+  let temp_dir = context.temp_dir();
+  temp_dir.write(
+    "deno.json",
+    json!({
+      "compilerOptions": {
+        "lib": ["deno.window", "dom"],
+      },
+    })
+    .to_string(),
+  );
+  let mut client = context.new_lsp_command().build();
+  client.initialize_default();
+  client.did_open(json!({
+    "textDocument": {
+      "uri": temp_dir.url().join("file.ts").unwrap(),
+      "languageId": "typescript",
+      "version": 1,
+      "text": r#""#,
+    },
+  }));
+  let res = client.write_request(
+    "textDocument/codeAction",
+    json!({
+      "textDocument": { "uri": "asset:///lib.dom.d.ts" },
+      "range": {
+        "start": { "line": 0, "character": 0 },
+        "end": { "line": 0, "character": 0 },
+      },
+      "context": { "diagnostics": [], "only": ["quickfix"] },
+    }),
+  );
+  assert_eq!(res, json!(null));
+  client.shutdown();
+}
+
 // Regression test for https://github.com/denoland/deno/issues/22122.
 #[test]
 fn lsp_cache_then_definition() {
@@ -6037,6 +6508,16 @@ fn lsp_code_actions_imports() {
   let context = TestContextBuilder::new().use_temp_cwd().build();
   let mut client = context.new_lsp_command().build();
   client.initialize_default();
+  client.change_configuration(json!({
+    "deno": {
+      "enable": true,
+    },
+    "typescript": {
+      "preferences": {
+        "preferTypeOnlyAutoImports": true,
+      },
+    },
+  }));
   client.did_open(json!({
       "textDocument": {
         "uri": "file:///a/file00.ts",
@@ -6147,6 +6628,23 @@ export class DuckConfig {
           }]
         }]
       }
+    }, {
+      "title": "Add all missing imports",
+      "kind": "quickfix",
+      "diagnostics": [{
+        "range": {
+          "start": { "line": 0, "character": 50 },
+          "end": { "line": 0, "character": 67 }
+        },
+        "severity": 1,
+        "code": 2304,
+        "source": "deno-ts",
+        "message": "Cannot find name 'DuckConfigOptions'."
+      }],
+      "data": {
+        "specifier": "file:///a/file00.ts",
+        "fixId": "fixMissingImport"
+      }
     }, {
       "title": "Add import from \"./file01.ts\"",
       "kind": "quickfix",
@@ -6175,23 +6673,6 @@ export class DuckConfig {
           }]
         }]
       }
-    }, {
-      "title": "Add all missing imports",
-      "kind": "quickfix",
-      "diagnostics": [{
-        "range": {
-          "start": { "line": 0, "character": 50 },
-          "end": { "line": 0, "character": 67 }
-        },
-        "severity": 1,
-        "code": 2304,
-        "source": "deno-ts",
-        "message": "Cannot find name 'DuckConfigOptions'."
-      }],
-      "data": {
-        "specifier": "file:///a/file00.ts",
-        "fixId": "fixMissingImport"
-      }
     }])
   );
   let res = client.write_request(
@@ -6336,7 +6817,7 @@ fn lsp_code_actions_imports_dts() {
               "start": { "line": 0, "character": 0 },
               "end": { "line": 0, "character": 0 },
             },
-            "newText": "import type { SomeType } from \"./decl.d.ts\";\n",
+            "newText": "import { SomeType } from \"./decl.d.ts\";\n",
           }],
         }],
       },
@@ -6345,6 +6826,117 @@ fn lsp_code_actions_imports_dts() {
   client.shutdown();
 }
 
+#[test]
+fn lsp_code_actions_import_map_remap() {
+  let context = TestContextBuilder::new().use_temp_cwd().build();
+  let temp_dir = context.temp_dir();
+  temp_dir.write(
+    "deno.json",
+    json!({
+      "imports": {
+        "foo": "./foo.ts",
+        "bar": "./bar.ts",
+      },
+    })
+    .to_string(),
+  );
+  temp_dir.write("foo.ts", "");
+  temp_dir.write("bar.ts", "");
+  let mut client = context.new_lsp_command().build();
+  client.initialize_default();
+  let diagnostics = client.did_open(json!({
+    "textDocument": {
+      "uri": temp_dir.url().join("file.ts").unwrap(),
+      "languageId": "typescript",
+      "version": 1,
+      "text": r#"
+        import "./foo.ts";
+        import type {} from "./bar.ts";
+      "#,
+    }
+  }));
+  let res = client.write_request(
+    "textDocument/codeAction",
+    json!({
+      "textDocument": { "uri": temp_dir.url().join("file.ts").unwrap() },
+      "range": {
+        "start": { "line": 0, "character": 0 },
+        "end": { "line": 3, "character": 0 },
+      },
+      "context": {
+        "diagnostics": diagnostics.all(),
+        "only": ["quickfix"],
+      },
+    }),
+  );
+  assert_eq!(
+    res,
+    json!([
+      {
+        "title": "Update \"./foo.ts\" to \"foo\" to use import map.",
+        "kind": "quickfix",
+        "diagnostics": [
+          {
+            "range": {
+              "start": { "line": 1, "character": 15 },
+              "end": { "line": 1, "character": 25 },
+            },
+            "severity": 4,
+            "code": "import-map-remap",
+            "source": "deno",
+            "message": "The import specifier can be remapped to \"foo\" which will resolve it via the active import map.",
+            "data": { "from": "./foo.ts", "to": "foo" },
+          },
+        ],
+        "edit": {
+          "changes": {
+            temp_dir.url().join("file.ts").unwrap(): [
+              {
+                "range": {
+                  "start": { "line": 1, "character": 15 },
+                  "end": { "line": 1, "character": 25 },
+                },
+                "newText": "\"foo\"",
+              },
+            ],
+          },
+        },
+      },
+      {
+        "title": "Update \"./bar.ts\" to \"bar\" to use import map.",
+        "kind": "quickfix",
+        "diagnostics": [
+          {
+            "range": {
+              "start": { "line": 2, "character": 28 },
+              "end": { "line": 2, "character": 38 },
+            },
+            "severity": 4,
+            "code": "import-map-remap",
+            "source": "deno",
+            "message": "The import specifier can be remapped to \"bar\" which will resolve it via the active import map.",
+            "data": { "from": "./bar.ts", "to": "bar" },
+          },
+        ],
+        "edit": {
+          "changes": {
+            temp_dir.url().join("file.ts").unwrap(): [
+              {
+                "range": {
+                  "start": { "line": 2, "character": 28 },
+                  "end": { "line": 2, "character": 38 },
+                },
+                "newText": "\"bar\"",
+              },
+            ],
+          },
+        },
+      },
+    ]),
+  );
+  client.shutdown();
+}
+
 #[test]
 fn lsp_code_actions_refactor() {
   let context = TestContextBuilder::new().use_temp_cwd().build();
@@ -6656,7 +7248,7 @@ fn lsp_code_actions_imports_respects_fmt_config() {
               "start": { "line": 0, "character": 0 },
               "end": { "line": 0, "character": 0 }
             },
-            "newText": "import type { DuckConfigOptions } from './file01.ts'\n"
+            "newText": "import { DuckConfigOptions } from './file01.ts'\n"
           }]
         }]
       }
@@ -6709,7 +7301,7 @@ fn lsp_code_actions_imports_respects_fmt_config() {
               "start": { "line": 0, "character": 0 },
               "end": { "line": 0, "character": 0 }
             },
-            "newText": "import type { DuckConfigOptions } from './file01.ts'\n"
+            "newText": "import { DuckConfigOptions } from './file01.ts'\n"
           }]
         }]
       },
@@ -6809,7 +7401,7 @@ fn lsp_quote_style_from_workspace_settings() {
               "start": { "line": 0, "character": 0 },
               "end": { "line": 0, "character": 0 },
             },
-            "newText": "import type { DuckConfigOptions } from './file01.ts';\n",
+            "newText": "import { DuckConfigOptions } from './file01.ts';\n",
           }],
         }],
       },
@@ -6853,7 +7445,7 @@ fn lsp_quote_style_from_workspace_settings() {
               "start": { "line": 0, "character": 0 },
               "end": { "line": 0, "character": 0 },
             },
-            "newText": "import type { DuckConfigOptions } from \"./file01.ts\";\n",
+            "newText": "import { DuckConfigOptions } from \"./file01.ts\";\n",
           }],
         }],
       },
@@ -7533,6 +8125,151 @@ fn lsp_npm_completions_auto_import_and_quick_fix_no_import_map() {
   client.shutdown();
 }
 
+#[test]
+fn lsp_npm_auto_import_and_quick_fix_byonm() {
+  let context = TestContextBuilder::new()
+    .use_http_server()
+    .use_temp_cwd()
+    .add_npm_env_vars()
+    .build();
+  let temp_dir = context.temp_dir();
+  temp_dir.write("deno.json", json!({}).to_string());
+  temp_dir.write(
+    "package.json",
+    json!({
+      "dependencies": {
+        "cowsay": "*",
+      },
+    })
+    .to_string(),
+  );
+  context
+    .new_command()
+    .args("install")
+    .run()
+    .skip_output_check();
+  temp_dir.write("other.ts", "import \"cowsay\";\n");
+  let mut client = context.new_lsp_command().build();
+  client.initialize_default();
+  let diagnostics = client.did_open(json!({
+    "textDocument": {
+      "uri": temp_dir.url().join("file.ts").unwrap(),
+      "languageId": "typescript",
+      "version": 1,
+      "text": "think({ text: \"foo\" });\n",
+    },
+  }));
+  let list = client.get_completion_list(
+    temp_dir.url().join("file.ts").unwrap(),
+    (0, 5),
+    json!({ "triggerKind": 1 }),
+  );
+  assert!(!list.is_incomplete);
+  let item = list
+    .items
+    .iter()
+    .find(|item| item.label == "think")
+    .unwrap();
+  let res = client.write_request("completionItem/resolve", item);
+  assert_eq!(
+    res,
+    json!({
+      "label": "think",
+      "labelDetails": {
+        "description": "cowsay",
+      },
+      "kind": 3,
+      "detail": "function think(options: IOptions): string",
+      "documentation": {
+        "kind": "markdown",
+        "value": "\n\n*@param*  \noptions ## Face :\nEither choose a mode (set the value as true) **_or_**\nset your own defined eyes and tongue to `e` and `T`.\n- ### `e` : eyes\n- ### `T` : tongue\n\n## Cow :\nEither specify a cow name (e.g. \"fox\") **_or_**\nset the value of `r` to true which selects a random cow.\n- ### `r` : random selection\n- ### `f` : cow name - from `cows` folder\n\n## Modes :\nModes are just ready-to-use faces, here's their list:\n- #### `b` : borg\n- #### `d` : dead      \n- #### `g` : greedy\n- #### `p` : paranoia\n- #### `s` : stoned\n- #### `t` : tired\n- #### `w` : youthful\n- #### `y` : wired  \n\n*@example*  \n```\n// custom cow and face\ncowsay.think({\n    text: 'Hello world!',\n    e: '^^', // eyes\n    T: 'U ', // tongue\n    f: 'USA' // name of the cow from `cows` folder\n})\n\n// using a random cow\ncowsay.think({\n    text: 'Hello world!',\n    e: 'xx', // eyes\n    r: true, // random mode - use a random cow.\n})\n\n// using a mode\ncowsay.think({\n    text: 'Hello world!',\n    y: true, // using y mode - youthful mode\n})\n```",
+      },
+      "sortText": "￿16_0",
+      "additionalTextEdits": [
+        {
+          "range": {
+            "start": { "line": 0, "character": 0 },
+            "end": { "line": 0, "character": 0 },
+          },
+          "newText": "import { think } from \"cowsay\";\n\n",
+        },
+      ],
+    }),
+  );
+  let diagnostics = diagnostics
+    .messages_with_file_and_source(
+      temp_dir.url().join("file.ts").unwrap().as_str(),
+      "deno-ts",
+    )
+    .diagnostics;
+  let res = client.write_request(
+    "textDocument/codeAction",
+    json!(json!({
+      "textDocument": {
+        "uri": temp_dir.url().join("file.ts").unwrap(),
+      },
+      "range": {
+        "start": { "line": 0, "character": 0 },
+        "end": { "line": 0, "character": 5 },
+      },
+      "context": {
+        "diagnostics": &diagnostics,
+        "only": ["quickfix"],
+      },
+    })),
+  );
+  assert_eq!(
+    res,
+    json!([
+      {
+        "title": "Add import from \"cowsay\"",
+        "kind": "quickfix",
+        "diagnostics": &diagnostics,
+        "edit": {
+          "documentChanges": [{
+            "textDocument": {
+              "uri": temp_dir.url().join("file.ts").unwrap(),
+              "version": 1,
+            },
+            "edits": [{
+              "range": {
+                "start": { "line": 0, "character": 0 },
+                "end": { "line": 0, "character": 0 },
+              },
+              "newText": "import { think } from \"cowsay\";\n\n",
+            }],
+          }],
+        },
+      },
+      {
+        "title": "Add missing function declaration 'think'",
+        "kind": "quickfix",
+        "diagnostics": &diagnostics,
+        "edit": {
+          "documentChanges": [
+            {
+              "textDocument": {
+                "uri": temp_dir.url().join("file.ts").unwrap(),
+                "version": 1,
+              },
+              "edits": [
+                {
+                  "range": {
+                    "start": { "line": 1, "character": 0 },
+                    "end": { "line": 1, "character": 0 },
+                  },
+                  "newText": "\nfunction think(arg0: { text: string; }) {\n  throw new Error(\"Function not implemented.\");\n}\n",
+                },
+              ],
+            },
+          ],
+        },
+      },
+    ]),
+  );
+  client.shutdown();
+}
+
 #[test]
 fn lsp_completions_node_specifier() {
   let context = TestContextBuilder::new().use_temp_cwd().build();
@@ -7645,8 +8382,8 @@ fn lsp_infer_return_type() {
   let context = TestContextBuilder::new().use_temp_cwd().build();
   let temp_dir = context.temp_dir();
   temp_dir.write("deno.json", json!({}).to_string());
-  let types_file = source_file(
-    temp_dir.path().join("types.d.ts"),
+  temp_dir.write(
+    "types.d.ts",
     r#"
       export interface SomeInterface {
         someField: number;
@@ -7727,7 +8464,7 @@ fn lsp_infer_return_type() {
                   "start": { "line": 1, "character": 20 },
                   "end": { "line": 1, "character": 20 },
                 },
-                "newText": format!(": import(\"{}\").SomeInterface", types_file.url()),
+                "newText": ": import(\"./types.d.ts\").SomeInterface",
               },
             ],
           },
@@ -8375,6 +9112,74 @@ fn lsp_completions_auto_import_and_quick_fix_with_import_map() {
   client.shutdown();
 }
 
+// Regression test for https://github.com/denoland/deno/issues/25775.
+#[test]
+fn lsp_quick_fix_missing_import_exclude_bare_node_builtins() {
+  let context = TestContextBuilder::new()
+    .use_http_server()
+    .use_temp_cwd()
+    .add_npm_env_vars()
+    .build();
+  let temp_dir = context.temp_dir();
+  temp_dir.write(
+    "package.json",
+    json!({
+      "dependencies": {
+        "@types/node": "*",
+      },
+    })
+    .to_string(),
+  );
+  context.run_npm("install");
+  let mut client = context.new_lsp_command().build();
+  client.initialize_default();
+  let diagnostics = client.did_open(json!({
+    "textDocument": {
+      "uri": temp_dir.url().join("file.ts").unwrap(),
+      "languageId": "typescript",
+      "version": 1,
+      // Include node:buffer import to ensure @types/node is in the dep graph.
+      "text": "import \"node:buffer\";\nassert();\n",
+    },
+  }));
+  let diagnostic = diagnostics
+    .all()
+    .into_iter()
+    .find(|d| d.message == "Cannot find name 'assert'.")
+    .unwrap();
+  let res = client.write_request(
+    "textDocument/codeAction",
+    json!({
+      "textDocument": {
+        "uri": temp_dir.url().join("file.ts").unwrap(),
+      },
+      "range": {
+        "start": { "line": 1, "character": 0 },
+        "end": { "line": 1, "character": 6 },
+      },
+      "context": {
+        "diagnostics": [&diagnostic],
+        "only": ["quickfix"],
+      },
+    }),
+  );
+  let code_actions =
+    serde_json::from_value::<Vec<lsp::CodeAction>>(res).unwrap();
+  let titles = code_actions
+    .iter()
+    .map(|a| a.title.clone())
+    .collect::<Vec<_>>();
+  assert_eq!(
+    json!(titles),
+    json!([
+      "Add import from \"node:assert\"",
+      "Add import from \"node:console\"",
+      "Add missing function declaration 'assert'",
+    ]),
+  );
+  client.shutdown();
+}
+
 #[test]
 fn lsp_completions_snippet() {
   let context = TestContextBuilder::new().use_temp_cwd().build();
@@ -9190,14 +9995,15 @@ fn lsp_auto_discover_registry() {
       "triggerCharacter": "@"
     }),
   );
-  let (method, res) = client.read_notification();
-  assert_eq!(method, "deno/registryState");
+  let res = client
+    .read_notification_with_method::<Value>("deno/registryState")
+    .unwrap();
   assert_eq!(
     res,
-    Some(json!({
+    json!({
       "origin": "http://localhost:4545",
       "suggestions": true,
-    }))
+    }),
   );
   client.shutdown();
 }
@@ -9904,7 +10710,6 @@ fn lsp_diagnostics_refresh_dependents() {
   assert_eq!(json!(diagnostics.all()), json!([])); // no diagnostics now
 
   client.shutdown();
-  assert_eq!(client.queue_len(), 0);
 }
 
 // Regression test for https://github.com/denoland/deno/issues/10897.
@@ -14863,25 +15668,23 @@ fn lsp_sloppy_imports() {
 fn lsp_sloppy_imports_prefers_dts() {
   let context = TestContextBuilder::new().use_temp_cwd().build();
   let temp_dir = context.temp_dir();
-  let temp_dir = temp_dir.path();
-
-  temp_dir
-    .join("deno.json")
-    .write(r#"{ "unstable": ["sloppy-imports"] }"#);
-
-  let mut client: LspClient = context
-    .new_lsp_command()
-    .set_root_dir(temp_dir.clone())
-    .build();
-  client.initialize_default();
-
-  temp_dir.join("a.js").write("export const foo: number;");
-
-  let a_dts = source_file(temp_dir.join("a.d.ts"), "export const foo = 3;");
+  temp_dir.write("deno.json", json!({}).to_string());
+  temp_dir.write("a.js", "export const foo: number;");
+  let a_dts =
+    source_file(temp_dir.path().join("a.d.ts"), "export const foo = 3;");
   let file = source_file(
-    temp_dir.join("file.ts"),
+    temp_dir.path().join("file.ts"),
     "import { foo } from './a.js';\nconsole.log(foo);",
   );
+  let mut client: LspClient = context.new_lsp_command().build();
+  client.initialize_default();
+  client.change_configuration(json!({
+    "deno": {
+      "enable": true,
+      "unstable": ["sloppy-imports"],
+    },
+  }));
+
   let diagnostics = client.did_open_file(&file);
   // no other warnings because "a.js" exists
   assert_eq!(
@@ -15336,6 +16139,55 @@ fn lsp_cjs_import_dual() {
   );
 }
 
+#[test]
+fn lsp_type_commonjs() {
+  let context = TestContextBuilder::new()
+    .use_http_server()
+    .use_temp_cwd()
+    .add_npm_env_vars()
+    .build();
+  let temp_dir = context.temp_dir();
+  temp_dir.write("deno.json", r#"{}"#);
+  temp_dir.write(
+    "package.json",
+    r#"{
+  "type": "commonjs",
+  "dependencies": {
+    "@denotest/dual-cjs-esm": "1"
+  }
+}"#,
+  );
+  context.run_npm("install");
+
+  let mut client = context.new_lsp_command().build();
+  client.initialize_default();
+  let main_url = temp_dir.path().join("main.ts").url_file();
+  let diagnostics = client.did_open(
+    json!({
+      "textDocument": {
+        "uri": main_url,
+        "languageId": "typescript",
+        "version": 1,
+        // getKind() should resolve as "cjs" and cause a type checker error
+        "text": "import mod = require('@denotest/dual-cjs-esm');\nconst kind: 'other' = mod.getKind(); console.log(kind);",
+      }
+    }),
+  );
+  assert_eq!(
+    json!(diagnostics.all()),
+    json!([{
+      "range": {
+          "start": { "line": 1, "character": 6, },
+          "end": { "line": 1, "character": 10, },
+      },
+      "severity": 1,
+      "code": 2322,
+      "source": "deno-ts",
+      "message": "Type '\"cjs\"' is not assignable to type '\"other\"'.",
+    }])
+  );
+}
+
 #[test]
 fn lsp_ts_code_fix_any_param() {
   let context = TestContextBuilder::new().use_temp_cwd().build();
diff --git a/tests/integration/node_unit_tests.rs b/tests/integration/node_unit_tests.rs
index d66db5a40e..40bd7b2fbb 100644
--- a/tests/integration/node_unit_tests.rs
+++ b/tests/integration/node_unit_tests.rs
@@ -212,3 +212,7 @@ itest!(unhandled_rejection_web_process {
   envs: env_vars_for_npm_tests(),
   http_server: true,
 });
+
+// !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
+// The itest macro is deprecated. Please move your new test to ~/tests/specs.
+// !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
diff --git a/tests/integration/npm_tests.rs b/tests/integration/npm_tests.rs
index f47b1bdd4a..f8c6eebf39 100644
--- a/tests/integration/npm_tests.rs
+++ b/tests/integration/npm_tests.rs
@@ -876,7 +876,7 @@ fn auto_discover_lock_file() {
     .run();
   output
     .assert_matches_text(
-r#"Download http://localhost:4260/@denotest/bin
+r#"Download http://localhost:4260/@denotest%2fbin
 error: Integrity check failed for package: "npm:@denotest/bin@1.0.0". Unable to verify that the package
 is the same as when the lockfile was generated.
 
@@ -1058,10 +1058,10 @@ fn reload_info_not_found_cache_but_exists_remote() {
     .run();
   output.assert_matches_text(concat!(
     "[UNORDERED_START]\n",
-    "Download http://localhost:4260/@denotest/esm-basic\n",
-    "Download http://localhost:4260/@denotest/esm-import-cjs-default\n",
-    "Download http://localhost:4260/@denotest/cjs-default-export\n",
-    "Download http://localhost:4260/@denotest/cjs-default-export/1.0.0.tgz\n",
+    "Download http://localhost:4260/@denotest%2fesm-basic\n",
+    "Download http://localhost:4260/@denotest%2fesm-import-cjs-default\n",
+    "Download http://localhost:4260/@denotest%2fcjs-default-export\n",
+    "Download http://localhost:4260/@denotestcjs-default-export/1.0.0.tgz\n",
     "Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz\n",
     "Download http://localhost:4260/@denotest/esm-import-cjs-default/1.0.0.tgz\n",
     "[UNORDERED_END]\n",
@@ -1088,8 +1088,8 @@ fn reload_info_not_found_cache_but_exists_remote() {
     let output = test_context.new_command().args("run main.ts").run();
     output.assert_matches_text(concat!(
       "[UNORDERED_START]\n",
-      "Download http://localhost:4260/@denotest/esm-import-cjs-default\n",
-      "Download http://localhost:4260/@denotest/cjs-default-export\n",
+      "Download http://localhost:4260/@denotest%2fesm-import-cjs-default\n",
+      "Download http://localhost:4260/@denotest%2fcjs-default-export\n",
       "[UNORDERED_END]\n",
       "Node esm importing node cjs\n[WILDCARD]",
     ));
@@ -1120,8 +1120,8 @@ fn reload_info_not_found_cache_but_exists_remote() {
     let output = test_context.new_command().args("run main.ts").run();
     output.assert_matches_text(concat!(
       "[UNORDERED_START]\n",
-      "Download http://localhost:4260/@denotest/esm-import-cjs-default\n",
-      "Download http://localhost:4260/@denotest/cjs-default-export\n",
+      "Download http://localhost:4260/@denotest%2fesm-import-cjs-default\n",
+      "Download http://localhost:4260/@denotest%2fcjs-default-export\n",
       "[UNORDERED_END]\n",
       "Node esm importing node cjs\n[WILDCARD]",
     ));
@@ -1159,8 +1159,8 @@ fn reload_info_not_found_cache_but_exists_remote() {
     let output = test_context.new_command().args("run main.ts").run();
     output.assert_matches_text(concat!(
       "[UNORDERED_START]\n",
-      "Download http://localhost:4260/@denotest/esm-import-cjs-default\n",
-      "Download http://localhost:4260/@denotest/cjs-default-export\n",
+      "Download http://localhost:4260/@denotest%2fesm-import-cjs-default\n",
+      "Download http://localhost:4260/@denotest%2fcjs-default-export\n",
       "[UNORDERED_END]\n",
       "[UNORDERED_START]\n",
       "Initialize @denotest/cjs-default-export@1.0.0\n",
@@ -1196,9 +1196,9 @@ fn reload_info_not_found_cache_but_exists_remote() {
     let output = test_context.new_command().args("run main.ts").run();
     output.assert_matches_text(concat!(
       "[UNORDERED_START]\n",
-      "Download http://localhost:4260/@denotest/esm-basic\n",
-      "Download http://localhost:4260/@denotest/esm-import-cjs-default\n",
-      "Download http://localhost:4260/@denotest/cjs-default-export\n",
+      "Download http://localhost:4260/@denotest%2fesm-basic\n",
+      "Download http://localhost:4260/@denotest%2fesm-import-cjs-default\n",
+      "Download http://localhost:4260/@denotest%2fcjs-default-export\n",
       "[UNORDERED_END]\n",
       "Initialize @denotest/esm-basic@1.0.0\n",
       "Node esm importing node cjs\n[WILDCARD]",
@@ -1237,9 +1237,9 @@ fn reload_info_not_found_cache_but_exists_remote() {
     let output = test_context.new_command().args("run main.ts").run();
     output.assert_matches_text(concat!(
       "[UNORDERED_START]\n",
-      "Download http://localhost:4260/@denotest/cjs-default-export\n",
-      "Download http://localhost:4260/@denotest/esm-basic\n",
-      "Download http://localhost:4260/@denotest/esm-import-cjs-default\n",
+      "Download http://localhost:4260/@denotest%2fcjs-default-export\n",
+      "Download http://localhost:4260/@denotest%2fesm-basic\n",
+      "Download http://localhost:4260/@denotest%2fesm-import-cjs-default\n",
       "[UNORDERED_END]\n",
       "Node esm importing node cjs\n[WILDCARD]",
     ));
@@ -1419,7 +1419,7 @@ fn top_level_install_package_json_explicit_opt_in() {
   temp_dir.write("main.ts", "console.log(5);");
   let output = test_context.new_command().args("cache main.ts").run();
   output.assert_matches_text(concat!(
-    "Download http://localhost:4260/@denotest/esm-basic\n",
+    "Download http://localhost:4260/@denotest%2fesm-basic\n",
     "Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz\n",
     "Initialize @denotest/esm-basic@1.0.0\n",
   ));
diff --git a/tests/integration/repl_tests.rs b/tests/integration/repl_tests.rs
index 3f137ce7cb..9eceb2f05d 100644
--- a/tests/integration/repl_tests.rs
+++ b/tests/integration/repl_tests.rs
@@ -255,6 +255,20 @@ fn console_log() {
     console.write_line("'world'");
     console.expect("\"world\"");
   });
+
+  // https://github.com/denoland/deno/issues/21428
+  let (out, err) = util::run_and_collect_output_with_args(
+    true,
+    vec![
+      "repl",
+      "--eval-file=./../specs/repl/console_log/093_console_log_format.js",
+    ],
+    None,
+    None,
+    false,
+  );
+  assert_contains!(out, "0.5");
+  assert!(err.is_empty());
 }
 
 #[test]
@@ -1136,3 +1150,22 @@ fn eval_file_promise_error() {
   assert_contains!(out, "Uncaught undefined");
   assert!(err.is_empty());
 }
+
+#[test]
+fn repl_json_imports() {
+  let context = TestContextBuilder::default().use_temp_cwd().build();
+  let temp_dir = context.temp_dir();
+  temp_dir.write("./data.json", r#"{"hello": "world"}"#);
+  context
+    .new_command()
+    .env("NO_COLOR", "1")
+    .args_vec(["repl", "-A"])
+    .with_pty(|mut console| {
+      console.write_line_raw(
+        "import data from './data.json' with { type: 'json' };",
+      );
+      console.expect("undefined");
+      console.write_line_raw("data");
+      console.expect(r#"{ hello: "world" }"#);
+    });
+}
diff --git a/tests/integration/run_tests.rs b/tests/integration/run_tests.rs
index 1e1d6ed61b..549b88bac4 100644
--- a/tests/integration/run_tests.rs
+++ b/tests/integration/run_tests.rs
@@ -16,280 +16,19 @@ use deno_tls::rustls;
 use deno_tls::rustls::ClientConnection;
 use deno_tls::rustls_pemfile;
 use deno_tls::TlsStream;
+use hickory_client::serialize::txt::Parser;
 use pretty_assertions::assert_eq;
 use test_util as util;
 use test_util::itest;
 use test_util::TempDir;
-use trust_dns_client::serialize::txt::Lexer;
-use trust_dns_client::serialize::txt::Parser;
 use util::assert_contains;
 use util::assert_not_contains;
-use util::env_vars_for_npm_tests;
 use util::PathRef;
 use util::TestContext;
 use util::TestContextBuilder;
 
 const CODE_CACHE_DB_FILE_NAME: &str = "v8_code_cache_v2";
 
-itest!(stdout_write_all {
-  args: "run --quiet run/stdout_write_all.ts",
-  output: "run/stdout_write_all.out",
-});
-
-itest!(stdin_read_all {
-  args: "run --quiet run/stdin_read_all.ts",
-  output: "run/stdin_read_all.out",
-  input: Some("01234567890123456789012345678901234567890123456789"),
-});
-
-itest!(stdout_write_sync_async {
-  args: "run --quiet run/stdout_write_sync_async.ts",
-  output: "run/stdout_write_sync_async.out",
-});
-
-itest!(_001_hello {
-  args: "run --reload run/001_hello.js",
-  output: "run/001_hello.js.out",
-});
-
-itest!(_002_hello {
-  args: "run --quiet --reload run/002_hello.ts",
-  output: "run/002_hello.ts.out",
-});
-
-itest!(_003_relative_import {
-  args: "run --quiet --reload run/003_relative_import.ts",
-  output: "run/003_relative_import.ts.out",
-});
-
-itest!(_004_set_timeout {
-  args: "run --quiet --reload run/004_set_timeout.ts",
-  output: "run/004_set_timeout.ts.out",
-});
-
-itest!(_005_more_imports {
-  args: "run --quiet --reload run/005_more_imports.ts",
-  output: "run/005_more_imports.ts.out",
-});
-
-itest!(_006_url_imports {
-  args: "run --quiet --reload --allow-import run/006_url_imports.ts",
-  output: "run/006_url_imports.ts.out",
-  http_server: true,
-});
-
-itest!(_012_async {
-  args: "run --quiet --reload run/012_async.ts",
-  output: "run/012_async.ts.out",
-});
-
-itest!(_013_dynamic_import {
-  args: "run --quiet --reload --allow-read run/013_dynamic_import.ts",
-  output: "run/013_dynamic_import.ts.out",
-});
-
-itest!(_014_duplicate_import {
-  args: "run --quiet --reload --allow-read run/014_duplicate_import.ts ",
-  output: "run/014_duplicate_import.ts.out",
-});
-
-itest!(_015_duplicate_parallel_import {
-  args:
-    "run --quiet --reload --allow-read run/015_duplicate_parallel_import.js",
-  output: "run/015_duplicate_parallel_import.js.out",
-});
-
-itest!(_016_double_await {
-  args: "run --quiet --allow-read --reload run/016_double_await.ts",
-  output: "run/016_double_await.ts.out",
-});
-
-itest!(_017_import_redirect {
-  args: "run --quiet --allow-import --reload run/017_import_redirect.ts",
-  output: "run/017_import_redirect.ts.out",
-});
-
-itest!(_017_import_redirect_check {
-  args:
-    "run --quiet --allow-import --reload --check run/017_import_redirect.ts",
-  output: "run/017_import_redirect.ts.out",
-});
-
-itest!(_017_import_redirect_vendor_dir {
-  args:
-    "run --quiet --allow-import --reload --vendor --check $TESTDATA/run/017_import_redirect.ts",
-  output: "run/017_import_redirect.ts.out",
-  temp_cwd: true,
-});
-
-itest!(_017_import_redirect_info {
-  args: "info --quiet --allow-import --reload run/017_import_redirect.ts",
-  output: "run/017_import_redirect_info.out",
-});
-
-itest!(_018_async_catch {
-  args: "run --quiet --reload run/018_async_catch.ts",
-  output: "run/018_async_catch.ts.out",
-});
-
-itest!(_019_media_types {
-  args: "run --reload --allow-import run/019_media_types.ts",
-  output: "run/019_media_types.ts.out",
-  http_server: true,
-});
-
-itest!(_020_json_modules {
-  args: "run --reload run/020_json_modules.ts",
-  output: "run/020_json_modules.ts.out",
-  exit_code: 1,
-});
-
-itest!(_021_mjs_modules {
-  args: "run --quiet --reload run/021_mjs_modules.ts",
-  output: "run/021_mjs_modules.ts.out",
-});
-
-itest!(_025_reload_js_type_error {
-  args: "run --quiet --reload run/025_reload_js_type_error.js",
-  output: "run/025_reload_js_type_error.js.out",
-});
-
-itest!(_027_redirect_typescript {
-  args: "run --quiet --reload --allow-import run/027_redirect_typescript.ts",
-  output: "run/027_redirect_typescript.ts.out",
-  http_server: true,
-});
-
-itest!(_027_redirect_typescript_vendor_dir {
-  args:
-    "run --quiet --reload --vendor --allow-import $TESTDATA/run/027_redirect_typescript.ts",
-  output: "run/027_redirect_typescript.ts.out",
-  http_server: true,
-  temp_cwd: true,
-});
-
-itest!(_028_args {
-  args:
-    "run --quiet --reload run/028_args.ts --arg1 val1 --arg2=val2 -- arg3 arg4",
-  output: "run/028_args.ts.out",
-});
-
-itest!(_033_import_map_remote {
-  args:
-    "run --quiet --reload --allow-import --import-map=http://127.0.0.1:4545/import_maps/import_map_remote.json import_maps/test_remote.ts",
-  output: "run/033_import_map_remote.out",
-  http_server: true,
-});
-
-itest!(_033_import_map_vendor_dir_remote {
-  args:
-    "run --quiet --reload --allow-import --import-map=http://127.0.0.1:4545/import_maps/import_map_remote.json --vendor $TESTDATA/import_maps/test_remote.ts",
-  output: "run/033_import_map_remote.out",
-  http_server: true,
-  temp_cwd: true,
-});
-
-itest!(_033_import_map_data_uri {
-  args:
-    "run --quiet --reload --allow-import --import-map=data:application/json;charset=utf-8;base64,ewogICJpbXBvcnRzIjogewogICAgInRlc3Rfc2VydmVyLyI6ICJodHRwOi8vbG9jYWxob3N0OjQ1NDUvIgogIH0KfQ== run/import_maps/test_data.ts",
-  output: "run/import_maps/test_data.ts.out",
-  http_server: true,
-});
-
-itest!(onload {
-  args: "run --quiet --reload --config ../config/deno.json run/onload/main.ts",
-  output: "run/onload/main.out",
-});
-
-itest!(_035_cached_only_flag {
-  args: "run --reload --check --allow-import --cached-only http://127.0.0.1:4545/run/019_media_types.ts",
-  output: "run/035_cached_only_flag.out",
-  exit_code: 1,
-  http_server: true,
-});
-
-itest!(_038_checkjs {
-  // checking if JS file is run through TS compiler
-  args:
-    "run --reload --config run/checkjs.tsconfig.json --check run/038_checkjs.js",
-  exit_code: 1,
-  output: "run/038_checkjs.js.out",
-});
-
-itest!(_042_dyn_import_evalcontext {
-  args: "run --quiet --allow-read --reload run/042_dyn_import_evalcontext.ts",
-  output: "run/042_dyn_import_evalcontext.ts.out",
-});
-
-itest!(_044_bad_resource {
-  args: "run --quiet --reload --allow-read run/044_bad_resource.ts",
-  output: "run/044_bad_resource.ts.out",
-  exit_code: 1,
-});
-
-itest!(_046_tsx {
-  args: "run --quiet --reload run/046_jsx_test.tsx",
-  output: "run/046_jsx_test.tsx.out",
-});
-
-itest!(_047_jsx {
-  args: "run --quiet --reload run/047_jsx_test.jsx",
-  output: "run/047_jsx_test.jsx.out",
-});
-
-itest!(_048_media_types_jsx {
-  args: "run  --reload --allow-import run/048_media_types_jsx.ts",
-  output: "run/048_media_types_jsx.ts.out",
-  http_server: true,
-});
-
-itest!(_052_no_remote_flag {
-  args:
-    "run --reload --check --allow-import --no-remote http://127.0.0.1:4545/run/019_media_types.ts",
-  output: "run/052_no_remote_flag.out",
-  exit_code: 1,
-  http_server: true,
-});
-
-itest!(_058_tasks_microtasks_close {
-  args: "run --quiet run/058_tasks_microtasks_close.ts",
-  output: "run/058_tasks_microtasks_close.ts.out",
-});
-
-itest!(_059_fs_relative_path_perm {
-  args: "run run/059_fs_relative_path_perm.ts",
-  output: "run/059_fs_relative_path_perm.ts.out",
-  exit_code: 1,
-});
-
-itest!(_070_location {
-  args: "run --location https://foo/bar?baz#bat run/070_location.ts",
-  output: "run/070_location.ts.out",
-});
-
-itest!(_071_location_unset {
-  args: "run run/071_location_unset.ts",
-  output: "run/071_location_unset.ts.out",
-});
-
-itest!(_072_location_relative_fetch {
-  args: "run --location http://127.0.0.1:4545/ --allow-net run/072_location_relative_fetch.ts",
-  output: "run/072_location_relative_fetch.ts.out",
-  http_server: true,
-});
-
-// tests the beforeunload event
-itest!(beforeunload_event {
-  args: "run run/before_unload.js",
-  output: "run/before_unload.js.out",
-});
-
-// tests the serialization of webstorage (both localStorage and sessionStorage)
-itest!(webstorage_serialization {
-  args: "run run/webstorage/serialization.ts",
-  output: "run/webstorage/serialization.ts.out",
-});
-
 // tests to ensure that when `--location` is set, all code shares the same
 // localStorage cache based on the origin of the location URL.
 #[test]
@@ -394,41 +133,6 @@ fn webstorage_main_module() {
     .assert_matches_text("Storage { hello: \"deno\", length: 1 }\n");
 }
 
-itest!(_075_import_local_query_hash {
-  args: "run run/075_import_local_query_hash.ts",
-  output: "run/075_import_local_query_hash.ts.out",
-});
-
-itest!(_077_fetch_empty {
-  args: "run -A run/077_fetch_empty.ts",
-  output: "run/077_fetch_empty.ts.out",
-  exit_code: 1,
-});
-
-itest!(_078_unload_on_exit {
-  args: "run run/078_unload_on_exit.ts",
-  output: "run/078_unload_on_exit.ts.out",
-  exit_code: 1,
-});
-
-itest!(_079_location_authentication {
-  args:
-    "run --location https://foo:bar@baz/qux run/079_location_authentication.ts",
-  output: "run/079_location_authentication.ts.out",
-});
-
-itest!(_081_location_relative_fetch_redirect {
-    args: "run --location http://127.0.0.1:4546/ --allow-net run/081_location_relative_fetch_redirect.ts",
-    output: "run/081_location_relative_fetch_redirect.ts.out",
-    http_server: true,
-  });
-
-itest!(_082_prepare_stack_trace_throw {
-  args: "run run/082_prepare_stack_trace_throw.js",
-  output: "run/082_prepare_stack_trace_throw.js.out",
-  exit_code: 1,
-});
-
 #[test]
 fn _083_legacy_external_source_map() {
   let _g = util::http_server();
@@ -457,27 +161,6 @@ fn _083_legacy_external_source_map() {
   assert_eq!(out, "");
 }
 
-itest!(dynamic_import_async_error {
-  args: "run --allow-read run/dynamic_import_async_error/main.ts",
-  output: "run/dynamic_import_async_error/main.out",
-});
-
-itest!(dynamic_import_already_rejected {
-  args: "run --allow-read run/dynamic_import_already_rejected/main.ts",
-  output: "run/dynamic_import_already_rejected/main.out",
-});
-
-itest!(dynamic_import_concurrent_non_statically_analyzable {
-  args: "run --allow-import --allow-read --allow-net --quiet run/dynamic_import_concurrent_non_statically_analyzable/main.ts",
-  output: "run/dynamic_import_concurrent_non_statically_analyzable/main.out",
-  http_server: true,
-});
-
-itest!(_088_dynamic_import_already_evaluating {
-  args: "run --allow-read run/088_dynamic_import_already_evaluating.ts",
-  output: "run/088_dynamic_import_already_evaluating.ts.out",
-});
-
 itest!(_089_run_allow_list {
   args: "run --allow-run=curl run/089_run_allow_list.ts",
   envs: vec![
@@ -713,16 +396,6 @@ fn permission_request_long() {
     });
 }
 
-itest!(deny_all_permission_args {
-  args: "run --deny-env --deny-read --deny-write --deny-ffi --deny-run --deny-sys --deny-net run/deny_all_permission_args.js",
-  output: "run/deny_all_permission_args.out",
-});
-
-itest!(deny_some_permission_args {
-  args: "run --allow-env --deny-env=FOO --allow-read --deny-read=/foo --allow-write --deny-write=/foo --allow-ffi --deny-ffi=/foo --allow-run --deny-run=foo --allow-sys --deny-sys=hostname --allow-net --deny-net=127.0.0.1 run/deny_some_permission_args.js",
-  output: "run/deny_some_permission_args.out",
-});
-
 #[test]
 fn permissions_cache() {
   TestContext::default()
@@ -755,52 +428,6 @@ itest!(env_file_missing {
   output: "run/env_file_missing.out",
 });
 
-itest!(_091_use_define_for_class_fields {
-  args: "run --check run/091_use_define_for_class_fields.ts",
-  output: "run/091_use_define_for_class_fields.ts.out",
-  exit_code: 1,
-});
-
-itest!(js_import_detect {
-  args: "run --quiet --reload run/js_import_detect.ts",
-  output: "run/js_import_detect.ts.out",
-  exit_code: 0,
-});
-
-itest!(blob_gc_finalization {
-  args: "run run/blob_gc_finalization.js",
-  output: "run/blob_gc_finalization.js.out",
-  exit_code: 0,
-});
-
-itest!(fetch_response_finalization {
-  args:
-    "run --v8-flags=--expose-gc --allow-net run/fetch_response_finalization.js",
-  output: "run/fetch_response_finalization.js.out",
-  http_server: true,
-  exit_code: 0,
-});
-
-itest!(import_type {
-  args: "run --reload run/import_type.ts",
-  output: "run/import_type.ts.out",
-});
-
-itest!(import_type_no_check {
-  args: "run --reload --no-check run/import_type.ts",
-  output: "run/import_type.ts.out",
-});
-
-itest!(private_field_presence {
-  args: "run --reload run/private_field_presence.ts",
-  output: "run/private_field_presence.ts.out",
-});
-
-itest!(private_field_presence_no_check {
-  args: "run --reload --no-check run/private_field_presence.ts",
-  output: "run/private_field_presence.ts.out",
-});
-
 itest!(lock_write_fetch {
   args:
     "run --quiet --allow-import --allow-read --allow-write --allow-env --allow-run run/lock_write_fetch/main.ts",
@@ -809,33 +436,6 @@ itest!(lock_write_fetch {
   exit_code: 0,
 });
 
-itest!(lock_check_ok {
-  args:
-    "run --quiet --allow-import --lock=run/lock_check_ok.json http://127.0.0.1:4545/run/003_relative_import.ts",
-  output: "run/003_relative_import.ts.out",
-  http_server: true,
-});
-
-itest!(lock_check_ok2 {
-  args:
-    "run --allow-import --lock=run/lock_check_ok2.json run/019_media_types.ts",
-  output: "run/019_media_types.ts.out",
-  http_server: true,
-});
-
-itest!(lock_v2_check_ok {
-  args:
-    "run --allow-import --quiet --lock=run/lock_v2_check_ok.json http://127.0.0.1:4545/run/003_relative_import.ts",
-  output: "run/003_relative_import.ts.out",
-  http_server: true,
-});
-
-itest!(lock_v2_check_ok2 {
-  args: "run --allow-import --lock=run/lock_v2_check_ok2.json run/019_media_types.ts",
-  output: "run/019_media_types.ts.out",
-  http_server: true,
-});
-
 #[test]
 fn lock_redirects() {
   let context = TestContextBuilder::new()
@@ -898,7 +498,7 @@ fn lock_redirects() {
     .run()
     .assert_matches_text(concat!(
       "Download http://localhost:4545/echo.ts\n",
-      "Download http://localhost:4260/@denotest/esm-basic\n",
+      "Download http://localhost:4260/@denotest%2fesm-basic\n",
       "Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz\n",
       "Hi, there",
     ));
@@ -926,9 +526,7 @@ fn lock_redirects() {
   );
 }
 
-// TODO(2.0): this should be rewritten to a spec test and first run `deno install`
 #[test]
-#[ignore]
 fn lock_deno_json_package_json_deps() {
   let context = TestContextBuilder::new()
     .use_temp_cwd()
@@ -942,6 +540,7 @@ fn lock_deno_json_package_json_deps() {
 
   // add a jsr and npm dependency
   deno_json.write_json(&json!({
+    "nodeModulesDir": "auto",
     "imports": {
       "esm-basic": "npm:@denotest/esm-basic",
       "module_graph": "jsr:@denotest/module-graph@1.4",
@@ -984,6 +583,7 @@ fn lock_deno_json_package_json_deps() {
   // now remove the npm dependency from the deno.json and move
   // it to a package.json that uses an alias
   deno_json.write_json(&json!({
+    "nodeModulesDir": "auto",
     "imports": {
       "module_graph": "jsr:@denotest/module-graph@1.4",
     }
@@ -1060,7 +660,9 @@ fn lock_deno_json_package_json_deps() {
   }));
 
   // now remove the deps from the deno.json
-  deno_json.write("{}");
+  deno_json.write_json(&json!({
+    "nodeModulesDir": "auto"
+  }));
   main_ts.write("");
   context
     .new_command()
@@ -1232,141 +834,12 @@ fn get_lockfile_npm_package_integrity(
     .to_string()
 }
 
-itest!(mts_dmts_mjs {
-  args: "run subdir/import.mts",
-  output: "run/mts_dmts_mjs.out",
-});
-
-itest!(mts_dmts_mjs_no_check {
-  args: "run --no-check subdir/import.mts",
-  output: "run/mts_dmts_mjs.out",
-});
-
-itest!(async_error {
-  exit_code: 1,
-  args: "run --reload run/async_error.ts",
-  output: "run/async_error.ts.out",
-});
-
-itest!(config {
-  args:
-    "run --reload --config run/config/tsconfig.json --check run/config/main.ts",
-  output: "run/config/main.out",
-});
-
-itest!(config_types {
-  args:
-    "run --reload --quiet --check=all --config run/config_types/tsconfig.json run/config_types/main.ts",
-  output: "run/config_types/main.out",
-});
-
-itest!(config_types_remote {
-  http_server: true,
-  args: "run --allow-import --reload --quiet --check=all --config run/config_types/remote.tsconfig.json run/config_types/main.ts",
-  output: "run/config_types/main.out",
-});
-
-itest!(empty_typescript {
-  args: "run --reload --check run/empty.ts",
-  output_str: Some("Check file:[WILDCARD]/run/empty.ts\n"),
-});
-
-itest!(error_001 {
-  args: "run --reload run/error_001.ts",
-  exit_code: 1,
-  output: "run/error_001.ts.out",
-});
-
-itest!(error_002 {
-  args: "run --reload run/error_002.ts",
-  exit_code: 1,
-  output: "run/error_002.ts.out",
-});
-
-itest!(error_003_typescript {
-  args: "run --reload --check run/error_003_typescript.ts",
-  exit_code: 1,
-  output: "run/error_003_typescript.ts.out",
-});
-
-// Supposing that we've already attempted to run error_003_typescript.ts
-// we want to make sure that JS wasn't emitted. Running again without reload flag
-// should result in the same output.
-// https://github.com/denoland/deno/issues/2436
-itest!(error_003_typescript2 {
-  args: "run --check run/error_003_typescript.ts",
-  exit_code: 1,
-  output: "run/error_003_typescript.ts.out",
-});
-
-itest!(error_004_missing_module {
-  args: "run --reload run/error_004_missing_module.ts",
-  exit_code: 1,
-  output: "run/error_004_missing_module.ts.out",
-});
-
-itest!(error_005_missing_dynamic_import {
-  args:
-    "run --reload --allow-read --quiet run/error_005_missing_dynamic_import.ts",
-  exit_code: 1,
-  output: "run/error_005_missing_dynamic_import.ts.out",
-});
-
-itest!(error_006_import_ext_failure {
-  args: "run --reload run/error_006_import_ext_failure.ts",
-  exit_code: 1,
-  output: "run/error_006_import_ext_failure.ts.out",
-});
-
-itest!(error_007_any {
-  args: "run --reload run/error_007_any.ts",
-  exit_code: 1,
-  output: "run/error_007_any.ts.out",
-});
-
-itest!(error_008_checkjs {
-  args: "run --reload run/error_008_checkjs.js",
-  exit_code: 1,
-  output: "run/error_008_checkjs.js.out",
-});
-
-itest!(error_009_extensions_error {
-  args: "run run/error_009_extensions_error.js",
-  output: "run/error_009_extensions_error.js.out",
-  exit_code: 1,
-});
-
-itest!(error_011_bad_module_specifier {
-  args: "run --reload run/error_011_bad_module_specifier.ts",
-  exit_code: 1,
-  output: "run/error_011_bad_module_specifier.ts.out",
-});
-
-itest!(error_012_bad_dynamic_import_specifier {
-  args: "run --reload --check run/error_012_bad_dynamic_import_specifier.ts",
-  exit_code: 1,
-  output: "run/error_012_bad_dynamic_import_specifier.ts.out",
-});
-
 itest!(error_013_missing_script {
   args: "run --reload missing_file_name",
   exit_code: 1,
   output: "run/error_013_missing_script.out",
 });
 
-itest!(error_014_catch_dynamic_import_error {
-  args:
-    "run  --reload --allow-read run/error_014_catch_dynamic_import_error.js",
-  output: "run/error_014_catch_dynamic_import_error.js.out",
-});
-
-itest!(error_015_dynamic_import_permissions {
-  args: "run --reload --quiet run/error_015_dynamic_import_permissions.js",
-  output: "run/error_015_dynamic_import_permissions.out",
-  exit_code: 1,
-  http_server: true,
-});
-
 // We have an allow-import flag but not allow-read, it should still result in error.
 itest!(error_016_dynamic_import_permissions2 {
   args:
@@ -1376,60 +849,6 @@ itest!(error_016_dynamic_import_permissions2 {
   http_server: true,
 });
 
-itest!(error_017_hide_long_source_ts {
-  args: "run --reload --check run/error_017_hide_long_source_ts.ts",
-  output: "run/error_017_hide_long_source_ts.ts.out",
-  exit_code: 1,
-});
-
-itest!(error_018_hide_long_source_js {
-  args: "run run/error_018_hide_long_source_js.js",
-  output: "run/error_018_hide_long_source_js.js.out",
-  exit_code: 1,
-});
-
-itest!(error_019_stack_function {
-  args: "run run/error_019_stack_function.ts",
-  output: "run/error_019_stack_function.ts.out",
-  exit_code: 1,
-});
-
-itest!(error_020_stack_constructor {
-  args: "run run/error_020_stack_constructor.ts",
-  output: "run/error_020_stack_constructor.ts.out",
-  exit_code: 1,
-});
-
-itest!(error_021_stack_method {
-  args: "run run/error_021_stack_method.ts",
-  output: "run/error_021_stack_method.ts.out",
-  exit_code: 1,
-});
-
-itest!(error_022_stack_custom_error {
-  args: "run run/error_022_stack_custom_error.ts",
-  output: "run/error_022_stack_custom_error.ts.out",
-  exit_code: 1,
-});
-
-itest!(error_023_stack_async {
-  args: "run run/error_023_stack_async.ts",
-  output: "run/error_023_stack_async.ts.out",
-  exit_code: 1,
-});
-
-itest!(error_024_stack_promise_all {
-  args: "run run/error_024_stack_promise_all.ts",
-  output: "run/error_024_stack_promise_all.ts.out",
-  exit_code: 1,
-});
-
-itest!(error_025_tab_indent {
-  args: "run run/error_025_tab_indent",
-  output: "run/error_025_tab_indent.out",
-  exit_code: 1,
-});
-
 itest!(error_026_remote_import_error {
   args: "run --allow-import run/error_026_remote_import_error.ts",
   output: "run/error_026_remote_import_error.ts.out",
@@ -1437,42 +856,6 @@ itest!(error_026_remote_import_error {
   http_server: true,
 });
 
-itest!(error_for_await {
-  args: "run --reload --check run/error_for_await.ts",
-  output: "run/error_for_await.ts.out",
-  exit_code: 1,
-});
-
-itest!(error_missing_module_named_import {
-  args: "run --reload run/error_missing_module_named_import.ts",
-  output: "run/error_missing_module_named_import.ts.out",
-  exit_code: 1,
-});
-
-itest!(error_no_check {
-  args: "run --reload --no-check run/error_no_check.ts",
-  output: "run/error_no_check.ts.out",
-  exit_code: 1,
-});
-
-itest!(error_syntax {
-  args: "run --reload run/error_syntax.js",
-  exit_code: 1,
-  output: "run/error_syntax.js.out",
-});
-
-itest!(error_syntax_empty_trailing_line {
-  args: "run --reload run/error_syntax_empty_trailing_line.mjs",
-  exit_code: 1,
-  output: "run/error_syntax_empty_trailing_line.mjs.out",
-});
-
-itest!(error_type_definitions {
-  args: "run --reload --check run/error_type_definitions.ts",
-  exit_code: 1,
-  output: "run/error_type_definitions.ts.out",
-});
-
 itest!(error_local_static_import_from_remote_ts {
   args: "run --allow-import --reload http://localhost:4545/run/error_local_static_import_from_remote.ts",
   exit_code: 1,
@@ -1487,138 +870,18 @@ itest!(error_local_static_import_from_remote_js {
   output: "run/error_local_static_import_from_remote.js.out",
 });
 
-itest!(exit_error42 {
-  exit_code: 42,
-  args: "run --quiet --reload run/exit_error42.ts",
-  output: "run/exit_error42.ts.out",
-});
-
-itest!(set_exit_code_0 {
-  args: "run --no-check run/set_exit_code_0.ts",
-  output_str: Some(""),
-  exit_code: 0,
-});
-
-itest!(set_exit_code_1 {
-  args: "run --no-check run/set_exit_code_1.ts",
-  output_str: Some(""),
-  exit_code: 42,
-});
-
-itest!(set_exit_code_2 {
-  args: "run --no-check run/set_exit_code_2.ts",
-  output_str: Some(""),
-  exit_code: 42,
-});
-
-itest!(op_exit_op_set_exit_code_in_worker {
-  args: "run --no-check --allow-read run/op_exit_op_set_exit_code_in_worker.ts",
-  exit_code: 21,
-  output_str: Some(""),
-});
-
-itest!(deno_exit_tampering {
-  args: "run --no-check run/deno_exit_tampering.ts",
-  output_str: Some(""),
-  exit_code: 42,
-});
-
-itest!(heapstats {
-  args: "run --quiet --v8-flags=--expose-gc run/heapstats.js",
-  output: "run/heapstats.js.out",
-});
-
-itest!(finalization_registry {
-  args: "run --quiet --v8-flags=--expose-gc run/finalization_registry.js",
-  output: "run/finalization_registry.js.out",
-});
-
-itest!(https_import {
-  args: "run --allow-import --quiet --reload --cert tls/RootCA.pem run/https_import.ts",
-  output: "run/https_import.ts.out",
-  http_server: true,
-});
-
-itest!(if_main {
-  args: "run --quiet --reload run/if_main.ts",
-  output: "run/if_main.ts.out",
-});
-
 itest!(import_meta {
   args: "run --allow-import --quiet --reload --import-map=run/import_meta/importmap.json run/import_meta/main.ts",
   output: "run/import_meta/main.out",
   http_server: true,
 });
 
-itest!(main_module {
-  args: "run --quiet --reload run/main_module/main.ts",
-  output: "run/main_module/main.out",
-});
-
-itest!(no_check {
-  args: "run --allow-import --quiet --reload --no-check run/006_url_imports.ts",
-  output: "run/006_url_imports.ts.out",
-  http_server: true,
-});
-
-itest!(no_check_decorators {
-  args: "run --quiet --reload --no-check run/decorators/experimental/no_check/main.ts",
-  output: "run/decorators/experimental/no_check/main.out",
-});
-
-itest!(decorators_tc39_proposal {
-  args: "run --quiet --reload --check run/decorators/tc39_proposal/main.ts",
-  output: "run/decorators/tc39_proposal/main.out",
-});
-
-itest!(check_remote {
-  args:
-    "run --quiet --allow-import --reload --check=all run/no_check_remote.ts",
-  output: "run/no_check_remote.ts.disabled.out",
-  exit_code: 1,
-  http_server: true,
-});
-
 itest!(no_check_remote {
   args: "run --allow-import --quiet --reload --no-check=remote run/no_check_remote.ts",
   output: "run/no_check_remote.ts.enabled.out",
   http_server: true,
 });
 
-itest!(runtime_decorators {
-  args: "run --quiet --reload --no-check run/decorators/experimental/runtime/main.ts",
-  output: "run/decorators/experimental/runtime/main.out",
-});
-
-itest!(seed_random {
-  args: "run --seed=100 run/seed_random.js",
-  output: "run/seed_random.js.out",
-});
-
-itest!(type_definitions {
-  args: "run --reload run/type_definitions.ts",
-  output: "run/type_definitions.ts.out",
-});
-
-itest!(type_definitions_for_export {
-  args: "run --reload --check run/type_definitions_for_export.ts",
-  output: "run/type_definitions_for_export.ts.out",
-  exit_code: 1,
-});
-
-itest!(type_directives_01 {
-  args:
-    "run --allow-import --reload --check=all -L debug run/type_directives_01.ts",
-  output: "run/type_directives_01.ts.out",
-  http_server: true,
-});
-
-itest!(type_directives_02 {
-  args:
-    "run --allow-import --reload --check=all -L debug run/type_directives_02.ts",
-  output: "run/type_directives_02.ts.out",
-});
-
 #[test]
 fn type_directives_js_main() {
   let context = TestContext::default();
@@ -1640,216 +903,6 @@ itest!(type_directives_redirect {
   http_server: true,
 });
 
-itest!(type_headers_deno_types {
-  args: "run --allow-import --reload --check run/type_headers_deno_types.ts",
-  output: "run/type_headers_deno_types.ts.out",
-  http_server: true,
-});
-
-itest!(ts_type_imports {
-  args: "run --reload --check run/ts_type_imports.ts",
-  output: "run/ts_type_imports.ts.out",
-  exit_code: 1,
-});
-
-itest!(ts_decorators {
-  args: "run --reload --check run/decorators/experimental/ts/main.ts",
-  output: "run/decorators/experimental/ts/main.out",
-});
-
-itest!(ts_type_only_import {
-  args: "run --reload --check run/ts_type_only_import.ts",
-  output: "run/ts_type_only_import.ts.out",
-});
-
-itest!(swc_syntax_error {
-  args: "run --reload --check run/swc_syntax_error.ts",
-  output: "run/swc_syntax_error.ts.out",
-  exit_code: 1,
-});
-
-itest!(unbuffered_stderr {
-  args: "run --reload run/unbuffered_stderr.ts",
-  output: "run/unbuffered_stderr.ts.out",
-});
-
-itest!(unbuffered_stdout {
-  args: "run --quiet --reload run/unbuffered_stdout.ts",
-  output: "run/unbuffered_stdout.ts.out",
-});
-
-itest!(v8_flags_run {
-  args: "run --v8-flags=--expose-gc run/v8_flags.js",
-  output: "run/v8_flags.js.out",
-});
-
-itest!(v8_flags_env_run {
-  envs: vec![("DENO_V8_FLAGS".to_string(), "--expose-gc".to_string())],
-  args: "run run/v8_flags.js",
-  output: "run/v8_flags.js.out",
-});
-
-itest!(v8_flags_unrecognized {
-  args: "repl --v8-flags=--foo,bar,--trace-gc,-baz",
-  output: "run/v8_flags_unrecognized.out",
-  exit_code: 1,
-});
-
-itest!(v8_help {
-  args: "repl --v8-flags=--help",
-  output: "run/v8_help.out",
-});
-
-itest!(unsupported_dynamic_import_scheme {
-  args: "eval import('xxx:')",
-  output: "run/unsupported_dynamic_import_scheme.out",
-  exit_code: 1,
-});
-
-itest!(wasm {
-  args: "run --quiet run/wasm.ts",
-  output: "run/wasm.ts.out",
-});
-
-itest!(wasm_shared {
-  args: "run --quiet run/wasm_shared.ts",
-  output: "run/wasm_shared.out",
-});
-
-itest!(wasm_async {
-  args: "run run/wasm_async.js",
-  output: "run/wasm_async.out",
-});
-
-itest!(wasm_unreachable {
-  args: "run --allow-read run/wasm_unreachable.js",
-  output: "run/wasm_unreachable.out",
-  exit_code: 1,
-});
-
-itest!(wasm_url {
-  args: "run --quiet --allow-net=localhost:4545 run/wasm_url.js",
-  output: "run/wasm_url.out",
-  exit_code: 1,
-  http_server: true,
-});
-
-itest!(weakref {
-  args: "run --quiet --reload run/weakref.ts",
-  output: "run/weakref.ts.out",
-});
-
-itest!(top_level_await_order {
-  args: "run --allow-read run/top_level_await/order.js",
-  output: "run/top_level_await/order.out",
-});
-
-itest!(top_level_await_loop {
-  args: "run --allow-read run/top_level_await/loop.js",
-  output: "run/top_level_await/loop.out",
-});
-
-itest!(top_level_await_circular {
-  args: "run --allow-read run/top_level_await/circular.js",
-  output: "run/top_level_await/circular.out",
-  exit_code: 1,
-});
-
-// Regression test for https://github.com/denoland/deno/issues/11238.
-itest!(top_level_await_nested {
-  args: "run --allow-read run/top_level_await/nested/main.js",
-  output: "run/top_level_await/nested.out",
-});
-
-itest!(top_level_await_unresolved {
-  args: "run run/top_level_await/unresolved.js",
-  output: "run/top_level_await/unresolved.out",
-  exit_code: 1,
-});
-
-itest!(top_level_await {
-  args: "run --allow-read run/top_level_await/top_level_await.js",
-  output: "run/top_level_await/top_level_await.out",
-});
-
-itest!(top_level_await_ts {
-  args: "run --quiet --allow-read run/top_level_await/top_level_await.ts",
-  output: "run/top_level_await/top_level_await.out",
-});
-
-itest!(top_level_for_await {
-  args: "run --quiet run/top_level_await/top_level_for_await.js",
-  output: "run/top_level_await/top_level_for_await.out",
-});
-
-itest!(top_level_for_await_ts {
-  args: "run --quiet run/top_level_await/top_level_for_await.ts",
-  output: "run/top_level_await/top_level_for_await.out",
-});
-
-itest!(unstable_worker {
-  args: "run --reload --quiet --allow-read run/unstable_worker.ts",
-  output: "run/unstable_worker.ts.out",
-});
-
-itest!(unstable_worker_options_disabled {
-  args: "run --quiet --reload --allow-read run/unstable_worker_options.js",
-  output: "run/unstable_worker_options.disabled.out",
-  exit_code: 70,
-});
-
-itest!(unstable_worker_options_enabled {
-  args: "run --quiet --reload --allow-read --unstable-worker-options run/unstable_worker_options.js",
-  output: "run/unstable_worker_options.enabled.out",
-});
-
-itest!(unstable_broadcast_channel_disabled {
-  args: "run --quiet --reload --allow-read run/unstable_broadcast_channel.js",
-  output: "run/unstable_broadcast_channel.disabled.out",
-});
-
-itest!(unstable_broadcast_channel_enabled {
-  args: "run --quiet --reload --allow-read --unstable-broadcast-channel run/unstable_broadcast_channel.js",
-  output: "run/unstable_broadcast_channel.enabled.out",
-});
-
-itest!(unstable_cron_disabled {
-  args: "run --quiet --reload --allow-read run/unstable_cron.js",
-  output: "run/unstable_cron.disabled.out",
-});
-
-itest!(unstable_cron_enabled {
-  args:
-    "run --quiet --reload --allow-read --unstable-cron run/unstable_cron.js",
-  output: "run/unstable_cron.enabled.out",
-});
-
-itest!(unstable_net_disabled {
-  args: "run --quiet --reload --allow-read run/unstable_net.js",
-  output: "run/unstable_net.disabled.out",
-});
-
-itest!(unstable_net_enabled {
-  args: "run --quiet --reload --allow-read --unstable-net run/unstable_net.js",
-  output: "run/unstable_net.enabled.out",
-});
-
-itest!(unstable_kv_disabled {
-  args: "run --quiet --reload --allow-read run/unstable_kv.js",
-  output: "run/unstable_kv.disabled.out",
-});
-
-itest!(unstable_kv_enabled {
-  args: "run --quiet --reload --allow-read --unstable-kv run/unstable_kv.js",
-  output: "run/unstable_kv.enabled.out",
-});
-
-itest!(import_compression {
-  args: "run --allow-import --quiet --reload --allow-net run/import_compression/main.ts",
-  output: "run/import_compression/main.out",
-  http_server: true,
-});
-
 itest!(disallow_http_from_https_js {
   args: "run --allow-import --quiet --reload --cert tls/RootCA.pem https://localhost:5545/run/disallow_http_from_https.js",
   output: "run/disallow_http_from_https_js.out",
@@ -1864,131 +917,6 @@ itest!(disallow_http_from_https_ts {
   exit_code: 1,
 });
 
-itest!(dynamic_import_conditional {
-  args: "run --quiet --reload run/dynamic_import_conditional.js",
-  output: "run/dynamic_import_conditional.js.out",
-});
-
-itest!(tsx_imports {
-  args: "run --reload --check run/tsx_imports/tsx_imports.ts",
-  output: "run/tsx_imports/tsx_imports.ts.out",
-});
-
-itest!(fix_dynamic_import_errors {
-  args: "run --reload run/fix_dynamic_import_errors.js",
-  output: "run/fix_dynamic_import_errors.js.out",
-});
-
-itest!(fix_emittable_skipped {
-  args: "run --reload run/fix_emittable_skipped.js",
-  output: "run/fix_emittable_skipped.ts.out",
-});
-
-itest!(fix_js_import_js {
-  args: "run --quiet --reload run/fix_js_import_js.ts",
-  output: "run/fix_js_import_js.ts.out",
-});
-
-itest!(fix_js_imports {
-  args: "run --quiet --reload run/fix_js_imports.ts",
-  output: "run/fix_js_imports.ts.out",
-});
-
-itest!(fix_tsc_file_exists {
-  args: "run --quiet --reload tsc/test.js",
-  output: "run/fix_tsc_file_exists.out",
-});
-
-itest!(fix_worker_dispatchevent {
-  args: "run --quiet --reload run/fix_worker_dispatchevent.ts",
-  output: "run/fix_worker_dispatchevent.ts.out",
-});
-
-itest!(es_private_fields {
-  args: "run --quiet --reload run/es_private_fields.js",
-  output: "run/es_private_fields.js.out",
-});
-
-itest!(ts_import_from_js {
-  args: "run --allow-import --quiet --reload run/ts_import_from_js/main.js",
-  output: "run/ts_import_from_js/main.out",
-  http_server: true,
-});
-
-itest!(jsx_import_from_ts {
-  args: "run --quiet --reload run/jsx_import_from_ts.ts",
-  output: "run/jsx_import_from_ts.ts.out",
-});
-
-itest!(jsx_import_source_pragma {
-  args: "run --reload --allow-import run/jsx_import_source_pragma.tsx",
-  output: "run/jsx_import_source.out",
-  http_server: true,
-});
-
-itest!(jsx_import_source_pragma_with_config {
-  args:
-    "run --reload --allow-import --config jsx/deno-jsx.jsonc --no-lock run/jsx_import_source_pragma.tsx",
-  output: "run/jsx_import_source.out",
-  http_server: true,
-});
-
-itest!(jsx_import_source_pragma_with_dev_config {
-  args:
-    "run --reload --allow-import --config jsx/deno-jsxdev.jsonc --no-lock run/jsx_import_source_pragma.tsx",
-  output: "run/jsx_import_source_dev.out",
-  http_server: true,
-});
-
-itest!(jsx_import_source_no_pragma {
-  args:
-    "run --allow-import --reload --config jsx/deno-jsx.jsonc --no-lock run/jsx_import_source_no_pragma.tsx",
-  output: "run/jsx_import_source.out",
-  http_server: true,
-});
-
-itest!(jsx_import_source_no_pragma_dev {
-  args: "run --allow-import --reload --config jsx/deno-jsxdev.jsonc --no-lock run/jsx_import_source_no_pragma.tsx",
-  output: "run/jsx_import_source_dev.out",
-  http_server: true,
-});
-
-itest!(jsx_import_source_pragma_import_map {
-  args: "run --allow-import --reload --import-map jsx/import-map.json run/jsx_import_source_pragma_import_map.tsx",
-  output: "run/jsx_import_source_import_map.out",
-  http_server: true,
-});
-
-itest!(jsx_import_source_pragma_import_map_dev {
-  args: "run --allow-import --reload --import-map jsx/import-map.json --config jsx/deno-jsxdev-import-map.jsonc run/jsx_import_source_pragma_import_map.tsx",
-  output: "run/jsx_import_source_import_map_dev.out",
-  http_server: true,
-});
-
-itest!(jsx_import_source_precompile_import_map {
-  args: "run --allow-import --reload --check --import-map jsx/import-map.json --no-lock --config jsx/deno-jsx-precompile.jsonc run/jsx_precompile/no_pragma.tsx",
-  output: "run/jsx_precompile/no_pragma.out",
-  http_server: true,
-});
-
-itest!(jsx_import_source_precompile_import_map_skip_element {
-  args: "run --allow-import --reload --check --import-map jsx/import-map.json --no-lock --config jsx/deno-jsx-precompile-skip.jsonc run/jsx_precompile/skip.tsx",
-  output: "run/jsx_precompile/skip.out",
-  http_server: true,
-});
-
-itest!(jsx_import_source_import_map {
-  args: "run --allow-import --reload --import-map jsx/import-map.json --no-lock --config jsx/deno-jsx-import-map.jsonc run/jsx_import_source_no_pragma.tsx",
-  output: "run/jsx_import_source_import_map.out",
-  http_server: true,
-});
-
-itest!(jsx_import_source_import_map_dev {
-  args: "run --allow-import --reload --import-map jsx/import-map.json --no-lock --config jsx/deno-jsxdev-import-map.jsonc run/jsx_import_source_no_pragma.tsx",
-  output: "run/jsx_import_source_import_map_dev.out",
-  http_server: true,
-});
-
 itest!(jsx_import_source_import_map_scoped {
   args: "run --allow-import --reload --import-map jsx/import-map-scoped.json --no-lock --config jsx/deno-jsx-import-map.jsonc subdir/jsx_import_source_no_pragma.tsx",
   output: "run/jsx_import_source_import_map.out",
@@ -2001,289 +929,12 @@ itest!(jsx_import_source_import_map_scoped_dev {
   http_server: true,
 });
 
-itest!(jsx_import_source_pragma_no_check {
-  args:
-    "run --allow-import --reload --no-check run/jsx_import_source_pragma.tsx",
-  output: "run/jsx_import_source.out",
-  http_server: true,
-});
-
-itest!(jsx_import_source_pragma_with_config_no_check {
-  args: "run --allow-import --reload --config jsx/deno-jsx.jsonc --no-lock --no-check run/jsx_import_source_pragma.tsx",
-  output: "run/jsx_import_source.out",
-  http_server: true,
-});
-
-itest!(jsx_import_source_pragma_with_config_vendor_dir {
-  args: "run --allow-import --reload --config jsx/deno-jsx.jsonc --no-lock --vendor $TESTDATA/run/jsx_import_source_pragma.tsx",
-  output: "run/jsx_import_source.out",
-  http_server: true,
-  temp_cwd: true,
-  copy_temp_dir: Some("jsx/"),
-});
-
-itest!(jsx_import_source_no_pragma_no_check {
-  args:
-    "run --allow-import --reload --config jsx/deno-jsx.jsonc --no-lock --no-check run/jsx_import_source_no_pragma.tsx",
-  output: "run/jsx_import_source.out",
-  http_server: true,
-});
-
-itest!(jsx_import_source_pragma_import_map_no_check {
-  args: "run --allow-import --reload --import-map jsx/import-map.json --no-check run/jsx_import_source_pragma_import_map.tsx",
-  output: "run/jsx_import_source_import_map.out",
-  http_server: true,
-});
-
-itest!(jsx_import_source_import_map_no_check {
-  args: "run --allow-import --reload --import-map jsx/import-map.json --no-lock --config jsx/deno-jsx-import-map.jsonc --no-check run/jsx_import_source_no_pragma.tsx",
-  output: "run/jsx_import_source_import_map.out",
-  http_server: true,
-});
-
-itest!(jsx_import_source_error {
-  args: "run --config jsx/deno-jsx-error.jsonc --check run/jsx_import_source_no_pragma.tsx",
-  output: "run/jsx_import_source_error.out",
-  exit_code: 1,
-});
-
-itest!(single_compile_with_reload {
-  args: "run --reload --allow-read run/single_compile_with_reload.ts",
-  output: "run/single_compile_with_reload.ts.out",
-});
-
-itest!(proto_exploit {
-  args: "run run/proto_exploit.js",
-  output: "run/proto_exploit.js.out",
-});
-
-itest!(reference_types {
-  args: "run --reload --quiet run/reference_types.ts",
-  output: "run/reference_types.ts.out",
-});
-
-itest!(references_types_remote {
-  http_server: true,
-  args: "run --reload --quiet run/reference_types_remote.ts",
-  output: "run/reference_types_remote.ts.out",
-});
-
-itest!(reference_types_error {
-  args:
-    "run --config run/checkjs.tsconfig.json --check run/reference_types_error.js",
-  output: "run/reference_types_error.js.out",
-  exit_code: 1,
-});
-
-itest!(reference_types_error_vendor_dir {
-  args:
-    "run --config run/checkjs.tsconfig.json --check --vendor $TESTDATA/run/reference_types_error.js",
-  output: "run/reference_types_error.js.out",
-  exit_code: 1,
-});
-
-itest!(reference_types_error_no_check {
-  args: "run --no-check run/reference_types_error.js",
-  output_str: Some(""),
-});
-
-itest!(import_data_url_error_stack {
-  args: "run --quiet --reload run/import_data_url_error_stack.ts",
-  output: "run/import_data_url_error_stack.ts.out",
-  exit_code: 1,
-});
-
-itest!(import_data_url_import_relative {
-  args: "run --quiet --reload run/import_data_url_import_relative.ts",
-  output: "run/import_data_url_import_relative.ts.out",
-  exit_code: 1,
-});
-
-itest!(import_data_url_imports {
-  args: "run --allow-import --quiet --reload run/import_data_url_imports.ts",
-  output: "run/import_data_url_imports.ts.out",
-  http_server: true,
-});
-
-itest!(import_data_url_jsx {
-  args: "run --quiet --reload run/import_data_url_jsx.ts",
-  output: "run/import_data_url_jsx.ts.out",
-});
-
-itest!(import_data_url {
-  args: "run --quiet --reload run/import_data_url.ts",
-  output: "run/import_data_url.ts.out",
-});
-
-itest!(import_dynamic_data_url {
-  args: "run --quiet --reload run/import_dynamic_data_url.ts",
-  output: "run/import_dynamic_data_url.ts.out",
-});
-
-itest!(import_blob_url_error_stack {
-  args: "run --quiet --reload run/import_blob_url_error_stack.ts",
-  output: "run/import_blob_url_error_stack.ts.out",
-  exit_code: 1,
-});
-
-itest!(import_blob_url_import_relative {
-  args: "run --quiet --reload run/import_blob_url_import_relative.ts",
-  output: "run/import_blob_url_import_relative.ts.out",
-  exit_code: 1,
-});
-
-itest!(import_blob_url_imports {
-  args:
-    "run --allow-import --quiet --reload --allow-net=localhost:4545 run/import_blob_url_imports.ts",
-  output: "run/import_blob_url_imports.ts.out",
-  http_server: true,
-});
-
-itest!(import_blob_url_jsx {
-  args: "run --quiet --reload run/import_blob_url_jsx.ts",
-  output: "run/import_blob_url_jsx.ts.out",
-});
-
-itest!(import_blob_url {
-  args: "run --quiet --reload run/import_blob_url.ts",
-  output: "run/import_blob_url.ts.out",
-});
-
-itest!(import_file_with_colon {
-  args: "run --allow-import --quiet --reload run/import_file_with_colon.ts",
-  output: "run/import_file_with_colon.ts.out",
-  http_server: true,
-});
-
-itest!(import_extensionless {
-  args: "run --allow-import --quiet --reload run/import_extensionless.ts",
-  output: "run/import_extensionless.ts.out",
-  http_server: true,
-});
-
-itest!(classic_workers_event_loop {
-  args:
-    "run --enable-testing-features-do-not-use run/classic_workers_event_loop.js",
-  output: "run/classic_workers_event_loop.js.out",
-});
-
 // FIXME(bartlomieju): disabled, because this test is very flaky on CI
 // itest!(local_sources_not_cached_in_memory {
 //   args: "run --allow-read --allow-write run/no_mem_cache.js",
 //   output: "run/no_mem_cache.js.out",
 // });
 
-// This test checks that inline source map data is used. It uses a hand crafted
-// source map that maps to a file that exists, but is not loaded into the module
-// graph (inline_js_source_map_2.ts) (because there are no direct dependencies).
-// Source line is not remapped because no inline source contents are included in
-// the sourcemap and the file is not present in the dependency graph.
-itest!(inline_js_source_map_2 {
-  args: "run --quiet run/inline_js_source_map_2.js",
-  output: "run/inline_js_source_map_2.js.out",
-  exit_code: 1,
-});
-
-// This test checks that inline source map data is used. It uses a hand crafted
-// source map that maps to a file that exists, but is not loaded into the module
-// graph (inline_js_source_map_2.ts) (because there are no direct dependencies).
-// Source line remapped using th inline source contents that are included in the
-// inline source map.
-itest!(inline_js_source_map_2_with_inline_contents {
-  args: "run --quiet run/inline_js_source_map_2_with_inline_contents.js",
-  output: "run/inline_js_source_map_2_with_inline_contents.js.out",
-  exit_code: 1,
-});
-
-// This test checks that inline source map data is used. It uses a hand crafted
-// source map that maps to a file that exists, and is loaded into the module
-// graph because of a direct import statement (inline_js_source_map.ts). The
-// source map was generated from an earlier version of this file, where the throw
-// was not commented out. The source line is remapped using source contents that
-// from the module graph.
-itest!(inline_js_source_map_with_contents_from_graph {
-  args: "run --allow-import --quiet run/inline_js_source_map_with_contents_from_graph.js",
-  output: "run/inline_js_source_map_with_contents_from_graph.js.out",
-  exit_code: 1,
-  http_server: true,
-});
-
-// This test ensures that a descriptive error is shown when we're unable to load
-// the import map. Even though this tests only the `run` subcommand, we can be sure
-// that the error message is similar for other subcommands as they all use
-// `program_state.maybe_import_map` to access the import map underneath.
-itest!(error_import_map_unable_to_load {
-  args: "run --import-map=import_maps/does_not_exist.json import_maps/test.ts",
-  output: "run/error_import_map_unable_to_load.out",
-  exit_code: 1,
-});
-
-// Test that setting `self` in the main thread to some other value doesn't break
-// the world.
-itest!(replace_self {
-  args: "run run/replace_self.js",
-  output: "run/replace_self.js.out",
-});
-
-itest!(worker_event_handler_test {
-  args: "run --quiet --reload --allow-read run/worker_event_handler_test.js",
-  output: "run/worker_event_handler_test.js.out",
-});
-
-itest!(worker_close_race {
-  args: "run --quiet --reload --allow-read run/worker_close_race.js",
-  output: "run/worker_close_race.js.out",
-});
-
-itest!(worker_drop_handle_race {
-  args: "run --quiet --reload --allow-read run/worker_drop_handle_race.js",
-  output: "run/worker_drop_handle_race.js.out",
-  exit_code: 1,
-});
-
-itest!(worker_drop_handle_race_terminate {
-  args: "run run/worker_drop_handle_race_terminate.js",
-  output: "run/worker_drop_handle_race_terminate.js.out",
-});
-
-itest!(worker_close_nested {
-  args: "run --quiet --reload --allow-read run/worker_close_nested.js",
-  output: "run/worker_close_nested.js.out",
-});
-
-itest!(worker_message_before_close {
-  args: "run --quiet --reload --allow-read run/worker_message_before_close.js",
-  output: "run/worker_message_before_close.js.out",
-});
-
-itest!(worker_close_in_wasm_reactions {
-  args:
-    "run --quiet --reload --allow-read run/worker_close_in_wasm_reactions.js",
-  output: "run/worker_close_in_wasm_reactions.js.out",
-});
-
-itest!(shebang_tsc {
-  args: "run --quiet --check run/shebang.ts",
-  output: "run/shebang.ts.out",
-});
-
-itest!(shebang_swc {
-  args: "run --quiet run/shebang.ts",
-  output: "run/shebang.ts.out",
-});
-
-itest!(shebang_with_json_imports_tsc {
-  args: "run --quiet import_attributes/json_with_shebang.ts",
-  output: "import_attributes/json_with_shebang.ts.out",
-  exit_code: 1,
-});
-
-itest!(shebang_with_json_imports_swc {
-  args: "run --quiet --no-check import_attributes/json_with_shebang.ts",
-  output: "import_attributes/json_with_shebang.ts.out",
-  exit_code: 1,
-});
-
 #[test]
 fn no_validate_asm() {
   let output = util::deno_cmd()
@@ -2521,7 +1172,6 @@ fn dont_cache_on_check_fail() {
 
 mod permissions {
   use test_util as util;
-  use test_util::itest;
   use util::TestContext;
 
   #[test]
@@ -2971,31 +1621,6 @@ mod permissions {
       });
   }
 
-  itest!(_063_permissions_revoke {
-    args: "run --allow-read=foo,bar run/063_permissions_revoke.ts",
-    output: "run/063_permissions_revoke.ts.out",
-  });
-
-  itest!(_063_permissions_revoke_sync {
-    args: "run --allow-read=foo,bar run/063_permissions_revoke_sync.ts",
-    output: "run/063_permissions_revoke.ts.out",
-  });
-
-  itest!(_064_permissions_revoke_global {
-    args: "run --allow-read=foo,bar run/064_permissions_revoke_global.ts",
-    output: "run/064_permissions_revoke_global.ts.out",
-  });
-
-  itest!(_064_permissions_revoke_global_sync {
-    args: "run --allow-read=foo,bar run/064_permissions_revoke_global_sync.ts",
-    output: "run/064_permissions_revoke_global.ts.out",
-  });
-
-  itest!(_065_permissions_revoke_net {
-    args: "run --allow-net run/065_permissions_revoke_net.ts",
-    output: "run/065_permissions_revoke_net.ts.out",
-  });
-
   #[test]
   fn _066_prompt() {
     TestContext::default()
@@ -3031,63 +1656,8 @@ mod permissions {
         console.expect("The end of test");
       });
   }
-
-  itest!(dynamic_import_static_analysis_no_permissions {
-    args: "run --quiet --reload --no-prompt dynamic_import/static_analysis_no_permissions.ts",
-    output: "dynamic_import/static_analysis_no_permissions.ts.out",
-  });
-
-  itest!(dynamic_import_permissions_remote_remote {
-    args: "run --quiet --reload --allow-import=localhost:4545 dynamic_import/permissions_remote_remote.ts",
-    output: "dynamic_import/permissions_remote_remote.ts.out",
-    http_server: true,
-    exit_code: 1,
-  });
-
-  itest!(dynamic_import_permissions_data_remote {
-    args: "run --quiet --reload --allow-import=localhost:4545 dynamic_import/permissions_data_remote.ts",
-    output: "dynamic_import/permissions_data_remote.ts.out",
-    http_server: true,
-    exit_code: 1,
-  });
-
-  itest!(dynamic_import_permissions_blob_remote {
-    args: "run --quiet --reload --allow-net=localhost:4545 dynamic_import/permissions_blob_remote.ts",
-    output: "dynamic_import/permissions_blob_remote.ts.out",
-    http_server: true,
-    exit_code: 1,
-  });
-
-  itest!(dynamic_import_permissions_data_local {
-    args: "run --quiet --reload --allow-net=localhost:4545 dynamic_import/permissions_data_local.ts",
-    output: "dynamic_import/permissions_data_local.ts.out",
-    http_server: true,
-    exit_code: 1,
-  });
-
-  itest!(dynamic_import_permissions_blob_local {
-    args: "run --quiet --reload --allow-net=localhost:4545 dynamic_import/permissions_blob_local.ts",
-    output: "dynamic_import/permissions_blob_local.ts.out",
-    http_server: true,
-    exit_code: 1,
-  });
 }
 
-itest!(tls_starttls {
-  args: "run --quiet --reload --allow-net --allow-read --cert tls/RootCA.pem --config ../config/deno.json run/tls_starttls.js",
-  output: "run/tls.out",
-});
-
-itest!(tls_connecttls {
-  args: "run --quiet --reload --allow-net --allow-read --cert tls/RootCA.pem --config ../config/deno.json run/tls_connecttls.js",
-  output: "run/tls.out",
-});
-
-itest!(byte_order_mark {
-  args: "run --no-check run/byte_order_mark.ts",
-  output: "run/byte_order_mark.out",
-});
-
 #[test]
 #[cfg(windows)]
 fn process_stdin_read_unblock() {
@@ -3135,24 +1705,6 @@ fn issue9750() {
     });
 }
 
-// Regression test for https://github.com/denoland/deno/issues/11451.
-itest!(dom_exception_formatting {
-  args: "run run/dom_exception_formatting.ts",
-  output: "run/dom_exception_formatting.ts.out",
-  exit_code: 1,
-});
-
-itest!(long_data_url_formatting {
-  args: "run run/long_data_url_formatting.ts",
-  output: "run/long_data_url_formatting.ts.out",
-  exit_code: 1,
-});
-
-itest!(eval_context_throw_dom_exception {
-  args: "run run/eval_context_throw_dom_exception.js",
-  output: "run/eval_context_throw_dom_exception.js.out",
-});
-
 #[test]
 #[cfg(unix)]
 fn navigator_language_unix() {
@@ -3276,85 +1828,6 @@ fn issue12807() {
   assert!(status.success());
 }
 
-itest!(issue_13562 {
-  args: "run run/issue13562.ts",
-  output: "run/issue13562.ts.out",
-});
-
-itest!(import_attributes_static_import {
-  args: "run --allow-read import_attributes/static_import.ts",
-  output: "import_attributes/static_import.out",
-});
-
-itest!(import_attributes_static_export {
-  args: "run --allow-read import_attributes/static_export.ts",
-  output: "import_attributes/static_export.out",
-});
-
-itest!(import_attributes_static_error {
-  args: "run --allow-read import_attributes/static_error.ts",
-  output: "import_attributes/static_error.out",
-  exit_code: 1,
-});
-
-itest!(import_attributes_dynamic_import {
-  args: "run --allow-read --check import_attributes/dynamic_import.ts",
-  output: "import_attributes/dynamic_import.out",
-});
-
-itest!(import_attributes_dynamic_error {
-  args: "run --allow-read import_attributes/dynamic_error.ts",
-  output: "import_attributes/dynamic_error.out",
-  exit_code: 1,
-});
-
-itest!(import_attributes_type_check {
-  args: "run --allow-read --check import_attributes/type_check.ts",
-  output: "import_attributes/type_check.out",
-  exit_code: 1,
-});
-
-itest!(colors_without_global_this {
-  args: "run run/colors_without_globalThis.js",
-  output_str: Some("true\n"),
-});
-
-itest!(config_auto_discovered_for_local_script {
-  args: "run --quiet run/with_config/frontend_work.ts",
-  output_str: Some("ok\n"),
-});
-
-itest!(config_auto_discovered_for_local_script_log {
-  args: "run -L debug run/with_config/frontend_work.ts",
-  output: "run/with_config/auto_discovery_log.out",
-});
-
-itest!(no_config_auto_discovery_for_local_script {
-  args: "run --quiet --no-config --check run/with_config/frontend_work.ts",
-  output: "run/with_config/no_auto_discovery.out",
-  exit_code: 1,
-});
-
-itest!(config_not_auto_discovered_for_remote_script {
-  args: "run --allow-import --quiet http://127.0.0.1:4545/run/with_config/server_side_work.ts",
-  output_str: Some("ok\n"),
-  http_server: true,
-});
-
-// In this case we shouldn't discover `package.json` file, because it's in a
-// directory that is above the directory containing `deno.json` file.
-itest!(
-  package_json_auto_discovered_for_local_script_arg_with_stop {
-    args: "run -L debug with_stop/some/nested/dir/main.ts",
-    output: "run/with_package_json/with_stop/main.out",
-    cwd: Some("run/with_package_json/"),
-    copy_temp_dir: Some("run/with_package_json/"),
-    envs: env_vars_for_npm_tests(),
-    http_server: true,
-    exit_code: 1,
-  }
-);
-
 #[test]
 fn package_json_no_node_modules_dir_created() {
   // it should not create a node_modules directory
@@ -3393,81 +1866,6 @@ fn node_modules_dir_no_npm_specifiers_no_dir_created() {
   assert!(!temp_dir.path().join("node_modules").exists());
 }
 
-itest!(wasm_streaming_panic_test {
-  args: "run run/wasm_streaming_panic_test.js",
-  output: "run/wasm_streaming_panic_test.js.out",
-  exit_code: 1,
-});
-
-// Regression test for https://github.com/denoland/deno/issues/13897.
-itest!(fetch_async_error_stack {
-  args: "run --quiet -A run/fetch_async_error_stack.ts",
-  output: "run/fetch_async_error_stack.ts.out",
-  exit_code: 1,
-});
-
-itest!(event_listener_error {
-  args: "run --quiet run/event_listener_error.ts",
-  output: "run/event_listener_error.ts.out",
-  exit_code: 1,
-});
-
-itest!(event_listener_error_handled {
-  args: "run --quiet run/event_listener_error_handled.ts",
-  output: "run/event_listener_error_handled.ts.out",
-});
-
-// https://github.com/denoland/deno/pull/14159#issuecomment-1092285446
-itest!(event_listener_error_immediate_exit {
-  args: "run --quiet run/event_listener_error_immediate_exit.ts",
-  output: "run/event_listener_error_immediate_exit.ts.out",
-  exit_code: 1,
-});
-
-// https://github.com/denoland/deno/pull/14159#issuecomment-1092285446
-itest!(event_listener_error_immediate_exit_worker {
-  args: "run --quiet -A run/event_listener_error_immediate_exit_worker.ts",
-  output: "run/event_listener_error_immediate_exit_worker.ts.out",
-  exit_code: 1,
-});
-
-itest!(set_timeout_error {
-  args: "run --quiet run/set_timeout_error.ts",
-  output: "run/set_timeout_error.ts.out",
-  exit_code: 1,
-});
-
-itest!(set_timeout_error_handled {
-  args: "run --quiet run/set_timeout_error_handled.ts",
-  output: "run/set_timeout_error_handled.ts.out",
-});
-
-itest!(aggregate_error {
-  args: "run --quiet run/aggregate_error.ts",
-  output: "run/aggregate_error.out",
-  exit_code: 1,
-});
-
-itest!(complex_error {
-  args: "run --quiet run/complex_error.ts",
-  output: "run/complex_error.ts.out",
-  exit_code: 1,
-});
-
-// Regression test for https://github.com/denoland/deno/issues/16340.
-itest!(error_with_errors_prop {
-  args: "run --quiet run/error_with_errors_prop.js",
-  output: "run/error_with_errors_prop.js.out",
-  exit_code: 1,
-});
-
-// Regression test for https://github.com/denoland/deno/issues/12143.
-itest!(js_root_with_ts_check {
-  args: "run --quiet --check run/js_root_with_ts_check.js",
-  output: "run/js_root_with_ts_check.js.out",
-  exit_code: 1,
-});
-
 #[test]
 fn check_local_then_remote() {
   let _http_guard = util::http_server();
@@ -3500,17 +1898,21 @@ fn check_local_then_remote() {
   assert_contains!(stderr, "Type 'string' is not assignable to type 'number'.");
 }
 
-// Regression test for https://github.com/denoland/deno/issues/15163
-itest!(check_js_points_to_ts {
-  args: "run --quiet --check --config run/checkjs.tsconfig.json run/check_js_points_to_ts/test.js",
-  output: "run/check_js_points_to_ts/test.js.out",
-  exit_code: 1,
-});
-
-itest!(no_prompt_flag {
-  args: "run --quiet --no-prompt run/no_prompt.ts",
-  output_str: Some(""),
-});
+#[test]
+fn permission_request_with_no_prompt() {
+  TestContext::default()
+    .new_command()
+    .env("NO_COLOR", "1")
+    .args_vec([
+      "run",
+      "--quiet",
+      "--no-prompt",
+      "run/permission_request_no_prompt.ts",
+    ])
+    .with_pty(|mut console| {
+      console.expect("PermissionStatus { state: \"denied\", onchange: null }");
+    });
+}
 
 #[test]
 fn deno_no_prompt_environment_variable() {
@@ -3526,57 +1928,6 @@ fn deno_no_prompt_environment_variable() {
   assert!(output.status.success());
 }
 
-itest!(report_error {
-  args: "run --quiet run/report_error.ts",
-  output: "run/report_error.ts.out",
-  exit_code: 1,
-});
-
-itest!(report_error_handled {
-  args: "run --quiet run/report_error_handled.ts",
-  output: "run/report_error_handled.ts.out",
-});
-
-// Regression test for https://github.com/denoland/deno/issues/15513.
-itest!(report_error_end_of_program {
-  args: "run --quiet run/report_error_end_of_program.ts",
-  output: "run/report_error_end_of_program.ts.out",
-  exit_code: 1,
-});
-
-itest!(queue_microtask_error {
-  args: "run --quiet run/queue_microtask_error.ts",
-  output: "run/queue_microtask_error.ts.out",
-  exit_code: 1,
-});
-
-itest!(queue_microtask_error_handled {
-  args: "run --quiet run/queue_microtask_error_handled.ts",
-  output: "run/queue_microtask_error_handled.ts.out",
-});
-
-itest!(spawn_stdout_inherit {
-  args: "run --quiet -A run/spawn_stdout_inherit.ts",
-  output: "run/spawn_stdout_inherit.ts.out",
-});
-
-itest!(error_name_non_string {
-  args: "run --quiet run/error_name_non_string.js",
-  output: "run/error_name_non_string.js.out",
-  exit_code: 1,
-});
-
-itest!(custom_inspect_url {
-  args: "run run/custom_inspect_url.js",
-  output: "run/custom_inspect_url.js.out",
-});
-
-itest!(config_json_import {
-  args: "run --quiet -c jsx/deno-jsx.json run/config_json_import.ts",
-  output: "run/config_json_import.ts.out",
-  http_server: true,
-});
-
 #[test]
 fn running_declaration_files() {
   let context = TestContextBuilder::new().use_temp_cwd().build();
@@ -3587,18 +1938,14 @@ fn running_declaration_files() {
     temp_dir.write(file, "");
     context
       .new_command()
-      .args_vec(["run", file])
+      // todo(dsherret): investigate why --allow-read is required here
+      .args_vec(["run", "--allow-read", file])
       .run()
       .skip_output_check()
       .assert_exit_code(0);
   }
 }
 
-itest!(test_and_bench_are_noops_in_run {
-  args: "run run/test_and_bench_in_run.js",
-  output_str: Some(""),
-});
-
 #[cfg(not(target_os = "windows"))]
 itest!(spawn_kill_permissions {
   args: "run --quiet --allow-run=cat spawn_kill_permissions.ts",
@@ -3609,51 +1956,6 @@ itest!(spawn_kill_permissions {
   output_str: Some(""),
 });
 
-itest!(followup_dyn_import_resolved {
-  args: "run --allow-read run/followup_dyn_import_resolves/main.ts",
-  output: "run/followup_dyn_import_resolves/main.ts.out",
-});
-
-itest!(unhandled_rejection {
-  args: "run --check run/unhandled_rejection.ts",
-  output: "run/unhandled_rejection.ts.out",
-});
-
-itest!(unhandled_rejection_sync_error {
-  args: "run --check run/unhandled_rejection_sync_error.ts",
-  output: "run/unhandled_rejection_sync_error.ts.out",
-});
-
-// Regression test for https://github.com/denoland/deno/issues/15661
-itest!(unhandled_rejection_dynamic_import {
-  args: "run --allow-read run/unhandled_rejection_dynamic_import/main.ts",
-  output: "run/unhandled_rejection_dynamic_import/main.ts.out",
-  exit_code: 1,
-});
-
-// Regression test for https://github.com/denoland/deno/issues/16909
-itest!(unhandled_rejection_dynamic_import2 {
-  args: "run --allow-read run/unhandled_rejection_dynamic_import2/main.ts",
-  output: "run/unhandled_rejection_dynamic_import2/main.ts.out",
-});
-
-itest!(rejection_handled {
-  args: "run --check run/rejection_handled.ts",
-  output: "run/rejection_handled.out",
-});
-
-itest!(nested_error {
-  args: "run run/nested_error/main.ts",
-  output: "run/nested_error/main.ts.out",
-  exit_code: 1,
-});
-
-itest!(node_env_var_allowlist {
-  args: "run --no-prompt run/node_env_var_allowlist.ts",
-  output: "run/node_env_var_allowlist.ts.out",
-  exit_code: 1,
-});
-
 #[test]
 fn cache_test() {
   let _g = util::http_server();
@@ -3872,6 +2174,11 @@ fn basic_auth_tokens() {
 
 #[tokio::test(flavor = "multi_thread", worker_threads = 2)]
 async fn test_resolve_dns() {
+  use hickory_server::authority::Catalog;
+  use hickory_server::authority::ZoneType;
+  use hickory_server::proto::rr::Name;
+  use hickory_server::store::in_memory::InMemoryAuthority;
+  use hickory_server::ServerFuture;
   use std::net::SocketAddr;
   use std::str::FromStr;
   use std::sync::Arc;
@@ -3879,11 +2186,6 @@ async fn test_resolve_dns() {
   use tokio::net::TcpListener;
   use tokio::net::UdpSocket;
   use tokio::sync::oneshot;
-  use trust_dns_server::authority::Catalog;
-  use trust_dns_server::authority::ZoneType;
-  use trust_dns_server::proto::rr::Name;
-  use trust_dns_server::store::in_memory::InMemoryAuthority;
-  use trust_dns_server::ServerFuture;
 
   const DNS_PORT: u16 = 4553;
 
@@ -3893,9 +2195,12 @@ async fn test_resolve_dns() {
       util::testdata_path().join("run/resolve_dns.zone.in"),
     )
     .unwrap();
-    let lexer = Lexer::new(&zone_file);
-    let records =
-      Parser::new().parse(lexer, Some(Name::from_str("example.com").unwrap()));
+    let records = Parser::new(
+      &zone_file,
+      None,
+      Some(Name::from_str("example.com").unwrap()),
+    )
+    .parse();
     if records.is_err() {
       panic!("failed to parse: {:?}", records.err())
     }
@@ -4193,48 +2498,6 @@ fn broken_stdout_repl() {
   assert_not_contains!(stderr, "panic");
 }
 
-itest!(error_cause {
-  args: "run run/error_cause.ts",
-  output: "run/error_cause.ts.out",
-  exit_code: 1,
-});
-
-itest!(error_cause_recursive_aggregate {
-  args: "run error_cause_recursive_aggregate.ts",
-  output: "error_cause_recursive_aggregate.ts.out",
-  exit_code: 1,
-});
-
-itest!(error_cause_recursive_tail {
-  args: "run error_cause_recursive_tail.ts",
-  output: "error_cause_recursive_tail.ts.out",
-  exit_code: 1,
-});
-
-itest!(error_cause_recursive {
-  args: "run run/error_cause_recursive.ts",
-  output: "run/error_cause_recursive.ts.out",
-  exit_code: 1,
-});
-
-itest!(js_without_extension {
-  args: "run --ext js --check file_extensions/js_without_extension",
-  output: "file_extensions/js_without_extension.out",
-  exit_code: 0,
-});
-
-itest!(ts_without_extension {
-  args: "run --ext ts --check file_extensions/ts_without_extension",
-  output: "file_extensions/ts_without_extension.out",
-  exit_code: 0,
-});
-
-itest!(ext_flag_takes_precedence_over_extension {
-  args: "run --ext ts --check file_extensions/ts_with_js_extension.js",
-  output: "file_extensions/ts_with_js_extension.out",
-  exit_code: 0,
-});
-
 #[tokio::test(flavor = "multi_thread")]
 async fn websocketstream_ping() {
   let _g = util::http_server();
@@ -4416,24 +2679,6 @@ async fn websocket_server_idletimeout() {
   assert_eq!(child.wait().unwrap().code(), Some(123));
 }
 
-itest!(no_lock_flag {
-  args: "run --allow-import --no-lock run/no_lock_flag/main.ts",
-  output: "run/no_lock_flag/main.out",
-  http_server: true,
-  exit_code: 0,
-});
-
-itest!(permission_args {
-  args: "run run/001_hello.js --allow-net",
-  output: "run/permission_args.out",
-  envs: vec![("NO_COLOR".to_string(), "1".to_string())],
-});
-
-itest!(permission_args_quiet {
-  args: "run --quiet run/001_hello.js --allow-net",
-  output: "run/001_hello.js.out",
-});
-
 // Regression test for https://github.com/denoland/deno/issues/16772
 #[test]
 fn file_fetcher_preserves_permissions() {
@@ -4541,12 +2786,6 @@ fn permission_prompt_escapes_ansi_codes_and_control_chars() {
   }
 }
 
-itest!(dynamic_import_syntax_error {
-  args: "run -A run/dynamic_import_syntax_error.js",
-  output: "run/dynamic_import_syntax_error.js.out",
-  exit_code: 1,
-});
-
 itest!(extension_import {
   args: "run run/extension_import.ts",
   output: "run/extension_import.ts.out",
@@ -4660,56 +2899,6 @@ console.log(returnsHi());"#,
     .assert_exit_code(1);
 }
 
-itest!(explicit_resource_management {
-  args: "run --quiet --check run/explicit_resource_management/main.ts",
-  output: "run/explicit_resource_management/main.out",
-});
-
-itest!(unsafe_proto {
-  args: "run -A run/unsafe_proto/main.js",
-  output: "run/unsafe_proto/main.out",
-  http_server: false,
-  exit_code: 0,
-});
-
-itest!(unsafe_proto_flag {
-  args: "run -A --unstable-unsafe-proto run/unsafe_proto/main.js",
-  output: "run/unsafe_proto/main_with_unsafe_proto_flag.out",
-  http_server: false,
-  exit_code: 0,
-});
-
-// TODO(bartlomieju): temporary disabled
-// itest!(warn_on_deprecated_api {
-//   args: "run -A run/warn_on_deprecated_api/main.js",
-//   output: "run/warn_on_deprecated_api/main.out",
-//   http_server: true,
-//   exit_code: 0,
-// });
-
-// itest!(warn_on_deprecated_api_verbose {
-//   args: "run -A run/warn_on_deprecated_api/main.js",
-//   output: "run/warn_on_deprecated_api/main.verbose.out",
-//   envs: vec![("DENO_VERBOSE_WARNINGS".to_string(), "1".to_string())],
-//   http_server: true,
-//   exit_code: 0,
-// });
-
-// itest!(warn_on_deprecated_api_with_flag {
-//   args: "run -A --quiet run/warn_on_deprecated_api/main.js",
-//   output: "run/warn_on_deprecated_api/main_disabled_flag.out",
-//   http_server: true,
-//   exit_code: 0,
-// });
-
-// itest!(warn_on_deprecated_api_with_env_var {
-//   args: "run -A run/warn_on_deprecated_api/main.js",
-//   envs: vec![("DENO_NO_DEPRECATION_WARNINGS".to_string(), "1".to_string())],
-//   output: "run/warn_on_deprecated_api/main_disabled_env.out",
-//   http_server: true,
-//   exit_code: 0,
-// });
-
 #[test]
 fn deno_json_imports_expand() {
   let test_context = TestContextBuilder::for_npm().use_temp_cwd().build();
@@ -5132,6 +3321,8 @@ fn emit_failed_readonly_file_system() {
   output.assert_matches_text("[WILDCARD]Error saving emit data ([WILDLINE]main.ts)[WILDCARD]Skipped emit cache save of [WILDLINE]other.ts[WILDCARD]hi[WILDCARD]");
 }
 
+// todo(dsherret): waiting on fix in https://github.com/servo/rust-url/issues/505
+#[ignore]
 #[cfg(windows)]
 #[test]
 fn handle_invalid_path_error() {
diff --git a/tests/integration/task_tests.rs b/tests/integration/task_tests.rs
index d198a3be6f..56bab2970d 100644
--- a/tests/integration/task_tests.rs
+++ b/tests/integration/task_tests.rs
@@ -18,19 +18,6 @@
 //   http_server: true,
 // });
 
-// TODO(2.0): decide what to do with this test
-// should not auto-install the packages in the package.json
-// when using nodeModulesDir: false
-// itest!(task_package_json_node_modules_dir_false {
-//   args: "task echo",
-//   cwd: Some("task/package_json_node_modules_dir_false/"),
-//   output: "task/package_json_node_modules_dir_false/bin.out",
-//   copy_temp_dir: Some("task/package_json_node_modules_dir_false/"),
-//   envs: env_vars_for_npm_tests(),
-//   exit_code: 0,
-//   http_server: true,
-// });
-
 // TODO(2.0): not entirely clear what's wrong with this test but it hangs for more than 60s
 // itest!(task_npx_on_own {
 //   args: "task on-own",
diff --git a/tests/integration/watcher_tests.rs b/tests/integration/watcher_tests.rs
index 122353bba9..e8f264632d 100644
--- a/tests/integration/watcher_tests.rs
+++ b/tests/integration/watcher_tests.rs
@@ -566,6 +566,82 @@ async fn run_watch_no_dynamic() {
   check_alive_then_kill(child);
 }
 
+#[flaky_test(tokio)]
+async fn serve_watch_all() {
+  let t = TempDir::new();
+  let main_file_to_watch = t.path().join("main_file_to_watch.js");
+  main_file_to_watch.write(
+    "export default {
+      fetch(_request) {
+        return new Response(\"aaaaaaqqq!\");
+      },
+    };",
+  );
+
+  let another_file = t.path().join("another_file.js");
+  another_file.write("");
+
+  let mut child = util::deno_cmd()
+    .current_dir(t.path())
+    .arg("serve")
+    .arg(format!("--watch={another_file}"))
+    .arg("-L")
+    .arg("debug")
+    .arg(&main_file_to_watch)
+    .env("NO_COLOR", "1")
+    .piped_output()
+    .spawn()
+    .unwrap();
+  let (mut stdout_lines, mut stderr_lines) = child_lines(&mut child);
+
+  wait_for_watcher("main_file_to_watch.js", &mut stderr_lines).await;
+
+  // Change content of the file
+  main_file_to_watch.write(
+    "export default {
+      fetch(_request) {
+        return new Response(\"aaaaaaqqq123!\");
+      },
+    };",
+  );
+  wait_contains("Restarting", &mut stderr_lines).await;
+  wait_for_watcher("main_file_to_watch.js", &mut stderr_lines).await;
+
+  another_file.write("export const foo = 0;");
+  // Confirm that the added file is watched as well
+  wait_contains("Restarting", &mut stderr_lines).await;
+  wait_for_watcher("main_file_to_watch.js", &mut stderr_lines).await;
+
+  main_file_to_watch
+    .write("import { foo } from './another_file.js'; console.log(foo);");
+  wait_contains("Restarting", &mut stderr_lines).await;
+  wait_for_watcher("main_file_to_watch.js", &mut stderr_lines).await;
+  wait_contains("0", &mut stdout_lines).await;
+
+  another_file.write("export const foo = 42;");
+  wait_contains("Restarting", &mut stderr_lines).await;
+  wait_for_watcher("main_file_to_watch.js", &mut stderr_lines).await;
+  wait_contains("42", &mut stdout_lines).await;
+
+  // Confirm that watch continues even with wrong syntax error
+  another_file.write("syntax error ^^");
+
+  wait_contains("Restarting", &mut stderr_lines).await;
+  wait_contains("error:", &mut stderr_lines).await;
+  wait_for_watcher("main_file_to_watch.js", &mut stderr_lines).await;
+
+  main_file_to_watch.write(
+    "export default {
+      fetch(_request) {
+        return new Response(\"aaaaaaqqq!\");
+      },
+    };",
+  );
+  wait_contains("Restarting", &mut stderr_lines).await;
+  wait_for_watcher("main_file_to_watch.js", &mut stderr_lines).await;
+  check_alive_then_kill(child);
+}
+
 #[flaky_test(tokio)]
 async fn run_watch_npm_specifier() {
   let _g = util::http_server();
diff --git a/tests/napi/Cargo.toml b/tests/napi/Cargo.toml
index 611d6d5507..e3de253683 100644
--- a/tests/napi/Cargo.toml
+++ b/tests/napi/Cargo.toml
@@ -13,6 +13,7 @@ repository.workspace = true
 crate-type = ["cdylib"]
 
 [dependencies]
+libuv-sys-lite = "=1.48.2"
 napi-sys = { version = "=2.2.2", default-features = false, features = ["napi7"] }
 
 [dev-dependencies]
diff --git a/tests/napi/callback_test.js b/tests/napi/callback_test.js
index 98622d48d1..c132fefa18 100644
--- a/tests/napi/callback_test.js
+++ b/tests/napi/callback_test.js
@@ -1,6 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-import { assertEquals, loadTestLibrary } from "./common.js";
+import { assertEquals, assertThrows, loadTestLibrary } from "./common.js";
 
 const callback = loadTestLibrary();
 
@@ -36,3 +36,12 @@ Deno.test("napi callback run with args & recv", function () {
   );
   assertEquals(result, 69);
 });
+
+Deno.test("napi callback handles errors correctly", function () {
+  const e = new Error("hi!");
+  assertThrows(() => {
+    callback.test_callback_throws(() => {
+      throw e;
+    });
+  }, e);
+});
diff --git a/tests/napi/object_test.js b/tests/napi/object_test.js
index 4bc5c3c9c4..6226b0138c 100644
--- a/tests/napi/object_test.js
+++ b/tests/napi/object_test.js
@@ -1,6 +1,11 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-import { assert, assertEquals, loadTestLibrary } from "./common.js";
+import {
+  assert,
+  assertEquals,
+  assertThrows,
+  loadTestLibrary,
+} from "./common.js";
 
 const object = loadTestLibrary();
 
@@ -12,4 +17,22 @@ Deno.test("napi object", function () {
 
   const r1 = object.test_object_get(r);
   assert(r === r1);
+
+  const r2 = object.test_object_attr_property(r);
+  assert(r === r2);
+  assertThrows(
+    () => {
+      r2.self = "2";
+    },
+    Error,
+    "Cannot assign to read only property 'self' of object '#<Object>'",
+  );
+
+  assertThrows(
+    () => {
+      r2.method = () => {};
+    },
+    Error,
+    "Cannot assign to read only property 'method' of object '#<Object>'",
+  );
 });
diff --git a/tests/napi/src/async.rs b/tests/napi/src/async.rs
index 3d3827b51c..367d2e9ef0 100644
--- a/tests/napi/src/async.rs
+++ b/tests/napi/src/async.rs
@@ -95,7 +95,7 @@ extern "C" fn test_async_work(
   ));
   let mut baton = unsafe { Box::from_raw(baton_ptr as *mut Baton) };
   baton.task = async_work;
-  Box::into_raw(baton);
+  let _ = Box::into_raw(baton);
   assert_napi_ok!(napi_queue_async_work(env, async_work));
 
   ptr::null_mut()
diff --git a/tests/napi/src/callback.rs b/tests/napi/src/callback.rs
index 8909f51768..2512f6a38f 100644
--- a/tests/napi/src/callback.rs
+++ b/tests/napi/src/callback.rs
@@ -8,6 +8,7 @@ use napi_sys::ValueType::napi_object;
 use napi_sys::ValueType::napi_undefined;
 use napi_sys::*;
 use std::ptr;
+use Status::napi_pending_exception;
 
 /// `test_callback_run((a, b) => a + b, [1, 2])` => 3
 extern "C" fn test_callback_run(
@@ -98,6 +99,34 @@ extern "C" fn test_callback_run_with_recv(
   result
 }
 
+extern "C" fn test_callback_throws(
+  env: napi_env,
+  info: napi_callback_info,
+) -> napi_value {
+  let (args, ..) = napi_get_callback_info!(env, info, 1);
+
+  let mut global: napi_value = ptr::null_mut();
+  assert_napi_ok!(napi_get_global(env, &mut global));
+
+  let mut argv = vec![];
+  let mut result: napi_value = ptr::null_mut();
+  assert_eq!(
+    unsafe {
+      napi_call_function(
+        env,
+        global,  // recv
+        args[0], // cb
+        argv.len(),
+        argv.as_mut_ptr(),
+        &mut result,
+      )
+    },
+    napi_pending_exception
+  );
+
+  result
+}
+
 pub fn init(env: napi_env, exports: napi_value) {
   let properties = &[
     napi_new_property!(env, "test_callback_run", test_callback_run),
@@ -106,6 +135,7 @@ pub fn init(env: napi_env, exports: napi_value) {
       "test_callback_run_with_recv",
       test_callback_run_with_recv
     ),
+    napi_new_property!(env, "test_callback_throws", test_callback_throws),
   ];
 
   assert_napi_ok!(napi_define_properties(
diff --git a/tests/napi/src/lib.rs b/tests/napi/src/lib.rs
index f6fe6e189a..8c6190ad3e 100644
--- a/tests/napi/src/lib.rs
+++ b/tests/napi/src/lib.rs
@@ -31,6 +31,7 @@ pub mod strings;
 pub mod symbol;
 pub mod tsfn;
 pub mod typedarray;
+pub mod uv;
 
 #[macro_export]
 macro_rules! cstr {
@@ -138,6 +139,7 @@ unsafe extern "C" fn napi_register_module_v1(
   #[cfg(windows)]
   {
     napi_sys::setup();
+    libuv_sys_lite::setup();
   }
 
   // We create a fresh exports object and leave the passed
@@ -169,6 +171,7 @@ unsafe extern "C" fn napi_register_module_v1(
   symbol::init(env, exports);
   make_callback::init(env, exports);
   object::init(env, exports);
+  uv::init(env, exports);
 
   init_cleanup_hook(env, exports);
 
diff --git a/tests/napi/src/object.rs b/tests/napi/src/object.rs
index aa34133dcf..9876f4dae0 100644
--- a/tests/napi/src/object.rs
+++ b/tests/napi/src/object.rs
@@ -40,10 +40,39 @@ extern "C" fn test_object_get(
   obj
 }
 
+extern "C" fn test_object_attr_property(
+  env: napi_env,
+  info: napi_callback_info,
+) -> napi_value {
+  let (args, argc, _) = napi_get_callback_info!(env, info, 1);
+  assert_eq!(argc, 1);
+
+  let obj = args[0];
+  let mut property = napi_new_property!(env, "self", test_object_new);
+  property.attributes = PropertyAttributes::enumerable;
+  property.method = None;
+  property.value = obj;
+  let mut method_property = napi_new_property!(env, "method", test_object_new);
+  method_property.attributes = PropertyAttributes::enumerable;
+  let properties = &[property, method_property];
+  assert_napi_ok!(napi_define_properties(
+    env,
+    obj,
+    properties.len(),
+    properties.as_ptr()
+  ));
+  obj
+}
+
 pub fn init(env: napi_env, exports: napi_value) {
   let properties = &[
     napi_new_property!(env, "test_object_new", test_object_new),
     napi_new_property!(env, "test_object_get", test_object_get),
+    napi_new_property!(
+      env,
+      "test_object_attr_property",
+      test_object_attr_property
+    ),
   ];
 
   assert_napi_ok!(napi_define_properties(
diff --git a/tests/napi/src/tsfn.rs b/tests/napi/src/tsfn.rs
index dabc96f835..a3a231cec1 100644
--- a/tests/napi/src/tsfn.rs
+++ b/tests/napi/src/tsfn.rs
@@ -46,6 +46,7 @@ fn create_custom_gc(env: sys::napi_env) {
     "Create async resource string in napi_register_module_v1 napi_register_module_v1"
   );
   let mut custom_gc_tsfn = ptr::null_mut();
+  let context = Box::into_raw(Box::new(0)) as *mut c_void;
   check_status_or_panic!(
     unsafe {
       sys::napi_create_threadsafe_function(
@@ -57,7 +58,7 @@ fn create_custom_gc(env: sys::napi_env) {
         1,
         ptr::null_mut(),
         Some(custom_gc_finalize),
-        ptr::null_mut(),
+        context,
         Some(custom_gc),
         &mut custom_gc_tsfn,
       )
@@ -80,8 +81,9 @@ unsafe extern "C" fn empty(
 unsafe extern "C" fn custom_gc_finalize(
   _env: sys::napi_env,
   _finalize_data: *mut c_void,
-  _finalize_hint: *mut c_void,
+  finalize_hint: *mut c_void,
 ) {
+  let _ = Box::from_raw(finalize_hint as *mut i32);
 }
 
 extern "C" fn custom_gc(
diff --git a/tests/napi/src/uv.rs b/tests/napi/src/uv.rs
new file mode 100644
index 0000000000..555470c008
--- /dev/null
+++ b/tests/napi/src/uv.rs
@@ -0,0 +1,206 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+use crate::assert_napi_ok;
+use crate::napi_get_callback_info;
+use crate::napi_new_property;
+use libuv_sys_lite::uv_async_init;
+use libuv_sys_lite::uv_async_t;
+use libuv_sys_lite::uv_close;
+use libuv_sys_lite::uv_handle_t;
+use libuv_sys_lite::uv_mutex_destroy;
+use libuv_sys_lite::uv_mutex_lock;
+use libuv_sys_lite::uv_mutex_t;
+use libuv_sys_lite::uv_mutex_unlock;
+use napi_sys::*;
+use std::mem::MaybeUninit;
+use std::ptr;
+use std::ptr::addr_of_mut;
+use std::ptr::null_mut;
+use std::time::Duration;
+
+struct KeepAlive {
+  tsfn: napi_threadsafe_function,
+}
+
+impl KeepAlive {
+  fn new(env: napi_env) -> Self {
+    let mut name = null_mut();
+    assert_napi_ok!(napi_create_string_utf8(
+      env,
+      c"test_uv_async".as_ptr(),
+      13,
+      &mut name
+    ));
+
+    unsafe extern "C" fn dummy(
+      _env: napi_env,
+      _cb: napi_callback_info,
+    ) -> napi_value {
+      ptr::null_mut()
+    }
+
+    let mut func = null_mut();
+    assert_napi_ok!(napi_create_function(
+      env,
+      c"dummy".as_ptr(),
+      usize::MAX,
+      Some(dummy),
+      null_mut(),
+      &mut func,
+    ));
+
+    let mut tsfn = null_mut();
+    assert_napi_ok!(napi_create_threadsafe_function(
+      env,
+      func,
+      null_mut(),
+      name,
+      0,
+      1,
+      null_mut(),
+      None,
+      null_mut(),
+      None,
+      &mut tsfn,
+    ));
+    assert_napi_ok!(napi_ref_threadsafe_function(env, tsfn));
+    Self { tsfn }
+  }
+}
+
+impl Drop for KeepAlive {
+  fn drop(&mut self) {
+    assert_napi_ok!(napi_release_threadsafe_function(
+      self.tsfn,
+      ThreadsafeFunctionReleaseMode::release,
+    ));
+  }
+}
+
+struct Async {
+  mutex: *mut uv_mutex_t,
+  env: napi_env,
+  value: u32,
+  callback: napi_ref,
+  _keep_alive: KeepAlive,
+}
+
+#[derive(Clone, Copy)]
+struct UvAsyncPtr(*mut uv_async_t);
+
+unsafe impl Send for UvAsyncPtr {}
+
+fn new_raw<T>(t: T) -> *mut T {
+  Box::into_raw(Box::new(t))
+}
+
+unsafe extern "C" fn close_cb(handle: *mut uv_handle_t) {
+  let handle = handle.cast::<uv_async_t>();
+  let async_ = (*handle).data as *mut Async;
+  let env = (*async_).env;
+  assert_napi_ok!(napi_delete_reference(env, (*async_).callback));
+
+  uv_mutex_destroy((*async_).mutex);
+  let _ = Box::from_raw((*async_).mutex);
+  let _ = Box::from_raw(async_);
+  let _ = Box::from_raw(handle);
+}
+
+unsafe extern "C" fn callback(handle: *mut uv_async_t) {
+  eprintln!("callback");
+  let async_ = (*handle).data as *mut Async;
+  uv_mutex_lock((*async_).mutex);
+  let env = (*async_).env;
+  let mut js_cb = null_mut();
+  assert_napi_ok!(napi_get_reference_value(
+    env,
+    (*async_).callback,
+    &mut js_cb
+  ));
+  let mut global: napi_value = ptr::null_mut();
+  assert_napi_ok!(napi_get_global(env, &mut global));
+
+  let mut result: napi_value = ptr::null_mut();
+  let value = (*async_).value;
+  eprintln!("value is {value}");
+  let mut value_js = ptr::null_mut();
+  assert_napi_ok!(napi_create_uint32(env, value, &mut value_js));
+  let args = &[value_js];
+  assert_napi_ok!(napi_call_function(
+    env,
+    global,
+    js_cb,
+    1,
+    args.as_ptr(),
+    &mut result,
+  ));
+  uv_mutex_unlock((*async_).mutex);
+  if value == 5 {
+    uv_close(handle.cast(), Some(close_cb));
+  }
+}
+
+unsafe fn uv_async_send(ptr: UvAsyncPtr) {
+  assert_napi_ok!(libuv_sys_lite::uv_async_send(ptr.0));
+}
+
+fn make_uv_mutex() -> *mut uv_mutex_t {
+  let mutex = new_raw(MaybeUninit::<uv_mutex_t>::uninit());
+  assert_napi_ok!(libuv_sys_lite::uv_mutex_init(mutex.cast()));
+  mutex.cast()
+}
+
+#[allow(unused_unsafe)]
+extern "C" fn test_uv_async(
+  env: napi_env,
+  info: napi_callback_info,
+) -> napi_value {
+  let (args, argc, _) = napi_get_callback_info!(env, info, 1);
+  assert_eq!(argc, 1);
+
+  let mut loop_ = null_mut();
+  assert_napi_ok!(napi_get_uv_event_loop(env, &mut loop_));
+  let uv_async = new_raw(MaybeUninit::<uv_async_t>::uninit());
+  let uv_async = uv_async.cast::<uv_async_t>();
+  let mut js_cb = null_mut();
+  assert_napi_ok!(napi_create_reference(env, args[0], 1, &mut js_cb));
+  // let mut tsfn = null_mut();
+
+  let data = new_raw(Async {
+    env,
+    callback: js_cb,
+    mutex: make_uv_mutex(),
+    value: 0,
+    _keep_alive: KeepAlive::new(env),
+  });
+  unsafe {
+    addr_of_mut!((*uv_async).data).write(data.cast());
+    assert_napi_ok!(uv_async_init(loop_.cast(), uv_async, Some(callback)));
+    let uv_async = UvAsyncPtr(uv_async);
+    std::thread::spawn({
+      move || {
+        let data = (*uv_async.0).data as *mut Async;
+        for _ in 0..5 {
+          uv_mutex_lock((*data).mutex);
+          (*data).value += 1;
+          uv_mutex_unlock((*data).mutex);
+          std::thread::sleep(Duration::from_millis(10));
+          uv_async_send(uv_async);
+        }
+      }
+    });
+  }
+
+  ptr::null_mut()
+}
+
+pub fn init(env: napi_env, exports: napi_value) {
+  let properties = &[napi_new_property!(env, "test_uv_async", test_uv_async)];
+
+  assert_napi_ok!(napi_define_properties(
+    env,
+    exports,
+    properties.len(),
+    properties.as_ptr()
+  ));
+}
diff --git a/tests/napi/uv_test.js b/tests/napi/uv_test.js
new file mode 100644
index 0000000000..af20b26493
--- /dev/null
+++ b/tests/napi/uv_test.js
@@ -0,0 +1,22 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+import { assertEquals, loadTestLibrary } from "./common.js";
+
+const uv = loadTestLibrary();
+
+Deno.test({
+  name: "napi uv async",
+  ignore: true,
+  fn: async () => {
+    let called = false;
+    await new Promise((resolve) => {
+      uv.test_uv_async((value) => {
+        called = true;
+        if (value === 5) {
+          resolve();
+        }
+      });
+    });
+    assertEquals(called, true);
+  },
+});
diff --git a/tests/node_compat/config.jsonc b/tests/node_compat/config.jsonc
index 2f94fa2f2e..664adaedfa 100644
--- a/tests/node_compat/config.jsonc
+++ b/tests/node_compat/config.jsonc
@@ -43,9 +43,6 @@
       // TODO(littledivy): windows ipc streams not yet implemented
       "test-child-process-fork-ref.js",
       "test-child-process-fork-ref2.js",
-      // TODO(bartlomieju): this test is very flaky on CI
-      // https://github.com/denoland/deno/issues/25855
-      // "test-child-process-ipc-next-tick.js",
       "test-child-process-ipc.js",
       "test-child-process-spawnsync-env.js",
       "test-child-process-stdio-inherit.js",
@@ -80,6 +77,7 @@
       "test-fs-rmdir-recursive.js",
       "test-fs-write-file.js",
       "test-http-url.parse-https.request.js",
+      "test-net-autoselectfamily.js",
       "test-net-better-error-messages-path.js",
       "test-net-connect-buffer.js",
       "test-net-connect-buffer2.js",
@@ -90,8 +88,6 @@
       "test-net-server-try-ports.js",
       "test-net-socket-timeout.js",
       "test-net-write-arguments.js",
-      // TODO(nathanwhit): Disable os.userInfo is slightly incorrect
-      // "test-os.js",
       "test-path-resolve.js",
       "test-querystring.js",
       "test-readline-interface.js",
@@ -240,6 +236,7 @@
       "test-child-process-execfilesync-maxbuf.js",
       "test-child-process-execsync-maxbuf.js",
       "test-child-process-flush-stdio.js",
+      "test-child-process-ipc-next-tick.js",
       "test-child-process-kill.js",
       "test-child-process-set-blocking.js",
       "test-child-process-spawn-args.js",
@@ -406,7 +403,9 @@
       "test-http-outgoing-settimeout.js",
       "test-http-url.parse-https.request.js",
       "test-http-url.parse-only-support-http-https-protocol.js",
+      "test-icu-transcode.js",
       "test-net-access-byteswritten.js",
+      "test-net-autoselectfamily.js",
       "test-net-better-error-messages-listen-path.js",
       "test-net-better-error-messages-path.js",
       "test-net-better-error-messages-port-hostname.js",
@@ -438,6 +437,7 @@
       "test-net-server-unref.js",
       "test-net-socket-destroy-twice.js",
       "test-net-socket-no-halfopen-enforcer.js",
+      "test-net-socket-setnodelay.js",
       "test-net-timeout-no-handle.js",
       "test-net-write-arguments.js",
       "test-next-tick-doesnt-hang.js",
@@ -448,6 +448,7 @@
       "test-next-tick-when-exiting.js",
       "test-next-tick.js",
       "test-nodeeventtarget.js",
+      "test-os.js",
       "test-outgoing-message-destroy.js",
       "test-outgoing-message-pipe.js",
       "test-parse-args.mjs",
diff --git a/tests/node_compat/package.json b/tests/node_compat/package.json
new file mode 100644
index 0000000000..5bbefffbab
--- /dev/null
+++ b/tests/node_compat/package.json
@@ -0,0 +1,3 @@
+{
+  "type": "commonjs"
+}
diff --git a/tests/node_compat/runner/TODO.md b/tests/node_compat/runner/TODO.md
index 24e8271828..27c2ef3e78 100644
--- a/tests/node_compat/runner/TODO.md
+++ b/tests/node_compat/runner/TODO.md
@@ -280,7 +280,6 @@ NOTE: This file should not be manually edited. Please edit `tests/node_compat/co
 - [parallel/test-child-process-fork3.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-child-process-fork3.js)
 - [parallel/test-child-process-http-socket-leak.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-child-process-http-socket-leak.js)
 - [parallel/test-child-process-internal.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-child-process-internal.js)
-- [parallel/test-child-process-ipc-next-tick.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-child-process-ipc-next-tick.js)
 - [parallel/test-child-process-ipc.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-child-process-ipc.js)
 - [parallel/test-child-process-no-deprecation.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-child-process-no-deprecation.js)
 - [parallel/test-child-process-pipe-dataflow.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-child-process-pipe-dataflow.js)
@@ -1632,7 +1631,6 @@ NOTE: This file should not be manually edited. Please edit `tests/node_compat/co
 - [parallel/test-icu-minimum-version.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-icu-minimum-version.js)
 - [parallel/test-icu-punycode.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-icu-punycode.js)
 - [parallel/test-icu-stringwidth.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-icu-stringwidth.js)
-- [parallel/test-icu-transcode.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-icu-transcode.js)
 - [parallel/test-inspect-address-in-use.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-inspect-address-in-use.js)
 - [parallel/test-inspect-async-hook-setup-at-inspect.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-inspect-async-hook-setup-at-inspect.js)
 - [parallel/test-inspect-publish-uid.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-inspect-publish-uid.js)
@@ -1769,7 +1767,6 @@ NOTE: This file should not be manually edited. Please edit `tests/node_compat/co
 - [parallel/test-net-autoselectfamily-commandline-option.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-autoselectfamily-commandline-option.js)
 - [parallel/test-net-autoselectfamily-default.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-autoselectfamily-default.js)
 - [parallel/test-net-autoselectfamily-ipv4first.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-autoselectfamily-ipv4first.js)
-- [parallel/test-net-autoselectfamily.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-autoselectfamily.js)
 - [parallel/test-net-better-error-messages-listen.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-better-error-messages-listen.js)
 - [parallel/test-net-binary.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-binary.js)
 - [parallel/test-net-bind-twice.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-bind-twice.js)
@@ -1852,7 +1849,6 @@ NOTE: This file should not be manually edited. Please edit `tests/node_compat/co
 - [parallel/test-net-socket-ready-without-cb.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-socket-ready-without-cb.js)
 - [parallel/test-net-socket-reset-send.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-socket-reset-send.js)
 - [parallel/test-net-socket-reset-twice.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-socket-reset-twice.js)
-- [parallel/test-net-socket-setnodelay.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-socket-setnodelay.js)
 - [parallel/test-net-socket-timeout-unref.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-socket-timeout-unref.js)
 - [parallel/test-net-socket-timeout.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-socket-timeout.js)
 - [parallel/test-net-socket-write-after-close.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-socket-write-after-close.js)
@@ -1881,7 +1877,6 @@ NOTE: This file should not be manually edited. Please edit `tests/node_compat/co
 - [parallel/test-os-homedir-no-envvar.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-os-homedir-no-envvar.js)
 - [parallel/test-os-process-priority.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-os-process-priority.js)
 - [parallel/test-os-userinfo-handles-getter-errors.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-os-userinfo-handles-getter-errors.js)
-- [parallel/test-os.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-os.js)
 - [parallel/test-path-posix-relative-on-windows.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-path-posix-relative-on-windows.js)
 - [parallel/test-pending-deprecation.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-pending-deprecation.js)
 - [parallel/test-perf-gc-crash.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-perf-gc-crash.js)
diff --git a/tests/node_compat/test.ts b/tests/node_compat/test.ts
index f6db4ee1ae..6cb41d2e45 100644
--- a/tests/node_compat/test.ts
+++ b/tests/node_compat/test.ts
@@ -19,6 +19,7 @@ import { magenta } from "@std/fmt/colors";
 import { pooledMap } from "@std/async/pool";
 import { dirname, fromFileUrl, join } from "@std/path";
 import { assertEquals, fail } from "@std/assert";
+import { distinct } from "@std/collections";
 import {
   config,
   getPathsFromTestSuites,
@@ -36,6 +37,9 @@ const testPaths = partitionParallelTestPaths(
     getPathsFromTestSuites(config.ignore),
   ),
 );
+testPaths.sequential = distinct(testPaths.sequential);
+testPaths.parallel = distinct(testPaths.parallel);
+
 const cwd = new URL(".", import.meta.url);
 const windowsIgnorePaths = new Set(
   getPathsFromTestSuites(config.windowsIgnore),
diff --git a/tests/node_compat/test/common/index.js b/tests/node_compat/test/common/index.js
index d2165aecd0..d358ffce5b 100644
--- a/tests/node_compat/test/common/index.js
+++ b/tests/node_compat/test/common/index.js
@@ -473,6 +473,7 @@ const pwdCommand = isWindows ?
 
 module.exports = {
   allowGlobals,
+  defaultAutoSelectFamilyAttemptTimeout: 2500,
   expectsError,
   expectWarning,
   getArrayBufferViews,
diff --git a/tests/node_compat/test/fixtures/child-process-spawn-node.js b/tests/node_compat/test/fixtures/child-process-spawn-node.js
index d403aabf91..7112567e01 100644
--- a/tests/node_compat/test/fixtures/child-process-spawn-node.js
+++ b/tests/node_compat/test/fixtures/child-process-spawn-node.js
@@ -1,5 +1,6 @@
 const assert = require("assert");
 const debug = require('util').debuglog('test');
+const process = require("process");
 
 function onmessage(m) {
   debug("CHILD got message:", m);
diff --git a/tests/node_compat/test/parallel/package.json b/tests/node_compat/test/parallel/package.json
deleted file mode 100644
index 0967ef424b..0000000000
--- a/tests/node_compat/test/parallel/package.json
+++ /dev/null
@@ -1 +0,0 @@
-{}
diff --git a/tests/node_compat/test/parallel/test-child-process-ipc-next-tick.js b/tests/node_compat/test/parallel/test-child-process-ipc-next-tick.js
new file mode 100644
index 0000000000..f511d25004
--- /dev/null
+++ b/tests/node_compat/test/parallel/test-child-process-ipc-next-tick.js
@@ -0,0 +1,46 @@
+// deno-fmt-ignore-file
+// deno-lint-ignore-file
+
+// Copyright Joyent and Node contributors. All rights reserved. MIT license.
+// Taken from Node 18.12.1
+// This file is automatically generated by `tests/node_compat/runner/setup.ts`. Do not modify this file manually.
+
+'use strict';
+const common = require('../common');
+const assert = require('assert');
+const cp = require('child_process');
+const NUM_MESSAGES = 10;
+const values = [];
+
+for (let i = 0; i < NUM_MESSAGES; ++i) {
+  values[i] = i;
+}
+
+if (process.argv[2] === 'child') {
+  const received = values.map(() => { return false; });
+
+  process.on('uncaughtException', common.mustCall((err) => {
+    received[err] = true;
+    const done = received.every((element) => { return element === true; });
+
+    if (done)
+      process.disconnect();
+  }, NUM_MESSAGES));
+
+  process.on('message', (msg) => {
+    // If messages are handled synchronously, throwing should break the IPC
+    // message processing.
+    throw msg;
+  });
+
+  process.send('ready');
+} else {
+  const child = cp.fork(__filename, ['child']);
+
+  child.on('message', common.mustCall((msg) => {
+    assert.strictEqual(msg, 'ready');
+    values.forEach((value) => {
+      child.send(value);
+    });
+  }));
+}
diff --git a/tests/node_compat/test/parallel/test-icu-transcode.js b/tests/node_compat/test/parallel/test-icu-transcode.js
new file mode 100644
index 0000000000..1f5aeb5355
--- /dev/null
+++ b/tests/node_compat/test/parallel/test-icu-transcode.js
@@ -0,0 +1,97 @@
+// deno-fmt-ignore-file
+// deno-lint-ignore-file
+
+// Copyright Joyent and Node contributors. All rights reserved. MIT license.
+// Taken from Node 18.12.1
+// This file is automatically generated by `tests/node_compat/runner/setup.ts`. Do not modify this file manually.
+
+'use strict';
+
+const common = require('../common');
+
+if (!common.hasIntl)
+  common.skip('missing Intl');
+
+const buffer = require('buffer');
+const assert = require('assert');
+const orig = Buffer.from('těst ☕', 'utf8');
+
+// Test Transcoding
+const tests = {
+  'latin1': [0x74, 0x3f, 0x73, 0x74, 0x20, 0x3f],
+  'ascii': [0x74, 0x3f, 0x73, 0x74, 0x20, 0x3f],
+  'ucs2': [0x74, 0x00, 0x1b, 0x01, 0x73,
+           0x00, 0x74, 0x00, 0x20, 0x00,
+           0x15, 0x26]
+};
+
+for (const test in tests) {
+  const dest = buffer.transcode(orig, 'utf8', test);
+  assert.strictEqual(dest.length, tests[test].length, `utf8->${test} length`);
+  for (let n = 0; n < tests[test].length; n++)
+    assert.strictEqual(dest[n], tests[test][n], `utf8->${test} char ${n}`);
+}
+
+{
+  const dest = buffer.transcode(Buffer.from(tests.ucs2), 'ucs2', 'utf8');
+  assert.strictEqual(dest.toString(), orig.toString());
+}
+
+{
+  const utf8 = Buffer.from('€'.repeat(4000), 'utf8');
+  const ucs2 = Buffer.from('€'.repeat(4000), 'ucs2');
+  const utf8_to_ucs2 = buffer.transcode(utf8, 'utf8', 'ucs2');
+  const ucs2_to_utf8 = buffer.transcode(ucs2, 'ucs2', 'utf8');
+  assert.deepStrictEqual(utf8, ucs2_to_utf8);
+  assert.deepStrictEqual(ucs2, utf8_to_ucs2);
+  assert.strictEqual(ucs2_to_utf8.toString('utf8'),
+                     utf8_to_ucs2.toString('ucs2'));
+}
+
+assert.throws(
+  () => buffer.transcode(null, 'utf8', 'ascii'),
+  {
+    name: 'TypeError',
+    code: 'ERR_INVALID_ARG_TYPE',
+    message: 'The "source" argument must be an instance of Buffer ' +
+             'or Uint8Array. Received null'
+  }
+);
+
+assert.throws(
+  () => buffer.transcode(Buffer.from('a'), 'b', 'utf8'),
+  /^Error: Unable to transcode Buffer \[U_ILLEGAL_ARGUMENT_ERROR\]/
+);
+
+assert.throws(
+  () => buffer.transcode(Buffer.from('a'), 'uf8', 'b'),
+  /^Error: Unable to transcode Buffer \[U_ILLEGAL_ARGUMENT_ERROR\]$/
+);
+
+assert.deepStrictEqual(
+  buffer.transcode(Buffer.from('hi', 'ascii'), 'ascii', 'utf16le'),
+  Buffer.from('hi', 'utf16le'));
+assert.deepStrictEqual(
+  buffer.transcode(Buffer.from('hi', 'latin1'), 'latin1', 'utf16le'),
+  Buffer.from('hi', 'utf16le'));
+assert.deepStrictEqual(
+  buffer.transcode(Buffer.from('hä', 'latin1'), 'latin1', 'utf16le'),
+  Buffer.from('hä', 'utf16le'));
+
+// Test that Uint8Array arguments are okay.
+{
+  const uint8array = new Uint8Array([...Buffer.from('hä', 'latin1')]);
+  assert.deepStrictEqual(
+    buffer.transcode(uint8array, 'latin1', 'utf16le'),
+    Buffer.from('hä', 'utf16le'));
+}
+
+{
+  const dest = buffer.transcode(new Uint8Array(), 'utf8', 'latin1');
+  assert.strictEqual(dest.length, 0);
+}
+
+// Test that it doesn't crash
+{
+  buffer.transcode(new buffer.SlowBuffer(1), 'utf16le', 'ucs2');
+}
diff --git a/tests/node_compat/test/parallel/test-net-autoselectfamily.js b/tests/node_compat/test/parallel/test-net-autoselectfamily.js
new file mode 100644
index 0000000000..3b520e6c80
--- /dev/null
+++ b/tests/node_compat/test/parallel/test-net-autoselectfamily.js
@@ -0,0 +1,312 @@
+// deno-fmt-ignore-file
+// deno-lint-ignore-file
+
+// Copyright Joyent and Node contributors. All rights reserved. MIT license.
+// Taken from Node 18.12.1
+// This file is automatically generated by `tests/node_compat/runner/setup.ts`. Do not modify this file manually.
+
+'use strict';
+
+const common = require('../common');
+const { parseDNSPacket, writeDNSPacket } = require('../common/dns');
+
+const assert = require('assert');
+const dgram = require('dgram');
+const { Resolver } = require('dns');
+const { createConnection, createServer } = require('net');
+
+// Test that happy eyeballs algorithm is properly implemented.
+
+// Purposely not using setDefaultAutoSelectFamilyAttemptTimeout here to test the
+// parameter is correctly used in options.
+//
+// Some of the machines in the CI need more time to establish connection
+const autoSelectFamilyAttemptTimeout = common.defaultAutoSelectFamilyAttemptTimeout;
+
+function _lookup(resolver, hostname, options, cb) {
+  resolver.resolve(hostname, 'ANY', (err, replies) => {
+    assert.notStrictEqual(options.family, 4);
+
+    if (err) {
+      return cb(err);
+    }
+
+    const hosts = replies
+      .map((r) => ({ address: r.address, family: r.type === 'AAAA' ? 6 : 4 }))
+      .sort((a, b) => b.family - a.family);
+
+    if (options.all === true) {
+      return cb(null, hosts);
+    }
+
+    return cb(null, hosts[0].address, hosts[0].family);
+  });
+}
+
+function createDnsServer(ipv6Addrs, ipv4Addrs, cb) {
+  if (!Array.isArray(ipv6Addrs)) {
+    ipv6Addrs = [ipv6Addrs];
+  }
+
+  if (!Array.isArray(ipv4Addrs)) {
+    ipv4Addrs = [ipv4Addrs];
+  }
+
+  // Create a DNS server which replies with a AAAA and a A record for the same host
+  const socket = dgram.createSocket('udp4');
+
+  // TODO(kt3k): We use common.mustCallAtLeast instead of common.mustCall
+  // because Deno sends multiple requests to the DNS server.
+  // This can be addressed if Deno.resolveDns supports ANY record type.
+  // See https://github.com/denoland/deno/issues/14492
+  socket.on('message', common.mustCallAtLeast((msg, { address, port }) => {
+    const parsed = parseDNSPacket(msg);
+    const domain = parsed.questions[0].domain;
+    assert.strictEqual(domain, 'example.org');
+
+    socket.send(writeDNSPacket({
+      id: parsed.id,
+      questions: parsed.questions,
+      answers: [
+        ...ipv6Addrs.map((address) => ({ type: 'AAAA', address, ttl: 123, domain: 'example.org' })),
+        ...ipv4Addrs.map((address) => ({ type: 'A', address, ttl: 123, domain: 'example.org' })),
+      ]
+    }), port, address);
+  }));
+
+  socket.bind(0, () => {
+    const resolver = new Resolver();
+    resolver.setServers([`127.0.0.1:${socket.address().port}`]);
+
+    cb({ dnsServer: socket, lookup: _lookup.bind(null, resolver) });
+  });
+}
+
+// Test that IPV4 is reached if IPV6 is not reachable
+{
+  createDnsServer('::1', '127.0.0.1', common.mustCall(function({ dnsServer, lookup }) {
+    const ipv4Server = createServer((socket) => {
+      socket.on('data', common.mustCall(() => {
+        socket.write('response-ipv4');
+        socket.end();
+      }));
+    });
+
+    ipv4Server.listen(0, '127.0.0.1', common.mustCall(() => {
+      const port = ipv4Server.address().port;
+
+      const connection = createConnection({
+        host: 'example.org',
+        port: port,
+        lookup,
+        autoSelectFamily: true,
+        autoSelectFamilyAttemptTimeout,
+      });
+
+      let response = '';
+      connection.setEncoding('utf-8');
+
+      connection.on('ready', common.mustCall(() => {
+        assert.deepStrictEqual(connection.autoSelectFamilyAttemptedAddresses, [`::1:${port}`, `127.0.0.1:${port}`]);
+      }));
+
+      connection.on('data', (chunk) => {
+        response += chunk;
+      });
+
+      connection.on('end', common.mustCall(() => {
+        assert.strictEqual(response, 'response-ipv4');
+        ipv4Server.close();
+        dnsServer.close();
+      }));
+
+      connection.write('request');
+    }));
+  }));
+}
+
+// Test that only the last successful connection is established.
+{
+  createDnsServer(
+    ['2606:4700::6810:85e5', '2606:4700::6810:84e5', "::1"],
+    // TODO(kt3k): Comment out ipv4 addresses to make the test pass faster.
+    // Enable this when Deno.connect() call becomes cancellable.
+    // See https://github.com/denoland/deno/issues/26819
+    // ['104.20.22.46', '104.20.23.46', '127.0.0.1'],
+    ['127.0.0.1'],
+    common.mustCall(function({ dnsServer, lookup }) {
+      const ipv4Server = createServer((socket) => {
+        socket.on('data', common.mustCall(() => {
+          socket.write('response-ipv4');
+          socket.end();
+        }));
+      });
+
+      ipv4Server.listen(0, '127.0.0.1', common.mustCall(() => {
+        const port = ipv4Server.address().port;
+
+        const connection = createConnection({
+          host: 'example.org',
+          port: port,
+          lookup,
+          autoSelectFamily: true,
+          autoSelectFamilyAttemptTimeout,
+        });
+
+        let response = '';
+        connection.setEncoding('utf-8');
+
+        connection.on('ready', common.mustCall(() => {
+          assert.deepStrictEqual(
+            connection.autoSelectFamilyAttemptedAddresses,
+            [
+              `2606:4700::6810:85e5:${port}`,
+              `104.20.22.46:${port}`,
+              `2606:4700::6810:84e5:${port}`,
+              `104.20.23.46:${port}`,
+              `::1:${port}`,
+              `127.0.0.1:${port}`,
+            ]
+          );
+        }));
+
+        connection.on('data', (chunk) => {
+          response += chunk;
+        });
+
+        connection.on('end', common.mustCall(() => {
+          assert.strictEqual(response, 'response-ipv4');
+          ipv4Server.close();
+          dnsServer.close();
+        }));
+
+        connection.write('request');
+      }));
+    })
+  );
+}
+
+// Test that IPV4 is NOT reached if IPV6 is reachable
+if (common.hasIPv6) {
+  createDnsServer('::1', '127.0.0.1', common.mustCall(function({ dnsServer, lookup }) {
+    const ipv4Server = createServer((socket) => {
+      socket.on('data', common.mustNotCall(() => {
+        socket.write('response-ipv4');
+        socket.end();
+      }));
+    });
+
+    const ipv6Server = createServer((socket) => {
+      socket.on('data', common.mustCall(() => {
+        socket.write('response-ipv6');
+        socket.end();
+      }));
+    });
+
+    ipv4Server.listen(0, '127.0.0.1', common.mustCall(() => {
+      const port = ipv4Server.address().port;
+
+      ipv6Server.listen(port, '::1', common.mustCall(() => {
+        const connection = createConnection({
+          host: 'example.org',
+          port,
+          lookup,
+          autoSelectFamily: true,
+          autoSelectFamilyAttemptTimeout,
+        });
+
+        let response = '';
+        connection.setEncoding('utf-8');
+
+        connection.on('ready', common.mustCall(() => {
+          assert.deepStrictEqual(connection.autoSelectFamilyAttemptedAddresses, [`::1:${port}`]);
+        }));
+
+        connection.on('data', (chunk) => {
+          response += chunk;
+        });
+
+        connection.on('end', common.mustCall(() => {
+          assert.strictEqual(response, 'response-ipv6');
+          ipv4Server.close();
+          ipv6Server.close();
+          dnsServer.close();
+        }));
+
+        connection.write('request');
+      }));
+    }));
+  }));
+}
+
+// Test that when all errors are returned when no connections succeeded
+{
+  createDnsServer('::1', '127.0.0.1', common.mustCall(function({ dnsServer, lookup }) {
+    const connection = createConnection({
+      host: 'example.org',
+      port: 10,
+      lookup,
+      autoSelectFamily: true,
+      autoSelectFamilyAttemptTimeout,
+    });
+
+    connection.on('ready', common.mustNotCall());
+    connection.on('error', common.mustCall((error) => {
+      assert.deepStrictEqual(connection.autoSelectFamilyAttemptedAddresses, ['::1:10', '127.0.0.1:10']);
+      assert.strictEqual(error.constructor.name, 'AggregateError');
+      assert.strictEqual(error.errors.length, 2);
+
+      const errors = error.errors.map((e) => e.message);
+      assert.ok(errors.includes('connect ECONNREFUSED 127.0.0.1:10'));
+
+      if (common.hasIPv6) {
+        assert.ok(errors.includes('connect ECONNREFUSED ::1:10'));
+      }
+
+      dnsServer.close();
+    }));
+  }));
+}
+
+// Test that the option can be disabled
+{
+  createDnsServer('::1', '127.0.0.1', common.mustCall(function({ dnsServer, lookup }) {
+    const ipv4Server = createServer((socket) => {
+      socket.on('data', common.mustCall(() => {
+        socket.write('response-ipv4');
+        socket.end();
+      }));
+    });
+
+    ipv4Server.listen(0, '127.0.0.1', common.mustCall(() => {
+      const port = ipv4Server.address().port;
+
+      const connection = createConnection({
+        host: 'example.org',
+        port,
+        lookup,
+        autoSelectFamily: false,
+      });
+
+      connection.on('ready', common.mustNotCall());
+      connection.on('error', common.mustCall((error) => {
+        assert.strictEqual(connection.autoSelectFamilyAttemptedAddresses, undefined);
+
+        if (common.hasIPv6) {
+          assert.strictEqual(error.code, 'ECONNREFUSED');
+          assert.strictEqual(error.message, `connect ECONNREFUSED ::1:${port}`);
+        } else if (error.code === 'EAFNOSUPPORT') {
+          assert.strictEqual(error.message, `connect EAFNOSUPPORT ::1:${port} - Local (undefined:undefined)`);
+        } else if (error.code === 'EUNATCH') {
+          assert.strictEqual(error.message, `connect EUNATCH ::1:${port} - Local (:::0)`);
+        } else {
+          assert.strictEqual(error.code, 'EADDRNOTAVAIL');
+          assert.strictEqual(error.message, `connect EADDRNOTAVAIL ::1:${port} - Local (:::0)`);
+        }
+
+        ipv4Server.close();
+        dnsServer.close();
+      }));
+    }));
+  }));
+}
diff --git a/tests/node_compat/test/parallel/test-net-socket-setnodelay.js b/tests/node_compat/test/parallel/test-net-socket-setnodelay.js
new file mode 100644
index 0000000000..3d11b84528
--- /dev/null
+++ b/tests/node_compat/test/parallel/test-net-socket-setnodelay.js
@@ -0,0 +1,63 @@
+// deno-fmt-ignore-file
+// deno-lint-ignore-file
+
+// Copyright Joyent and Node contributors. All rights reserved. MIT license.
+// Taken from Node 18.12.1
+// This file is automatically generated by `tests/node_compat/runner/setup.ts`. Do not modify this file manually.
+
+'use strict';
+
+const common = require('../common');
+const assert = require('assert');
+const net = require('net');
+
+const truthyValues = [true, 1, 'true', {}, []];
+const falseyValues = [false, 0, ''];
+const genSetNoDelay = (desiredArg) => (enable) => {
+  assert.strictEqual(enable, desiredArg);
+};
+
+// setNoDelay should default to true
+let socket = new net.Socket({
+  handle: {
+    setNoDelay: common.mustCall(genSetNoDelay(true)),
+    readStart() {}
+  }
+});
+socket.setNoDelay();
+
+socket = new net.Socket({
+  handle: {
+    setNoDelay: common.mustCall(genSetNoDelay(true), 1),
+    readStart() {}
+  }
+});
+truthyValues.forEach((testVal) => socket.setNoDelay(testVal));
+
+socket = new net.Socket({
+  handle: {
+    setNoDelay: common.mustNotCall(),
+    readStart() {}
+  }
+});
+falseyValues.forEach((testVal) => socket.setNoDelay(testVal));
+
+socket = new net.Socket({
+  handle: {
+    setNoDelay: common.mustCall(3),
+    readStart() {}
+  }
+});
+truthyValues.concat(falseyValues).concat(truthyValues)
+  .forEach((testVal) => socket.setNoDelay(testVal));
+
+// If a handler doesn't have a setNoDelay function it shouldn't be called.
+// In the case below, if it is called an exception will be thrown
+socket = new net.Socket({
+  handle: {
+    setNoDelay: null,
+    readStart() {}
+  }
+});
+const returned = socket.setNoDelay(true);
+assert.ok(returned instanceof net.Socket);
diff --git a/tests/node_compat/test/parallel/test-os.js b/tests/node_compat/test/parallel/test-os.js
new file mode 100644
index 0000000000..f7c24342ad
--- /dev/null
+++ b/tests/node_compat/test/parallel/test-os.js
@@ -0,0 +1,286 @@
+// deno-fmt-ignore-file
+// deno-lint-ignore-file
+
+// Copyright Joyent and Node contributors. All rights reserved. MIT license.
+// Taken from Node 18.12.1
+// This file is automatically generated by `tests/node_compat/runner/setup.ts`. Do not modify this file manually.
+
+// Copyright Joyent, Inc. and other Node contributors.
+//
+// Permission is hereby granted, free of charge, to any person obtaining a
+// copy of this software and associated documentation files (the
+// "Software"), to deal in the Software without restriction, including
+// without limitation the rights to use, copy, modify, merge, publish,
+// distribute, sublicense, and/or sell copies of the Software, and to permit
+// persons to whom the Software is furnished to do so, subject to the
+// following conditions:
+//
+// The above copyright notice and this permission notice shall be included
+// in all copies or substantial portions of the Software.
+//
+// THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS
+// OR IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF
+// MERCHANTABILITY, FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN
+// NO EVENT SHALL THE AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM,
+// DAMAGES OR OTHER LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR
+// OTHERWISE, ARISING FROM, OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE
+// USE OR OTHER DEALINGS IN THE SOFTWARE.
+
+'use strict';
+const common = require('../common');
+const assert = require('assert');
+const os = require('os');
+const path = require('path');
+const { inspect } = require('util');
+
+const is = {
+  number: (value, key) => {
+    assert(!Number.isNaN(value), `${key} should not be NaN`);
+    assert.strictEqual(typeof value, 'number');
+  },
+  string: (value) => { assert.strictEqual(typeof value, 'string'); },
+  array: (value) => { assert.ok(Array.isArray(value)); },
+  object: (value) => {
+    assert.strictEqual(typeof value, 'object');
+    assert.notStrictEqual(value, null);
+  }
+};
+
+process.env.TMPDIR = '/tmpdir';
+process.env.TMP = '/tmp';
+process.env.TEMP = '/temp';
+if (common.isWindows) {
+  assert.strictEqual(os.tmpdir(), '/temp');
+  process.env.TEMP = '';
+  assert.strictEqual(os.tmpdir(), '/tmp');
+  process.env.TMP = '';
+  const expected = `${process.env.SystemRoot || process.env.windir}\\temp`;
+  assert.strictEqual(os.tmpdir(), expected);
+  process.env.TEMP = '\\temp\\';
+  assert.strictEqual(os.tmpdir(), '\\temp');
+  process.env.TEMP = '\\tmpdir/';
+  assert.strictEqual(os.tmpdir(), '\\tmpdir/');
+  process.env.TEMP = '\\';
+  assert.strictEqual(os.tmpdir(), '\\');
+  process.env.TEMP = 'C:\\';
+  assert.strictEqual(os.tmpdir(), 'C:\\');
+} else {
+  assert.strictEqual(os.tmpdir(), '/tmpdir');
+  process.env.TMPDIR = '';
+  assert.strictEqual(os.tmpdir(), '/tmp');
+  process.env.TMP = '';
+  assert.strictEqual(os.tmpdir(), '/temp');
+  process.env.TEMP = '';
+  assert.strictEqual(os.tmpdir(), '/tmp');
+  process.env.TMPDIR = '/tmpdir/';
+  assert.strictEqual(os.tmpdir(), '/tmpdir');
+  process.env.TMPDIR = '/tmpdir\\';
+  assert.strictEqual(os.tmpdir(), '/tmpdir\\');
+  process.env.TMPDIR = '/';
+  assert.strictEqual(os.tmpdir(), '/');
+}
+
+const endianness = os.endianness();
+is.string(endianness);
+assert.match(endianness, /[BL]E/);
+
+const hostname = os.hostname();
+is.string(hostname);
+assert.ok(hostname.length > 0);
+
+// IBMi process priority is different.
+if (!common.isIBMi) {
+  const DUMMY_PRIORITY = 10;
+  os.setPriority(DUMMY_PRIORITY);
+  const priority = os.getPriority();
+  is.number(priority);
+  assert.strictEqual(priority, DUMMY_PRIORITY);
+}
+
+// On IBMi, os.uptime() returns 'undefined'
+if (!common.isIBMi) {
+  const uptime = os.uptime();
+  is.number(uptime);
+  assert.ok(uptime > 0);
+}
+
+const cpus = os.cpus();
+is.array(cpus);
+assert.ok(cpus.length > 0);
+for (const cpu of cpus) {
+  assert.strictEqual(typeof cpu.model, 'string');
+  assert.strictEqual(typeof cpu.speed, 'number');
+  assert.strictEqual(typeof cpu.times.user, 'number');
+  assert.strictEqual(typeof cpu.times.nice, 'number');
+  assert.strictEqual(typeof cpu.times.sys, 'number');
+  assert.strictEqual(typeof cpu.times.idle, 'number');
+  assert.strictEqual(typeof cpu.times.irq, 'number');
+}
+
+const type = os.type();
+is.string(type);
+assert.ok(type.length > 0);
+
+const release = os.release();
+is.string(release);
+assert.ok(release.length > 0);
+// TODO: Check format on more than just AIX
+if (common.isAIX)
+  assert.match(release, /^\d+\.\d+$/);
+
+const platform = os.platform();
+is.string(platform);
+assert.ok(platform.length > 0);
+
+const arch = os.arch();
+is.string(arch);
+assert.ok(arch.length > 0);
+
+if (!common.isSunOS) {
+  // not implemented yet
+  assert.ok(os.loadavg().length > 0);
+  assert.ok(os.freemem() > 0);
+  assert.ok(os.totalmem() > 0);
+}
+
+const interfaces = os.networkInterfaces();
+switch (platform) {
+  case 'linux': {
+    const filter = (e) =>
+      e.address === '127.0.0.1' &&
+      e.netmask === '255.0.0.0';
+
+    const actual = interfaces.lo.filter(filter);
+    const expected = [{
+      address: '127.0.0.1',
+      netmask: '255.0.0.0',
+      family: 'IPv4',
+      mac: '00:00:00:00:00:00',
+      internal: true,
+      cidr: '127.0.0.1/8'
+    }];
+    assert.deepStrictEqual(actual, expected);
+    break;
+  }
+  case 'win32': {
+    const filter = (e) =>
+      e.address === '127.0.0.1';
+
+    const actual = interfaces['Loopback Pseudo-Interface 1'].filter(filter);
+    const expected = [{
+      address: '127.0.0.1',
+      netmask: '255.0.0.0',
+      family: 'IPv4',
+      mac: '00:00:00:00:00:00',
+      internal: true,
+      cidr: '127.0.0.1/8'
+    }];
+    assert.deepStrictEqual(actual, expected);
+    break;
+  }
+}
+const netmaskToCIDRSuffixMap = new Map(Object.entries({
+  '255.0.0.0': 8,
+  '255.255.255.0': 24,
+  'ffff:ffff:ffff:ffff::': 64,
+  'ffff:ffff:ffff:ffff:ffff:ffff:ffff:ffff': 128
+}));
+
+Object.values(interfaces)
+  .flat(Infinity)
+  .map((v) => ({ v, mask: netmaskToCIDRSuffixMap.get(v.netmask) }))
+  .forEach(({ v, mask }) => {
+    assert.ok('cidr' in v, `"cidr" prop not found in ${inspect(v)}`);
+    if (mask) {
+      assert.strictEqual(v.cidr, `${v.address}/${mask}`);
+    }
+  });
+
+const EOL = os.EOL;
+if (common.isWindows) {
+  assert.strictEqual(EOL, '\r\n');
+} else {
+  assert.strictEqual(EOL, '\n');
+}
+
+const home = os.homedir();
+is.string(home);
+assert.ok(home.includes(path.sep));
+
+const version = os.version();
+assert.strictEqual(typeof version, 'string');
+assert(version);
+
+if (common.isWindows && process.env.USERPROFILE) {
+  assert.strictEqual(home, process.env.USERPROFILE);
+  delete process.env.USERPROFILE;
+  assert.ok(os.homedir().includes(path.sep));
+  process.env.USERPROFILE = home;
+} else if (!common.isWindows && process.env.HOME) {
+  assert.strictEqual(home, process.env.HOME);
+  delete process.env.HOME;
+  assert.ok(os.homedir().includes(path.sep));
+  process.env.HOME = home;
+}
+
+const pwd = os.userInfo();
+is.object(pwd);
+const pwdBuf = os.userInfo({ encoding: 'buffer' });
+
+if (common.isWindows) {
+  assert.strictEqual(pwd.uid, -1);
+  assert.strictEqual(pwd.gid, -1);
+  assert.strictEqual(pwd.shell, null);
+  assert.strictEqual(pwdBuf.uid, -1);
+  assert.strictEqual(pwdBuf.gid, -1);
+  assert.strictEqual(pwdBuf.shell, null);
+} else {
+  is.number(pwd.uid);
+  is.number(pwd.gid);
+  assert.strictEqual(typeof pwd.shell, 'string');
+  // It's possible for /etc/passwd to leave the user's shell blank.
+  if (pwd.shell.length > 0) {
+    assert(pwd.shell.includes(path.sep));
+  }
+  assert.strictEqual(pwd.uid, pwdBuf.uid);
+  assert.strictEqual(pwd.gid, pwdBuf.gid);
+  assert.strictEqual(pwd.shell, pwdBuf.shell.toString('utf8'));
+}
+
+is.string(pwd.username);
+assert.ok(pwd.homedir.includes(path.sep));
+assert.strictEqual(pwd.username, pwdBuf.username.toString('utf8'));
+assert.strictEqual(pwd.homedir, pwdBuf.homedir.toString('utf8'));
+
+assert.strictEqual(`${os.hostname}`, os.hostname());
+assert.strictEqual(`${os.homedir}`, os.homedir());
+assert.strictEqual(`${os.release}`, os.release());
+assert.strictEqual(`${os.type}`, os.type());
+assert.strictEqual(`${os.endianness}`, os.endianness());
+assert.strictEqual(`${os.tmpdir}`, os.tmpdir());
+assert.strictEqual(`${os.arch}`, os.arch());
+assert.strictEqual(`${os.platform}`, os.platform());
+assert.strictEqual(`${os.version}`, os.version());
+assert.strictEqual(`${os.machine}`, os.machine());
+assert.strictEqual(+os.totalmem, os.totalmem());
+
+// Assert that the following values are coercible to numbers.
+// On IBMi, os.uptime() returns 'undefined'
+if (!common.isIBMi) {
+  is.number(+os.uptime, 'uptime');
+  is.number(os.uptime(), 'uptime');
+}
+
+is.number(+os.availableParallelism, 'availableParallelism');
+is.number(os.availableParallelism(), 'availableParallelism');
+is.number(+os.freemem, 'freemem');
+is.number(os.freemem(), 'freemem');
+
+const devNull = os.devNull;
+if (common.isWindows) {
+  assert.strictEqual(devNull, '\\\\.\\nul');
+} else {
+  assert.strictEqual(devNull, '/dev/null');
+}
+
+assert.ok(os.availableParallelism() > 0);
diff --git a/tests/node_compat/test/pseudo-tty/package.json b/tests/node_compat/test/pseudo-tty/package.json
deleted file mode 100644
index 0967ef424b..0000000000
--- a/tests/node_compat/test/pseudo-tty/package.json
+++ /dev/null
@@ -1 +0,0 @@
-{}
diff --git a/tests/node_compat/test/pummel/package.json b/tests/node_compat/test/pummel/package.json
deleted file mode 100644
index 0967ef424b..0000000000
--- a/tests/node_compat/test/pummel/package.json
+++ /dev/null
@@ -1 +0,0 @@
-{}
diff --git a/tests/node_compat/test/sequential/package.json b/tests/node_compat/test/sequential/package.json
deleted file mode 100644
index 0967ef424b..0000000000
--- a/tests/node_compat/test/sequential/package.json
+++ /dev/null
@@ -1 +0,0 @@
-{}
diff --git a/tests/registry/jsr/@denotest/multiple-exports/1.0.0/add.ts b/tests/registry/jsr/@denotest/multiple-exports/1.0.0/add.ts
new file mode 100644
index 0000000000..de02f69024
--- /dev/null
+++ b/tests/registry/jsr/@denotest/multiple-exports/1.0.0/add.ts
@@ -0,0 +1 @@
+export * from "jsr:@denotest/add@1";
diff --git a/tests/registry/jsr/@denotest/multiple-exports/1.0.0/data.json b/tests/registry/jsr/@denotest/multiple-exports/1.0.0/data.json
new file mode 100644
index 0000000000..885e71c6cc
--- /dev/null
+++ b/tests/registry/jsr/@denotest/multiple-exports/1.0.0/data.json
@@ -0,0 +1,3 @@
+{
+  "a": 1
+}
\ No newline at end of file
diff --git a/tests/registry/jsr/@denotest/multiple-exports/1.0.0/subtract.ts b/tests/registry/jsr/@denotest/multiple-exports/1.0.0/subtract.ts
new file mode 100644
index 0000000000..215c42310d
--- /dev/null
+++ b/tests/registry/jsr/@denotest/multiple-exports/1.0.0/subtract.ts
@@ -0,0 +1 @@
+export * from "jsr:@denotest/subtract@1";
diff --git a/tests/registry/jsr/@denotest/multiple-exports/1.0.0_meta.json b/tests/registry/jsr/@denotest/multiple-exports/1.0.0_meta.json
new file mode 100644
index 0000000000..d9f58b9a61
--- /dev/null
+++ b/tests/registry/jsr/@denotest/multiple-exports/1.0.0_meta.json
@@ -0,0 +1,7 @@
+{
+  "exports": {
+    "./add": "./add.ts",
+    "./subtract": "./subtract.ts",
+    "./data-json": "./data.json"
+  }
+}
diff --git a/tests/registry/jsr/@denotest/multiple-exports/meta.json b/tests/registry/jsr/@denotest/multiple-exports/meta.json
new file mode 100644
index 0000000000..02601e4d0d
--- /dev/null
+++ b/tests/registry/jsr/@denotest/multiple-exports/meta.json
@@ -0,0 +1,5 @@
+{
+  "versions": {
+    "1.0.0": {}
+  }
+}
diff --git a/tests/registry/jsr/@denotest/type-only-import/1.0.0/foo.ts b/tests/registry/jsr/@denotest/type-only-import/1.0.0/foo.ts
new file mode 100644
index 0000000000..4e09512c03
--- /dev/null
+++ b/tests/registry/jsr/@denotest/type-only-import/1.0.0/foo.ts
@@ -0,0 +1,3 @@
+export interface Foo {
+  bar: string;
+}
\ No newline at end of file
diff --git a/tests/registry/jsr/@denotest/type-only-import/1.0.0/mod.ts b/tests/registry/jsr/@denotest/type-only-import/1.0.0/mod.ts
new file mode 100644
index 0000000000..093a57d8a1
--- /dev/null
+++ b/tests/registry/jsr/@denotest/type-only-import/1.0.0/mod.ts
@@ -0,0 +1,3 @@
+import type { Foo } from "./foo.ts";
+
+export const foo: Foo = { bar: "foo" };
\ No newline at end of file
diff --git a/tests/registry/jsr/@denotest/type-only-import/1.0.0_meta.json b/tests/registry/jsr/@denotest/type-only-import/1.0.0_meta.json
new file mode 100644
index 0000000000..631a18d0e5
--- /dev/null
+++ b/tests/registry/jsr/@denotest/type-only-import/1.0.0_meta.json
@@ -0,0 +1,5 @@
+{
+  "exports": {
+    ".": "./mod.ts"
+  }
+}
diff --git a/tests/registry/jsr/@denotest/type-only-import/meta.json b/tests/registry/jsr/@denotest/type-only-import/meta.json
new file mode 100644
index 0000000000..02601e4d0d
--- /dev/null
+++ b/tests/registry/jsr/@denotest/type-only-import/meta.json
@@ -0,0 +1,5 @@
+{
+  "versions": {
+    "1.0.0": {}
+  }
+}
diff --git a/tests/registry/jsr/@denotest/unstable/1.0.0-beta.1/mod.ts b/tests/registry/jsr/@denotest/unstable/1.0.0-beta.1/mod.ts
new file mode 100644
index 0000000000..de63686189
--- /dev/null
+++ b/tests/registry/jsr/@denotest/unstable/1.0.0-beta.1/mod.ts
@@ -0,0 +1,3 @@
+export function doThing() {
+    return "thing";
+}
\ No newline at end of file
diff --git a/tests/registry/jsr/@denotest/unstable/1.0.0-beta.1_meta.json b/tests/registry/jsr/@denotest/unstable/1.0.0-beta.1_meta.json
new file mode 100644
index 0000000000..631a18d0e5
--- /dev/null
+++ b/tests/registry/jsr/@denotest/unstable/1.0.0-beta.1_meta.json
@@ -0,0 +1,5 @@
+{
+  "exports": {
+    ".": "./mod.ts"
+  }
+}
diff --git a/tests/registry/jsr/@denotest/unstable/1.0.0-beta.2/mod.ts b/tests/registry/jsr/@denotest/unstable/1.0.0-beta.2/mod.ts
new file mode 100644
index 0000000000..4e599641ef
--- /dev/null
+++ b/tests/registry/jsr/@denotest/unstable/1.0.0-beta.2/mod.ts
@@ -0,0 +1,3 @@
+export function doThing() {
+    return "thing2";
+}
\ No newline at end of file
diff --git a/tests/registry/jsr/@denotest/unstable/1.0.0-beta.2_meta.json b/tests/registry/jsr/@denotest/unstable/1.0.0-beta.2_meta.json
new file mode 100644
index 0000000000..631a18d0e5
--- /dev/null
+++ b/tests/registry/jsr/@denotest/unstable/1.0.0-beta.2_meta.json
@@ -0,0 +1,5 @@
+{
+  "exports": {
+    ".": "./mod.ts"
+  }
+}
diff --git a/tests/registry/jsr/@denotest/unstable/meta.json b/tests/registry/jsr/@denotest/unstable/meta.json
new file mode 100644
index 0000000000..7c5c9971ef
--- /dev/null
+++ b/tests/registry/jsr/@denotest/unstable/meta.json
@@ -0,0 +1,6 @@
+{
+  "versions": {
+    "1.0.0-beta.1": {},
+    "1.0.0-beta.2": {}
+  }
+}
diff --git a/tests/registry/npm-private3/@denotest3/basic/1.0.0/main.d.mts b/tests/registry/npm-private3/@denotest3/basic/1.0.0/main.d.mts
new file mode 100644
index 0000000000..29da1e6d7b
--- /dev/null
+++ b/tests/registry/npm-private3/@denotest3/basic/1.0.0/main.d.mts
@@ -0,0 +1,3 @@
+export declare function setValue(val: number): void;
+export declare function getValue(): number;
+export declare const url: string;
diff --git a/tests/registry/npm-private3/@denotest3/basic/1.0.0/main.mjs b/tests/registry/npm-private3/@denotest3/basic/1.0.0/main.mjs
new file mode 100644
index 0000000000..0a44f75859
--- /dev/null
+++ b/tests/registry/npm-private3/@denotest3/basic/1.0.0/main.mjs
@@ -0,0 +1,11 @@
+let value = 0;
+
+export function setValue(newValue) {
+  value = newValue;
+}
+
+export function getValue() {
+  return value;
+}
+
+export const url = import.meta.url;
diff --git a/tests/registry/npm-private3/@denotest3/basic/1.0.0/other.mjs b/tests/registry/npm-private3/@denotest3/basic/1.0.0/other.mjs
new file mode 100644
index 0000000000..00ed99da45
--- /dev/null
+++ b/tests/registry/npm-private3/@denotest3/basic/1.0.0/other.mjs
@@ -0,0 +1,3 @@
+export function hello() {
+    return "hello, world!";
+}
\ No newline at end of file
diff --git a/tests/registry/npm-private3/@denotest3/basic/1.0.0/package.json b/tests/registry/npm-private3/@denotest3/basic/1.0.0/package.json
new file mode 100644
index 0000000000..ce6ea33830
--- /dev/null
+++ b/tests/registry/npm-private3/@denotest3/basic/1.0.0/package.json
@@ -0,0 +1,7 @@
+{
+  "name": "@denotest3/basic",
+  "version": "1.0.0",
+  "type": "module",
+  "main": "main.mjs",
+  "types": "main.d.mts"
+}
diff --git a/tests/registry/npm/@denotest/better-say-hello/1.0.0/say-hello.js b/tests/registry/npm/@denotest/better-say-hello/1.0.0/say-hello.js
index 0b8d63cf48..5243d49026 100644
--- a/tests/registry/npm/@denotest/better-say-hello/1.0.0/say-hello.js
+++ b/tests/registry/npm/@denotest/better-say-hello/1.0.0/say-hello.js
@@ -1,2 +1,2 @@
 import { sayBetterHello } from "./index.js";
-sayBetterHello();
\ No newline at end of file
+sayBetterHello();
diff --git a/tests/registry/npm/@denotest/bin-created-by-lifecycle/1.0.0/install.mjs b/tests/registry/npm/@denotest/bin-created-by-lifecycle/1.0.0/install.mjs
new file mode 100644
index 0000000000..31020fcdf9
--- /dev/null
+++ b/tests/registry/npm/@denotest/bin-created-by-lifecycle/1.0.0/install.mjs
@@ -0,0 +1,3 @@
+import * as fs from "node:fs";
+
+fs.writeFileSync("./testbin.js", "#!/usr/bin/env node\nconsole.log('run testbin');");
\ No newline at end of file
diff --git a/tests/registry/npm/@denotest/bin-created-by-lifecycle/1.0.0/package.json b/tests/registry/npm/@denotest/bin-created-by-lifecycle/1.0.0/package.json
new file mode 100644
index 0000000000..ad8dea002e
--- /dev/null
+++ b/tests/registry/npm/@denotest/bin-created-by-lifecycle/1.0.0/package.json
@@ -0,0 +1,10 @@
+{
+  "name": "@denotest/bin-created-by-lifecycle",
+  "version": "1.0.0",
+  "scripts": {
+    "install": "node install.mjs"
+  },
+  "bin": {
+    "testbin": "testbin.js"
+  }
+}
\ No newline at end of file
diff --git a/tests/registry/npm/@denotest/cjs-multiple-exports/1.0.0/package.json b/tests/registry/npm/@denotest/cjs-multiple-exports/1.0.0/package.json
new file mode 100644
index 0000000000..43f07a2351
--- /dev/null
+++ b/tests/registry/npm/@denotest/cjs-multiple-exports/1.0.0/package.json
@@ -0,0 +1,8 @@
+{
+  "name": "@denotest/cjs-multiple-exports",
+  "version": "1.0.0",
+  "exports": {
+    ".": "./src/index.js",
+    "./add": "./src/add.js"
+  }
+}
\ No newline at end of file
diff --git a/tests/registry/npm/@denotest/cjs-multiple-exports/1.0.0/src/add.js b/tests/registry/npm/@denotest/cjs-multiple-exports/1.0.0/src/add.js
new file mode 100644
index 0000000000..42c8a7c604
--- /dev/null
+++ b/tests/registry/npm/@denotest/cjs-multiple-exports/1.0.0/src/add.js
@@ -0,0 +1,3 @@
+module.exports = function add(a, b) {
+  return a + b;
+};
\ No newline at end of file
diff --git a/tests/registry/npm/@denotest/cjs-multiple-exports/1.0.0/src/index.js b/tests/registry/npm/@denotest/cjs-multiple-exports/1.0.0/src/index.js
new file mode 100644
index 0000000000..432ed652ed
--- /dev/null
+++ b/tests/registry/npm/@denotest/cjs-multiple-exports/1.0.0/src/index.js
@@ -0,0 +1,3 @@
+module.exports = {
+  hello: "world"
+};
\ No newline at end of file
diff --git a/tests/registry/npm/@denotest/install-launch-cjs-temp-dir/1.0.0/install.js b/tests/registry/npm/@denotest/install-launch-cjs-temp-dir/1.0.0/install.js
new file mode 100644
index 0000000000..61aadeb839
--- /dev/null
+++ b/tests/registry/npm/@denotest/install-launch-cjs-temp-dir/1.0.0/install.js
@@ -0,0 +1,12 @@
+const tempDir = Deno.makeTempDirSync();
+try {
+  // should work requiring these because this was launched via a node binary entrypoint
+  Deno.writeTextFileSync(`${tempDir}/index.js`, "module.exports = require('./other');");
+  Deno.writeTextFileSync(`${tempDir}/other.js`, "module.exports = (a, b) => a + b;");
+  const add = require(`${tempDir}/index.js`);
+  if (add(1, 2) !== 3) {
+    throw new Error("FAILED");
+  }
+} finally {
+  Deno.removeSync(tempDir, { recursive: true });
+}
diff --git a/tests/registry/npm/@denotest/install-launch-cjs-temp-dir/1.0.0/package.json b/tests/registry/npm/@denotest/install-launch-cjs-temp-dir/1.0.0/package.json
new file mode 100644
index 0000000000..c3cf8dc4c3
--- /dev/null
+++ b/tests/registry/npm/@denotest/install-launch-cjs-temp-dir/1.0.0/package.json
@@ -0,0 +1,7 @@
+{
+  "name": "@denotest/install-launch-cjs-temp-dir",
+  "version": "1.0.0",
+  "scripts": {
+    "install": "node install.js"
+  }
+}
\ No newline at end of file
diff --git a/tests/registry/npm/@denotest/install-no-ext/1.0.0/install/check.js b/tests/registry/npm/@denotest/install-no-ext/1.0.0/install/check.js
new file mode 100644
index 0000000000..7d55c2481d
--- /dev/null
+++ b/tests/registry/npm/@denotest/install-no-ext/1.0.0/install/check.js
@@ -0,0 +1 @@
+require("./output");
diff --git a/tests/registry/npm/@denotest/install-no-ext/1.0.0/install/index.js b/tests/registry/npm/@denotest/install-no-ext/1.0.0/install/index.js
new file mode 100644
index 0000000000..7d55c2481d
--- /dev/null
+++ b/tests/registry/npm/@denotest/install-no-ext/1.0.0/install/index.js
@@ -0,0 +1 @@
+require("./output");
diff --git a/tests/registry/npm/@denotest/install-no-ext/1.0.0/install/output.js b/tests/registry/npm/@denotest/install-no-ext/1.0.0/install/output.js
new file mode 100644
index 0000000000..69668cd625
--- /dev/null
+++ b/tests/registry/npm/@denotest/install-no-ext/1.0.0/install/output.js
@@ -0,0 +1 @@
+console.log("SUCCESS");
diff --git a/tests/registry/npm/@denotest/install-no-ext/1.0.0/package.json b/tests/registry/npm/@denotest/install-no-ext/1.0.0/package.json
new file mode 100644
index 0000000000..b9abed1f6e
--- /dev/null
+++ b/tests/registry/npm/@denotest/install-no-ext/1.0.0/package.json
@@ -0,0 +1,7 @@
+{
+  "name": "@denotest/install-no-ext",
+  "version": "1.0.0",
+  "scripts": {
+    "install": "node install/check && node install"
+  }
+}
\ No newline at end of file
diff --git a/tests/registry/npm/@denotest/node-addon/1.0.0/package.json b/tests/registry/npm/@denotest/node-addon/1.0.0/package.json
index 5d50aa119a..d730e3dd03 100644
--- a/tests/registry/npm/@denotest/node-addon/1.0.0/package.json
+++ b/tests/registry/npm/@denotest/node-addon/1.0.0/package.json
@@ -2,7 +2,7 @@
   "name": "@denotest/node-addon",
   "version": "1.0.0",
   "scripts": {
-    "install": "node-gyp configure build"
+    "install": "node-gyp configure --verbose build"
   },
   "dependencies": {
     "node-gyp": "10.1.0"
diff --git a/tests/registry/npm/@denotest/node-lifecycle-scripts/1.0.0/index.js b/tests/registry/npm/@denotest/node-lifecycle-scripts/1.0.0/index.js
index 4eb9b107a0..242fe92f57 100644
--- a/tests/registry/npm/@denotest/node-lifecycle-scripts/1.0.0/index.js
+++ b/tests/registry/npm/@denotest/node-lifecycle-scripts/1.0.0/index.js
@@ -1,5 +1,3 @@
-modules.export = {
+module.exports = {
   value: 42
 };
-
-console.log('index.js', modules.export.value);
\ No newline at end of file
diff --git a/tests/registry/npm/@denotest/node-lifecycle-scripts/1.0.0/package.json b/tests/registry/npm/@denotest/node-lifecycle-scripts/1.0.0/package.json
index 3c6fa005fe..085ab6414a 100644
--- a/tests/registry/npm/@denotest/node-lifecycle-scripts/1.0.0/package.json
+++ b/tests/registry/npm/@denotest/node-lifecycle-scripts/1.0.0/package.json
@@ -6,6 +6,7 @@
     "install": "echo install && cli-esm 'hello from install script'",
     "postinstall": "echo postinstall && npx cowsay postinstall"
   },
+  "exports": "./index.js",
   "dependencies": {
     "@denotest/bin": "1.0.0"
   }
diff --git a/tests/registry/npm/@denotest/print-npm-user-agent/1.0.0/index.js b/tests/registry/npm/@denotest/print-npm-user-agent/1.0.0/index.js
new file mode 100644
index 0000000000..b835b8e25e
--- /dev/null
+++ b/tests/registry/npm/@denotest/print-npm-user-agent/1.0.0/index.js
@@ -0,0 +1,2 @@
+#!/usr/bin/env node
+console.log(`npm_config_user_agent: ${process.env["npm_config_user_agent"]}`);
\ No newline at end of file
diff --git a/tests/registry/npm/@denotest/print-npm-user-agent/1.0.0/package.json b/tests/registry/npm/@denotest/print-npm-user-agent/1.0.0/package.json
new file mode 100644
index 0000000000..9071173467
--- /dev/null
+++ b/tests/registry/npm/@denotest/print-npm-user-agent/1.0.0/package.json
@@ -0,0 +1,10 @@
+{
+  "name": "@denotest/print-npm-user-agent",
+  "version": "1.0.0",
+  "bin": {
+    "print-npm-user-agent": "index.js"
+  },
+  "scripts": {
+    "postinstall": "echo postinstall && node index.js && exit 1"
+  }
+}
\ No newline at end of file
diff --git a/tests/registry/npm/@denotest/say-hello/1.0.0/say-hello.js b/tests/registry/npm/@denotest/say-hello/1.0.0/say-hello.js
index 8751b8e47b..66d02cde56 100644
--- a/tests/registry/npm/@denotest/say-hello/1.0.0/say-hello.js
+++ b/tests/registry/npm/@denotest/say-hello/1.0.0/say-hello.js
@@ -1,2 +1,5 @@
 import { sayHello } from "./index.js";
-console.log(sayHello());
\ No newline at end of file
+console.log(sayHello());
+import path from "node:path";
+import fs from "node:fs";
+fs.writeSync(fs.openSync(path.join(process.env.INIT_CWD, "say-hello-output.txt"), "w"), sayHello());
diff --git a/tests/registry/npm/@denotest/type-commonjs/1.0.0/index.js b/tests/registry/npm/@denotest/type-commonjs/1.0.0/index.js
index cb0ff5c3b5..d3f80a0495 100644
--- a/tests/registry/npm/@denotest/type-commonjs/1.0.0/index.js
+++ b/tests/registry/npm/@denotest/type-commonjs/1.0.0/index.js
@@ -1 +1,5 @@
-export {};
+// this module is declared as CommonJS, but during loading we'll
+// discover it's ESM and load it fine
+export function add(a, b) {
+  return a + b;
+}
diff --git a/tests/registry/npm/@types/prop-types/prop-types-15.7.13.tgz b/tests/registry/npm/@types/prop-types/prop-types-15.7.13.tgz
new file mode 100644
index 0000000000..813b6795bf
Binary files /dev/null and b/tests/registry/npm/@types/prop-types/prop-types-15.7.13.tgz differ
diff --git a/tests/registry/npm/@types/prop-types/registry.json b/tests/registry/npm/@types/prop-types/registry.json
new file mode 100644
index 0000000000..3c80e16462
--- /dev/null
+++ b/tests/registry/npm/@types/prop-types/registry.json
@@ -0,0 +1,48 @@
+{
+  "name": "@types/prop-types",
+  "dist-tags": { "latest": "15.7.13" },
+  "versions": {
+    "15.7.13": {
+      "name": "@types/prop-types",
+      "version": "15.7.13",
+      "license": "MIT",
+      "_id": "@types/prop-types@15.7.13",
+      "dist": {
+        "shasum": "2af91918ee12d9d32914feb13f5326658461b451",
+        "tarball": "http://localhost:4260/@types/prop-types/prop-types-15.7.13.tgz",
+        "fileCount": 5,
+        "integrity": "sha512-hCZTSvwbzWGvhqxp/RqVqwU999pBf2vp7hzIjiYOsl8wqOmUxkQ6ddw1cV3l8811+kdUFus/q4d1Y3E3SyEifA==",
+        "signatures": [
+          {
+            "sig": "MEUCIQCz+S+fZxW5ahdAmLsMoCnFlj4QvsEH0h70sXmSVc1EDgIgBDq1TH20PzRBFVHHY3gRc7JeNsAOozAmrQqCy+v1syk=",
+            "keyid": "SHA256:jl3bwswu80PjjokCgh0o2w5c2U4LhQAE57gj9cz1kzA"
+          }
+        ],
+        "unpackedSize": 6965
+      },
+      "main": "",
+      "types": "index.d.ts",
+      "scripts": {},
+      "repository": {
+        "url": "https://github.com/DefinitelyTyped/DefinitelyTyped.git",
+        "type": "git",
+        "directory": "types/prop-types"
+      },
+      "description": "TypeScript definitions for prop-types",
+      "directories": {},
+      "dependencies": {},
+      "_hasShrinkwrap": false,
+      "typeScriptVersion": "4.8",
+      "typesPublisherContentHash": "463997a2d1b4bb7e18554d9d12146cc74169e8bda6a4b9008306c38797ae14d3"
+    }
+  },
+  "license": "MIT",
+  "homepage": "https://github.com/DefinitelyTyped/DefinitelyTyped/tree/master/types/prop-types",
+  "repository": {
+    "url": "https://github.com/DefinitelyTyped/DefinitelyTyped.git",
+    "type": "git",
+    "directory": "types/prop-types"
+  },
+  "description": "TypeScript definitions for prop-types",
+  "readmeFilename": ""
+}
diff --git a/tests/registry/npm/@types/react/react-18.3.10.tgz b/tests/registry/npm/@types/react/react-18.3.10.tgz
new file mode 100644
index 0000000000..7ce743af94
Binary files /dev/null and b/tests/registry/npm/@types/react/react-18.3.10.tgz differ
diff --git a/tests/registry/npm/@types/react/registry.json b/tests/registry/npm/@types/react/registry.json
new file mode 100644
index 0000000000..4046c16980
--- /dev/null
+++ b/tests/registry/npm/@types/react/registry.json
@@ -0,0 +1,71 @@
+{
+  "name": "@types/react",
+  "dist-tags": { "latest": "18.3.10" },
+  "versions": {
+    "18.3.10": {
+      "name": "@types/react",
+      "version": "18.3.10",
+      "license": "MIT",
+      "_id": "@types/react@18.3.10",
+      "dist": {
+        "shasum": "6edc26dc22ff8c9c226d3c7bf8357b013c842219",
+        "tarball": "http://localhost:4260/@types/react/react-18.3.10.tgz",
+        "fileCount": 17,
+        "integrity": "sha512-02sAAlBnP39JgXwkAq3PeU9DVaaGpZyF3MGcC0MKgQVkZor5IiiDAipVaxQHtDJAmO4GIy/rVBy/LzVj76Cyqg==",
+        "signatures": [
+          {
+            "sig": "MEUCIF6O9Y11lCvdqbD+e81mjGbAGN3pZa2cxxwi5Z+3bQr6AiEA0tDSc8Y9i7TjXbsZ2SnO/taFI6v99xnkZRDv5m6to7k=",
+            "keyid": "SHA256:jl3bwswu80PjjokCgh0o2w5c2U4LhQAE57gj9cz1kzA"
+          }
+        ],
+        "unpackedSize": 438614
+      },
+      "main": "",
+      "types": "index.d.ts",
+      "exports": {
+        ".": {
+          "types": { "default": "./index.d.ts" },
+          "types@<=5.0": { "default": "./ts5.0/index.d.ts" }
+        },
+        "./canary": {
+          "types": { "default": "./canary.d.ts" },
+          "types@<=5.0": { "default": "./ts5.0/canary.d.ts" }
+        },
+        "./jsx-runtime": {
+          "types": { "default": "./jsx-runtime.d.ts" },
+          "types@<=5.0": { "default": "./ts5.0/jsx-runtime.d.ts" }
+        },
+        "./experimental": {
+          "types": { "default": "./experimental.d.ts" },
+          "types@<=5.0": { "default": "./ts5.0/experimental.d.ts" }
+        },
+        "./package.json": "./package.json",
+        "./jsx-dev-runtime": {
+          "types": { "default": "./jsx-dev-runtime.d.ts" },
+          "types@<=5.0": { "default": "./ts5.0/jsx-dev-runtime.d.ts" }
+        }
+      },
+      "scripts": {},
+      "repository": {
+        "url": "https://github.com/DefinitelyTyped/DefinitelyTyped.git",
+        "type": "git",
+        "directory": "types/react"
+      },
+      "description": "TypeScript definitions for react",
+      "directories": {},
+      "dependencies": { "csstype": "^3.0.2", "@types/prop-types": "*" },
+      "_hasShrinkwrap": false,
+      "typeScriptVersion": "4.8",
+      "typesPublisherContentHash": "3fbf914f5052668104237c78a8f67cca37176346a3caed94eea6d5c504795f08"
+    }
+  },
+  "license": "MIT",
+  "homepage": "https://github.com/DefinitelyTyped/DefinitelyTyped/tree/master/types/react",
+  "repository": {
+    "url": "https://github.com/DefinitelyTyped/DefinitelyTyped.git",
+    "type": "git",
+    "directory": "types/react"
+  },
+  "description": "TypeScript definitions for react",
+  "readmeFilename": ""
+}
diff --git a/tests/registry/npm/csstype/csstype-3.1.3.tgz b/tests/registry/npm/csstype/csstype-3.1.3.tgz
new file mode 100644
index 0000000000..fb04d02887
Binary files /dev/null and b/tests/registry/npm/csstype/csstype-3.1.3.tgz differ
diff --git a/tests/registry/npm/csstype/registry.json b/tests/registry/npm/csstype/registry.json
index cc3eb9f999..eb44582a68 100644
--- a/tests/registry/npm/csstype/registry.json
+++ b/tests/registry/npm/csstype/registry.json
@@ -2,7 +2,7 @@
   "name": "csstype",
   "description": "Strict TypeScript and Flow types for style based on MDN data",
   "dist-tags": {
-    "latest": "2.6.20",
+    "latest": "3.1.3",
     "version-2": "2.6.20"
   },
   "versions": {
@@ -73,6 +73,82 @@
       },
       "directories": {},
       "_hasShrinkwrap": false
+    },
+    "3.1.3": {
+      "name": "csstype",
+      "version": "3.1.3",
+      "main": "",
+      "types": "index.d.ts",
+      "description": "Strict TypeScript and Flow types for style based on MDN data",
+      "repository": {
+        "type": "git",
+        "url": "git+https://github.com/frenic/csstype.git"
+      },
+      "author": { "name": "Fredrik Nicol", "email": "fredrik.nicol@gmail.com" },
+      "license": "MIT",
+      "devDependencies": {
+        "@types/chokidar": "^2.1.3",
+        "@types/css-tree": "^2.3.1",
+        "@types/jest": "^29.5.0",
+        "@types/jsdom": "^21.1.1",
+        "@types/node": "^16.18.23",
+        "@types/prettier": "^2.7.2",
+        "@types/request": "^2.48.8",
+        "@types/turndown": "^5.0.1",
+        "@typescript-eslint/eslint-plugin": "^5.57.0",
+        "@typescript-eslint/parser": "^5.57.0",
+        "chalk": "^4.1.2",
+        "chokidar": "^3.5.3",
+        "eslint": "^8.37.0",
+        "css-tree": "^2.3.1",
+        "eslint-config-prettier": "^8.8.0",
+        "eslint-plugin-prettier": "^4.2.1",
+        "fast-glob": "^3.2.12",
+        "flow-bin": "^0.203.1",
+        "jest": "^29.5.0",
+        "jsdom": "^21.1.1",
+        "mdn-browser-compat-data": "git+https://github.com/mdn/browser-compat-data.git#1bf44517bd08de735e9ec20dbfe8e86c96341054",
+        "mdn-data": "git+https://github.com/mdn/data.git#7f0c865a3c4b5d891285c93308ee5c25cb5cfee8",
+        "prettier": "^2.8.7",
+        "request": "^2.88.2",
+        "ts-jest": "^29.0.5",
+        "ts-node": "^10.9.1",
+        "turndown": "^7.1.2",
+        "typescript": "~5.0.3"
+      },
+      "scripts": {
+        "prepublish": "npm install --prefix __tests__ && npm install --prefix __tests__/__fixtures__",
+        "prepublishOnly": "tsc && npm run test:src && npm run build && ts-node --files prepublish.ts",
+        "update": "ts-node --files update.ts",
+        "build": "ts-node --files build.ts --start",
+        "watch": "ts-node --files build.ts --watch",
+        "lint": "eslint . --ext .js,.jsx,.ts,.tsx --fix",
+        "pretty": "prettier --write build.ts **/*.{ts,js,json,md}",
+        "lazy": "tsc && npm run lint",
+        "test": "jest --runInBand",
+        "test:src": "jest src.*.ts",
+        "test:dist": "jest dist.*.ts --runInBand"
+      },
+      "gitHead": "fb448e21733ac5cb52523d3b678fdbbe1f9b42f2",
+      "bugs": { "url": "https://github.com/frenic/csstype/issues" },
+      "_id": "csstype@3.1.3",
+      "_nodeVersion": "18.16.0",
+      "_npmVersion": "9.5.1",
+      "dist": {
+        "integrity": "sha512-M1uQkMl8rQK/szD0LNhtqxIPLpimGm8sOBwU7lLnCpSbTyY3yeU1Vc7l4KT5zT4s/yOxHH5O7tIuuLOCnLADRw==",
+        "shasum": "d80ff294d114fb0e6ac500fbf85b60137d7eff81",
+        "tarball": "http://localhost:4260/csstype/csstype-3.1.3.tgz",
+        "fileCount": 5,
+        "unpackedSize": 1246074,
+        "signatures": [
+          {
+            "keyid": "SHA256:jl3bwswu80PjjokCgh0o2w5c2U4LhQAE57gj9cz1kzA",
+            "sig": "MEQCIF2zTnkc6R7cr7euidncjKp9gnQSpUmoKPzB/pvL4rsQAiB4E1mDQEtpvu9cjct0kaUbtTAQc+rBLAO65gAk+ykfig=="
+          }
+        ]
+      },
+      "directories": {},
+      "_hasShrinkwrap": false
     }
   },
   "author": {
diff --git a/tests/specs/add/alias/__test__.jsonc b/tests/specs/add/alias/__test__.jsonc
new file mode 100644
index 0000000000..8a16ad3b46
--- /dev/null
+++ b/tests/specs/add/alias/__test__.jsonc
@@ -0,0 +1,13 @@
+{
+  "tempDir": true,
+  "steps": [{
+    "args": "install my-alias@npm:@denotest/add",
+    "output": "[WILDCARD]"
+  }, {
+    "args": [
+      "eval",
+      "console.log(Deno.readTextFileSync('package.json').trim())"
+    ],
+    "output": "package.json.out"
+  }]
+}
diff --git a/tests/specs/add/alias/package.json b/tests/specs/add/alias/package.json
new file mode 100644
index 0000000000..9664f260a7
--- /dev/null
+++ b/tests/specs/add/alias/package.json
@@ -0,0 +1,4 @@
+{
+  "dependencies": {
+  }
+}
diff --git a/tests/specs/add/alias/package.json.out b/tests/specs/add/alias/package.json.out
new file mode 100644
index 0000000000..b6326e8bfb
--- /dev/null
+++ b/tests/specs/add/alias/package.json.out
@@ -0,0 +1,5 @@
+{
+  "dependencies": {
+    "my-alias": "npm:@denotest/add@^1.0.0"
+  }
+}
diff --git a/tests/specs/add/comments_deno_json/__test__.jsonc b/tests/specs/add/comments_deno_json/__test__.jsonc
new file mode 100644
index 0000000000..7197eb473f
--- /dev/null
+++ b/tests/specs/add/comments_deno_json/__test__.jsonc
@@ -0,0 +1,16 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "add npm:@denotest/esm-basic jsr:@denotest/add",
+      "output": "[WILDCARD]"
+    },
+    {
+      "args": [
+        "eval",
+        "console.log(Deno.readTextFileSync('deno.jsonc').trim())"
+      ],
+      "output": "deno.jsonc.out"
+    }
+  ]
+}
diff --git a/tests/specs/add/comments_deno_json/deno.jsonc b/tests/specs/add/comments_deno_json/deno.jsonc
new file mode 100644
index 0000000000..6a37b343d9
--- /dev/null
+++ b/tests/specs/add/comments_deno_json/deno.jsonc
@@ -0,0 +1,7 @@
+// Testing four space indents too
+// deno-fmt-ignore
+{
+    "imports": {
+        "@denotest/add2": "npm:@denotest/add" // some comment
+    }
+}
diff --git a/tests/specs/add/comments_deno_json/deno.jsonc.out b/tests/specs/add/comments_deno_json/deno.jsonc.out
new file mode 100644
index 0000000000..0cca35c64c
--- /dev/null
+++ b/tests/specs/add/comments_deno_json/deno.jsonc.out
@@ -0,0 +1,9 @@
+// Testing four space indents too
+// deno-fmt-ignore
+{
+    "imports": {
+        "@denotest/add": "jsr:@denotest/add@^1.0.0",
+        "@denotest/add2": "npm:@denotest/add", // some comment
+        "@denotest/esm-basic": "npm:@denotest/esm-basic@^1.0.0"
+    }
+}
diff --git a/tests/specs/add/dev/add.out b/tests/specs/add/dev/add.out
index 42161f3ae1..44bd9cac7e 100644
--- a/tests/specs/add/dev/add.out
+++ b/tests/specs/add/dev/add.out
@@ -1,4 +1,4 @@
 Add npm:@denotest/esm-basic@1.0.0
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/add/exact_version/__test__.jsonc b/tests/specs/add/exact_version/__test__.jsonc
new file mode 100644
index 0000000000..feb6cc6172
--- /dev/null
+++ b/tests/specs/add/exact_version/__test__.jsonc
@@ -0,0 +1,35 @@
+{
+  "tempDir": true,
+  "tests": {
+    "npm": {
+      "steps": [
+        {
+          "args": "add npm:@denotest/esm-basic@1.0.0",
+          "output": "npm_add.out"
+        },
+        {
+          "args": [
+            "eval",
+            "console.log(Deno.readTextFileSync('deno.json').trim())"
+          ],
+          "output": "npm_deno.json.out"
+        }
+      ]
+    },
+    "jsr": {
+      "steps": [
+        {
+          "args": "add jsr:@denotest/add@1.0.0",
+          "output": "jsr_add.out"
+        },
+        {
+          "args": [
+            "eval",
+            "console.log(Deno.readTextFileSync('deno.json').trim())"
+          ],
+          "output": "jsr_deno.json.out"
+        }
+      ]
+    }
+  }
+}
diff --git a/tests/node_compat/test/common/package.json b/tests/specs/add/exact_version/deno.json
similarity index 100%
rename from tests/node_compat/test/common/package.json
rename to tests/specs/add/exact_version/deno.json
diff --git a/tests/specs/add/exact_version/jsr_add.out b/tests/specs/add/exact_version/jsr_add.out
new file mode 100644
index 0000000000..f2684ef57e
--- /dev/null
+++ b/tests/specs/add/exact_version/jsr_add.out
@@ -0,0 +1,2 @@
+Add jsr:@denotest/add@1.0.0
+Download http://127.0.0.1:4250/@denotest/add/1.0.0/mod.ts
diff --git a/tests/specs/add/exact_version/jsr_deno.json.out b/tests/specs/add/exact_version/jsr_deno.json.out
new file mode 100644
index 0000000000..7f1715bd78
--- /dev/null
+++ b/tests/specs/add/exact_version/jsr_deno.json.out
@@ -0,0 +1,5 @@
+{
+  "imports": {
+    "@denotest/add": "jsr:@denotest/add@1.0.0"
+  }
+}
diff --git a/tests/specs/add/exact_version/npm_add.out b/tests/specs/add/exact_version/npm_add.out
new file mode 100644
index 0000000000..2f73e5afb5
--- /dev/null
+++ b/tests/specs/add/exact_version/npm_add.out
@@ -0,0 +1,3 @@
+Add npm:@denotest/esm-basic@1.0.0
+Download http://localhost:4260/@denotest%2fesm-basic
+Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
diff --git a/tests/specs/add/exact_version/npm_deno.json.out b/tests/specs/add/exact_version/npm_deno.json.out
new file mode 100644
index 0000000000..ff4afa772b
--- /dev/null
+++ b/tests/specs/add/exact_version/npm_deno.json.out
@@ -0,0 +1,5 @@
+{
+  "imports": {
+    "@denotest/esm-basic": "npm:@denotest/esm-basic@1.0.0"
+  }
+}
diff --git a/tests/specs/add/existing_deps_singleline/__test__.jsonc b/tests/specs/add/existing_deps_singleline/__test__.jsonc
new file mode 100644
index 0000000000..8a6ef1a5fa
--- /dev/null
+++ b/tests/specs/add/existing_deps_singleline/__test__.jsonc
@@ -0,0 +1,16 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "add npm:@denotest/esm-basic",
+      "output": "[WILDCARD]"
+    },
+    {
+      "args": [
+        "eval",
+        "console.log(Deno.readTextFileSync('package.json').trim())"
+      ],
+      "output": "package.json.out"
+    }
+  ]
+}
diff --git a/tests/specs/add/existing_deps_singleline/package.json b/tests/specs/add/existing_deps_singleline/package.json
new file mode 100644
index 0000000000..3677a6e2e8
--- /dev/null
+++ b/tests/specs/add/existing_deps_singleline/package.json
@@ -0,0 +1,3 @@
+{
+  "dependencies": { "cowsay": "*" }
+}
diff --git a/tests/specs/add/existing_deps_singleline/package.json.out b/tests/specs/add/existing_deps_singleline/package.json.out
new file mode 100644
index 0000000000..5a7fa36805
--- /dev/null
+++ b/tests/specs/add/existing_deps_singleline/package.json.out
@@ -0,0 +1,6 @@
+{
+  "dependencies": {
+    "@denotest/esm-basic": "^1.0.0",
+    "cowsay": "*"
+  }
+}
diff --git a/tests/specs/add/exiting_dev_deps/__test__.jsonc b/tests/specs/add/exiting_dev_deps/__test__.jsonc
new file mode 100644
index 0000000000..8a6ef1a5fa
--- /dev/null
+++ b/tests/specs/add/exiting_dev_deps/__test__.jsonc
@@ -0,0 +1,16 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "add npm:@denotest/esm-basic",
+      "output": "[WILDCARD]"
+    },
+    {
+      "args": [
+        "eval",
+        "console.log(Deno.readTextFileSync('package.json').trim())"
+      ],
+      "output": "package.json.out"
+    }
+  ]
+}
diff --git a/tests/specs/add/exiting_dev_deps/package.json b/tests/specs/add/exiting_dev_deps/package.json
new file mode 100644
index 0000000000..e7b8c50618
--- /dev/null
+++ b/tests/specs/add/exiting_dev_deps/package.json
@@ -0,0 +1,5 @@
+{
+  "devDependencies": {
+    "cowsay": "*"
+  }
+}
diff --git a/tests/specs/add/exiting_dev_deps/package.json.out b/tests/specs/add/exiting_dev_deps/package.json.out
new file mode 100644
index 0000000000..9bff99bc28
--- /dev/null
+++ b/tests/specs/add/exiting_dev_deps/package.json.out
@@ -0,0 +1,8 @@
+{
+  "dependencies": {
+    "@denotest/esm-basic": "^1.0.0"
+  },
+  "devDependencies": {
+    "cowsay": "*"
+  }
+}
diff --git a/tests/specs/add/jsr_prefers_deno_json/__test__.jsonc b/tests/specs/add/jsr_prefers_deno_json/__test__.jsonc
new file mode 100644
index 0000000000..ca9c4b4d9d
--- /dev/null
+++ b/tests/specs/add/jsr_prefers_deno_json/__test__.jsonc
@@ -0,0 +1,16 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "add jsr:@denotest/add",
+      "output": "add.out"
+    },
+    {
+      "args": [
+        "eval",
+        "console.log(Deno.readTextFileSync('./deno.json').trim())"
+      ],
+      "output": "deno.json.out"
+    }
+  ]
+}
diff --git a/tests/specs/add/jsr_prefers_deno_json/add.out b/tests/specs/add/jsr_prefers_deno_json/add.out
new file mode 100644
index 0000000000..cb8140c6db
--- /dev/null
+++ b/tests/specs/add/jsr_prefers_deno_json/add.out
@@ -0,0 +1,3 @@
+Created deno.json configuration file.
+Add jsr:@denotest/add@1.0.0
+Download [WILDCARD]
diff --git a/tests/specs/add/jsr_prefers_deno_json/deno.json.out b/tests/specs/add/jsr_prefers_deno_json/deno.json.out
new file mode 100644
index 0000000000..38ca2d4b85
--- /dev/null
+++ b/tests/specs/add/jsr_prefers_deno_json/deno.json.out
@@ -0,0 +1,5 @@
+{
+  "imports": {
+    "@denotest/add": "jsr:@denotest/add@^1.0.0"
+  }
+}
diff --git a/tests/node_compat/test/fixtures/package.json b/tests/specs/add/jsr_prefers_deno_json/package.json
similarity index 100%
rename from tests/node_compat/test/fixtures/package.json
rename to tests/specs/add/jsr_prefers_deno_json/package.json
diff --git a/tests/specs/add/only_unstable_versions/__test__.jsonc b/tests/specs/add/only_unstable_versions/__test__.jsonc
index d05628b6f5..ea5a270b9c 100644
--- a/tests/specs/add/only_unstable_versions/__test__.jsonc
+++ b/tests/specs/add/only_unstable_versions/__test__.jsonc
@@ -1,9 +1,22 @@
 {
   "tempDir": true,
-  "steps": [
-    {
-      "args": "add npm:@denotest/unstable",
-      "output": "add.out"
+  "tests": {
+    "npm_package": {
+      "steps": [
+        {
+          "args": "add npm:@denotest/unstable",
+          "output": "add.out"
+        }
+      ]
+    },
+    "jsr_package": {
+      "steps": [
+        {
+          "args": "add jsr:@denotest/unstable",
+          "output": "add_jsr.out",
+          "exitCode": 1
+        }
+      ]
     }
-  ]
+  }
 }
diff --git a/tests/specs/add/only_unstable_versions/add.out b/tests/specs/add/only_unstable_versions/add.out
index 48462b8bea..8bd8d93038 100644
--- a/tests/specs/add/only_unstable_versions/add.out
+++ b/tests/specs/add/only_unstable_versions/add.out
@@ -1,3 +1,3 @@
 Add npm:@denotest/unstable@1.0.0-beta.1
-Download http://localhost:4260/@denotest/unstable
+Download http://localhost:4260/@denotest%2funstable
 Download http://localhost:4260/@denotest/unstable/1.0.0-beta.1.tgz
diff --git a/tests/specs/add/only_unstable_versions/add_jsr.out b/tests/specs/add/only_unstable_versions/add_jsr.out
new file mode 100644
index 0000000000..95f0630bf3
--- /dev/null
+++ b/tests/specs/add/only_unstable_versions/add_jsr.out
@@ -0,0 +1 @@
+error: jsr:@denotest/unstable has only pre-release versions available. Try specifying a version: `deno add jsr:@denotest/unstable@^1.0.0-beta.2`
diff --git a/tests/specs/add/package_json_and_deno_json/__test__.jsonc b/tests/specs/add/package_json_and_deno_json/__test__.jsonc
index 0beee02d15..8d67a07c82 100644
--- a/tests/specs/add/package_json_and_deno_json/__test__.jsonc
+++ b/tests/specs/add/package_json_and_deno_json/__test__.jsonc
@@ -41,6 +41,29 @@
           "output": "good\n"
         }
       ]
+    },
+    "only_prefers_package_json_if_closer": {
+      "steps": [
+        {
+          "cwd": "./subdir",
+          "args": "add npm:@denotest/esm-basic jsr:@denotest/add npm:@denotest/say-hello",
+          "output": "[WILDCARD]"
+        },
+        {
+          "args": [
+            "eval",
+            "console.log(Deno.readTextFileSync('package.json').trim())"
+          ],
+          "output": "{}\n"
+        },
+        {
+          "args": [
+            "eval",
+            "console.log(Deno.readTextFileSync('./subdir/deno.json').trim())"
+          ],
+          "output": "subdir/prefer_if_closer_deno.json.out"
+        }
+      ]
     }
   }
 }
diff --git a/tests/specs/add/package_json_and_deno_json/add.out b/tests/specs/add/package_json_and_deno_json/add.out
index 5577a55acc..4ce7bb8ee1 100644
--- a/tests/specs/add/package_json_and_deno_json/add.out
+++ b/tests/specs/add/package_json_and_deno_json/add.out
@@ -2,9 +2,9 @@
 Add npm:@denotest/esm-basic@1.0.0
 Add jsr:@denotest/add@1.0.0
 Add npm:@denotest/say-hello@1.0.0
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
-Download http://localhost:4260/@denotest/say-hello
+Download http://localhost:4260/@denotest%2fsay-hello
 Download http://localhost:4260/@denotest/say-hello/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 Initialize @denotest/say-hello@1.0.0
diff --git a/tests/specs/add/package_json_and_deno_json/add_esm_basic.out b/tests/specs/add/package_json_and_deno_json/add_esm_basic.out
index 42161f3ae1..44bd9cac7e 100644
--- a/tests/specs/add/package_json_and_deno_json/add_esm_basic.out
+++ b/tests/specs/add/package_json_and_deno_json/add_esm_basic.out
@@ -1,4 +1,4 @@
 Add npm:@denotest/esm-basic@1.0.0
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/add/package_json_and_deno_json/subdir/deno.json b/tests/specs/add/package_json_and_deno_json/subdir/deno.json
new file mode 100644
index 0000000000..cc54bbd8a2
--- /dev/null
+++ b/tests/specs/add/package_json_and_deno_json/subdir/deno.json
@@ -0,0 +1,4 @@
+{
+  "name": "@test/subdir",
+  "exports": "./mod.ts"
+}
diff --git a/tests/specs/run/allow_run_insecure_warnings/main.ts b/tests/specs/add/package_json_and_deno_json/subdir/mod.ts
similarity index 100%
rename from tests/specs/run/allow_run_insecure_warnings/main.ts
rename to tests/specs/add/package_json_and_deno_json/subdir/mod.ts
diff --git a/tests/specs/add/package_json_and_deno_json/subdir/prefer_if_closer_deno.json.out b/tests/specs/add/package_json_and_deno_json/subdir/prefer_if_closer_deno.json.out
new file mode 100644
index 0000000000..8a5819d503
--- /dev/null
+++ b/tests/specs/add/package_json_and_deno_json/subdir/prefer_if_closer_deno.json.out
@@ -0,0 +1,9 @@
+{
+  "name": "@test/subdir",
+  "exports": "./mod.ts",
+  "imports": {
+    "@denotest/add": "jsr:@denotest/add@^1.0.0",
+    "@denotest/esm-basic": "npm:@denotest/esm-basic@^1.0.0",
+    "@denotest/say-hello": "npm:@denotest/say-hello@^1.0.0"
+  }
+}
diff --git a/tests/specs/add/update_lockfile_if_package_json/__test__.jsonc b/tests/specs/add/update_lockfile_if_package_json/__test__.jsonc
new file mode 100644
index 0000000000..80b35dc3c2
--- /dev/null
+++ b/tests/specs/add/update_lockfile_if_package_json/__test__.jsonc
@@ -0,0 +1,31 @@
+{
+  "tempDir": true,
+  "tests": {
+    "updates_lockfile": {
+      "steps": [
+        {
+          "args": "add npm:@denotest/esm-basic npm:@denotest/say-hello",
+          "output": "add.out"
+        },
+        {
+          "args": [
+            "eval",
+            "console.log(Deno.readTextFileSync('deno.lock'))"
+          ],
+          "output": "lockfile_add.out"
+        },
+        {
+          "args": "remove @denotest/esm-basic @denotest/say-hello",
+          "output": "remove.out"
+        },
+        {
+          "args": [
+            "eval",
+            "console.log(Deno.readTextFileSync('deno.lock'))"
+          ],
+          "output": "lockfile_remove.out"
+        }
+      ]
+    }
+  }
+}
diff --git a/tests/specs/add/update_lockfile_if_package_json/add.out b/tests/specs/add/update_lockfile_if_package_json/add.out
new file mode 100644
index 0000000000..97989b0c38
--- /dev/null
+++ b/tests/specs/add/update_lockfile_if_package_json/add.out
@@ -0,0 +1,5 @@
+[UNORDERED_START]
+Add npm:@denotest/esm-basic@1.0.0
+Add npm:@denotest/say-hello@1.0.0
+[UNORDERED_END]
+[WILDCARD]
\ No newline at end of file
diff --git a/tests/specs/add/update_lockfile_if_package_json/lockfile_add.out b/tests/specs/add/update_lockfile_if_package_json/lockfile_add.out
new file mode 100644
index 0000000000..d452c2de82
--- /dev/null
+++ b/tests/specs/add/update_lockfile_if_package_json/lockfile_add.out
@@ -0,0 +1,7 @@
+{
+  "version": "4",
+  "specifiers": {
+    "npm:@denotest/esm-basic@1": "1.0.0",
+    "npm:@denotest/say-hello@1": "1.0.0"
+  },
+[WILDCARD]
diff --git a/tests/specs/add/update_lockfile_if_package_json/lockfile_remove.out b/tests/specs/add/update_lockfile_if_package_json/lockfile_remove.out
new file mode 100644
index 0000000000..fdd4f1cc60
--- /dev/null
+++ b/tests/specs/add/update_lockfile_if_package_json/lockfile_remove.out
@@ -0,0 +1,4 @@
+{
+  "version": "4"
+}
+
diff --git a/tests/testdata/run/check_js_points_to_ts/foo.d.ts b/tests/specs/add/update_lockfile_if_package_json/package.json
similarity index 100%
rename from tests/testdata/run/check_js_points_to_ts/foo.d.ts
rename to tests/specs/add/update_lockfile_if_package_json/package.json
diff --git a/tests/specs/add/update_lockfile_if_package_json/remove.out b/tests/specs/add/update_lockfile_if_package_json/remove.out
new file mode 100644
index 0000000000..8efb0810cf
--- /dev/null
+++ b/tests/specs/add/update_lockfile_if_package_json/remove.out
@@ -0,0 +1,4 @@
+[UNORDERED_START]
+Removed @denotest/esm-basic
+Removed @denotest/say-hello
+[UNORDERED_END]
diff --git a/tests/specs/bench/package_json/install.out b/tests/specs/bench/package_json/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/bench/package_json/install.out
+++ b/tests/specs/bench/package_json/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/cache/package_json/main.cache.out b/tests/specs/cache/package_json/main.cache.out
index f5a1cd15ee..af6bcb03b3 100644
--- a/tests/specs/cache/package_json/main.cache.out
+++ b/tests/specs/cache/package_json/main.cache.out
@@ -1,2 +1,2 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
diff --git a/tests/specs/check/check_broadcast_channel/__test__.jsonc b/tests/specs/check/check_broadcast_channel/__test__.jsonc
new file mode 100644
index 0000000000..6190781a5c
--- /dev/null
+++ b/tests/specs/check/check_broadcast_channel/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "check --quiet broadcast_channel.ts",
+  "output": "",
+  "exitCode": 0
+}
diff --git a/tests/testdata/check/broadcast_channel.ts b/tests/specs/check/check_broadcast_channel/broadcast_channel.ts
similarity index 100%
rename from tests/testdata/check/broadcast_channel.ts
rename to tests/specs/check/check_broadcast_channel/broadcast_channel.ts
diff --git a/tests/specs/check/check_deno_not_found/__test__.jsonc b/tests/specs/check/check_deno_not_found/__test__.jsonc
new file mode 100644
index 0000000000..cbc6552b35
--- /dev/null
+++ b/tests/specs/check/check_deno_not_found/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "check --quiet deno_not_found/main.ts",
+  "output": "deno_not_found/main.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/check/deno_not_found/main.out b/tests/specs/check/check_deno_not_found/deno_not_found/main.out
similarity index 82%
rename from tests/testdata/check/deno_not_found/main.out
rename to tests/specs/check/check_deno_not_found/deno_not_found/main.out
index dc4a682c75..2b6f44d1e2 100644
--- a/tests/testdata/check/deno_not_found/main.out
+++ b/tests/specs/check/check_deno_not_found/deno_not_found/main.out
@@ -1,4 +1,4 @@
 error: TS2304 [ERROR]: Cannot find name 'Deno'. Do you need to change your target library? Try changing the 'lib' compiler option to include 'deno.ns' or add a triple-slash directive to the top of your entrypoint (main file): /// <reference lib="deno.ns" />
 Deno;
 ~~~~
-    at file:///[WILDCARD]/check/deno_not_found/main.ts:4:1
+    at file:///[WILDCARD]/deno_not_found/main.ts:4:1
diff --git a/tests/testdata/check/deno_not_found/main.ts b/tests/specs/check/check_deno_not_found/deno_not_found/main.ts
similarity index 100%
rename from tests/testdata/check/deno_not_found/main.ts
rename to tests/specs/check/check_deno_not_found/deno_not_found/main.ts
diff --git a/tests/specs/check/check_dts/__test__.jsonc b/tests/specs/check/check_dts/__test__.jsonc
new file mode 100644
index 0000000000..d684e20634
--- /dev/null
+++ b/tests/specs/check/check_dts/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "check --quiet dts/check_dts.d.ts",
+  "output": "dts/check_dts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/check/dts/check_dts.d.ts b/tests/specs/check/check_dts/dts/check_dts.d.ts
similarity index 100%
rename from tests/testdata/check/dts/check_dts.d.ts
rename to tests/specs/check/check_dts/dts/check_dts.d.ts
diff --git a/tests/testdata/check/dts/check_dts.out b/tests/specs/check/check_dts/dts/check_dts.out
similarity index 100%
rename from tests/testdata/check/dts/check_dts.out
rename to tests/specs/check/check_dts/dts/check_dts.out
diff --git a/tests/specs/check/check_imported_files_listed_in_exclude_option/__test__.jsonc b/tests/specs/check/check_imported_files_listed_in_exclude_option/__test__.jsonc
new file mode 100644
index 0000000000..1fd2d87602
--- /dev/null
+++ b/tests/specs/check/check_imported_files_listed_in_exclude_option/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "check --quiet --config exclude_option/deno.exclude_dir.json exclude_option/index.ts",
+  "output": "exclude_option/exclude_option.ts.error.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/check/exclude_option/deno.exclude_dir.json b/tests/specs/check/check_imported_files_listed_in_exclude_option/exclude_option/deno.exclude_dir.json
similarity index 100%
rename from tests/testdata/check/exclude_option/deno.exclude_dir.json
rename to tests/specs/check/check_imported_files_listed_in_exclude_option/exclude_option/deno.exclude_dir.json
diff --git a/tests/testdata/check/exclude_option/deno.exclude_glob.json b/tests/specs/check/check_imported_files_listed_in_exclude_option/exclude_option/deno.exclude_glob.json
similarity index 100%
rename from tests/testdata/check/exclude_option/deno.exclude_glob.json
rename to tests/specs/check/check_imported_files_listed_in_exclude_option/exclude_option/deno.exclude_glob.json
diff --git a/tests/testdata/check/exclude_option/deno.json b/tests/specs/check/check_imported_files_listed_in_exclude_option/exclude_option/deno.json
similarity index 100%
rename from tests/testdata/check/exclude_option/deno.json
rename to tests/specs/check/check_imported_files_listed_in_exclude_option/exclude_option/deno.json
diff --git a/tests/testdata/check/exclude_option/exclude_option.ts.error.out b/tests/specs/check/check_imported_files_listed_in_exclude_option/exclude_option/exclude_option.ts.error.out
similarity index 100%
rename from tests/testdata/check/exclude_option/exclude_option.ts.error.out
rename to tests/specs/check/check_imported_files_listed_in_exclude_option/exclude_option/exclude_option.ts.error.out
diff --git a/tests/testdata/check/exclude_option/ignored/index.ts b/tests/specs/check/check_imported_files_listed_in_exclude_option/exclude_option/ignored/index.ts
similarity index 100%
rename from tests/testdata/check/exclude_option/ignored/index.ts
rename to tests/specs/check/check_imported_files_listed_in_exclude_option/exclude_option/ignored/index.ts
diff --git a/tests/testdata/check/exclude_option/index.ts b/tests/specs/check/check_imported_files_listed_in_exclude_option/exclude_option/index.ts
similarity index 100%
rename from tests/testdata/check/exclude_option/index.ts
rename to tests/specs/check/check_imported_files_listed_in_exclude_option/exclude_option/index.ts
diff --git a/tests/specs/check/check_jsximportsource_importmap_config/__test__.jsonc b/tests/specs/check/check_jsximportsource_importmap_config/__test__.jsonc
new file mode 100644
index 0000000000..bbe32ca9e7
--- /dev/null
+++ b/tests/specs/check/check_jsximportsource_importmap_config/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "check --quiet --config jsximportsource_importmap_config/deno.json jsximportsource_importmap_config/main.tsx",
+  "output": ""
+}
diff --git a/tests/testdata/check/jsximportsource_importmap_config/deno.json b/tests/specs/check/check_jsximportsource_importmap_config/jsximportsource_importmap_config/deno.json
similarity index 100%
rename from tests/testdata/check/jsximportsource_importmap_config/deno.json
rename to tests/specs/check/check_jsximportsource_importmap_config/jsximportsource_importmap_config/deno.json
diff --git a/tests/testdata/check/jsximportsource_importmap_config/import_map.json b/tests/specs/check/check_jsximportsource_importmap_config/jsximportsource_importmap_config/import_map.json
similarity index 100%
rename from tests/testdata/check/jsximportsource_importmap_config/import_map.json
rename to tests/specs/check/check_jsximportsource_importmap_config/jsximportsource_importmap_config/import_map.json
diff --git a/tests/testdata/check/jsximportsource_importmap_config/jsx_runtime.ts b/tests/specs/check/check_jsximportsource_importmap_config/jsximportsource_importmap_config/jsx_runtime.ts
similarity index 100%
rename from tests/testdata/check/jsximportsource_importmap_config/jsx_runtime.ts
rename to tests/specs/check/check_jsximportsource_importmap_config/jsximportsource_importmap_config/jsx_runtime.ts
diff --git a/tests/testdata/check/jsximportsource_importmap_config/main.tsx b/tests/specs/check/check_jsximportsource_importmap_config/jsximportsource_importmap_config/main.tsx
similarity index 100%
rename from tests/testdata/check/jsximportsource_importmap_config/main.tsx
rename to tests/specs/check/check_jsximportsource_importmap_config/jsximportsource_importmap_config/main.tsx
diff --git a/tests/specs/check/check_no_error_truncation/__test__.jsonc b/tests/specs/check/check_no_error_truncation/__test__.jsonc
new file mode 100644
index 0000000000..15884059c6
--- /dev/null
+++ b/tests/specs/check/check_no_error_truncation/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "check --quiet no_error_truncation/main.ts --config no_error_truncation/deno.json",
+  "output": "no_error_truncation/main.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/check/no_error_truncation/deno.json b/tests/specs/check/check_no_error_truncation/no_error_truncation/deno.json
similarity index 100%
rename from tests/testdata/check/no_error_truncation/deno.json
rename to tests/specs/check/check_no_error_truncation/no_error_truncation/deno.json
diff --git a/tests/testdata/check/no_error_truncation/main.out b/tests/specs/check/check_no_error_truncation/no_error_truncation/main.out
similarity index 100%
rename from tests/testdata/check/no_error_truncation/main.out
rename to tests/specs/check/check_no_error_truncation/no_error_truncation/main.out
diff --git a/tests/testdata/check/no_error_truncation/main.ts b/tests/specs/check/check_no_error_truncation/no_error_truncation/main.ts
similarity index 100%
rename from tests/testdata/check/no_error_truncation/main.ts
rename to tests/specs/check/check_no_error_truncation/no_error_truncation/main.ts
diff --git a/tests/specs/check/check_node_builtin_modules_js/__test__.jsonc b/tests/specs/check/check_node_builtin_modules_js/__test__.jsonc
new file mode 100644
index 0000000000..8f7a2a65a6
--- /dev/null
+++ b/tests/specs/check/check_node_builtin_modules_js/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "check --quiet node_builtin_modules/mod.js",
+  "output": "node_builtin_modules/mod.js.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/check/node_builtin_modules/mod.js b/tests/specs/check/check_node_builtin_modules_js/node_builtin_modules/mod.js
similarity index 100%
rename from tests/testdata/check/node_builtin_modules/mod.js
rename to tests/specs/check/check_node_builtin_modules_js/node_builtin_modules/mod.js
diff --git a/tests/testdata/check/node_builtin_modules/mod.js.out b/tests/specs/check/check_node_builtin_modules_js/node_builtin_modules/mod.js.out
similarity index 100%
rename from tests/testdata/check/node_builtin_modules/mod.js.out
rename to tests/specs/check/check_node_builtin_modules_js/node_builtin_modules/mod.js.out
diff --git a/tests/testdata/check/node_builtin_modules/mod.ts b/tests/specs/check/check_node_builtin_modules_js/node_builtin_modules/mod.ts
similarity index 100%
rename from tests/testdata/check/node_builtin_modules/mod.ts
rename to tests/specs/check/check_node_builtin_modules_js/node_builtin_modules/mod.ts
diff --git a/tests/testdata/check/node_builtin_modules/mod.ts.out b/tests/specs/check/check_node_builtin_modules_js/node_builtin_modules/mod.ts.out
similarity index 100%
rename from tests/testdata/check/node_builtin_modules/mod.ts.out
rename to tests/specs/check/check_node_builtin_modules_js/node_builtin_modules/mod.ts.out
diff --git a/tests/specs/check/check_node_builtin_modules_ts/__test__.jsonc b/tests/specs/check/check_node_builtin_modules_ts/__test__.jsonc
new file mode 100644
index 0000000000..736885f2ec
--- /dev/null
+++ b/tests/specs/check/check_node_builtin_modules_ts/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "check --quiet node_builtin_modules/mod.ts",
+  "output": "node_builtin_modules/mod.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/check/check_node_builtin_modules_ts/node_builtin_modules/mod.js b/tests/specs/check/check_node_builtin_modules_ts/node_builtin_modules/mod.js
new file mode 100644
index 0000000000..196fb9be98
--- /dev/null
+++ b/tests/specs/check/check_node_builtin_modules_ts/node_builtin_modules/mod.js
@@ -0,0 +1,3 @@
+// @ts-check
+import fs from "node:fs";
+const _data = fs.readFileSync("./node_builtin.js", 123);
diff --git a/tests/specs/check/check_node_builtin_modules_ts/node_builtin_modules/mod.js.out b/tests/specs/check/check_node_builtin_modules_ts/node_builtin_modules/mod.js.out
new file mode 100644
index 0000000000..97786ebaeb
--- /dev/null
+++ b/tests/specs/check/check_node_builtin_modules_ts/node_builtin_modules/mod.js.out
@@ -0,0 +1,5 @@
+error: TS2769 [ERROR]: No overload matches this call.
+  [WILDCARD]
+const _data = fs.readFileSync("./node_builtin.js", 123);
+                                                   ~~~
+    at file:///[WILDCARD]/node_builtin_modules/mod.js:3:52
diff --git a/tests/specs/check/check_node_builtin_modules_ts/node_builtin_modules/mod.ts b/tests/specs/check/check_node_builtin_modules_ts/node_builtin_modules/mod.ts
new file mode 100644
index 0000000000..0e62353fec
--- /dev/null
+++ b/tests/specs/check/check_node_builtin_modules_ts/node_builtin_modules/mod.ts
@@ -0,0 +1,9 @@
+import fs from "node:fs";
+const _data = fs.readFileSync("./node_builtin.js", 123);
+
+// check node:module specifically because for deno check it should
+// resolve to the @types/node package, but at runtime it uses a different
+// builtin object than deno_std
+import { builtinModules } from "node:module";
+// should error about being string[]
+const _testString: number[] = builtinModules;
diff --git a/tests/specs/check/check_node_builtin_modules_ts/node_builtin_modules/mod.ts.out b/tests/specs/check/check_node_builtin_modules_ts/node_builtin_modules/mod.ts.out
new file mode 100644
index 0000000000..49b762cff8
--- /dev/null
+++ b/tests/specs/check/check_node_builtin_modules_ts/node_builtin_modules/mod.ts.out
@@ -0,0 +1,13 @@
+error: TS2769 [ERROR]: No overload matches this call.
+  [WILDCARD]
+const _data = fs.readFileSync("./node_builtin.js", 123);
+                                                   ~~~
+    at file:///[WILDCARD]/node_builtin_modules/mod.ts:2:52
+
+TS2322 [ERROR]: Type 'string[]' is not assignable to type 'number[]'.
+  Type 'string' is not assignable to type 'number'.
+const _testString: number[] = builtinModules;
+      ~~~~~~~~~~~
+    at file:///[WILDCARD]/node_builtin_modules/mod.ts:9:7
+
+Found 2 errors.
diff --git a/tests/specs/check/check_npm_install_diagnostics/__test__.jsonc b/tests/specs/check/check_npm_install_diagnostics/__test__.jsonc
new file mode 100644
index 0000000000..18260d362f
--- /dev/null
+++ b/tests/specs/check/check_npm_install_diagnostics/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "check --quiet npm_install_diagnostics/main.ts",
+  "output": "npm_install_diagnostics/main.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/check/npm_install_diagnostics/main.out b/tests/specs/check/check_npm_install_diagnostics/npm_install_diagnostics/main.out
similarity index 100%
rename from tests/testdata/check/npm_install_diagnostics/main.out
rename to tests/specs/check/check_npm_install_diagnostics/npm_install_diagnostics/main.out
diff --git a/tests/testdata/check/npm_install_diagnostics/main.ts b/tests/specs/check/check_npm_install_diagnostics/npm_install_diagnostics/main.ts
similarity index 100%
rename from tests/testdata/check/npm_install_diagnostics/main.ts
rename to tests/specs/check/check_npm_install_diagnostics/npm_install_diagnostics/main.ts
diff --git a/tests/specs/check/check_static_response_json/__test__.jsonc b/tests/specs/check/check_static_response_json/__test__.jsonc
new file mode 100644
index 0000000000..d286d3aa80
--- /dev/null
+++ b/tests/specs/check/check_static_response_json/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "check --quiet response_json.ts",
+  "output": "",
+  "exitCode": 0
+}
diff --git a/tests/testdata/check/response_json.ts b/tests/specs/check/check_static_response_json/response_json.ts
similarity index 100%
rename from tests/testdata/check/response_json.ts
rename to tests/specs/check/check_static_response_json/response_json.ts
diff --git a/tests/specs/check/check_with_exclude_option_by_dir/__test__.jsonc b/tests/specs/check/check_with_exclude_option_by_dir/__test__.jsonc
new file mode 100644
index 0000000000..c7fe285da8
--- /dev/null
+++ b/tests/specs/check/check_with_exclude_option_by_dir/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "check --quiet --config exclude_option/deno.exclude_dir.json exclude_option/ignored/index.ts",
+  "output": "",
+  "exitCode": 0
+}
diff --git a/tests/specs/check/check_with_exclude_option_by_dir/exclude_option/deno.exclude_dir.json b/tests/specs/check/check_with_exclude_option_by_dir/exclude_option/deno.exclude_dir.json
new file mode 100644
index 0000000000..2019f8953d
--- /dev/null
+++ b/tests/specs/check/check_with_exclude_option_by_dir/exclude_option/deno.exclude_dir.json
@@ -0,0 +1,5 @@
+{
+  "exclude": [
+    "ignored"
+  ]
+}
diff --git a/tests/specs/check/check_with_exclude_option_by_dir/exclude_option/deno.exclude_glob.json b/tests/specs/check/check_with_exclude_option_by_dir/exclude_option/deno.exclude_glob.json
new file mode 100644
index 0000000000..1d203ba089
--- /dev/null
+++ b/tests/specs/check/check_with_exclude_option_by_dir/exclude_option/deno.exclude_glob.json
@@ -0,0 +1,5 @@
+{
+  "exclude": [
+    "ignored/**/*"
+  ]
+}
diff --git a/tests/specs/check/check_with_exclude_option_by_dir/exclude_option/deno.json b/tests/specs/check/check_with_exclude_option_by_dir/exclude_option/deno.json
new file mode 100644
index 0000000000..a9eca74ca4
--- /dev/null
+++ b/tests/specs/check/check_with_exclude_option_by_dir/exclude_option/deno.json
@@ -0,0 +1,3 @@
+{
+  "exclude": []
+}
diff --git a/tests/specs/check/check_with_exclude_option_by_dir/exclude_option/exclude_option.ts.error.out b/tests/specs/check/check_with_exclude_option_by_dir/exclude_option/exclude_option.ts.error.out
new file mode 100644
index 0000000000..abd1c12586
--- /dev/null
+++ b/tests/specs/check/check_with_exclude_option_by_dir/exclude_option/exclude_option.ts.error.out
@@ -0,0 +1,4 @@
+error: TS2304 [ERROR]: Cannot find name 'nothing'.
+export { nothing };
+         ~~~~~~~
+    at [WILDCARD]
diff --git a/tests/specs/check/check_with_exclude_option_by_dir/exclude_option/ignored/index.ts b/tests/specs/check/check_with_exclude_option_by_dir/exclude_option/ignored/index.ts
new file mode 100644
index 0000000000..0419cf073c
--- /dev/null
+++ b/tests/specs/check/check_with_exclude_option_by_dir/exclude_option/ignored/index.ts
@@ -0,0 +1 @@
+export { nothing };
diff --git a/tests/specs/check/check_with_exclude_option_by_dir/exclude_option/index.ts b/tests/specs/check/check_with_exclude_option_by_dir/exclude_option/index.ts
new file mode 100644
index 0000000000..8335ca3a2e
--- /dev/null
+++ b/tests/specs/check/check_with_exclude_option_by_dir/exclude_option/index.ts
@@ -0,0 +1,5 @@
+import { nothing } from "./ignored/index.ts";
+
+const foo = 1;
+
+export { foo, nothing };
diff --git a/tests/specs/check/check_with_exclude_option_by_glob/__test__.jsonc b/tests/specs/check/check_with_exclude_option_by_glob/__test__.jsonc
new file mode 100644
index 0000000000..54700ca3d8
--- /dev/null
+++ b/tests/specs/check/check_with_exclude_option_by_glob/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "check --quiet --config exclude_option/deno.exclude_glob.json exclude_option/ignored/index.ts",
+  "output": "",
+  "exitCode": 0
+}
diff --git a/tests/specs/check/check_with_exclude_option_by_glob/exclude_option/deno.exclude_dir.json b/tests/specs/check/check_with_exclude_option_by_glob/exclude_option/deno.exclude_dir.json
new file mode 100644
index 0000000000..2019f8953d
--- /dev/null
+++ b/tests/specs/check/check_with_exclude_option_by_glob/exclude_option/deno.exclude_dir.json
@@ -0,0 +1,5 @@
+{
+  "exclude": [
+    "ignored"
+  ]
+}
diff --git a/tests/specs/check/check_with_exclude_option_by_glob/exclude_option/deno.exclude_glob.json b/tests/specs/check/check_with_exclude_option_by_glob/exclude_option/deno.exclude_glob.json
new file mode 100644
index 0000000000..1d203ba089
--- /dev/null
+++ b/tests/specs/check/check_with_exclude_option_by_glob/exclude_option/deno.exclude_glob.json
@@ -0,0 +1,5 @@
+{
+  "exclude": [
+    "ignored/**/*"
+  ]
+}
diff --git a/tests/specs/check/check_with_exclude_option_by_glob/exclude_option/deno.json b/tests/specs/check/check_with_exclude_option_by_glob/exclude_option/deno.json
new file mode 100644
index 0000000000..a9eca74ca4
--- /dev/null
+++ b/tests/specs/check/check_with_exclude_option_by_glob/exclude_option/deno.json
@@ -0,0 +1,3 @@
+{
+  "exclude": []
+}
diff --git a/tests/specs/check/check_with_exclude_option_by_glob/exclude_option/exclude_option.ts.error.out b/tests/specs/check/check_with_exclude_option_by_glob/exclude_option/exclude_option.ts.error.out
new file mode 100644
index 0000000000..abd1c12586
--- /dev/null
+++ b/tests/specs/check/check_with_exclude_option_by_glob/exclude_option/exclude_option.ts.error.out
@@ -0,0 +1,4 @@
+error: TS2304 [ERROR]: Cannot find name 'nothing'.
+export { nothing };
+         ~~~~~~~
+    at [WILDCARD]
diff --git a/tests/specs/check/check_with_exclude_option_by_glob/exclude_option/ignored/index.ts b/tests/specs/check/check_with_exclude_option_by_glob/exclude_option/ignored/index.ts
new file mode 100644
index 0000000000..0419cf073c
--- /dev/null
+++ b/tests/specs/check/check_with_exclude_option_by_glob/exclude_option/ignored/index.ts
@@ -0,0 +1 @@
+export { nothing };
diff --git a/tests/specs/check/check_with_exclude_option_by_glob/exclude_option/index.ts b/tests/specs/check/check_with_exclude_option_by_glob/exclude_option/index.ts
new file mode 100644
index 0000000000..8335ca3a2e
--- /dev/null
+++ b/tests/specs/check/check_with_exclude_option_by_glob/exclude_option/index.ts
@@ -0,0 +1,5 @@
+import { nothing } from "./ignored/index.ts";
+
+const foo = 1;
+
+export { foo, nothing };
diff --git a/tests/specs/check/check_without_exclude_option/__test__.jsonc b/tests/specs/check/check_without_exclude_option/__test__.jsonc
new file mode 100644
index 0000000000..801786fa3d
--- /dev/null
+++ b/tests/specs/check/check_without_exclude_option/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "check --quiet --config exclude_option/deno.json exclude_option/ignored/index.ts",
+  "output": "exclude_option/exclude_option.ts.error.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/check/check_without_exclude_option/exclude_option/deno.exclude_dir.json b/tests/specs/check/check_without_exclude_option/exclude_option/deno.exclude_dir.json
new file mode 100644
index 0000000000..2019f8953d
--- /dev/null
+++ b/tests/specs/check/check_without_exclude_option/exclude_option/deno.exclude_dir.json
@@ -0,0 +1,5 @@
+{
+  "exclude": [
+    "ignored"
+  ]
+}
diff --git a/tests/specs/check/check_without_exclude_option/exclude_option/deno.exclude_glob.json b/tests/specs/check/check_without_exclude_option/exclude_option/deno.exclude_glob.json
new file mode 100644
index 0000000000..1d203ba089
--- /dev/null
+++ b/tests/specs/check/check_without_exclude_option/exclude_option/deno.exclude_glob.json
@@ -0,0 +1,5 @@
+{
+  "exclude": [
+    "ignored/**/*"
+  ]
+}
diff --git a/tests/specs/check/check_without_exclude_option/exclude_option/deno.json b/tests/specs/check/check_without_exclude_option/exclude_option/deno.json
new file mode 100644
index 0000000000..a9eca74ca4
--- /dev/null
+++ b/tests/specs/check/check_without_exclude_option/exclude_option/deno.json
@@ -0,0 +1,3 @@
+{
+  "exclude": []
+}
diff --git a/tests/specs/check/check_without_exclude_option/exclude_option/exclude_option.ts.error.out b/tests/specs/check/check_without_exclude_option/exclude_option/exclude_option.ts.error.out
new file mode 100644
index 0000000000..abd1c12586
--- /dev/null
+++ b/tests/specs/check/check_without_exclude_option/exclude_option/exclude_option.ts.error.out
@@ -0,0 +1,4 @@
+error: TS2304 [ERROR]: Cannot find name 'nothing'.
+export { nothing };
+         ~~~~~~~
+    at [WILDCARD]
diff --git a/tests/specs/check/check_without_exclude_option/exclude_option/ignored/index.ts b/tests/specs/check/check_without_exclude_option/exclude_option/ignored/index.ts
new file mode 100644
index 0000000000..0419cf073c
--- /dev/null
+++ b/tests/specs/check/check_without_exclude_option/exclude_option/ignored/index.ts
@@ -0,0 +1 @@
+export { nothing };
diff --git a/tests/specs/check/check_without_exclude_option/exclude_option/index.ts b/tests/specs/check/check_without_exclude_option/exclude_option/index.ts
new file mode 100644
index 0000000000..8335ca3a2e
--- /dev/null
+++ b/tests/specs/check/check_without_exclude_option/exclude_option/index.ts
@@ -0,0 +1,5 @@
+import { nothing } from "./ignored/index.ts";
+
+const foo = 1;
+
+export { foo, nothing };
diff --git a/tests/specs/check/cjs_default_export/main.out b/tests/specs/check/cjs_default_export/main.out
index f284593a19..6c5f18b632 100644
--- a/tests/specs/check/cjs_default_export/main.out
+++ b/tests/specs/check/cjs_default_export/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/cjs-default-export
+Download http://localhost:4260/@denotest%2fcjs-default-export
 Download http://localhost:4260/@denotest/cjs-default-export/1.0.0.tgz
 Check file:///[WILDCARD]/main.ts
 error: TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
diff --git a/tests/specs/check/css_import/exists_run_with_check.out b/tests/specs/check/css_import/exists_run_with_check.out
index 1a1dafeb74..315769e40c 100644
--- a/tests/specs/check/css_import/exists_run_with_check.out
+++ b/tests/specs/check/css_import/exists_run_with_check.out
@@ -1,3 +1,3 @@
-error: Expected a JavaScript or TypeScript module, but identified a Unknown module. Importing these types of modules is currently not supported.
+error: Expected a JavaScript or TypeScript module, but identified a Css module. Importing these types of modules is currently not supported.
   Specifier: file:///[WILDLINE]/app.css
     at file:///[WILDLINE]/exists.ts:2:8
diff --git a/tests/specs/check/declaration_header_file_with_no_exports/__test__.jsonc b/tests/specs/check/declaration_header_file_with_no_exports/__test__.jsonc
new file mode 100644
index 0000000000..08fc0a2d6e
--- /dev/null
+++ b/tests/specs/check/declaration_header_file_with_no_exports/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "check --quiet declaration_header_file_with_no_exports.ts",
+  "output": ""
+}
diff --git a/tests/testdata/check/declaration_header_file_with_no_exports.ts b/tests/specs/check/declaration_header_file_with_no_exports/declaration_header_file_with_no_exports.ts
similarity index 100%
rename from tests/testdata/check/declaration_header_file_with_no_exports.ts
rename to tests/specs/check/declaration_header_file_with_no_exports/declaration_header_file_with_no_exports.ts
diff --git a/tests/testdata/run/empty.ts b/tests/specs/check/declaration_header_file_with_no_exports/declaration_header_file_with_no_exports_js.d.ts
similarity index 100%
rename from tests/testdata/run/empty.ts
rename to tests/specs/check/declaration_header_file_with_no_exports/declaration_header_file_with_no_exports_js.d.ts
diff --git a/tests/testdata/check/declaration_header_file_with_no_exports_js.js b/tests/specs/check/declaration_header_file_with_no_exports/declaration_header_file_with_no_exports_js.js
similarity index 100%
rename from tests/testdata/check/declaration_header_file_with_no_exports_js.js
rename to tests/specs/check/declaration_header_file_with_no_exports/declaration_header_file_with_no_exports_js.js
diff --git a/tests/specs/check/jsx_import_source_not_in_graph/__test__.jsonc b/tests/specs/check/jsx_import_source_not_in_graph/__test__.jsonc
new file mode 100644
index 0000000000..de0339cfb4
--- /dev/null
+++ b/tests/specs/check/jsx_import_source_not_in_graph/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "check main.ts",
+  "output": "main.out"
+}
diff --git a/tests/specs/check/jsx_import_source_not_in_graph/deno.json b/tests/specs/check/jsx_import_source_not_in_graph/deno.json
new file mode 100644
index 0000000000..219ef515f6
--- /dev/null
+++ b/tests/specs/check/jsx_import_source_not_in_graph/deno.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "npm:preact"
+  }
+}
diff --git a/tests/specs/check/jsx_import_source_not_in_graph/main.out b/tests/specs/check/jsx_import_source_not_in_graph/main.out
new file mode 100644
index 0000000000..1830c3186d
--- /dev/null
+++ b/tests/specs/check/jsx_import_source_not_in_graph/main.out
@@ -0,0 +1 @@
+Check file:///[WILDLINE]/main.ts
diff --git a/tests/specs/check/jsx_import_source_not_in_graph/main.ts b/tests/specs/check/jsx_import_source_not_in_graph/main.ts
new file mode 100644
index 0000000000..bf6b817963
--- /dev/null
+++ b/tests/specs/check/jsx_import_source_not_in_graph/main.ts
@@ -0,0 +1 @@
+console.log("Hello");
diff --git a/tests/specs/check/jsx_not_checked/__test__.jsonc b/tests/specs/check/jsx_not_checked/__test__.jsonc
new file mode 100644
index 0000000000..dbaa9b2eaf
--- /dev/null
+++ b/tests/specs/check/jsx_not_checked/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "check jsx_not_checked/main.jsx",
+  "output": "jsx_not_checked/main.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/check/jsx_not_checked/main.jsx b/tests/specs/check/jsx_not_checked/jsx_not_checked/main.jsx
similarity index 100%
rename from tests/testdata/check/jsx_not_checked/main.jsx
rename to tests/specs/check/jsx_not_checked/jsx_not_checked/main.jsx
diff --git a/tests/testdata/check/jsx_not_checked/main.out b/tests/specs/check/jsx_not_checked/jsx_not_checked/main.out
similarity index 100%
rename from tests/testdata/check/jsx_not_checked/main.out
rename to tests/specs/check/jsx_not_checked/jsx_not_checked/main.out
diff --git a/tests/testdata/check/jsx_not_checked/other.ts b/tests/specs/check/jsx_not_checked/jsx_not_checked/other.ts
similarity index 100%
rename from tests/testdata/check/jsx_not_checked/other.ts
rename to tests/specs/check/jsx_not_checked/jsx_not_checked/other.ts
diff --git a/tests/specs/check/module_detection_force/__test__.jsonc b/tests/specs/check/module_detection_force/__test__.jsonc
new file mode 100644
index 0000000000..9c892bd723
--- /dev/null
+++ b/tests/specs/check/module_detection_force/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "check --quiet module_detection_force/main.ts",
+  "output": ""
+}
diff --git a/tests/testdata/check/module_detection_force/import.ts b/tests/specs/check/module_detection_force/module_detection_force/import.ts
similarity index 100%
rename from tests/testdata/check/module_detection_force/import.ts
rename to tests/specs/check/module_detection_force/module_detection_force/import.ts
diff --git a/tests/testdata/check/module_detection_force/main.ts b/tests/specs/check/module_detection_force/module_detection_force/main.ts
similarity index 100%
rename from tests/testdata/check/module_detection_force/main.ts
rename to tests/specs/check/module_detection_force/module_detection_force/main.ts
diff --git a/tests/specs/check/package_json/install.out b/tests/specs/check/package_json/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/check/package_json/install.out
+++ b/tests/specs/check/package_json/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/check/package_json_auto_install/check.out b/tests/specs/check/package_json_auto_install/check.out
index db9bd198ca..6b75c8642d 100644
--- a/tests/specs/check/package_json_auto_install/check.out
+++ b/tests/specs/check/package_json_auto_install/check.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 Check file://[WILDCARD]/main.ts
diff --git a/tests/specs/check/package_json_fail_check/install.out b/tests/specs/check/package_json_fail_check/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/check/package_json_fail_check/install.out
+++ b/tests/specs/check/package_json_fail_check/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/check/package_json_with_deno_json/install.out b/tests/specs/check/package_json_with_deno_json/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/check/package_json_with_deno_json/install.out
+++ b/tests/specs/check/package_json_with_deno_json/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/cli/otel_basic/__test__.jsonc b/tests/specs/cli/otel_basic/__test__.jsonc
new file mode 100644
index 0000000000..5a27e92625
--- /dev/null
+++ b/tests/specs/cli/otel_basic/__test__.jsonc
@@ -0,0 +1,32 @@
+{
+  "steps": [
+    {
+      "args": "run -A main.ts basic.ts",
+      "envs": {
+        "DENO_UNSTABLE_OTEL_DETERMINISTIC": "1"
+      },
+      "output": "basic.out"
+    },
+    {
+      "args": "run -A main.ts natural_exit.ts",
+      "envs": {
+        "DENO_UNSTABLE_OTEL_DETERMINISTIC": "1"
+      },
+      "output": "natural_exit.out"
+    },
+    {
+      "args": "run -A main.ts deno_dot_exit.ts",
+      "envs": {
+        "DENO_UNSTABLE_OTEL_DETERMINISTIC": "1"
+      },
+      "output": "deno_dot_exit.out"
+    },
+    {
+      "args": "run -A main.ts uncaught.ts",
+      "envs": {
+        "DENO_UNSTABLE_OTEL_DETERMINISTIC": "1"
+      },
+      "output": "uncaught.out"
+    }
+  ]
+}
diff --git a/tests/specs/cli/otel_basic/basic.out b/tests/specs/cli/otel_basic/basic.out
new file mode 100644
index 0000000000..3f0554f96a
--- /dev/null
+++ b/tests/specs/cli/otel_basic/basic.out
@@ -0,0 +1,76 @@
+{
+  "spans": [
+    {
+      "traceId": "00000000000000000000000000000002",
+      "spanId": "0000000000000003",
+      "traceState": "",
+      "parentSpanId": "0000000000000001",
+      "flags": 1,
+      "name": "inner span",
+      "kind": 1,
+      "startTimeUnixNano": "[WILDCARD]",
+      "endTimeUnixNano": "[WILDCARD]",
+      "attributes": [],
+      "droppedAttributesCount": 0,
+      "events": [],
+      "droppedEventsCount": 0,
+      "links": [],
+      "droppedLinksCount": 0,
+      "status": {
+        "message": "",
+        "code": 0
+      }
+    },
+    {
+      "traceId": "00000000000000000000000000000002",
+      "spanId": "0000000000000001",
+      "traceState": "",
+      "parentSpanId": "",
+      "flags": 1,
+      "name": "outer span",
+      "kind": 1,
+      "startTimeUnixNano": "[WILDCARD]",
+      "endTimeUnixNano": "[WILDCARD]",
+      "attributes": [],
+      "droppedAttributesCount": 0,
+      "events": [],
+      "droppedEventsCount": 0,
+      "links": [],
+      "droppedLinksCount": 0,
+      "status": {
+        "message": "",
+        "code": 0
+      }
+    }
+  ],
+  "logs": [
+    {
+      "timeUnixNano": "0",
+      "observedTimeUnixNano": "[WILDCARD]",
+      "severityNumber": 9,
+      "severityText": "INFO",
+      "body": {
+        "stringValue": "log 1\n"
+      },
+      "attributes": [],
+      "droppedAttributesCount": 0,
+      "flags": 1,
+      "traceId": "00000000000000000000000000000002",
+      "spanId": "0000000000000003"
+    },
+    {
+      "timeUnixNano": "0",
+      "observedTimeUnixNano": "[WILDCARD]",
+      "severityNumber": 9,
+      "severityText": "INFO",
+      "body": {
+        "stringValue": "log 2\n"
+      },
+      "attributes": [],
+      "droppedAttributesCount": 0,
+      "flags": 1,
+      "traceId": "00000000000000000000000000000002",
+      "spanId": "0000000000000003"
+    }
+  ]
+}
diff --git a/tests/specs/cli/otel_basic/basic.ts b/tests/specs/cli/otel_basic/basic.ts
new file mode 100644
index 0000000000..5a178794a3
--- /dev/null
+++ b/tests/specs/cli/otel_basic/basic.ts
@@ -0,0 +1,24 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+async function inner() {
+  using _span = new Deno.tracing.Span("inner span");
+  console.log("log 1");
+  await 1;
+  console.log("log 2");
+}
+
+const server = Deno.serve({
+  port: 0,
+  async onListen({ port }) {
+    try {
+      await fetch(`http://localhost:${port}`);
+    } finally {
+      server.shutdown();
+    }
+  },
+  handler: async (_req) => {
+    using _span = new Deno.tracing.Span("outer span");
+    await inner();
+    return new Response(null, { status: 200 });
+  },
+});
diff --git a/tests/specs/cli/otel_basic/deno.json b/tests/specs/cli/otel_basic/deno.json
new file mode 100644
index 0000000000..105514e133
--- /dev/null
+++ b/tests/specs/cli/otel_basic/deno.json
@@ -0,0 +1,4 @@
+{
+  "lock": false,
+  "importMap": "../../../../import_map.json"
+}
diff --git a/tests/specs/cli/otel_basic/deno_dot_exit.out b/tests/specs/cli/otel_basic/deno_dot_exit.out
new file mode 100644
index 0000000000..98a41cf606
--- /dev/null
+++ b/tests/specs/cli/otel_basic/deno_dot_exit.out
@@ -0,0 +1,19 @@
+{
+  "spans": [],
+  "logs": [
+    {
+      "timeUnixNano": "0",
+      "observedTimeUnixNano": "[WILDCARD]",
+      "severityNumber": 9,
+      "severityText": "INFO",
+      "body": {
+        "stringValue": "log 1\n"
+      },
+      "attributes": [],
+      "droppedAttributesCount": 0,
+      "flags": 0,
+      "traceId": "",
+      "spanId": ""
+    }
+  ]
+}
diff --git a/tests/specs/cli/otel_basic/deno_dot_exit.ts b/tests/specs/cli/otel_basic/deno_dot_exit.ts
new file mode 100644
index 0000000000..73540fd9e8
--- /dev/null
+++ b/tests/specs/cli/otel_basic/deno_dot_exit.ts
@@ -0,0 +1,2 @@
+console.log("log 1");
+Deno.exit(0);
diff --git a/tests/specs/cli/otel_basic/main.ts b/tests/specs/cli/otel_basic/main.ts
new file mode 100644
index 0000000000..6c49462a0b
--- /dev/null
+++ b/tests/specs/cli/otel_basic/main.ts
@@ -0,0 +1,38 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+const data = {
+  spans: [],
+  logs: [],
+};
+
+const server = Deno.serve(
+  {
+    port: 0,
+    onListen({ port }) {
+      const command = new Deno.Command(Deno.execPath(), {
+        args: ["run", "-A", "--unstable-otel", Deno.args[0]],
+        env: {
+          OTEL_EXPORTER_OTLP_PROTOCOL: "http/json",
+          OTEL_EXPORTER_OTLP_ENDPOINT: `http://localhost:${port}`,
+        },
+        stdout: "null",
+      });
+      const child = command.spawn();
+      child.output().then(() => {
+        server.shutdown();
+
+        console.log(JSON.stringify(data, null, 2));
+      });
+    },
+    async handler(req) {
+      const body = await req.json();
+      if (body.resourceLogs) {
+        data.logs.push(...body.resourceLogs[0].scopeLogs[0].logRecords);
+      }
+      if (body.resourceSpans) {
+        data.spans.push(...body.resourceSpans[0].scopeSpans[0].spans);
+      }
+      return Response.json({ partialSuccess: {} }, { status: 200 });
+    },
+  },
+);
diff --git a/tests/specs/cli/otel_basic/natural_exit.out b/tests/specs/cli/otel_basic/natural_exit.out
new file mode 100644
index 0000000000..98a41cf606
--- /dev/null
+++ b/tests/specs/cli/otel_basic/natural_exit.out
@@ -0,0 +1,19 @@
+{
+  "spans": [],
+  "logs": [
+    {
+      "timeUnixNano": "0",
+      "observedTimeUnixNano": "[WILDCARD]",
+      "severityNumber": 9,
+      "severityText": "INFO",
+      "body": {
+        "stringValue": "log 1\n"
+      },
+      "attributes": [],
+      "droppedAttributesCount": 0,
+      "flags": 0,
+      "traceId": "",
+      "spanId": ""
+    }
+  ]
+}
diff --git a/tests/specs/cli/otel_basic/natural_exit.ts b/tests/specs/cli/otel_basic/natural_exit.ts
new file mode 100644
index 0000000000..d404782524
--- /dev/null
+++ b/tests/specs/cli/otel_basic/natural_exit.ts
@@ -0,0 +1 @@
+console.log("log 1");
diff --git a/tests/specs/cli/otel_basic/uncaught.out b/tests/specs/cli/otel_basic/uncaught.out
new file mode 100644
index 0000000000..a5a886bfeb
--- /dev/null
+++ b/tests/specs/cli/otel_basic/uncaught.out
@@ -0,0 +1,37 @@
+error: Uncaught (in promise) Error: uncaught
+throw new Error("uncaught");
+      ^
+    at file:///[WILDCARD]/tests/specs/cli/otel_basic/uncaught.ts:2:7
+{
+  "spans": [],
+  "logs": [
+    {
+      "timeUnixNano": "0",
+      "observedTimeUnixNano": "[WILDCARD]",
+      "severityNumber": 9,
+      "severityText": "INFO",
+      "body": {
+        "stringValue": "log 1\n"
+      },
+      "attributes": [],
+      "droppedAttributesCount": 0,
+      "flags": 0,
+      "traceId": "",
+      "spanId": ""
+    },
+    {
+      "timeUnixNano": "0",
+      "observedTimeUnixNano": "[WILDCARD]",
+      "severityNumber": 17,
+      "severityText": "ERROR",
+      "body": {
+        "stringValue": "error: Uncaught (in promise) Error: uncaught\nthrow new Error(\"uncaught\");\n      ^\n    at file:///[WILDCARD]/tests/specs/cli/otel_basic/uncaught.ts:2:7"
+      },
+      "attributes": [],
+      "droppedAttributesCount": 0,
+      "flags": 0,
+      "traceId": "",
+      "spanId": ""
+    }
+  ]
+}
diff --git a/tests/specs/cli/otel_basic/uncaught.ts b/tests/specs/cli/otel_basic/uncaught.ts
new file mode 100644
index 0000000000..eca7c05cb2
--- /dev/null
+++ b/tests/specs/cli/otel_basic/uncaught.ts
@@ -0,0 +1,2 @@
+console.log("log 1");
+throw new Error("uncaught");
diff --git a/tests/specs/compile/byonm_main_sub_dir/deno.json b/tests/specs/compile/byonm_main_sub_dir/deno.json
index 6134d86d1c..fde86a1efb 100644
--- a/tests/specs/compile/byonm_main_sub_dir/deno.json
+++ b/tests/specs/compile/byonm_main_sub_dir/deno.json
@@ -1,3 +1,3 @@
 {
-  "unstable": ["byonm"]
+  "nodeModulesDir": "manual"
 }
diff --git a/tests/specs/compile/cjs/__test__.jsonc b/tests/specs/compile/cjs/__test__.jsonc
new file mode 100644
index 0000000000..9bdcf4724f
--- /dev/null
+++ b/tests/specs/compile/cjs/__test__.jsonc
@@ -0,0 +1,24 @@
+{
+  "tempDir": true,
+  "steps": [{
+    "if": "unix",
+    "args": "compile --output main main.js",
+    "output": "[WILDCARD]"
+  }, {
+    "if": "unix",
+    "commandName": "./main",
+    "args": [],
+    "output": "output.out",
+    "exitCode": 0
+  }, {
+    "if": "windows",
+    "args": "compile --output main.exe main.js",
+    "output": "[WILDCARD]"
+  }, {
+    "if": "windows",
+    "commandName": "./main.exe",
+    "args": [],
+    "output": "output.out",
+    "exitCode": 0
+  }]
+}
diff --git a/tests/specs/compile/cjs/add.cjs b/tests/specs/compile/cjs/add.cjs
new file mode 100644
index 0000000000..bf90601267
--- /dev/null
+++ b/tests/specs/compile/cjs/add.cjs
@@ -0,0 +1 @@
+module.exports = (a, b) => a + b;
diff --git a/tests/specs/compile/cjs/divide.cts b/tests/specs/compile/cjs/divide.cts
new file mode 100644
index 0000000000..d89a600a4e
--- /dev/null
+++ b/tests/specs/compile/cjs/divide.cts
@@ -0,0 +1 @@
+module.exports.divide = (a: number, b: number) => a / b;
diff --git a/tests/specs/compile/cjs/main.js b/tests/specs/compile/cjs/main.js
new file mode 100644
index 0000000000..c2a8c7be02
--- /dev/null
+++ b/tests/specs/compile/cjs/main.js
@@ -0,0 +1,5 @@
+import { add } from "./reexport.cjs";
+import { multiply } from "./multiply.cts";
+
+console.log(add(1, 2));
+console.log(multiply(2, 3));
diff --git a/tests/specs/compile/cjs/multiply.cts b/tests/specs/compile/cjs/multiply.cts
new file mode 100644
index 0000000000..3c0618cfc5
--- /dev/null
+++ b/tests/specs/compile/cjs/multiply.cts
@@ -0,0 +1,4 @@
+/// <reference types="npm:@types/node" />
+exports.multiply = function (a: number, b: number): number {
+  return require("./divide.cts").divide(a, 1 / b);
+};
diff --git a/tests/specs/compile/cjs/output.out b/tests/specs/compile/cjs/output.out
new file mode 100644
index 0000000000..2559e5c49e
--- /dev/null
+++ b/tests/specs/compile/cjs/output.out
@@ -0,0 +1,2 @@
+3
+6
diff --git a/tests/specs/compile/cjs/reexport.cjs b/tests/specs/compile/cjs/reexport.cjs
new file mode 100644
index 0000000000..af7cecfdf4
--- /dev/null
+++ b/tests/specs/compile/cjs/reexport.cjs
@@ -0,0 +1 @@
+module.exports.add = require("./add.cjs");
diff --git a/tests/specs/compile/npmrc_byonm/install.out b/tests/specs/compile/npmrc_byonm/install.out
index 30643527e6..f2ea78c3f8 100644
--- a/tests/specs/compile/npmrc_byonm/install.out
+++ b/tests/specs/compile/npmrc_byonm/install.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4261/@denotest/basic
-Download http://localhost:4262/@denotest2/basic
+Download http://localhost:4261/@denotest%2fbasic
+Download http://localhost:4262/@denotest2%2fbasic
 Download http://localhost:4261/@denotest/basic/1.0.0.tgz
 Download http://localhost:4262/@denotest2/basic/1.0.0.tgz
 Initialize @denotest2/basic@1.0.0
diff --git a/tests/specs/compile/package_json_type/__test__.jsonc b/tests/specs/compile/package_json_type/__test__.jsonc
new file mode 100644
index 0000000000..0abf121f05
--- /dev/null
+++ b/tests/specs/compile/package_json_type/__test__.jsonc
@@ -0,0 +1,27 @@
+{
+  "tempDir": true,
+  "steps": [{
+    "args": "install",
+    "output": "[WILDCARD]"
+  }, {
+    "if": "unix",
+    "args": "compile --output main main.js",
+    "output": "compile.out"
+  }, {
+    "if": "unix",
+    "commandName": "./main",
+    "args": [],
+    "output": "output.out",
+    "exitCode": 0
+  }, {
+    "if": "windows",
+    "args": "compile --output main.exe main.js",
+    "output": "compile.out"
+  }, {
+    "if": "windows",
+    "commandName": "./main.exe",
+    "args": [],
+    "output": "output.out",
+    "exitCode": 0
+  }]
+}
diff --git a/tests/specs/compile/package_json_type/add.js b/tests/specs/compile/package_json_type/add.js
new file mode 100644
index 0000000000..94b0263f0e
--- /dev/null
+++ b/tests/specs/compile/package_json_type/add.js
@@ -0,0 +1,3 @@
+module.exports.add = function (a, b) {
+  return require("./subtract.ts").subtract(a, -b);
+};
diff --git a/tests/specs/compile/package_json_type/compile.out b/tests/specs/compile/package_json_type/compile.out
new file mode 100644
index 0000000000..913e363c3e
--- /dev/null
+++ b/tests/specs/compile/package_json_type/compile.out
@@ -0,0 +1,2 @@
+Check file:///[WILDLINE]/main.js
+Compile file:///[WILDLINE]
diff --git a/tests/specs/compile/package_json_type/main.js b/tests/specs/compile/package_json_type/main.js
new file mode 100644
index 0000000000..8c55f673b0
--- /dev/null
+++ b/tests/specs/compile/package_json_type/main.js
@@ -0,0 +1,3 @@
+import { add } from "./add.js";
+
+console.log(add(1, 2));
diff --git a/tests/specs/compile/package_json_type/output.out b/tests/specs/compile/package_json_type/output.out
new file mode 100644
index 0000000000..00750edc07
--- /dev/null
+++ b/tests/specs/compile/package_json_type/output.out
@@ -0,0 +1 @@
+3
diff --git a/tests/specs/compile/package_json_type/package.json b/tests/specs/compile/package_json_type/package.json
new file mode 100644
index 0000000000..6e65b32ed5
--- /dev/null
+++ b/tests/specs/compile/package_json_type/package.json
@@ -0,0 +1,6 @@
+{
+  "type": "commonjs",
+  "dependencies": {
+    "@types/node": "*"
+  }
+}
diff --git a/tests/specs/compile/package_json_type/subtract.ts b/tests/specs/compile/package_json_type/subtract.ts
new file mode 100644
index 0000000000..e4f6760b77
--- /dev/null
+++ b/tests/specs/compile/package_json_type/subtract.ts
@@ -0,0 +1,2 @@
+/// <reference types="npm:@types/node" />
+module.exports.subtract = (a: number, b: number) => a - b;
diff --git a/tests/specs/compile/redirects/__test__.jsonc b/tests/specs/compile/redirects/__test__.jsonc
new file mode 100644
index 0000000000..07ce693999
--- /dev/null
+++ b/tests/specs/compile/redirects/__test__.jsonc
@@ -0,0 +1,22 @@
+{
+  "tempDir": true,
+  "steps": [{
+    "if": "unix",
+    "args": "compile -A --output main main.ts",
+    "output": "[WILDCARD]"
+  }, {
+    "if": "unix",
+    "commandName": "./main",
+    "args": [],
+    "output": "main.out"
+  }, {
+    "if": "windows",
+    "args": "compile -A --output main.exe main.ts",
+    "output": "[WILDCARD]"
+  }, {
+    "if": "windows",
+    "commandName": "./main.exe",
+    "args": [],
+    "output": "main.out"
+  }]
+}
diff --git a/tests/testdata/run/003_relative_import.ts.out b/tests/specs/compile/redirects/main.out
similarity index 100%
rename from tests/testdata/run/003_relative_import.ts.out
rename to tests/specs/compile/redirects/main.out
diff --git a/tests/specs/compile/redirects/main.ts b/tests/specs/compile/redirects/main.ts
new file mode 100644
index 0000000000..4396319014
--- /dev/null
+++ b/tests/specs/compile/redirects/main.ts
@@ -0,0 +1 @@
+import "http://localhost:4546/run/003_relative_import.ts";
diff --git a/tests/specs/doc/deno_doc/__test__.jsonc b/tests/specs/doc/deno_doc/__test__.jsonc
index 251565ecb4..5557757e04 100644
--- a/tests/specs/doc/deno_doc/__test__.jsonc
+++ b/tests/specs/doc/deno_doc/__test__.jsonc
@@ -2,16 +2,10 @@
   "steps": [{
     "args": "doc deno_doc.ts",
     "output": "foo.out",
-    "exitCode": 0,
-    "envs": {
-      "NO_COLOR": "1"
-    }
+    "exitCode": 0
   }, {
     "args": "doc deno_doc2.ts",
     "output": "bar.out",
-    "exitCode": 0,
-    "envs": {
-      "NO_COLOR": "1"
-    }
+    "exitCode": 0
   }]
 }
diff --git a/tests/specs/eval/pkg_json_type_cjs/__test__.jsonc b/tests/specs/eval/pkg_json_type_cjs/__test__.jsonc
new file mode 100644
index 0000000000..cd3804d773
--- /dev/null
+++ b/tests/specs/eval/pkg_json_type_cjs/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "eval console.log(1)",
+  "output": "1\n"
+}
diff --git a/tests/specs/eval/pkg_json_type_cjs/package.json b/tests/specs/eval/pkg_json_type_cjs/package.json
new file mode 100644
index 0000000000..5bbefffbab
--- /dev/null
+++ b/tests/specs/eval/pkg_json_type_cjs/package.json
@@ -0,0 +1,3 @@
+{
+  "type": "commonjs"
+}
diff --git a/tests/specs/fmt/html/well_formatted.html b/tests/specs/fmt/html/well_formatted.html
index c0c06cd9bd..7af705c049 100644
--- a/tests/specs/fmt/html/well_formatted.html
+++ b/tests/specs/fmt/html/well_formatted.html
@@ -1,4 +1,4 @@
-<div class="container">content</div>
+<div class="container">content<br></div>
 
 <script>
   let counter = 0;
diff --git a/tests/specs/fmt/yaml/__test__.jsonc b/tests/specs/fmt/yaml/__test__.jsonc
index 499b4144b7..71a2e06827 100644
--- a/tests/specs/fmt/yaml/__test__.jsonc
+++ b/tests/specs/fmt/yaml/__test__.jsonc
@@ -8,6 +8,30 @@
     "well_formatted": {
       "args": "fmt --check well_formatted.yml",
       "output": "Checked 1 file\n"
+    },
+    "ignore_line": {
+      "args": "fmt --check ignore_line.yml",
+      "output": "Checked 1 file\n"
+    },
+    "ignore_file": {
+      "args": "fmt ignore_file.yaml",
+      "output": "Checked 1 file\n"
+    },
+    "ignore_file2": {
+      "args": "fmt ignore_file2.yaml",
+      "output": "Checked 1 file\n"
+    },
+    "ignore_file3": {
+      "args": "fmt ignore_file3.yaml",
+      "output": "Checked 1 file\n"
+    },
+    "ignore_file4": {
+      "args": "fmt ignore_file4.yaml",
+      "output": "Checked 1 file\n"
+    },
+    "wrong_file_ignore": {
+      "args": "fmt wrong_file_ignore.yaml",
+      "output": "wrong_file_ignore.out"
     }
   }
 }
diff --git a/tests/specs/fmt/yaml/ignore_file.yaml b/tests/specs/fmt/yaml/ignore_file.yaml
new file mode 100644
index 0000000000..c724c7bde5
--- /dev/null
+++ b/tests/specs/fmt/yaml/ignore_file.yaml
@@ -0,0 +1,2 @@
+# deno-fmt-ignore-file
+{{something crazy
\ No newline at end of file
diff --git a/tests/specs/fmt/yaml/ignore_file2.yaml b/tests/specs/fmt/yaml/ignore_file2.yaml
new file mode 100644
index 0000000000..a2053533ef
--- /dev/null
+++ b/tests/specs/fmt/yaml/ignore_file2.yaml
@@ -0,0 +1,2 @@
+#deno-fmt-ignore-file
+{{something crazy
\ No newline at end of file
diff --git a/tests/specs/fmt/yaml/ignore_file3.yaml b/tests/specs/fmt/yaml/ignore_file3.yaml
new file mode 100644
index 0000000000..a3927a7b19
--- /dev/null
+++ b/tests/specs/fmt/yaml/ignore_file3.yaml
@@ -0,0 +1,5 @@
+# Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor
+# incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, 
+# quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat. 
+# deno-fmt-ignore-file
+{{something crazy
\ No newline at end of file
diff --git a/tests/specs/fmt/yaml/ignore_file4.yaml b/tests/specs/fmt/yaml/ignore_file4.yaml
new file mode 100644
index 0000000000..c32fe9f2be
--- /dev/null
+++ b/tests/specs/fmt/yaml/ignore_file4.yaml
@@ -0,0 +1,2 @@
+# deno-fmt-ignore-file Because this is templated yaml file
+{{something crazy
\ No newline at end of file
diff --git a/tests/specs/fmt/yaml/ignore_line.yml b/tests/specs/fmt/yaml/ignore_line.yml
new file mode 100644
index 0000000000..490adcb5f7
--- /dev/null
+++ b/tests/specs/fmt/yaml/ignore_line.yml
@@ -0,0 +1,2 @@
+# deno-fmt-ignore
+-     Test
diff --git a/tests/specs/fmt/yaml/wrong_file_ignore.out b/tests/specs/fmt/yaml/wrong_file_ignore.out
new file mode 100644
index 0000000000..065dc98db0
--- /dev/null
+++ b/tests/specs/fmt/yaml/wrong_file_ignore.out
@@ -0,0 +1,7 @@
+Error formatting: [WILDCARD]wrong_file_ignore.yaml
+   parse error at line 5, column 1
+  |
+5 | {{something crazy
+  | ^
+
+Checked 1 file
diff --git a/tests/specs/fmt/yaml/wrong_file_ignore.yaml b/tests/specs/fmt/yaml/wrong_file_ignore.yaml
new file mode 100644
index 0000000000..8019d989d3
--- /dev/null
+++ b/tests/specs/fmt/yaml/wrong_file_ignore.yaml
@@ -0,0 +1,5 @@
+# File ignore directive only works if it's in the first cluster
+# of comment, ie. there are no empty lines after the first n-leading lines.
+
+# deno-fmt-ignore-file
+{{something crazy
\ No newline at end of file
diff --git a/tests/specs/future/unstable_flags/main.js b/tests/specs/future/unstable_flags/main.js
index 51af892f6b..8cc8960d97 100644
--- a/tests/specs/future/unstable_flags/main.js
+++ b/tests/specs/future/unstable_flags/main.js
@@ -1,4 +1,3 @@
-console.log(typeof await navigator.gpu.requestAdapter() === "object"); // Throws without `--unstable-gpu`
 console.log(typeof Deno.dlopen === "function"); // Undefined without `--unstable-ffi`
 console.log(
   // Undefined without `--unstable-fs`
diff --git a/tests/specs/future/unstable_flags/main.out b/tests/specs/future/unstable_flags/main.out
index b979d62f4f..bb101b641b 100644
--- a/tests/specs/future/unstable_flags/main.out
+++ b/tests/specs/future/unstable_flags/main.out
@@ -1,3 +1,2 @@
 true
 true
-true
diff --git a/tests/specs/info/byonm/__test__.jsonc b/tests/specs/info/byonm/__test__.jsonc
new file mode 100644
index 0000000000..6c9ba7dada
--- /dev/null
+++ b/tests/specs/info/byonm/__test__.jsonc
@@ -0,0 +1,11 @@
+{
+  "tempDir": true,
+  "steps": [{
+    "args": "install",
+    "output": "[WILDCARD]"
+  }, {
+    "args": "info npm:@denotest/add",
+    "output": "info.out",
+    "exitCode": 1
+  }]
+}
diff --git a/tests/specs/info/byonm/deno.json b/tests/specs/info/byonm/deno.json
new file mode 100644
index 0000000000..4b88c71fbb
--- /dev/null
+++ b/tests/specs/info/byonm/deno.json
@@ -0,0 +1,6 @@
+{
+  "nodeModulesDir": "manual",
+  "imports": {
+    "chalk": "npm:@denotest/add"
+  }
+}
diff --git a/tests/specs/info/byonm/info.out b/tests/specs/info/byonm/info.out
new file mode 100644
index 0000000000..4e6f11a88f
--- /dev/null
+++ b/tests/specs/info/byonm/info.out
@@ -0,0 +1 @@
+error: Resolving npm specifier entrypoints this way is currently not supported with "nodeModules": "manual". In the meantime, try with --node-modules-dir=auto instead
diff --git a/tests/specs/info/byonm/package.json b/tests/specs/info/byonm/package.json
new file mode 100644
index 0000000000..15a786ad71
--- /dev/null
+++ b/tests/specs/info/byonm/package.json
@@ -0,0 +1,5 @@
+{
+  "dependencies": {
+    "@denotest/add": "*"
+  }
+}
diff --git a/tests/specs/info/flag/041_info_flag.out b/tests/specs/info/flag/041_info_flag.out
index 3506a29e48..72a00be303 100644
--- a/tests/specs/info/flag/041_info_flag.out
+++ b/tests/specs/info/flag/041_info_flag.out
@@ -1,5 +1,5 @@
 DENO_DIR location: [WILDCARD]
-Remote modules cache: [WILDCARD]deps
+Remote modules cache: [WILDCARD]remote
 npm modules cache: [WILDCARD]npm
 Emitted modules cache: [WILDCARD]gen
 Language server registries cache: [WILDCARD]registries
diff --git a/tests/specs/info/flag_location/041_info_flag_location.out b/tests/specs/info/flag_location/041_info_flag_location.out
index b9e72f6590..684db2eec5 100644
--- a/tests/specs/info/flag_location/041_info_flag_location.out
+++ b/tests/specs/info/flag_location/041_info_flag_location.out
@@ -1,5 +1,5 @@
 DENO_DIR location: [WILDCARD]
-Remote modules cache: [WILDCARD]deps
+Remote modules cache: [WILDCARD]remote
 npm modules cache: [WILDCARD]npm
 Emitted modules cache: [WILDCARD]gen
 Language server registries cache: [WILDCARD]registries
diff --git a/tests/specs/info/import_map/__test__.jsonc b/tests/specs/info/import_map/__test__.jsonc
index 725276925e..7aba603e0b 100644
--- a/tests/specs/info/import_map/__test__.jsonc
+++ b/tests/specs/info/import_map/__test__.jsonc
@@ -1,5 +1,9 @@
 {
-  "args": "info preact/debug",
-  "output": "with_import_map.out",
-  "exitCode": 0
+  "steps": [
+    {
+      "args": "info preact/debug",
+      "output": "with_import_map.out",
+      "exitCode": 0
+    }
+  ]
 }
diff --git a/tests/specs/info/json/info_json.out b/tests/specs/info/json/info_json.out
index 607489ca39..551f61026d 100644
--- a/tests/specs/info/json/info_json.out
+++ b/tests/specs/info/json/info_json.out
@@ -1,7 +1,7 @@
 {
   "version": 1,
   "denoDir": "[WILDCARD]",
-  "modulesCache": "[WILDCARD]deps",
+  "modulesCache": "[WILDCARD]remote",
   "npmCache": "[WILDCARD]npm",
   "typescriptCache": "[WILDCARD]gen",
   "registryCache": "[WILDCARD]registries",
diff --git a/tests/specs/info/json_location/info_json_location.out b/tests/specs/info/json_location/info_json_location.out
index 004bf03db1..6d01ba451d 100644
--- a/tests/specs/info/json_location/info_json_location.out
+++ b/tests/specs/info/json_location/info_json_location.out
@@ -1,7 +1,7 @@
 {
   "version": 1,
   "denoDir": "[WILDCARD]",
-  "modulesCache": "[WILDCARD]deps",
+  "modulesCache": "[WILDCARD]remote",
   "npmCache": "[WILDCARD]npm",
   "typescriptCache": "[WILDCARD]gen",
   "registryCache": "[WILDCARD]registries",
diff --git a/tests/specs/info/package_json_basic/install.out b/tests/specs/info/package_json_basic/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/info/package_json_basic/install.out
+++ b/tests/specs/info/package_json_basic/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/info/workspace_member/__test__.jsonc b/tests/specs/info/workspace_member/__test__.jsonc
new file mode 100644
index 0000000000..d13d3b03e8
--- /dev/null
+++ b/tests/specs/info/workspace_member/__test__.jsonc
@@ -0,0 +1,16 @@
+{
+  "tests": {
+    "member_folder": {
+      "args": "info --quiet foo",
+      "cwd": "member",
+      "output": "info_workspace_member.out",
+      "exitCode": 0
+    },
+    "member_folder_sub": {
+      "args": "info --quiet foo",
+      "cwd": "member/sub",
+      "output": "info_workspace_member_sub.out",
+      "exitCode": 0
+    }
+  }
+}
diff --git a/tests/specs/info/workspace_member/deno.json b/tests/specs/info/workspace_member/deno.json
new file mode 100644
index 0000000000..f88028aeab
--- /dev/null
+++ b/tests/specs/info/workspace_member/deno.json
@@ -0,0 +1,3 @@
+{
+  "workspace": ["./member"]
+}
diff --git a/tests/specs/info/workspace_member/info_workspace_member.out b/tests/specs/info/workspace_member/info_workspace_member.out
new file mode 100644
index 0000000000..e0dc0b6753
--- /dev/null
+++ b/tests/specs/info/workspace_member/info_workspace_member.out
@@ -0,0 +1,6 @@
+local: [WILDCARD]file.ts
+type: TypeScript
+dependencies: 0 unique
+size: [WILDCARD]
+
+file://[WILDCARD]/member/sub/file.ts ([WILDCARD])
diff --git a/tests/specs/info/workspace_member/info_workspace_member_sub.out b/tests/specs/info/workspace_member/info_workspace_member_sub.out
new file mode 100644
index 0000000000..e0dc0b6753
--- /dev/null
+++ b/tests/specs/info/workspace_member/info_workspace_member_sub.out
@@ -0,0 +1,6 @@
+local: [WILDCARD]file.ts
+type: TypeScript
+dependencies: 0 unique
+size: [WILDCARD]
+
+file://[WILDCARD]/member/sub/file.ts ([WILDCARD])
diff --git a/tests/specs/info/workspace_member/member/deno.json b/tests/specs/info/workspace_member/member/deno.json
new file mode 100644
index 0000000000..66aac29046
--- /dev/null
+++ b/tests/specs/info/workspace_member/member/deno.json
@@ -0,0 +1,5 @@
+{
+  "imports": {
+    "foo": "./sub/file.ts"
+  }
+}
diff --git a/tests/specs/info/workspace_member/member/sub/file.ts b/tests/specs/info/workspace_member/member/sub/file.ts
new file mode 100644
index 0000000000..cb0ff5c3b5
--- /dev/null
+++ b/tests/specs/info/workspace_member/member/sub/file.ts
@@ -0,0 +1 @@
+export {};
diff --git a/tests/specs/install/byonm_run_tag_after_install/__test__.jsonc b/tests/specs/install/byonm_run_tag_after_install/__test__.jsonc
new file mode 100644
index 0000000000..3803fd26f7
--- /dev/null
+++ b/tests/specs/install/byonm_run_tag_after_install/__test__.jsonc
@@ -0,0 +1,44 @@
+{
+  "tempDir": true,
+
+  "tests": {
+    "tag_with_byonm": {
+      "steps": [
+        {
+          "args": "install",
+          "output": "[WILDCARD]"
+        },
+        {
+          "args": "run -A main.ts",
+          "output": ""
+        }
+      ]
+    },
+    "no_tag_then_tag": {
+      "steps": [
+        {
+          "args": "run -A replace-version-req.ts 1.0.0",
+          "output": ""
+        },
+        {
+          "args": "install",
+          "output": "[WILDCARD]"
+        },
+        {
+          "args": "run -A replace-version-req.ts latest",
+          "output": ""
+        },
+        {
+          "args": "run -A main.ts",
+          "output": "node_modules_out_of_date.out",
+          "exitCode": 1
+        },
+        {
+          "args": "install",
+          "output": "[WILDCARD]"
+        },
+        { "args": "run -A main.ts", "output": "" }
+      ]
+    }
+  }
+}
diff --git a/tests/specs/install/byonm_run_tag_after_install/deno.json b/tests/specs/install/byonm_run_tag_after_install/deno.json
new file mode 100644
index 0000000000..13238b1697
--- /dev/null
+++ b/tests/specs/install/byonm_run_tag_after_install/deno.json
@@ -0,0 +1,5 @@
+{
+  "imports": {
+    "@denotest/esm-basic": "npm:@denotest/esm-basic@latest"
+  }
+}
diff --git a/tests/specs/install/byonm_run_tag_after_install/main.ts b/tests/specs/install/byonm_run_tag_after_install/main.ts
new file mode 100644
index 0000000000..7feb95f96a
--- /dev/null
+++ b/tests/specs/install/byonm_run_tag_after_install/main.ts
@@ -0,0 +1 @@
+import { add } from "@denotest/esm-basic";
diff --git a/tests/specs/install/byonm_run_tag_after_install/node_modules_out_of_date.out b/tests/specs/install/byonm_run_tag_after_install/node_modules_out_of_date.out
new file mode 100644
index 0000000000..2d7fc81d17
--- /dev/null
+++ b/tests/specs/install/byonm_run_tag_after_install/node_modules_out_of_date.out
@@ -0,0 +1,2 @@
+error: Could not find a matching package for 'npm:@denotest/esm-basic@latest' in the node_modules directory. Ensure you have all your JSR and npm dependencies listed in your deno.json or package.json, then run `deno install`. Alternatively, turn on auto-install by specifying `"nodeModulesDir": "auto"` in your deno.json file.
+    at [WILDCARD]main.ts:1:21
diff --git a/tests/node_compat/test/internet/package.json b/tests/specs/install/byonm_run_tag_after_install/package.json
similarity index 100%
rename from tests/node_compat/test/internet/package.json
rename to tests/specs/install/byonm_run_tag_after_install/package.json
diff --git a/tests/specs/install/byonm_run_tag_after_install/replace-version-req.ts b/tests/specs/install/byonm_run_tag_after_install/replace-version-req.ts
new file mode 100644
index 0000000000..6f86ce2b71
--- /dev/null
+++ b/tests/specs/install/byonm_run_tag_after_install/replace-version-req.ts
@@ -0,0 +1,7 @@
+const newReq = Deno.args[0]?.trim();
+if (!newReq) {
+  throw new Error("Missing required argument");
+}
+const config = JSON.parse(Deno.readTextFileSync("deno.json"));
+config.imports["@denotest/esm-basic"] = `npm:@denotest/esm-basic@${newReq}`;
+Deno.writeTextFileSync("deno.json", JSON.stringify(config));
diff --git a/tests/specs/install/future_install_global/install.out b/tests/specs/install/future_install_global/install.out
index 58cd88ada1..0fa1b97191 100644
--- a/tests/specs/install/future_install_global/install.out
+++ b/tests/specs/install/future_install_global/install.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 ✅ Successfully installed deno-test-bin[WILDCARD]
 [WILDCARD]
diff --git a/tests/specs/install/future_install_local_add_deno/install.out b/tests/specs/install/future_install_local_add_deno/install.out
index 93894a020c..2f73e5afb5 100644
--- a/tests/specs/install/future_install_local_add_deno/install.out
+++ b/tests/specs/install/future_install_local_add_deno/install.out
@@ -1,3 +1,3 @@
 Add npm:@denotest/esm-basic@1.0.0
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
diff --git a/tests/specs/install/future_install_local_add_npm/install.out b/tests/specs/install/future_install_local_add_npm/install.out
index 42161f3ae1..44bd9cac7e 100644
--- a/tests/specs/install/future_install_local_add_npm/install.out
+++ b/tests/specs/install/future_install_local_add_npm/install.out
@@ -1,4 +1,4 @@
 Add npm:@denotest/esm-basic@1.0.0
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/install/future_install_local_add_npm/package.json.out b/tests/specs/install/future_install_local_add_npm/package.json.out
index ad8518e791..613d986360 100644
--- a/tests/specs/install/future_install_local_add_npm/package.json.out
+++ b/tests/specs/install/future_install_local_add_npm/package.json.out
@@ -1,3 +1,5 @@
 {
-  "dependencies": { "@denotest/esm-basic": "^1.0.0" }
+  "dependencies": {
+    "@denotest/esm-basic": "^1.0.0"
+  }
 }
diff --git a/tests/specs/install/future_install_local_deno/install.out b/tests/specs/install/future_install_local_deno/install.out
index 15263a37b5..d0972f69e8 100644
--- a/tests/specs/install/future_install_local_deno/install.out
+++ b/tests/specs/install/future_install_local_deno/install.out
@@ -8,7 +8,7 @@ Download http://localhost:4545/subdir/print_hello.ts
 Download http://127.0.0.1:4250/@denotest/add/meta.json
 Download http://127.0.0.1:4250/@denotest/add/1.0.0_meta.json
 Download http://127.0.0.1:4250/@denotest/add/1.0.0/mod.ts
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Download http://127.0.0.1:4250/@std/testing/1.0.0/bdd.ts
 Download http://127.0.0.1:4250/@std/testing/1.0.0/types.ts
diff --git a/tests/specs/install/future_install_node_modules/install.out b/tests/specs/install/future_install_node_modules/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/install/future_install_node_modules/install.out
+++ b/tests/specs/install/future_install_node_modules/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/install/import_map_with_dir/__test__.jsonc b/tests/specs/install/import_map_with_dir/__test__.jsonc
new file mode 100644
index 0000000000..cbbc7cc2e1
--- /dev/null
+++ b/tests/specs/install/import_map_with_dir/__test__.jsonc
@@ -0,0 +1,9 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "install",
+      "output": ""
+    }
+  ]
+}
diff --git a/tests/specs/install/import_map_with_dir/deno.json b/tests/specs/install/import_map_with_dir/deno.json
new file mode 100644
index 0000000000..5c3224b071
--- /dev/null
+++ b/tests/specs/install/import_map_with_dir/deno.json
@@ -0,0 +1,5 @@
+{
+  "imports": {
+    "@assets": "./src/assets/"
+  }
+}
diff --git a/tests/specs/install/install_add_dep_existing/__test__.jsonc b/tests/specs/install/install_add_dep_existing/__test__.jsonc
new file mode 100644
index 0000000000..74c509a57d
--- /dev/null
+++ b/tests/specs/install/install_add_dep_existing/__test__.jsonc
@@ -0,0 +1,16 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "install npm:@denotest/esm-basic",
+      "output": "install.out"
+    },
+    {
+      "args": [
+        "eval",
+        "console.log(Deno.readTextFileSync('package.json').trim())"
+      ],
+      "output": "package.json.out"
+    }
+  ]
+}
diff --git a/tests/specs/install/install_add_dep_existing/install.out b/tests/specs/install/install_add_dep_existing/install.out
new file mode 100644
index 0000000000..44bd9cac7e
--- /dev/null
+++ b/tests/specs/install/install_add_dep_existing/install.out
@@ -0,0 +1,4 @@
+Add npm:@denotest/esm-basic@1.0.0
+Download http://localhost:4260/@denotest%2fesm-basic
+Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
+Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/install/install_add_dep_existing/package.json b/tests/specs/install/install_add_dep_existing/package.json
new file mode 100644
index 0000000000..d5ca56e004
--- /dev/null
+++ b/tests/specs/install/install_add_dep_existing/package.json
@@ -0,0 +1,3 @@
+{
+  "devDependencies": { "@denotest/esm-basic": "^1.0.0" }
+}
diff --git a/tests/specs/install/install_add_dep_existing/package.json.out b/tests/specs/install/install_add_dep_existing/package.json.out
new file mode 100644
index 0000000000..613d986360
--- /dev/null
+++ b/tests/specs/install/install_add_dep_existing/package.json.out
@@ -0,0 +1,5 @@
+{
+  "dependencies": {
+    "@denotest/esm-basic": "^1.0.0"
+  }
+}
diff --git a/tests/specs/install/install_add_dev/install.out b/tests/specs/install/install_add_dev/install.out
index 42161f3ae1..44bd9cac7e 100644
--- a/tests/specs/install/install_add_dev/install.out
+++ b/tests/specs/install/install_add_dev/install.out
@@ -1,4 +1,4 @@
 Add npm:@denotest/esm-basic@1.0.0
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/install/install_add_dev/package.json b/tests/specs/install/install_add_dev/package.json
index d5ca56e004..0967ef424b 100644
--- a/tests/specs/install/install_add_dev/package.json
+++ b/tests/specs/install/install_add_dev/package.json
@@ -1,3 +1 @@
-{
-  "devDependencies": { "@denotest/esm-basic": "^1.0.0" }
-}
+{}
diff --git a/tests/specs/install/install_add_dev/package.json.out b/tests/specs/install/install_add_dev/package.json.out
index d5ca56e004..866724397f 100644
--- a/tests/specs/install/install_add_dev/package.json.out
+++ b/tests/specs/install/install_add_dev/package.json.out
@@ -1,3 +1,5 @@
 {
-  "devDependencies": { "@denotest/esm-basic": "^1.0.0" }
+  "devDependencies": {
+    "@denotest/esm-basic": "^1.0.0"
+  }
 }
diff --git a/tests/specs/install/install_add_dev_existing/__test__.jsonc b/tests/specs/install/install_add_dev_existing/__test__.jsonc
new file mode 100644
index 0000000000..e4e2f8a31c
--- /dev/null
+++ b/tests/specs/install/install_add_dev_existing/__test__.jsonc
@@ -0,0 +1,16 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "install --dev npm:@denotest/esm-basic",
+      "output": "install.out"
+    },
+    {
+      "args": [
+        "eval",
+        "console.log(Deno.readTextFileSync('package.json').trim())"
+      ],
+      "output": "package.json.out"
+    }
+  ]
+}
diff --git a/tests/specs/install/install_add_dev_existing/install.out b/tests/specs/install/install_add_dev_existing/install.out
new file mode 100644
index 0000000000..44bd9cac7e
--- /dev/null
+++ b/tests/specs/install/install_add_dev_existing/install.out
@@ -0,0 +1,4 @@
+Add npm:@denotest/esm-basic@1.0.0
+Download http://localhost:4260/@denotest%2fesm-basic
+Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
+Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/install/install_add_dev_existing/package.json b/tests/specs/install/install_add_dev_existing/package.json
new file mode 100644
index 0000000000..ad8518e791
--- /dev/null
+++ b/tests/specs/install/install_add_dev_existing/package.json
@@ -0,0 +1,3 @@
+{
+  "dependencies": { "@denotest/esm-basic": "^1.0.0" }
+}
diff --git a/tests/specs/install/install_add_dev_existing/package.json.out b/tests/specs/install/install_add_dev_existing/package.json.out
new file mode 100644
index 0000000000..866724397f
--- /dev/null
+++ b/tests/specs/install/install_add_dev_existing/package.json.out
@@ -0,0 +1,5 @@
+{
+  "devDependencies": {
+    "@denotest/esm-basic": "^1.0.0"
+  }
+}
diff --git a/tests/specs/install/install_deprecated_package/install.out b/tests/specs/install/install_deprecated_package/install.out
index 95c0759092..32661d971d 100644
--- a/tests/specs/install/install_deprecated_package/install.out
+++ b/tests/specs/install/install_deprecated_package/install.out
@@ -1,5 +1,5 @@
 Add npm:@denotest/deprecated-package@1.0.0
-Download http://localhost:4260/@denotest/deprecated-package
+Download http://localhost:4260/@denotest%2fdeprecated-package
 Download http://localhost:4260/@denotest/deprecated-package/1.0.0.tgz
 Initialize @denotest/deprecated-package@1.0.0
 Warning The following packages are deprecated:
diff --git a/tests/specs/install/install_deprecated_package/package.json.out b/tests/specs/install/install_deprecated_package/package.json.out
index 4b4b08087a..0cf36cd24f 100644
--- a/tests/specs/install/install_deprecated_package/package.json.out
+++ b/tests/specs/install/install_deprecated_package/package.json.out
@@ -1,3 +1,5 @@
 {
-  "dependencies": { "@denotest/deprecated-package": "^1.0.0" }
+  "dependencies": {
+    "@denotest/deprecated-package": "^1.0.0"
+  }
 }
diff --git a/tests/specs/install/install_entrypoint/install.out b/tests/specs/install/install_entrypoint/install.out
index d702cf45ac..da10f3aa03 100644
--- a/tests/specs/install/install_entrypoint/install.out
+++ b/tests/specs/install/install_entrypoint/install.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
 Download http://127.0.0.1:4250/@denotest/add/meta.json
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://127.0.0.1:4250/@denotest/add/1.0.0_meta.json
 Download http://127.0.0.1:4250/@denotest/add/1.0.0/mod.ts
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
diff --git a/tests/specs/install/install_entrypoint/lifecycle.out b/tests/specs/install/install_entrypoint/lifecycle.out
index 8eae8ee120..b302ea3341 100644
--- a/tests/specs/install/install_entrypoint/lifecycle.out
+++ b/tests/specs/install/install_entrypoint/lifecycle.out
@@ -1,22 +1,11 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/node-lifecycle-scripts
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fnode-lifecycle-scripts
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/node-lifecycle-scripts/1.0.0.tgz
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Initialize @denotest/node-lifecycle-scripts@1.0.0
 Initialize @denotest/bin@1.0.0
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'preinstall' script
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'install' script
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'postinstall' script
 [UNORDERED_END]
-preinstall
-deno preinstall.js
-node preinstall.js
-install
-hello from install script
-postinstall[WILDCARD]
- _____________
-< postinstall >
- -------------
-        \   ^__^
-         \  (oo)\_______
-            (__)\       )\/\
-                ||----w |
-                ||     ||
diff --git a/tests/specs/install/installs_all_workspace_imports/__test__.jsonc b/tests/specs/install/installs_all_workspace_imports/__test__.jsonc
new file mode 100644
index 0000000000..254fe8b989
--- /dev/null
+++ b/tests/specs/install/installs_all_workspace_imports/__test__.jsonc
@@ -0,0 +1,9 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "install",
+      "output": "install.out"
+    }
+  ]
+}
diff --git a/tests/specs/install/installs_all_workspace_imports/deno.json b/tests/specs/install/installs_all_workspace_imports/deno.json
new file mode 100644
index 0000000000..ac77e26d9b
--- /dev/null
+++ b/tests/specs/install/installs_all_workspace_imports/deno.json
@@ -0,0 +1,6 @@
+{
+  "workspace": ["packages/foo", "packages/bar"],
+  "imports": {
+    "@denotest/subtract": "jsr:@denotest/subtract@^1.0.0"
+  }
+}
diff --git a/tests/specs/install/installs_all_workspace_imports/install.out b/tests/specs/install/installs_all_workspace_imports/install.out
new file mode 100644
index 0000000000..b02e6cc033
--- /dev/null
+++ b/tests/specs/install/installs_all_workspace_imports/install.out
@@ -0,0 +1,10 @@
+[UNORDERED_START]
+Download http://localhost:4260/@denotest%2fesm-basic
+Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
+Download http://127.0.0.1:4250/@denotest/subtract/meta.json
+Download http://127.0.0.1:4250/@denotest/add/meta.json
+Download http://127.0.0.1:4250/@denotest/add/1.0.0_meta.json
+Download http://127.0.0.1:4250/@denotest/subtract/1.0.0_meta.json
+Download http://127.0.0.1:4250/@denotest/add/1.0.0/mod.ts
+Download http://127.0.0.1:4250/@denotest/subtract/1.0.0/mod.ts
+[UNORDERED_END]
diff --git a/tests/specs/install/installs_all_workspace_imports/packages/bar/deno.json b/tests/specs/install/installs_all_workspace_imports/packages/bar/deno.json
new file mode 100644
index 0000000000..0172071c39
--- /dev/null
+++ b/tests/specs/install/installs_all_workspace_imports/packages/bar/deno.json
@@ -0,0 +1,5 @@
+{
+  "imports": {
+    "@denotest/esm-basic": "npm:@denotest/esm-basic@^1.0.0"
+  }
+}
diff --git a/tests/specs/install/installs_all_workspace_imports/packages/foo/deno.json b/tests/specs/install/installs_all_workspace_imports/packages/foo/deno.json
new file mode 100644
index 0000000000..38ca2d4b85
--- /dev/null
+++ b/tests/specs/install/installs_all_workspace_imports/packages/foo/deno.json
@@ -0,0 +1,5 @@
+{
+  "imports": {
+    "@denotest/add": "jsr:@denotest/add@^1.0.0"
+  }
+}
diff --git a/tests/specs/install/invalid_scheme/__test__.jsonc b/tests/specs/install/invalid_scheme/__test__.jsonc
new file mode 100644
index 0000000000..c4d3ebbf06
--- /dev/null
+++ b/tests/specs/install/invalid_scheme/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "tempDir": true,
+  "args": "install",
+  "output": "install.out"
+}
diff --git a/tests/specs/install/invalid_scheme/install.out b/tests/specs/install/invalid_scheme/install.out
new file mode 100644
index 0000000000..cf100216bd
--- /dev/null
+++ b/tests/specs/install/invalid_scheme/install.out
@@ -0,0 +1,5 @@
+Warning Not implemented scheme 'git'
+    at file:///[WILDLINE]/package.json
+Download http://localhost:4260/@denotest%2fadd
+Download http://localhost:4260/@denotest/add/1.0.0.tgz
+Initialize @denotest/add@1.0.0
diff --git a/tests/specs/install/invalid_scheme/package.json b/tests/specs/install/invalid_scheme/package.json
new file mode 100644
index 0000000000..5e50ae591d
--- /dev/null
+++ b/tests/specs/install/invalid_scheme/package.json
@@ -0,0 +1,6 @@
+{
+  "dependencies": {
+    "@denotest/add": "*",
+    "deno": "git:denoland/deno"
+  }
+}
diff --git a/tests/specs/install/jsr_exports/__test__.jsonc b/tests/specs/install/jsr_exports/__test__.jsonc
new file mode 100644
index 0000000000..7ccc5da4d9
--- /dev/null
+++ b/tests/specs/install/jsr_exports/__test__.jsonc
@@ -0,0 +1,7 @@
+{
+  "tempDir": true,
+  "steps": [
+    { "args": "install", "output": "install.out" },
+    { "args": "run --cached-only main.ts", "output": "main.out" }
+  ]
+}
diff --git a/tests/specs/install/jsr_exports/deno.json b/tests/specs/install/jsr_exports/deno.json
new file mode 100644
index 0000000000..4b281f80ae
--- /dev/null
+++ b/tests/specs/install/jsr_exports/deno.json
@@ -0,0 +1,5 @@
+{
+  "imports": {
+    "@denotest/multiple-exports": "jsr:@denotest/multiple-exports@^1.0.0"
+  }
+}
diff --git a/tests/specs/install/jsr_exports/install.out b/tests/specs/install/jsr_exports/install.out
new file mode 100644
index 0000000000..bce0d79bb3
--- /dev/null
+++ b/tests/specs/install/jsr_exports/install.out
@@ -0,0 +1,13 @@
+[UNORDERED_START]
+Download http://127.0.0.1:4250/@denotest/multiple-exports/meta.json
+Download http://127.0.0.1:4250/@denotest/multiple-exports/1.0.0_meta.json
+Download http://127.0.0.1:4250/@denotest/multiple-exports/1.0.0/add.ts
+Download http://127.0.0.1:4250/@denotest/multiple-exports/1.0.0/subtract.ts
+Download http://127.0.0.1:4250/@denotest/multiple-exports/1.0.0/data.json
+Download http://127.0.0.1:4250/@denotest/add/meta.json
+Download http://127.0.0.1:4250/@denotest/subtract/meta.json
+Download http://127.0.0.1:4250/@denotest/add/1.0.0_meta.json
+Download http://127.0.0.1:4250/@denotest/subtract/1.0.0_meta.json
+Download http://127.0.0.1:4250/@denotest/add/1.0.0/mod.ts
+Download http://127.0.0.1:4250/@denotest/subtract/1.0.0/mod.ts
+[UNORDERED_END]
diff --git a/tests/specs/install/jsr_exports/main.out b/tests/specs/install/jsr_exports/main.out
new file mode 100644
index 0000000000..6ce184bada
--- /dev/null
+++ b/tests/specs/install/jsr_exports/main.out
@@ -0,0 +1,3 @@
+3
+-1
+{ a: 1 }
diff --git a/tests/specs/install/jsr_exports/main.ts b/tests/specs/install/jsr_exports/main.ts
new file mode 100644
index 0000000000..f7efdb0e98
--- /dev/null
+++ b/tests/specs/install/jsr_exports/main.ts
@@ -0,0 +1,7 @@
+import { add } from "@denotest/multiple-exports/add";
+import { subtract } from "@denotest/multiple-exports/subtract";
+import data from "@denotest/multiple-exports/data-json" with { type: "json" };
+
+console.log(add(1, 2));
+console.log(subtract(1, 2));
+console.log(data);
diff --git a/tests/specs/install/non_existent_optional_peer/install.out b/tests/specs/install/non_existent_optional_peer/install.out
index 292c1a4e2f..694d4b51b8 100644
--- a/tests/specs/install/non_existent_optional_peer/install.out
+++ b/tests/specs/install/non_existent_optional_peer/install.out
@@ -1,5 +1,5 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/non-existent-optional-peer
+Download http://localhost:4260/@denotest%2fnon-existent-optional-peer
 Download http://localhost:4260/uWebSockets.js
 Download http://localhost:4260/@denotest/non-existent-optional-peer/1.0.0.tgz
 [UNORDERED_END]
diff --git a/tests/specs/install/scripts_install_launch_cjs_temp_dir/__test__.jsonc b/tests/specs/install/scripts_install_launch_cjs_temp_dir/__test__.jsonc
new file mode 100644
index 0000000000..087d08eff0
--- /dev/null
+++ b/tests/specs/install/scripts_install_launch_cjs_temp_dir/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "tempDir": true,
+  "args": "install --allow-scripts",
+  "output": "output.out"
+}
diff --git a/tests/specs/install/scripts_install_launch_cjs_temp_dir/output.out b/tests/specs/install/scripts_install_launch_cjs_temp_dir/output.out
new file mode 100644
index 0000000000..d5f06cc6ea
--- /dev/null
+++ b/tests/specs/install/scripts_install_launch_cjs_temp_dir/output.out
@@ -0,0 +1,4 @@
+Download http://localhost:4260/@denotest%2finstall-launch-cjs-temp-dir
+Download http://localhost:4260/@denotest/install-launch-cjs-temp-dir/1.0.0.tgz
+Initialize @denotest/install-launch-cjs-temp-dir@1.0.0
+Initialize @denotest/install-launch-cjs-temp-dir@1.0.0: running 'install' script
diff --git a/tests/specs/install/scripts_install_launch_cjs_temp_dir/package.json b/tests/specs/install/scripts_install_launch_cjs_temp_dir/package.json
new file mode 100644
index 0000000000..71672f9bc1
--- /dev/null
+++ b/tests/specs/install/scripts_install_launch_cjs_temp_dir/package.json
@@ -0,0 +1,5 @@
+{
+  "dependencies": {
+    "@denotest/install-launch-cjs-temp-dir": "*"
+  }
+}
diff --git a/tests/specs/install/scripts_install_no_ext/__test__.jsonc b/tests/specs/install/scripts_install_no_ext/__test__.jsonc
new file mode 100644
index 0000000000..087d08eff0
--- /dev/null
+++ b/tests/specs/install/scripts_install_no_ext/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "tempDir": true,
+  "args": "install --allow-scripts",
+  "output": "output.out"
+}
diff --git a/tests/specs/install/scripts_install_no_ext/output.out b/tests/specs/install/scripts_install_no_ext/output.out
new file mode 100644
index 0000000000..074e978121
--- /dev/null
+++ b/tests/specs/install/scripts_install_no_ext/output.out
@@ -0,0 +1,4 @@
+Download http://localhost:4260/@denotest%2finstall-no-ext
+Download http://localhost:4260/@denotest/install-no-ext/1.0.0.tgz
+Initialize @denotest/install-no-ext@1.0.0
+Initialize @denotest/install-no-ext@1.0.0: running 'install' script
diff --git a/tests/specs/install/scripts_install_no_ext/package.json b/tests/specs/install/scripts_install_no_ext/package.json
new file mode 100644
index 0000000000..7ac9ca6b29
--- /dev/null
+++ b/tests/specs/install/scripts_install_no_ext/package.json
@@ -0,0 +1,5 @@
+{
+  "dependencies": {
+    "@denotest/install-no-ext": "*"
+  }
+}
diff --git a/tests/specs/install/type_only_import/__test__.jsonc b/tests/specs/install/type_only_import/__test__.jsonc
new file mode 100644
index 0000000000..22b8134ac3
--- /dev/null
+++ b/tests/specs/install/type_only_import/__test__.jsonc
@@ -0,0 +1,10 @@
+{
+  "tempDir": true,
+  "steps": [
+    { "args": "install -e main.ts", "output": "install.out" },
+    {
+      "args": "run --check --cached-only main.ts",
+      "output": "run.out"
+    }
+  ]
+}
diff --git a/tests/specs/install/type_only_import/install.out b/tests/specs/install/type_only_import/install.out
new file mode 100644
index 0000000000..1bdbec4e58
--- /dev/null
+++ b/tests/specs/install/type_only_import/install.out
@@ -0,0 +1,6 @@
+Download http://127.0.0.1:4250/@denotest/type-only-import/meta.json
+Download http://127.0.0.1:4250/@denotest/type-only-import/1.0.0_meta.json
+[UNORDERED_START]
+Download http://127.0.0.1:4250/@denotest/type-only-import/1.0.0/mod.ts
+Download http://127.0.0.1:4250/@denotest/type-only-import/1.0.0/foo.ts
+[UNORDERED_END]
diff --git a/tests/specs/install/type_only_import/main.ts b/tests/specs/install/type_only_import/main.ts
new file mode 100644
index 0000000000..bf22935a2d
--- /dev/null
+++ b/tests/specs/install/type_only_import/main.ts
@@ -0,0 +1,3 @@
+import { foo } from "jsr:@denotest/type-only-import";
+
+console.log(foo.bar);
diff --git a/tests/specs/install/type_only_import/run.out b/tests/specs/install/type_only_import/run.out
new file mode 100644
index 0000000000..d36ac8aa37
--- /dev/null
+++ b/tests/specs/install/type_only_import/run.out
@@ -0,0 +1,2 @@
+Check [WILDCARD]main.ts
+foo
diff --git a/tests/specs/install/workspace_member_with_tag_dep/__test__.jsonc b/tests/specs/install/workspace_member_with_tag_dep/__test__.jsonc
new file mode 100644
index 0000000000..254fe8b989
--- /dev/null
+++ b/tests/specs/install/workspace_member_with_tag_dep/__test__.jsonc
@@ -0,0 +1,9 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "install",
+      "output": "install.out"
+    }
+  ]
+}
diff --git a/tests/specs/install/workspace_member_with_tag_dep/install.out b/tests/specs/install/workspace_member_with_tag_dep/install.out
new file mode 100644
index 0000000000..8f03ba6407
--- /dev/null
+++ b/tests/specs/install/workspace_member_with_tag_dep/install.out
@@ -0,0 +1,3 @@
+Download http://localhost:4260/@denotest%2fesm-basic
+Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
+Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/install/workspace_member_with_tag_dep/package.json b/tests/specs/install/workspace_member_with_tag_dep/package.json
new file mode 100644
index 0000000000..58aa5d5cc6
--- /dev/null
+++ b/tests/specs/install/workspace_member_with_tag_dep/package.json
@@ -0,0 +1,6 @@
+{
+  "dependencies": {
+    "@denotest/esm-basic": "latest"
+  },
+  "workspaces": ["package1"]
+}
diff --git a/tests/specs/install/workspace_member_with_tag_dep/package1/package.json b/tests/specs/install/workspace_member_with_tag_dep/package1/package.json
new file mode 100644
index 0000000000..150a7df6af
--- /dev/null
+++ b/tests/specs/install/workspace_member_with_tag_dep/package1/package.json
@@ -0,0 +1,5 @@
+{
+  "dependencies": {
+    "@denotest/esm-basic": "latest"
+  }
+}
diff --git a/tests/specs/jsr/module_graph/main.out b/tests/specs/jsr/module_graph/main.out
index 35905a63a2..d17238a9c2 100644
--- a/tests/specs/jsr/module_graph/main.out
+++ b/tests/specs/jsr/module_graph/main.out
@@ -1,4 +1,4 @@
-[WILDCARD]Caching module info for http://127.0.0.1:4250/@denotest/module-graph/1.4.0/mod.ts
+[WILDCARD]Caching module info for http://127.0.0.1:4250/@denotest/module-graph/1.4.0/other.ts
 [WILDCARD]
 Test { other: Other {} }
 [WILDCARD]
diff --git a/tests/specs/jsr/module_graph2/main.out b/tests/specs/jsr/module_graph2/main.out
index ba2c06aaa4..fca91e2399 100644
--- a/tests/specs/jsr/module_graph2/main.out
+++ b/tests/specs/jsr/module_graph2/main.out
@@ -1,4 +1,4 @@
-[WILDCARD]Caching module info for http://127.0.0.1:4250/@denotest/module-graph2/1.4.0/mod.ts
+[WILDCARD]Caching module info for http://127.0.0.1:4250/@denotest/module-graph2/1.4.0/other.ts
 [WILDCARD]
 Test { other: Other {} }
 [WILDCARD]
diff --git a/tests/specs/lint/node_globals_no_duplicate_imports/main.out b/tests/specs/lint/node_globals_no_duplicate_imports/main.out
index 56df10eba4..ce5523f99c 100644
--- a/tests/specs/lint/node_globals_no_duplicate_imports/main.out
+++ b/tests/specs/lint/node_globals_no_duplicate_imports/main.out
@@ -2,3 +2,7 @@ error: Uncaught (in promise) ReferenceError: setImmediate is not defined
 const _foo = setImmediate;
              ^
     at [WILDCARD]main.ts:3:14
+
+    info: setImmediate is not available in the global scope in Deno.
+    hint: Import it explicitly with import { setImmediate } from "node:timers";,
+          or run again with --unstable-node-globals flag to add this global.
diff --git a/tests/specs/lockfile/frozen_lockfile/__test__.jsonc b/tests/specs/lockfile/frozen_lockfile/__test__.jsonc
index 8179052e19..07ec2c4c14 100644
--- a/tests/specs/lockfile/frozen_lockfile/__test__.jsonc
+++ b/tests/specs/lockfile/frozen_lockfile/__test__.jsonc
@@ -118,7 +118,6 @@
         }
       ]
     },
-
     "lockfile_config": {
       "steps": [
         {
@@ -146,7 +145,6 @@
         }
       ]
     },
-
     "non_analyzable_dynamic_npm": {
       "steps": [
         {
@@ -185,6 +183,19 @@
           "exitCode": 1
         }
       ]
+    },
+    "check_subcommand": {
+      "steps": [
+        {
+          "args": "check --frozen=true add.ts",
+          "output": "[WILDCARD]The lockfile is out of date[WILDCARD]",
+          "exitCode": 1
+        },
+        {
+          "args": "check --frozen=false add.ts",
+          "output": "[WILDCARD]Check [WILDCARD]add.ts\n"
+        }
+      ]
     }
   }
 }
diff --git a/tests/specs/lockfile/frozen_lockfile/frozen_new_dep_dynamic_npm.out b/tests/specs/lockfile/frozen_lockfile/frozen_new_dep_dynamic_npm.out
index 4ae4d059cc..4fc016c57c 100644
--- a/tests/specs/lockfile/frozen_lockfile/frozen_new_dep_dynamic_npm.out
+++ b/tests/specs/lockfile/frozen_lockfile/frozen_new_dep_dynamic_npm.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/subtract
+Download http://localhost:4260/@denotest%2fsubtract
 error: Uncaught (in promise) TypeError: The lockfile is out of date. Run `deno install --frozen=false`, or rerun with `--frozen=false` to update it.
 changes:
  4 | -    "npm:@denotest/add@1": "1.0.0"
diff --git a/tests/specs/lockfile/frozen_lockfile/frozen_new_dep_run.out b/tests/specs/lockfile/frozen_lockfile/frozen_new_dep_run.out
index 057b9632b3..07b37b925a 100644
--- a/tests/specs/lockfile/frozen_lockfile/frozen_new_dep_run.out
+++ b/tests/specs/lockfile/frozen_lockfile/frozen_new_dep_run.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/subtract
+Download http://localhost:4260/@denotest%2fsubtract
 error: The lockfile is out of date. Run `deno install --frozen=false`, or rerun with `--frozen=false` to update it.
 changes:
  4 | -    "npm:@denotest/add@1": "1.0.0"
diff --git a/tests/specs/lockfile/frozen_lockfile/frozen_package_json_changed.out b/tests/specs/lockfile/frozen_lockfile/frozen_package_json_changed.out
index dc31a1a653..626007478f 100644
--- a/tests/specs/lockfile/frozen_lockfile/frozen_package_json_changed.out
+++ b/tests/specs/lockfile/frozen_lockfile/frozen_package_json_changed.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fbin
 error: The lockfile is out of date. Run `deno install --frozen=false`, or rerun with `--frozen=false` to update it.
 changes:
  4 | -    "npm:@denotest/add@1": "1.0.0"
diff --git a/tests/specs/lockfile/frozen_lockfile/no_lockfile_run.out b/tests/specs/lockfile/frozen_lockfile/no_lockfile_run.out
index 27dc66fd2f..047bfdb4ac 100644
--- a/tests/specs/lockfile/frozen_lockfile/no_lockfile_run.out
+++ b/tests/specs/lockfile/frozen_lockfile/no_lockfile_run.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/add
+Download http://localhost:4260/@denotest%2fadd
 error: The lockfile is out of date. Run `deno install --frozen=false`, or rerun with `--frozen=false` to update it.
 changes:
  1 | -
diff --git a/tests/specs/lockfile/only_package_json/install.out b/tests/specs/lockfile/only_package_json/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/lockfile/only_package_json/install.out
+++ b/tests/specs/lockfile/only_package_json/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/mod.rs b/tests/specs/mod.rs
index 34221dd9da..b4c8781d31 100644
--- a/tests/specs/mod.rs
+++ b/tests/specs/mod.rs
@@ -119,6 +119,9 @@ struct MultiStepMetaData {
   /// steps.
   #[serde(default)]
   pub temp_dir: bool,
+  /// Whether the temporary directory should be symlinked to another path.
+  #[serde(default)]
+  pub symlinked_temp_dir: bool,
   /// The base environment to use for the test.
   #[serde(default)]
   pub base: Option<String>,
@@ -142,6 +145,8 @@ struct SingleTestMetaData {
   #[serde(default)]
   pub temp_dir: bool,
   #[serde(default)]
+  pub symlinked_temp_dir: bool,
+  #[serde(default)]
   pub repeat: Option<usize>,
   #[serde(flatten)]
   pub step: StepMetaData,
@@ -155,6 +160,7 @@ impl SingleTestMetaData {
       base: self.base,
       cwd: None,
       temp_dir: self.temp_dir,
+      symlinked_temp_dir: self.symlinked_temp_dir,
       repeat: self.repeat,
       envs: Default::default(),
       steps: vec![self.step],
@@ -330,6 +336,20 @@ fn test_context_from_metadata(
     builder = builder.cwd(cwd.to_string_lossy());
   }
 
+  if metadata.symlinked_temp_dir {
+    // not actually deprecated, we just want to discourage its use
+    // because it's mostly used for testing purposes locally
+    #[allow(deprecated)]
+    {
+      builder = builder.use_symlinked_temp_dir();
+    }
+    if cfg!(not(debug_assertions)) {
+      // panic to prevent using this on the CI as CI already uses
+      // a symlinked temp directory for every test
+      panic!("Cannot use symlinkedTempDir in release mode");
+    }
+  }
+
   match &metadata.base {
     // todo(dsherret): add bases in the future as needed
     Some(base) => panic!("Unknown test base: {}", base),
diff --git a/tests/specs/node/child_process_extra_pipes/main.out b/tests/specs/node/child_process_extra_pipes/main.out
index 694126b924..436afd2f75 100644
--- a/tests/specs/node/child_process_extra_pipes/main.out
+++ b/tests/specs/node/child_process_extra_pipes/main.out
@@ -1,5 +1,5 @@
-data: hello world
 [UNORDERED_START]
 child closed
+got: hello world
 pipe closed
 [UNORDERED_END]
diff --git a/tests/specs/node/child_process_extra_pipes/main.ts b/tests/specs/node/child_process_extra_pipes/main.ts
index a3683fe9ee..2837cdc53c 100644
--- a/tests/specs/node/child_process_extra_pipes/main.ts
+++ b/tests/specs/node/child_process_extra_pipes/main.ts
@@ -1,5 +1,4 @@
 import child_process from "node:child_process";
-import { Buffer } from "node:buffer";
 import console from "node:console";
 
 const child = child_process.spawn("./test-pipe/target/debug/test-pipe", [], {
@@ -8,19 +7,32 @@ const child = child_process.spawn("./test-pipe/target/debug/test-pipe", [], {
 
 const extra = child.stdio[4];
 
-const p = Promise.withResolvers();
+if (!extra) {
+  throw new Error("no extra pipe");
+}
+
+const p = Promise.withResolvers<void>();
+
+let got = "";
 
 child.on("close", () => {
   console.log("child closed");
-  p.resolve();
+  console.log("got:", got);
+  if (got === "hello world") {
+    p.resolve();
+  } else {
+    p.reject(new Error(`wanted "hello world", got "${got}"`));
+  }
 });
 
 extra.on("data", (d) => {
-  console.log("data:", d.toString().trim());
+  got += d.toString();
 });
 
 extra.on("close", () => {
   console.log("pipe closed");
 });
 
+extra.write("start");
+
 await p.promise;
diff --git a/tests/specs/node/child_process_extra_pipes/test-pipe/src/main.rs b/tests/specs/node/child_process_extra_pipes/test-pipe/src/main.rs
index 192f827313..acc034830f 100644
--- a/tests/specs/node/child_process_extra_pipes/test-pipe/src/main.rs
+++ b/tests/specs/node/child_process_extra_pipes/test-pipe/src/main.rs
@@ -1,12 +1,31 @@
+use std::fs::File;
 use std::io::prelude::*;
 use std::os::fd::FromRawFd;
-use std::os::unix::net::UnixStream;
 
 fn main() {
   #[cfg(unix)]
   {
-    let mut stream = unsafe { UnixStream::from_raw_fd(4) };
+    let mut pipe = unsafe { File::from_raw_fd(4) };
 
-    stream.write_all(b"hello world\n").unwrap();
+    let mut read = 0;
+    let mut buf = [0u8; 1024];
+    loop {
+      if read > 4 {
+        assert_eq!(&buf[..5], b"start");
+        break;
+      }
+      match pipe.read(&mut buf) {
+        Ok(n) => {
+          read += n;
+        }
+        Ok(0) => {
+          return;
+        }
+        Err(e) => {
+          eprintln!("GOT ERROR: {e:?}");
+        }
+      }
+    }
+    pipe.write_all(b"hello world").unwrap();
   }
 }
diff --git a/tests/specs/node/cjs_reexport_same_specifier_in_sub_folder/main.out b/tests/specs/node/cjs_reexport_same_specifier_in_sub_folder/main.out
index 321d995b8a..c50f064d7f 100644
--- a/tests/specs/node/cjs_reexport_same_specifier_in_sub_folder/main.out
+++ b/tests/specs/node/cjs_reexport_same_specifier_in_sub_folder/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/cjs-reexport-same-specifier-in-sub-folder
+Download http://localhost:4260/@denotest%2fcjs-reexport-same-specifier-in-sub-folder
 Download http://localhost:4260/@denotest/cjs-reexport-same-specifier-in-sub-folder/1.0.0.tgz
 [Module: null prototype] {
   default: { main: [Getter], sub: [Getter] },
diff --git a/tests/specs/node/next_tick_uncaught_exception/__test__.jsonc b/tests/specs/node/next_tick_uncaught_exception/__test__.jsonc
new file mode 100644
index 0000000000..5517e693d6
--- /dev/null
+++ b/tests/specs/node/next_tick_uncaught_exception/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run main.ts",
+  "output": "main.out"
+}
diff --git a/tests/specs/node/next_tick_uncaught_exception/main.out b/tests/specs/node/next_tick_uncaught_exception/main.out
new file mode 100644
index 0000000000..45b756515b
--- /dev/null
+++ b/tests/specs/node/next_tick_uncaught_exception/main.out
@@ -0,0 +1,2 @@
+caught Error: thrown from next tick
+    at file:///[WILDCARD]/specs/node/next_tick_uncaught_exception/main.ts:4:15
diff --git a/tests/specs/node/next_tick_uncaught_exception/main.ts b/tests/specs/node/next_tick_uncaught_exception/main.ts
new file mode 100644
index 0000000000..2679d3d54b
--- /dev/null
+++ b/tests/specs/node/next_tick_uncaught_exception/main.ts
@@ -0,0 +1,13 @@
+import process from "node:process";
+import { strictEqual } from "node:assert";
+
+const error = new Error("thrown from next tick");
+
+process.on("uncaughtException", (caught) => {
+  strictEqual(caught, error);
+  console.log("caught", caught);
+});
+
+process.nextTick(() => {
+  throw error;
+});
diff --git a/tests/specs/node/node_test_module/__test__.jsonc b/tests/specs/node/node_test_module/__test__.jsonc
index ef93b66731..701917bf35 100644
--- a/tests/specs/node/node_test_module/__test__.jsonc
+++ b/tests/specs/node/node_test_module/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "test test.js",
   "output": "test.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/node/node_test_module_no_sanitizers/__test__.jsonc b/tests/specs/node/node_test_module_no_sanitizers/__test__.jsonc
index 0a9a9524b4..8830e48dde 100644
--- a/tests/specs/node/node_test_module_no_sanitizers/__test__.jsonc
+++ b/tests/specs/node/node_test_module_no_sanitizers/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "test -A --no-check test_no_sanitizers/test.js",
   "output": "test_no_sanitizers/test.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/node/require_export_from_parent_with_no_filename/__test__.jsonc b/tests/specs/node/require_export_from_parent_with_no_filename/__test__.jsonc
new file mode 100644
index 0000000000..a3de08e460
--- /dev/null
+++ b/tests/specs/node/require_export_from_parent_with_no_filename/__test__.jsonc
@@ -0,0 +1,13 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "install",
+      "output": "[WILDCARD]"
+    },
+    {
+      "args": "run -A main.cjs",
+      "output": "3\n"
+    }
+  ]
+}
diff --git a/tests/specs/node/require_export_from_parent_with_no_filename/main.cjs b/tests/specs/node/require_export_from_parent_with_no_filename/main.cjs
new file mode 100644
index 0000000000..3335ae1bf9
--- /dev/null
+++ b/tests/specs/node/require_export_from_parent_with_no_filename/main.cjs
@@ -0,0 +1,16 @@
+const path = require("node:path");
+const Module = require("node:module");
+function requireFromString(code, filename) {
+  const paths = Module._nodeModulePaths((0, path.dirname)(filename));
+  const m = new Module(filename, module.parent);
+  m.paths = paths;
+  m._compile(code, filename);
+  return m.exports;
+}
+
+const code = `
+const add = require("@denotest/cjs-multiple-exports/add");
+
+console.log(add(1, 2));
+`;
+requireFromString(code, "fake.js");
diff --git a/tests/specs/node/require_export_from_parent_with_no_filename/package.json b/tests/specs/node/require_export_from_parent_with_no_filename/package.json
new file mode 100644
index 0000000000..9cd6438953
--- /dev/null
+++ b/tests/specs/node/require_export_from_parent_with_no_filename/package.json
@@ -0,0 +1,5 @@
+{
+  "dependencies": {
+    "@denotest/cjs-multiple-exports": "1.0.0"
+  }
+}
diff --git a/tests/specs/npm/adding_npm_dep_in_dynamic_import/main.out b/tests/specs/npm/adding_npm_dep_in_dynamic_import/main.out
index fe612aa3c1..44c76f28d1 100644
--- a/tests/specs/npm/adding_npm_dep_in_dynamic_import/main.out
+++ b/tests/specs/npm/adding_npm_dep_in_dynamic_import/main.out
@@ -1,8 +1,8 @@
-Download http://localhost:4260/@denotest/add
+Download http://localhost:4260/@denotest%2fadd
 Download http://localhost:4260/@denotest/add/1.0.0.tgz
 Initialize @denotest/add@1.0.0
 3
-Download http://localhost:4260/@denotest/subtract
+Download http://localhost:4260/@denotest%2fsubtract
 Download http://localhost:4260/@denotest/subtract/1.0.0.tgz
 Initialize @denotest/subtract@1.0.0
 1
diff --git a/tests/specs/npm/bin_entries_prefer_closer/install.out b/tests/specs/npm/bin_entries_prefer_closer/install.out
index 1d3a995b80..1c9472f46f 100644
--- a/tests/specs/npm/bin_entries_prefer_closer/install.out
+++ b/tests/specs/npm/bin_entries_prefer_closer/install.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/transitive-bin
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2ftransitive-bin
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Download http://localhost:4260/@denotest/transitive-bin/1.0.0.tgz
 Download http://localhost:4260/@denotest/bin/0.7.0.tgz
diff --git a/tests/specs/npm/bin_entry_created_by_lifecycle/__test__.jsonc b/tests/specs/npm/bin_entry_created_by_lifecycle/__test__.jsonc
new file mode 100644
index 0000000000..665aec823d
--- /dev/null
+++ b/tests/specs/npm/bin_entry_created_by_lifecycle/__test__.jsonc
@@ -0,0 +1,29 @@
+{
+  "tempDir": true,
+  "tests": {
+    "all_at_once": {
+      "steps": [
+        {
+          "args": "install --allow-scripts",
+          "output": "all_at_once_install.out"
+        },
+        { "args": "task run-testbin", "output": "run_testbin.out" }
+      ]
+    },
+    "separate_steps": {
+      "steps": [
+        { "if": "unix", "args": "install", "output": "install_warn.out" },
+        {
+          "if": "windows",
+          "args": "install",
+          "output": "install_warn_windows.out"
+        },
+        {
+          "args": "install --allow-scripts",
+          "output": "Initialize @denotest/bin-created-by-lifecycle@1.0.0: running 'install' script\n"
+        },
+        { "args": "task run-testbin", "output": "run_testbin.out" }
+      ]
+    }
+  }
+}
diff --git a/tests/specs/npm/bin_entry_created_by_lifecycle/all_at_once_install.out b/tests/specs/npm/bin_entry_created_by_lifecycle/all_at_once_install.out
new file mode 100644
index 0000000000..bfaba3caf2
--- /dev/null
+++ b/tests/specs/npm/bin_entry_created_by_lifecycle/all_at_once_install.out
@@ -0,0 +1,4 @@
+Download http://localhost:4260/@denotest%2fbin-created-by-lifecycle
+Download http://localhost:4260/@denotest/bin-created-by-lifecycle/1.0.0.tgz
+Initialize @denotest/bin-created-by-lifecycle@1.0.0
+Initialize @denotest/bin-created-by-lifecycle@1.0.0: running 'install' script
diff --git a/tests/specs/npm/bin_entry_created_by_lifecycle/install_warn.out b/tests/specs/npm/bin_entry_created_by_lifecycle/install_warn.out
new file mode 100644
index 0000000000..864a3f6f51
--- /dev/null
+++ b/tests/specs/npm/bin_entry_created_by_lifecycle/install_warn.out
@@ -0,0 +1,10 @@
+Download http://localhost:4260/@denotest%2fbin-created-by-lifecycle
+Download http://localhost:4260/@denotest/bin-created-by-lifecycle/1.0.0.tgz
+Initialize @denotest/bin-created-by-lifecycle@1.0.0
+Warning Trying to set up 'testbin' bin for "[WILDCARD]bin-created-by-lifecycle", but the entry point "[WILDCARD]testbin.js" doesn't exist.
+Warning The following packages contained npm lifecycle scripts (preinstall/install/postinstall) that were not executed:
+┠─ npm:@denotest/bin-created-by-lifecycle@1.0.0
+┃
+┠─ This may cause the packages to not work correctly.
+┖─ To run lifecycle scripts, use the `--allow-scripts` flag with `deno install`:
+   deno install --allow-scripts=npm:@denotest/bin-created-by-lifecycle@1.0.0
diff --git a/tests/specs/npm/bin_entry_created_by_lifecycle/install_warn_windows.out b/tests/specs/npm/bin_entry_created_by_lifecycle/install_warn_windows.out
new file mode 100644
index 0000000000..6838088735
--- /dev/null
+++ b/tests/specs/npm/bin_entry_created_by_lifecycle/install_warn_windows.out
@@ -0,0 +1,9 @@
+Download http://localhost:4260/@denotest%2fbin-created-by-lifecycle
+Download http://localhost:4260/@denotest/bin-created-by-lifecycle/1.0.0.tgz
+Initialize @denotest/bin-created-by-lifecycle@1.0.0
+Warning The following packages contained npm lifecycle scripts (preinstall/install/postinstall) that were not executed:
+┠─ npm:@denotest/bin-created-by-lifecycle@1.0.0
+┃
+┠─ This may cause the packages to not work correctly.
+┖─ To run lifecycle scripts, use the `--allow-scripts` flag with `deno install`:
+   deno install --allow-scripts=npm:@denotest/bin-created-by-lifecycle@1.0.0
diff --git a/tests/specs/npm/bin_entry_created_by_lifecycle/package.json b/tests/specs/npm/bin_entry_created_by_lifecycle/package.json
new file mode 100644
index 0000000000..9a8941ed9c
--- /dev/null
+++ b/tests/specs/npm/bin_entry_created_by_lifecycle/package.json
@@ -0,0 +1,8 @@
+{
+  "dependencies": {
+    "@denotest/bin-created-by-lifecycle": "1.0.0"
+  },
+  "scripts": {
+    "run-testbin": "testbin"
+  }
+}
diff --git a/tests/specs/npm/bin_entry_created_by_lifecycle/run_testbin.out b/tests/specs/npm/bin_entry_created_by_lifecycle/run_testbin.out
new file mode 100644
index 0000000000..a03f8bc58e
--- /dev/null
+++ b/tests/specs/npm/bin_entry_created_by_lifecycle/run_testbin.out
@@ -0,0 +1,2 @@
+Task run-testbin testbin
+run testbin
diff --git a/tests/specs/npm/builtin_module_module/__test__.jsonc b/tests/specs/npm/builtin_module_module/__test__.jsonc
index 2f26a95d4a..eb211eda16 100644
--- a/tests/specs/npm/builtin_module_module/__test__.jsonc
+++ b/tests/specs/npm/builtin_module_module/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run --allow-read --quiet builtin_module_module/main.js",
-  "output": "builtin_module_module/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "builtin_module_module/main.out"
 }
diff --git a/tests/specs/npm/byonm_run_npm/__test__.jsonc b/tests/specs/npm/byonm_run_npm/__test__.jsonc
new file mode 100644
index 0000000000..4f0b21b0ff
--- /dev/null
+++ b/tests/specs/npm/byonm_run_npm/__test__.jsonc
@@ -0,0 +1,30 @@
+{
+  "tests": {
+    "not_in_deps": {
+      "steps": [{
+        "args": "run -A --quiet npm:cowsay moo",
+        "output": "not_in_deps.out"
+      }, {
+        // ensure it doesn't make any lockfile modifications and thus doesn't write to the lockfile
+        "args": [
+          "eval",
+          "try { Deno.statSync('deno.lock') } catch (e) { console.log(e instanceof Deno.errors.NotFound); }"
+        ],
+        "output": "true\n"
+      }]
+    },
+    "in_deps": {
+      "tempDir": true,
+      "steps": [{
+        "args": "install npm:cowsay",
+        "output": "[WILDCARD]"
+      }, {
+        "args": "run --allow-write overwrite.ts",
+        "output": "[WILDCARD]"
+      }, {
+        "args": "run -A npm:cowsay moo",
+        "output": "replaced\n"
+      }]
+    }
+  }
+}
diff --git a/tests/specs/npm/byonm_run_npm/deno.json b/tests/specs/npm/byonm_run_npm/deno.json
new file mode 100644
index 0000000000..2c63c08510
--- /dev/null
+++ b/tests/specs/npm/byonm_run_npm/deno.json
@@ -0,0 +1,2 @@
+{
+}
diff --git a/tests/specs/npm/byonm_run_npm/not_in_deps.out b/tests/specs/npm/byonm_run_npm/not_in_deps.out
new file mode 100644
index 0000000000..dc07eb43ee
--- /dev/null
+++ b/tests/specs/npm/byonm_run_npm/not_in_deps.out
@@ -0,0 +1,8 @@
+ _____
+< moo >
+ -----
+        \   ^__^
+         \  (oo)\_______
+            (__)\       )\/\
+                ||----w |
+                ||     ||
diff --git a/tests/specs/npm/byonm_run_npm/overwrite.ts b/tests/specs/npm/byonm_run_npm/overwrite.ts
new file mode 100644
index 0000000000..3749c5e4e8
--- /dev/null
+++ b/tests/specs/npm/byonm_run_npm/overwrite.ts
@@ -0,0 +1,4 @@
+Deno.writeTextFileSync(
+  "node_modules/cowsay/cli.js",
+  "console.log('replaced');",
+);
diff --git a/tests/specs/npm/byonm_run_npm/package.json b/tests/specs/npm/byonm_run_npm/package.json
new file mode 100644
index 0000000000..9664f260a7
--- /dev/null
+++ b/tests/specs/npm/byonm_run_npm/package.json
@@ -0,0 +1,4 @@
+{
+  "dependencies": {
+  }
+}
diff --git a/tests/specs/npm/cached_only/__test__.jsonc b/tests/specs/npm/cached_only/__test__.jsonc
index 764f702d2c..b2190d110d 100644
--- a/tests/specs/npm/cached_only/__test__.jsonc
+++ b/tests/specs/npm/cached_only/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "run --cached-only cached_only/main.ts",
   "output": "cached_only/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/check_all/__test__.jsonc b/tests/specs/npm/check_all/__test__.jsonc
index 4275243056..e78f7e67d8 100644
--- a/tests/specs/npm/check_all/__test__.jsonc
+++ b/tests/specs/npm/check_all/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "check --all check_errors/main.ts",
   "output": "check_errors/main_all.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/check_all/check_errors/main_all.out b/tests/specs/npm/check_all/check_errors/main_all.out
index 4c624c0eaa..c7797e43d2 100644
--- a/tests/specs/npm/check_all/check_errors/main_all.out
+++ b/tests/specs/npm/check_all/check_errors/main_all.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/check-error
+Download http://localhost:4260/@denotest%2fcheck-error
 Download http://localhost:4260/@denotest/check-error/1.0.0.tgz
 Check file:///[WILDCARD]/check_errors/main.ts
 error: TS2506 [ERROR]: 'Class1' is referenced directly or indirectly in its own base expression.
diff --git a/tests/specs/npm/check_all/check_errors/main_local.out b/tests/specs/npm/check_all/check_errors/main_local.out
index 4d3a892e74..ac58a29c76 100644
--- a/tests/specs/npm/check_all/check_errors/main_local.out
+++ b/tests/specs/npm/check_all/check_errors/main_local.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/check-error
+Download http://localhost:4260/@denotest%2fcheck-error
 Download http://localhost:4260/@denotest/check-error/1.0.0.tgz
 Check file:///[WILDCARD]/check_errors/main.ts
 error: TS2339 [ERROR]: Property 'Asdf' does not exist on type 'typeof import("file:///[WILDCARD]/@denotest/check-error/1.0.0/index.d.ts")'.
diff --git a/tests/specs/npm/check_local/__test__.jsonc b/tests/specs/npm/check_local/__test__.jsonc
index 1bffa5eed0..2cf3ae5ef0 100644
--- a/tests/specs/npm/check_local/__test__.jsonc
+++ b/tests/specs/npm/check_local/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "check check_errors/main.ts",
   "output": "check_errors/main_local.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/check_local/check_errors/main_all.out b/tests/specs/npm/check_local/check_errors/main_all.out
index 4c624c0eaa..c7797e43d2 100644
--- a/tests/specs/npm/check_local/check_errors/main_all.out
+++ b/tests/specs/npm/check_local/check_errors/main_all.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/check-error
+Download http://localhost:4260/@denotest%2fcheck-error
 Download http://localhost:4260/@denotest/check-error/1.0.0.tgz
 Check file:///[WILDCARD]/check_errors/main.ts
 error: TS2506 [ERROR]: 'Class1' is referenced directly or indirectly in its own base expression.
diff --git a/tests/specs/npm/check_local/check_errors/main_local.out b/tests/specs/npm/check_local/check_errors/main_local.out
index 1a150b5e69..1eb8eef9fe 100644
--- a/tests/specs/npm/check_local/check_errors/main_local.out
+++ b/tests/specs/npm/check_local/check_errors/main_local.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/check-error
+Download http://localhost:4260/@denotest%2fcheck-error
 Download http://localhost:4260/@denotest/check-error/1.0.0.tgz
 Check file:///[WILDCARD]/check_errors/main.ts
 error: TS2339 [ERROR]: Property 'Asdf' does not exist on type 'typeof import("file:///[WILDCARD]/@denotest/check-error/1.0.0/index.d.ts")'.
diff --git a/tests/specs/npm/check_package_file_dts_dmts_dcts/__test__.jsonc b/tests/specs/npm/check_package_file_dts_dmts_dcts/__test__.jsonc
index 675051a69e..5caaa23aaf 100644
--- a/tests/specs/npm/check_package_file_dts_dmts_dcts/__test__.jsonc
+++ b/tests/specs/npm/check_package_file_dts_dmts_dcts/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "check file_dts_dmts_dcts/main.ts",
   "output": "file_dts_dmts_dcts/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/check_package_file_dts_dmts_dcts/file_dts_dmts_dcts/main.out b/tests/specs/npm/check_package_file_dts_dmts_dcts/file_dts_dmts_dcts/main.out
index 507d2c2f79..6ab72f53b7 100644
--- a/tests/specs/npm/check_package_file_dts_dmts_dcts/file_dts_dmts_dcts/main.out
+++ b/tests/specs/npm/check_package_file_dts_dmts_dcts/file_dts_dmts_dcts/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/file-dts-dmts-dcts
+Download http://localhost:4260/@denotest%2ffile-dts-dmts-dcts
 Download http://localhost:4260/@denotest/file-dts-dmts-dcts/1.0.0.tgz
 Check file:///[WILDCARD]/main.ts
 error: TS2322 [ERROR]: Type '5' is not assignable to type '"dts"'.
diff --git a/tests/specs/npm/check_pkg_json_import/main.out b/tests/specs/npm/check_pkg_json_import/main.out
index b60509c9a7..11f94272a5 100644
--- a/tests/specs/npm/check_pkg_json_import/main.out
+++ b/tests/specs/npm/check_pkg_json_import/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/types-pkg-json-import
+Download http://localhost:4260/@denotest%2ftypes-pkg-json-import
 Download http://localhost:4260/@denotest/types-pkg-json-import/1.0.0.tgz
 Check file:///[WILDLINE]/main.ts
diff --git a/tests/specs/npm/child_process_fork_test/__test__.jsonc b/tests/specs/npm/child_process_fork_test/__test__.jsonc
index f83cb051e1..a4bdf0c92e 100644
--- a/tests/specs/npm/child_process_fork_test/__test__.jsonc
+++ b/tests/specs/npm/child_process_fork_test/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet child_process_fork_test/main.ts",
-  "output": "child_process_fork_test/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "child_process_fork_test/main.out"
 }
diff --git a/tests/specs/npm/cjs_import_dual/check.out b/tests/specs/npm/cjs_import_dual/check.out
index be1fe86a69..c2d1daa17b 100644
--- a/tests/specs/npm/cjs_import_dual/check.out
+++ b/tests/specs/npm/cjs_import_dual/check.out
@@ -1,5 +1,5 @@
-Download http://localhost:4260/@denotest/cjs-import-dual
-Download http://localhost:4260/@denotest/dual-cjs-esm
+Download http://localhost:4260/@denotest%2fcjs-import-dual
+Download http://localhost:4260/@denotest%2fdual-cjs-esm
 Download http://localhost:4260/@denotest/cjs-import-dual/1.0.0.tgz
 Download http://localhost:4260/@denotest/dual-cjs-esm/1.0.0.tgz
 Check file:///[WILDLINE]/cjs_import_dual/main.ts
diff --git a/tests/specs/npm/cjs_import_dual/run.out b/tests/specs/npm/cjs_import_dual/run.out
index 2c05e125e1..0307bf2503 100644
--- a/tests/specs/npm/cjs_import_dual/run.out
+++ b/tests/specs/npm/cjs_import_dual/run.out
@@ -1,5 +1,5 @@
-Download http://localhost:4260/@denotest/cjs-import-dual
-Download http://localhost:4260/@denotest/dual-cjs-esm
+Download http://localhost:4260/@denotest%2fcjs-import-dual
+Download http://localhost:4260/@denotest%2fdual-cjs-esm
 Download http://localhost:4260/@denotest/cjs-import-dual/1.0.0.tgz
 Download http://localhost:4260/@denotest/dual-cjs-esm/1.0.0.tgz
 cjs
diff --git a/tests/specs/npm/cjs_invalid_name_exports/__test__.jsonc b/tests/specs/npm/cjs_invalid_name_exports/__test__.jsonc
index a38b8d0356..1d66adbd23 100644
--- a/tests/specs/npm/cjs_invalid_name_exports/__test__.jsonc
+++ b/tests/specs/npm/cjs_invalid_name_exports/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run --allow-read --quiet cjs-invalid-name-exports/main.ts",
-  "output": "cjs-invalid-name-exports/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "cjs-invalid-name-exports/main.out"
 }
diff --git a/tests/specs/npm/cjs_local_global_decls/__test__.jsonc b/tests/specs/npm/cjs_local_global_decls/__test__.jsonc
index 8bf847873f..6a42f26e6d 100644
--- a/tests/specs/npm/cjs_local_global_decls/__test__.jsonc
+++ b/tests/specs/npm/cjs_local_global_decls/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run --allow-read cjs_local_global_decls/main.ts",
-  "output": "cjs_local_global_decls/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "cjs_local_global_decls/main.out"
 }
diff --git a/tests/specs/npm/cjs_local_global_decls/cjs_local_global_decls/main.out b/tests/specs/npm/cjs_local_global_decls/cjs_local_global_decls/main.out
index 5e7a36c8d0..5c48b5b5cf 100644
--- a/tests/specs/npm/cjs_local_global_decls/cjs_local_global_decls/main.out
+++ b/tests/specs/npm/cjs_local_global_decls/cjs_local_global_decls/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/cjs-local-global-decls
+Download http://localhost:4260/@denotest%2fcjs-local-global-decls
 Download http://localhost:4260/@denotest/cjs-local-global-decls/1.0.0.tgz
 Loaded.
diff --git a/tests/specs/npm/cjs_module_export_assignment/__test__.jsonc b/tests/specs/npm/cjs_module_export_assignment/__test__.jsonc
index e9be6361a1..3a8c104aba 100644
--- a/tests/specs/npm/cjs_module_export_assignment/__test__.jsonc
+++ b/tests/specs/npm/cjs_module_export_assignment/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet --check=all cjs_module_export_assignment/main.ts",
-  "output": "cjs_module_export_assignment/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "cjs_module_export_assignment/main.out"
 }
diff --git a/tests/specs/npm/cjs_module_export_assignment_number/__test__.jsonc b/tests/specs/npm/cjs_module_export_assignment_number/__test__.jsonc
index d70f82e503..1b44f98c37 100644
--- a/tests/specs/npm/cjs_module_export_assignment_number/__test__.jsonc
+++ b/tests/specs/npm/cjs_module_export_assignment_number/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet --check=all cjs_module_export_assignment_number/main.ts",
-  "output": "cjs_module_export_assignment_number/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "cjs_module_export_assignment_number/main.out"
 }
diff --git a/tests/specs/npm/cjs_pkg_imports/__test__.jsonc b/tests/specs/npm/cjs_pkg_imports/__test__.jsonc
index c51f14b560..0ab9d873d9 100644
--- a/tests/specs/npm/cjs_pkg_imports/__test__.jsonc
+++ b/tests/specs/npm/cjs_pkg_imports/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A cjs_pkg_imports/main.ts",
-  "output": "cjs_pkg_imports/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "cjs_pkg_imports/main.out"
 }
diff --git a/tests/specs/npm/cjs_pkg_imports/cjs_pkg_imports/main.out b/tests/specs/npm/cjs_pkg_imports/cjs_pkg_imports/main.out
index 661146bd03..f9390fb1bc 100644
--- a/tests/specs/npm/cjs_pkg_imports/cjs_pkg_imports/main.out
+++ b/tests/specs/npm/cjs_pkg_imports/cjs_pkg_imports/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/cjs-pkg-imports
+Download http://localhost:4260/@denotest%2fcjs-pkg-imports
 Download http://localhost:4260/@denotest/cjs-pkg-imports/1.0.0.tgz
 { crypto: Crypto { subtle: SubtleCrypto {} }, number: 5 }
diff --git a/tests/specs/npm/cjs_reexport_collision/__test__.jsonc b/tests/specs/npm/cjs_reexport_collision/__test__.jsonc
index 0b9d1e6211..582b2c9574 100644
--- a/tests/specs/npm/cjs_reexport_collision/__test__.jsonc
+++ b/tests/specs/npm/cjs_reexport_collision/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet cjs_reexport_collision/main.ts",
-  "output": "cjs_reexport_collision/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "cjs_reexport_collision/main.out"
 }
diff --git a/tests/specs/npm/cjs_require_esm/__test__.jsonc b/tests/specs/npm/cjs_require_esm/__test__.jsonc
index 172f1ca650..b4e03afa3b 100644
--- a/tests/specs/npm/cjs_require_esm/__test__.jsonc
+++ b/tests/specs/npm/cjs_require_esm/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run --allow-read --quiet cjs_require_esm/main.ts",
-  "output": "cjs_require_esm/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "cjs_require_esm/main.out"
 }
diff --git a/tests/specs/npm/cjs_require_esm_mjs/__test__.jsonc b/tests/specs/npm/cjs_require_esm_mjs/__test__.jsonc
index 3a13231272..6bcb382e8d 100644
--- a/tests/specs/npm/cjs_require_esm_mjs/__test__.jsonc
+++ b/tests/specs/npm/cjs_require_esm_mjs/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run --allow-read --quiet cjs_require_esm_mjs/main.ts",
-  "output": "cjs_require_esm_mjs/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "cjs_require_esm_mjs/main.out"
 }
diff --git a/tests/specs/npm/cjs_sub_path/__test__.jsonc b/tests/specs/npm/cjs_sub_path/__test__.jsonc
index dbec76a13b..6a22c17649 100644
--- a/tests/specs/npm/cjs_sub_path/__test__.jsonc
+++ b/tests/specs/npm/cjs_sub_path/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run --allow-read cjs_sub_path/main.js",
-  "output": "cjs_sub_path/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "cjs_sub_path/main.out"
 }
diff --git a/tests/specs/npm/cjs_this_in_exports/__test__.jsonc b/tests/specs/npm/cjs_this_in_exports/__test__.jsonc
index 251691ca8e..f3b5985810 100644
--- a/tests/specs/npm/cjs_this_in_exports/__test__.jsonc
+++ b/tests/specs/npm/cjs_this_in_exports/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "run --allow-read --quiet cjs_this_in_exports/main.js",
   "output": "cjs_this_in_exports/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/cjs_with_deps/__test__.jsonc b/tests/specs/npm/cjs_with_deps/__test__.jsonc
index d9014f102a..e79fda5c77 100644
--- a/tests/specs/npm/cjs_with_deps/__test__.jsonc
+++ b/tests/specs/npm/cjs_with_deps/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run --allow-read --allow-env cjs_with_deps/main.js",
-  "output": "cjs_with_deps/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "cjs_with_deps/main.out"
 }
diff --git a/tests/specs/npm/compare_globals/__test__.jsonc b/tests/specs/npm/compare_globals/__test__.jsonc
index d86a76dbc7..96458306a7 100644
--- a/tests/specs/npm/compare_globals/__test__.jsonc
+++ b/tests/specs/npm/compare_globals/__test__.jsonc
@@ -1,8 +1,4 @@
 {
-  "args": "run --allow-read --check=all compare_globals/main.ts",
-  "output": "compare_globals/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "args": "run --allow-read --check=all main.ts",
+  "output": "main.out"
 }
diff --git a/tests/specs/npm/compare_globals/compare_globals/main.out b/tests/specs/npm/compare_globals/main.out
similarity index 76%
rename from tests/specs/npm/compare_globals/compare_globals/main.out
rename to tests/specs/npm/compare_globals/main.out
index a1b0a566d5..290e9c3b23 100644
--- a/tests/specs/npm/compare_globals/compare_globals/main.out
+++ b/tests/specs/npm/compare_globals/main.out
@@ -1,17 +1,18 @@
 [UNORDERED_START]
-Download http://localhost:4260/@types/node
+Download http://localhost:4260/@types%2fnode
 Download http://localhost:4260/undici-types
-Download http://localhost:4260/@denotest/globals
+Download http://localhost:4260/@denotest%2fglobals
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/globals/1.0.0.tgz
 Download http://localhost:4260/@types/node/node-22.5.4.tgz
 Download http://localhost:4260/undici-types/undici-types-6.19.8.tgz
 [UNORDERED_END]
-Check file:///[WILDCARD]/compare_globals/main.ts
+Check file:///[WILDCARD]/main.ts
 true
 true
 []
+process equals process true
 setTimeout 1 false
 setTimeout 2 function
 setTimeout 3 function
diff --git a/tests/specs/npm/compare_globals/compare_globals/main.ts b/tests/specs/npm/compare_globals/main.ts
similarity index 84%
rename from tests/specs/npm/compare_globals/compare_globals/main.ts
rename to tests/specs/npm/compare_globals/main.ts
index 9482798d8c..308ce9b23f 100644
--- a/tests/specs/npm/compare_globals/compare_globals/main.ts
+++ b/tests/specs/npm/compare_globals/main.ts
@@ -5,10 +5,17 @@ console.log(globals.global === globals.globalThis);
 // @ts-expect-error even though these are the same object, they have different types
 console.log(globals.globalThis === globalThis);
 console.log(globals.process.execArgv);
+console.log("process equals process", process === globals.process);
 
 type AssertTrue<T extends true> = never;
-type _TestNoProcessGlobal = AssertTrue<
-  typeof globalThis extends { process: any } ? false : true
+type _TestHasProcessGlobal = AssertTrue<
+  typeof globalThis extends { process: any } ? true : false
+>;
+type _TestProcessGlobalVersion = AssertTrue<
+  typeof process.versions.node extends string ? true : false
+>;
+type _TestNoBufferGlogal = AssertTrue<
+  typeof globalThis extends { Buffer: any } ? false : true
 >;
 type _TestHasNodeJsGlobal = NodeJS.Architecture;
 
diff --git a/tests/specs/npm/conditional_exports/main.out b/tests/specs/npm/conditional_exports/main.out
index 8bd31321b6..8b5b2715be 100644
--- a/tests/specs/npm/conditional_exports/main.out
+++ b/tests/specs/npm/conditional_exports/main.out
@@ -1,8 +1,8 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/conditional-exports
+Download http://localhost:4260/@denotest%2fconditional-exports
 Download http://localhost:4260/supports-esm
 Download http://localhost:4260/has-package-exports
-Download http://localhost:4260/@ljharb/has-package-exports-patterns
+Download http://localhost:4260/@ljharb%2fhas-package-exports-patterns
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/conditional-exports/1.0.0.tgz
diff --git a/tests/specs/npm/conditional_exports_node_modules_dir/main.out b/tests/specs/npm/conditional_exports_node_modules_dir/main.out
index 5fbba560d3..ee4a64be61 100644
--- a/tests/specs/npm/conditional_exports_node_modules_dir/main.out
+++ b/tests/specs/npm/conditional_exports_node_modules_dir/main.out
@@ -1,8 +1,8 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/conditional-exports
+Download http://localhost:4260/@denotest%2fconditional-exports
 Download http://localhost:4260/supports-esm
 Download http://localhost:4260/has-package-exports
-Download http://localhost:4260/@ljharb/has-package-exports-patterns
+Download http://localhost:4260/@ljharb%2fhas-package-exports-patterns
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/conditional-exports/1.0.0.tgz
diff --git a/tests/specs/npm/create_require/__test__.jsonc b/tests/specs/npm/create_require/__test__.jsonc
index 40d9ce0669..901a977d7c 100644
--- a/tests/specs/npm/create_require/__test__.jsonc
+++ b/tests/specs/npm/create_require/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "run --reload --allow-read create_require/main.ts",
   "output": "create_require/main.out",
-  "exitCode": 0,
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "exitCode": 0
 }
diff --git a/tests/specs/npm/deno_cache/__test__.jsonc b/tests/specs/npm/deno_cache/__test__.jsonc
index 93b204c033..302b25e413 100644
--- a/tests/specs/npm/deno_cache/__test__.jsonc
+++ b/tests/specs/npm/deno_cache/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "cache --reload npm:chalk npm:mkdirp",
-  "output": "deno_cache.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "deno_cache.out"
 }
diff --git a/tests/specs/npm/deno_run_bin_cjs/__test__.jsonc b/tests/specs/npm/deno_run_bin_cjs/__test__.jsonc
index 9eb8e9bfec..cd4bcb119c 100644
--- a/tests/specs/npm/deno_run_bin_cjs/__test__.jsonc
+++ b/tests/specs/npm/deno_run_bin_cjs/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet npm:@denotest/bin/cli-cjs this is a test",
-  "output": "deno_run_cjs.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "deno_run_cjs.out"
 }
diff --git a/tests/specs/npm/deno_run_bin_cjs_no_bin_entrypoint/__test__.jsonc b/tests/specs/npm/deno_run_bin_cjs_no_bin_entrypoint/__test__.jsonc
index 6ee5a326ba..0e86d9974c 100644
--- a/tests/specs/npm/deno_run_bin_cjs_no_bin_entrypoint/__test__.jsonc
+++ b/tests/specs/npm/deno_run_bin_cjs_no_bin_entrypoint/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet npm:@denotest/bin@0.6.0/cli-cjs.js this is a test",
-  "output": "deno_run_cjs.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "deno_run_cjs.out"
 }
diff --git a/tests/specs/npm/deno_run_bin_esm/__test__.jsonc b/tests/specs/npm/deno_run_bin_esm/__test__.jsonc
index fc48451bb6..828cf6b0da 100644
--- a/tests/specs/npm/deno_run_bin_esm/__test__.jsonc
+++ b/tests/specs/npm/deno_run_bin_esm/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet npm:@denotest/bin/cli-esm this is a test",
-  "output": "deno_run_esm.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "deno_run_esm.out"
 }
diff --git a/tests/specs/npm/deno_run_bin_esm_no_bin_entrypoint/__test__.jsonc b/tests/specs/npm/deno_run_bin_esm_no_bin_entrypoint/__test__.jsonc
index 956755b306..c2c0117f7a 100644
--- a/tests/specs/npm/deno_run_bin_esm_no_bin_entrypoint/__test__.jsonc
+++ b/tests/specs/npm/deno_run_bin_esm_no_bin_entrypoint/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet npm:@denotest/bin@0.6.0/cli.mjs this is a test",
-  "output": "deno_run_esm.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "deno_run_esm.out"
 }
diff --git a/tests/specs/npm/deno_run_bin_no_ext/__test__.jsonc b/tests/specs/npm/deno_run_bin_no_ext/__test__.jsonc
index 71877b399b..3f5cc3f2a4 100644
--- a/tests/specs/npm/deno_run_bin_no_ext/__test__.jsonc
+++ b/tests/specs/npm/deno_run_bin_no_ext/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet npm:@denotest/bin/cli-no-ext this is a test",
-  "output": "deno_run_no_ext.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "deno_run_no_ext.out"
 }
diff --git a/tests/specs/npm/deno_run_bin_special_chars/__test__.jsonc b/tests/specs/npm/deno_run_bin_special_chars/__test__.jsonc
index c3e14c0b71..23a339349d 100644
--- a/tests/specs/npm/deno_run_bin_special_chars/__test__.jsonc
+++ b/tests/specs/npm/deno_run_bin_special_chars/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet npm:@denotest/special-chars-in-bin-name/\\foo\" this is a test",
-  "output": "deno_run_special_chars_in_bin_name.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "deno_run_special_chars_in_bin_name.out"
 }
diff --git a/tests/specs/npm/deno_run_cowsay/__test__.jsonc b/tests/specs/npm/deno_run_cowsay/__test__.jsonc
index 0015b88be8..36a677534c 100644
--- a/tests/specs/npm/deno_run_cowsay/__test__.jsonc
+++ b/tests/specs/npm/deno_run_cowsay/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet npm:cowsay@1.5.0 Hello",
-  "output": "deno_run_cowsay.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "deno_run_cowsay.out"
 }
diff --git a/tests/specs/npm/deno_run_cowsay_explicit/__test__.jsonc b/tests/specs/npm/deno_run_cowsay_explicit/__test__.jsonc
index 1ecce925e8..a515fd16ce 100644
--- a/tests/specs/npm/deno_run_cowsay_explicit/__test__.jsonc
+++ b/tests/specs/npm/deno_run_cowsay_explicit/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet npm:cowsay@1.5.0/cowsay Hello",
-  "output": "deno_run_cowsay.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "deno_run_cowsay.out"
 }
diff --git a/tests/specs/npm/deno_run_cowsay_with_node_modules_dir/__test__.jsonc b/tests/specs/npm/deno_run_cowsay_with_node_modules_dir/__test__.jsonc
index d2c95f0728..fdc0a7da1e 100644
--- a/tests/specs/npm/deno_run_cowsay_with_node_modules_dir/__test__.jsonc
+++ b/tests/specs/npm/deno_run_cowsay_with_node_modules_dir/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "tempDir": true,
   "args": "run -A --quiet --node-modules-dir npm:cowsay@1.5.0 Hello",
-  "output": "deno_run_cowsay.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "deno_run_cowsay.out"
 }
diff --git a/tests/specs/npm/deno_run_cowthink/__test__.jsonc b/tests/specs/npm/deno_run_cowthink/__test__.jsonc
index 2acc84e7b9..622c0a51c3 100644
--- a/tests/specs/npm/deno_run_cowthink/__test__.jsonc
+++ b/tests/specs/npm/deno_run_cowthink/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet npm:cowsay@1.5.0/cowthink Hello",
-  "output": "deno_run_cowthink.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "deno_run_cowthink.out"
 }
diff --git a/tests/specs/npm/deno_run_no_bin_entrypoint/__test__.jsonc b/tests/specs/npm/deno_run_no_bin_entrypoint/__test__.jsonc
index 5331ec9c41..43a2701f19 100644
--- a/tests/specs/npm/deno_run_no_bin_entrypoint/__test__.jsonc
+++ b/tests/specs/npm/deno_run_no_bin_entrypoint/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "run -A --quiet npm:@denotest/esm-basic",
   "output": "deno_run_no_bin_entrypoint.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/deno_run_no_bin_entrypoint_non_existent_subpath/__test__.jsonc b/tests/specs/npm/deno_run_no_bin_entrypoint_non_existent_subpath/__test__.jsonc
index 3eaa8274c6..94b12f2b4a 100644
--- a/tests/specs/npm/deno_run_no_bin_entrypoint_non_existent_subpath/__test__.jsonc
+++ b/tests/specs/npm/deno_run_no_bin_entrypoint_non_existent_subpath/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "run -A --quiet npm:@denotest/esm-basic/non-existent.js",
   "output": "deno_run_no_bin_entrypoint_non_existent_subpath.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/deno_run_non_existent/__test__.jsonc b/tests/specs/npm/deno_run_non_existent/__test__.jsonc
index 72dc01450b..d112c96699 100644
--- a/tests/specs/npm/deno_run_non_existent/__test__.jsonc
+++ b/tests/specs/npm/deno_run_non_existent/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "run npm:mkdirp@0.5.125",
   "output": "deno_run_non_existent.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/different_nested_dep_node_modules_dir_false/__test__.jsonc b/tests/specs/npm/different_nested_dep_node_modules_dir_false/__test__.jsonc
index 24587d928e..07db0a1acb 100644
--- a/tests/specs/npm/different_nested_dep_node_modules_dir_false/__test__.jsonc
+++ b/tests/specs/npm/different_nested_dep_node_modules_dir_false/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "run --quiet --no-lock --node-modules-dir=none different_nested_dep/main.js",
   "output": "different_nested_dep/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/npm/different_nested_dep_node_modules_dir_true/__test__.jsonc b/tests/specs/npm/different_nested_dep_node_modules_dir_true/__test__.jsonc
index a5c40cdd95..7fd130e506 100644
--- a/tests/specs/npm/different_nested_dep_node_modules_dir_true/__test__.jsonc
+++ b/tests/specs/npm/different_nested_dep_node_modules_dir_true/__test__.jsonc
@@ -2,9 +2,5 @@
   "tempDir": true,
   "args": "run --no-lock --quiet --node-modules-dir=auto different_nested_dep/main.js",
   "output": "different_nested_dep/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/npm/directory_import_folder_index_js/__test__.jsonc b/tests/specs/npm/directory_import_folder_index_js/__test__.jsonc
index 8eb6226d6a..b3f7b64cbd 100644
--- a/tests/specs/npm/directory_import_folder_index_js/__test__.jsonc
+++ b/tests/specs/npm/directory_import_folder_index_js/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "run directory_import/folder_index_js.ts",
   "output": "directory_import/folder_index_js.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/directory_import_folder_index_js/directory_import/folder_index_js.out b/tests/specs/npm/directory_import_folder_index_js/directory_import/folder_index_js.out
index a700b8fdb6..c1eb2a4801 100644
--- a/tests/specs/npm/directory_import_folder_index_js/directory_import/folder_index_js.out
+++ b/tests/specs/npm/directory_import_folder_index_js/directory_import/folder_index_js.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/sub-folders
+Download http://localhost:4260/@denotest%2fsub-folders
 Download http://localhost:4260/@denotest/sub-folders/1.0.0.tgz
 error: Directory import [WILDCARD]folder_index_js is not supported resolving import from file:///[WILDCARD]/directory_import/folder_index_js.ts
 Did you mean to import index.js within the directory?
diff --git a/tests/specs/npm/directory_import_folder_index_js/directory_import/folder_no_index.out b/tests/specs/npm/directory_import_folder_index_js/directory_import/folder_no_index.out
index 844419b4c6..c19c4bcaa4 100644
--- a/tests/specs/npm/directory_import_folder_index_js/directory_import/folder_no_index.out
+++ b/tests/specs/npm/directory_import_folder_index_js/directory_import/folder_no_index.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/sub-folders
+Download http://localhost:4260/@denotest%2fsub-folders
 Download http://localhost:4260/@denotest/sub-folders/1.0.0.tgz
 error: Directory import [WILDCARD]folder_no_index is not supported resolving import from file:///[WILDCARD]/folder_no_index.ts
 
diff --git a/tests/specs/npm/directory_import_folder_no_index/__test__.jsonc b/tests/specs/npm/directory_import_folder_no_index/__test__.jsonc
index 6137479980..e0bb868ad8 100644
--- a/tests/specs/npm/directory_import_folder_no_index/__test__.jsonc
+++ b/tests/specs/npm/directory_import_folder_no_index/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "run directory_import/folder_no_index.ts",
   "output": "directory_import/folder_no_index.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/directory_import_folder_no_index/directory_import/folder_index_js.out b/tests/specs/npm/directory_import_folder_no_index/directory_import/folder_index_js.out
index a700b8fdb6..c1eb2a4801 100644
--- a/tests/specs/npm/directory_import_folder_no_index/directory_import/folder_index_js.out
+++ b/tests/specs/npm/directory_import_folder_no_index/directory_import/folder_index_js.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/sub-folders
+Download http://localhost:4260/@denotest%2fsub-folders
 Download http://localhost:4260/@denotest/sub-folders/1.0.0.tgz
 error: Directory import [WILDCARD]folder_index_js is not supported resolving import from file:///[WILDCARD]/directory_import/folder_index_js.ts
 Did you mean to import index.js within the directory?
diff --git a/tests/specs/npm/directory_import_folder_no_index/directory_import/folder_no_index.out b/tests/specs/npm/directory_import_folder_no_index/directory_import/folder_no_index.out
index 844419b4c6..c19c4bcaa4 100644
--- a/tests/specs/npm/directory_import_folder_no_index/directory_import/folder_no_index.out
+++ b/tests/specs/npm/directory_import_folder_no_index/directory_import/folder_no_index.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/sub-folders
+Download http://localhost:4260/@denotest%2fsub-folders
 Download http://localhost:4260/@denotest/sub-folders/1.0.0.tgz
 error: Directory import [WILDCARD]folder_no_index is not supported resolving import from file:///[WILDCARD]/folder_no_index.ts
 
diff --git a/tests/specs/npm/dual_cjs_esm/__test__.jsonc b/tests/specs/npm/dual_cjs_esm/__test__.jsonc
deleted file mode 100644
index 5ace51cecb..0000000000
--- a/tests/specs/npm/dual_cjs_esm/__test__.jsonc
+++ /dev/null
@@ -1,8 +0,0 @@
-{
-  "args": "run -A --quiet dual_cjs_esm/main.ts",
-  "output": "dual_cjs_esm/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
-}
diff --git a/tests/specs/npm/dual_cjs_esm/cjs_referrer/__test__.jsonc b/tests/specs/npm/dual_cjs_esm/cjs_referrer/__test__.jsonc
new file mode 100644
index 0000000000..de2c1a0bc5
--- /dev/null
+++ b/tests/specs/npm/dual_cjs_esm/cjs_referrer/__test__.jsonc
@@ -0,0 +1,14 @@
+{
+  "tempDir": true,
+  "tests": {
+    "check": {
+      "args": "check --node-modules-dir=auto main.cts",
+      "output": "check.out",
+      "exitCode": 1
+    },
+    "run": {
+      "args": "run --node-modules-dir=auto --allow-read main.cts",
+      "output": "main.out"
+    }
+  }
+}
diff --git a/tests/specs/npm/dual_cjs_esm/cjs_referrer/check.out b/tests/specs/npm/dual_cjs_esm/cjs_referrer/check.out
new file mode 100644
index 0000000000..267d31fb75
--- /dev/null
+++ b/tests/specs/npm/dual_cjs_esm/cjs_referrer/check.out
@@ -0,0 +1,8 @@
+Download http://localhost:4260/@denotest%2fdual-cjs-esm
+Download http://localhost:4260/@denotest/dual-cjs-esm/1.0.0.tgz
+Initialize @denotest/dual-cjs-esm@1.0.0
+Check file:///[WILDLINE]/main.cts
+error: TS2322 [ERROR]: Type '"cjs"' is not assignable to type '"other"'.
+const kind: "other" = mod.getKind();
+      ~~~~
+    at file:///[WILDLINE]/main.cts:3:7
diff --git a/tests/specs/npm/dual_cjs_esm/cjs_referrer/main.cts b/tests/specs/npm/dual_cjs_esm/cjs_referrer/main.cts
new file mode 100644
index 0000000000..b8dd343f8b
--- /dev/null
+++ b/tests/specs/npm/dual_cjs_esm/cjs_referrer/main.cts
@@ -0,0 +1,4 @@
+import mod = require("@denotest/dual-cjs-esm");
+
+const kind: "other" = mod.getKind();
+console.log(kind);
diff --git a/tests/specs/npm/dual_cjs_esm/cjs_referrer/main.out b/tests/specs/npm/dual_cjs_esm/cjs_referrer/main.out
new file mode 100644
index 0000000000..62ddbf4793
--- /dev/null
+++ b/tests/specs/npm/dual_cjs_esm/cjs_referrer/main.out
@@ -0,0 +1,4 @@
+Download http://localhost:4260/@denotest%2fdual-cjs-esm
+Download http://localhost:4260/@denotest/dual-cjs-esm/1.0.0.tgz
+Initialize @denotest/dual-cjs-esm@1.0.0
+cjs
diff --git a/tests/specs/npm/dual_cjs_esm/cjs_referrer/package.json b/tests/specs/npm/dual_cjs_esm/cjs_referrer/package.json
new file mode 100644
index 0000000000..e1b1e1a5f8
--- /dev/null
+++ b/tests/specs/npm/dual_cjs_esm/cjs_referrer/package.json
@@ -0,0 +1,5 @@
+{
+  "dependencies": {
+    "@denotest/dual-cjs-esm": "*"
+  }
+}
diff --git a/tests/specs/npm/dual_cjs_esm/esm_referrer/__test__.jsonc b/tests/specs/npm/dual_cjs_esm/esm_referrer/__test__.jsonc
new file mode 100644
index 0000000000..0ef1472536
--- /dev/null
+++ b/tests/specs/npm/dual_cjs_esm/esm_referrer/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run -A --quiet main.ts",
+  "output": "main.out"
+}
diff --git a/tests/specs/npm/dual_cjs_esm/dual_cjs_esm/main.out b/tests/specs/npm/dual_cjs_esm/esm_referrer/main.out
similarity index 100%
rename from tests/specs/npm/dual_cjs_esm/dual_cjs_esm/main.out
rename to tests/specs/npm/dual_cjs_esm/esm_referrer/main.out
diff --git a/tests/specs/npm/dual_cjs_esm/dual_cjs_esm/main.ts b/tests/specs/npm/dual_cjs_esm/esm_referrer/main.ts
similarity index 100%
rename from tests/specs/npm/dual_cjs_esm/dual_cjs_esm/main.ts
rename to tests/specs/npm/dual_cjs_esm/esm_referrer/main.ts
diff --git a/tests/specs/npm/dual_cjs_esm/ts_referrer_type_cjs/__test__.jsonc b/tests/specs/npm/dual_cjs_esm/ts_referrer_type_cjs/__test__.jsonc
new file mode 100644
index 0000000000..cf19217d18
--- /dev/null
+++ b/tests/specs/npm/dual_cjs_esm/ts_referrer_type_cjs/__test__.jsonc
@@ -0,0 +1,14 @@
+{
+  "tempDir": true,
+  "tests": {
+    "check": {
+      "args": "check --node-modules-dir=auto main.ts",
+      "output": "check.out",
+      "exitCode": 1
+    },
+    "run": {
+      "args": "run --node-modules-dir=auto --allow-read main.ts",
+      "output": "main.out"
+    }
+  }
+}
diff --git a/tests/specs/npm/dual_cjs_esm/ts_referrer_type_cjs/check.out b/tests/specs/npm/dual_cjs_esm/ts_referrer_type_cjs/check.out
new file mode 100644
index 0000000000..cbd7740a9f
--- /dev/null
+++ b/tests/specs/npm/dual_cjs_esm/ts_referrer_type_cjs/check.out
@@ -0,0 +1,8 @@
+Download http://localhost:4260/@denotest%2fdual-cjs-esm
+Download http://localhost:4260/@denotest/dual-cjs-esm/1.0.0.tgz
+Initialize @denotest/dual-cjs-esm@1.0.0
+Check file:///[WILDLINE]/main.ts
+error: TS2322 [ERROR]: Type '"cjs"' is not assignable to type '"other"'.
+const kind: "other" = mod.getKind();
+      ~~~~
+    at file:///[WILDLINE]/main.ts:3:7
diff --git a/tests/specs/npm/dual_cjs_esm/ts_referrer_type_cjs/main.out b/tests/specs/npm/dual_cjs_esm/ts_referrer_type_cjs/main.out
new file mode 100644
index 0000000000..62ddbf4793
--- /dev/null
+++ b/tests/specs/npm/dual_cjs_esm/ts_referrer_type_cjs/main.out
@@ -0,0 +1,4 @@
+Download http://localhost:4260/@denotest%2fdual-cjs-esm
+Download http://localhost:4260/@denotest/dual-cjs-esm/1.0.0.tgz
+Initialize @denotest/dual-cjs-esm@1.0.0
+cjs
diff --git a/tests/specs/npm/dual_cjs_esm/ts_referrer_type_cjs/main.ts b/tests/specs/npm/dual_cjs_esm/ts_referrer_type_cjs/main.ts
new file mode 100644
index 0000000000..b8dd343f8b
--- /dev/null
+++ b/tests/specs/npm/dual_cjs_esm/ts_referrer_type_cjs/main.ts
@@ -0,0 +1,4 @@
+import mod = require("@denotest/dual-cjs-esm");
+
+const kind: "other" = mod.getKind();
+console.log(kind);
diff --git a/tests/specs/npm/dual_cjs_esm/ts_referrer_type_cjs/package.json b/tests/specs/npm/dual_cjs_esm/ts_referrer_type_cjs/package.json
new file mode 100644
index 0000000000..419d3d9f11
--- /dev/null
+++ b/tests/specs/npm/dual_cjs_esm/ts_referrer_type_cjs/package.json
@@ -0,0 +1,6 @@
+{
+  "type": "commonjs",
+  "dependencies": {
+    "@denotest/dual-cjs-esm": "*"
+  }
+}
diff --git a/tests/specs/npm/dynamic_import_deno_ts_from_npm/__test__.jsonc b/tests/specs/npm/dynamic_import_deno_ts_from_npm/__test__.jsonc
index 8dbee51c7e..61ad30115d 100644
--- a/tests/specs/npm/dynamic_import_deno_ts_from_npm/__test__.jsonc
+++ b/tests/specs/npm/dynamic_import_deno_ts_from_npm/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run --allow-read --quiet dynamic_import_deno_ts_from_npm/main.ts",
-  "output": "dynamic_import_deno_ts_from_npm/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "dynamic_import_deno_ts_from_npm/main.out"
 }
diff --git a/tests/specs/npm/dynamic_import_invalid_package_name/__test__.jsonc b/tests/specs/npm/dynamic_import_invalid_package_name/__test__.jsonc
index a15cabf83a..912ff43147 100644
--- a/tests/specs/npm/dynamic_import_invalid_package_name/__test__.jsonc
+++ b/tests/specs/npm/dynamic_import_invalid_package_name/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --reload dynamic_import_invalid_package_name/main.ts",
-  "output": "dynamic_import_invalid_package_name/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "dynamic_import_invalid_package_name/main.out"
 }
diff --git a/tests/specs/npm/dynamic_import_json/__test__.jsonc b/tests/specs/npm/dynamic_import_json/__test__.jsonc
index 9b4f5a2124..ee05ba69af 100644
--- a/tests/specs/npm/dynamic_import_json/__test__.jsonc
+++ b/tests/specs/npm/dynamic_import_json/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet import_json/main.js",
-  "output": "import_json/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "import_json/main.out"
 }
diff --git a/tests/specs/npm/dynamic_import_reload_same_package/__test__.jsonc b/tests/specs/npm/dynamic_import_reload_same_package/__test__.jsonc
index d255b9a872..4434b794dd 100644
--- a/tests/specs/npm/dynamic_import_reload_same_package/__test__.jsonc
+++ b/tests/specs/npm/dynamic_import_reload_same_package/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --reload dynamic_import_reload_same_package/main.ts",
-  "output": "dynamic_import_reload_same_package/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "dynamic_import_reload_same_package/main.out"
 }
diff --git a/tests/specs/npm/dynamic_npm_resolution_failure/main.out b/tests/specs/npm/dynamic_npm_resolution_failure/main.out
index d9eb7182fa..8888c4f0ae 100644
--- a/tests/specs/npm/dynamic_npm_resolution_failure/main.out
+++ b/tests/specs/npm/dynamic_npm_resolution_failure/main.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
 Download http://localhost:4260/chalk
-Download http://localhost:4260/@denotest/dep-cannot-parse
+Download http://localhost:4260/@denotest%2fdep-cannot-parse
 [UNORDERED_END]
 Download http://localhost:4260/chalk/chalk-5.0.1.tgz
 Hi
diff --git a/tests/specs/npm/env_var_re_export_dev/__test__.jsonc b/tests/specs/npm/env_var_re_export_dev/__test__.jsonc
index e65ae0308d..50d8353ca1 100644
--- a/tests/specs/npm/env_var_re_export_dev/__test__.jsonc
+++ b/tests/specs/npm/env_var_re_export_dev/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run --allow-read --allow-env --quiet env_var_re_export/main.js",
-  "output": "dev\n",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "dev\n"
 }
diff --git a/tests/specs/npm/env_var_re_export_prod/__test__.jsonc b/tests/specs/npm/env_var_re_export_prod/__test__.jsonc
index 6c206ba3e9..64b19e1a7a 100644
--- a/tests/specs/npm/env_var_re_export_prod/__test__.jsonc
+++ b/tests/specs/npm/env_var_re_export_prod/__test__.jsonc
@@ -2,8 +2,6 @@
   "args": "run --allow-read --allow-env --quiet env_var_re_export/main.js",
   "output": "prod\n",
   "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/",
     "NODE_ENV": "production"
   }
 }
diff --git a/tests/specs/npm/error_version_after_subpath/__test__.jsonc b/tests/specs/npm/error_version_after_subpath/__test__.jsonc
index 157e238d8a..467d42157e 100644
--- a/tests/specs/npm/error_version_after_subpath/__test__.jsonc
+++ b/tests/specs/npm/error_version_after_subpath/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "run -A --quiet error_version_after_subpath/main.js",
   "output": "error_version_after_subpath/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/esm_import_cjs_default/main.out b/tests/specs/npm/esm_import_cjs_default/main.out
index ec7962e5a3..6528a68d7c 100644
--- a/tests/specs/npm/esm_import_cjs_default/main.out
+++ b/tests/specs/npm/esm_import_cjs_default/main.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/esm-import-cjs-default
-Download http://localhost:4260/@denotest/cjs-default-export
+Download http://localhost:4260/@denotest%2fesm-import-cjs-default
+Download http://localhost:4260/@denotest%2fcjs-default-export
 Download http://localhost:4260/@denotest/cjs-default-export/1.0.0.tgz
 Download http://localhost:4260/@denotest/esm-import-cjs-default/1.0.0.tgz
 [UNORDERED_END]
diff --git a/tests/specs/npm/import_json/__test__.jsonc b/tests/specs/npm/import_json/__test__.jsonc
index 9b4f5a2124..ee05ba69af 100644
--- a/tests/specs/npm/import_json/__test__.jsonc
+++ b/tests/specs/npm/import_json/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet import_json/main.js",
-  "output": "import_json/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "import_json/main.out"
 }
diff --git a/tests/specs/npm/import_map/__test__.jsonc b/tests/specs/npm/import_map/__test__.jsonc
index 822acbbe4e..7c39e48e9d 100644
--- a/tests/specs/npm/import_map/__test__.jsonc
+++ b/tests/specs/npm/import_map/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run --allow-read --allow-env --import-map import_map/import_map.json import_map/main.js",
-  "output": "import_map/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "import_map/main.out"
 }
diff --git a/tests/specs/npm/import_map/import_map/main.out b/tests/specs/npm/import_map/import_map/main.out
index 05f313d4e9..2698fb695c 100644
--- a/tests/specs/npm/import_map/import_map/main.out
+++ b/tests/specs/npm/import_map/import_map/main.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
 Download http://localhost:4260/chalk
-Download http://localhost:4260/@denotest/dual-cjs-esm
+Download http://localhost:4260/@denotest%2fdual-cjs-esm
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/dual-cjs-esm/1.0.0.tgz
diff --git a/tests/specs/npm/imports_package_json/__test__.jsonc b/tests/specs/npm/imports_package_json/__test__.jsonc
index e11b92132e..35eabd4e15 100644
--- a/tests/specs/npm/imports_package_json/__test__.jsonc
+++ b/tests/specs/npm/imports_package_json/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run --no-lock --node-modules-dir=none imports_package_json/main.js",
-  "output": "imports_package_json/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "imports_package_json/main.out"
 }
diff --git a/tests/specs/npm/imports_package_json/imports_package_json/import_not_defined.out b/tests/specs/npm/imports_package_json/imports_package_json/import_not_defined.out
index 70d1145a37..abfa414030 100644
--- a/tests/specs/npm/imports_package_json/imports_package_json/import_not_defined.out
+++ b/tests/specs/npm/imports_package_json/imports_package_json/import_not_defined.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/imports-package-json
+Download http://localhost:4260/@denotest%2fimports-package-json
 Download http://localhost:4260/@denotest/imports-package-json/1.0.0.tgz
 error: [ERR_PACKAGE_IMPORT_NOT_DEFINED] Package import specifier "#not-defined" is not defined in package [WILDCARD]package.json imported from '[WILDCARD]import_not_defined.js'
diff --git a/tests/specs/npm/imports_package_json/imports_package_json/main.out b/tests/specs/npm/imports_package_json/imports_package_json/main.out
index 979e355765..70d787b251 100644
--- a/tests/specs/npm/imports_package_json/imports_package_json/main.out
+++ b/tests/specs/npm/imports_package_json/imports_package_json/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/imports-package-json
+Download http://localhost:4260/@denotest%2fimports-package-json
 Download http://localhost:4260/@denotest/imports-package-json/1.0.0.tgz
 hi
 bye
diff --git a/tests/specs/npm/imports_package_json/imports_package_json/sub_path_import_not_defined.out b/tests/specs/npm/imports_package_json/imports_package_json/sub_path_import_not_defined.out
index 7c803f2bf1..95524202ae 100644
--- a/tests/specs/npm/imports_package_json/imports_package_json/sub_path_import_not_defined.out
+++ b/tests/specs/npm/imports_package_json/imports_package_json/sub_path_import_not_defined.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/imports-package-json
+Download http://localhost:4260/@denotest%2fimports-package-json
 Download http://localhost:4260/@denotest/imports-package-json/1.0.0.tgz
 error: [ERR_PACKAGE_IMPORT_NOT_DEFINED] Package import specifier "#hi" is not defined in package [WILDCARD]sub_path[WILDCARD]package.json imported from '[WILDCARD]import_not_defined.js'
diff --git a/tests/specs/npm/imports_package_json_import_not_defined/__test__.jsonc b/tests/specs/npm/imports_package_json_import_not_defined/__test__.jsonc
index 0f094838c1..983ec31263 100644
--- a/tests/specs/npm/imports_package_json_import_not_defined/__test__.jsonc
+++ b/tests/specs/npm/imports_package_json_import_not_defined/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "run --no-lock --node-modules-dir=none imports_package_json/import_not_defined.js",
   "output": "imports_package_json/import_not_defined.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/import_not_defined.out b/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/import_not_defined.out
index 70d1145a37..abfa414030 100644
--- a/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/import_not_defined.out
+++ b/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/import_not_defined.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/imports-package-json
+Download http://localhost:4260/@denotest%2fimports-package-json
 Download http://localhost:4260/@denotest/imports-package-json/1.0.0.tgz
 error: [ERR_PACKAGE_IMPORT_NOT_DEFINED] Package import specifier "#not-defined" is not defined in package [WILDCARD]package.json imported from '[WILDCARD]import_not_defined.js'
diff --git a/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/main.out b/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/main.out
index 979e355765..70d787b251 100644
--- a/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/main.out
+++ b/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/imports-package-json
+Download http://localhost:4260/@denotest%2fimports-package-json
 Download http://localhost:4260/@denotest/imports-package-json/1.0.0.tgz
 hi
 bye
diff --git a/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/sub_path_import_not_defined.out b/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/sub_path_import_not_defined.out
index 7c803f2bf1..95524202ae 100644
--- a/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/sub_path_import_not_defined.out
+++ b/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/sub_path_import_not_defined.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/imports-package-json
+Download http://localhost:4260/@denotest%2fimports-package-json
 Download http://localhost:4260/@denotest/imports-package-json/1.0.0.tgz
 error: [ERR_PACKAGE_IMPORT_NOT_DEFINED] Package import specifier "#hi" is not defined in package [WILDCARD]sub_path[WILDCARD]package.json imported from '[WILDCARD]import_not_defined.js'
diff --git a/tests/specs/npm/imports_package_json_sub_path_import_not_defined/__test__.jsonc b/tests/specs/npm/imports_package_json_sub_path_import_not_defined/__test__.jsonc
index f862dc58e4..cd9b260f48 100644
--- a/tests/specs/npm/imports_package_json_sub_path_import_not_defined/__test__.jsonc
+++ b/tests/specs/npm/imports_package_json_sub_path_import_not_defined/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "run --no-lock --node-modules-dir=none imports_package_json/sub_path_import_not_defined.js",
   "output": "imports_package_json/sub_path_import_not_defined.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/import_not_defined.out b/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/import_not_defined.out
index 70d1145a37..abfa414030 100644
--- a/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/import_not_defined.out
+++ b/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/import_not_defined.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/imports-package-json
+Download http://localhost:4260/@denotest%2fimports-package-json
 Download http://localhost:4260/@denotest/imports-package-json/1.0.0.tgz
 error: [ERR_PACKAGE_IMPORT_NOT_DEFINED] Package import specifier "#not-defined" is not defined in package [WILDCARD]package.json imported from '[WILDCARD]import_not_defined.js'
diff --git a/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/main.out b/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/main.out
index 979e355765..70d787b251 100644
--- a/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/main.out
+++ b/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/imports-package-json
+Download http://localhost:4260/@denotest%2fimports-package-json
 Download http://localhost:4260/@denotest/imports-package-json/1.0.0.tgz
 hi
 bye
diff --git a/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/sub_path_import_not_defined.out b/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/sub_path_import_not_defined.out
index 7c803f2bf1..95524202ae 100644
--- a/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/sub_path_import_not_defined.out
+++ b/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/sub_path_import_not_defined.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/imports-package-json
+Download http://localhost:4260/@denotest%2fimports-package-json
 Download http://localhost:4260/@denotest/imports-package-json/1.0.0.tgz
 error: [ERR_PACKAGE_IMPORT_NOT_DEFINED] Package import specifier "#hi" is not defined in package [WILDCARD]sub_path[WILDCARD]package.json imported from '[WILDCARD]import_not_defined.js'
diff --git a/tests/specs/npm/info_chalk_display/__test__.jsonc b/tests/specs/npm/info_chalk_display/__test__.jsonc
index 998aa6f1db..54b5b74396 100644
--- a/tests/specs/npm/info_chalk_display/__test__.jsonc
+++ b/tests/specs/npm/info_chalk_display/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "info --quiet cjs_with_deps/main.js",
   "output": "cjs_with_deps/main_info.out",
-  "exitCode": 0,
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "exitCode": 0
 }
diff --git a/tests/specs/npm/info_chalk_display_node_modules_dir/__test__.jsonc b/tests/specs/npm/info_chalk_display_node_modules_dir/__test__.jsonc
index 1e6ef8284a..4358f64883 100644
--- a/tests/specs/npm/info_chalk_display_node_modules_dir/__test__.jsonc
+++ b/tests/specs/npm/info_chalk_display_node_modules_dir/__test__.jsonc
@@ -2,9 +2,5 @@
   "tempDir": true,
   "args": "info --quiet --node-modules-dir cjs_with_deps/main.js",
   "output": "cjs_with_deps/main_info.out",
-  "exitCode": 0,
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "exitCode": 0
 }
diff --git a/tests/specs/npm/info_chalk_json/__test__.jsonc b/tests/specs/npm/info_chalk_json/__test__.jsonc
index 12c8b9b615..c6e65db94b 100644
--- a/tests/specs/npm/info_chalk_json/__test__.jsonc
+++ b/tests/specs/npm/info_chalk_json/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "info --quiet --json cjs_with_deps/main.js",
   "output": "cjs_with_deps/main_info_json.out",
-  "exitCode": 0,
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "exitCode": 0
 }
diff --git a/tests/specs/npm/info_chalk_json/cjs_with_deps/main_info_json.out b/tests/specs/npm/info_chalk_json/cjs_with_deps/main_info_json.out
index 137b9f8ce5..2f7dde2d98 100644
--- a/tests/specs/npm/info_chalk_json/cjs_with_deps/main_info_json.out
+++ b/tests/specs/npm/info_chalk_json/cjs_with_deps/main_info_json.out
@@ -46,6 +46,16 @@
       "size": 325,
       "mediaType": "JavaScript",
       "specifier": "[WILDCARD]/main.js"
+    },
+    {
+      "kind": "npm",
+      "specifier": "npm:/chai@4.3.6",
+      "npmPackage": "chai@4.3.6"
+    },
+    {
+      "kind": "npm",
+      "specifier": "npm:/chalk@4.1.2",
+      "npmPackage": "chalk@4.1.2"
     }
   ],
   "redirects": {
@@ -58,12 +68,14 @@
       "version": "4.3.0",
       "dependencies": [
         "color-convert@2.0.1"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "assertion-error@1.1.0": {
       "name": "assertion-error",
       "version": "1.1.0",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "chai@4.3.6": {
       "name": "chai",
@@ -76,7 +88,8 @@
         "loupe@2.3.4",
         "pathval@1.1.1",
         "type-detect@4.0.8"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "chalk@4.1.2": {
       "name": "chalk",
@@ -84,65 +97,76 @@
       "dependencies": [
         "ansi-styles@4.3.0",
         "supports-color@7.2.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "check-error@1.0.2": {
       "name": "check-error",
       "version": "1.0.2",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "color-convert@2.0.1": {
       "name": "color-convert",
       "version": "2.0.1",
       "dependencies": [
         "color-name@1.1.4"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "color-name@1.1.4": {
       "name": "color-name",
       "version": "1.1.4",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "deep-eql@3.0.1": {
       "name": "deep-eql",
       "version": "3.0.1",
       "dependencies": [
         "type-detect@4.0.8"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "get-func-name@2.0.0": {
       "name": "get-func-name",
       "version": "2.0.0",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "has-flag@4.0.0": {
       "name": "has-flag",
       "version": "4.0.0",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "loupe@2.3.4": {
       "name": "loupe",
       "version": "2.3.4",
       "dependencies": [
         "get-func-name@2.0.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "pathval@1.1.1": {
       "name": "pathval",
       "version": "1.1.1",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "supports-color@7.2.0": {
       "name": "supports-color",
       "version": "7.2.0",
       "dependencies": [
         "has-flag@4.0.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "type-detect@4.0.8": {
       "name": "type-detect",
       "version": "4.0.8",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     }
   }
 }
diff --git a/tests/specs/npm/info_chalk_json_node_modules_dir/__test__.jsonc b/tests/specs/npm/info_chalk_json_node_modules_dir/__test__.jsonc
index 37b510488e..29c5e8bdff 100644
--- a/tests/specs/npm/info_chalk_json_node_modules_dir/__test__.jsonc
+++ b/tests/specs/npm/info_chalk_json_node_modules_dir/__test__.jsonc
@@ -2,9 +2,5 @@
   "tempDir": true,
   "args": "info --quiet --node-modules-dir --json cjs_with_deps/main.js",
   "output": "cjs_with_deps/main_info_json.out",
-  "exitCode": 0,
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "exitCode": 0
 }
diff --git a/tests/specs/npm/info_chalk_json_node_modules_dir/cjs_with_deps/main_info_json.out b/tests/specs/npm/info_chalk_json_node_modules_dir/cjs_with_deps/main_info_json.out
index 137b9f8ce5..2f7dde2d98 100644
--- a/tests/specs/npm/info_chalk_json_node_modules_dir/cjs_with_deps/main_info_json.out
+++ b/tests/specs/npm/info_chalk_json_node_modules_dir/cjs_with_deps/main_info_json.out
@@ -46,6 +46,16 @@
       "size": 325,
       "mediaType": "JavaScript",
       "specifier": "[WILDCARD]/main.js"
+    },
+    {
+      "kind": "npm",
+      "specifier": "npm:/chai@4.3.6",
+      "npmPackage": "chai@4.3.6"
+    },
+    {
+      "kind": "npm",
+      "specifier": "npm:/chalk@4.1.2",
+      "npmPackage": "chalk@4.1.2"
     }
   ],
   "redirects": {
@@ -58,12 +68,14 @@
       "version": "4.3.0",
       "dependencies": [
         "color-convert@2.0.1"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "assertion-error@1.1.0": {
       "name": "assertion-error",
       "version": "1.1.0",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "chai@4.3.6": {
       "name": "chai",
@@ -76,7 +88,8 @@
         "loupe@2.3.4",
         "pathval@1.1.1",
         "type-detect@4.0.8"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "chalk@4.1.2": {
       "name": "chalk",
@@ -84,65 +97,76 @@
       "dependencies": [
         "ansi-styles@4.3.0",
         "supports-color@7.2.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "check-error@1.0.2": {
       "name": "check-error",
       "version": "1.0.2",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "color-convert@2.0.1": {
       "name": "color-convert",
       "version": "2.0.1",
       "dependencies": [
         "color-name@1.1.4"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "color-name@1.1.4": {
       "name": "color-name",
       "version": "1.1.4",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "deep-eql@3.0.1": {
       "name": "deep-eql",
       "version": "3.0.1",
       "dependencies": [
         "type-detect@4.0.8"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "get-func-name@2.0.0": {
       "name": "get-func-name",
       "version": "2.0.0",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "has-flag@4.0.0": {
       "name": "has-flag",
       "version": "4.0.0",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "loupe@2.3.4": {
       "name": "loupe",
       "version": "2.3.4",
       "dependencies": [
         "get-func-name@2.0.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "pathval@1.1.1": {
       "name": "pathval",
       "version": "1.1.1",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "supports-color@7.2.0": {
       "name": "supports-color",
       "version": "7.2.0",
       "dependencies": [
         "has-flag@4.0.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "type-detect@4.0.8": {
       "name": "type-detect",
       "version": "4.0.8",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     }
   }
 }
diff --git a/tests/specs/npm/info_cli_chalk_display/__test__.jsonc b/tests/specs/npm/info_cli_chalk_display/__test__.jsonc
index 7587fbcb6e..902bb2dae6 100644
--- a/tests/specs/npm/info_cli_chalk_display/__test__.jsonc
+++ b/tests/specs/npm/info_cli_chalk_display/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "info --quiet npm:chalk@4",
   "output": "info/chalk.out",
-  "exitCode": 0,
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "exitCode": 0
 }
diff --git a/tests/specs/npm/info_cli_chalk_json/__test__.jsonc b/tests/specs/npm/info_cli_chalk_json/__test__.jsonc
index b5173fd93f..ee34abae7f 100644
--- a/tests/specs/npm/info_cli_chalk_json/__test__.jsonc
+++ b/tests/specs/npm/info_cli_chalk_json/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "info --quiet --json npm:chalk@4",
   "output": "info/chalk_json.out",
-  "exitCode": 0,
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "exitCode": 0
 }
diff --git a/tests/specs/npm/info_cli_chalk_json/info/chalk_json.out b/tests/specs/npm/info_cli_chalk_json/info/chalk_json.out
index 21fc7edf1a..fd2aa9ab0d 100644
--- a/tests/specs/npm/info_cli_chalk_json/info/chalk_json.out
+++ b/tests/specs/npm/info_cli_chalk_json/info/chalk_json.out
@@ -19,7 +19,8 @@
       "version": "4.3.0",
       "dependencies": [
         "color-convert@2.0.1"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "chalk@4.1.2": {
       "name": "chalk",
@@ -27,31 +28,36 @@
       "dependencies": [
         "ansi-styles@4.3.0",
         "supports-color@7.2.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "color-convert@2.0.1": {
       "name": "color-convert",
       "version": "2.0.1",
       "dependencies": [
         "color-name@1.1.4"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "color-name@1.1.4": {
       "name": "color-name",
       "version": "1.1.4",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "has-flag@4.0.0": {
       "name": "has-flag",
       "version": "4.0.0",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "supports-color@7.2.0": {
       "name": "supports-color",
       "version": "7.2.0",
       "dependencies": [
         "has-flag@4.0.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     }
   }
 }
diff --git a/tests/specs/npm/info_peer_deps/__test__.jsonc b/tests/specs/npm/info_peer_deps/__test__.jsonc
index e505f30774..00dfbc98b7 100644
--- a/tests/specs/npm/info_peer_deps/__test__.jsonc
+++ b/tests/specs/npm/info_peer_deps/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "info --quiet peer_deps_with_copied_folders/main.ts",
   "output": "peer_deps_with_copied_folders/main_info.out",
-  "exitCode": 0,
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "exitCode": 0
 }
diff --git a/tests/specs/npm/info_peer_deps/peer_deps_with_copied_folders/main.out b/tests/specs/npm/info_peer_deps/peer_deps_with_copied_folders/main.out
index 3c133bcde4..b7a5835577 100644
--- a/tests/specs/npm/info_peer_deps/peer_deps_with_copied_folders/main.out
+++ b/tests/specs/npm/info_peer_deps/peer_deps_with_copied_folders/main.out
@@ -1,7 +1,7 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/peer-dep-test-child
-Download http://localhost:4260/@denotest/peer-dep-test-grandchild
-Download http://localhost:4260/@denotest/peer-dep-test-peer
+Download http://localhost:4260/@denotest%2fpeer-dep-test-child
+Download http://localhost:4260/@denotest%2fpeer-dep-test-grandchild
+Download http://localhost:4260/@denotest%2fpeer-dep-test-peer
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/peer-dep-test-child/1.0.0.tgz
diff --git a/tests/specs/npm/info_peer_deps/peer_deps_with_copied_folders/main_node_modules_reload.out b/tests/specs/npm/info_peer_deps/peer_deps_with_copied_folders/main_node_modules_reload.out
index 9c81452118..18d7f7865b 100644
--- a/tests/specs/npm/info_peer_deps/peer_deps_with_copied_folders/main_node_modules_reload.out
+++ b/tests/specs/npm/info_peer_deps/peer_deps_with_copied_folders/main_node_modules_reload.out
@@ -1,7 +1,7 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/peer-dep-test-child
-Download http://localhost:4260/@denotest/peer-dep-test-grandchild
-Download http://localhost:4260/@denotest/peer-dep-test-peer
+Download http://localhost:4260/@denotest%2fpeer-dep-test-child
+Download http://localhost:4260/@denotest%2fpeer-dep-test-grandchild
+Download http://localhost:4260/@denotest%2fpeer-dep-test-peer
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/peer-dep-test-child/1.0.0.tgz
diff --git a/tests/specs/npm/info_peer_deps_json/__test__.jsonc b/tests/specs/npm/info_peer_deps_json/__test__.jsonc
index 9a630add45..5dd08c325f 100644
--- a/tests/specs/npm/info_peer_deps_json/__test__.jsonc
+++ b/tests/specs/npm/info_peer_deps_json/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "info --quiet --json peer_deps_with_copied_folders/main.ts",
   "output": "peer_deps_with_copied_folders/main_info_json.out",
-  "exitCode": 0,
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "exitCode": 0
 }
diff --git a/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main.out b/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main.out
index 3c133bcde4..b7a5835577 100644
--- a/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main.out
+++ b/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main.out
@@ -1,7 +1,7 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/peer-dep-test-child
-Download http://localhost:4260/@denotest/peer-dep-test-grandchild
-Download http://localhost:4260/@denotest/peer-dep-test-peer
+Download http://localhost:4260/@denotest%2fpeer-dep-test-child
+Download http://localhost:4260/@denotest%2fpeer-dep-test-grandchild
+Download http://localhost:4260/@denotest%2fpeer-dep-test-peer
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/peer-dep-test-child/1.0.0.tgz
diff --git a/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main_info_json.out b/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main_info_json.out
index 46cc35c650..2ee6268f55 100644
--- a/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main_info_json.out
+++ b/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main_info_json.out
@@ -1,7 +1,7 @@
 {
   "version": 1,
   "roots": [
-    "[WILDCARD]/peer_deps_with_copied_folders/main.ts"
+    "file://[WILDCARD]/main.ts"
   ],
   "modules": [
     {
@@ -46,6 +46,16 @@
       "size": 171,
       "mediaType": "TypeScript",
       "specifier": "file://[WILDCARD]/main.ts"
+    },
+    {
+      "kind": "npm",
+      "specifier": "npm:/@denotest/peer-dep-test-child@1.0.0",
+      "npmPackage": "@denotest/peer-dep-test-child@1.0.0_@denotest+peer-dep-test-peer@1.0.0"
+    },
+    {
+      "kind": "npm",
+      "specifier": "npm:/@denotest/peer-dep-test-child@2.0.0",
+      "npmPackage": "@denotest/peer-dep-test-child@2.0.0_@denotest+peer-dep-test-peer@2.0.0"
     }
   ],
   "redirects": {
@@ -59,7 +69,8 @@
       "dependencies": [
         "@denotest/peer-dep-test-grandchild@1.0.0_@denotest+peer-dep-test-peer@1.0.0",
         "@denotest/peer-dep-test-peer@1.0.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "@denotest/peer-dep-test-child@2.0.0_@denotest+peer-dep-test-peer@2.0.0": {
       "name": "@denotest/peer-dep-test-child",
@@ -67,31 +78,36 @@
       "dependencies": [
         "@denotest/peer-dep-test-grandchild@1.0.0_@denotest+peer-dep-test-peer@2.0.0",
         "@denotest/peer-dep-test-peer@2.0.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "@denotest/peer-dep-test-grandchild@1.0.0_@denotest+peer-dep-test-peer@1.0.0": {
       "name": "@denotest/peer-dep-test-grandchild",
       "version": "1.0.0",
       "dependencies": [
         "@denotest/peer-dep-test-peer@1.0.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "@denotest/peer-dep-test-grandchild@1.0.0_@denotest+peer-dep-test-peer@2.0.0": {
       "name": "@denotest/peer-dep-test-grandchild",
       "version": "1.0.0",
       "dependencies": [
         "@denotest/peer-dep-test-peer@2.0.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "@denotest/peer-dep-test-peer@1.0.0": {
       "name": "@denotest/peer-dep-test-peer",
       "version": "1.0.0",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "@denotest/peer-dep-test-peer@2.0.0": {
       "name": "@denotest/peer-dep-test-peer",
       "version": "2.0.0",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     }
   }
 }
diff --git a/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main_node_modules_reload.out b/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main_node_modules_reload.out
index 9c81452118..18d7f7865b 100644
--- a/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main_node_modules_reload.out
+++ b/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main_node_modules_reload.out
@@ -1,7 +1,7 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/peer-dep-test-child
-Download http://localhost:4260/@denotest/peer-dep-test-grandchild
-Download http://localhost:4260/@denotest/peer-dep-test-peer
+Download http://localhost:4260/@denotest%2fpeer-dep-test-child
+Download http://localhost:4260/@denotest%2fpeer-dep-test-grandchild
+Download http://localhost:4260/@denotest%2fpeer-dep-test-peer
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/peer-dep-test-child/1.0.0.tgz
diff --git a/tests/specs/npm/lifecycle_scripts/__test__.jsonc b/tests/specs/npm/lifecycle_scripts/__test__.jsonc
index b798b968ff..589c131dda 100644
--- a/tests/specs/npm/lifecycle_scripts/__test__.jsonc
+++ b/tests/specs/npm/lifecycle_scripts/__test__.jsonc
@@ -5,7 +5,7 @@
       "steps": [
         {
           "args": "cache --allow-scripts=npm:@denotest/node-addon main.js",
-          "output": "[WILDCARD]gyp info ok \n"
+          "output": "[WILDCARD]Initialize @denotest/node-addon@1.0.0: running 'install' script\n"
         },
         {
           "args": "run -A main.js",
@@ -38,7 +38,7 @@
       "steps": [
         {
           // without running scripts (should warn)
-          "args": "cache all_lifecycles.js",
+          "args": "run all_lifecycles.js",
           "output": "all_lifecycles_not_run.out"
         },
         {
@@ -51,6 +51,23 @@
         }
       ]
     },
+    "deno_run_lifecycle_scripts": {
+      "steps": [
+        {
+          // without running scripts (should warn)
+          "args": "run all_lifecycles.js",
+          "output": "all_lifecycles_not_run.out"
+        },
+        {
+          // now run scripts
+          "args": "run --allow-scripts all_lifecycles.js",
+          // this test package covers running preinstall, install, and postinstall scripts
+          // it also exercises running bin packages (esbuild in this case), using `node` in a script
+          // (with and without node-only CLI flags), and using `npx` in a script
+          "output": "all_lifecycles_deno_run.out"
+        }
+      ]
+    },
     "global_lifecycle_scripts": {
       "steps": [
         {
@@ -79,14 +96,12 @@
         {
           // without running scripts (should warn)
           "args": "run all_lifecycles.js",
-          "output": "only_warns_first1.out",
-          "exitCode": 1
+          "output": "only_warns_first1.out"
         },
         {
           // without running scripts (does not warn)
           "args": "run all_lifecycles.js",
-          "output": "only_warns_first2.out",
-          "exitCode": 1
+          "output": "only_warns_first2.out"
         },
         {
           // should warn because this is an explicit install
@@ -128,6 +143,13 @@
           // we run the install script, we should use the correct binary (relative to the package)
           "args": "cache --allow-scripts conflicting_bin.js",
           "output": "conflicting_bin.out"
+        },
+        {
+          "args": [
+            "eval",
+            "console.log(Deno.readTextFileSync('./say-hello-output.txt'))"
+          ],
+          "output": "conflicting_bin2.out"
         }
       ]
     },
diff --git a/tests/specs/npm/lifecycle_scripts/all_lifecycles.out b/tests/specs/npm/lifecycle_scripts/all_lifecycles.out
index 956c006ddc..bdbb2b08ea 100644
--- a/tests/specs/npm/lifecycle_scripts/all_lifecycles.out
+++ b/tests/specs/npm/lifecycle_scripts/all_lifecycles.out
@@ -1,14 +1,3 @@
-preinstall
-deno preinstall.js
-node preinstall.js
-install
-hello from install script
-postinstall[WILDCARD]
- _____________
-< postinstall >
- -------------
-        \   ^__^
-         \  (oo)\_______
-            (__)\       )\/\
-                ||----w |
-                ||     ||
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'preinstall' script
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'install' script
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'postinstall' script
diff --git a/tests/specs/npm/lifecycle_scripts/all_lifecycles_deno_run.out b/tests/specs/npm/lifecycle_scripts/all_lifecycles_deno_run.out
new file mode 100644
index 0000000000..5f06f6214c
--- /dev/null
+++ b/tests/specs/npm/lifecycle_scripts/all_lifecycles_deno_run.out
@@ -0,0 +1,4 @@
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'preinstall' script
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'install' script
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'postinstall' script
+value is 42
diff --git a/tests/specs/npm/lifecycle_scripts/all_lifecycles_not_run.out b/tests/specs/npm/lifecycle_scripts/all_lifecycles_not_run.out
index 09324c8452..645556b26d 100644
--- a/tests/specs/npm/lifecycle_scripts/all_lifecycles_not_run.out
+++ b/tests/specs/npm/lifecycle_scripts/all_lifecycles_not_run.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/node-lifecycle-scripts
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fnode-lifecycle-scripts
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/node-lifecycle-scripts/1.0.0.tgz
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Initialize @denotest/node-lifecycle-scripts@1.0.0
@@ -12,3 +12,4 @@ Warning The following packages contained npm lifecycle scripts (preinstall/insta
 ┠─ This may cause the packages to not work correctly.
 ┖─ To run lifecycle scripts, use the `--allow-scripts` flag with `deno install`:
    deno install --allow-scripts=npm:@denotest/node-lifecycle-scripts@1.0.0
+value is 42
diff --git a/tests/specs/npm/lifecycle_scripts/all_lifecycles_not_run_global.out b/tests/specs/npm/lifecycle_scripts/all_lifecycles_not_run_global.out
index 93b5a14cc0..1b06bccb8a 100644
--- a/tests/specs/npm/lifecycle_scripts/all_lifecycles_not_run_global.out
+++ b/tests/specs/npm/lifecycle_scripts/all_lifecycles_not_run_global.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/node-lifecycle-scripts
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fnode-lifecycle-scripts
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/node-lifecycle-scripts/1.0.0.tgz
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 [UNORDERED_END]
diff --git a/tests/specs/npm/lifecycle_scripts/conflicting_bin.out b/tests/specs/npm/lifecycle_scripts/conflicting_bin.out
index c70aafdd53..33282ee81c 100644
--- a/tests/specs/npm/lifecycle_scripts/conflicting_bin.out
+++ b/tests/specs/npm/lifecycle_scripts/conflicting_bin.out
@@ -1,13 +1,12 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/better-say-hello
-Download http://localhost:4260/@denotest/say-hello-on-install
-Download http://localhost:4260/@denotest/say-hello
+Download http://localhost:4260/@denotest%2fbetter-say-hello
+Download http://localhost:4260/@denotest%2fsay-hello-on-install
+Download http://localhost:4260/@denotest%2fsay-hello
 Download http://localhost:4260/@denotest/better-say-hello/1.0.0.tgz
 Download http://localhost:4260/@denotest/say-hello-on-install/1.0.0.tgz
 Download http://localhost:4260/@denotest/say-hello/1.0.0.tgz
 Initialize @denotest/better-say-hello@1.0.0
 Initialize @denotest/say-hello-on-install@1.0.0
 Initialize @denotest/say-hello@1.0.0
+Initialize @denotest/say-hello-on-install@1.0.0: running 'install' script
 [UNORDERED_END]
-install script
-@denotest/say-hello says hello!
diff --git a/tests/specs/npm/lifecycle_scripts/conflicting_bin2.out b/tests/specs/npm/lifecycle_scripts/conflicting_bin2.out
new file mode 100644
index 0000000000..b4640b02c5
--- /dev/null
+++ b/tests/specs/npm/lifecycle_scripts/conflicting_bin2.out
@@ -0,0 +1 @@
+@denotest/say-hello says hello!
diff --git a/tests/specs/npm/lifecycle_scripts/future_install_all_lifecycles.out b/tests/specs/npm/lifecycle_scripts/future_install_all_lifecycles.out
index f62079d3fe..bdbb2b08ea 100644
--- a/tests/specs/npm/lifecycle_scripts/future_install_all_lifecycles.out
+++ b/tests/specs/npm/lifecycle_scripts/future_install_all_lifecycles.out
@@ -1,15 +1,3 @@
-preinstall
-deno preinstall.js
-node preinstall.js
-install
-hello from install script
-postinstall
-[WILDCARD]
- _____________
-< postinstall >
- -------------
-        \   ^__^
-         \  (oo)\_______
-            (__)\       )\/\
-                ||----w |
-                ||     ||
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'preinstall' script
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'install' script
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'postinstall' script
diff --git a/tests/specs/npm/lifecycle_scripts/future_install_all_lifecycles_not_run.out b/tests/specs/npm/lifecycle_scripts/future_install_all_lifecycles_not_run.out
index 09324c8452..d72f3c8b2d 100644
--- a/tests/specs/npm/lifecycle_scripts/future_install_all_lifecycles_not_run.out
+++ b/tests/specs/npm/lifecycle_scripts/future_install_all_lifecycles_not_run.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/node-lifecycle-scripts
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fnode-lifecycle-scripts
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/node-lifecycle-scripts/1.0.0.tgz
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Initialize @denotest/node-lifecycle-scripts@1.0.0
diff --git a/tests/specs/npm/lifecycle_scripts/no_deno_json.out b/tests/specs/npm/lifecycle_scripts/no_deno_json.out
index 38a4614494..1966396a31 100644
--- a/tests/specs/npm/lifecycle_scripts/no_deno_json.out
+++ b/tests/specs/npm/lifecycle_scripts/no_deno_json.out
@@ -1,11 +1,10 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/lifecycle-scripts-cjs
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2flifecycle-scripts-cjs
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/lifecycle-scripts-cjs/1.0.0.tgz
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Initialize @denotest/lifecycle-scripts-cjs@1.0.0
 Initialize @denotest/bin@1.0.0
+Initialize @denotest/lifecycle-scripts-cjs@1.0.0: running 'preinstall' script
+Initialize @denotest/lifecycle-scripts-cjs@1.0.0: running 'install' script
 [UNORDERED_END]
-preinstall
-install
-hello from install script
diff --git a/tests/specs/npm/lifecycle_scripts/node_gyp_not_found.out b/tests/specs/npm/lifecycle_scripts/node_gyp_not_found.out
index 06c856cd94..339384f732 100644
--- a/tests/specs/npm/lifecycle_scripts/node_gyp_not_found.out
+++ b/tests/specs/npm/lifecycle_scripts/node_gyp_not_found.out
@@ -1,9 +1,12 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/node-addon-implicit-node-gyp
+Download http://localhost:4260/@denotest%2fnode-addon-implicit-node-gyp
 Download http://localhost:4260/@denotest/node-addon-implicit-node-gyp/1.0.0.tgz
 Initialize @denotest/node-addon-implicit-node-gyp@1.0.0
+Initialize @denotest/node-addon-implicit-node-gyp@1.0.0: running 'install' script
 [UNORDERED_END]
 Warning node-gyp was used in a script, but was not listed as a dependency. Either add it as a dependency or install it globally (e.g. `npm install -g node-gyp`)
-[WILDCARD]
 error: script 'install' in '@denotest/node-addon-implicit-node-gyp@1.0.0' failed with exit code 1
+stderr:
+Error launching 'node-gyp': [WILDCARD]
+
 error: failed to run scripts for packages: @denotest/node-addon-implicit-node-gyp@1.0.0
diff --git a/tests/specs/npm/lifecycle_scripts/node_gyp_not_run.out b/tests/specs/npm/lifecycle_scripts/node_gyp_not_run.out
index e0e51b26c0..da5bb4f7b5 100644
--- a/tests/specs/npm/lifecycle_scripts/node_gyp_not_run.out
+++ b/tests/specs/npm/lifecycle_scripts/node_gyp_not_run.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/node-addon
+Download http://localhost:4260/@denotest%2fnode-addon
 Download http://localhost:4260/node-gyp
 [WILDCARD]
 Warning The following packages contained npm lifecycle scripts (preinstall/install/postinstall) that were not executed:
diff --git a/tests/specs/npm/lifecycle_scripts/only_warns_first1.out b/tests/specs/npm/lifecycle_scripts/only_warns_first1.out
index 947777b5ba..645556b26d 100644
--- a/tests/specs/npm/lifecycle_scripts/only_warns_first1.out
+++ b/tests/specs/npm/lifecycle_scripts/only_warns_first1.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/node-lifecycle-scripts
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fnode-lifecycle-scripts
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/node-lifecycle-scripts/1.0.0.tgz
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Initialize @denotest/node-lifecycle-scripts@1.0.0
@@ -12,5 +12,4 @@ Warning The following packages contained npm lifecycle scripts (preinstall/insta
 ┠─ This may cause the packages to not work correctly.
 ┖─ To run lifecycle scripts, use the `--allow-scripts` flag with `deno install`:
    deno install --allow-scripts=npm:@denotest/node-lifecycle-scripts@1.0.0
-error: Uncaught SyntaxError: The requested module 'npm:@denotest/node-lifecycle-scripts' does not provide an export named 'value'
-[WILDCARD]
+value is 42
diff --git a/tests/specs/npm/lifecycle_scripts/only_warns_first2.out b/tests/specs/npm/lifecycle_scripts/only_warns_first2.out
index f6a02c7279..9e78061598 100644
--- a/tests/specs/npm/lifecycle_scripts/only_warns_first2.out
+++ b/tests/specs/npm/lifecycle_scripts/only_warns_first2.out
@@ -1,3 +1 @@
-[# note no warning]
-error: Uncaught SyntaxError: The requested module 'npm:@denotest/node-lifecycle-scripts' does not provide an export named 'value'
-[WILDCARD]
+value is 42
diff --git a/tests/specs/npm/lossy_utf8_module/main.out b/tests/specs/npm/lossy_utf8_module/main.out
index 0e96f9ebb3..d046d2ec55 100644
--- a/tests/specs/npm/lossy_utf8_module/main.out
+++ b/tests/specs/npm/lossy_utf8_module/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/lossy-utf8-module
+Download http://localhost:4260/@denotest%2flossy-utf8-module
 Download http://localhost:4260/@denotest/lossy-utf8-module/1.0.0.tgz
 ����
diff --git a/tests/specs/npm/lossy_utf8_package_json/main.out b/tests/specs/npm/lossy_utf8_package_json/main.out
index 99aa5ab61f..69f6870392 100644
--- a/tests/specs/npm/lossy_utf8_package_json/main.out
+++ b/tests/specs/npm/lossy_utf8_package_json/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/lossy-utf8-package-json
+Download http://localhost:4260/@denotest%2flossy-utf8-package-json
 Download http://localhost:4260/@denotest/lossy-utf8-package-json/1.0.0.tgz
 hello
diff --git a/tests/specs/npm/lossy_utf8_script/main.out b/tests/specs/npm/lossy_utf8_script/main.out
index 180ecdf1c3..0883392fd9 100644
--- a/tests/specs/npm/lossy_utf8_script/main.out
+++ b/tests/specs/npm/lossy_utf8_script/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/lossy-utf8-script
+Download http://localhost:4260/@denotest%2flossy-utf8-script
 Download http://localhost:4260/@denotest/lossy-utf8-script/1.0.0.tgz
 ����
diff --git a/tests/specs/npm/lossy_utf8_script_from_cjs/main.out b/tests/specs/npm/lossy_utf8_script_from_cjs/main.out
index 4f062a2aef..635ea5b3a1 100644
--- a/tests/specs/npm/lossy_utf8_script_from_cjs/main.out
+++ b/tests/specs/npm/lossy_utf8_script_from_cjs/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/lossy-utf8-script
+Download http://localhost:4260/@denotest%2flossy-utf8-script
 Download http://localhost:4260/@denotest/lossy-utf8-script/1.0.0.tgz
 Initialize @denotest/lossy-utf8-script@1.0.0
 ����
diff --git a/tests/specs/npm/mixed_case_package_name_global_dir/__test__.jsonc b/tests/specs/npm/mixed_case_package_name_global_dir/__test__.jsonc
index cc9359aab2..db980472de 100644
--- a/tests/specs/npm/mixed_case_package_name_global_dir/__test__.jsonc
+++ b/tests/specs/npm/mixed_case_package_name_global_dir/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "run mixed_case_package_name/global.ts",
   "output": "mixed_case_package_name/global.out",
-  "exitCode": 0,
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "exitCode": 0
 }
diff --git a/tests/specs/npm/mixed_case_package_name_global_dir/mixed_case_package_name/global.out b/tests/specs/npm/mixed_case_package_name_global_dir/mixed_case_package_name/global.out
index fdacea3852..a1d3a6e2c5 100644
--- a/tests/specs/npm/mixed_case_package_name_global_dir/mixed_case_package_name/global.out
+++ b/tests/specs/npm/mixed_case_package_name_global_dir/mixed_case_package_name/global.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/MixedCase
-Download http://localhost:4260/@denotest/CAPITALS
+Download http://localhost:4260/@denotest%2fMixedCase
+Download http://localhost:4260/@denotest%2fCAPITALS
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/CAPITALS/1.0.0.tgz
diff --git a/tests/specs/npm/mixed_case_package_name_global_dir/mixed_case_package_name/local.out b/tests/specs/npm/mixed_case_package_name_global_dir/mixed_case_package_name/local.out
index 6ab989d80c..c8c9ed396c 100644
--- a/tests/specs/npm/mixed_case_package_name_global_dir/mixed_case_package_name/local.out
+++ b/tests/specs/npm/mixed_case_package_name_global_dir/mixed_case_package_name/local.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/MixedCase
-Download http://localhost:4260/@denotest/CAPITALS
+Download http://localhost:4260/@denotest%2fMixedCase
+Download http://localhost:4260/@denotest%2fCAPITALS
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/CAPITALS/1.0.0.tgz
diff --git a/tests/specs/npm/mixed_case_package_name_local_dir/__test__.jsonc b/tests/specs/npm/mixed_case_package_name_local_dir/__test__.jsonc
index 1f568e2861..a214b6f4a3 100644
--- a/tests/specs/npm/mixed_case_package_name_local_dir/__test__.jsonc
+++ b/tests/specs/npm/mixed_case_package_name_local_dir/__test__.jsonc
@@ -2,9 +2,5 @@
   "tempDir": true,
   "args": "run --node-modules-dir=auto -A mixed_case_package_name/local.ts",
   "output": "mixed_case_package_name/local.out",
-  "exitCode": 0,
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "exitCode": 0
 }
diff --git a/tests/specs/npm/mixed_case_package_name_local_dir/mixed_case_package_name/global.out b/tests/specs/npm/mixed_case_package_name_local_dir/mixed_case_package_name/global.out
index fdacea3852..a1d3a6e2c5 100644
--- a/tests/specs/npm/mixed_case_package_name_local_dir/mixed_case_package_name/global.out
+++ b/tests/specs/npm/mixed_case_package_name_local_dir/mixed_case_package_name/global.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/MixedCase
-Download http://localhost:4260/@denotest/CAPITALS
+Download http://localhost:4260/@denotest%2fMixedCase
+Download http://localhost:4260/@denotest%2fCAPITALS
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/CAPITALS/1.0.0.tgz
diff --git a/tests/specs/npm/mixed_case_package_name_local_dir/mixed_case_package_name/local.out b/tests/specs/npm/mixed_case_package_name_local_dir/mixed_case_package_name/local.out
index 6ab989d80c..c8c9ed396c 100644
--- a/tests/specs/npm/mixed_case_package_name_local_dir/mixed_case_package_name/local.out
+++ b/tests/specs/npm/mixed_case_package_name_local_dir/mixed_case_package_name/local.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/MixedCase
-Download http://localhost:4260/@denotest/CAPITALS
+Download http://localhost:4260/@denotest%2fMixedCase
+Download http://localhost:4260/@denotest%2fCAPITALS
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/CAPITALS/1.0.0.tgz
diff --git a/tests/specs/npm/no_types_cjs/main.out b/tests/specs/npm/no_types_cjs/main.out
index 4747a9a325..c993d5fbf4 100644
--- a/tests/specs/npm/no_types_cjs/main.out
+++ b/tests/specs/npm/no_types_cjs/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/no-types-cjs
+Download http://localhost:4260/@denotest%2fno-types-cjs
 Download http://localhost:4260/@denotest/no-types-cjs/1.0.0.tgz
 Check file:///[WILDLINE]/no_types_cjs/main.ts
diff --git a/tests/specs/npm/no_types_in_conditional_exports/main.out b/tests/specs/npm/no_types_in_conditional_exports/main.out
index 46c5832347..593cb23370 100644
--- a/tests/specs/npm/no_types_in_conditional_exports/main.out
+++ b/tests/specs/npm/no_types_in_conditional_exports/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/no-types-in-conditional-exports
+Download http://localhost:4260/@denotest%2fno-types-in-conditional-exports
 Download http://localhost:4260/@denotest/no-types-in-conditional-exports/1.0.0.tgz
 Check [WILDCARD]npm/no_types_in_conditional_exports/main.ts
 { foo: "bar" }
diff --git a/tests/specs/npm/node_modules_deno_node_modules/__test__.jsonc b/tests/specs/npm/node_modules_deno_node_modules/__test__.jsonc
index 377fd05eab..a1fbfef7c9 100644
--- a/tests/specs/npm/node_modules_deno_node_modules/__test__.jsonc
+++ b/tests/specs/npm/node_modules_deno_node_modules/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "run --quiet node_modules_deno_node_modules/main.ts",
   "output": "node_modules_deno_node_modules/main.out",
-  "exitCode": 0,
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "exitCode": 0
 }
diff --git a/tests/specs/npm/node_modules_deno_node_modules_local/__test__.jsonc b/tests/specs/npm/node_modules_deno_node_modules_local/__test__.jsonc
index caa34f67cb..d283b758bb 100644
--- a/tests/specs/npm/node_modules_deno_node_modules_local/__test__.jsonc
+++ b/tests/specs/npm/node_modules_deno_node_modules_local/__test__.jsonc
@@ -2,9 +2,5 @@
   "tempDir": true,
   "args": "run --quiet --node-modules-dir node_modules_deno_node_modules/main.ts",
   "output": "node_modules_deno_node_modules/main.out",
-  "exitCode": 0,
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "exitCode": 0
 }
diff --git a/tests/specs/npm/node_modules_dir_require_added_node_modules_folder/__test__.jsonc b/tests/specs/npm/node_modules_dir_require_added_node_modules_folder/__test__.jsonc
index c20c929248..d0b1d081cb 100644
--- a/tests/specs/npm/node_modules_dir_require_added_node_modules_folder/__test__.jsonc
+++ b/tests/specs/npm/node_modules_dir_require_added_node_modules_folder/__test__.jsonc
@@ -2,9 +2,5 @@
   "tempDir": true,
   "args": "run --node-modules-dir=auto -A --quiet require_added_nm_folder/main.js",
   "output": "require_added_nm_folder/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/npm/node_modules_dir_require_main_entry/__test__.jsonc b/tests/specs/npm/node_modules_dir_require_main_entry/__test__.jsonc
index 1a0dfba321..a2b936d661 100644
--- a/tests/specs/npm/node_modules_dir_require_main_entry/__test__.jsonc
+++ b/tests/specs/npm/node_modules_dir_require_main_entry/__test__.jsonc
@@ -2,9 +2,5 @@
   "tempDir": true,
   "args": "run --node-modules-dir -A --quiet require_main/main.js",
   "output": "require_main/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/npm/node_modules_dir_with_deps/__test__.jsonc b/tests/specs/npm/node_modules_dir_with_deps/__test__.jsonc
index 75488e1b5d..945a3f4d4b 100644
--- a/tests/specs/npm/node_modules_dir_with_deps/__test__.jsonc
+++ b/tests/specs/npm/node_modules_dir_with_deps/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "tempDir": true,
   "args": "run --allow-read --allow-env --node-modules-dir=auto cjs_with_deps/main.js",
-  "output": "cjs_with_deps/main_node_modules.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "cjs_with_deps/main_node_modules.out"
 }
diff --git a/tests/specs/npm/node_modules_dir_yargs/__test__.jsonc b/tests/specs/npm/node_modules_dir_yargs/__test__.jsonc
index df28ea7eff..ffb9b41f82 100644
--- a/tests/specs/npm/node_modules_dir_yargs/__test__.jsonc
+++ b/tests/specs/npm/node_modules_dir_yargs/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "tempDir": true,
   "args": "run --allow-read --allow-env --node-modules-dir=auto cjs_yargs/main.js",
-  "output": "cjs_yargs/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "cjs_yargs/main.out"
 }
diff --git a/tests/specs/npm/node_modules_import/install.out b/tests/specs/npm/node_modules_import/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/npm/node_modules_import/install.out
+++ b/tests/specs/npm/node_modules_import/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/npm/node_modules_import_auto/main.out b/tests/specs/npm/node_modules_import_auto/main.out
index 8fda5cda1e..18194e3a0c 100644
--- a/tests/specs/npm/node_modules_import_auto/main.out
+++ b/tests/specs/npm/node_modules_import_auto/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 2
diff --git a/tests/specs/npm/node_modules_import_auto/main_check.out b/tests/specs/npm/node_modules_import_auto/main_check.out
index 24249f357b..093b0c051a 100644
--- a/tests/specs/npm/node_modules_import_auto/main_check.out
+++ b/tests/specs/npm/node_modules_import_auto/main_check.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 Check file:///[WILDCARD]/main.ts
diff --git a/tests/specs/npm/non_existent_dep/__test__.jsonc b/tests/specs/npm/non_existent_dep/__test__.jsonc
index a437084210..8608e00f3e 100644
--- a/tests/specs/npm/non_existent_dep/__test__.jsonc
+++ b/tests/specs/npm/non_existent_dep/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "cache npm:@denotest/non-existent-dep",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1,
-  "output": "[UNORDERED_START]\nDownload http://localhost:4260/@denotest/non-existent-dep\nDownload http://localhost:4260/@denotest/non-existent\n[UNORDERED_END]\nerror: npm package '@denotest/non-existent' does not exist.\n"
+  "output": "[UNORDERED_START]\nDownload http://localhost:4260/@denotest%2fnon-existent-dep\nDownload http://localhost:4260/@denotest%2fnon-existent\n[UNORDERED_END]\nerror: npm package '@denotest/non-existent' does not exist.\n"
 }
diff --git a/tests/specs/npm/non_existent_dep_version/__test__.jsonc b/tests/specs/npm/non_existent_dep_version/__test__.jsonc
index 19cd713e2e..dd91c66243 100644
--- a/tests/specs/npm/non_existent_dep_version/__test__.jsonc
+++ b/tests/specs/npm/non_existent_dep_version/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "cache npm:@denotest/non-existent-dep-version",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1,
-  "output": "[UNORDERED_START]\nDownload http://localhost:4260/@denotest/non-existent-dep-version\nDownload http://localhost:4260/@denotest/esm-basic\n[UNORDERED_END]\nerror: Could not find npm package '@denotest/esm-basic' matching '=99.99.99'.\n"
+  "output": "[UNORDERED_START]\nDownload http://localhost:4260/@denotest%2fnon-existent-dep-version\nDownload http://localhost:4260/@denotest%2fesm-basic\n[UNORDERED_END]\nerror: Could not find npm package '@denotest/esm-basic' matching '=99.99.99'.\n"
 }
diff --git a/tests/specs/npm/nonexistent_file/__test__.jsonc b/tests/specs/npm/nonexistent_file/__test__.jsonc
index efbda98d28..2ad137bf4a 100644
--- a/tests/specs/npm/nonexistent_file/__test__.jsonc
+++ b/tests/specs/npm/nonexistent_file/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "run -A --quiet nonexistent_file/main.js",
   "output": "nonexistent_file/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/nonexistent_file_node_modules_dir/__test__.jsonc b/tests/specs/npm/nonexistent_file_node_modules_dir/__test__.jsonc
index 66595558f1..82b282c04b 100644
--- a/tests/specs/npm/nonexistent_file_node_modules_dir/__test__.jsonc
+++ b/tests/specs/npm/nonexistent_file_node_modules_dir/__test__.jsonc
@@ -2,9 +2,5 @@
   "tempDir": true,
   "args": "run -A --quiet --node-modules-dir nonexistent_file/main.js",
   "output": "nonexistent_file/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/npmrc/__test__.jsonc b/tests/specs/npm/npmrc/__test__.jsonc
index e7588a7797..88ef2d8102 100644
--- a/tests/specs/npm/npmrc/__test__.jsonc
+++ b/tests/specs/npm/npmrc/__test__.jsonc
@@ -13,6 +13,10 @@
     "run_node_modules_dir": {
       "args": "run --node-modules-dir=auto -A --quiet main.js",
       "output": "main.out"
+    },
+    "info": {
+      "args": "info --node-modules-dir=auto --json main.js",
+      "output": "info.out"
     }
   }
 }
diff --git a/tests/specs/npm/npmrc/info.out b/tests/specs/npm/npmrc/info.out
new file mode 100644
index 0000000000..ee9aa9ee96
--- /dev/null
+++ b/tests/specs/npm/npmrc/info.out
@@ -0,0 +1,87 @@
+[UNORDERED_START]
+Download http://localhost:4262/@denotest2%2fbasic
+Download http://localhost:4261/@denotest%2fbasic
+Download http://localhost:4261/@denotest/basic/1.0.0.tgz
+Download http://localhost:4262/@denotest2/basic/1.0.0.tgz
+[UNORDERED_END]
+[UNORDERED_START]
+Initialize @denotest/basic@1.0.0
+Initialize @denotest2/basic@1.0.0
+[UNORDERED_END]
+{
+  "version": 1,
+  "roots": [
+    "file://[WILDCARD]/main.js"
+  ],
+  "modules": [
+    {
+      "kind": "esm",
+      "dependencies": [
+        {
+          "specifier": "@denotest/basic",
+          "code": {
+            "specifier": "npm:@denotest/basic@1.0.0",
+            "span": {
+              "start": {
+                "line": 0,
+                "character": 35
+              },
+              "end": {
+                "line": 0,
+                "character": 52
+              }
+            }
+          }
+        },
+        {
+          "specifier": "@denotest2/basic",
+          "code": {
+            "specifier": "npm:@denotest2/basic@1.0.0",
+            "span": {
+              "start": {
+                "line": 1,
+                "character": 22
+              },
+              "end": {
+                "line": 1,
+                "character": 40
+              }
+            }
+          }
+        }
+      ],
+      "local": "[WILDCARD]main.js",
+      "size": 192,
+      "mediaType": "JavaScript",
+      "specifier": "file://[WILDCARD]/main.js"
+    },
+    {
+      "kind": "npm",
+      "specifier": "npm:/@denotest/basic@1.0.0",
+      "npmPackage": "@denotest/basic@1.0.0"
+    },
+    {
+      "kind": "npm",
+      "specifier": "npm:/@denotest2/basic@1.0.0",
+      "npmPackage": "@denotest2/basic@1.0.0"
+    }
+  ],
+  "redirects": {
+    "npm:@denotest/basic@1.0.0": "npm:/@denotest/basic@1.0.0",
+    "npm:@denotest2/basic@1.0.0": "npm:/@denotest2/basic@1.0.0"
+  },
+  "npmPackages": {
+    "@denotest/basic@1.0.0": {
+      "name": "@denotest/basic",
+      "version": "1.0.0",
+      "dependencies": [],
+      "registryUrl": "http://localhost:4261/"
+    },
+    "@denotest2/basic@1.0.0": {
+      "name": "@denotest2/basic",
+      "version": "1.0.0",
+      "dependencies": [],
+      "registryUrl": "http://localhost:4262/"
+    }
+  }
+}
diff --git a/tests/specs/npm/npmrc/install.out b/tests/specs/npm/npmrc/install.out
index 30643527e6..f2ea78c3f8 100644
--- a/tests/specs/npm/npmrc/install.out
+++ b/tests/specs/npm/npmrc/install.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4261/@denotest/basic
-Download http://localhost:4262/@denotest2/basic
+Download http://localhost:4261/@denotest%2fbasic
+Download http://localhost:4262/@denotest2%2fbasic
 Download http://localhost:4261/@denotest/basic/1.0.0.tgz
 Download http://localhost:4262/@denotest2/basic/1.0.0.tgz
 Initialize @denotest2/basic@1.0.0
diff --git a/tests/specs/npm/npmrc_bad_registry_config/main.out b/tests/specs/npm/npmrc_bad_registry_config/main.out
index 990d4a47fa..5d778d32e9 100644
--- a/tests/specs/npm/npmrc_bad_registry_config/main.out
+++ b/tests/specs/npm/npmrc_bad_registry_config/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4261/@denotest/basic
-error: Error getting response at http://localhost:4261/@denotest/basic for package "@denotest/basic": Bad response: 401
+Download http://localhost:4261/@denotest%2fbasic
+error: Error getting response at http://localhost:4261/@denotest%2fbasic for package "@denotest/basic": Bad response: 401
 [WILDCARD]
\ No newline at end of file
diff --git a/tests/specs/npm/npmrc_bad_token/main.out b/tests/specs/npm/npmrc_bad_token/main.out
index 990d4a47fa..5d778d32e9 100644
--- a/tests/specs/npm/npmrc_bad_token/main.out
+++ b/tests/specs/npm/npmrc_bad_token/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4261/@denotest/basic
-error: Error getting response at http://localhost:4261/@denotest/basic for package "@denotest/basic": Bad response: 401
+Download http://localhost:4261/@denotest%2fbasic
+error: Error getting response at http://localhost:4261/@denotest%2fbasic for package "@denotest/basic": Bad response: 401
 [WILDCARD]
\ No newline at end of file
diff --git a/tests/specs/npm/npmrc_basic_auth/install.out b/tests/specs/npm/npmrc_basic_auth/install.out
index 30643527e6..f2ea78c3f8 100644
--- a/tests/specs/npm/npmrc_basic_auth/install.out
+++ b/tests/specs/npm/npmrc_basic_auth/install.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4261/@denotest/basic
-Download http://localhost:4262/@denotest2/basic
+Download http://localhost:4261/@denotest%2fbasic
+Download http://localhost:4262/@denotest2%2fbasic
 Download http://localhost:4261/@denotest/basic/1.0.0.tgz
 Download http://localhost:4262/@denotest2/basic/1.0.0.tgz
 Initialize @denotest2/basic@1.0.0
diff --git a/tests/specs/npm/npmrc_deno_json/main.out b/tests/specs/npm/npmrc_deno_json/main.out
index 62750088bd..c3d6be8a1a 100644
--- a/tests/specs/npm/npmrc_deno_json/main.out
+++ b/tests/specs/npm/npmrc_deno_json/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4261/@denotest/basic
+Download http://localhost:4261/@denotest%2fbasic
 Download http://localhost:4261/@denotest/basic/1.0.0.tgz
 0
 42
diff --git a/tests/specs/npm/npmrc_homedir/install.out b/tests/specs/npm/npmrc_homedir/install.out
index 30643527e6..f2ea78c3f8 100644
--- a/tests/specs/npm/npmrc_homedir/install.out
+++ b/tests/specs/npm/npmrc_homedir/install.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4261/@denotest/basic
-Download http://localhost:4262/@denotest2/basic
+Download http://localhost:4261/@denotest%2fbasic
+Download http://localhost:4262/@denotest2%2fbasic
 Download http://localhost:4261/@denotest/basic/1.0.0.tgz
 Download http://localhost:4262/@denotest2/basic/1.0.0.tgz
 Initialize @denotest2/basic@1.0.0
diff --git a/tests/specs/npm/npmrc_install_arg/.npmrc b/tests/specs/npm/npmrc_install_arg/.npmrc
new file mode 100644
index 0000000000..de3704b924
--- /dev/null
+++ b/tests/specs/npm/npmrc_install_arg/.npmrc
@@ -0,0 +1,2 @@
+@denotest:registry=http://localhost:4261/
+//localhost:4261/:_authToken=private-reg-token
diff --git a/tests/specs/npm/npmrc_install_arg/__test__.jsonc b/tests/specs/npm/npmrc_install_arg/__test__.jsonc
new file mode 100644
index 0000000000..f34cfe116a
--- /dev/null
+++ b/tests/specs/npm/npmrc_install_arg/__test__.jsonc
@@ -0,0 +1,23 @@
+{
+  "tempDir": true,
+  "tests": {
+    "deno_install_add": {
+      "steps": [{
+        "args": "install npm:@denotest/basic",
+        "output": "install.out"
+      }, {
+        "args": "run -A main.js",
+        "output": "main.out"
+      }]
+    },
+    "deno_add": {
+      "steps": [{
+        "args": "add npm:@denotest/basic",
+        "output": "add.out"
+      }, {
+        "args": "run -A main.js",
+        "output": "main.out"
+      }]
+    }
+  }
+}
diff --git a/tests/specs/npm/npmrc_install_arg/add.out b/tests/specs/npm/npmrc_install_arg/add.out
new file mode 100644
index 0000000000..11948e54d5
--- /dev/null
+++ b/tests/specs/npm/npmrc_install_arg/add.out
@@ -0,0 +1,4 @@
+Add npm:@denotest/basic@1.0.0
+Download http://localhost:4261/@denotest%2fbasic
+Download http://localhost:4261/@denotest/basic/1.0.0.tgz
+Initialize @denotest/basic@1.0.0
diff --git a/tests/specs/npm/npmrc_install_arg/install.out b/tests/specs/npm/npmrc_install_arg/install.out
new file mode 100644
index 0000000000..11948e54d5
--- /dev/null
+++ b/tests/specs/npm/npmrc_install_arg/install.out
@@ -0,0 +1,4 @@
+Add npm:@denotest/basic@1.0.0
+Download http://localhost:4261/@denotest%2fbasic
+Download http://localhost:4261/@denotest/basic/1.0.0.tgz
+Initialize @denotest/basic@1.0.0
diff --git a/tests/specs/npm/npmrc_install_arg/main.js b/tests/specs/npm/npmrc_install_arg/main.js
new file mode 100644
index 0000000000..e8ccf7611c
--- /dev/null
+++ b/tests/specs/npm/npmrc_install_arg/main.js
@@ -0,0 +1,5 @@
+import { getValue, setValue } from "@denotest/basic";
+
+console.log(getValue());
+setValue(42);
+console.log(getValue());
diff --git a/tests/specs/npm/npmrc_install_arg/main.out b/tests/specs/npm/npmrc_install_arg/main.out
new file mode 100644
index 0000000000..dcd912c89f
--- /dev/null
+++ b/tests/specs/npm/npmrc_install_arg/main.out
@@ -0,0 +1,2 @@
+0
+42
diff --git a/tests/specs/npm/npmrc_install_arg/package.json b/tests/specs/npm/npmrc_install_arg/package.json
new file mode 100644
index 0000000000..c1318b361a
--- /dev/null
+++ b/tests/specs/npm/npmrc_install_arg/package.json
@@ -0,0 +1,5 @@
+{
+  "name": "npmrc_test",
+  "version": "0.0.1",
+  "dependencies": {}
+}
diff --git a/tests/specs/npm/npmrc_no_auth/.npmrc b/tests/specs/npm/npmrc_no_auth/.npmrc
new file mode 100644
index 0000000000..860a7c3d9a
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth/.npmrc
@@ -0,0 +1 @@
+@denotest3:registry=http://localhost:4263/
diff --git a/tests/specs/npm/npmrc_no_auth/__test__.jsonc b/tests/specs/npm/npmrc_no_auth/__test__.jsonc
new file mode 100644
index 0000000000..efd04f0e46
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth/__test__.jsonc
@@ -0,0 +1,23 @@
+{
+  "tempDir": true,
+  "tests": {
+    "deno_install_arg": {
+      "steps": [{
+        "args": "install npm:@denotest3/basic",
+        "output": "install.out"
+      }, {
+        "args": "run -A main.js",
+        "output": "main.out"
+      }]
+    },
+    "deno_add_arg": {
+      "steps": [{
+        "args": "add npm:@denotest3/basic",
+        "output": "add.out"
+      }, {
+        "args": "run -A main.js",
+        "output": "main.out"
+      }]
+    }
+  }
+}
diff --git a/tests/specs/npm/npmrc_no_auth/add.out b/tests/specs/npm/npmrc_no_auth/add.out
new file mode 100644
index 0000000000..31b34da13f
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth/add.out
@@ -0,0 +1,4 @@
+Add npm:@denotest3/basic@1.0.0
+Download http://localhost:4263/@denotest3%2fbasic
+Download http://localhost:4263/@denotest3/basic/1.0.0.tgz
+Initialize @denotest3/basic@1.0.0
diff --git a/tests/specs/npm/npmrc_no_auth/install.out b/tests/specs/npm/npmrc_no_auth/install.out
new file mode 100644
index 0000000000..31b34da13f
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth/install.out
@@ -0,0 +1,4 @@
+Add npm:@denotest3/basic@1.0.0
+Download http://localhost:4263/@denotest3%2fbasic
+Download http://localhost:4263/@denotest3/basic/1.0.0.tgz
+Initialize @denotest3/basic@1.0.0
diff --git a/tests/specs/npm/npmrc_no_auth/main.js b/tests/specs/npm/npmrc_no_auth/main.js
new file mode 100644
index 0000000000..22713bb0da
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth/main.js
@@ -0,0 +1,5 @@
+import { getValue, setValue } from "@denotest3/basic";
+
+console.log(getValue());
+setValue(42);
+console.log(getValue());
diff --git a/tests/specs/npm/npmrc_no_auth/main.out b/tests/specs/npm/npmrc_no_auth/main.out
new file mode 100644
index 0000000000..dcd912c89f
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth/main.out
@@ -0,0 +1,2 @@
+0
+42
diff --git a/tests/specs/npm/npmrc_no_auth/package.json b/tests/specs/npm/npmrc_no_auth/package.json
new file mode 100644
index 0000000000..dddaaac464
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth/package.json
@@ -0,0 +1,6 @@
+{
+  "name": "npmrc_test",
+  "version": "0.0.1",
+  "dependencies": {
+  }
+}
diff --git a/tests/specs/npm/npmrc_no_auth_install/.npmrc b/tests/specs/npm/npmrc_no_auth_install/.npmrc
new file mode 100644
index 0000000000..860a7c3d9a
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth_install/.npmrc
@@ -0,0 +1 @@
+@denotest3:registry=http://localhost:4263/
diff --git a/tests/specs/npm/npmrc_no_auth_install/__test__.jsonc b/tests/specs/npm/npmrc_no_auth_install/__test__.jsonc
new file mode 100644
index 0000000000..56a598e3b9
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth_install/__test__.jsonc
@@ -0,0 +1,14 @@
+{
+  "tempDir": true,
+  "tests": {
+    "deno_install_arg": {
+      "steps": [{
+        "args": "install",
+        "output": "install.out"
+      }, {
+        "args": "run -A main.js",
+        "output": "main.out"
+      }]
+    }
+  }
+}
diff --git a/tests/specs/npm/npmrc_no_auth_install/install.out b/tests/specs/npm/npmrc_no_auth_install/install.out
new file mode 100644
index 0000000000..b82747af79
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth_install/install.out
@@ -0,0 +1,3 @@
+Download http://localhost:4263/@denotest3%2fbasic
+Download http://localhost:4263/@denotest3/basic/1.0.0.tgz
+Initialize @denotest3/basic@1.0.0
diff --git a/tests/specs/npm/npmrc_no_auth_install/main.js b/tests/specs/npm/npmrc_no_auth_install/main.js
new file mode 100644
index 0000000000..22713bb0da
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth_install/main.js
@@ -0,0 +1,5 @@
+import { getValue, setValue } from "@denotest3/basic";
+
+console.log(getValue());
+setValue(42);
+console.log(getValue());
diff --git a/tests/specs/npm/npmrc_no_auth_install/main.out b/tests/specs/npm/npmrc_no_auth_install/main.out
new file mode 100644
index 0000000000..dcd912c89f
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth_install/main.out
@@ -0,0 +1,2 @@
+0
+42
diff --git a/tests/specs/npm/npmrc_no_auth_install/package.json b/tests/specs/npm/npmrc_no_auth_install/package.json
new file mode 100644
index 0000000000..2d4fb15bae
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth_install/package.json
@@ -0,0 +1,7 @@
+{
+  "name": "npmrc_test",
+  "version": "0.0.1",
+  "dependencies": {
+    "@denotest3/basic": "1.0.0"
+  }
+}
diff --git a/tests/specs/npm/npmrc_not_next_to_package_json/main.out b/tests/specs/npm/npmrc_not_next_to_package_json/main.out
index b583868ffb..b128959a7c 100644
--- a/tests/specs/npm/npmrc_not_next_to_package_json/main.out
+++ b/tests/specs/npm/npmrc_not_next_to_package_json/main.out
@@ -2,7 +2,7 @@
 [# that serves the same packages. The important bit is the message below.]
 [WILDCARD] No .npmrc file found
 [WILDCARD]
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 [WILDCARD]
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 [WILDCARD]
diff --git a/tests/specs/npm/npmrc_password_no_username/install.out b/tests/specs/npm/npmrc_password_no_username/install.out
index d49a2ba0d8..b198bcd27e 100644
--- a/tests/specs/npm/npmrc_password_no_username/install.out
+++ b/tests/specs/npm/npmrc_password_no_username/install.out
@@ -1,3 +1,3 @@
 [UNORDERED_START]
-error: Error getting response at http://localhost:4261/@denotest/basic for package "@denotest/basic": Both the username and password must be provided for basic auth
+error: Error getting response at http://localhost:4261/@denotest%2fbasic for package "@denotest/basic": Both the username and password must be provided for basic auth
 [UNORDERED_END]
diff --git a/tests/specs/npm/npmrc_tarball_other_server/fail/main.out b/tests/specs/npm/npmrc_tarball_other_server/fail/main.out
index 08a84a477c..2c68dba54e 100644
--- a/tests/specs/npm/npmrc_tarball_other_server/fail/main.out
+++ b/tests/specs/npm/npmrc_tarball_other_server/fail/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4261/@denotest/tarballs-privateserver2
+Download http://localhost:4261/@denotest%2ftarballs-privateserver2
 Download http://localhost:4262/@denotest/tarballs-privateserver2/1.0.0.tgz
 error: Failed caching npm package '@denotest/tarballs-privateserver2@1.0.0'.
 
diff --git a/tests/specs/npm/npmrc_tarball_other_server/success/main.out b/tests/specs/npm/npmrc_tarball_other_server/success/main.out
index d75f26e336..5322a1a17d 100644
--- a/tests/specs/npm/npmrc_tarball_other_server/success/main.out
+++ b/tests/specs/npm/npmrc_tarball_other_server/success/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4261/@denotest/tarballs-privateserver2
+Download http://localhost:4261/@denotest%2ftarballs-privateserver2
 Download http://localhost:4262/@denotest/tarballs-privateserver2/1.0.0.tgz
 [# This fails on a checksum issue, because the test server isn't smart enough]
 [# to serve proper checksums for a package at another registry. That's fine]
diff --git a/tests/specs/npm/npmrc_username_no_password/install.out b/tests/specs/npm/npmrc_username_no_password/install.out
index d49a2ba0d8..b198bcd27e 100644
--- a/tests/specs/npm/npmrc_username_no_password/install.out
+++ b/tests/specs/npm/npmrc_username_no_password/install.out
@@ -1,3 +1,3 @@
 [UNORDERED_START]
-error: Error getting response at http://localhost:4261/@denotest/basic for package "@denotest/basic": Both the username and password must be provided for basic auth
+error: Error getting response at http://localhost:4261/@denotest%2fbasic for package "@denotest/basic": Both the username and password must be provided for basic auth
 [UNORDERED_END]
diff --git a/tests/specs/npm/npmrc_username_password/.npmrc b/tests/specs/npm/npmrc_username_password/.npmrc
index c318678aea..9e1ded96a3 100644
--- a/tests/specs/npm/npmrc_username_password/.npmrc
+++ b/tests/specs/npm/npmrc_username_password/.npmrc
@@ -1,6 +1,8 @@
 @denotest:registry=http://localhost:4261/
 //localhost:4261/:username=deno
-//localhost:4261/:_password=land
+# base64 of land
+//localhost:4261/:_password=bGFuZA==
 @denotest2:registry=http://localhost:4262/
 //localhost:4262/:username=deno
-//localhost:4262/:_password=land2
+# base64 of land2
+//localhost:4262/:_password=bGFuZDI=
diff --git a/tests/specs/npm/npmrc_username_password/install.out b/tests/specs/npm/npmrc_username_password/install.out
index 30643527e6..f2ea78c3f8 100644
--- a/tests/specs/npm/npmrc_username_password/install.out
+++ b/tests/specs/npm/npmrc_username_password/install.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4261/@denotest/basic
-Download http://localhost:4262/@denotest2/basic
+Download http://localhost:4261/@denotest%2fbasic
+Download http://localhost:4262/@denotest2%2fbasic
 Download http://localhost:4261/@denotest/basic/1.0.0.tgz
 Download http://localhost:4262/@denotest2/basic/1.0.0.tgz
 Initialize @denotest2/basic@1.0.0
diff --git a/tests/specs/npm/permissions_outside_package/__test__.jsonc b/tests/specs/npm/permissions_outside_package/__test__.jsonc
index 58f917f735..d5f6bf4908 100644
--- a/tests/specs/npm/permissions_outside_package/__test__.jsonc
+++ b/tests/specs/npm/permissions_outside_package/__test__.jsonc
@@ -1,8 +1,5 @@
 {
-  "args": "run --allow-read permissions_outside_package/main.ts",
-  "output": "permissions_outside_package/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "tempDir": true,
+  "args": "run --allow-read --node-modules-dir=none main.ts",
+  "output": "main.out"
 }
diff --git a/tests/specs/npm/permissions_outside_package/permissions_outside_package/foo/config.js b/tests/specs/npm/permissions_outside_package/foo/config.js
similarity index 100%
rename from tests/specs/npm/permissions_outside_package/permissions_outside_package/foo/config.js
rename to tests/specs/npm/permissions_outside_package/foo/config.js
diff --git a/tests/specs/npm/permissions_outside_package/foo/package.json b/tests/specs/npm/permissions_outside_package/foo/package.json
new file mode 100644
index 0000000000..95b43077e4
--- /dev/null
+++ b/tests/specs/npm/permissions_outside_package/foo/package.json
@@ -0,0 +1,5 @@
+{
+  "name": "foobar",
+  "version": "0.0.1",
+  "type": "commonjs"
+}
diff --git a/tests/specs/npm/permissions_outside_package/permissions_outside_package/main.out b/tests/specs/npm/permissions_outside_package/main.out
similarity index 62%
rename from tests/specs/npm/permissions_outside_package/permissions_outside_package/main.out
rename to tests/specs/npm/permissions_outside_package/main.out
index 089f329c4f..0fde8cf87f 100644
--- a/tests/specs/npm/permissions_outside_package/permissions_outside_package/main.out
+++ b/tests/specs/npm/permissions_outside_package/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/permissions-outside-package
+Download http://localhost:4260/@denotest%2fpermissions-outside-package
 Download http://localhost:4260/@denotest/permissions-outside-package/1.0.0.tgz
 { name: "foobar", version: "0.0.1" }
diff --git a/tests/specs/npm/permissions_outside_package/permissions_outside_package/main.ts b/tests/specs/npm/permissions_outside_package/main.ts
similarity index 64%
rename from tests/specs/npm/permissions_outside_package/permissions_outside_package/main.ts
rename to tests/specs/npm/permissions_outside_package/main.ts
index 934a3eebcf..a80713fa72 100644
--- a/tests/specs/npm/permissions_outside_package/permissions_outside_package/main.ts
+++ b/tests/specs/npm/permissions_outside_package/main.ts
@@ -1,5 +1,5 @@
 import { loadConfigFile } from "npm:@denotest/permissions-outside-package";
 
-const fileName = `${Deno.cwd()}/permissions_outside_package/foo/config.js`;
+const fileName = `${Deno.cwd()}/foo/config.js`;
 const config = loadConfigFile(fileName);
 console.log(config);
diff --git a/tests/specs/npm/permissions_outside_package/package.json b/tests/specs/npm/permissions_outside_package/package.json
new file mode 100644
index 0000000000..2c63c08510
--- /dev/null
+++ b/tests/specs/npm/permissions_outside_package/package.json
@@ -0,0 +1,2 @@
+{
+}
diff --git a/tests/specs/npm/permissions_outside_package/permissions_outside_package/foo/package.json b/tests/specs/npm/permissions_outside_package/permissions_outside_package/foo/package.json
deleted file mode 100644
index cc049e6ce9..0000000000
--- a/tests/specs/npm/permissions_outside_package/permissions_outside_package/foo/package.json
+++ /dev/null
@@ -1,4 +0,0 @@
-{
-  "name": "foobar",
-  "version": "0.0.1"
-}
diff --git a/tests/specs/npm/remote_npm_specifier/__test__.jsonc b/tests/specs/npm/remote_npm_specifier/__test__.jsonc
index 416024f0cd..0cf7c4c87d 100644
--- a/tests/specs/npm/remote_npm_specifier/__test__.jsonc
+++ b/tests/specs/npm/remote_npm_specifier/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "run --quiet -A remote_npm_specifier/main.ts",
   "output": "remote_npm_specifier/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/npm/require_json/__test__.jsonc b/tests/specs/npm/require_json/__test__.jsonc
index 43af6230f6..c24572f144 100644
--- a/tests/specs/npm/require_json/__test__.jsonc
+++ b/tests/specs/npm/require_json/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet require_json/main.js",
-  "output": "require_json/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "require_json/main.out"
 }
diff --git a/tests/specs/npm/require_resolve_bad_paths_global_cache/main.out b/tests/specs/npm/require_resolve_bad_paths_global_cache/main.out
index 3cc8a82794..2e82e68027 100644
--- a/tests/specs/npm/require_resolve_bad_paths_global_cache/main.out
+++ b/tests/specs/npm/require_resolve_bad_paths_global_cache/main.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/esm-basic
-Download http://localhost:4260/@denotest/require-resolve
+Download http://localhost:4260/@denotest%2fesm-basic
+Download http://localhost:4260/@denotest%2frequire-resolve
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
diff --git a/tests/specs/npm/require_type_commonjs/__test__.jsonc b/tests/specs/npm/require_type_commonjs/__test__.jsonc
index c9ba97ff52..a71173ce37 100644
--- a/tests/specs/npm/require_type_commonjs/__test__.jsonc
+++ b/tests/specs/npm/require_type_commonjs/__test__.jsonc
@@ -1,5 +1,4 @@
 {
   "args": "run --allow-read --quiet main.ts",
-  "output": "main.out",
-  "exitCode": 1
+  "output": "main.out"
 }
diff --git a/tests/specs/npm/require_type_commonjs/main.out b/tests/specs/npm/require_type_commonjs/main.out
index f7a81572c3..00750edc07 100644
--- a/tests/specs/npm/require_type_commonjs/main.out
+++ b/tests/specs/npm/require_type_commonjs/main.out
@@ -1,10 +1 @@
-error: Uncaught (in promise) SyntaxError: Unexpected token 'export'
-    at Object.evalContext (ext:core/01_core.js:[WILDCARD])
-    at wrapSafe (node:module:[WILDCARD])
-    at Module._compile (node:module:[WILDCARD])
-    at Object.Module._extensions..js (node:module:[WILDCARD])
-    at Module.load (node:module:[WILDCARD])
-    at Function.Module._load (node:module:[WILDCARD])
-    at Module.require (node:module:[WILDCARD])
-    at require (node:module:[WILDCARD])
-    at file:///[WILDCARD]/@denotest/type-commonjs/1.0.0/index.js:3:13
+3
diff --git a/tests/specs/npm/require_type_commonjs/main.ts b/tests/specs/npm/require_type_commonjs/main.ts
index 243eb216e4..95ec6099ec 100644
--- a/tests/specs/npm/require_type_commonjs/main.ts
+++ b/tests/specs/npm/require_type_commonjs/main.ts
@@ -1 +1,2 @@
-import "npm:@denotest/type-commonjs";
+import { add } from "npm:@denotest/type-commonjs";
+console.log(add(1, 2));
diff --git a/tests/specs/npm/reserved_word_exports/__test__.jsonc b/tests/specs/npm/reserved_word_exports/__test__.jsonc
index d2f6ae7c29..01d5974c38 100644
--- a/tests/specs/npm/reserved_word_exports/__test__.jsonc
+++ b/tests/specs/npm/reserved_word_exports/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run reserved_word_exports/main.ts",
-  "output": "reserved_word_exports/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "reserved_word_exports/main.out"
 }
diff --git a/tests/specs/npm/reserved_word_exports/reserved_word_exports/main.out b/tests/specs/npm/reserved_word_exports/reserved_word_exports/main.out
index ccfd35bc86..2a82194e37 100644
--- a/tests/specs/npm/reserved_word_exports/reserved_word_exports/main.out
+++ b/tests/specs/npm/reserved_word_exports/reserved_word_exports/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/reserved-word-exports
+Download http://localhost:4260/@denotest%2freserved-word-exports
 Download http://localhost:4260/@denotest/reserved-word-exports/1.0.0.tgz
 [Module: null prototype] {
   abstract: "abstract",
diff --git a/tests/specs/npm/run_existing_npm_package_with_subpath/__test__.jsonc b/tests/specs/npm/run_existing_npm_package_with_subpath/__test__.jsonc
index bb02973c4d..3509fc5adb 100644
--- a/tests/specs/npm/run_existing_npm_package_with_subpath/__test__.jsonc
+++ b/tests/specs/npm/run_existing_npm_package_with_subpath/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "tempDir": true,
   "args": "run --allow-read --node-modules-dir=auto npm:@denotest/bin/cli-esm dev --help",
-  "output": "run_existing_npm_package_with_subpath/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "run_existing_npm_package_with_subpath/main.out"
 }
diff --git a/tests/specs/npm/run_existing_npm_package_with_subpath/run_existing_npm_package_with_subpath/main.out b/tests/specs/npm/run_existing_npm_package_with_subpath/run_existing_npm_package_with_subpath/main.out
index f6ee03ef1b..a473c32cc6 100644
--- a/tests/specs/npm/run_existing_npm_package_with_subpath/run_existing_npm_package_with_subpath/main.out
+++ b/tests/specs/npm/run_existing_npm_package_with_subpath/run_existing_npm_package_with_subpath/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Initialize @denotest/bin@1.0.0
 dev
diff --git a/tests/specs/npm/sub_paths/__test__.jsonc b/tests/specs/npm/sub_paths/__test__.jsonc
index 88ccbc3ac4..4023fb197b 100644
--- a/tests/specs/npm/sub_paths/__test__.jsonc
+++ b/tests/specs/npm/sub_paths/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet sub_paths/main.jsx",
-  "output": "sub_paths/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "sub_paths/main.out"
 }
diff --git a/tests/specs/npm/tarball_with_global_header/__test__.jsonc b/tests/specs/npm/tarball_with_global_header/__test__.jsonc
index 7cf4a60830..af6f891836 100644
--- a/tests/specs/npm/tarball_with_global_header/__test__.jsonc
+++ b/tests/specs/npm/tarball_with_global_header/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet tarball_with_global_header/main.js",
-  "output": "tarball_with_global_header/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "tarball_with_global_header/main.out"
 }
diff --git a/tests/specs/npm/translate_cjs_to_esm/__test__.jsonc b/tests/specs/npm/translate_cjs_to_esm/__test__.jsonc
index e1344493cd..59f5873582 100644
--- a/tests/specs/npm/translate_cjs_to_esm/__test__.jsonc
+++ b/tests/specs/npm/translate_cjs_to_esm/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "run -A --quiet translate_cjs_to_esm/main.js",
-  "output": "translate_cjs_to_esm/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "translate_cjs_to_esm/main.out"
 }
diff --git a/tests/specs/npm/types_ambient_module/__test__.jsonc b/tests/specs/npm/types_ambient_module/__test__.jsonc
index fc60b34332..966d8d8ed4 100644
--- a/tests/specs/npm/types_ambient_module/__test__.jsonc
+++ b/tests/specs/npm/types_ambient_module/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "check --quiet types_ambient_module/main.ts",
   "output": "types_ambient_module/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/types_ambient_module_import_map/__test__.jsonc b/tests/specs/npm/types_ambient_module_import_map/__test__.jsonc
index 2e8c9b60b9..bbfa93a99b 100644
--- a/tests/specs/npm/types_ambient_module_import_map/__test__.jsonc
+++ b/tests/specs/npm/types_ambient_module_import_map/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "check --quiet --import-map=types_ambient_module/import_map.json types_ambient_module/main_import_map.ts",
   "output": "types_ambient_module/main_import_map.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/types_d_ext/__test__.jsonc b/tests/specs/npm/types_d_ext/__test__.jsonc
index daa0f26ff0..0af9e08b12 100644
--- a/tests/specs/npm/types_d_ext/__test__.jsonc
+++ b/tests/specs/npm/types_d_ext/__test__.jsonc
@@ -1,8 +1,4 @@
 {
   "args": "check --all d_ext/main.ts",
-  "output": "d_ext/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  }
+  "output": "d_ext/main.out"
 }
diff --git a/tests/specs/npm/types_d_ext/d_ext/main.out b/tests/specs/npm/types_d_ext/d_ext/main.out
index e99df66965..5a834fbeb6 100644
--- a/tests/specs/npm/types_d_ext/d_ext/main.out
+++ b/tests/specs/npm/types_d_ext/d_ext/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/d-ext
+Download http://localhost:4260/@denotest%2fd-ext
 Download http://localhost:4260/@denotest/d-ext/1.0.0.tgz
 Check file:///[WILDCARD]/d_ext/main.ts
diff --git a/tests/specs/npm/types_entry_value_not_exists/__test__.jsonc b/tests/specs/npm/types_entry_value_not_exists/__test__.jsonc
index 1c2e8735fb..5f66e8a389 100644
--- a/tests/specs/npm/types_entry_value_not_exists/__test__.jsonc
+++ b/tests/specs/npm/types_entry_value_not_exists/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "check --all types_entry_value_not_exists/main.ts",
   "output": "types_entry_value_not_exists/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/types_entry_value_not_exists/types_entry_value_not_exists/main.out b/tests/specs/npm/types_entry_value_not_exists/types_entry_value_not_exists/main.out
index 017a17ea2e..62ef51d9f1 100644
--- a/tests/specs/npm/types_entry_value_not_exists/types_entry_value_not_exists/main.out
+++ b/tests/specs/npm/types_entry_value_not_exists/types_entry_value_not_exists/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/types-entry-value-not-exists
+Download http://localhost:4260/@denotest%2ftypes-entry-value-not-exists
 Download http://localhost:4260/@denotest/types-entry-value-not-exists/1.0.0.tgz
 Check file://[WILDCARD]/types_entry_value_not_exists/main.ts
 error: TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
diff --git a/tests/specs/npm/types_exports_import_types/__test__.jsonc b/tests/specs/npm/types_exports_import_types/__test__.jsonc
index fbb6a918a2..b7dab5d3dc 100644
--- a/tests/specs/npm/types_exports_import_types/__test__.jsonc
+++ b/tests/specs/npm/types_exports_import_types/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "check --all types_exports_import_types/main.ts",
   "output": "types_exports_import_types/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/types_exports_import_types/types_exports_import_types/main.out b/tests/specs/npm/types_exports_import_types/types_exports_import_types/main.out
index 10f9425ca4..bb69bf86fb 100644
--- a/tests/specs/npm/types_exports_import_types/types_exports_import_types/main.out
+++ b/tests/specs/npm/types_exports_import_types/types_exports_import_types/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/types-exports-import-types
+Download http://localhost:4260/@denotest%2ftypes-exports-import-types
 Download http://localhost:4260/@denotest/types-exports-import-types/1.0.0.tgz
 Check file://[WILDCARD]/types_exports_import_types/main.ts
 error: TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
diff --git a/tests/specs/npm/types_general/main.out b/tests/specs/npm/types_general/main.out
index ffba4f84db..edc83f2a26 100644
--- a/tests/specs/npm/types_general/main.out
+++ b/tests/specs/npm/types_general/main.out
@@ -1,7 +1,7 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/types
-Download http://localhost:4260/@denotest/types_imported
-Download http://localhost:4260/@denotest/types-exports-subpaths
+Download http://localhost:4260/@denotest%2ftypes
+Download http://localhost:4260/@denotest%2ftypes_imported
+Download http://localhost:4260/@denotest%2ftypes-exports-subpaths
 Download http://localhost:4260/@denotest/types_imported/1.0.0.tgz
 Download http://localhost:4260/@denotest/types-exports-subpaths/1.0.0.tgz
 Download http://localhost:4260/@denotest/types/1.0.0.tgz
diff --git a/tests/specs/npm/types_no_types_entry/__test__.jsonc b/tests/specs/npm/types_no_types_entry/__test__.jsonc
index bae02f3a84..3625122bf6 100644
--- a/tests/specs/npm/types_no_types_entry/__test__.jsonc
+++ b/tests/specs/npm/types_no_types_entry/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "check --all types_no_types_entry/main.ts",
   "output": "types_no_types_entry/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/npm/types_no_types_entry/types_no_types_entry/main.out b/tests/specs/npm/types_no_types_entry/types_no_types_entry/main.out
index 53e872eaf1..c867253ad9 100644
--- a/tests/specs/npm/types_no_types_entry/types_no_types_entry/main.out
+++ b/tests/specs/npm/types_no_types_entry/types_no_types_entry/main.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/types-no-types-entry
-Download http://localhost:4260/@denotest/types-entry-value-not-exists
+Download http://localhost:4260/@denotest%2ftypes-no-types-entry
+Download http://localhost:4260/@denotest%2ftypes-entry-value-not-exists
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/types-entry-value-not-exists/1.0.0.tgz
diff --git a/tests/specs/npm/typescript_file_in_package/__test__.jsonc b/tests/specs/npm/typescript_file_in_package/__test__.jsonc
index c5bd61ca27..7b5c5e1b67 100644
--- a/tests/specs/npm/typescript_file_in_package/__test__.jsonc
+++ b/tests/specs/npm/typescript_file_in_package/__test__.jsonc
@@ -1,9 +1,5 @@
 {
-  "args": "run typescript_file_in_package/main.ts",
-  "output": "typescript_file_in_package/main.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
+  "args": "run main.ts",
+  "output": "main.out",
   "exitCode": 1
 }
diff --git a/tests/specs/npm/typescript_file_in_package/main.out b/tests/specs/npm/typescript_file_in_package/main.out
new file mode 100644
index 0000000000..58290a8737
--- /dev/null
+++ b/tests/specs/npm/typescript_file_in_package/main.out
@@ -0,0 +1,3 @@
+Download http://localhost:4260/@denotest%2ftypescript-file
+Download http://localhost:4260/@denotest/typescript-file/1.0.0.tgz
+error: TypeScript files are not supported in npm packages: file:///[WILDCARD]/@denotest/typescript-file/1.0.0/index.ts
diff --git a/tests/specs/npm/typescript_file_in_package/typescript_file_in_package/main.ts b/tests/specs/npm/typescript_file_in_package/main.ts
similarity index 100%
rename from tests/specs/npm/typescript_file_in_package/typescript_file_in_package/main.ts
rename to tests/specs/npm/typescript_file_in_package/main.ts
diff --git a/tests/specs/npm/typescript_file_in_package/typescript_file_in_package/main.out b/tests/specs/npm/typescript_file_in_package/typescript_file_in_package/main.out
deleted file mode 100644
index 3c3b971907..0000000000
--- a/tests/specs/npm/typescript_file_in_package/typescript_file_in_package/main.out
+++ /dev/null
@@ -1,6 +0,0 @@
-Download http://localhost:4260/@denotest/typescript-file
-Download http://localhost:4260/@denotest/typescript-file/1.0.0.tgz
-error: Could not resolve 'npm:@denotest/typescript-file@1.0.0'.
-
-Caused by:
-    TypeScript files are not supported in npm packages: file:///[WILDCARD]/@denotest/typescript-file/1.0.0/index.ts
diff --git a/tests/specs/npm/user_agent_env_var/__test__.jsonc b/tests/specs/npm/user_agent_env_var/__test__.jsonc
new file mode 100644
index 0000000000..a2af970a0e
--- /dev/null
+++ b/tests/specs/npm/user_agent_env_var/__test__.jsonc
@@ -0,0 +1,46 @@
+{
+  "tempDir": true,
+  "tests": {
+    "set_for_npm_package": {
+      "steps": [
+        {
+          "args": "install",
+          "output": "[WILDCARD]"
+        },
+        {
+          "args": "run -A npm:@denotest/print-npm-user-agent",
+          "output": "run.out"
+        }
+      ]
+    },
+    "unset_for_local_file": {
+      "steps": [
+        {
+          "args": "run -A main.ts",
+          "output": "Download [WILDCARD]\nnpm_config_user_agent: undefined\n"
+        }
+      ]
+    },
+    "set_for_tasks": {
+      "steps": [
+        {
+          "args": "install",
+          "output": "[WILDCARD]"
+        },
+        {
+          "args": "task run-via-bin",
+          "output": "bin_command.out"
+        }
+      ]
+    },
+    "set_for_lifecycle_scripts": {
+      "steps": [
+        {
+          "args": "install --allow-scripts",
+          "output": "postinstall.out",
+          "exitCode": 1
+        }
+      ]
+    }
+  }
+}
diff --git a/tests/specs/npm/user_agent_env_var/bin_command.out b/tests/specs/npm/user_agent_env_var/bin_command.out
new file mode 100644
index 0000000000..c8e9413038
--- /dev/null
+++ b/tests/specs/npm/user_agent_env_var/bin_command.out
@@ -0,0 +1,2 @@
+Task run-via-bin print-npm-user-agent
+npm_config_user_agent: deno/[WILDCARD] npm/? deno/[WILDCARD] [WILDCARD] [WILDCARD]
diff --git a/tests/specs/npm/user_agent_env_var/deno.jsonc b/tests/specs/npm/user_agent_env_var/deno.jsonc
new file mode 100644
index 0000000000..fbd70ec480
--- /dev/null
+++ b/tests/specs/npm/user_agent_env_var/deno.jsonc
@@ -0,0 +1,3 @@
+{
+  "nodeModulesDir": "auto"
+}
diff --git a/tests/specs/npm/user_agent_env_var/main.ts b/tests/specs/npm/user_agent_env_var/main.ts
new file mode 100644
index 0000000000..2c51107e3c
--- /dev/null
+++ b/tests/specs/npm/user_agent_env_var/main.ts
@@ -0,0 +1 @@
+console.log(`npm_config_user_agent: ${Deno.env.get("npm_config_user_agent")}`);
diff --git a/tests/specs/npm/user_agent_env_var/package.json b/tests/specs/npm/user_agent_env_var/package.json
new file mode 100644
index 0000000000..12cc0cc6fb
--- /dev/null
+++ b/tests/specs/npm/user_agent_env_var/package.json
@@ -0,0 +1,8 @@
+{
+  "scripts": {
+    "run-via-bin": "print-npm-user-agent"
+  },
+  "dependencies": {
+    "@denotest/print-npm-user-agent": "1.0.0"
+  }
+}
diff --git a/tests/specs/npm/user_agent_env_var/postinstall.out b/tests/specs/npm/user_agent_env_var/postinstall.out
new file mode 100644
index 0000000000..19a08598fb
--- /dev/null
+++ b/tests/specs/npm/user_agent_env_var/postinstall.out
@@ -0,0 +1,10 @@
+Download http://localhost:4260/@denotest%2fprint-npm-user-agent
+Download http://localhost:4260/@denotest/print-npm-user-agent/1.0.0.tgz
+Initialize @denotest/print-npm-user-agent@1.0.0
+Initialize @denotest/print-npm-user-agent@1.0.0: running 'postinstall' script
+error: script 'postinstall' in '@denotest/print-npm-user-agent@1.0.0' failed with exit code 1
+stdout:
+postinstall
+npm_config_user_agent: deno/[WILDCARD] npm/? deno/[WILDCARD] [WILDCARD] [WILDCARD]
+
+error: failed to run scripts for packages: @denotest/print-npm-user-agent@1.0.0
diff --git a/tests/specs/npm/user_agent_env_var/run.out b/tests/specs/npm/user_agent_env_var/run.out
new file mode 100644
index 0000000000..a630ac412f
--- /dev/null
+++ b/tests/specs/npm/user_agent_env_var/run.out
@@ -0,0 +1 @@
+npm_config_user_agent: deno/[WILDCARD] npm/? deno/[WILDCARD] [WILDCARD] [WILDCARD]
diff --git a/tests/specs/npm/user_agent_env_var/test.mjs b/tests/specs/npm/user_agent_env_var/test.mjs
new file mode 100644
index 0000000000..ae035d40ef
--- /dev/null
+++ b/tests/specs/npm/user_agent_env_var/test.mjs
@@ -0,0 +1 @@
+console.log(process.env.npm_config_user_agent);
diff --git a/tests/specs/npm/workspace_basic/b/main_global_cache.out b/tests/specs/npm/workspace_basic/b/main_global_cache.out
index 203ac5a991..879f6ab050 100644
--- a/tests/specs/npm/workspace_basic/b/main_global_cache.out
+++ b/tests/specs/npm/workspace_basic/b/main_global_cache.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Hello 5
 Hello 5
diff --git a/tests/specs/npm/workspace_basic/b/main_node_modules_dir.out b/tests/specs/npm/workspace_basic/b/main_node_modules_dir.out
index eeb4556526..464c05c57c 100644
--- a/tests/specs/npm/workspace_basic/b/main_node_modules_dir.out
+++ b/tests/specs/npm/workspace_basic/b/main_node_modules_dir.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 Hello 5
diff --git a/tests/specs/npm/workspace_basic/main.out b/tests/specs/npm/workspace_basic/main.out
index 92404af878..52d8267bb4 100644
--- a/tests/specs/npm/workspace_basic/main.out
+++ b/tests/specs/npm/workspace_basic/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Hello 5
 C: Hi!
diff --git a/tests/specs/permission/allow_import_worker/__test__.jsonc b/tests/specs/permission/allow_import_worker/__test__.jsonc
new file mode 100644
index 0000000000..21ac653033
--- /dev/null
+++ b/tests/specs/permission/allow_import_worker/__test__.jsonc
@@ -0,0 +1,13 @@
+{
+  "tests": {
+    "allowed": {
+      "args": "run -A --unstable-worker-options --quiet main.ts",
+      "output": "1\n"
+    },
+    "denied": {
+      "args": "run -A --unstable-worker-options --quiet main_denied.ts",
+      "output": "denied.out",
+      "exitCode": 1
+    }
+  }
+}
diff --git a/tests/specs/permission/allow_import_worker/denied.out b/tests/specs/permission/allow_import_worker/denied.out
new file mode 100644
index 0000000000..6e4dcaee09
--- /dev/null
+++ b/tests/specs/permission/allow_import_worker/denied.out
@@ -0,0 +1,7 @@
+error: Uncaught (in worker "") (in promise) TypeError: JSR package manifest for '@std/assert' failed to load. Requires import access to "127.0.0.1:4250", run again with the --allow-import flag
+await import(specifier);
+^
+    at async file:///[WILDLINE]
+error: Uncaught (in promise) Error: Unhandled error in child worker.
+    at [WILDLINE]
+    at [WILDLINE]
\ No newline at end of file
diff --git a/tests/specs/permission/allow_import_worker/main.ts b/tests/specs/permission/allow_import_worker/main.ts
new file mode 100644
index 0000000000..af65c40658
--- /dev/null
+++ b/tests/specs/permission/allow_import_worker/main.ts
@@ -0,0 +1,8 @@
+new Worker(import.meta.resolve("./worker.ts"), {
+  type: "module",
+  deno: {
+    permissions: {
+      import: ["127.0.0.1:4250"],
+    },
+  },
+});
diff --git a/tests/specs/permission/allow_import_worker/main_denied.ts b/tests/specs/permission/allow_import_worker/main_denied.ts
new file mode 100644
index 0000000000..e0d5a1d457
--- /dev/null
+++ b/tests/specs/permission/allow_import_worker/main_denied.ts
@@ -0,0 +1,8 @@
+new Worker(import.meta.resolve("./worker.ts"), {
+  type: "module",
+  deno: {
+    permissions: {
+      import: [],
+    },
+  },
+});
diff --git a/tests/specs/permission/allow_import_worker/worker.ts b/tests/specs/permission/allow_import_worker/worker.ts
new file mode 100644
index 0000000000..fd5757ba8d
--- /dev/null
+++ b/tests/specs/permission/allow_import_worker/worker.ts
@@ -0,0 +1,4 @@
+const specifier = "jsr:@std/assert/assert";
+await import(specifier);
+console.log(1);
+close();
diff --git a/tests/specs/permission/deny_run_binary_absolute_path/main.out b/tests/specs/permission/deny_run_binary_absolute_path/main.out
index fef29eae75..45b2283879 100644
--- a/tests/specs/permission/deny_run_binary_absolute_path/main.out
+++ b/tests/specs/permission/deny_run_binary_absolute_path/main.out
@@ -1,4 +1,3 @@
-Warning --allow-run without an allow list is susceptible to exploits. Prefer specifying an allow list (https://docs.deno.com/runtime/fundamentals/security/#running-subprocesses)
 NotCapable: Requires run access to "deno", run again with the --allow-run flag
     at [WILDCARD] {
   name: "NotCapable"
diff --git a/tests/specs/publish/bare_node_builtins/bare_node_builtins.out b/tests/specs/publish/bare_node_builtins/bare_node_builtins.out
index 36ba9c7ce2..6baedd906f 100644
--- a/tests/specs/publish/bare_node_builtins/bare_node_builtins.out
+++ b/tests/specs/publish/bare_node_builtins/bare_node_builtins.out
@@ -1,7 +1,7 @@
 Warning Resolving "url" as "node:url" at file:///[WILDLINE]/mod.ts:1:22. If you want to use a built-in Node module, add a "node:" prefix.
 Warning Resolving "url" as "node:url" at file:///[WILDLINE]/mod.ts:1:22. If you want to use a built-in Node module, add a "node:" prefix.
 [UNORDERED_START]
-Download http://localhost:4260/@types/node
+Download http://localhost:4260/@types%2fnode
 Download http://localhost:4260/undici-types
 Download http://localhost:4260/@types/node/node-22.5.4.tgz
 Download http://localhost:4260/undici-types/undici-types-6.19.8.tgz
diff --git a/tests/specs/publish/missing_constraint/publish.out b/tests/specs/publish/missing_constraint/publish.out
index d9fb6408fb..7d2c293c0e 100644
--- a/tests/specs/publish/missing_constraint/publish.out
+++ b/tests/specs/publish/missing_constraint/publish.out
@@ -1,7 +1,7 @@
 [UNORDERED_START]
 Download http://127.0.0.1:4250/@denotest/add/meta.json
 Download http://127.0.0.1:4250/@denotest/deps/meta.json
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://127.0.0.1:4250/@denotest/add/1.0.0_meta.json
 Download http://127.0.0.1:4250/@denotest/deps/1.0.0_meta.json
 Download http://127.0.0.1:4250/@denotest/module-graph/meta.json
diff --git a/tests/specs/publish/node_specifier/node_specifier.out b/tests/specs/publish/node_specifier/node_specifier.out
index 4c9d7cb3e2..0ba14043df 100644
--- a/tests/specs/publish/node_specifier/node_specifier.out
+++ b/tests/specs/publish/node_specifier/node_specifier.out
@@ -1,5 +1,5 @@
 [UNORDERED_START]
-Download http://localhost:4260/@types/node
+Download http://localhost:4260/@types%2fnode
 Download http://localhost:4260/undici-types
 Download http://localhost:4260/@types/node/node-22.5.4.tgz
 Download http://localhost:4260/undici-types/undici-types-6.19.8.tgz
diff --git a/tests/specs/remove/alias/__test__.jsonc b/tests/specs/remove/alias/__test__.jsonc
new file mode 100644
index 0000000000..a0c98edd90
--- /dev/null
+++ b/tests/specs/remove/alias/__test__.jsonc
@@ -0,0 +1,29 @@
+{
+  "tempDir": true,
+  "tests": {
+    "alias_with_pkg": {
+      "steps": [{
+        "args": "remove my-alias@npm:@denotest/add",
+        "output": "[WILDCARD]"
+      }, {
+        "args": [
+          "eval",
+          "console.log(Deno.readTextFileSync('package.json').trim())"
+        ],
+        "output": "package.json.out"
+      }]
+    },
+    "alias": {
+      "steps": [{
+        "args": "remove my-alias",
+        "output": "[WILDCARD]"
+      }, {
+        "args": [
+          "eval",
+          "console.log(Deno.readTextFileSync('package.json').trim())"
+        ],
+        "output": "package.json.out"
+      }]
+    }
+  }
+}
diff --git a/tests/specs/remove/alias/package.json b/tests/specs/remove/alias/package.json
new file mode 100644
index 0000000000..b6326e8bfb
--- /dev/null
+++ b/tests/specs/remove/alias/package.json
@@ -0,0 +1,5 @@
+{
+  "dependencies": {
+    "my-alias": "npm:@denotest/add@^1.0.0"
+  }
+}
diff --git a/tests/specs/remove/alias/package.json.out b/tests/specs/remove/alias/package.json.out
new file mode 100644
index 0000000000..2c63c08510
--- /dev/null
+++ b/tests/specs/remove/alias/package.json.out
@@ -0,0 +1,2 @@
+{
+}
diff --git a/tests/specs/remove/basic/__test__.jsonc b/tests/specs/remove/basic/__test__.jsonc
index fd74900b44..3ca396f8ba 100644
--- a/tests/specs/remove/basic/__test__.jsonc
+++ b/tests/specs/remove/basic/__test__.jsonc
@@ -7,7 +7,7 @@
     "args": ["eval", "console.log(Deno.readTextFileSync('deno.lock').trim())"],
     "output": "add_lock.out"
   }, {
-    "args": ["remove", "@std/assert", "@std/http"],
+    "args": ["remove", "jsr:@std/assert", "@std/http"],
     "output": "rm.out"
   }, {
     "args": ["eval", "console.log(Deno.readTextFileSync('deno.lock').trim())"],
diff --git a/tests/specs/remove/package_json/rm_add.out b/tests/specs/remove/package_json/rm_add.out
index b98c27bae6..af72f5f99d 100644
--- a/tests/specs/remove/package_json/rm_add.out
+++ b/tests/specs/remove/package_json/rm_add.out
@@ -1,4 +1,4 @@
 Removed @denotest/add
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/repl/console_log/093_console_log_format.js b/tests/specs/repl/console_log/093_console_log_format.js
new file mode 100644
index 0000000000..15022411ca
--- /dev/null
+++ b/tests/specs/repl/console_log/093_console_log_format.js
@@ -0,0 +1,16 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+class Frac {
+  constructor(num, den) {
+    this.num = num;
+    this.den = den;
+  }
+  [Symbol.toPrimitive]() {
+    return this.num / this.den;
+  }
+  display() {
+    const result = this.num / this.den;
+    process.stdout.write(`${result}`);
+  }
+}
+const f = new Frac(1, 2);
+f.display();
diff --git a/tests/specs/repl/console_log/093_console_log_format.out b/tests/specs/repl/console_log/093_console_log_format.out
new file mode 100644
index 0000000000..ea2303bc03
--- /dev/null
+++ b/tests/specs/repl/console_log/093_console_log_format.out
@@ -0,0 +1 @@
+0.5
\ No newline at end of file
diff --git a/tests/specs/repl/console_log/__test__.jsonc b/tests/specs/repl/console_log/__test__.jsonc
new file mode 100644
index 0000000000..641bc1f68a
--- /dev/null
+++ b/tests/specs/repl/console_log/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run -A --quiet 093_console_log_format.js",
+  "output": "093_console_log_format.out"
+}
diff --git a/tests/specs/run/_001_hello/001_hello.js b/tests/specs/run/_001_hello/001_hello.js
new file mode 100644
index 0000000000..accefceba6
--- /dev/null
+++ b/tests/specs/run/_001_hello/001_hello.js
@@ -0,0 +1 @@
+console.log("Hello World");
diff --git a/tests/testdata/run/001_hello.js.out b/tests/specs/run/_001_hello/001_hello.js.out
similarity index 100%
rename from tests/testdata/run/001_hello.js.out
rename to tests/specs/run/_001_hello/001_hello.js.out
diff --git a/tests/specs/run/_001_hello/__test__.jsonc b/tests/specs/run/_001_hello/__test__.jsonc
new file mode 100644
index 0000000000..4fd8126f0c
--- /dev/null
+++ b/tests/specs/run/_001_hello/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload 001_hello.js",
+  "output": "001_hello.js.out"
+}
diff --git a/tests/specs/run/_002_hello/002_hello.ts b/tests/specs/run/_002_hello/002_hello.ts
new file mode 100644
index 0000000000..accefceba6
--- /dev/null
+++ b/tests/specs/run/_002_hello/002_hello.ts
@@ -0,0 +1 @@
+console.log("Hello World");
diff --git a/tests/testdata/run/002_hello.ts.out b/tests/specs/run/_002_hello/002_hello.ts.out
similarity index 100%
rename from tests/testdata/run/002_hello.ts.out
rename to tests/specs/run/_002_hello/002_hello.ts.out
diff --git a/tests/specs/run/_002_hello/__test__.jsonc b/tests/specs/run/_002_hello/__test__.jsonc
new file mode 100644
index 0000000000..dde74d27cb
--- /dev/null
+++ b/tests/specs/run/_002_hello/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload 002_hello.ts",
+  "output": "002_hello.ts.out"
+}
diff --git a/tests/specs/run/_003_relative_import/003_relative_import.ts b/tests/specs/run/_003_relative_import/003_relative_import.ts
new file mode 100644
index 0000000000..d392f4a5d1
--- /dev/null
+++ b/tests/specs/run/_003_relative_import/003_relative_import.ts
@@ -0,0 +1,3 @@
+import { printHello } from "./print_hello.ts";
+
+printHello();
diff --git a/tests/testdata/run/005_more_imports.ts.out b/tests/specs/run/_003_relative_import/003_relative_import.ts.out
similarity index 100%
rename from tests/testdata/run/005_more_imports.ts.out
rename to tests/specs/run/_003_relative_import/003_relative_import.ts.out
diff --git a/tests/specs/run/_003_relative_import/__test__.jsonc b/tests/specs/run/_003_relative_import/__test__.jsonc
new file mode 100644
index 0000000000..7bed2c00af
--- /dev/null
+++ b/tests/specs/run/_003_relative_import/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload 003_relative_import.ts",
+  "output": "003_relative_import.ts.out"
+}
diff --git a/tests/specs/run/_003_relative_import/print_hello.ts b/tests/specs/run/_003_relative_import/print_hello.ts
new file mode 100644
index 0000000000..b9c0ad5275
--- /dev/null
+++ b/tests/specs/run/_003_relative_import/print_hello.ts
@@ -0,0 +1,3 @@
+export function printHello() {
+  console.log("Hello");
+}
diff --git a/tests/testdata/run/004_set_timeout.ts b/tests/specs/run/_004_set_timeout/004_set_timeout.ts
similarity index 100%
rename from tests/testdata/run/004_set_timeout.ts
rename to tests/specs/run/_004_set_timeout/004_set_timeout.ts
diff --git a/tests/testdata/run/004_set_timeout.ts.out b/tests/specs/run/_004_set_timeout/004_set_timeout.ts.out
similarity index 100%
rename from tests/testdata/run/004_set_timeout.ts.out
rename to tests/specs/run/_004_set_timeout/004_set_timeout.ts.out
diff --git a/tests/specs/run/_004_set_timeout/__test__.jsonc b/tests/specs/run/_004_set_timeout/__test__.jsonc
new file mode 100644
index 0000000000..6904dc0935
--- /dev/null
+++ b/tests/specs/run/_004_set_timeout/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload 004_set_timeout.ts",
+  "output": "004_set_timeout.ts.out"
+}
diff --git a/tests/testdata/run/005_more_imports.ts b/tests/specs/run/_005_more_imports/005_more_imports.ts
similarity index 65%
rename from tests/testdata/run/005_more_imports.ts
rename to tests/specs/run/_005_more_imports/005_more_imports.ts
index 6c96fac64c..c69556be15 100644
--- a/tests/testdata/run/005_more_imports.ts
+++ b/tests/specs/run/_005_more_imports/005_more_imports.ts
@@ -1,4 +1,4 @@
-import { printHello3, returnsFoo2, returnsHi } from "../subdir/mod1.ts";
+import { printHello3, returnsFoo2, returnsHi } from "./mod1.ts";
 
 printHello3();
 
diff --git a/tests/testdata/run/013_dynamic_import.ts.out b/tests/specs/run/_005_more_imports/005_more_imports.ts.out
similarity index 100%
rename from tests/testdata/run/013_dynamic_import.ts.out
rename to tests/specs/run/_005_more_imports/005_more_imports.ts.out
diff --git a/tests/specs/run/_005_more_imports/__test__.jsonc b/tests/specs/run/_005_more_imports/__test__.jsonc
new file mode 100644
index 0000000000..159a0265a8
--- /dev/null
+++ b/tests/specs/run/_005_more_imports/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload 005_more_imports.ts",
+  "output": "005_more_imports.ts.out"
+}
diff --git a/tests/specs/run/_005_more_imports/mod1.ts b/tests/specs/run/_005_more_imports/mod1.ts
new file mode 100644
index 0000000000..5e58f432ed
--- /dev/null
+++ b/tests/specs/run/_005_more_imports/mod1.ts
@@ -0,0 +1,17 @@
+import { printHello2, returnsFoo } from "./subdir2/mod2.ts";
+
+export function returnsHi(): string {
+  return "Hi";
+}
+
+export function returnsFoo2(): string {
+  return returnsFoo();
+}
+
+export function printHello3() {
+  printHello2();
+}
+
+export function throwsError() {
+  throw Error("exception from mod1");
+}
diff --git a/tests/specs/run/_005_more_imports/print_hello.ts b/tests/specs/run/_005_more_imports/print_hello.ts
new file mode 100644
index 0000000000..b9c0ad5275
--- /dev/null
+++ b/tests/specs/run/_005_more_imports/print_hello.ts
@@ -0,0 +1,3 @@
+export function printHello() {
+  console.log("Hello");
+}
diff --git a/tests/specs/run/_005_more_imports/subdir2/mod2.ts b/tests/specs/run/_005_more_imports/subdir2/mod2.ts
new file mode 100644
index 0000000000..9071d0aeb4
--- /dev/null
+++ b/tests/specs/run/_005_more_imports/subdir2/mod2.ts
@@ -0,0 +1,9 @@
+import { printHello } from "../print_hello.ts";
+
+export function returnsFoo(): string {
+  return "Foo";
+}
+
+export function printHello2() {
+  printHello();
+}
diff --git a/tests/specs/run/_006_url_imports/006_url_imports.ts b/tests/specs/run/_006_url_imports/006_url_imports.ts
new file mode 100644
index 0000000000..4036f27ed8
--- /dev/null
+++ b/tests/specs/run/_006_url_imports/006_url_imports.ts
@@ -0,0 +1,3 @@
+import { printHello } from "http://localhost:4545/subdir/mod2.ts";
+printHello();
+console.log("success");
diff --git a/tests/specs/run/_006_url_imports/006_url_imports.ts.out b/tests/specs/run/_006_url_imports/006_url_imports.ts.out
new file mode 100644
index 0000000000..989ce33e93
--- /dev/null
+++ b/tests/specs/run/_006_url_imports/006_url_imports.ts.out
@@ -0,0 +1,2 @@
+Hello
+success
diff --git a/tests/specs/run/_006_url_imports/__test__.jsonc b/tests/specs/run/_006_url_imports/__test__.jsonc
new file mode 100644
index 0000000000..50c0379ab9
--- /dev/null
+++ b/tests/specs/run/_006_url_imports/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-import 006_url_imports.ts",
+  "output": "006_url_imports.ts.out"
+}
diff --git a/tests/specs/run/_006_url_imports/print_hello.ts b/tests/specs/run/_006_url_imports/print_hello.ts
new file mode 100644
index 0000000000..b9c0ad5275
--- /dev/null
+++ b/tests/specs/run/_006_url_imports/print_hello.ts
@@ -0,0 +1,3 @@
+export function printHello() {
+  console.log("Hello");
+}
diff --git a/tests/specs/run/_006_url_imports/subdir2/mod2.ts b/tests/specs/run/_006_url_imports/subdir2/mod2.ts
new file mode 100644
index 0000000000..9071d0aeb4
--- /dev/null
+++ b/tests/specs/run/_006_url_imports/subdir2/mod2.ts
@@ -0,0 +1,9 @@
+import { printHello } from "../print_hello.ts";
+
+export function returnsFoo(): string {
+  return "Foo";
+}
+
+export function printHello2() {
+  printHello();
+}
diff --git a/tests/testdata/run/012_async.ts b/tests/specs/run/_012_async/012_async.ts
similarity index 100%
rename from tests/testdata/run/012_async.ts
rename to tests/specs/run/_012_async/012_async.ts
diff --git a/tests/testdata/run/012_async.ts.out b/tests/specs/run/_012_async/012_async.ts.out
similarity index 100%
rename from tests/testdata/run/012_async.ts.out
rename to tests/specs/run/_012_async/012_async.ts.out
diff --git a/tests/specs/run/_012_async/__test__.jsonc b/tests/specs/run/_012_async/__test__.jsonc
new file mode 100644
index 0000000000..2778f04847
--- /dev/null
+++ b/tests/specs/run/_012_async/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload 012_async.ts",
+  "output": "012_async.ts.out"
+}
diff --git a/tests/specs/run/_013_dynamic_import/013_dynamic_import.ts b/tests/specs/run/_013_dynamic_import/013_dynamic_import.ts
new file mode 100644
index 0000000000..5e73b6eb79
--- /dev/null
+++ b/tests/specs/run/_013_dynamic_import/013_dynamic_import.ts
@@ -0,0 +1,15 @@
+(async () => {
+  const { returnsHi, returnsFoo2, printHello3 } = await import(
+    "./mod1.ts"
+  );
+
+  printHello3();
+
+  if (returnsHi() !== "Hi") {
+    throw Error("Unexpected");
+  }
+
+  if (returnsFoo2() !== "Foo") {
+    throw Error("Unexpected");
+  }
+})();
diff --git a/tests/testdata/run/015_duplicate_parallel_import.js.out b/tests/specs/run/_013_dynamic_import/013_dynamic_import.ts.out
similarity index 100%
rename from tests/testdata/run/015_duplicate_parallel_import.js.out
rename to tests/specs/run/_013_dynamic_import/013_dynamic_import.ts.out
diff --git a/tests/specs/run/_013_dynamic_import/__test__.jsonc b/tests/specs/run/_013_dynamic_import/__test__.jsonc
new file mode 100644
index 0000000000..8be2c975bd
--- /dev/null
+++ b/tests/specs/run/_013_dynamic_import/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-read 013_dynamic_import.ts",
+  "output": "013_dynamic_import.ts.out"
+}
diff --git a/tests/specs/run/_013_dynamic_import/mod1.ts b/tests/specs/run/_013_dynamic_import/mod1.ts
new file mode 100644
index 0000000000..5e58f432ed
--- /dev/null
+++ b/tests/specs/run/_013_dynamic_import/mod1.ts
@@ -0,0 +1,17 @@
+import { printHello2, returnsFoo } from "./subdir2/mod2.ts";
+
+export function returnsHi(): string {
+  return "Hi";
+}
+
+export function returnsFoo2(): string {
+  return returnsFoo();
+}
+
+export function printHello3() {
+  printHello2();
+}
+
+export function throwsError() {
+  throw Error("exception from mod1");
+}
diff --git a/tests/specs/run/_013_dynamic_import/print_hello.ts b/tests/specs/run/_013_dynamic_import/print_hello.ts
new file mode 100644
index 0000000000..b9c0ad5275
--- /dev/null
+++ b/tests/specs/run/_013_dynamic_import/print_hello.ts
@@ -0,0 +1,3 @@
+export function printHello() {
+  console.log("Hello");
+}
diff --git a/tests/specs/run/_013_dynamic_import/subdir2/mod2.ts b/tests/specs/run/_013_dynamic_import/subdir2/mod2.ts
new file mode 100644
index 0000000000..9071d0aeb4
--- /dev/null
+++ b/tests/specs/run/_013_dynamic_import/subdir2/mod2.ts
@@ -0,0 +1,9 @@
+import { printHello } from "../print_hello.ts";
+
+export function returnsFoo(): string {
+  return "Foo";
+}
+
+export function printHello2() {
+  printHello();
+}
diff --git a/tests/specs/run/_014_duplicate_import/014_duplicate_import.ts b/tests/specs/run/_014_duplicate_import/014_duplicate_import.ts
new file mode 100644
index 0000000000..b996ca8aef
--- /dev/null
+++ b/tests/specs/run/_014_duplicate_import/014_duplicate_import.ts
@@ -0,0 +1,9 @@
+// with all the imports of the same module, the module should only be
+// instantiated once
+import "./auto_print_hello.ts";
+
+import "./auto_print_hello.ts";
+
+(async () => {
+  await import("./auto_print_hello.ts");
+})();
diff --git a/tests/testdata/run/014_duplicate_import.ts.out b/tests/specs/run/_014_duplicate_import/014_duplicate_import.ts.out
similarity index 100%
rename from tests/testdata/run/014_duplicate_import.ts.out
rename to tests/specs/run/_014_duplicate_import/014_duplicate_import.ts.out
diff --git a/tests/specs/run/_014_duplicate_import/__test__.jsonc b/tests/specs/run/_014_duplicate_import/__test__.jsonc
new file mode 100644
index 0000000000..7172fc1833
--- /dev/null
+++ b/tests/specs/run/_014_duplicate_import/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-read 014_duplicate_import.ts ",
+  "output": "014_duplicate_import.ts.out"
+}
diff --git a/tests/specs/run/_014_duplicate_import/auto_print_hello.ts b/tests/specs/run/_014_duplicate_import/auto_print_hello.ts
new file mode 100644
index 0000000000..5efa72e03f
--- /dev/null
+++ b/tests/specs/run/_014_duplicate_import/auto_print_hello.ts
@@ -0,0 +1,2 @@
+console.log("hello!");
+export default {};
diff --git a/tests/testdata/run/015_duplicate_parallel_import.js b/tests/specs/run/_015_duplicate_parallel_import/015_duplicate_parallel_import.js
similarity index 91%
rename from tests/testdata/run/015_duplicate_parallel_import.js
rename to tests/specs/run/_015_duplicate_parallel_import/015_duplicate_parallel_import.js
index 2fbe2c732e..136d80f462 100644
--- a/tests/testdata/run/015_duplicate_parallel_import.js
+++ b/tests/specs/run/_015_duplicate_parallel_import/015_duplicate_parallel_import.js
@@ -3,7 +3,7 @@
 
 const promises = new Array(100)
   .fill(null)
-  .map(() => import("../subdir/mod1.ts"));
+  .map(() => import("./mod1.ts"));
 
 Promise.all(promises).then((imports) => {
   const mod = imports.reduce((first, cur) => {
diff --git a/tests/testdata/run/017_import_redirect.ts.out b/tests/specs/run/_015_duplicate_parallel_import/015_duplicate_parallel_import.js.out
similarity index 100%
rename from tests/testdata/run/017_import_redirect.ts.out
rename to tests/specs/run/_015_duplicate_parallel_import/015_duplicate_parallel_import.js.out
diff --git a/tests/specs/run/_015_duplicate_parallel_import/__test__.jsonc b/tests/specs/run/_015_duplicate_parallel_import/__test__.jsonc
new file mode 100644
index 0000000000..44fe479e29
--- /dev/null
+++ b/tests/specs/run/_015_duplicate_parallel_import/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-read 015_duplicate_parallel_import.js",
+  "output": "015_duplicate_parallel_import.js.out"
+}
diff --git a/tests/specs/run/_015_duplicate_parallel_import/mod1.ts b/tests/specs/run/_015_duplicate_parallel_import/mod1.ts
new file mode 100644
index 0000000000..5e58f432ed
--- /dev/null
+++ b/tests/specs/run/_015_duplicate_parallel_import/mod1.ts
@@ -0,0 +1,17 @@
+import { printHello2, returnsFoo } from "./subdir2/mod2.ts";
+
+export function returnsHi(): string {
+  return "Hi";
+}
+
+export function returnsFoo2(): string {
+  return returnsFoo();
+}
+
+export function printHello3() {
+  printHello2();
+}
+
+export function throwsError() {
+  throw Error("exception from mod1");
+}
diff --git a/tests/specs/run/_015_duplicate_parallel_import/print_hello.ts b/tests/specs/run/_015_duplicate_parallel_import/print_hello.ts
new file mode 100644
index 0000000000..b9c0ad5275
--- /dev/null
+++ b/tests/specs/run/_015_duplicate_parallel_import/print_hello.ts
@@ -0,0 +1,3 @@
+export function printHello() {
+  console.log("Hello");
+}
diff --git a/tests/specs/run/_015_duplicate_parallel_import/subdir2/mod2.ts b/tests/specs/run/_015_duplicate_parallel_import/subdir2/mod2.ts
new file mode 100644
index 0000000000..9071d0aeb4
--- /dev/null
+++ b/tests/specs/run/_015_duplicate_parallel_import/subdir2/mod2.ts
@@ -0,0 +1,9 @@
+import { printHello } from "../print_hello.ts";
+
+export function returnsFoo(): string {
+  return "Foo";
+}
+
+export function printHello2() {
+  printHello();
+}
diff --git a/tests/testdata/run/016_double_await.ts b/tests/specs/run/_016_double_await/016_double_await.ts
similarity index 100%
rename from tests/testdata/run/016_double_await.ts
rename to tests/specs/run/_016_double_await/016_double_await.ts
diff --git a/tests/testdata/run/016_double_await.ts.out b/tests/specs/run/_016_double_await/016_double_await.ts.out
similarity index 100%
rename from tests/testdata/run/016_double_await.ts.out
rename to tests/specs/run/_016_double_await/016_double_await.ts.out
diff --git a/tests/specs/run/_016_double_await/__test__.jsonc b/tests/specs/run/_016_double_await/__test__.jsonc
new file mode 100644
index 0000000000..9ff2027168
--- /dev/null
+++ b/tests/specs/run/_016_double_await/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --allow-read --reload 016_double_await.ts",
+  "output": "016_double_await.ts.out"
+}
diff --git a/tests/specs/run/_017_import_redirect/017_import_redirect.ts b/tests/specs/run/_017_import_redirect/017_import_redirect.ts
new file mode 100644
index 0000000000..1265dd4edc
--- /dev/null
+++ b/tests/specs/run/_017_import_redirect/017_import_redirect.ts
@@ -0,0 +1,4 @@
+// http -> https redirect would happen:
+import { printHello } from "http://gist.githubusercontent.com/ry/f12b2aa3409e6b52645bc346a9e22929/raw/79318f239f51d764384a8bded8d7c6a833610dde/print_hello.ts";
+
+printHello();
diff --git a/tests/testdata/run/https_import.ts.out b/tests/specs/run/_017_import_redirect/017_import_redirect.ts.out
similarity index 100%
rename from tests/testdata/run/https_import.ts.out
rename to tests/specs/run/_017_import_redirect/017_import_redirect.ts.out
diff --git a/tests/specs/run/_017_import_redirect/__test__.jsonc b/tests/specs/run/_017_import_redirect/__test__.jsonc
new file mode 100644
index 0000000000..dd5442dcd1
--- /dev/null
+++ b/tests/specs/run/_017_import_redirect/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --allow-import --reload --check 017_import_redirect.ts",
+  "output": "017_import_redirect.ts.out"
+}
diff --git a/tests/specs/run/_017_import_redirect_check/017_import_redirect.ts b/tests/specs/run/_017_import_redirect_check/017_import_redirect.ts
new file mode 100644
index 0000000000..1265dd4edc
--- /dev/null
+++ b/tests/specs/run/_017_import_redirect_check/017_import_redirect.ts
@@ -0,0 +1,4 @@
+// http -> https redirect would happen:
+import { printHello } from "http://gist.githubusercontent.com/ry/f12b2aa3409e6b52645bc346a9e22929/raw/79318f239f51d764384a8bded8d7c6a833610dde/print_hello.ts";
+
+printHello();
diff --git a/tests/testdata/run/import_blob_url_imports.ts.out b/tests/specs/run/_017_import_redirect_check/017_import_redirect.ts.out
similarity index 100%
rename from tests/testdata/run/import_blob_url_imports.ts.out
rename to tests/specs/run/_017_import_redirect_check/017_import_redirect.ts.out
diff --git a/tests/specs/run/_017_import_redirect_check/__test__.jsonc b/tests/specs/run/_017_import_redirect_check/__test__.jsonc
new file mode 100644
index 0000000000..dd5442dcd1
--- /dev/null
+++ b/tests/specs/run/_017_import_redirect_check/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --allow-import --reload --check 017_import_redirect.ts",
+  "output": "017_import_redirect.ts.out"
+}
diff --git a/tests/specs/run/_017_import_redirect_info/017_import_redirect.ts b/tests/specs/run/_017_import_redirect_info/017_import_redirect.ts
new file mode 100644
index 0000000000..1265dd4edc
--- /dev/null
+++ b/tests/specs/run/_017_import_redirect_info/017_import_redirect.ts
@@ -0,0 +1,4 @@
+// http -> https redirect would happen:
+import { printHello } from "http://gist.githubusercontent.com/ry/f12b2aa3409e6b52645bc346a9e22929/raw/79318f239f51d764384a8bded8d7c6a833610dde/print_hello.ts";
+
+printHello();
diff --git a/tests/testdata/run/017_import_redirect_info.out b/tests/specs/run/_017_import_redirect_info/017_import_redirect_info.out
similarity index 100%
rename from tests/testdata/run/017_import_redirect_info.out
rename to tests/specs/run/_017_import_redirect_info/017_import_redirect_info.out
diff --git a/tests/specs/run/_017_import_redirect_info/__test__.jsonc b/tests/specs/run/_017_import_redirect_info/__test__.jsonc
new file mode 100644
index 0000000000..d23e8dd998
--- /dev/null
+++ b/tests/specs/run/_017_import_redirect_info/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "info --quiet --allow-import --reload 017_import_redirect.ts",
+  "output": "017_import_redirect_info.out"
+}
diff --git a/tests/specs/run/_017_import_redirect_vendor_dir/017_import_redirect.ts b/tests/specs/run/_017_import_redirect_vendor_dir/017_import_redirect.ts
new file mode 100644
index 0000000000..1265dd4edc
--- /dev/null
+++ b/tests/specs/run/_017_import_redirect_vendor_dir/017_import_redirect.ts
@@ -0,0 +1,4 @@
+// http -> https redirect would happen:
+import { printHello } from "http://gist.githubusercontent.com/ry/f12b2aa3409e6b52645bc346a9e22929/raw/79318f239f51d764384a8bded8d7c6a833610dde/print_hello.ts";
+
+printHello();
diff --git a/tests/testdata/run/import_data_url_imports.ts.out b/tests/specs/run/_017_import_redirect_vendor_dir/017_import_redirect.ts.out
similarity index 100%
rename from tests/testdata/run/import_data_url_imports.ts.out
rename to tests/specs/run/_017_import_redirect_vendor_dir/017_import_redirect.ts.out
diff --git a/tests/specs/run/_017_import_redirect_vendor_dir/__test__.jsonc b/tests/specs/run/_017_import_redirect_vendor_dir/__test__.jsonc
new file mode 100644
index 0000000000..dd5442dcd1
--- /dev/null
+++ b/tests/specs/run/_017_import_redirect_vendor_dir/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --allow-import --reload --check 017_import_redirect.ts",
+  "output": "017_import_redirect.ts.out"
+}
diff --git a/tests/testdata/run/018_async_catch.ts b/tests/specs/run/_018_async_catch/018_async_catch.ts
similarity index 100%
rename from tests/testdata/run/018_async_catch.ts
rename to tests/specs/run/_018_async_catch/018_async_catch.ts
diff --git a/tests/testdata/run/018_async_catch.ts.out b/tests/specs/run/_018_async_catch/018_async_catch.ts.out
similarity index 100%
rename from tests/testdata/run/018_async_catch.ts.out
rename to tests/specs/run/_018_async_catch/018_async_catch.ts.out
diff --git a/tests/specs/run/_018_async_catch/__test__.jsonc b/tests/specs/run/_018_async_catch/__test__.jsonc
new file mode 100644
index 0000000000..7995c79fdb
--- /dev/null
+++ b/tests/specs/run/_018_async_catch/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload 018_async_catch.ts",
+  "output": "018_async_catch.ts.out"
+}
diff --git a/tests/specs/run/_019_media_types/019_media_types.ts b/tests/specs/run/_019_media_types/019_media_types.ts
new file mode 100644
index 0000000000..d985bd2496
--- /dev/null
+++ b/tests/specs/run/_019_media_types/019_media_types.ts
@@ -0,0 +1,24 @@
+// When run against the test HTTP server, it will serve different media types
+// based on the URL containing `.t#.` strings, which exercises the different
+// mapping of media types end to end.
+
+import { loaded as loadedTs1 } from "http://localhost:4545/subdir/mt_text_typescript.t1.ts";
+import { loaded as loadedTs2 } from "http://localhost:4545/subdir/mt_video_vdn.t2.ts";
+import { loaded as loadedTs3 } from "http://localhost:4545/subdir/mt_video_mp2t.t3.ts";
+import { loaded as loadedTs4 } from "http://localhost:4545/subdir/mt_application_x_typescript.t4.ts";
+import { loaded as loadedJs1 } from "http://localhost:4545/subdir/mt_text_javascript.j1.js";
+import { loaded as loadedJs2 } from "http://localhost:4545/subdir/mt_application_ecmascript.j2.js";
+import { loaded as loadedJs3 } from "http://localhost:4545/subdir/mt_text_ecmascript.j3.js";
+import { loaded as loadedJs4 } from "http://localhost:4545/subdir/mt_application_x_javascript.j4.js";
+
+console.log(
+  "success",
+  loadedTs1,
+  loadedTs2,
+  loadedTs3,
+  loadedTs4,
+  loadedJs1,
+  loadedJs2,
+  loadedJs3,
+  loadedJs4,
+);
diff --git a/tests/testdata/run/019_media_types.ts.out b/tests/specs/run/_019_media_types/019_media_types.ts.out
similarity index 100%
rename from tests/testdata/run/019_media_types.ts.out
rename to tests/specs/run/_019_media_types/019_media_types.ts.out
diff --git a/tests/specs/run/_019_media_types/__test__.jsonc b/tests/specs/run/_019_media_types/__test__.jsonc
new file mode 100644
index 0000000000..b741a0bf22
--- /dev/null
+++ b/tests/specs/run/_019_media_types/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload --allow-import 019_media_types.ts",
+  "output": "019_media_types.ts.out"
+}
diff --git a/tests/specs/run/_020_json_modules/020_json_modules.ts b/tests/specs/run/_020_json_modules/020_json_modules.ts
new file mode 100644
index 0000000000..bde024cf86
--- /dev/null
+++ b/tests/specs/run/_020_json_modules/020_json_modules.ts
@@ -0,0 +1,2 @@
+import config from "./config.json";
+console.log(JSON.stringify(config));
diff --git a/tests/testdata/run/020_json_modules.ts.out b/tests/specs/run/_020_json_modules/020_json_modules.ts.out
similarity index 80%
rename from tests/testdata/run/020_json_modules.ts.out
rename to tests/specs/run/_020_json_modules/020_json_modules.ts.out
index 948901724a..8bf0b41465 100644
--- a/tests/testdata/run/020_json_modules.ts.out
+++ b/tests/specs/run/_020_json_modules/020_json_modules.ts.out
@@ -1,3 +1,3 @@
 error: Expected a JavaScript or TypeScript module, but identified a Json module. Consider importing Json modules with an import attribute with the type of "json".
-  Specifier: [WILDCARD]/subdir/config.json
+  Specifier: [WILDCARD]/config.json
 [WILDCARD]
\ No newline at end of file
diff --git a/tests/specs/run/_020_json_modules/__test__.jsonc b/tests/specs/run/_020_json_modules/__test__.jsonc
new file mode 100644
index 0000000000..618616438a
--- /dev/null
+++ b/tests/specs/run/_020_json_modules/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload 020_json_modules.ts",
+  "output": "020_json_modules.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/_020_json_modules/config.json b/tests/specs/run/_020_json_modules/config.json
new file mode 100644
index 0000000000..01c3b5e79a
--- /dev/null
+++ b/tests/specs/run/_020_json_modules/config.json
@@ -0,0 +1,6 @@
+{
+  "foo": {
+    "bar": true,
+    "baz": ["qat", 1]
+  }
+}
diff --git a/tests/specs/run/_021_mjs_modules/021_mjs_modules.ts b/tests/specs/run/_021_mjs_modules/021_mjs_modules.ts
new file mode 100644
index 0000000000..326fce3e51
--- /dev/null
+++ b/tests/specs/run/_021_mjs_modules/021_mjs_modules.ts
@@ -0,0 +1,2 @@
+import { isMod5 } from "./mod5.mjs";
+console.log(isMod5);
diff --git a/tests/testdata/run/021_mjs_modules.ts.out b/tests/specs/run/_021_mjs_modules/021_mjs_modules.ts.out
similarity index 100%
rename from tests/testdata/run/021_mjs_modules.ts.out
rename to tests/specs/run/_021_mjs_modules/021_mjs_modules.ts.out
diff --git a/tests/specs/run/_021_mjs_modules/__test__.jsonc b/tests/specs/run/_021_mjs_modules/__test__.jsonc
new file mode 100644
index 0000000000..f029658862
--- /dev/null
+++ b/tests/specs/run/_021_mjs_modules/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload 021_mjs_modules.ts",
+  "output": "021_mjs_modules.ts.out"
+}
diff --git a/tests/specs/run/_021_mjs_modules/mod5.mjs b/tests/specs/run/_021_mjs_modules/mod5.mjs
new file mode 100644
index 0000000000..f21d8862b1
--- /dev/null
+++ b/tests/specs/run/_021_mjs_modules/mod5.mjs
@@ -0,0 +1 @@
+export const isMod5 = true;
diff --git a/tests/testdata/run/025_reload_js_type_error.js b/tests/specs/run/_025_reload_js_type_error/025_reload_js_type_error.js
similarity index 100%
rename from tests/testdata/run/025_reload_js_type_error.js
rename to tests/specs/run/_025_reload_js_type_error/025_reload_js_type_error.js
diff --git a/tests/testdata/run/025_reload_js_type_error.js.out b/tests/specs/run/_025_reload_js_type_error/025_reload_js_type_error.js.out
similarity index 100%
rename from tests/testdata/run/025_reload_js_type_error.js.out
rename to tests/specs/run/_025_reload_js_type_error/025_reload_js_type_error.js.out
diff --git a/tests/specs/run/_025_reload_js_type_error/__test__.jsonc b/tests/specs/run/_025_reload_js_type_error/__test__.jsonc
new file mode 100644
index 0000000000..ce098f9097
--- /dev/null
+++ b/tests/specs/run/_025_reload_js_type_error/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload 025_reload_js_type_error.js",
+  "output": "025_reload_js_type_error.js.out"
+}
diff --git a/tests/testdata/run/027_redirect_typescript.ts b/tests/specs/run/_027_redirect_typescript/027_redirect_typescript.ts
similarity index 100%
rename from tests/testdata/run/027_redirect_typescript.ts
rename to tests/specs/run/_027_redirect_typescript/027_redirect_typescript.ts
diff --git a/tests/testdata/run/027_redirect_typescript.ts.out b/tests/specs/run/_027_redirect_typescript/027_redirect_typescript.ts.out
similarity index 100%
rename from tests/testdata/run/027_redirect_typescript.ts.out
rename to tests/specs/run/_027_redirect_typescript/027_redirect_typescript.ts.out
diff --git a/tests/specs/run/_027_redirect_typescript/__test__.jsonc b/tests/specs/run/_027_redirect_typescript/__test__.jsonc
new file mode 100644
index 0000000000..fca55c9f8e
--- /dev/null
+++ b/tests/specs/run/_027_redirect_typescript/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-import 027_redirect_typescript.ts",
+  "output": "027_redirect_typescript.ts.out"
+}
diff --git a/tests/specs/run/_027_redirect_typescript_vendor_dir/027_redirect_typescript.ts b/tests/specs/run/_027_redirect_typescript_vendor_dir/027_redirect_typescript.ts
new file mode 100644
index 0000000000..584341975f
--- /dev/null
+++ b/tests/specs/run/_027_redirect_typescript_vendor_dir/027_redirect_typescript.ts
@@ -0,0 +1,2 @@
+import { value } from "http://localhost:4547/redirects/redirect4.ts";
+console.log(value);
diff --git a/tests/specs/run/_027_redirect_typescript_vendor_dir/027_redirect_typescript.ts.out b/tests/specs/run/_027_redirect_typescript_vendor_dir/027_redirect_typescript.ts.out
new file mode 100644
index 0000000000..480d4e8ca0
--- /dev/null
+++ b/tests/specs/run/_027_redirect_typescript_vendor_dir/027_redirect_typescript.ts.out
@@ -0,0 +1 @@
+4 imports 1
diff --git a/tests/specs/run/_027_redirect_typescript_vendor_dir/__test__.jsonc b/tests/specs/run/_027_redirect_typescript_vendor_dir/__test__.jsonc
new file mode 100644
index 0000000000..f35557907b
--- /dev/null
+++ b/tests/specs/run/_027_redirect_typescript_vendor_dir/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --vendor --allow-import 027_redirect_typescript.ts",
+  "output": "027_redirect_typescript.ts.out"
+}
diff --git a/tests/specs/run/_027_redirect_typescript_vendor_dir/vendor/http_localhost_4545/subdir/redirects/redirect1.ts b/tests/specs/run/_027_redirect_typescript_vendor_dir/vendor/http_localhost_4545/subdir/redirects/redirect1.ts
new file mode 100644
index 0000000000..d674be88c3
--- /dev/null
+++ b/tests/specs/run/_027_redirect_typescript_vendor_dir/vendor/http_localhost_4545/subdir/redirects/redirect1.ts
@@ -0,0 +1 @@
+export const redirect = 1;
diff --git a/tests/specs/run/_027_redirect_typescript_vendor_dir/vendor/http_localhost_4545/subdir/redirects/redirect4.ts b/tests/specs/run/_027_redirect_typescript_vendor_dir/vendor/http_localhost_4545/subdir/redirects/redirect4.ts
new file mode 100644
index 0000000000..45c65c5eb3
--- /dev/null
+++ b/tests/specs/run/_027_redirect_typescript_vendor_dir/vendor/http_localhost_4545/subdir/redirects/redirect4.ts
@@ -0,0 +1,2 @@
+import { redirect } from "./redirect1.ts";
+export const value = `4 imports ${redirect}`;
diff --git a/tests/specs/run/_027_redirect_typescript_vendor_dir/vendor/manifest.json b/tests/specs/run/_027_redirect_typescript_vendor_dir/vendor/manifest.json
new file mode 100644
index 0000000000..49cc42e8cc
--- /dev/null
+++ b/tests/specs/run/_027_redirect_typescript_vendor_dir/vendor/manifest.json
@@ -0,0 +1,9 @@
+{
+  "modules": {
+    "http://localhost:4547/redirects/redirect4.ts": {
+      "headers": {
+        "location": "http://localhost:4545/subdir/redirects/redirect4.ts"
+      }
+    }
+  }
+}
diff --git a/tests/testdata/run/028_args.ts b/tests/specs/run/_028_args/028_args.ts
similarity index 100%
rename from tests/testdata/run/028_args.ts
rename to tests/specs/run/_028_args/028_args.ts
diff --git a/tests/testdata/run/028_args.ts.out b/tests/specs/run/_028_args/028_args.ts.out
similarity index 100%
rename from tests/testdata/run/028_args.ts.out
rename to tests/specs/run/_028_args/028_args.ts.out
diff --git a/tests/specs/run/_028_args/__test__.jsonc b/tests/specs/run/_028_args/__test__.jsonc
new file mode 100644
index 0000000000..6ab81bf21d
--- /dev/null
+++ b/tests/specs/run/_028_args/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload 028_args.ts --arg1 val1 --arg2=val2 -- arg3 arg4",
+  "output": "028_args.ts.out"
+}
diff --git a/tests/specs/run/_033_import_map_data_uri/__test__.jsonc b/tests/specs/run/_033_import_map_data_uri/__test__.jsonc
new file mode 100644
index 0000000000..400269c751
--- /dev/null
+++ b/tests/specs/run/_033_import_map_data_uri/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-import --import-map=data:application/json;charset=utf-8;base64,ewogICJpbXBvcnRzIjogewogICAgInRlc3Rfc2VydmVyLyI6ICJodHRwOi8vbG9jYWxob3N0OjQ1NDUvIgogIH0KfQ== test_data.ts",
+  "output": "test_data.ts.out"
+}
diff --git a/tests/specs/run/_033_import_map_data_uri/lodash/lodash.ts b/tests/specs/run/_033_import_map_data_uri/lodash/lodash.ts
new file mode 100644
index 0000000000..2ec04ed3cf
--- /dev/null
+++ b/tests/specs/run/_033_import_map_data_uri/lodash/lodash.ts
@@ -0,0 +1 @@
+console.log("Hello from remapped lodash!");
diff --git a/tests/specs/run/_033_import_map_data_uri/lodash/other_file.ts b/tests/specs/run/_033_import_map_data_uri/lodash/other_file.ts
new file mode 100644
index 0000000000..714adae3fb
--- /dev/null
+++ b/tests/specs/run/_033_import_map_data_uri/lodash/other_file.ts
@@ -0,0 +1 @@
+console.log("Hello from remapped lodash dir!");
diff --git a/tests/testdata/run/import_maps/test_data.ts b/tests/specs/run/_033_import_map_data_uri/test_data.ts
similarity index 100%
rename from tests/testdata/run/import_maps/test_data.ts
rename to tests/specs/run/_033_import_map_data_uri/test_data.ts
diff --git a/tests/testdata/run/import_maps/test_data.ts.out b/tests/specs/run/_033_import_map_data_uri/test_data.ts.out
similarity index 100%
rename from tests/testdata/run/import_maps/test_data.ts.out
rename to tests/specs/run/_033_import_map_data_uri/test_data.ts.out
diff --git a/tests/testdata/run/033_import_map_remote.out b/tests/specs/run/_033_import_map_remote/033_import_map_remote.out
similarity index 100%
rename from tests/testdata/run/033_import_map_remote.out
rename to tests/specs/run/_033_import_map_remote/033_import_map_remote.out
diff --git a/tests/specs/run/_033_import_map_remote/__test__.jsonc b/tests/specs/run/_033_import_map_remote/__test__.jsonc
new file mode 100644
index 0000000000..20c848d492
--- /dev/null
+++ b/tests/specs/run/_033_import_map_remote/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-import --import-map=import_map_remote.json test_remote.ts",
+  "output": "033_import_map_remote.out"
+}
diff --git a/tests/specs/run/_033_import_map_remote/import_map_remote.json b/tests/specs/run/_033_import_map_remote/import_map_remote.json
new file mode 100644
index 0000000000..190fc4f55a
--- /dev/null
+++ b/tests/specs/run/_033_import_map_remote/import_map_remote.json
@@ -0,0 +1,10 @@
+{
+  "imports": {
+    "moment": "./moment/moment.ts",
+    "moment/": "./moment/",
+    "lodash": "./lodash/lodash.ts",
+    "lodash/": "./lodash/",
+    "https://www.unpkg.com/vue/dist/vue.runtime.esm.js": "./vue.ts",
+    "print_hello": "./print_hello.ts"
+  }
+}
diff --git a/tests/specs/run/_033_import_map_remote/lodash/lodash.ts b/tests/specs/run/_033_import_map_remote/lodash/lodash.ts
new file mode 100644
index 0000000000..2ec04ed3cf
--- /dev/null
+++ b/tests/specs/run/_033_import_map_remote/lodash/lodash.ts
@@ -0,0 +1 @@
+console.log("Hello from remapped lodash!");
diff --git a/tests/specs/run/_033_import_map_remote/lodash/other_file.ts b/tests/specs/run/_033_import_map_remote/lodash/other_file.ts
new file mode 100644
index 0000000000..714adae3fb
--- /dev/null
+++ b/tests/specs/run/_033_import_map_remote/lodash/other_file.ts
@@ -0,0 +1 @@
+console.log("Hello from remapped lodash dir!");
diff --git a/tests/specs/run/_033_import_map_remote/moment/moment.ts b/tests/specs/run/_033_import_map_remote/moment/moment.ts
new file mode 100644
index 0000000000..2b54a431e7
--- /dev/null
+++ b/tests/specs/run/_033_import_map_remote/moment/moment.ts
@@ -0,0 +1 @@
+console.log("Hello from remapped moment!");
diff --git a/tests/specs/run/_033_import_map_remote/moment/other_file.ts b/tests/specs/run/_033_import_map_remote/moment/other_file.ts
new file mode 100644
index 0000000000..24f3a0226d
--- /dev/null
+++ b/tests/specs/run/_033_import_map_remote/moment/other_file.ts
@@ -0,0 +1 @@
+console.log("Hello from remapped moment dir!");
diff --git a/tests/specs/run/_033_import_map_remote/print_hello.ts b/tests/specs/run/_033_import_map_remote/print_hello.ts
new file mode 100644
index 0000000000..7942573905
--- /dev/null
+++ b/tests/specs/run/_033_import_map_remote/print_hello.ts
@@ -0,0 +1,3 @@
+export function printHello() {
+  console.log("Hello, world!");
+}
diff --git a/tests/specs/run/_033_import_map_remote/test_remote.ts b/tests/specs/run/_033_import_map_remote/test_remote.ts
new file mode 100644
index 0000000000..206bdbd5ff
--- /dev/null
+++ b/tests/specs/run/_033_import_map_remote/test_remote.ts
@@ -0,0 +1,5 @@
+import "moment";
+import "moment/other_file.ts";
+import "lodash";
+import "lodash/other_file.ts";
+import "https://www.unpkg.com/vue/dist/vue.runtime.esm.js";
diff --git a/tests/specs/run/_033_import_map_remote/vue.ts b/tests/specs/run/_033_import_map_remote/vue.ts
new file mode 100644
index 0000000000..76dbe19179
--- /dev/null
+++ b/tests/specs/run/_033_import_map_remote/vue.ts
@@ -0,0 +1 @@
+console.log("Hello from remapped Vue!");
diff --git a/tests/specs/run/_033_import_map_vendor_dir_remote/033_import_map_remote.out b/tests/specs/run/_033_import_map_vendor_dir_remote/033_import_map_remote.out
new file mode 100644
index 0000000000..804fa0d57e
--- /dev/null
+++ b/tests/specs/run/_033_import_map_vendor_dir_remote/033_import_map_remote.out
@@ -0,0 +1,5 @@
+Hello from remapped moment!
+Hello from remapped moment dir!
+Hello from remapped lodash!
+Hello from remapped lodash dir!
+Hello from remapped Vue!
diff --git a/tests/specs/run/_033_import_map_vendor_dir_remote/__test__.jsonc b/tests/specs/run/_033_import_map_vendor_dir_remote/__test__.jsonc
new file mode 100644
index 0000000000..4eb3a22c50
--- /dev/null
+++ b/tests/specs/run/_033_import_map_vendor_dir_remote/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-import --import-map=import_map_remote.json --vendor test_remote.ts",
+  "output": "033_import_map_remote.out"
+}
diff --git a/tests/specs/run/_033_import_map_vendor_dir_remote/import_map_remote.json b/tests/specs/run/_033_import_map_vendor_dir_remote/import_map_remote.json
new file mode 100644
index 0000000000..190fc4f55a
--- /dev/null
+++ b/tests/specs/run/_033_import_map_vendor_dir_remote/import_map_remote.json
@@ -0,0 +1,10 @@
+{
+  "imports": {
+    "moment": "./moment/moment.ts",
+    "moment/": "./moment/",
+    "lodash": "./lodash/lodash.ts",
+    "lodash/": "./lodash/",
+    "https://www.unpkg.com/vue/dist/vue.runtime.esm.js": "./vue.ts",
+    "print_hello": "./print_hello.ts"
+  }
+}
diff --git a/tests/specs/run/_033_import_map_vendor_dir_remote/lodash/lodash.ts b/tests/specs/run/_033_import_map_vendor_dir_remote/lodash/lodash.ts
new file mode 100644
index 0000000000..2ec04ed3cf
--- /dev/null
+++ b/tests/specs/run/_033_import_map_vendor_dir_remote/lodash/lodash.ts
@@ -0,0 +1 @@
+console.log("Hello from remapped lodash!");
diff --git a/tests/specs/run/_033_import_map_vendor_dir_remote/lodash/other_file.ts b/tests/specs/run/_033_import_map_vendor_dir_remote/lodash/other_file.ts
new file mode 100644
index 0000000000..714adae3fb
--- /dev/null
+++ b/tests/specs/run/_033_import_map_vendor_dir_remote/lodash/other_file.ts
@@ -0,0 +1 @@
+console.log("Hello from remapped lodash dir!");
diff --git a/tests/specs/run/_033_import_map_vendor_dir_remote/moment/moment.ts b/tests/specs/run/_033_import_map_vendor_dir_remote/moment/moment.ts
new file mode 100644
index 0000000000..2b54a431e7
--- /dev/null
+++ b/tests/specs/run/_033_import_map_vendor_dir_remote/moment/moment.ts
@@ -0,0 +1 @@
+console.log("Hello from remapped moment!");
diff --git a/tests/specs/run/_033_import_map_vendor_dir_remote/moment/other_file.ts b/tests/specs/run/_033_import_map_vendor_dir_remote/moment/other_file.ts
new file mode 100644
index 0000000000..24f3a0226d
--- /dev/null
+++ b/tests/specs/run/_033_import_map_vendor_dir_remote/moment/other_file.ts
@@ -0,0 +1 @@
+console.log("Hello from remapped moment dir!");
diff --git a/tests/specs/run/_033_import_map_vendor_dir_remote/print_hello.ts b/tests/specs/run/_033_import_map_vendor_dir_remote/print_hello.ts
new file mode 100644
index 0000000000..7942573905
--- /dev/null
+++ b/tests/specs/run/_033_import_map_vendor_dir_remote/print_hello.ts
@@ -0,0 +1,3 @@
+export function printHello() {
+  console.log("Hello, world!");
+}
diff --git a/tests/specs/run/_033_import_map_vendor_dir_remote/test_remote.ts b/tests/specs/run/_033_import_map_vendor_dir_remote/test_remote.ts
new file mode 100644
index 0000000000..206bdbd5ff
--- /dev/null
+++ b/tests/specs/run/_033_import_map_vendor_dir_remote/test_remote.ts
@@ -0,0 +1,5 @@
+import "moment";
+import "moment/other_file.ts";
+import "lodash";
+import "lodash/other_file.ts";
+import "https://www.unpkg.com/vue/dist/vue.runtime.esm.js";
diff --git a/tests/specs/run/_033_import_map_vendor_dir_remote/vue.ts b/tests/specs/run/_033_import_map_vendor_dir_remote/vue.ts
new file mode 100644
index 0000000000..76dbe19179
--- /dev/null
+++ b/tests/specs/run/_033_import_map_vendor_dir_remote/vue.ts
@@ -0,0 +1 @@
+console.log("Hello from remapped Vue!");
diff --git a/tests/specs/run/_035_cached_only_flag/019_media_types.ts b/tests/specs/run/_035_cached_only_flag/019_media_types.ts
new file mode 100644
index 0000000000..d985bd2496
--- /dev/null
+++ b/tests/specs/run/_035_cached_only_flag/019_media_types.ts
@@ -0,0 +1,24 @@
+// When run against the test HTTP server, it will serve different media types
+// based on the URL containing `.t#.` strings, which exercises the different
+// mapping of media types end to end.
+
+import { loaded as loadedTs1 } from "http://localhost:4545/subdir/mt_text_typescript.t1.ts";
+import { loaded as loadedTs2 } from "http://localhost:4545/subdir/mt_video_vdn.t2.ts";
+import { loaded as loadedTs3 } from "http://localhost:4545/subdir/mt_video_mp2t.t3.ts";
+import { loaded as loadedTs4 } from "http://localhost:4545/subdir/mt_application_x_typescript.t4.ts";
+import { loaded as loadedJs1 } from "http://localhost:4545/subdir/mt_text_javascript.j1.js";
+import { loaded as loadedJs2 } from "http://localhost:4545/subdir/mt_application_ecmascript.j2.js";
+import { loaded as loadedJs3 } from "http://localhost:4545/subdir/mt_text_ecmascript.j3.js";
+import { loaded as loadedJs4 } from "http://localhost:4545/subdir/mt_application_x_javascript.j4.js";
+
+console.log(
+  "success",
+  loadedTs1,
+  loadedTs2,
+  loadedTs3,
+  loadedTs4,
+  loadedJs1,
+  loadedJs2,
+  loadedJs3,
+  loadedJs4,
+);
diff --git a/tests/specs/run/_035_cached_only_flag/035_cached_only_flag.out b/tests/specs/run/_035_cached_only_flag/035_cached_only_flag.out
new file mode 100644
index 0000000000..aad3f2fbc1
--- /dev/null
+++ b/tests/specs/run/_035_cached_only_flag/035_cached_only_flag.out
@@ -0,0 +1 @@
+error: Specifier not found in cache: "http://127.0.0.1:4545/019_media_types.ts", --cached-only is specified.
diff --git a/tests/specs/run/_035_cached_only_flag/__test__.jsonc b/tests/specs/run/_035_cached_only_flag/__test__.jsonc
new file mode 100644
index 0000000000..ac9d01cdd0
--- /dev/null
+++ b/tests/specs/run/_035_cached_only_flag/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload --check --allow-import --cached-only http://127.0.0.1:4545/019_media_types.ts",
+  "output": "035_cached_only_flag.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/038_checkjs.js b/tests/specs/run/_038_checkjs/038_checkjs.js
similarity index 100%
rename from tests/testdata/run/038_checkjs.js
rename to tests/specs/run/_038_checkjs/038_checkjs.js
diff --git a/tests/testdata/run/038_checkjs.js.out b/tests/specs/run/_038_checkjs/038_checkjs.js.out
similarity index 100%
rename from tests/testdata/run/038_checkjs.js.out
rename to tests/specs/run/_038_checkjs/038_checkjs.js.out
diff --git a/tests/specs/run/_038_checkjs/__test__.jsonc b/tests/specs/run/_038_checkjs/__test__.jsonc
new file mode 100644
index 0000000000..6915787d2d
--- /dev/null
+++ b/tests/specs/run/_038_checkjs/__test__.jsonc
@@ -0,0 +1,6 @@
+{
+  // checking if JS file is run through TS compiler
+  "args": "run --reload --config checkjs.tsconfig.json --check 038_checkjs.js",
+  "exitCode": 1,
+  "output": "038_checkjs.js.out"
+}
diff --git a/tests/specs/run/_038_checkjs/checkjs.tsconfig.json b/tests/specs/run/_038_checkjs/checkjs.tsconfig.json
new file mode 100644
index 0000000000..08ac60b6cd
--- /dev/null
+++ b/tests/specs/run/_038_checkjs/checkjs.tsconfig.json
@@ -0,0 +1,5 @@
+{
+  "compilerOptions": {
+    "checkJs": true
+  }
+}
diff --git a/tests/testdata/run/042_dyn_import_evalcontext.ts b/tests/specs/run/_042_dyn_import_evalcontext/042_dyn_import_evalcontext.ts
similarity index 63%
rename from tests/testdata/run/042_dyn_import_evalcontext.ts
rename to tests/specs/run/_042_dyn_import_evalcontext/042_dyn_import_evalcontext.ts
index 386ae48ec7..f39ae24685 100644
--- a/tests/testdata/run/042_dyn_import_evalcontext.ts
+++ b/tests/specs/run/_042_dyn_import_evalcontext/042_dyn_import_evalcontext.ts
@@ -1,5 +1,5 @@
 // @ts-expect-error "Deno[Deno.internal].core" is not a public interface
 Deno[Deno.internal].core.evalContext(
-  "(async () => console.log(await import('./subdir/mod4.js')))()",
+  "(async () => console.log(await import('./_042_dyn_import_evalcontext/mod4.js')))()",
   new URL("..", import.meta.url).href,
 );
diff --git a/tests/testdata/run/042_dyn_import_evalcontext.ts.out b/tests/specs/run/_042_dyn_import_evalcontext/042_dyn_import_evalcontext.ts.out
similarity index 100%
rename from tests/testdata/run/042_dyn_import_evalcontext.ts.out
rename to tests/specs/run/_042_dyn_import_evalcontext/042_dyn_import_evalcontext.ts.out
diff --git a/tests/specs/run/_042_dyn_import_evalcontext/__test__.jsonc b/tests/specs/run/_042_dyn_import_evalcontext/__test__.jsonc
new file mode 100644
index 0000000000..e3cb0d1844
--- /dev/null
+++ b/tests/specs/run/_042_dyn_import_evalcontext/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --allow-read --reload 042_dyn_import_evalcontext.ts",
+  "output": "042_dyn_import_evalcontext.ts.out"
+}
diff --git a/tests/specs/run/_042_dyn_import_evalcontext/mod4.js b/tests/specs/run/_042_dyn_import_evalcontext/mod4.js
new file mode 100644
index 0000000000..71332dbc42
--- /dev/null
+++ b/tests/specs/run/_042_dyn_import_evalcontext/mod4.js
@@ -0,0 +1 @@
+export const isMod4 = true;
diff --git a/tests/specs/run/_044_bad_resource/044_bad_resource.ts b/tests/specs/run/_044_bad_resource/044_bad_resource.ts
new file mode 100644
index 0000000000..c76a11eff9
--- /dev/null
+++ b/tests/specs/run/_044_bad_resource/044_bad_resource.ts
@@ -0,0 +1,3 @@
+const file = await Deno.open("./044_bad_resource.ts", { read: true });
+file.close();
+await file.seek(10, 0);
diff --git a/tests/testdata/run/044_bad_resource.ts.out b/tests/specs/run/_044_bad_resource/044_bad_resource.ts.out
similarity index 100%
rename from tests/testdata/run/044_bad_resource.ts.out
rename to tests/specs/run/_044_bad_resource/044_bad_resource.ts.out
diff --git a/tests/specs/run/_044_bad_resource/__test__.jsonc b/tests/specs/run/_044_bad_resource/__test__.jsonc
new file mode 100644
index 0000000000..cb7832e74a
--- /dev/null
+++ b/tests/specs/run/_044_bad_resource/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --reload --allow-read 044_bad_resource.ts",
+  "output": "044_bad_resource.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/046_jsx_test.tsx b/tests/specs/run/_046_tsx/046_jsx_test.tsx
similarity index 100%
rename from tests/testdata/run/046_jsx_test.tsx
rename to tests/specs/run/_046_tsx/046_jsx_test.tsx
diff --git a/tests/testdata/run/046_jsx_test.tsx.out b/tests/specs/run/_046_tsx/046_jsx_test.tsx.out
similarity index 100%
rename from tests/testdata/run/046_jsx_test.tsx.out
rename to tests/specs/run/_046_tsx/046_jsx_test.tsx.out
diff --git a/tests/specs/run/_046_tsx/__test__.jsonc b/tests/specs/run/_046_tsx/__test__.jsonc
new file mode 100644
index 0000000000..28a48ececc
--- /dev/null
+++ b/tests/specs/run/_046_tsx/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload 046_jsx_test.tsx",
+  "output": "046_jsx_test.tsx.out"
+}
diff --git a/tests/testdata/run/047_jsx_test.jsx b/tests/specs/run/_047_jsx/047_jsx_test.jsx
similarity index 100%
rename from tests/testdata/run/047_jsx_test.jsx
rename to tests/specs/run/_047_jsx/047_jsx_test.jsx
diff --git a/tests/testdata/run/047_jsx_test.jsx.out b/tests/specs/run/_047_jsx/047_jsx_test.jsx.out
similarity index 100%
rename from tests/testdata/run/047_jsx_test.jsx.out
rename to tests/specs/run/_047_jsx/047_jsx_test.jsx.out
diff --git a/tests/specs/run/_047_jsx/__test__.jsonc b/tests/specs/run/_047_jsx/__test__.jsonc
new file mode 100644
index 0000000000..bb89db0177
--- /dev/null
+++ b/tests/specs/run/_047_jsx/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload 047_jsx_test.jsx",
+  "output": "047_jsx_test.jsx.out"
+}
diff --git a/tests/specs/run/_048_media_types_jsx/048_media_types_jsx.ts b/tests/specs/run/_048_media_types_jsx/048_media_types_jsx.ts
new file mode 100644
index 0000000000..8dcd0ad687
--- /dev/null
+++ b/tests/specs/run/_048_media_types_jsx/048_media_types_jsx.ts
@@ -0,0 +1,32 @@
+// When run against the test HTTP server, it will serve different media types
+// based on the URL containing `.t#.` strings, which exercises the different
+// mapping of media types end to end.
+import { loaded as loadedTsx1 } from "http://localhost:4545/subdir/mt_text_typescript_tsx.t1.tsx";
+import { loaded as loadedTsx2 } from "http://localhost:4545/subdir/mt_video_vdn_tsx.t2.tsx";
+import { loaded as loadedTsx3 } from "http://localhost:4545/subdir/mt_video_mp2t_tsx.t3.tsx";
+import { loaded as loadedTsx4 } from "http://localhost:4545/subdir/mt_application_x_typescript_tsx.t4.tsx";
+import { loaded as loadedJsx1 } from "http://localhost:4545/subdir/mt_text_javascript_jsx.j1.jsx";
+import { loaded as loadedJsx2 } from "http://localhost:4545/subdir/mt_application_ecmascript_jsx.j2.jsx";
+import { loaded as loadedJsx3 } from "http://localhost:4545/subdir/mt_text_ecmascript_jsx.j3.jsx";
+import { loaded as loadedJsx4 } from "http://localhost:4545/subdir/mt_application_x_javascript_jsx.j4.jsx";
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      // deno-lint-ignore no-explicit-any
+      [elemName: string]: any;
+    }
+  }
+}
+
+console.log(
+  "success",
+  loadedTsx1,
+  loadedTsx2,
+  loadedTsx3,
+  loadedTsx4,
+  loadedJsx1,
+  loadedJsx2,
+  loadedJsx3,
+  loadedJsx4,
+);
diff --git a/tests/testdata/run/048_media_types_jsx.ts.out b/tests/specs/run/_048_media_types_jsx/048_media_types_jsx.ts.out
similarity index 100%
rename from tests/testdata/run/048_media_types_jsx.ts.out
rename to tests/specs/run/_048_media_types_jsx/048_media_types_jsx.ts.out
diff --git a/tests/specs/run/_048_media_types_jsx/__test__.jsonc b/tests/specs/run/_048_media_types_jsx/__test__.jsonc
new file mode 100644
index 0000000000..0dec930b09
--- /dev/null
+++ b/tests/specs/run/_048_media_types_jsx/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run  --reload --allow-import 048_media_types_jsx.ts",
+  "output": "048_media_types_jsx.ts.out"
+}
diff --git a/tests/specs/run/_052_no_remote_flag/019_media_types.ts b/tests/specs/run/_052_no_remote_flag/019_media_types.ts
new file mode 100644
index 0000000000..d985bd2496
--- /dev/null
+++ b/tests/specs/run/_052_no_remote_flag/019_media_types.ts
@@ -0,0 +1,24 @@
+// When run against the test HTTP server, it will serve different media types
+// based on the URL containing `.t#.` strings, which exercises the different
+// mapping of media types end to end.
+
+import { loaded as loadedTs1 } from "http://localhost:4545/subdir/mt_text_typescript.t1.ts";
+import { loaded as loadedTs2 } from "http://localhost:4545/subdir/mt_video_vdn.t2.ts";
+import { loaded as loadedTs3 } from "http://localhost:4545/subdir/mt_video_mp2t.t3.ts";
+import { loaded as loadedTs4 } from "http://localhost:4545/subdir/mt_application_x_typescript.t4.ts";
+import { loaded as loadedJs1 } from "http://localhost:4545/subdir/mt_text_javascript.j1.js";
+import { loaded as loadedJs2 } from "http://localhost:4545/subdir/mt_application_ecmascript.j2.js";
+import { loaded as loadedJs3 } from "http://localhost:4545/subdir/mt_text_ecmascript.j3.js";
+import { loaded as loadedJs4 } from "http://localhost:4545/subdir/mt_application_x_javascript.j4.js";
+
+console.log(
+  "success",
+  loadedTs1,
+  loadedTs2,
+  loadedTs3,
+  loadedTs4,
+  loadedJs1,
+  loadedJs2,
+  loadedJs3,
+  loadedJs4,
+);
diff --git a/tests/testdata/run/052_no_remote_flag.out b/tests/specs/run/_052_no_remote_flag/052_no_remote_flag.out
similarity index 53%
rename from tests/testdata/run/052_no_remote_flag.out
rename to tests/specs/run/_052_no_remote_flag/052_no_remote_flag.out
index 2f5950ee89..c1f9f4e131 100644
--- a/tests/testdata/run/052_no_remote_flag.out
+++ b/tests/specs/run/_052_no_remote_flag/052_no_remote_flag.out
@@ -1 +1 @@
-error: A remote specifier was requested: "http://127.0.0.1:4545/run/019_media_types.ts", but --no-remote is specified.
+error: A remote specifier was requested: "http://127.0.0.1:4545/019_media_types.ts", but --no-remote is specified.
diff --git a/tests/specs/run/_052_no_remote_flag/__test__.jsonc b/tests/specs/run/_052_no_remote_flag/__test__.jsonc
new file mode 100644
index 0000000000..c8ac477c66
--- /dev/null
+++ b/tests/specs/run/_052_no_remote_flag/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload --check --allow-import --no-remote http://127.0.0.1:4545/019_media_types.ts",
+  "output": "052_no_remote_flag.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/058_tasks_microtasks_close.ts b/tests/specs/run/_058_tasks_microtasks_close/058_tasks_microtasks_close.ts
similarity index 100%
rename from tests/testdata/run/058_tasks_microtasks_close.ts
rename to tests/specs/run/_058_tasks_microtasks_close/058_tasks_microtasks_close.ts
diff --git a/tests/testdata/run/058_tasks_microtasks_close.ts.out b/tests/specs/run/_058_tasks_microtasks_close/058_tasks_microtasks_close.ts.out
similarity index 100%
rename from tests/testdata/run/058_tasks_microtasks_close.ts.out
rename to tests/specs/run/_058_tasks_microtasks_close/058_tasks_microtasks_close.ts.out
diff --git a/tests/specs/run/_058_tasks_microtasks_close/__test__.jsonc b/tests/specs/run/_058_tasks_microtasks_close/__test__.jsonc
new file mode 100644
index 0000000000..9eec8f53cb
--- /dev/null
+++ b/tests/specs/run/_058_tasks_microtasks_close/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet 058_tasks_microtasks_close.ts",
+  "output": "058_tasks_microtasks_close.ts.out"
+}
diff --git a/tests/testdata/run/059_fs_relative_path_perm.ts b/tests/specs/run/_059_fs_relative_path_perm/059_fs_relative_path_perm.ts
similarity index 100%
rename from tests/testdata/run/059_fs_relative_path_perm.ts
rename to tests/specs/run/_059_fs_relative_path_perm/059_fs_relative_path_perm.ts
diff --git a/tests/testdata/run/059_fs_relative_path_perm.ts.out b/tests/specs/run/_059_fs_relative_path_perm/059_fs_relative_path_perm.ts.out
similarity index 100%
rename from tests/testdata/run/059_fs_relative_path_perm.ts.out
rename to tests/specs/run/_059_fs_relative_path_perm/059_fs_relative_path_perm.ts.out
diff --git a/tests/specs/run/_059_fs_relative_path_perm/__test__.jsonc b/tests/specs/run/_059_fs_relative_path_perm/__test__.jsonc
new file mode 100644
index 0000000000..04a7b8aa4f
--- /dev/null
+++ b/tests/specs/run/_059_fs_relative_path_perm/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run 059_fs_relative_path_perm.ts",
+  "output": "059_fs_relative_path_perm.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/063_permissions_revoke.ts b/tests/specs/run/_063_permissions_revoke/063_permissions_revoke.ts
similarity index 100%
rename from tests/testdata/run/063_permissions_revoke.ts
rename to tests/specs/run/_063_permissions_revoke/063_permissions_revoke.ts
diff --git a/tests/testdata/run/063_permissions_revoke.ts.out b/tests/specs/run/_063_permissions_revoke/063_permissions_revoke.ts.out
similarity index 100%
rename from tests/testdata/run/063_permissions_revoke.ts.out
rename to tests/specs/run/_063_permissions_revoke/063_permissions_revoke.ts.out
diff --git a/tests/specs/run/_063_permissions_revoke/__test__.jsonc b/tests/specs/run/_063_permissions_revoke/__test__.jsonc
new file mode 100644
index 0000000000..1dd5ed747f
--- /dev/null
+++ b/tests/specs/run/_063_permissions_revoke/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read=foo,bar 063_permissions_revoke.ts",
+  "output": "063_permissions_revoke.ts.out"
+}
diff --git a/tests/specs/run/_063_permissions_revoke_sync/063_permissions_revoke.ts.out b/tests/specs/run/_063_permissions_revoke_sync/063_permissions_revoke.ts.out
new file mode 100644
index 0000000000..bbd64c557b
--- /dev/null
+++ b/tests/specs/run/_063_permissions_revoke_sync/063_permissions_revoke.ts.out
@@ -0,0 +1,3 @@
+[WILDCARD]PermissionStatus { state: "prompt", onchange: null }
+PermissionStatus { state: "granted", onchange: null }
+PermissionStatus { state: "prompt", onchange: null }
diff --git a/tests/testdata/run/063_permissions_revoke_sync.ts b/tests/specs/run/_063_permissions_revoke_sync/063_permissions_revoke_sync.ts
similarity index 100%
rename from tests/testdata/run/063_permissions_revoke_sync.ts
rename to tests/specs/run/_063_permissions_revoke_sync/063_permissions_revoke_sync.ts
diff --git a/tests/specs/run/_063_permissions_revoke_sync/__test__.jsonc b/tests/specs/run/_063_permissions_revoke_sync/__test__.jsonc
new file mode 100644
index 0000000000..8dd9384e3d
--- /dev/null
+++ b/tests/specs/run/_063_permissions_revoke_sync/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read=foo,bar 063_permissions_revoke_sync.ts",
+  "output": "063_permissions_revoke.ts.out"
+}
diff --git a/tests/testdata/run/064_permissions_revoke_global.ts b/tests/specs/run/_064_permissions_revoke_global/064_permissions_revoke_global.ts
similarity index 100%
rename from tests/testdata/run/064_permissions_revoke_global.ts
rename to tests/specs/run/_064_permissions_revoke_global/064_permissions_revoke_global.ts
diff --git a/tests/testdata/run/064_permissions_revoke_global.ts.out b/tests/specs/run/_064_permissions_revoke_global/064_permissions_revoke_global.ts.out
similarity index 100%
rename from tests/testdata/run/064_permissions_revoke_global.ts.out
rename to tests/specs/run/_064_permissions_revoke_global/064_permissions_revoke_global.ts.out
diff --git a/tests/specs/run/_064_permissions_revoke_global/__test__.jsonc b/tests/specs/run/_064_permissions_revoke_global/__test__.jsonc
new file mode 100644
index 0000000000..929e48ee8d
--- /dev/null
+++ b/tests/specs/run/_064_permissions_revoke_global/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read=foo,bar 064_permissions_revoke_global.ts",
+  "output": "064_permissions_revoke_global.ts.out"
+}
diff --git a/tests/specs/run/_064_permissions_revoke_global_sync/064_permissions_revoke_global.ts.out b/tests/specs/run/_064_permissions_revoke_global_sync/064_permissions_revoke_global.ts.out
new file mode 100644
index 0000000000..f7e389a76b
--- /dev/null
+++ b/tests/specs/run/_064_permissions_revoke_global_sync/064_permissions_revoke_global.ts.out
@@ -0,0 +1,3 @@
+[WILDCARD]PermissionStatus { state: "prompt", onchange: null }
+PermissionStatus { state: "prompt", onchange: null }
+PermissionStatus { state: "prompt", onchange: null }
diff --git a/tests/testdata/run/064_permissions_revoke_global_sync.ts b/tests/specs/run/_064_permissions_revoke_global_sync/064_permissions_revoke_global_sync.ts
similarity index 100%
rename from tests/testdata/run/064_permissions_revoke_global_sync.ts
rename to tests/specs/run/_064_permissions_revoke_global_sync/064_permissions_revoke_global_sync.ts
diff --git a/tests/specs/run/_064_permissions_revoke_global_sync/__test__.jsonc b/tests/specs/run/_064_permissions_revoke_global_sync/__test__.jsonc
new file mode 100644
index 0000000000..8d6f8079d3
--- /dev/null
+++ b/tests/specs/run/_064_permissions_revoke_global_sync/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read=foo,bar 064_permissions_revoke_global_sync.ts",
+  "output": "064_permissions_revoke_global.ts.out"
+}
diff --git a/tests/testdata/run/065_permissions_revoke_net.ts b/tests/specs/run/_065_permissions_revoke_net/065_permissions_revoke_net.ts
similarity index 100%
rename from tests/testdata/run/065_permissions_revoke_net.ts
rename to tests/specs/run/_065_permissions_revoke_net/065_permissions_revoke_net.ts
diff --git a/tests/testdata/run/065_permissions_revoke_net.ts.out b/tests/specs/run/_065_permissions_revoke_net/065_permissions_revoke_net.ts.out
similarity index 100%
rename from tests/testdata/run/065_permissions_revoke_net.ts.out
rename to tests/specs/run/_065_permissions_revoke_net/065_permissions_revoke_net.ts.out
diff --git a/tests/specs/run/_065_permissions_revoke_net/__test__.jsonc b/tests/specs/run/_065_permissions_revoke_net/__test__.jsonc
new file mode 100644
index 0000000000..ab66835fdb
--- /dev/null
+++ b/tests/specs/run/_065_permissions_revoke_net/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-net 065_permissions_revoke_net.ts",
+  "output": "065_permissions_revoke_net.ts.out"
+}
diff --git a/tests/testdata/run/070_location.ts b/tests/specs/run/_070_location/070_location.ts
similarity index 100%
rename from tests/testdata/run/070_location.ts
rename to tests/specs/run/_070_location/070_location.ts
diff --git a/tests/testdata/run/070_location.ts.out b/tests/specs/run/_070_location/070_location.ts.out
similarity index 100%
rename from tests/testdata/run/070_location.ts.out
rename to tests/specs/run/_070_location/070_location.ts.out
diff --git a/tests/specs/run/_070_location/__test__.jsonc b/tests/specs/run/_070_location/__test__.jsonc
new file mode 100644
index 0000000000..ad92752ea0
--- /dev/null
+++ b/tests/specs/run/_070_location/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --location https://foo/bar?baz#bat 070_location.ts",
+  "output": "070_location.ts.out"
+}
diff --git a/tests/testdata/run/071_location_unset.ts b/tests/specs/run/_071_location_unset/071_location_unset.ts
similarity index 100%
rename from tests/testdata/run/071_location_unset.ts
rename to tests/specs/run/_071_location_unset/071_location_unset.ts
diff --git a/tests/testdata/run/071_location_unset.ts.out b/tests/specs/run/_071_location_unset/071_location_unset.ts.out
similarity index 100%
rename from tests/testdata/run/071_location_unset.ts.out
rename to tests/specs/run/_071_location_unset/071_location_unset.ts.out
diff --git a/tests/specs/run/_071_location_unset/__test__.jsonc b/tests/specs/run/_071_location_unset/__test__.jsonc
new file mode 100644
index 0000000000..946755cf5a
--- /dev/null
+++ b/tests/specs/run/_071_location_unset/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run 071_location_unset.ts",
+  "output": "071_location_unset.ts.out"
+}
diff --git a/tests/testdata/run/072_location_relative_fetch.ts b/tests/specs/run/_072_location_relative_fetch/072_location_relative_fetch.ts
similarity index 100%
rename from tests/testdata/run/072_location_relative_fetch.ts
rename to tests/specs/run/_072_location_relative_fetch/072_location_relative_fetch.ts
diff --git a/tests/testdata/run/072_location_relative_fetch.ts.out b/tests/specs/run/_072_location_relative_fetch/072_location_relative_fetch.ts.out
similarity index 100%
rename from tests/testdata/run/072_location_relative_fetch.ts.out
rename to tests/specs/run/_072_location_relative_fetch/072_location_relative_fetch.ts.out
diff --git a/tests/specs/run/_072_location_relative_fetch/__test__.jsonc b/tests/specs/run/_072_location_relative_fetch/__test__.jsonc
new file mode 100644
index 0000000000..e6e9e48996
--- /dev/null
+++ b/tests/specs/run/_072_location_relative_fetch/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --location http://127.0.0.1:4545/ --allow-net 072_location_relative_fetch.ts",
+  "output": "072_location_relative_fetch.ts.out"
+}
diff --git a/tests/specs/run/_072_location_relative_fetch/fetch/hello.txt b/tests/specs/run/_072_location_relative_fetch/fetch/hello.txt
new file mode 100644
index 0000000000..af5626b4a1
--- /dev/null
+++ b/tests/specs/run/_072_location_relative_fetch/fetch/hello.txt
@@ -0,0 +1 @@
+Hello, world!
diff --git a/tests/specs/run/_075_import_local_query_hash/001_hello.js b/tests/specs/run/_075_import_local_query_hash/001_hello.js
new file mode 100644
index 0000000000..accefceba6
--- /dev/null
+++ b/tests/specs/run/_075_import_local_query_hash/001_hello.js
@@ -0,0 +1 @@
+console.log("Hello World");
diff --git a/tests/specs/run/_075_import_local_query_hash/002_hello.ts b/tests/specs/run/_075_import_local_query_hash/002_hello.ts
new file mode 100644
index 0000000000..accefceba6
--- /dev/null
+++ b/tests/specs/run/_075_import_local_query_hash/002_hello.ts
@@ -0,0 +1 @@
+console.log("Hello World");
diff --git a/tests/testdata/run/075_import_local_query_hash.ts b/tests/specs/run/_075_import_local_query_hash/075_import_local_query_hash.ts
similarity index 100%
rename from tests/testdata/run/075_import_local_query_hash.ts
rename to tests/specs/run/_075_import_local_query_hash/075_import_local_query_hash.ts
diff --git a/tests/testdata/run/075_import_local_query_hash.ts.out b/tests/specs/run/_075_import_local_query_hash/075_import_local_query_hash.ts.out
similarity index 100%
rename from tests/testdata/run/075_import_local_query_hash.ts.out
rename to tests/specs/run/_075_import_local_query_hash/075_import_local_query_hash.ts.out
diff --git a/tests/specs/run/_075_import_local_query_hash/__test__.jsonc b/tests/specs/run/_075_import_local_query_hash/__test__.jsonc
new file mode 100644
index 0000000000..521cd3ea8a
--- /dev/null
+++ b/tests/specs/run/_075_import_local_query_hash/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run 075_import_local_query_hash.ts",
+  "output": "075_import_local_query_hash.ts.out"
+}
diff --git a/tests/testdata/run/077_fetch_empty.ts b/tests/specs/run/_077_fetch_empty/077_fetch_empty.ts
similarity index 100%
rename from tests/testdata/run/077_fetch_empty.ts
rename to tests/specs/run/_077_fetch_empty/077_fetch_empty.ts
diff --git a/tests/testdata/run/077_fetch_empty.ts.out b/tests/specs/run/_077_fetch_empty/077_fetch_empty.ts.out
similarity index 100%
rename from tests/testdata/run/077_fetch_empty.ts.out
rename to tests/specs/run/_077_fetch_empty/077_fetch_empty.ts.out
diff --git a/tests/specs/run/_077_fetch_empty/__test__.jsonc b/tests/specs/run/_077_fetch_empty/__test__.jsonc
new file mode 100644
index 0000000000..654b109380
--- /dev/null
+++ b/tests/specs/run/_077_fetch_empty/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run -A 077_fetch_empty.ts",
+  "output": "077_fetch_empty.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/078_unload_on_exit.ts b/tests/specs/run/_078_unload_on_exit/078_unload_on_exit.ts
similarity index 100%
rename from tests/testdata/run/078_unload_on_exit.ts
rename to tests/specs/run/_078_unload_on_exit/078_unload_on_exit.ts
diff --git a/tests/testdata/run/078_unload_on_exit.ts.out b/tests/specs/run/_078_unload_on_exit/078_unload_on_exit.ts.out
similarity index 100%
rename from tests/testdata/run/078_unload_on_exit.ts.out
rename to tests/specs/run/_078_unload_on_exit/078_unload_on_exit.ts.out
diff --git a/tests/specs/run/_078_unload_on_exit/__test__.jsonc b/tests/specs/run/_078_unload_on_exit/__test__.jsonc
new file mode 100644
index 0000000000..4091b7dc99
--- /dev/null
+++ b/tests/specs/run/_078_unload_on_exit/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run 078_unload_on_exit.ts",
+  "output": "078_unload_on_exit.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/079_location_authentication.ts b/tests/specs/run/_079_location_authentication/079_location_authentication.ts
similarity index 100%
rename from tests/testdata/run/079_location_authentication.ts
rename to tests/specs/run/_079_location_authentication/079_location_authentication.ts
diff --git a/tests/testdata/run/079_location_authentication.ts.out b/tests/specs/run/_079_location_authentication/079_location_authentication.ts.out
similarity index 100%
rename from tests/testdata/run/079_location_authentication.ts.out
rename to tests/specs/run/_079_location_authentication/079_location_authentication.ts.out
diff --git a/tests/specs/run/_079_location_authentication/__test__.jsonc b/tests/specs/run/_079_location_authentication/__test__.jsonc
new file mode 100644
index 0000000000..30ba279490
--- /dev/null
+++ b/tests/specs/run/_079_location_authentication/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --location https://foo:bar@baz/qux 079_location_authentication.ts",
+  "output": "079_location_authentication.ts.out"
+}
diff --git a/tests/testdata/run/081_location_relative_fetch_redirect.ts b/tests/specs/run/_081_location_relative_fetch_redirect/081_location_relative_fetch_redirect.ts
similarity index 100%
rename from tests/testdata/run/081_location_relative_fetch_redirect.ts
rename to tests/specs/run/_081_location_relative_fetch_redirect/081_location_relative_fetch_redirect.ts
diff --git a/tests/testdata/run/081_location_relative_fetch_redirect.ts.out b/tests/specs/run/_081_location_relative_fetch_redirect/081_location_relative_fetch_redirect.ts.out
similarity index 100%
rename from tests/testdata/run/081_location_relative_fetch_redirect.ts.out
rename to tests/specs/run/_081_location_relative_fetch_redirect/081_location_relative_fetch_redirect.ts.out
diff --git a/tests/specs/run/_081_location_relative_fetch_redirect/__test__.jsonc b/tests/specs/run/_081_location_relative_fetch_redirect/__test__.jsonc
new file mode 100644
index 0000000000..6756bf6d1f
--- /dev/null
+++ b/tests/specs/run/_081_location_relative_fetch_redirect/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --location http://127.0.0.1:4546/ --allow-net 081_location_relative_fetch_redirect.ts",
+  "output": "081_location_relative_fetch_redirect.ts.out"
+}
diff --git a/tests/testdata/run/082_prepare_stack_trace_throw.js b/tests/specs/run/_082_prepare_stack_trace_throw/082_prepare_stack_trace_throw.js
similarity index 100%
rename from tests/testdata/run/082_prepare_stack_trace_throw.js
rename to tests/specs/run/_082_prepare_stack_trace_throw/082_prepare_stack_trace_throw.js
diff --git a/tests/testdata/run/082_prepare_stack_trace_throw.js.out b/tests/specs/run/_082_prepare_stack_trace_throw/082_prepare_stack_trace_throw.js.out
similarity index 100%
rename from tests/testdata/run/082_prepare_stack_trace_throw.js.out
rename to tests/specs/run/_082_prepare_stack_trace_throw/082_prepare_stack_trace_throw.js.out
diff --git a/tests/specs/run/_082_prepare_stack_trace_throw/__test__.jsonc b/tests/specs/run/_082_prepare_stack_trace_throw/__test__.jsonc
new file mode 100644
index 0000000000..41b27e3bdd
--- /dev/null
+++ b/tests/specs/run/_082_prepare_stack_trace_throw/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run 082_prepare_stack_trace_throw.js",
+  "output": "082_prepare_stack_trace_throw.js.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/088_dynamic_import_already_evaluating.ts b/tests/specs/run/_088_dynamic_import_already_evaluating/088_dynamic_import_already_evaluating.ts
similarity index 100%
rename from tests/testdata/run/088_dynamic_import_already_evaluating.ts
rename to tests/specs/run/_088_dynamic_import_already_evaluating/088_dynamic_import_already_evaluating.ts
diff --git a/tests/testdata/run/088_dynamic_import_already_evaluating.ts.out b/tests/specs/run/_088_dynamic_import_already_evaluating/088_dynamic_import_already_evaluating.ts.out
similarity index 100%
rename from tests/testdata/run/088_dynamic_import_already_evaluating.ts.out
rename to tests/specs/run/_088_dynamic_import_already_evaluating/088_dynamic_import_already_evaluating.ts.out
diff --git a/tests/specs/run/_088_dynamic_import_already_evaluating/088_dynamic_import_target.ts b/tests/specs/run/_088_dynamic_import_already_evaluating/088_dynamic_import_target.ts
new file mode 100644
index 0000000000..226f1851a6
--- /dev/null
+++ b/tests/specs/run/_088_dynamic_import_already_evaluating/088_dynamic_import_target.ts
@@ -0,0 +1,3 @@
+console.log(1);
+await new Promise((r) => setTimeout(r, 100));
+console.log(2);
diff --git a/tests/specs/run/_088_dynamic_import_already_evaluating/__test__.jsonc b/tests/specs/run/_088_dynamic_import_already_evaluating/__test__.jsonc
new file mode 100644
index 0000000000..4ce912bf86
--- /dev/null
+++ b/tests/specs/run/_088_dynamic_import_already_evaluating/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read 088_dynamic_import_already_evaluating.ts",
+  "output": "088_dynamic_import_already_evaluating.ts.out"
+}
diff --git a/tests/testdata/run/091_use_define_for_class_fields.ts b/tests/specs/run/_091_use_define_for_class_fields/091_use_define_for_class_fields.ts
similarity index 100%
rename from tests/testdata/run/091_use_define_for_class_fields.ts
rename to tests/specs/run/_091_use_define_for_class_fields/091_use_define_for_class_fields.ts
diff --git a/tests/testdata/run/091_use_define_for_class_fields.ts.out b/tests/specs/run/_091_use_define_for_class_fields/091_use_define_for_class_fields.ts.out
similarity index 100%
rename from tests/testdata/run/091_use_define_for_class_fields.ts.out
rename to tests/specs/run/_091_use_define_for_class_fields/091_use_define_for_class_fields.ts.out
diff --git a/tests/specs/run/_091_use_define_for_class_fields/__test__.jsonc b/tests/specs/run/_091_use_define_for_class_fields/__test__.jsonc
new file mode 100644
index 0000000000..100db44aa8
--- /dev/null
+++ b/tests/specs/run/_091_use_define_for_class_fields/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --check 091_use_define_for_class_fields.ts",
+  "output": "091_use_define_for_class_fields.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/aggregate_error/__test__.jsonc b/tests/specs/run/aggregate_error/__test__.jsonc
new file mode 100644
index 0000000000..e9bd82481c
--- /dev/null
+++ b/tests/specs/run/aggregate_error/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet aggregate_error.ts",
+  "output": "aggregate_error.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/aggregate_error.out b/tests/specs/run/aggregate_error/aggregate_error.out
similarity index 100%
rename from tests/testdata/run/aggregate_error.out
rename to tests/specs/run/aggregate_error/aggregate_error.out
diff --git a/tests/testdata/run/aggregate_error.ts b/tests/specs/run/aggregate_error/aggregate_error.ts
similarity index 100%
rename from tests/testdata/run/aggregate_error.ts
rename to tests/specs/run/aggregate_error/aggregate_error.ts
diff --git a/tests/specs/run/allow_run_insecure_warnings/__test__.jsonc b/tests/specs/run/allow_run_insecure_warnings/__test__.jsonc
deleted file mode 100644
index b64146ee95..0000000000
--- a/tests/specs/run/allow_run_insecure_warnings/__test__.jsonc
+++ /dev/null
@@ -1,8 +0,0 @@
-{
-  "tests": {
-    "no_allow_list": {
-      "args": "run --allow-run main.ts",
-      "output": "no_allow_list.out"
-    }
-  }
-}
diff --git a/tests/specs/run/allow_run_insecure_warnings/no_allow_list.out b/tests/specs/run/allow_run_insecure_warnings/no_allow_list.out
deleted file mode 100644
index 293b4446ad..0000000000
--- a/tests/specs/run/allow_run_insecure_warnings/no_allow_list.out
+++ /dev/null
@@ -1 +0,0 @@
-Warning --allow-run without an allow list is susceptible to exploits. Prefer specifying an allow list (https://docs.deno.com/runtime/fundamentals/security/#running-subprocesses)
diff --git a/tests/specs/run/async_error/__test__.jsonc b/tests/specs/run/async_error/__test__.jsonc
new file mode 100644
index 0000000000..86c31adac7
--- /dev/null
+++ b/tests/specs/run/async_error/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload async_error.ts",
+  "output": "async_error.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/async_error.ts b/tests/specs/run/async_error/async_error.ts
similarity index 100%
rename from tests/testdata/run/async_error.ts
rename to tests/specs/run/async_error/async_error.ts
diff --git a/tests/testdata/run/async_error.ts.out b/tests/specs/run/async_error/async_error.ts.out
similarity index 100%
rename from tests/testdata/run/async_error.ts.out
rename to tests/specs/run/async_error/async_error.ts.out
diff --git a/tests/specs/run/beforeunload_event/__test__.jsonc b/tests/specs/run/beforeunload_event/__test__.jsonc
new file mode 100644
index 0000000000..01c7e70077
--- /dev/null
+++ b/tests/specs/run/beforeunload_event/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run before_unload.js",
+  "output": "before_unload.js.out"
+}
diff --git a/tests/testdata/run/before_unload.js b/tests/specs/run/beforeunload_event/before_unload.js
similarity index 100%
rename from tests/testdata/run/before_unload.js
rename to tests/specs/run/beforeunload_event/before_unload.js
diff --git a/tests/testdata/run/before_unload.js.out b/tests/specs/run/beforeunload_event/before_unload.js.out
similarity index 100%
rename from tests/testdata/run/before_unload.js.out
rename to tests/specs/run/beforeunload_event/before_unload.js.out
diff --git a/tests/specs/run/blob_gc_finalization/__test__.jsonc b/tests/specs/run/blob_gc_finalization/__test__.jsonc
new file mode 100644
index 0000000000..20a8128fce
--- /dev/null
+++ b/tests/specs/run/blob_gc_finalization/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run blob_gc_finalization.js",
+  "output": "blob_gc_finalization.js.out",
+  "exitCode": 0
+}
diff --git a/tests/testdata/run/blob_gc_finalization.js b/tests/specs/run/blob_gc_finalization/blob_gc_finalization.js
similarity index 100%
rename from tests/testdata/run/blob_gc_finalization.js
rename to tests/specs/run/blob_gc_finalization/blob_gc_finalization.js
diff --git a/tests/testdata/run/blob_gc_finalization.js.out b/tests/specs/run/blob_gc_finalization/blob_gc_finalization.js.out
similarity index 100%
rename from tests/testdata/run/blob_gc_finalization.js.out
rename to tests/specs/run/blob_gc_finalization/blob_gc_finalization.js.out
diff --git a/tests/specs/run/byte_order_mark/001_hello.js b/tests/specs/run/byte_order_mark/001_hello.js
new file mode 100644
index 0000000000..accefceba6
--- /dev/null
+++ b/tests/specs/run/byte_order_mark/001_hello.js
@@ -0,0 +1 @@
+console.log("Hello World");
diff --git a/tests/specs/run/byte_order_mark/__test__.jsonc b/tests/specs/run/byte_order_mark/__test__.jsonc
new file mode 100644
index 0000000000..f47cb7d025
--- /dev/null
+++ b/tests/specs/run/byte_order_mark/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --no-check byte_order_mark.ts",
+  "output": "byte_order_mark.out"
+}
diff --git a/tests/testdata/run/byte_order_mark.out b/tests/specs/run/byte_order_mark/byte_order_mark.out
similarity index 100%
rename from tests/testdata/run/byte_order_mark.out
rename to tests/specs/run/byte_order_mark/byte_order_mark.out
diff --git a/tests/testdata/run/byte_order_mark.ts b/tests/specs/run/byte_order_mark/byte_order_mark.ts
similarity index 86%
rename from tests/testdata/run/byte_order_mark.ts
rename to tests/specs/run/byte_order_mark/byte_order_mark.ts
index 40eb23c1d0..71da3e1e9c 100644
--- a/tests/testdata/run/byte_order_mark.ts
+++ b/tests/specs/run/byte_order_mark/byte_order_mark.ts
@@ -1,4 +1,4 @@
-import "./001_hello.js";
+import "./001_hello.js";
 // Note this file starts with special byte order mark <U+FEFF>
 // it's important that this file is a .ts typescript file which is passed to
 // deno through `--no-check` mode.
diff --git a/tests/specs/run/check_js_points_to_ts/__test__.jsonc b/tests/specs/run/check_js_points_to_ts/__test__.jsonc
new file mode 100644
index 0000000000..a63b9e5a46
--- /dev/null
+++ b/tests/specs/run/check_js_points_to_ts/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --check --config checkjs.tsconfig.json check_js_points_to_ts/test.js",
+  "output": "check_js_points_to_ts/test.js.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/check_js_points_to_ts/bar.ts b/tests/specs/run/check_js_points_to_ts/check_js_points_to_ts/bar.ts
similarity index 100%
rename from tests/testdata/run/check_js_points_to_ts/bar.ts
rename to tests/specs/run/check_js_points_to_ts/check_js_points_to_ts/bar.ts
diff --git a/tests/testdata/run/wasm_shared.out b/tests/specs/run/check_js_points_to_ts/check_js_points_to_ts/foo.d.ts
similarity index 100%
rename from tests/testdata/run/wasm_shared.out
rename to tests/specs/run/check_js_points_to_ts/check_js_points_to_ts/foo.d.ts
diff --git a/tests/testdata/run/check_js_points_to_ts/foo.js b/tests/specs/run/check_js_points_to_ts/check_js_points_to_ts/foo.js
similarity index 100%
rename from tests/testdata/run/check_js_points_to_ts/foo.js
rename to tests/specs/run/check_js_points_to_ts/check_js_points_to_ts/foo.js
diff --git a/tests/testdata/run/check_js_points_to_ts/test.js b/tests/specs/run/check_js_points_to_ts/check_js_points_to_ts/test.js
similarity index 100%
rename from tests/testdata/run/check_js_points_to_ts/test.js
rename to tests/specs/run/check_js_points_to_ts/check_js_points_to_ts/test.js
diff --git a/tests/testdata/run/check_js_points_to_ts/test.js.out b/tests/specs/run/check_js_points_to_ts/check_js_points_to_ts/test.js.out
similarity index 100%
rename from tests/testdata/run/check_js_points_to_ts/test.js.out
rename to tests/specs/run/check_js_points_to_ts/check_js_points_to_ts/test.js.out
diff --git a/tests/specs/run/check_js_points_to_ts/checkjs.tsconfig.json b/tests/specs/run/check_js_points_to_ts/checkjs.tsconfig.json
new file mode 100644
index 0000000000..08ac60b6cd
--- /dev/null
+++ b/tests/specs/run/check_js_points_to_ts/checkjs.tsconfig.json
@@ -0,0 +1,5 @@
+{
+  "compilerOptions": {
+    "checkJs": true
+  }
+}
diff --git a/tests/specs/run/check_remote/__test__.jsonc b/tests/specs/run/check_remote/__test__.jsonc
new file mode 100644
index 0000000000..6543e61b3f
--- /dev/null
+++ b/tests/specs/run/check_remote/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --allow-import --reload --check=all no_check_remote.ts",
+  "output": "no_check_remote.ts.disabled.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/check_remote/no_check_remote.ts b/tests/specs/run/check_remote/no_check_remote.ts
new file mode 100644
index 0000000000..f42dadf8a7
--- /dev/null
+++ b/tests/specs/run/check_remote/no_check_remote.ts
@@ -0,0 +1,3 @@
+import * as a from "./type_error.ts";
+
+console.log(a.a);
diff --git a/tests/testdata/run/no_check_remote.ts.disabled.out b/tests/specs/run/check_remote/no_check_remote.ts.disabled.out
similarity index 66%
rename from tests/testdata/run/no_check_remote.ts.disabled.out
rename to tests/specs/run/check_remote/no_check_remote.ts.disabled.out
index 3442646348..06c046072d 100644
--- a/tests/testdata/run/no_check_remote.ts.disabled.out
+++ b/tests/specs/run/check_remote/no_check_remote.ts.disabled.out
@@ -1,4 +1,4 @@
 error: TS2322 [ERROR]: Type '12' is not assignable to type '"a"'.
 export const a: "a" = 12;
              ^
-    at http://localhost:4545/subdir/type_error.ts:1:14
+    at [WILDCARD]/type_error.ts:1:14
diff --git a/tests/specs/run/check_remote/type_error.ts b/tests/specs/run/check_remote/type_error.ts
new file mode 100644
index 0000000000..cc3c1d29d8
--- /dev/null
+++ b/tests/specs/run/check_remote/type_error.ts
@@ -0,0 +1 @@
+export const a: "a" = 12;
diff --git a/tests/specs/run/cjs/main_module/__test__.jsonc b/tests/specs/run/cjs/main_module/__test__.jsonc
new file mode 100644
index 0000000000..e756a63627
--- /dev/null
+++ b/tests/specs/run/cjs/main_module/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read main.cjs",
+  "output": "main.out"
+}
diff --git a/tests/specs/run/cjs/main_module/main.cjs b/tests/specs/run/cjs/main_module/main.cjs
new file mode 100644
index 0000000000..2a4c57ab1c
--- /dev/null
+++ b/tests/specs/run/cjs/main_module/main.cjs
@@ -0,0 +1 @@
+console.log(require.main);
diff --git a/tests/specs/run/cjs/main_module/main.out b/tests/specs/run/cjs/main_module/main.out
new file mode 100644
index 0000000000..93b86d27e3
--- /dev/null
+++ b/tests/specs/run/cjs/main_module/main.out
@@ -0,0 +1,5 @@
+Module {
+  id: ".",
+  [WILDCARD]
+  filename: "[WILDCARD]main.cjs",
+[WILDCARD]
\ No newline at end of file
diff --git a/tests/specs/run/cjs_reexport_non_analyzable/__test__.jsonc b/tests/specs/run/cjs/reexport_non_analyzable/__test__.jsonc
similarity index 100%
rename from tests/specs/run/cjs_reexport_non_analyzable/__test__.jsonc
rename to tests/specs/run/cjs/reexport_non_analyzable/__test__.jsonc
diff --git a/tests/specs/run/cjs_reexport_non_analyzable/deno.json b/tests/specs/run/cjs/reexport_non_analyzable/deno.json
similarity index 100%
rename from tests/specs/run/cjs_reexport_non_analyzable/deno.json
rename to tests/specs/run/cjs/reexport_non_analyzable/deno.json
diff --git a/tests/specs/run/cjs_reexport_non_analyzable/main.ts b/tests/specs/run/cjs/reexport_non_analyzable/main.ts
similarity index 100%
rename from tests/specs/run/cjs_reexport_non_analyzable/main.ts
rename to tests/specs/run/cjs/reexport_non_analyzable/main.ts
diff --git a/tests/specs/run/cjs_reexport_non_analyzable/node_modules/foo.cjs b/tests/specs/run/cjs/reexport_non_analyzable/node_modules/foo.cjs
similarity index 100%
rename from tests/specs/run/cjs_reexport_non_analyzable/node_modules/foo.cjs
rename to tests/specs/run/cjs/reexport_non_analyzable/node_modules/foo.cjs
diff --git a/tests/specs/run/cjs/unprepared/__test__.jsonc b/tests/specs/run/cjs/unprepared/__test__.jsonc
new file mode 100644
index 0000000000..f816bad869
--- /dev/null
+++ b/tests/specs/run/cjs/unprepared/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run -A main.ts",
+  "output": "main.out"
+}
diff --git a/tests/specs/run/cjs/unprepared/file.cjs b/tests/specs/run/cjs/unprepared/file.cjs
new file mode 100644
index 0000000000..ba0c6fa6ff
--- /dev/null
+++ b/tests/specs/run/cjs/unprepared/file.cjs
@@ -0,0 +1,7 @@
+// non-analyzable
+const moduleName = "./output.cjs";
+function getModuleName() {
+  return moduleName;
+}
+
+require(getModuleName());
diff --git a/tests/testdata/run/import_extensionless.ts.out b/tests/specs/run/cjs/unprepared/main.out
similarity index 100%
rename from tests/testdata/run/import_extensionless.ts.out
rename to tests/specs/run/cjs/unprepared/main.out
diff --git a/tests/specs/run/cjs/unprepared/main.ts b/tests/specs/run/cjs/unprepared/main.ts
new file mode 100644
index 0000000000..5630b4fbc3
--- /dev/null
+++ b/tests/specs/run/cjs/unprepared/main.ts
@@ -0,0 +1,7 @@
+// non-analyzable
+const moduleName = "./output.cjs";
+function getModuleName() {
+  return moduleName;
+}
+
+await import(getModuleName());
diff --git a/tests/specs/run/cjs/unprepared/output.cjs b/tests/specs/run/cjs/unprepared/output.cjs
new file mode 100644
index 0000000000..54ed3702f5
--- /dev/null
+++ b/tests/specs/run/cjs/unprepared/output.cjs
@@ -0,0 +1,3 @@
+console.log("Hello");
+
+module.exports = 1;
diff --git a/tests/specs/run/classic_workers_event_loop/__test__.jsonc b/tests/specs/run/classic_workers_event_loop/__test__.jsonc
new file mode 100644
index 0000000000..44ea36bdc0
--- /dev/null
+++ b/tests/specs/run/classic_workers_event_loop/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --enable-testing-features-do-not-use classic_workers_event_loop.js",
+  "output": "classic_workers_event_loop.js.out"
+}
diff --git a/tests/testdata/run/classic_workers_event_loop.js b/tests/specs/run/classic_workers_event_loop/classic_workers_event_loop.js
similarity index 100%
rename from tests/testdata/run/classic_workers_event_loop.js
rename to tests/specs/run/classic_workers_event_loop/classic_workers_event_loop.js
diff --git a/tests/testdata/run/classic_workers_event_loop.js.out b/tests/specs/run/classic_workers_event_loop/classic_workers_event_loop.js.out
similarity index 100%
rename from tests/testdata/run/classic_workers_event_loop.js.out
rename to tests/specs/run/classic_workers_event_loop/classic_workers_event_loop.js.out
diff --git a/tests/specs/run/colors_without_global_this/__test__.jsonc b/tests/specs/run/colors_without_global_this/__test__.jsonc
new file mode 100644
index 0000000000..1d2f1c1cfe
--- /dev/null
+++ b/tests/specs/run/colors_without_global_this/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run colors_without_globalThis.js",
+  "output": "true\n"
+}
diff --git a/tests/testdata/run/colors_without_globalThis.js b/tests/specs/run/colors_without_global_this/colors_without_globalThis.js
similarity index 100%
rename from tests/testdata/run/colors_without_globalThis.js
rename to tests/specs/run/colors_without_global_this/colors_without_globalThis.js
diff --git a/tests/specs/run/complex_error/__test__.jsonc b/tests/specs/run/complex_error/__test__.jsonc
new file mode 100644
index 0000000000..2f7274be49
--- /dev/null
+++ b/tests/specs/run/complex_error/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet complex_error.ts",
+  "output": "complex_error.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/complex_error.ts b/tests/specs/run/complex_error/complex_error.ts
similarity index 100%
rename from tests/testdata/run/complex_error.ts
rename to tests/specs/run/complex_error/complex_error.ts
diff --git a/tests/testdata/run/complex_error.ts.out b/tests/specs/run/complex_error/complex_error.ts.out
similarity index 100%
rename from tests/testdata/run/complex_error.ts.out
rename to tests/specs/run/complex_error/complex_error.ts.out
diff --git a/tests/specs/run/config/__test__.jsonc b/tests/specs/run/config/__test__.jsonc
new file mode 100644
index 0000000000..59d3ae5fcc
--- /dev/null
+++ b/tests/specs/run/config/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload --config config/tsconfig.json --check config/main.ts",
+  "output": "config/main.out"
+}
diff --git a/tests/testdata/run/config/main.out b/tests/specs/run/config/config/main.out
similarity index 100%
rename from tests/testdata/run/config/main.out
rename to tests/specs/run/config/config/main.out
diff --git a/tests/testdata/run/config/main.ts b/tests/specs/run/config/config/main.ts
similarity index 100%
rename from tests/testdata/run/config/main.ts
rename to tests/specs/run/config/config/main.ts
diff --git a/tests/testdata/run/config/tsconfig.json b/tests/specs/run/config/config/tsconfig.json
similarity index 100%
rename from tests/testdata/run/config/tsconfig.json
rename to tests/specs/run/config/config/tsconfig.json
diff --git a/tests/specs/run/config_auto_discovered_for_local_script/__test__.jsonc b/tests/specs/run/config_auto_discovered_for_local_script/__test__.jsonc
new file mode 100644
index 0000000000..bd2a77ab1a
--- /dev/null
+++ b/tests/specs/run/config_auto_discovered_for_local_script/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet frontend_work.ts",
+  "output": "ok\n"
+}
diff --git a/tests/testdata/run/with_config/frontend_work.ts b/tests/specs/run/config_auto_discovered_for_local_script/frontend_work.ts
similarity index 100%
rename from tests/testdata/run/with_config/frontend_work.ts
rename to tests/specs/run/config_auto_discovered_for_local_script/frontend_work.ts
diff --git a/tests/specs/run/config_auto_discovered_for_local_script_log/__test__.jsonc b/tests/specs/run/config_auto_discovered_for_local_script_log/__test__.jsonc
new file mode 100644
index 0000000000..5182cc9589
--- /dev/null
+++ b/tests/specs/run/config_auto_discovered_for_local_script_log/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run -L debug frontend_work.ts",
+  "output": "auto_discovery_log.out"
+}
diff --git a/tests/testdata/run/with_config/auto_discovery_log.out b/tests/specs/run/config_auto_discovered_for_local_script_log/auto_discovery_log.out
similarity index 100%
rename from tests/testdata/run/with_config/auto_discovery_log.out
rename to tests/specs/run/config_auto_discovered_for_local_script_log/auto_discovery_log.out
diff --git a/tests/testdata/run/with_config/deno.jsonc b/tests/specs/run/config_auto_discovered_for_local_script_log/deno.jsonc
similarity index 100%
rename from tests/testdata/run/with_config/deno.jsonc
rename to tests/specs/run/config_auto_discovered_for_local_script_log/deno.jsonc
diff --git a/tests/specs/run/config_auto_discovered_for_local_script_log/frontend_work.ts b/tests/specs/run/config_auto_discovered_for_local_script_log/frontend_work.ts
new file mode 100644
index 0000000000..783af44e4c
--- /dev/null
+++ b/tests/specs/run/config_auto_discovered_for_local_script_log/frontend_work.ts
@@ -0,0 +1,4 @@
+function _main() {
+  console.log(document);
+}
+console.log("ok");
diff --git a/tests/specs/run/config_json_import/__test__.jsonc b/tests/specs/run/config_json_import/__test__.jsonc
new file mode 100644
index 0000000000..6ef632ff8d
--- /dev/null
+++ b/tests/specs/run/config_json_import/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet -c deno-jsx.json config_json_import.ts",
+  "output": "config_json_import.ts.out"
+}
diff --git a/tests/specs/run/config_json_import/config_json_import.ts b/tests/specs/run/config_json_import/config_json_import.ts
new file mode 100644
index 0000000000..4a772fac3f
--- /dev/null
+++ b/tests/specs/run/config_json_import/config_json_import.ts
@@ -0,0 +1,2 @@
+import config from "./deno-jsx.json" with { type: "json" };
+console.log(config);
diff --git a/tests/testdata/run/config_json_import.ts.out b/tests/specs/run/config_json_import/config_json_import.ts.out
similarity index 100%
rename from tests/testdata/run/config_json_import.ts.out
rename to tests/specs/run/config_json_import/config_json_import.ts.out
diff --git a/tests/specs/run/config_json_import/deno-jsx.json b/tests/specs/run/config_json_import/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/config_json_import/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/config_not_auto_discovered_for_remote_script/__test__.jsonc b/tests/specs/run/config_not_auto_discovered_for_remote_script/__test__.jsonc
new file mode 100644
index 0000000000..e6ccc02aca
--- /dev/null
+++ b/tests/specs/run/config_not_auto_discovered_for_remote_script/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --quiet server_side_work.ts",
+  "output": "ok\n"
+}
diff --git a/tests/testdata/run/with_config/server_side_work.ts b/tests/specs/run/config_not_auto_discovered_for_remote_script/server_side_work.ts
similarity index 100%
rename from tests/testdata/run/with_config/server_side_work.ts
rename to tests/specs/run/config_not_auto_discovered_for_remote_script/server_side_work.ts
diff --git a/tests/specs/run/config_types/__test__.jsonc b/tests/specs/run/config_types/__test__.jsonc
new file mode 100644
index 0000000000..d803915c73
--- /dev/null
+++ b/tests/specs/run/config_types/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload --quiet --check=all --config config_types/tsconfig.json config_types/main.ts",
+  "output": "config_types/main.out"
+}
diff --git a/tests/specs/run/config_types/config_types/deno.lock b/tests/specs/run/config_types/config_types/deno.lock
new file mode 100644
index 0000000000..157bd98a2e
--- /dev/null
+++ b/tests/specs/run/config_types/config_types/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/run/config_types/types.d.ts": "741c39165e37de0c12acc5c081841f4362487e3f17dc4cad7017b70af72c4605"
+  }
+}
diff --git a/tests/testdata/run/config_types/main.out b/tests/specs/run/config_types/config_types/main.out
similarity index 100%
rename from tests/testdata/run/config_types/main.out
rename to tests/specs/run/config_types/config_types/main.out
diff --git a/tests/testdata/run/config_types/main.ts b/tests/specs/run/config_types/config_types/main.ts
similarity index 100%
rename from tests/testdata/run/config_types/main.ts
rename to tests/specs/run/config_types/config_types/main.ts
diff --git a/tests/testdata/run/config_types/remote.tsconfig.json b/tests/specs/run/config_types/config_types/remote.tsconfig.json
similarity index 100%
rename from tests/testdata/run/config_types/remote.tsconfig.json
rename to tests/specs/run/config_types/config_types/remote.tsconfig.json
diff --git a/tests/testdata/run/config_types/tsconfig.json b/tests/specs/run/config_types/config_types/tsconfig.json
similarity index 100%
rename from tests/testdata/run/config_types/tsconfig.json
rename to tests/specs/run/config_types/config_types/tsconfig.json
diff --git a/tests/specs/run/config_types/config_types/types.d.ts b/tests/specs/run/config_types/config_types/types.d.ts
new file mode 100644
index 0000000000..536a6d0a69
--- /dev/null
+++ b/tests/specs/run/config_types/config_types/types.d.ts
@@ -0,0 +1,2 @@
+// deno-lint-ignore-file no-var
+declare var a: string;
diff --git a/tests/specs/run/config_types_remote/__test__.jsonc b/tests/specs/run/config_types_remote/__test__.jsonc
new file mode 100644
index 0000000000..87457ace21
--- /dev/null
+++ b/tests/specs/run/config_types_remote/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --reload --quiet --check=all --config config_types/remote.tsconfig.json config_types/main.ts",
+  "output": "config_types/main.out"
+}
diff --git a/tests/specs/run/config_types_remote/config_types/deno.lock b/tests/specs/run/config_types_remote/config_types/deno.lock
new file mode 100644
index 0000000000..157bd98a2e
--- /dev/null
+++ b/tests/specs/run/config_types_remote/config_types/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/run/config_types/types.d.ts": "741c39165e37de0c12acc5c081841f4362487e3f17dc4cad7017b70af72c4605"
+  }
+}
diff --git a/tests/testdata/run/reference_types.ts.out b/tests/specs/run/config_types_remote/config_types/main.out
similarity index 100%
rename from tests/testdata/run/reference_types.ts.out
rename to tests/specs/run/config_types_remote/config_types/main.out
diff --git a/tests/specs/run/config_types_remote/config_types/main.ts b/tests/specs/run/config_types_remote/config_types/main.ts
new file mode 100644
index 0000000000..f1a8d65831
--- /dev/null
+++ b/tests/specs/run/config_types_remote/config_types/main.ts
@@ -0,0 +1 @@
+console.log(globalThis.a);
diff --git a/tests/specs/run/config_types_remote/config_types/remote.tsconfig.json b/tests/specs/run/config_types_remote/config_types/remote.tsconfig.json
new file mode 100644
index 0000000000..255ff5def0
--- /dev/null
+++ b/tests/specs/run/config_types_remote/config_types/remote.tsconfig.json
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "types": [
+      "http://localhost:4545/run/config_types/types.d.ts"
+    ]
+  }
+}
diff --git a/tests/specs/run/config_types_remote/config_types/tsconfig.json b/tests/specs/run/config_types_remote/config_types/tsconfig.json
new file mode 100644
index 0000000000..85f1549e0d
--- /dev/null
+++ b/tests/specs/run/config_types_remote/config_types/tsconfig.json
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "types": [
+      "./types.d.ts"
+    ]
+  }
+}
diff --git a/tests/specs/run/config_types_remote/config_types/types.d.ts b/tests/specs/run/config_types_remote/config_types/types.d.ts
new file mode 100644
index 0000000000..536a6d0a69
--- /dev/null
+++ b/tests/specs/run/config_types_remote/config_types/types.d.ts
@@ -0,0 +1,2 @@
+// deno-lint-ignore-file no-var
+declare var a: string;
diff --git a/tests/specs/run/cts/cjs_import_cts/__test__.jsonc b/tests/specs/run/cts/cjs_import_cts/__test__.jsonc
new file mode 100644
index 0000000000..2205183d07
--- /dev/null
+++ b/tests/specs/run/cts/cjs_import_cts/__test__.jsonc
@@ -0,0 +1,13 @@
+{
+  "tests": {
+    "no_check": {
+      "args": "run --allow-read main.js",
+      "output": "main.out"
+    },
+    "check": {
+      "args": "check main.js",
+      "output": "check.out",
+      "exitCode": 1
+    }
+  }
+}
diff --git a/tests/specs/run/cts/cjs_import_cts/add.cts b/tests/specs/run/cts/cjs_import_cts/add.cts
new file mode 100644
index 0000000000..2a886fbc18
--- /dev/null
+++ b/tests/specs/run/cts/cjs_import_cts/add.cts
@@ -0,0 +1,3 @@
+module.exports.add = function (a, b) {
+  return a + b;
+};
diff --git a/tests/specs/run/cts/cjs_import_cts/check.out b/tests/specs/run/cts/cjs_import_cts/check.out
new file mode 100644
index 0000000000..a27e8d7af7
--- /dev/null
+++ b/tests/specs/run/cts/cjs_import_cts/check.out
@@ -0,0 +1,17 @@
+Check file:///[WILDLINE]main.js
+error: TS2580 [ERROR]: Cannot find name 'module'.
+module.exports.add = function (a, b) {
+~~~~~~
+    at file:///[WILDLINE]
+
+TS7006 [ERROR]: Parameter 'a' implicitly has an 'any' type.
+module.exports.add = function (a, b) {
+                               ^
+    at file:///[WILDLINE]
+
+TS7006 [ERROR]: Parameter 'b' implicitly has an 'any' type.
+module.exports.add = function (a, b) {
+                                  ^
+    at file:///[WILDLINE]
+
+Found 3 errors.
diff --git a/tests/specs/run/cts/cjs_import_cts/main.js b/tests/specs/run/cts/cjs_import_cts/main.js
new file mode 100644
index 0000000000..9546a0fea5
--- /dev/null
+++ b/tests/specs/run/cts/cjs_import_cts/main.js
@@ -0,0 +1,3 @@
+import { subtract } from "./subtract.cjs";
+
+console.log(subtract(1, 2));
diff --git a/tests/specs/run/cts/cjs_import_cts/main.out b/tests/specs/run/cts/cjs_import_cts/main.out
new file mode 100644
index 0000000000..3a2e3f4984
--- /dev/null
+++ b/tests/specs/run/cts/cjs_import_cts/main.out
@@ -0,0 +1 @@
+-1
diff --git a/tests/specs/run/cts/cjs_import_cts/subtract.cjs b/tests/specs/run/cts/cjs_import_cts/subtract.cjs
new file mode 100644
index 0000000000..7dee54346f
--- /dev/null
+++ b/tests/specs/run/cts/cjs_import_cts/subtract.cjs
@@ -0,0 +1,3 @@
+module.exports.subtract = function (a, b) {
+  return require("./add.cts").add(a, -b);
+};
diff --git a/tests/specs/run/cts/import_export_equals/__test__.jsonc b/tests/specs/run/cts/import_export_equals/__test__.jsonc
new file mode 100644
index 0000000000..6a5c6db420
--- /dev/null
+++ b/tests/specs/run/cts/import_export_equals/__test__.jsonc
@@ -0,0 +1,17 @@
+{
+  "tests": {
+    "main": {
+      "args": "run --check --allow-read=. main.cts",
+      "output": "main.out"
+    },
+    "mts": {
+      "args": "run --allow-read=. mod.mts",
+      "output": "mod.mts.out"
+    },
+    "mts_check": {
+      "args": "check mod.mts",
+      "output": "mod.mts.check.out",
+      "exitCode": 1
+    }
+  }
+}
diff --git a/tests/specs/run/cts/import_export_equals/add.cts b/tests/specs/run/cts/import_export_equals/add.cts
new file mode 100644
index 0000000000..adf3503ac5
--- /dev/null
+++ b/tests/specs/run/cts/import_export_equals/add.cts
@@ -0,0 +1,3 @@
+export = function (a: number, b: number) {
+  return a + b;
+};
diff --git a/tests/specs/run/cts/import_export_equals/main.cts b/tests/specs/run/cts/import_export_equals/main.cts
new file mode 100644
index 0000000000..e5c45f92e0
--- /dev/null
+++ b/tests/specs/run/cts/import_export_equals/main.cts
@@ -0,0 +1,3 @@
+import add = require("./add.cts");
+
+console.log(add(1, 2));
diff --git a/tests/specs/run/cts/import_export_equals/main.out b/tests/specs/run/cts/import_export_equals/main.out
new file mode 100644
index 0000000000..e7a973a7d0
--- /dev/null
+++ b/tests/specs/run/cts/import_export_equals/main.out
@@ -0,0 +1,2 @@
+Check file:///[WILDLINE]/main.cts
+3
diff --git a/tests/specs/run/cts/import_export_equals/mod.mts b/tests/specs/run/cts/import_export_equals/mod.mts
new file mode 100644
index 0000000000..5fbbd6c6a0
--- /dev/null
+++ b/tests/specs/run/cts/import_export_equals/mod.mts
@@ -0,0 +1,3 @@
+import add from "./add.cts";
+
+console.log(add(1, "test"));
diff --git a/tests/specs/run/cts/import_export_equals/mod.mts.check.out b/tests/specs/run/cts/import_export_equals/mod.mts.check.out
new file mode 100644
index 0000000000..8703539019
--- /dev/null
+++ b/tests/specs/run/cts/import_export_equals/mod.mts.check.out
@@ -0,0 +1,5 @@
+Check file:///[WILDLINE]/mod.mts
+error: TS2345 [ERROR]: Argument of type 'string' is not assignable to parameter of type 'number'.
+console.log(add(1, "test"));
+                   ~~~~~~
+    at file:///[WILDLINE]/mod.mts:3:20
diff --git a/tests/specs/run/cts/import_export_equals/mod.mts.out b/tests/specs/run/cts/import_export_equals/mod.mts.out
new file mode 100644
index 0000000000..208465a080
--- /dev/null
+++ b/tests/specs/run/cts/import_export_equals/mod.mts.out
@@ -0,0 +1 @@
+1test
diff --git a/tests/specs/run/cts/main/__test__.jsonc b/tests/specs/run/cts/main/__test__.jsonc
new file mode 100644
index 0000000000..0157b44e96
--- /dev/null
+++ b/tests/specs/run/cts/main/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read main.cts",
+  "output": "main.out"
+}
diff --git a/tests/specs/run/cts/main/import_main.cjs b/tests/specs/run/cts/main/import_main.cjs
new file mode 100644
index 0000000000..f61e0da2a6
--- /dev/null
+++ b/tests/specs/run/cts/main/import_main.cjs
@@ -0,0 +1 @@
+require("./main.cts").sayHello();
diff --git a/tests/specs/run/cts/main/main.cts b/tests/specs/run/cts/main/main.cts
new file mode 100644
index 0000000000..0b0330686b
--- /dev/null
+++ b/tests/specs/run/cts/main/main.cts
@@ -0,0 +1,5 @@
+module.exports.sayHello = function () {
+  console.log("Hello");
+};
+
+require("./import_main.cjs");
diff --git a/tests/testdata/run/issue13562.ts.out b/tests/specs/run/cts/main/main.out
similarity index 100%
rename from tests/testdata/run/issue13562.ts.out
rename to tests/specs/run/cts/main/main.out
diff --git a/tests/specs/run/custom_inspect_url/__test__.jsonc b/tests/specs/run/custom_inspect_url/__test__.jsonc
new file mode 100644
index 0000000000..1c1c2b9c47
--- /dev/null
+++ b/tests/specs/run/custom_inspect_url/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run custom_inspect_url.js",
+  "output": "custom_inspect_url.js.out"
+}
diff --git a/tests/testdata/run/custom_inspect_url.js b/tests/specs/run/custom_inspect_url/custom_inspect_url.js
similarity index 100%
rename from tests/testdata/run/custom_inspect_url.js
rename to tests/specs/run/custom_inspect_url/custom_inspect_url.js
diff --git a/tests/testdata/run/custom_inspect_url.js.out b/tests/specs/run/custom_inspect_url/custom_inspect_url.js.out
similarity index 100%
rename from tests/testdata/run/custom_inspect_url.js.out
rename to tests/specs/run/custom_inspect_url/custom_inspect_url.js.out
diff --git a/tests/specs/run/decorators_tc39_proposal/__test__.jsonc b/tests/specs/run/decorators_tc39_proposal/__test__.jsonc
new file mode 100644
index 0000000000..8e529695d9
--- /dev/null
+++ b/tests/specs/run/decorators_tc39_proposal/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --check decorators/tc39_proposal/main.ts",
+  "output": "decorators/tc39_proposal/main.out"
+}
diff --git a/tests/testdata/run/decorators/experimental/deno.json b/tests/specs/run/decorators_tc39_proposal/decorators/experimental/deno.json
similarity index 100%
rename from tests/testdata/run/decorators/experimental/deno.json
rename to tests/specs/run/decorators_tc39_proposal/decorators/experimental/deno.json
diff --git a/tests/testdata/run/decorators/experimental/no_check/main.out b/tests/specs/run/decorators_tc39_proposal/decorators/experimental/no_check/main.out
similarity index 100%
rename from tests/testdata/run/decorators/experimental/no_check/main.out
rename to tests/specs/run/decorators_tc39_proposal/decorators/experimental/no_check/main.out
diff --git a/tests/testdata/run/decorators/experimental/no_check/main.ts b/tests/specs/run/decorators_tc39_proposal/decorators/experimental/no_check/main.ts
similarity index 100%
rename from tests/testdata/run/decorators/experimental/no_check/main.ts
rename to tests/specs/run/decorators_tc39_proposal/decorators/experimental/no_check/main.ts
diff --git a/tests/testdata/run/decorators/experimental/runtime/main.out b/tests/specs/run/decorators_tc39_proposal/decorators/experimental/runtime/main.out
similarity index 100%
rename from tests/testdata/run/decorators/experimental/runtime/main.out
rename to tests/specs/run/decorators_tc39_proposal/decorators/experimental/runtime/main.out
diff --git a/tests/testdata/run/decorators/experimental/runtime/main.ts b/tests/specs/run/decorators_tc39_proposal/decorators/experimental/runtime/main.ts
similarity index 100%
rename from tests/testdata/run/decorators/experimental/runtime/main.ts
rename to tests/specs/run/decorators_tc39_proposal/decorators/experimental/runtime/main.ts
diff --git a/tests/testdata/run/decorators/experimental/ts/main.out b/tests/specs/run/decorators_tc39_proposal/decorators/experimental/ts/main.out
similarity index 100%
rename from tests/testdata/run/decorators/experimental/ts/main.out
rename to tests/specs/run/decorators_tc39_proposal/decorators/experimental/ts/main.out
diff --git a/tests/testdata/run/decorators/experimental/ts/main.ts b/tests/specs/run/decorators_tc39_proposal/decorators/experimental/ts/main.ts
similarity index 100%
rename from tests/testdata/run/decorators/experimental/ts/main.ts
rename to tests/specs/run/decorators_tc39_proposal/decorators/experimental/ts/main.ts
diff --git a/tests/testdata/run/decorators/tc39_proposal/main.out b/tests/specs/run/decorators_tc39_proposal/decorators/tc39_proposal/main.out
similarity index 100%
rename from tests/testdata/run/decorators/tc39_proposal/main.out
rename to tests/specs/run/decorators_tc39_proposal/decorators/tc39_proposal/main.out
diff --git a/tests/testdata/run/decorators/tc39_proposal/main.ts b/tests/specs/run/decorators_tc39_proposal/decorators/tc39_proposal/main.ts
similarity index 100%
rename from tests/testdata/run/decorators/tc39_proposal/main.ts
rename to tests/specs/run/decorators_tc39_proposal/decorators/tc39_proposal/main.ts
diff --git a/tests/specs/run/deno_exit_tampering/__test__.jsonc b/tests/specs/run/deno_exit_tampering/__test__.jsonc
new file mode 100644
index 0000000000..1666fbacb3
--- /dev/null
+++ b/tests/specs/run/deno_exit_tampering/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --no-check deno_exit_tampering.ts",
+  "output": "",
+  "exitCode": 42
+}
diff --git a/tests/testdata/run/deno_exit_tampering.ts b/tests/specs/run/deno_exit_tampering/deno_exit_tampering.ts
similarity index 100%
rename from tests/testdata/run/deno_exit_tampering.ts
rename to tests/specs/run/deno_exit_tampering/deno_exit_tampering.ts
diff --git a/tests/specs/run/deny_all_permission_args/__test__.jsonc b/tests/specs/run/deny_all_permission_args/__test__.jsonc
new file mode 100644
index 0000000000..1d6b286822
--- /dev/null
+++ b/tests/specs/run/deny_all_permission_args/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --deny-env --deny-read --deny-write --deny-ffi --deny-run --deny-sys --deny-net deny_all_permission_args.js",
+  "output": "deny_all_permission_args.out"
+}
diff --git a/tests/testdata/run/deny_all_permission_args.js b/tests/specs/run/deny_all_permission_args/deny_all_permission_args.js
similarity index 100%
rename from tests/testdata/run/deny_all_permission_args.js
rename to tests/specs/run/deny_all_permission_args/deny_all_permission_args.js
diff --git a/tests/testdata/run/deny_all_permission_args.out b/tests/specs/run/deny_all_permission_args/deny_all_permission_args.out
similarity index 100%
rename from tests/testdata/run/deny_all_permission_args.out
rename to tests/specs/run/deny_all_permission_args/deny_all_permission_args.out
diff --git a/tests/specs/run/deny_some_permission_args/__test__.jsonc b/tests/specs/run/deny_some_permission_args/__test__.jsonc
new file mode 100644
index 0000000000..a55ee57e48
--- /dev/null
+++ b/tests/specs/run/deny_some_permission_args/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-env --deny-env=FOO --allow-read --deny-read=/foo --allow-write --deny-write=/foo --allow-ffi --deny-ffi=/foo --allow-run --deny-run=foo --allow-sys --deny-sys=hostname --allow-net --deny-net=127.0.0.1 deny_some_permission_args.js",
+  "output": "deny_some_permission_args.out"
+}
diff --git a/tests/testdata/run/deny_some_permission_args.js b/tests/specs/run/deny_some_permission_args/deny_some_permission_args.js
similarity index 100%
rename from tests/testdata/run/deny_some_permission_args.js
rename to tests/specs/run/deny_some_permission_args/deny_some_permission_args.js
diff --git a/tests/testdata/run/deny_some_permission_args.out b/tests/specs/run/deny_some_permission_args/deny_some_permission_args.out
similarity index 87%
rename from tests/testdata/run/deny_some_permission_args.out
rename to tests/specs/run/deny_some_permission_args/deny_some_permission_args.out
index be2e832fec..abb5274eed 100644
--- a/tests/testdata/run/deny_some_permission_args.out
+++ b/tests/specs/run/deny_some_permission_args/deny_some_permission_args.out
@@ -1,4 +1,3 @@
-Warning --allow-run without an allow list is susceptible to exploits. Prefer specifying an allow list (https://docs.deno.com/runtime/fundamentals/security/#running-subprocesses)
 PermissionStatus { state: "granted", onchange: null, partial: true }
 PermissionStatus { state: "denied", onchange: null }
 PermissionStatus { state: "granted", onchange: null }
diff --git a/tests/specs/run/document/__test__.jsonc b/tests/specs/run/document/__test__.jsonc
new file mode 100644
index 0000000000..cf20f9e1b2
--- /dev/null
+++ b/tests/specs/run/document/__test__.jsonc
@@ -0,0 +1,9 @@
+{
+  "tests": {
+    "document": {
+      "args": "run document.js",
+      "exitCode": 1,
+      "output": "document.out"
+    }
+  }
+}
diff --git a/tests/specs/run/document/document.js b/tests/specs/run/document/document.js
new file mode 100644
index 0000000000..63e43b72f0
--- /dev/null
+++ b/tests/specs/run/document/document.js
@@ -0,0 +1 @@
+document.querySelector("div");
diff --git a/tests/specs/run/document/document.out b/tests/specs/run/document/document.out
new file mode 100644
index 0000000000..eefedb8f2b
--- /dev/null
+++ b/tests/specs/run/document/document.out
@@ -0,0 +1,8 @@
+error: Uncaught (in promise) ReferenceError: document is not defined
+document.querySelector("div");
+^
+    at [WILDCARD]document.js:1:1
+
+    info: document global is not available in Deno.
+    hint: Use a library like happy-dom, deno_dom, linkedom or JSDom
+          and setup the document global according to the library documentation.
diff --git a/tests/specs/run/dom_exception_formatting/__test__.jsonc b/tests/specs/run/dom_exception_formatting/__test__.jsonc
new file mode 100644
index 0000000000..5b1505b57b
--- /dev/null
+++ b/tests/specs/run/dom_exception_formatting/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run dom_exception_formatting.ts",
+  "output": "dom_exception_formatting.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/dom_exception_formatting.ts b/tests/specs/run/dom_exception_formatting/dom_exception_formatting.ts
similarity index 100%
rename from tests/testdata/run/dom_exception_formatting.ts
rename to tests/specs/run/dom_exception_formatting/dom_exception_formatting.ts
diff --git a/tests/testdata/run/dom_exception_formatting.ts.out b/tests/specs/run/dom_exception_formatting/dom_exception_formatting.ts.out
similarity index 100%
rename from tests/testdata/run/dom_exception_formatting.ts.out
rename to tests/specs/run/dom_exception_formatting/dom_exception_formatting.ts.out
diff --git a/tests/specs/run/dynamic_import_already_rejected/__test__.jsonc b/tests/specs/run/dynamic_import_already_rejected/__test__.jsonc
new file mode 100644
index 0000000000..0cd1201309
--- /dev/null
+++ b/tests/specs/run/dynamic_import_already_rejected/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read dynamic_import_already_rejected/main.ts",
+  "output": "dynamic_import_already_rejected/main.out"
+}
diff --git a/tests/testdata/run/dynamic_import_already_rejected/error_001.ts b/tests/specs/run/dynamic_import_already_rejected/dynamic_import_already_rejected/error_001.ts
similarity index 100%
rename from tests/testdata/run/dynamic_import_already_rejected/error_001.ts
rename to tests/specs/run/dynamic_import_already_rejected/dynamic_import_already_rejected/error_001.ts
diff --git a/tests/testdata/run/dynamic_import_already_rejected/main.out b/tests/specs/run/dynamic_import_already_rejected/dynamic_import_already_rejected/main.out
similarity index 100%
rename from tests/testdata/run/dynamic_import_already_rejected/main.out
rename to tests/specs/run/dynamic_import_already_rejected/dynamic_import_already_rejected/main.out
diff --git a/tests/testdata/run/dynamic_import_already_rejected/main.ts b/tests/specs/run/dynamic_import_already_rejected/dynamic_import_already_rejected/main.ts
similarity index 100%
rename from tests/testdata/run/dynamic_import_already_rejected/main.ts
rename to tests/specs/run/dynamic_import_already_rejected/dynamic_import_already_rejected/main.ts
diff --git a/tests/specs/run/dynamic_import_async_error/__test__.jsonc b/tests/specs/run/dynamic_import_async_error/__test__.jsonc
new file mode 100644
index 0000000000..9824c34508
--- /dev/null
+++ b/tests/specs/run/dynamic_import_async_error/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read dynamic_import_async_error/main.ts",
+  "output": "dynamic_import_async_error/main.out"
+}
diff --git a/tests/testdata/run/dynamic_import_async_error/delayed_error.ts b/tests/specs/run/dynamic_import_async_error/dynamic_import_async_error/delayed_error.ts
similarity index 100%
rename from tests/testdata/run/dynamic_import_async_error/delayed_error.ts
rename to tests/specs/run/dynamic_import_async_error/dynamic_import_async_error/delayed_error.ts
diff --git a/tests/testdata/run/dynamic_import_async_error/main.out b/tests/specs/run/dynamic_import_async_error/dynamic_import_async_error/main.out
similarity index 100%
rename from tests/testdata/run/dynamic_import_async_error/main.out
rename to tests/specs/run/dynamic_import_async_error/dynamic_import_async_error/main.out
diff --git a/tests/testdata/run/dynamic_import_async_error/main.ts b/tests/specs/run/dynamic_import_async_error/dynamic_import_async_error/main.ts
similarity index 100%
rename from tests/testdata/run/dynamic_import_async_error/main.ts
rename to tests/specs/run/dynamic_import_async_error/dynamic_import_async_error/main.ts
diff --git a/tests/specs/run/dynamic_import_concurrent_non_statically_analyzable/__test__.jsonc b/tests/specs/run/dynamic_import_concurrent_non_statically_analyzable/__test__.jsonc
new file mode 100644
index 0000000000..c4c30ca5d4
--- /dev/null
+++ b/tests/specs/run/dynamic_import_concurrent_non_statically_analyzable/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --allow-read --allow-net --quiet dynamic_import_concurrent_non_statically_analyzable/main.ts",
+  "output": "dynamic_import_concurrent_non_statically_analyzable/main.out"
+}
diff --git a/tests/testdata/run/dynamic_import_concurrent_non_statically_analyzable/main.out b/tests/specs/run/dynamic_import_concurrent_non_statically_analyzable/dynamic_import_concurrent_non_statically_analyzable/main.out
similarity index 100%
rename from tests/testdata/run/dynamic_import_concurrent_non_statically_analyzable/main.out
rename to tests/specs/run/dynamic_import_concurrent_non_statically_analyzable/dynamic_import_concurrent_non_statically_analyzable/main.out
diff --git a/tests/testdata/run/dynamic_import_concurrent_non_statically_analyzable/main.ts b/tests/specs/run/dynamic_import_concurrent_non_statically_analyzable/dynamic_import_concurrent_non_statically_analyzable/main.ts
similarity index 100%
rename from tests/testdata/run/dynamic_import_concurrent_non_statically_analyzable/main.ts
rename to tests/specs/run/dynamic_import_concurrent_non_statically_analyzable/dynamic_import_concurrent_non_statically_analyzable/main.ts
diff --git a/tests/testdata/run/dynamic_import_concurrent_non_statically_analyzable/mod.ts b/tests/specs/run/dynamic_import_concurrent_non_statically_analyzable/dynamic_import_concurrent_non_statically_analyzable/mod.ts
similarity index 100%
rename from tests/testdata/run/dynamic_import_concurrent_non_statically_analyzable/mod.ts
rename to tests/specs/run/dynamic_import_concurrent_non_statically_analyzable/dynamic_import_concurrent_non_statically_analyzable/mod.ts
diff --git a/tests/specs/run/dynamic_import_conditional/__test__.jsonc b/tests/specs/run/dynamic_import_conditional/__test__.jsonc
new file mode 100644
index 0000000000..8adff3a16d
--- /dev/null
+++ b/tests/specs/run/dynamic_import_conditional/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload dynamic_import_conditional.js",
+  "output": "dynamic_import_conditional.js.out"
+}
diff --git a/tests/testdata/run/dynamic_import_conditional.js b/tests/specs/run/dynamic_import_conditional/dynamic_import_conditional.js
similarity index 100%
rename from tests/testdata/run/dynamic_import_conditional.js
rename to tests/specs/run/dynamic_import_conditional/dynamic_import_conditional.js
diff --git a/tests/testdata/run/dynamic_import_conditional.js.out b/tests/specs/run/dynamic_import_conditional/dynamic_import_conditional.js.out
similarity index 100%
rename from tests/testdata/run/dynamic_import_conditional.js.out
rename to tests/specs/run/dynamic_import_conditional/dynamic_import_conditional.js.out
diff --git a/tests/specs/run/dynamic_import_permissions_blob_local/__test__.jsonc b/tests/specs/run/dynamic_import_permissions_blob_local/__test__.jsonc
new file mode 100644
index 0000000000..27a747b3a5
--- /dev/null
+++ b/tests/specs/run/dynamic_import_permissions_blob_local/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --reload --allow-net=localhost:4545 permissions_blob_local.ts",
+  "output": "permissions_blob_local.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/dynamic_import_permissions_blob_local/permissions_blob_local.ts b/tests/specs/run/dynamic_import_permissions_blob_local/permissions_blob_local.ts
new file mode 100644
index 0000000000..865c1777a9
--- /dev/null
+++ b/tests/specs/run/dynamic_import_permissions_blob_local/permissions_blob_local.ts
@@ -0,0 +1,6 @@
+// This file doesn't really exist, but it doesn't matter, a "NotCapable" error should be thrown.
+const code = `import "file:///${
+  Deno.build.os == "windows" ? "C:/" : ""
+}local_file.ts";`;
+const blob = new Blob([code]);
+await import(URL.createObjectURL(blob));
diff --git a/tests/specs/run/dynamic_import_permissions_blob_local/permissions_blob_local.ts.out b/tests/specs/run/dynamic_import_permissions_blob_local/permissions_blob_local.ts.out
new file mode 100644
index 0000000000..b7b246ba2b
--- /dev/null
+++ b/tests/specs/run/dynamic_import_permissions_blob_local/permissions_blob_local.ts.out
@@ -0,0 +1,5 @@
+error: Uncaught (in promise) TypeError: Requires read access to "[WILDCARD]local_file.ts", run again with the --allow-read flag
+    at blob:null/[WILDCARD]:1:8
+await import(URL.createObjectURL(blob));
+^
+    at async file://[WILDCARD]/permissions_blob_local.ts:6:1
diff --git a/tests/specs/run/dynamic_import_permissions_blob_remote/__test__.jsonc b/tests/specs/run/dynamic_import_permissions_blob_remote/__test__.jsonc
new file mode 100644
index 0000000000..f9d66b6b38
--- /dev/null
+++ b/tests/specs/run/dynamic_import_permissions_blob_remote/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --reload --allow-net=localhost:4545 permissions_blob_remote.ts",
+  "output": "permissions_blob_remote.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/dynamic_import_permissions_blob_remote/permissions_blob_remote.ts b/tests/specs/run/dynamic_import_permissions_blob_remote/permissions_blob_remote.ts
new file mode 100644
index 0000000000..569b1f84c5
--- /dev/null
+++ b/tests/specs/run/dynamic_import_permissions_blob_remote/permissions_blob_remote.ts
@@ -0,0 +1,3 @@
+const code = `import "https://example.com/some/file.ts";`;
+const blob = new Blob([code]);
+await import(URL.createObjectURL(blob));
diff --git a/tests/specs/run/dynamic_import_permissions_blob_remote/permissions_blob_remote.ts.out b/tests/specs/run/dynamic_import_permissions_blob_remote/permissions_blob_remote.ts.out
new file mode 100644
index 0000000000..287cf99985
--- /dev/null
+++ b/tests/specs/run/dynamic_import_permissions_blob_remote/permissions_blob_remote.ts.out
@@ -0,0 +1,5 @@
+error: Uncaught (in promise) TypeError: Requires import access to "example.com:443", run again with the --allow-import flag
+    at blob:null/[WILDCARD]:1:8
+await import(URL.createObjectURL(blob));
+^
+    at async file:///[WILDCARD]/permissions_blob_remote.ts:3:1
diff --git a/tests/specs/run/dynamic_import_permissions_data_local/__test__.jsonc b/tests/specs/run/dynamic_import_permissions_data_local/__test__.jsonc
new file mode 100644
index 0000000000..8f118d8be3
--- /dev/null
+++ b/tests/specs/run/dynamic_import_permissions_data_local/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --reload --allow-net=localhost:4545 permissions_data_local.ts",
+  "output": "permissions_data_local.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/dynamic_import_permissions_data_local/permissions_data_local.ts b/tests/specs/run/dynamic_import_permissions_data_local/permissions_data_local.ts
new file mode 100644
index 0000000000..01bff7d7a2
--- /dev/null
+++ b/tests/specs/run/dynamic_import_permissions_data_local/permissions_data_local.ts
@@ -0,0 +1,5 @@
+// This file doesn't really exist, but it doesn't matter, a "NotCapable" error should be thrown.
+const code = `import "file:///${
+  Deno.build.os == "windows" ? "C:/" : ""
+}local_file.ts";`;
+await import(`data:application/javascript;base64,${btoa(code)}`);
diff --git a/tests/specs/run/dynamic_import_permissions_data_local/permissions_data_local.ts.out b/tests/specs/run/dynamic_import_permissions_data_local/permissions_data_local.ts.out
new file mode 100644
index 0000000000..bf8c1948e6
--- /dev/null
+++ b/tests/specs/run/dynamic_import_permissions_data_local/permissions_data_local.ts.out
@@ -0,0 +1,5 @@
+error: Uncaught (in promise) TypeError: Requires read access to "[WILDCARD]local_file.ts", run again with the --allow-read flag
+    at data:application/javascript;base64,[WILDCARD]:1:8
+await import(`data:application/javascript;base64,${btoa(code)}`);
+^
+    at async file:///[WILDCARD]/permissions_data_local.ts:5:1
diff --git a/tests/specs/run/dynamic_import_permissions_data_remote/__test__.jsonc b/tests/specs/run/dynamic_import_permissions_data_remote/__test__.jsonc
new file mode 100644
index 0000000000..5b2c0c568f
--- /dev/null
+++ b/tests/specs/run/dynamic_import_permissions_data_remote/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --reload --allow-import=localhost:4545 permissions_data_remote.ts",
+  "output": "permissions_data_remote.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/dynamic_import_permissions_data_remote/permissions_data_remote.ts b/tests/specs/run/dynamic_import_permissions_data_remote/permissions_data_remote.ts
new file mode 100644
index 0000000000..b0a9540c32
--- /dev/null
+++ b/tests/specs/run/dynamic_import_permissions_data_remote/permissions_data_remote.ts
@@ -0,0 +1,3 @@
+// This file doesn't really exist, but it doesn't matter, a "PermissionsDenied" error should be thrown.
+const code = `import "https://example.com/some/file.ts";`;
+await import(`data:application/javascript;base64,${btoa(code)}`);
diff --git a/tests/specs/run/dynamic_import_permissions_data_remote/permissions_data_remote.ts.out b/tests/specs/run/dynamic_import_permissions_data_remote/permissions_data_remote.ts.out
new file mode 100644
index 0000000000..c8de9382a5
--- /dev/null
+++ b/tests/specs/run/dynamic_import_permissions_data_remote/permissions_data_remote.ts.out
@@ -0,0 +1,5 @@
+error: Uncaught (in promise) TypeError: Requires import access to "example.com:443", run again with the --allow-import flag
+    at data:application/javascript;base64,aW1wb3J0ICJodHRwczovL2V4YW1wbGUuY29tL3NvbWUvZmlsZS50cyI7:1:8
+await import(`data:application/javascript;base64,${btoa(code)}`);
+^
+    at async file:///[WILDCARD]/permissions_data_remote.ts:3:1
diff --git a/tests/specs/run/dynamic_import_permissions_remote_remote/__test__.jsonc b/tests/specs/run/dynamic_import_permissions_remote_remote/__test__.jsonc
new file mode 100644
index 0000000000..00fd2a6e4c
--- /dev/null
+++ b/tests/specs/run/dynamic_import_permissions_remote_remote/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --reload --allow-import=localhost:4545 permissions_remote_remote.ts",
+  "output": "permissions_remote_remote.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/dynamic_import_permissions_remote_remote/permissions_remote_remote.ts b/tests/specs/run/dynamic_import_permissions_remote_remote/permissions_remote_remote.ts
new file mode 100644
index 0000000000..65a2541910
--- /dev/null
+++ b/tests/specs/run/dynamic_import_permissions_remote_remote/permissions_remote_remote.ts
@@ -0,0 +1,3 @@
+await import(
+  "" + "http://localhost:4545/dynamic_import/static_remote.ts"
+);
diff --git a/tests/specs/run/dynamic_import_permissions_remote_remote/permissions_remote_remote.ts.out b/tests/specs/run/dynamic_import_permissions_remote_remote/permissions_remote_remote.ts.out
new file mode 100644
index 0000000000..16fe3bbdd6
--- /dev/null
+++ b/tests/specs/run/dynamic_import_permissions_remote_remote/permissions_remote_remote.ts.out
@@ -0,0 +1,5 @@
+error: Uncaught (in promise) TypeError: Requires import access to "example.com:443", run again with the --allow-import flag
+    at http://localhost:4545/dynamic_import/static_remote.ts:2:8
+await import(
+^
+    at async file:///[WILDCARD]/permissions_remote_remote.ts:1:1
diff --git a/tests/specs/run/dynamic_import_permissions_remote_remote/static_remote.ts b/tests/specs/run/dynamic_import_permissions_remote_remote/static_remote.ts
new file mode 100644
index 0000000000..2d6e820fd6
--- /dev/null
+++ b/tests/specs/run/dynamic_import_permissions_remote_remote/static_remote.ts
@@ -0,0 +1,2 @@
+// This file doesn't really exist, but it doesn't matter, a "PermissionsDenied" error should be thrown.
+import "https://example.com/some/file.ts";
diff --git a/tests/specs/run/dynamic_import_static_analysis_no_permissions/__test__.jsonc b/tests/specs/run/dynamic_import_static_analysis_no_permissions/__test__.jsonc
new file mode 100644
index 0000000000..9379748691
--- /dev/null
+++ b/tests/specs/run/dynamic_import_static_analysis_no_permissions/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --no-prompt static_analysis_no_permissions.ts",
+  "output": "static_analysis_no_permissions.ts.out"
+}
diff --git a/tests/testdata/run/worker_close_race.js.out b/tests/specs/run/dynamic_import_static_analysis_no_permissions/empty_1.ts
similarity index 100%
rename from tests/testdata/run/worker_close_race.js.out
rename to tests/specs/run/dynamic_import_static_analysis_no_permissions/empty_1.ts
diff --git a/tests/specs/run/dynamic_import_static_analysis_no_permissions/empty_2.ts b/tests/specs/run/dynamic_import_static_analysis_no_permissions/empty_2.ts
new file mode 100644
index 0000000000..e69de29bb2
diff --git a/tests/specs/run/dynamic_import_static_analysis_no_permissions/static_analysis_no_permissions.ts b/tests/specs/run/dynamic_import_static_analysis_no_permissions/static_analysis_no_permissions.ts
new file mode 100644
index 0000000000..de75ba87b6
--- /dev/null
+++ b/tests/specs/run/dynamic_import_static_analysis_no_permissions/static_analysis_no_permissions.ts
@@ -0,0 +1,13 @@
+try {
+  await import("./empty_1.ts");
+  console.log("✅ Succeeded importing statically analyzable specifier");
+} catch {
+  console.log("❌ Failed importing statically analyzable specifier");
+}
+
+try {
+  await import("" + "./empty_2.ts");
+  console.log("❌ Succeeded importing non-statically analyzable specifier");
+} catch {
+  console.log("✅ Failed importing non-statically analyzable specifier");
+}
diff --git a/tests/specs/run/dynamic_import_static_analysis_no_permissions/static_analysis_no_permissions.ts.out b/tests/specs/run/dynamic_import_static_analysis_no_permissions/static_analysis_no_permissions.ts.out
new file mode 100644
index 0000000000..ba9249ab0b
--- /dev/null
+++ b/tests/specs/run/dynamic_import_static_analysis_no_permissions/static_analysis_no_permissions.ts.out
@@ -0,0 +1,2 @@
+✅ Succeeded importing statically analyzable specifier
+✅ Failed importing non-statically analyzable specifier
diff --git a/tests/specs/run/dynamic_import_syntax_error/__test__.jsonc b/tests/specs/run/dynamic_import_syntax_error/__test__.jsonc
new file mode 100644
index 0000000000..1971d3184c
--- /dev/null
+++ b/tests/specs/run/dynamic_import_syntax_error/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run -A dynamic_import_syntax_error.js",
+  "output": "dynamic_import_syntax_error.js.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/dynamic_import_syntax_error.js b/tests/specs/run/dynamic_import_syntax_error/dynamic_import_syntax_error.js
similarity index 100%
rename from tests/testdata/run/dynamic_import_syntax_error.js
rename to tests/specs/run/dynamic_import_syntax_error/dynamic_import_syntax_error.js
diff --git a/tests/testdata/run/dynamic_import_syntax_error.js.out b/tests/specs/run/dynamic_import_syntax_error/dynamic_import_syntax_error.js.out
similarity index 100%
rename from tests/testdata/run/dynamic_import_syntax_error.js.out
rename to tests/specs/run/dynamic_import_syntax_error/dynamic_import_syntax_error.js.out
diff --git a/tests/specs/run/dynamic_import_syntax_error/dynamic_import_syntax_error_import.js b/tests/specs/run/dynamic_import_syntax_error/dynamic_import_syntax_error_import.js
new file mode 100644
index 0000000000..bcf0756385
--- /dev/null
+++ b/tests/specs/run/dynamic_import_syntax_error/dynamic_import_syntax_error_import.js
@@ -0,0 +1,5 @@
+// deno-lint-ignore-file
+function foo() {
+  await Promise.resolve();
+}
+foo();
diff --git a/tests/specs/run/empty_typescript/__test__.jsonc b/tests/specs/run/empty_typescript/__test__.jsonc
new file mode 100644
index 0000000000..8090c50f68
--- /dev/null
+++ b/tests/specs/run/empty_typescript/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload --check empty.ts",
+  "output": "Check file:[WILDCARD]/empty.ts\n"
+}
diff --git a/tests/specs/run/empty_typescript/empty.ts b/tests/specs/run/empty_typescript/empty.ts
new file mode 100644
index 0000000000..e69de29bb2
diff --git a/tests/specs/run/error_001/__test__.jsonc b/tests/specs/run/error_001/__test__.jsonc
new file mode 100644
index 0000000000..7b9158e4f5
--- /dev/null
+++ b/tests/specs/run/error_001/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload error_001.ts",
+  "output": "error_001.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/error_001/error_001.ts b/tests/specs/run/error_001/error_001.ts
new file mode 100644
index 0000000000..b01068bc01
--- /dev/null
+++ b/tests/specs/run/error_001/error_001.ts
@@ -0,0 +1,9 @@
+function foo(): never {
+  throw Error("bad");
+}
+
+function bar() {
+  foo();
+}
+
+bar();
diff --git a/tests/testdata/run/error_001.ts.out b/tests/specs/run/error_001/error_001.ts.out
similarity index 100%
rename from tests/testdata/run/error_001.ts.out
rename to tests/specs/run/error_001/error_001.ts.out
diff --git a/tests/specs/run/error_002/__test__.jsonc b/tests/specs/run/error_002/__test__.jsonc
new file mode 100644
index 0000000000..3a68a86751
--- /dev/null
+++ b/tests/specs/run/error_002/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload error_002.ts",
+  "output": "error_002.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/error_002/error_002.ts b/tests/specs/run/error_002/error_002.ts
new file mode 100644
index 0000000000..ac712fbf71
--- /dev/null
+++ b/tests/specs/run/error_002/error_002.ts
@@ -0,0 +1,7 @@
+import { throwsError } from "./mod1.ts";
+
+function foo() {
+  throwsError();
+}
+
+foo();
diff --git a/tests/testdata/run/error_002.ts.out b/tests/specs/run/error_002/error_002.ts.out
similarity index 78%
rename from tests/testdata/run/error_002.ts.out
rename to tests/specs/run/error_002/error_002.ts.out
index 9fec5d968a..1051e7360c 100644
--- a/tests/testdata/run/error_002.ts.out
+++ b/tests/specs/run/error_002/error_002.ts.out
@@ -1,6 +1,6 @@
 [WILDCARD]error: Uncaught (in promise) Error: exception from mod1
   throw Error("exception from mod1");
         ^
-    at throwsError ([WILDCARD]/subdir/mod1.ts:16:9)
+    at throwsError ([WILDCARD]/mod1.ts:16:9)
     at foo ([WILDCARD]/error_002.ts:4:3)
     at [WILDCARD]/error_002.ts:7:1
diff --git a/tests/specs/run/error_002/mod1.ts b/tests/specs/run/error_002/mod1.ts
new file mode 100644
index 0000000000..5e58f432ed
--- /dev/null
+++ b/tests/specs/run/error_002/mod1.ts
@@ -0,0 +1,17 @@
+import { printHello2, returnsFoo } from "./subdir2/mod2.ts";
+
+export function returnsHi(): string {
+  return "Hi";
+}
+
+export function returnsFoo2(): string {
+  return returnsFoo();
+}
+
+export function printHello3() {
+  printHello2();
+}
+
+export function throwsError() {
+  throw Error("exception from mod1");
+}
diff --git a/tests/specs/run/error_002/print_hello.ts b/tests/specs/run/error_002/print_hello.ts
new file mode 100644
index 0000000000..b9c0ad5275
--- /dev/null
+++ b/tests/specs/run/error_002/print_hello.ts
@@ -0,0 +1,3 @@
+export function printHello() {
+  console.log("Hello");
+}
diff --git a/tests/specs/run/error_002/subdir2/mod2.ts b/tests/specs/run/error_002/subdir2/mod2.ts
new file mode 100644
index 0000000000..9071d0aeb4
--- /dev/null
+++ b/tests/specs/run/error_002/subdir2/mod2.ts
@@ -0,0 +1,9 @@
+import { printHello } from "../print_hello.ts";
+
+export function returnsFoo(): string {
+  return "Foo";
+}
+
+export function printHello2() {
+  printHello();
+}
diff --git a/tests/specs/run/error_003_typescript/__test__.jsonc b/tests/specs/run/error_003_typescript/__test__.jsonc
new file mode 100644
index 0000000000..f7ef69b268
--- /dev/null
+++ b/tests/specs/run/error_003_typescript/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload --check error_003_typescript.ts",
+  "output": "error_003_typescript.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_003_typescript.ts b/tests/specs/run/error_003_typescript/error_003_typescript.ts
similarity index 100%
rename from tests/testdata/run/error_003_typescript.ts
rename to tests/specs/run/error_003_typescript/error_003_typescript.ts
diff --git a/tests/testdata/run/error_003_typescript.ts.out b/tests/specs/run/error_003_typescript/error_003_typescript.ts.out
similarity index 100%
rename from tests/testdata/run/error_003_typescript.ts.out
rename to tests/specs/run/error_003_typescript/error_003_typescript.ts.out
diff --git a/tests/specs/run/error_003_typescript2/__test__.jsonc b/tests/specs/run/error_003_typescript2/__test__.jsonc
new file mode 100644
index 0000000000..ceeb6e7d94
--- /dev/null
+++ b/tests/specs/run/error_003_typescript2/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --check error_003_typescript.ts",
+  "output": "error_003_typescript.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/error_003_typescript2/error_003_typescript.ts b/tests/specs/run/error_003_typescript2/error_003_typescript.ts
new file mode 100644
index 0000000000..e1f882123c
--- /dev/null
+++ b/tests/specs/run/error_003_typescript2/error_003_typescript.ts
@@ -0,0 +1,20 @@
+// deno-lint-ignore-file
+let x = {
+  a: {
+    b: {
+      c() {
+        return { d: "hello" };
+      },
+    },
+  },
+};
+let y = {
+  a: {
+    b: {
+      c() {
+        return { d: 1234 };
+      },
+    },
+  },
+};
+x = y;
diff --git a/tests/specs/run/error_003_typescript2/error_003_typescript.ts.out b/tests/specs/run/error_003_typescript2/error_003_typescript.ts.out
new file mode 100644
index 0000000000..bbb2ec4708
--- /dev/null
+++ b/tests/specs/run/error_003_typescript2/error_003_typescript.ts.out
@@ -0,0 +1,7 @@
+[WILDCARD]
+error: TS2322 [ERROR]: Type '{ a: { b: { c(): { d: number; }; }; }; }' is not assignable to type '{ a: { b: { c(): { d: string; }; }; }; }'.
+  The types of 'a.b.c().d' are incompatible between these types.
+    Type 'number' is not assignable to type 'string'.
+x = y;
+^
+    at [WILDCARD]/error_003_typescript.ts:20:1
diff --git a/tests/specs/run/error_004_missing_module/__test__.jsonc b/tests/specs/run/error_004_missing_module/__test__.jsonc
new file mode 100644
index 0000000000..824b9d8c9c
--- /dev/null
+++ b/tests/specs/run/error_004_missing_module/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload error_004_missing_module.ts",
+  "output": "error_004_missing_module.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_004_missing_module.ts b/tests/specs/run/error_004_missing_module/error_004_missing_module.ts
similarity index 100%
rename from tests/testdata/run/error_004_missing_module.ts
rename to tests/specs/run/error_004_missing_module/error_004_missing_module.ts
diff --git a/tests/testdata/run/error_004_missing_module.ts.out b/tests/specs/run/error_004_missing_module/error_004_missing_module.ts.out
similarity index 100%
rename from tests/testdata/run/error_004_missing_module.ts.out
rename to tests/specs/run/error_004_missing_module/error_004_missing_module.ts.out
diff --git a/tests/specs/run/error_005_missing_dynamic_import/__test__.jsonc b/tests/specs/run/error_005_missing_dynamic_import/__test__.jsonc
new file mode 100644
index 0000000000..b9f6a1b747
--- /dev/null
+++ b/tests/specs/run/error_005_missing_dynamic_import/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload --allow-read --quiet error_005_missing_dynamic_import.ts",
+  "output": "error_005_missing_dynamic_import.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_005_missing_dynamic_import.ts b/tests/specs/run/error_005_missing_dynamic_import/error_005_missing_dynamic_import.ts
similarity index 100%
rename from tests/testdata/run/error_005_missing_dynamic_import.ts
rename to tests/specs/run/error_005_missing_dynamic_import/error_005_missing_dynamic_import.ts
diff --git a/tests/testdata/run/error_005_missing_dynamic_import.ts.out b/tests/specs/run/error_005_missing_dynamic_import/error_005_missing_dynamic_import.ts.out
similarity index 100%
rename from tests/testdata/run/error_005_missing_dynamic_import.ts.out
rename to tests/specs/run/error_005_missing_dynamic_import/error_005_missing_dynamic_import.ts.out
diff --git a/tests/specs/run/error_006_import_ext_failure/__test__.jsonc b/tests/specs/run/error_006_import_ext_failure/__test__.jsonc
new file mode 100644
index 0000000000..0e70bdcaf6
--- /dev/null
+++ b/tests/specs/run/error_006_import_ext_failure/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload error_006_import_ext_failure.ts",
+  "output": "error_006_import_ext_failure.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_006_import_ext_failure.ts b/tests/specs/run/error_006_import_ext_failure/error_006_import_ext_failure.ts
similarity index 100%
rename from tests/testdata/run/error_006_import_ext_failure.ts
rename to tests/specs/run/error_006_import_ext_failure/error_006_import_ext_failure.ts
diff --git a/tests/testdata/run/error_006_import_ext_failure.ts.out b/tests/specs/run/error_006_import_ext_failure/error_006_import_ext_failure.ts.out
similarity index 100%
rename from tests/testdata/run/error_006_import_ext_failure.ts.out
rename to tests/specs/run/error_006_import_ext_failure/error_006_import_ext_failure.ts.out
diff --git a/tests/specs/run/error_007_any/__test__.jsonc b/tests/specs/run/error_007_any/__test__.jsonc
new file mode 100644
index 0000000000..8a1c0d27e6
--- /dev/null
+++ b/tests/specs/run/error_007_any/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload error_007_any.ts",
+  "output": "error_007_any.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_007_any.ts b/tests/specs/run/error_007_any/error_007_any.ts
similarity index 100%
rename from tests/testdata/run/error_007_any.ts
rename to tests/specs/run/error_007_any/error_007_any.ts
diff --git a/tests/testdata/run/error_007_any.ts.out b/tests/specs/run/error_007_any/error_007_any.ts.out
similarity index 100%
rename from tests/testdata/run/error_007_any.ts.out
rename to tests/specs/run/error_007_any/error_007_any.ts.out
diff --git a/tests/specs/run/error_008_checkjs/__test__.jsonc b/tests/specs/run/error_008_checkjs/__test__.jsonc
new file mode 100644
index 0000000000..f735be953c
--- /dev/null
+++ b/tests/specs/run/error_008_checkjs/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload error_008_checkjs.js",
+  "output": "error_008_checkjs.js.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_008_checkjs.js b/tests/specs/run/error_008_checkjs/error_008_checkjs.js
similarity index 100%
rename from tests/testdata/run/error_008_checkjs.js
rename to tests/specs/run/error_008_checkjs/error_008_checkjs.js
diff --git a/tests/testdata/run/error_008_checkjs.js.out b/tests/specs/run/error_008_checkjs/error_008_checkjs.js.out
similarity index 100%
rename from tests/testdata/run/error_008_checkjs.js.out
rename to tests/specs/run/error_008_checkjs/error_008_checkjs.js.out
diff --git a/tests/specs/run/error_009_extensions_error/__test__.jsonc b/tests/specs/run/error_009_extensions_error/__test__.jsonc
new file mode 100644
index 0000000000..740d5119f5
--- /dev/null
+++ b/tests/specs/run/error_009_extensions_error/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run error_009_extensions_error.js",
+  "output": "error_009_extensions_error.js.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_009_extensions_error.js b/tests/specs/run/error_009_extensions_error/error_009_extensions_error.js
similarity index 100%
rename from tests/testdata/run/error_009_extensions_error.js
rename to tests/specs/run/error_009_extensions_error/error_009_extensions_error.js
diff --git a/tests/testdata/run/error_009_extensions_error.js.out b/tests/specs/run/error_009_extensions_error/error_009_extensions_error.js.out
similarity index 100%
rename from tests/testdata/run/error_009_extensions_error.js.out
rename to tests/specs/run/error_009_extensions_error/error_009_extensions_error.js.out
diff --git a/tests/specs/run/error_011_bad_module_specifier/__test__.jsonc b/tests/specs/run/error_011_bad_module_specifier/__test__.jsonc
new file mode 100644
index 0000000000..5ca5146bec
--- /dev/null
+++ b/tests/specs/run/error_011_bad_module_specifier/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload error_011_bad_module_specifier.ts",
+  "output": "error_011_bad_module_specifier.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_011_bad_module_specifier.ts b/tests/specs/run/error_011_bad_module_specifier/error_011_bad_module_specifier.ts
similarity index 100%
rename from tests/testdata/run/error_011_bad_module_specifier.ts
rename to tests/specs/run/error_011_bad_module_specifier/error_011_bad_module_specifier.ts
diff --git a/tests/testdata/run/error_011_bad_module_specifier.ts.out b/tests/specs/run/error_011_bad_module_specifier/error_011_bad_module_specifier.ts.out
similarity index 100%
rename from tests/testdata/run/error_011_bad_module_specifier.ts.out
rename to tests/specs/run/error_011_bad_module_specifier/error_011_bad_module_specifier.ts.out
diff --git a/tests/specs/run/error_012_bad_dynamic_import_specifier/__test__.jsonc b/tests/specs/run/error_012_bad_dynamic_import_specifier/__test__.jsonc
new file mode 100644
index 0000000000..9344f730dc
--- /dev/null
+++ b/tests/specs/run/error_012_bad_dynamic_import_specifier/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload --check error_012_bad_dynamic_import_specifier.ts",
+  "output": "error_012_bad_dynamic_import_specifier.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_012_bad_dynamic_import_specifier.ts b/tests/specs/run/error_012_bad_dynamic_import_specifier/error_012_bad_dynamic_import_specifier.ts
similarity index 100%
rename from tests/testdata/run/error_012_bad_dynamic_import_specifier.ts
rename to tests/specs/run/error_012_bad_dynamic_import_specifier/error_012_bad_dynamic_import_specifier.ts
diff --git a/tests/testdata/run/error_012_bad_dynamic_import_specifier.ts.out b/tests/specs/run/error_012_bad_dynamic_import_specifier/error_012_bad_dynamic_import_specifier.ts.out
similarity index 100%
rename from tests/testdata/run/error_012_bad_dynamic_import_specifier.ts.out
rename to tests/specs/run/error_012_bad_dynamic_import_specifier/error_012_bad_dynamic_import_specifier.ts.out
diff --git a/tests/specs/run/error_014_catch_dynamic_import_error/__test__.jsonc b/tests/specs/run/error_014_catch_dynamic_import_error/__test__.jsonc
new file mode 100644
index 0000000000..94957dc659
--- /dev/null
+++ b/tests/specs/run/error_014_catch_dynamic_import_error/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run  --reload --allow-read error_014_catch_dynamic_import_error.js",
+  "output": "error_014_catch_dynamic_import_error.js.out"
+}
diff --git a/tests/testdata/run/error_014_catch_dynamic_import_error.js b/tests/specs/run/error_014_catch_dynamic_import_error/error_014_catch_dynamic_import_error.js
similarity index 79%
rename from tests/testdata/run/error_014_catch_dynamic_import_error.js
rename to tests/specs/run/error_014_catch_dynamic_import_error/error_014_catch_dynamic_import_error.js
index c58e54dcbb..05b021d15d 100644
--- a/tests/testdata/run/error_014_catch_dynamic_import_error.js
+++ b/tests/specs/run/error_014_catch_dynamic_import_error/error_014_catch_dynamic_import_error.js
@@ -7,21 +7,21 @@
   }
 
   try {
-    await import("../subdir/indirect_import_error.js");
+    await import("./indirect_import_error.js");
   } catch (err) {
     console.log("Caught indirect direct dynamic import error.");
     console.log(err);
   }
 
   try {
-    await import("../subdir/throws.js");
+    await import("./throws.js");
   } catch (err) {
     console.log("Caught error thrown by dynamically imported module.");
     console.log(err);
   }
 
   try {
-    await import("../subdir/indirect_throws.js");
+    await import("./indirect_throws.js");
   } catch (err) {
     console.log(
       "Caught error thrown indirectly by dynamically imported module.",
diff --git a/tests/testdata/run/error_014_catch_dynamic_import_error.js.out b/tests/specs/run/error_014_catch_dynamic_import_error/error_014_catch_dynamic_import_error.js.out
similarity index 83%
rename from tests/testdata/run/error_014_catch_dynamic_import_error.js.out
rename to tests/specs/run/error_014_catch_dynamic_import_error/error_014_catch_dynamic_import_error.js.out
index 868c971940..71feaa55bf 100644
--- a/tests/testdata/run/error_014_catch_dynamic_import_error.js.out
+++ b/tests/specs/run/error_014_catch_dynamic_import_error/error_014_catch_dynamic_import_error.js.out
@@ -7,13 +7,13 @@ TypeError: Relative import path "does not exist" not prefixed with / or ./ or ..
 }
 Caught indirect direct dynamic import error.
 TypeError: Relative import path "does not exist either" not prefixed with / or ./ or ../
-    at [WILDCARD]/subdir/indirect_import_error.js:1:15
+    at [WILDCARD]/indirect_import_error.js:1:15
     at async [WILDCARD]/error_014_catch_dynamic_import_error.js:10:5 {
   code: "ERR_MODULE_NOT_FOUND"
 }
 Caught error thrown by dynamically imported module.
 Error: An error
-    at [WILDCARD]/subdir/throws.js:6:7
+    at [WILDCARD]/throws.js:6:7
 Caught error thrown indirectly by dynamically imported module.
 Error: An error
-    at [WILDCARD]/subdir/throws.js:6:7
+    at [WILDCARD]/throws.js:6:7
diff --git a/tests/specs/run/error_014_catch_dynamic_import_error/indirect_import_error.js b/tests/specs/run/error_014_catch_dynamic_import_error/indirect_import_error.js
new file mode 100644
index 0000000000..84011d2913
--- /dev/null
+++ b/tests/specs/run/error_014_catch_dynamic_import_error/indirect_import_error.js
@@ -0,0 +1 @@
+export * from "does not exist either";
diff --git a/tests/specs/run/error_014_catch_dynamic_import_error/indirect_throws.js b/tests/specs/run/error_014_catch_dynamic_import_error/indirect_throws.js
new file mode 100644
index 0000000000..e1810a66cb
--- /dev/null
+++ b/tests/specs/run/error_014_catch_dynamic_import_error/indirect_throws.js
@@ -0,0 +1 @@
+export * from "./throws.js";
diff --git a/tests/specs/run/error_014_catch_dynamic_import_error/throws.js b/tests/specs/run/error_014_catch_dynamic_import_error/throws.js
new file mode 100644
index 0000000000..abdf291568
--- /dev/null
+++ b/tests/specs/run/error_014_catch_dynamic_import_error/throws.js
@@ -0,0 +1,6 @@
+// deno-lint-ignore-file
+export function boo() {
+  console.log("Boo!");
+}
+
+throw new Error("An error");
diff --git a/tests/specs/run/error_015_dynamic_import_permissions/__test__.jsonc b/tests/specs/run/error_015_dynamic_import_permissions/__test__.jsonc
new file mode 100644
index 0000000000..3ab25f1a52
--- /dev/null
+++ b/tests/specs/run/error_015_dynamic_import_permissions/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload --quiet error_015_dynamic_import_permissions.js",
+  "output": "error_015_dynamic_import_permissions.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/error_015_dynamic_import_permissions/error_015_dynamic_import_permissions.js b/tests/specs/run/error_015_dynamic_import_permissions/error_015_dynamic_import_permissions.js
new file mode 100644
index 0000000000..6e7daf5d01
--- /dev/null
+++ b/tests/specs/run/error_015_dynamic_import_permissions/error_015_dynamic_import_permissions.js
@@ -0,0 +1,3 @@
+(async () => {
+  await import("" + "http://example.com/mod4.js");
+})();
diff --git a/tests/testdata/run/error_015_dynamic_import_permissions.out b/tests/specs/run/error_015_dynamic_import_permissions/error_015_dynamic_import_permissions.out
similarity index 77%
rename from tests/testdata/run/error_015_dynamic_import_permissions.out
rename to tests/specs/run/error_015_dynamic_import_permissions/error_015_dynamic_import_permissions.out
index 15c26b4251..8ef2f6f1e4 100644
--- a/tests/testdata/run/error_015_dynamic_import_permissions.out
+++ b/tests/specs/run/error_015_dynamic_import_permissions/error_015_dynamic_import_permissions.out
@@ -1,4 +1,4 @@
 error: Uncaught (in promise) TypeError: Requires import access to "example.com:80", run again with the --allow-import flag
-  await import("" + "http://example.com/subdir/mod4.js");
+  await import("" + "http://example.com/mod4.js");
   ^
     at async file://[WILDCARD]/error_015_dynamic_import_permissions.js:2:3
diff --git a/tests/specs/run/error_015_dynamic_import_permissions/mod4.js b/tests/specs/run/error_015_dynamic_import_permissions/mod4.js
new file mode 100644
index 0000000000..71332dbc42
--- /dev/null
+++ b/tests/specs/run/error_015_dynamic_import_permissions/mod4.js
@@ -0,0 +1 @@
+export const isMod4 = true;
diff --git a/tests/specs/run/error_017_hide_long_source_ts/__test__.jsonc b/tests/specs/run/error_017_hide_long_source_ts/__test__.jsonc
new file mode 100644
index 0000000000..382d560391
--- /dev/null
+++ b/tests/specs/run/error_017_hide_long_source_ts/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload --check error_017_hide_long_source_ts.ts",
+  "output": "error_017_hide_long_source_ts.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_017_hide_long_source_ts.ts b/tests/specs/run/error_017_hide_long_source_ts/error_017_hide_long_source_ts.ts
similarity index 100%
rename from tests/testdata/run/error_017_hide_long_source_ts.ts
rename to tests/specs/run/error_017_hide_long_source_ts/error_017_hide_long_source_ts.ts
diff --git a/tests/testdata/run/error_017_hide_long_source_ts.ts.out b/tests/specs/run/error_017_hide_long_source_ts/error_017_hide_long_source_ts.ts.out
similarity index 100%
rename from tests/testdata/run/error_017_hide_long_source_ts.ts.out
rename to tests/specs/run/error_017_hide_long_source_ts/error_017_hide_long_source_ts.ts.out
diff --git a/tests/specs/run/error_018_hide_long_source_js/__test__.jsonc b/tests/specs/run/error_018_hide_long_source_js/__test__.jsonc
new file mode 100644
index 0000000000..4e91a820df
--- /dev/null
+++ b/tests/specs/run/error_018_hide_long_source_js/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run error_018_hide_long_source_js.js",
+  "output": "error_018_hide_long_source_js.js.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_018_hide_long_source_js.js b/tests/specs/run/error_018_hide_long_source_js/error_018_hide_long_source_js.js
similarity index 100%
rename from tests/testdata/run/error_018_hide_long_source_js.js
rename to tests/specs/run/error_018_hide_long_source_js/error_018_hide_long_source_js.js
diff --git a/tests/testdata/run/error_018_hide_long_source_js.js.out b/tests/specs/run/error_018_hide_long_source_js/error_018_hide_long_source_js.js.out
similarity index 100%
rename from tests/testdata/run/error_018_hide_long_source_js.js.out
rename to tests/specs/run/error_018_hide_long_source_js/error_018_hide_long_source_js.js.out
diff --git a/tests/specs/run/error_019_stack_function/__test__.jsonc b/tests/specs/run/error_019_stack_function/__test__.jsonc
new file mode 100644
index 0000000000..5e272ee492
--- /dev/null
+++ b/tests/specs/run/error_019_stack_function/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run error_019_stack_function.ts",
+  "output": "error_019_stack_function.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_019_stack_function.ts b/tests/specs/run/error_019_stack_function/error_019_stack_function.ts
similarity index 100%
rename from tests/testdata/run/error_019_stack_function.ts
rename to tests/specs/run/error_019_stack_function/error_019_stack_function.ts
diff --git a/tests/testdata/run/error_019_stack_function.ts.out b/tests/specs/run/error_019_stack_function/error_019_stack_function.ts.out
similarity index 100%
rename from tests/testdata/run/error_019_stack_function.ts.out
rename to tests/specs/run/error_019_stack_function/error_019_stack_function.ts.out
diff --git a/tests/specs/run/error_020_stack_constructor/__test__.jsonc b/tests/specs/run/error_020_stack_constructor/__test__.jsonc
new file mode 100644
index 0000000000..2dd574565e
--- /dev/null
+++ b/tests/specs/run/error_020_stack_constructor/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run error_020_stack_constructor.ts",
+  "output": "error_020_stack_constructor.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_020_stack_constructor.ts b/tests/specs/run/error_020_stack_constructor/error_020_stack_constructor.ts
similarity index 100%
rename from tests/testdata/run/error_020_stack_constructor.ts
rename to tests/specs/run/error_020_stack_constructor/error_020_stack_constructor.ts
diff --git a/tests/testdata/run/error_020_stack_constructor.ts.out b/tests/specs/run/error_020_stack_constructor/error_020_stack_constructor.ts.out
similarity index 100%
rename from tests/testdata/run/error_020_stack_constructor.ts.out
rename to tests/specs/run/error_020_stack_constructor/error_020_stack_constructor.ts.out
diff --git a/tests/specs/run/error_021_stack_method/__test__.jsonc b/tests/specs/run/error_021_stack_method/__test__.jsonc
new file mode 100644
index 0000000000..db78cac094
--- /dev/null
+++ b/tests/specs/run/error_021_stack_method/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run error_021_stack_method.ts",
+  "output": "error_021_stack_method.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_021_stack_method.ts b/tests/specs/run/error_021_stack_method/error_021_stack_method.ts
similarity index 100%
rename from tests/testdata/run/error_021_stack_method.ts
rename to tests/specs/run/error_021_stack_method/error_021_stack_method.ts
diff --git a/tests/testdata/run/error_021_stack_method.ts.out b/tests/specs/run/error_021_stack_method/error_021_stack_method.ts.out
similarity index 100%
rename from tests/testdata/run/error_021_stack_method.ts.out
rename to tests/specs/run/error_021_stack_method/error_021_stack_method.ts.out
diff --git a/tests/specs/run/error_022_stack_custom_error/__test__.jsonc b/tests/specs/run/error_022_stack_custom_error/__test__.jsonc
new file mode 100644
index 0000000000..f315058338
--- /dev/null
+++ b/tests/specs/run/error_022_stack_custom_error/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run error_022_stack_custom_error.ts",
+  "output": "error_022_stack_custom_error.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_022_stack_custom_error.ts b/tests/specs/run/error_022_stack_custom_error/error_022_stack_custom_error.ts
similarity index 100%
rename from tests/testdata/run/error_022_stack_custom_error.ts
rename to tests/specs/run/error_022_stack_custom_error/error_022_stack_custom_error.ts
diff --git a/tests/testdata/run/error_022_stack_custom_error.ts.out b/tests/specs/run/error_022_stack_custom_error/error_022_stack_custom_error.ts.out
similarity index 100%
rename from tests/testdata/run/error_022_stack_custom_error.ts.out
rename to tests/specs/run/error_022_stack_custom_error/error_022_stack_custom_error.ts.out
diff --git a/tests/specs/run/error_023_stack_async/__test__.jsonc b/tests/specs/run/error_023_stack_async/__test__.jsonc
new file mode 100644
index 0000000000..76cdff013d
--- /dev/null
+++ b/tests/specs/run/error_023_stack_async/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run error_023_stack_async.ts",
+  "output": "error_023_stack_async.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_023_stack_async.ts b/tests/specs/run/error_023_stack_async/error_023_stack_async.ts
similarity index 100%
rename from tests/testdata/run/error_023_stack_async.ts
rename to tests/specs/run/error_023_stack_async/error_023_stack_async.ts
diff --git a/tests/testdata/run/error_023_stack_async.ts.out b/tests/specs/run/error_023_stack_async/error_023_stack_async.ts.out
similarity index 100%
rename from tests/testdata/run/error_023_stack_async.ts.out
rename to tests/specs/run/error_023_stack_async/error_023_stack_async.ts.out
diff --git a/tests/specs/run/error_024_stack_promise_all/__test__.jsonc b/tests/specs/run/error_024_stack_promise_all/__test__.jsonc
new file mode 100644
index 0000000000..7c733f9711
--- /dev/null
+++ b/tests/specs/run/error_024_stack_promise_all/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run error_024_stack_promise_all.ts",
+  "output": "error_024_stack_promise_all.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_024_stack_promise_all.ts b/tests/specs/run/error_024_stack_promise_all/error_024_stack_promise_all.ts
similarity index 100%
rename from tests/testdata/run/error_024_stack_promise_all.ts
rename to tests/specs/run/error_024_stack_promise_all/error_024_stack_promise_all.ts
diff --git a/tests/testdata/run/error_024_stack_promise_all.ts.out b/tests/specs/run/error_024_stack_promise_all/error_024_stack_promise_all.ts.out
similarity index 100%
rename from tests/testdata/run/error_024_stack_promise_all.ts.out
rename to tests/specs/run/error_024_stack_promise_all/error_024_stack_promise_all.ts.out
diff --git a/tests/specs/run/error_025_tab_indent/__test__.jsonc b/tests/specs/run/error_025_tab_indent/__test__.jsonc
new file mode 100644
index 0000000000..23c49458e5
--- /dev/null
+++ b/tests/specs/run/error_025_tab_indent/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run error_025_tab_indent",
+  "output": "error_025_tab_indent.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_025_tab_indent b/tests/specs/run/error_025_tab_indent/error_025_tab_indent
similarity index 100%
rename from tests/testdata/run/error_025_tab_indent
rename to tests/specs/run/error_025_tab_indent/error_025_tab_indent
diff --git a/tests/testdata/run/error_025_tab_indent.out b/tests/specs/run/error_025_tab_indent/error_025_tab_indent.out
similarity index 100%
rename from tests/testdata/run/error_025_tab_indent.out
rename to tests/specs/run/error_025_tab_indent/error_025_tab_indent.out
diff --git a/tests/specs/run/error_cause/__test__.jsonc b/tests/specs/run/error_cause/__test__.jsonc
new file mode 100644
index 0000000000..ccbf71dea7
--- /dev/null
+++ b/tests/specs/run/error_cause/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run error_cause.ts",
+  "output": "error_cause.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_cause.ts b/tests/specs/run/error_cause/error_cause.ts
similarity index 100%
rename from tests/testdata/run/error_cause.ts
rename to tests/specs/run/error_cause/error_cause.ts
diff --git a/tests/testdata/run/error_cause.ts.out b/tests/specs/run/error_cause/error_cause.ts.out
similarity index 100%
rename from tests/testdata/run/error_cause.ts.out
rename to tests/specs/run/error_cause/error_cause.ts.out
diff --git a/tests/specs/run/error_cause_recursive/__test__.jsonc b/tests/specs/run/error_cause_recursive/__test__.jsonc
new file mode 100644
index 0000000000..71c4cf3cc1
--- /dev/null
+++ b/tests/specs/run/error_cause_recursive/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run error_cause_recursive.ts",
+  "output": "error_cause_recursive.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_cause_recursive.ts b/tests/specs/run/error_cause_recursive/error_cause_recursive.ts
similarity index 100%
rename from tests/testdata/run/error_cause_recursive.ts
rename to tests/specs/run/error_cause_recursive/error_cause_recursive.ts
diff --git a/tests/testdata/run/error_cause_recursive.ts.out b/tests/specs/run/error_cause_recursive/error_cause_recursive.ts.out
similarity index 100%
rename from tests/testdata/run/error_cause_recursive.ts.out
rename to tests/specs/run/error_cause_recursive/error_cause_recursive.ts.out
diff --git a/tests/specs/run/error_cause_recursive_aggregate/__test__.jsonc b/tests/specs/run/error_cause_recursive_aggregate/__test__.jsonc
new file mode 100644
index 0000000000..2aabee0ecb
--- /dev/null
+++ b/tests/specs/run/error_cause_recursive_aggregate/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run error_cause_recursive_aggregate.ts",
+  "output": "error_cause_recursive_aggregate.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/error_cause_recursive_aggregate.ts b/tests/specs/run/error_cause_recursive_aggregate/error_cause_recursive_aggregate.ts
similarity index 100%
rename from tests/testdata/error_cause_recursive_aggregate.ts
rename to tests/specs/run/error_cause_recursive_aggregate/error_cause_recursive_aggregate.ts
diff --git a/tests/testdata/error_cause_recursive_aggregate.ts.out b/tests/specs/run/error_cause_recursive_aggregate/error_cause_recursive_aggregate.ts.out
similarity index 100%
rename from tests/testdata/error_cause_recursive_aggregate.ts.out
rename to tests/specs/run/error_cause_recursive_aggregate/error_cause_recursive_aggregate.ts.out
diff --git a/tests/specs/run/error_cause_recursive_tail/__test__.jsonc b/tests/specs/run/error_cause_recursive_tail/__test__.jsonc
new file mode 100644
index 0000000000..249ccac483
--- /dev/null
+++ b/tests/specs/run/error_cause_recursive_tail/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run error_cause_recursive_tail.ts",
+  "output": "error_cause_recursive_tail.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/error_cause_recursive_tail.ts b/tests/specs/run/error_cause_recursive_tail/error_cause_recursive_tail.ts
similarity index 100%
rename from tests/testdata/error_cause_recursive_tail.ts
rename to tests/specs/run/error_cause_recursive_tail/error_cause_recursive_tail.ts
diff --git a/tests/testdata/error_cause_recursive_tail.ts.out b/tests/specs/run/error_cause_recursive_tail/error_cause_recursive_tail.ts.out
similarity index 100%
rename from tests/testdata/error_cause_recursive_tail.ts.out
rename to tests/specs/run/error_cause_recursive_tail/error_cause_recursive_tail.ts.out
diff --git a/tests/specs/run/error_for_await/__test__.jsonc b/tests/specs/run/error_for_await/__test__.jsonc
new file mode 100644
index 0000000000..b67f67ecee
--- /dev/null
+++ b/tests/specs/run/error_for_await/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload --check error_for_await.ts",
+  "output": "error_for_await.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_for_await.ts b/tests/specs/run/error_for_await/error_for_await.ts
similarity index 100%
rename from tests/testdata/run/error_for_await.ts
rename to tests/specs/run/error_for_await/error_for_await.ts
diff --git a/tests/testdata/run/error_for_await.ts.out b/tests/specs/run/error_for_await/error_for_await.ts.out
similarity index 100%
rename from tests/testdata/run/error_for_await.ts.out
rename to tests/specs/run/error_for_await/error_for_await.ts.out
diff --git a/tests/specs/run/error_import_map_unable_to_load/__test__.jsonc b/tests/specs/run/error_import_map_unable_to_load/__test__.jsonc
new file mode 100644
index 0000000000..c7dd939a45
--- /dev/null
+++ b/tests/specs/run/error_import_map_unable_to_load/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --import-map=import_maps/does_not_exist.json import_maps/test.ts",
+  "output": "error_import_map_unable_to_load.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_import_map_unable_to_load.out b/tests/specs/run/error_import_map_unable_to_load/error_import_map_unable_to_load.out
similarity index 100%
rename from tests/testdata/run/error_import_map_unable_to_load.out
rename to tests/specs/run/error_import_map_unable_to_load/error_import_map_unable_to_load.out
diff --git a/tests/specs/run/error_import_map_unable_to_load/import_maps/test_data.ts b/tests/specs/run/error_import_map_unable_to_load/import_maps/test_data.ts
new file mode 100644
index 0000000000..5e8efea69b
--- /dev/null
+++ b/tests/specs/run/error_import_map_unable_to_load/import_maps/test_data.ts
@@ -0,0 +1 @@
+import "test_server/import_maps/lodash/lodash.ts";
diff --git a/tests/specs/run/error_import_map_unable_to_load/import_maps/test_data.ts.out b/tests/specs/run/error_import_map_unable_to_load/import_maps/test_data.ts.out
new file mode 100644
index 0000000000..da996dc0d9
--- /dev/null
+++ b/tests/specs/run/error_import_map_unable_to_load/import_maps/test_data.ts.out
@@ -0,0 +1 @@
+Hello from remapped lodash!
diff --git a/tests/specs/run/error_missing_module_named_import/__test__.jsonc b/tests/specs/run/error_missing_module_named_import/__test__.jsonc
new file mode 100644
index 0000000000..9f5780d2a9
--- /dev/null
+++ b/tests/specs/run/error_missing_module_named_import/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload error_missing_module_named_import.ts",
+  "output": "error_missing_module_named_import.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_missing_module_named_import.ts b/tests/specs/run/error_missing_module_named_import/error_missing_module_named_import.ts
similarity index 100%
rename from tests/testdata/run/error_missing_module_named_import.ts
rename to tests/specs/run/error_missing_module_named_import/error_missing_module_named_import.ts
diff --git a/tests/testdata/run/error_missing_module_named_import.ts.out b/tests/specs/run/error_missing_module_named_import/error_missing_module_named_import.ts.out
similarity index 100%
rename from tests/testdata/run/error_missing_module_named_import.ts.out
rename to tests/specs/run/error_missing_module_named_import/error_missing_module_named_import.ts.out
diff --git a/tests/specs/run/error_name_non_string/__test__.jsonc b/tests/specs/run/error_name_non_string/__test__.jsonc
new file mode 100644
index 0000000000..a6748b56a2
--- /dev/null
+++ b/tests/specs/run/error_name_non_string/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet error_name_non_string.js",
+  "output": "error_name_non_string.js.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_name_non_string.js b/tests/specs/run/error_name_non_string/error_name_non_string.js
similarity index 100%
rename from tests/testdata/run/error_name_non_string.js
rename to tests/specs/run/error_name_non_string/error_name_non_string.js
diff --git a/tests/testdata/run/error_name_non_string.js.out b/tests/specs/run/error_name_non_string/error_name_non_string.js.out
similarity index 100%
rename from tests/testdata/run/error_name_non_string.js.out
rename to tests/specs/run/error_name_non_string/error_name_non_string.js.out
diff --git a/tests/specs/run/error_no_check/__test__.jsonc b/tests/specs/run/error_no_check/__test__.jsonc
new file mode 100644
index 0000000000..439dc5615d
--- /dev/null
+++ b/tests/specs/run/error_no_check/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload --no-check error_no_check.ts",
+  "output": "error_no_check.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/error_no_check/error_no_check.ts b/tests/specs/run/error_no_check/error_no_check.ts
new file mode 100644
index 0000000000..95ebff0282
--- /dev/null
+++ b/tests/specs/run/error_no_check/error_no_check.ts
@@ -0,0 +1 @@
+export { AnInterface, isAnInterface } from "./type_and_code.ts";
diff --git a/tests/specs/run/error_no_check/error_no_check.ts.out b/tests/specs/run/error_no_check/error_no_check.ts.out
new file mode 100644
index 0000000000..c4e85332d1
--- /dev/null
+++ b/tests/specs/run/error_no_check/error_no_check.ts.out
@@ -0,0 +1,2 @@
+error: Uncaught SyntaxError: The requested module './type_and_code.ts' does not provide an export named 'AnInterface'
+[WILDCARD]
\ No newline at end of file
diff --git a/tests/specs/run/error_no_check/type_and_code.ts b/tests/specs/run/error_no_check/type_and_code.ts
new file mode 100644
index 0000000000..b147134195
--- /dev/null
+++ b/tests/specs/run/error_no_check/type_and_code.ts
@@ -0,0 +1,7 @@
+export interface AnInterface {
+  a: string;
+}
+
+export function isAnInterface(value: unknown): value is AnInterface {
+  return value && typeof value === "object" && "a" in value;
+}
diff --git a/tests/specs/run/error_syntax/__test__.jsonc b/tests/specs/run/error_syntax/__test__.jsonc
new file mode 100644
index 0000000000..7a60f2c732
--- /dev/null
+++ b/tests/specs/run/error_syntax/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload error_syntax.js",
+  "output": "error_syntax.js.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_syntax.js b/tests/specs/run/error_syntax/error_syntax.js
similarity index 100%
rename from tests/testdata/run/error_syntax.js
rename to tests/specs/run/error_syntax/error_syntax.js
diff --git a/tests/testdata/run/error_syntax.js.out b/tests/specs/run/error_syntax/error_syntax.js.out
similarity index 100%
rename from tests/testdata/run/error_syntax.js.out
rename to tests/specs/run/error_syntax/error_syntax.js.out
diff --git a/tests/specs/run/error_syntax_empty_trailing_line/__test__.jsonc b/tests/specs/run/error_syntax_empty_trailing_line/__test__.jsonc
new file mode 100644
index 0000000000..72f1de1f7a
--- /dev/null
+++ b/tests/specs/run/error_syntax_empty_trailing_line/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload error_syntax_empty_trailing_line.mjs",
+  "output": "error_syntax_empty_trailing_line.mjs.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_syntax_empty_trailing_line.mjs b/tests/specs/run/error_syntax_empty_trailing_line/error_syntax_empty_trailing_line.mjs
similarity index 100%
rename from tests/testdata/run/error_syntax_empty_trailing_line.mjs
rename to tests/specs/run/error_syntax_empty_trailing_line/error_syntax_empty_trailing_line.mjs
diff --git a/tests/testdata/run/error_syntax_empty_trailing_line.mjs.out b/tests/specs/run/error_syntax_empty_trailing_line/error_syntax_empty_trailing_line.mjs.out
similarity index 100%
rename from tests/testdata/run/error_syntax_empty_trailing_line.mjs.out
rename to tests/specs/run/error_syntax_empty_trailing_line/error_syntax_empty_trailing_line.mjs.out
diff --git a/tests/specs/run/error_type_definitions/__test__.jsonc b/tests/specs/run/error_type_definitions/__test__.jsonc
new file mode 100644
index 0000000000..0ea9bc0164
--- /dev/null
+++ b/tests/specs/run/error_type_definitions/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload --check error_type_definitions.ts",
+  "output": "error_type_definitions.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/error_type_definitions/error_type_definitions.ts b/tests/specs/run/error_type_definitions/error_type_definitions.ts
new file mode 100644
index 0000000000..ceb11787e5
--- /dev/null
+++ b/tests/specs/run/error_type_definitions/error_type_definitions.ts
@@ -0,0 +1,5 @@
+// @deno-types="./type_definitions/bar.d.ts"
+import { Bar } from "./type_definitions/bar.js";
+
+const bar = new Bar();
+console.log(bar);
diff --git a/tests/testdata/run/error_type_definitions.ts.out b/tests/specs/run/error_type_definitions/error_type_definitions.ts.out
similarity index 100%
rename from tests/testdata/run/error_type_definitions.ts.out
rename to tests/specs/run/error_type_definitions/error_type_definitions.ts.out
diff --git a/tests/specs/run/error_type_definitions/type_definitions/bar.d.ts b/tests/specs/run/error_type_definitions/type_definitions/bar.d.ts
new file mode 100644
index 0000000000..d43335dbb5
--- /dev/null
+++ b/tests/specs/run/error_type_definitions/type_definitions/bar.d.ts
@@ -0,0 +1,7 @@
+/// <reference types="baz" />
+
+declare namespace bar {
+  export class Bar {
+    baz: string;
+  }
+}
diff --git a/tests/specs/run/error_type_definitions/type_definitions/bar.js b/tests/specs/run/error_type_definitions/type_definitions/bar.js
new file mode 100644
index 0000000000..e9c2e5193c
--- /dev/null
+++ b/tests/specs/run/error_type_definitions/type_definitions/bar.js
@@ -0,0 +1,5 @@
+export class Bar {
+  constructor() {
+    this.baz = "baz";
+  }
+}
diff --git a/tests/specs/run/error_type_definitions/type_definitions/fizz.d.ts b/tests/specs/run/error_type_definitions/type_definitions/fizz.d.ts
new file mode 100644
index 0000000000..34eb41b960
--- /dev/null
+++ b/tests/specs/run/error_type_definitions/type_definitions/fizz.d.ts
@@ -0,0 +1,2 @@
+/** A global value. */
+declare const fizz: string;
diff --git a/tests/specs/run/error_type_definitions/type_definitions/fizz.js b/tests/specs/run/error_type_definitions/type_definitions/fizz.js
new file mode 100644
index 0000000000..852162c940
--- /dev/null
+++ b/tests/specs/run/error_type_definitions/type_definitions/fizz.js
@@ -0,0 +1 @@
+globalThis.fizz = "fizz";
diff --git a/tests/specs/run/error_type_definitions/type_definitions/foo.d.ts b/tests/specs/run/error_type_definitions/type_definitions/foo.d.ts
new file mode 100644
index 0000000000..ce39201e1b
--- /dev/null
+++ b/tests/specs/run/error_type_definitions/type_definitions/foo.d.ts
@@ -0,0 +1,2 @@
+/** An exported value. */
+export const foo: string;
diff --git a/tests/specs/run/error_type_definitions/type_definitions/foo.js b/tests/specs/run/error_type_definitions/type_definitions/foo.js
new file mode 100644
index 0000000000..61d366eb25
--- /dev/null
+++ b/tests/specs/run/error_type_definitions/type_definitions/foo.js
@@ -0,0 +1 @@
+export const foo = "foo";
diff --git a/tests/specs/run/error_type_definitions/type_definitions/qat.ts b/tests/specs/run/error_type_definitions/type_definitions/qat.ts
new file mode 100644
index 0000000000..6196c9d387
--- /dev/null
+++ b/tests/specs/run/error_type_definitions/type_definitions/qat.ts
@@ -0,0 +1 @@
+export const qat = "qat";
diff --git a/tests/specs/run/error_with_errors_prop/__test__.jsonc b/tests/specs/run/error_with_errors_prop/__test__.jsonc
new file mode 100644
index 0000000000..afbfd24cfe
--- /dev/null
+++ b/tests/specs/run/error_with_errors_prop/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet error_with_errors_prop.js",
+  "output": "error_with_errors_prop.js.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/error_with_errors_prop.js b/tests/specs/run/error_with_errors_prop/error_with_errors_prop.js
similarity index 100%
rename from tests/testdata/run/error_with_errors_prop.js
rename to tests/specs/run/error_with_errors_prop/error_with_errors_prop.js
diff --git a/tests/testdata/run/error_with_errors_prop.js.out b/tests/specs/run/error_with_errors_prop/error_with_errors_prop.js.out
similarity index 100%
rename from tests/testdata/run/error_with_errors_prop.js.out
rename to tests/specs/run/error_with_errors_prop/error_with_errors_prop.js.out
diff --git a/tests/specs/run/es_private_fields/__test__.jsonc b/tests/specs/run/es_private_fields/__test__.jsonc
new file mode 100644
index 0000000000..817efd67e3
--- /dev/null
+++ b/tests/specs/run/es_private_fields/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload es_private_fields.js",
+  "output": "es_private_fields.js.out"
+}
diff --git a/tests/testdata/run/es_private_fields.js b/tests/specs/run/es_private_fields/es_private_fields.js
similarity index 100%
rename from tests/testdata/run/es_private_fields.js
rename to tests/specs/run/es_private_fields/es_private_fields.js
diff --git a/tests/testdata/run/es_private_fields.js.out b/tests/specs/run/es_private_fields/es_private_fields.js.out
similarity index 100%
rename from tests/testdata/run/es_private_fields.js.out
rename to tests/specs/run/es_private_fields/es_private_fields.js.out
diff --git a/tests/specs/run/eval_context_throw_dom_exception/__test__.jsonc b/tests/specs/run/eval_context_throw_dom_exception/__test__.jsonc
new file mode 100644
index 0000000000..6ad302b03a
--- /dev/null
+++ b/tests/specs/run/eval_context_throw_dom_exception/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run eval_context_throw_dom_exception.js",
+  "output": "eval_context_throw_dom_exception.js.out"
+}
diff --git a/tests/testdata/run/eval_context_throw_dom_exception.js b/tests/specs/run/eval_context_throw_dom_exception/eval_context_throw_dom_exception.js
similarity index 100%
rename from tests/testdata/run/eval_context_throw_dom_exception.js
rename to tests/specs/run/eval_context_throw_dom_exception/eval_context_throw_dom_exception.js
diff --git a/tests/testdata/run/eval_context_throw_dom_exception.js.out b/tests/specs/run/eval_context_throw_dom_exception/eval_context_throw_dom_exception.js.out
similarity index 100%
rename from tests/testdata/run/eval_context_throw_dom_exception.js.out
rename to tests/specs/run/eval_context_throw_dom_exception/eval_context_throw_dom_exception.js.out
diff --git a/tests/specs/run/event_listener_error/__test__.jsonc b/tests/specs/run/event_listener_error/__test__.jsonc
new file mode 100644
index 0000000000..b2540e03dc
--- /dev/null
+++ b/tests/specs/run/event_listener_error/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet event_listener_error.ts",
+  "output": "event_listener_error.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/event_listener_error.ts b/tests/specs/run/event_listener_error/event_listener_error.ts
similarity index 100%
rename from tests/testdata/run/event_listener_error.ts
rename to tests/specs/run/event_listener_error/event_listener_error.ts
diff --git a/tests/testdata/run/event_listener_error.ts.out b/tests/specs/run/event_listener_error/event_listener_error.ts.out
similarity index 100%
rename from tests/testdata/run/event_listener_error.ts.out
rename to tests/specs/run/event_listener_error/event_listener_error.ts.out
diff --git a/tests/specs/run/event_listener_error_handled/__test__.jsonc b/tests/specs/run/event_listener_error_handled/__test__.jsonc
new file mode 100644
index 0000000000..f1fdcd5dba
--- /dev/null
+++ b/tests/specs/run/event_listener_error_handled/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet event_listener_error_handled.ts",
+  "output": "event_listener_error_handled.ts.out"
+}
diff --git a/tests/testdata/run/event_listener_error_handled.ts b/tests/specs/run/event_listener_error_handled/event_listener_error_handled.ts
similarity index 100%
rename from tests/testdata/run/event_listener_error_handled.ts
rename to tests/specs/run/event_listener_error_handled/event_listener_error_handled.ts
diff --git a/tests/testdata/run/event_listener_error_handled.ts.out b/tests/specs/run/event_listener_error_handled/event_listener_error_handled.ts.out
similarity index 100%
rename from tests/testdata/run/event_listener_error_handled.ts.out
rename to tests/specs/run/event_listener_error_handled/event_listener_error_handled.ts.out
diff --git a/tests/specs/run/event_listener_error_immediate_exit/__test__.jsonc b/tests/specs/run/event_listener_error_immediate_exit/__test__.jsonc
new file mode 100644
index 0000000000..2974c0e422
--- /dev/null
+++ b/tests/specs/run/event_listener_error_immediate_exit/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet event_listener_error_immediate_exit.ts",
+  "output": "event_listener_error_immediate_exit.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/event_listener_error_immediate_exit.ts b/tests/specs/run/event_listener_error_immediate_exit/event_listener_error_immediate_exit.ts
similarity index 100%
rename from tests/testdata/run/event_listener_error_immediate_exit.ts
rename to tests/specs/run/event_listener_error_immediate_exit/event_listener_error_immediate_exit.ts
diff --git a/tests/testdata/run/event_listener_error_immediate_exit.ts.out b/tests/specs/run/event_listener_error_immediate_exit/event_listener_error_immediate_exit.ts.out
similarity index 100%
rename from tests/testdata/run/event_listener_error_immediate_exit.ts.out
rename to tests/specs/run/event_listener_error_immediate_exit/event_listener_error_immediate_exit.ts.out
diff --git a/tests/specs/run/event_listener_error_immediate_exit_worker/__test__.jsonc b/tests/specs/run/event_listener_error_immediate_exit_worker/__test__.jsonc
new file mode 100644
index 0000000000..6ef3ef2ed1
--- /dev/null
+++ b/tests/specs/run/event_listener_error_immediate_exit_worker/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet -A event_listener_error_immediate_exit_worker.ts",
+  "output": "event_listener_error_immediate_exit_worker.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/event_listener_error_immediate_exit_worker/event_listener_error_immediate_exit.ts b/tests/specs/run/event_listener_error_immediate_exit_worker/event_listener_error_immediate_exit.ts
new file mode 100644
index 0000000000..292a0df007
--- /dev/null
+++ b/tests/specs/run/event_listener_error_immediate_exit_worker/event_listener_error_immediate_exit.ts
@@ -0,0 +1,12 @@
+addEventListener("foo", () => {
+  queueMicrotask(() => console.log("queueMicrotask"));
+  setTimeout(() => console.log("timer"), 0);
+  throw new Error("bar");
+});
+console.log(1);
+// @ts-ignore Deno[Deno.internal].core
+Deno[Deno.internal].core.setNextTickCallback(() => console.log("nextTick"));
+// @ts-ignore Deno[Deno.internal].core
+Deno[Deno.internal].core.setHasTickScheduled(true);
+dispatchEvent(new CustomEvent("foo"));
+console.log(2);
diff --git a/tests/testdata/run/event_listener_error_immediate_exit_worker.ts b/tests/specs/run/event_listener_error_immediate_exit_worker/event_listener_error_immediate_exit_worker.ts
similarity index 100%
rename from tests/testdata/run/event_listener_error_immediate_exit_worker.ts
rename to tests/specs/run/event_listener_error_immediate_exit_worker/event_listener_error_immediate_exit_worker.ts
diff --git a/tests/testdata/run/event_listener_error_immediate_exit_worker.ts.out b/tests/specs/run/event_listener_error_immediate_exit_worker/event_listener_error_immediate_exit_worker.ts.out
similarity index 100%
rename from tests/testdata/run/event_listener_error_immediate_exit_worker.ts.out
rename to tests/specs/run/event_listener_error_immediate_exit_worker/event_listener_error_immediate_exit_worker.ts.out
diff --git a/tests/specs/run/exit_error42/__test__.jsonc b/tests/specs/run/exit_error42/__test__.jsonc
new file mode 100644
index 0000000000..43d3089566
--- /dev/null
+++ b/tests/specs/run/exit_error42/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --reload exit_error42.ts",
+  "output": "exit_error42.ts.out",
+  "exitCode": 42
+}
diff --git a/tests/testdata/run/exit_error42.ts b/tests/specs/run/exit_error42/exit_error42.ts
similarity index 100%
rename from tests/testdata/run/exit_error42.ts
rename to tests/specs/run/exit_error42/exit_error42.ts
diff --git a/tests/testdata/run/exit_error42.ts.out b/tests/specs/run/exit_error42/exit_error42.ts.out
similarity index 100%
rename from tests/testdata/run/exit_error42.ts.out
rename to tests/specs/run/exit_error42/exit_error42.ts.out
diff --git a/tests/specs/run/explicit_resource_management/__test__.jsonc b/tests/specs/run/explicit_resource_management/__test__.jsonc
new file mode 100644
index 0000000000..7062e6f36f
--- /dev/null
+++ b/tests/specs/run/explicit_resource_management/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --check explicit_resource_management/main.ts",
+  "output": "explicit_resource_management/main.out"
+}
diff --git a/tests/testdata/run/explicit_resource_management/main.out b/tests/specs/run/explicit_resource_management/explicit_resource_management/main.out
similarity index 100%
rename from tests/testdata/run/explicit_resource_management/main.out
rename to tests/specs/run/explicit_resource_management/explicit_resource_management/main.out
diff --git a/tests/testdata/run/explicit_resource_management/main.ts b/tests/specs/run/explicit_resource_management/explicit_resource_management/main.ts
similarity index 100%
rename from tests/testdata/run/explicit_resource_management/main.ts
rename to tests/specs/run/explicit_resource_management/explicit_resource_management/main.ts
diff --git a/tests/specs/run/ext_flag_takes_precedence_over_extension/__test__.jsonc b/tests/specs/run/ext_flag_takes_precedence_over_extension/__test__.jsonc
new file mode 100644
index 0000000000..0806088b4e
--- /dev/null
+++ b/tests/specs/run/ext_flag_takes_precedence_over_extension/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --ext ts --check ts_with_js_extension.js",
+  "output": "ts_with_js_extension.out",
+  "exitCode": 0
+}
diff --git a/tests/specs/run/ext_flag_takes_precedence_over_extension/ts_with_js_extension.js b/tests/specs/run/ext_flag_takes_precedence_over_extension/ts_with_js_extension.js
new file mode 100644
index 0000000000..3c49f74846
--- /dev/null
+++ b/tests/specs/run/ext_flag_takes_precedence_over_extension/ts_with_js_extension.js
@@ -0,0 +1,5 @@
+interface Lollipop {
+  _: number;
+}
+
+console.log("executing typescript with extension");
diff --git a/tests/specs/run/ext_flag_takes_precedence_over_extension/ts_with_js_extension.out b/tests/specs/run/ext_flag_takes_precedence_over_extension/ts_with_js_extension.out
new file mode 100644
index 0000000000..7ae7b9168f
--- /dev/null
+++ b/tests/specs/run/ext_flag_takes_precedence_over_extension/ts_with_js_extension.out
@@ -0,0 +1,2 @@
+Check [WILDCARD]/ts_with_js_extension.js
+executing typescript with extension
diff --git a/tests/specs/run/fetch_async_error_stack/__test__.jsonc b/tests/specs/run/fetch_async_error_stack/__test__.jsonc
new file mode 100644
index 0000000000..152f57807c
--- /dev/null
+++ b/tests/specs/run/fetch_async_error_stack/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet -A fetch_async_error_stack.ts",
+  "output": "fetch_async_error_stack.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/fetch_async_error_stack.ts b/tests/specs/run/fetch_async_error_stack/fetch_async_error_stack.ts
similarity index 100%
rename from tests/testdata/run/fetch_async_error_stack.ts
rename to tests/specs/run/fetch_async_error_stack/fetch_async_error_stack.ts
diff --git a/tests/testdata/run/fetch_async_error_stack.ts.out b/tests/specs/run/fetch_async_error_stack/fetch_async_error_stack.ts.out
similarity index 100%
rename from tests/testdata/run/fetch_async_error_stack.ts.out
rename to tests/specs/run/fetch_async_error_stack/fetch_async_error_stack.ts.out
diff --git a/tests/specs/run/fetch_response_finalization/__test__.jsonc b/tests/specs/run/fetch_response_finalization/__test__.jsonc
new file mode 100644
index 0000000000..51a7e2b045
--- /dev/null
+++ b/tests/specs/run/fetch_response_finalization/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --v8-flags=--expose-gc --allow-net fetch_response_finalization.js",
+  "output": "fetch_response_finalization.js.out",
+  "exitCode": 0
+}
diff --git a/tests/testdata/run/fetch_response_finalization.js b/tests/specs/run/fetch_response_finalization/fetch_response_finalization.js
similarity index 100%
rename from tests/testdata/run/fetch_response_finalization.js
rename to tests/specs/run/fetch_response_finalization/fetch_response_finalization.js
diff --git a/tests/testdata/run/fetch_response_finalization.js.out b/tests/specs/run/fetch_response_finalization/fetch_response_finalization.js.out
similarity index 100%
rename from tests/testdata/run/fetch_response_finalization.js.out
rename to tests/specs/run/fetch_response_finalization/fetch_response_finalization.js.out
diff --git a/tests/specs/run/finalization_registry/__test__.jsonc b/tests/specs/run/finalization_registry/__test__.jsonc
new file mode 100644
index 0000000000..f7526506c5
--- /dev/null
+++ b/tests/specs/run/finalization_registry/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --v8-flags=--expose-gc finalization_registry.js",
+  "output": "finalization_registry.js.out"
+}
diff --git a/tests/testdata/run/finalization_registry.js b/tests/specs/run/finalization_registry/finalization_registry.js
similarity index 100%
rename from tests/testdata/run/finalization_registry.js
rename to tests/specs/run/finalization_registry/finalization_registry.js
diff --git a/tests/testdata/run/finalization_registry.js.out b/tests/specs/run/finalization_registry/finalization_registry.js.out
similarity index 100%
rename from tests/testdata/run/finalization_registry.js.out
rename to tests/specs/run/finalization_registry/finalization_registry.js.out
diff --git a/tests/specs/run/fix_dynamic_import_errors/__test__.jsonc b/tests/specs/run/fix_dynamic_import_errors/__test__.jsonc
new file mode 100644
index 0000000000..d9302d2cae
--- /dev/null
+++ b/tests/specs/run/fix_dynamic_import_errors/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload fix_dynamic_import_errors.js",
+  "output": "fix_dynamic_import_errors.js.out"
+}
diff --git a/tests/specs/run/fix_dynamic_import_errors/b.js b/tests/specs/run/fix_dynamic_import_errors/b.js
new file mode 100644
index 0000000000..6ea50d3608
--- /dev/null
+++ b/tests/specs/run/fix_dynamic_import_errors/b.js
@@ -0,0 +1,2 @@
+import "./bad.mjs";
+export default () => "error";
diff --git a/tests/specs/run/fix_dynamic_import_errors/c.js b/tests/specs/run/fix_dynamic_import_errors/c.js
new file mode 100644
index 0000000000..20546455ea
--- /dev/null
+++ b/tests/specs/run/fix_dynamic_import_errors/c.js
@@ -0,0 +1,2 @@
+await import("./bad2.mjs");
+export default () => "error";
diff --git a/tests/testdata/run/fix_dynamic_import_errors.js b/tests/specs/run/fix_dynamic_import_errors/fix_dynamic_import_errors.js
similarity index 52%
rename from tests/testdata/run/fix_dynamic_import_errors.js
rename to tests/specs/run/fix_dynamic_import_errors/fix_dynamic_import_errors.js
index 1d7be37e06..e105cbada6 100644
--- a/tests/testdata/run/fix_dynamic_import_errors.js
+++ b/tests/specs/run/fix_dynamic_import_errors/fix_dynamic_import_errors.js
@@ -1,7 +1,7 @@
-import("../dynamic_import/b.js").catch(() => {
+import("./b.js").catch(() => {
   console.log("caught import error from b.js");
 });
 
-import("../dynamic_import/c.js").catch(() => {
+import("./c.js").catch(() => {
   console.log("caught import error from c.js");
 });
diff --git a/tests/testdata/run/fix_dynamic_import_errors.js.out b/tests/specs/run/fix_dynamic_import_errors/fix_dynamic_import_errors.js.out
similarity index 100%
rename from tests/testdata/run/fix_dynamic_import_errors.js.out
rename to tests/specs/run/fix_dynamic_import_errors/fix_dynamic_import_errors.js.out
diff --git a/tests/specs/run/fix_emittable_skipped/__test__.jsonc b/tests/specs/run/fix_emittable_skipped/__test__.jsonc
new file mode 100644
index 0000000000..ef1445e0e3
--- /dev/null
+++ b/tests/specs/run/fix_emittable_skipped/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload fix_emittable_skipped.js",
+  "output": "fix_emittable_skipped.ts.out"
+}
diff --git a/tests/specs/run/fix_emittable_skipped/emittable.d.ts b/tests/specs/run/fix_emittable_skipped/emittable.d.ts
new file mode 100644
index 0000000000..425b80f244
--- /dev/null
+++ b/tests/specs/run/fix_emittable_skipped/emittable.d.ts
@@ -0,0 +1 @@
+export const a: string;
diff --git a/tests/specs/run/fix_emittable_skipped/fix_emittable_skipped.js b/tests/specs/run/fix_emittable_skipped/fix_emittable_skipped.js
new file mode 100644
index 0000000000..b94af2730f
--- /dev/null
+++ b/tests/specs/run/fix_emittable_skipped/fix_emittable_skipped.js
@@ -0,0 +1,7 @@
+/// <reference types="./emittable.d.ts" />
+
+import "./polyfill.ts";
+
+export const a = "a";
+
+console.log(globalThis.polyfill);
diff --git a/tests/testdata/run/fix_emittable_skipped.ts.out b/tests/specs/run/fix_emittable_skipped/fix_emittable_skipped.ts.out
similarity index 100%
rename from tests/testdata/run/fix_emittable_skipped.ts.out
rename to tests/specs/run/fix_emittable_skipped/fix_emittable_skipped.ts.out
diff --git a/tests/specs/run/fix_emittable_skipped/polyfill.ts b/tests/specs/run/fix_emittable_skipped/polyfill.ts
new file mode 100644
index 0000000000..7af67c4c03
--- /dev/null
+++ b/tests/specs/run/fix_emittable_skipped/polyfill.ts
@@ -0,0 +1,8 @@
+declare global {
+  const polyfill: () => void;
+}
+
+// deno-lint-ignore no-explicit-any
+(globalThis as any).polyfill = () => {
+  console.log("polyfill");
+};
diff --git a/tests/specs/run/fix_js_import_js/__test__.jsonc b/tests/specs/run/fix_js_import_js/__test__.jsonc
new file mode 100644
index 0000000000..94b1df540a
--- /dev/null
+++ b/tests/specs/run/fix_js_import_js/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload fix_js_import_js.ts",
+  "output": "fix_js_import_js.ts.out"
+}
diff --git a/tests/specs/run/fix_js_import_js/fix_js_import_js.ts b/tests/specs/run/fix_js_import_js/fix_js_import_js.ts
new file mode 100644
index 0000000000..4862f03e10
--- /dev/null
+++ b/tests/specs/run/fix_js_import_js/fix_js_import_js.ts
@@ -0,0 +1,3 @@
+import { isMod4 } from "./mod6.js";
+
+console.log(isMod4);
diff --git a/tests/testdata/run/fix_js_import_js.ts.out b/tests/specs/run/fix_js_import_js/fix_js_import_js.ts.out
similarity index 100%
rename from tests/testdata/run/fix_js_import_js.ts.out
rename to tests/specs/run/fix_js_import_js/fix_js_import_js.ts.out
diff --git a/tests/specs/run/fix_js_import_js/mod4.js b/tests/specs/run/fix_js_import_js/mod4.js
new file mode 100644
index 0000000000..71332dbc42
--- /dev/null
+++ b/tests/specs/run/fix_js_import_js/mod4.js
@@ -0,0 +1 @@
+export const isMod4 = true;
diff --git a/tests/specs/run/fix_js_import_js/mod6.js b/tests/specs/run/fix_js_import_js/mod6.js
new file mode 100644
index 0000000000..5e17c9ee02
--- /dev/null
+++ b/tests/specs/run/fix_js_import_js/mod6.js
@@ -0,0 +1 @@
+export { isMod4 } from "./mod4.js";
diff --git a/tests/specs/run/fix_js_imports/__test__.jsonc b/tests/specs/run/fix_js_imports/__test__.jsonc
new file mode 100644
index 0000000000..a3635d18c9
--- /dev/null
+++ b/tests/specs/run/fix_js_imports/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload fix_js_imports.ts",
+  "output": "fix_js_imports.ts.out"
+}
diff --git a/tests/specs/run/fix_js_imports/amd_like.js b/tests/specs/run/fix_js_imports/amd_like.js
new file mode 100644
index 0000000000..f27e505e4a
--- /dev/null
+++ b/tests/specs/run/fix_js_imports/amd_like.js
@@ -0,0 +1,3 @@
+// looks like an AMD module, but isn't
+const define = () => {};
+define(["fake_module"], () => {});
diff --git a/tests/specs/run/fix_js_imports/fix_js_imports.ts b/tests/specs/run/fix_js_imports/fix_js_imports.ts
new file mode 100644
index 0000000000..07e68a1356
--- /dev/null
+++ b/tests/specs/run/fix_js_imports/fix_js_imports.ts
@@ -0,0 +1,3 @@
+import * as amdLike from "./amd_like.js";
+
+console.log(amdLike);
diff --git a/tests/testdata/run/fix_js_imports.ts.out b/tests/specs/run/fix_js_imports/fix_js_imports.ts.out
similarity index 100%
rename from tests/testdata/run/fix_js_imports.ts.out
rename to tests/specs/run/fix_js_imports/fix_js_imports.ts.out
diff --git a/tests/specs/run/fix_tsc_file_exists/__test__.jsonc b/tests/specs/run/fix_tsc_file_exists/__test__.jsonc
new file mode 100644
index 0000000000..d2b0bda29f
--- /dev/null
+++ b/tests/specs/run/fix_tsc_file_exists/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload tsc/test.js",
+  "output": "fix_tsc_file_exists.out"
+}
diff --git a/tests/testdata/run/fix_tsc_file_exists.out b/tests/specs/run/fix_tsc_file_exists/fix_tsc_file_exists.out
similarity index 100%
rename from tests/testdata/run/fix_tsc_file_exists.out
rename to tests/specs/run/fix_tsc_file_exists/fix_tsc_file_exists.out
diff --git a/tests/specs/run/fix_tsc_file_exists/tsc/a.js b/tests/specs/run/fix_tsc_file_exists/tsc/a.js
new file mode 100644
index 0000000000..5a7b3ff93c
--- /dev/null
+++ b/tests/specs/run/fix_tsc_file_exists/tsc/a.js
@@ -0,0 +1,2 @@
+import { v4 } from "./d.ts";
+export function a() {}
diff --git a/tests/specs/run/fix_tsc_file_exists/tsc/d.ts b/tests/specs/run/fix_tsc_file_exists/tsc/d.ts
new file mode 100644
index 0000000000..3c74b8c836
--- /dev/null
+++ b/tests/specs/run/fix_tsc_file_exists/tsc/d.ts
@@ -0,0 +1,3 @@
+export function v4() {
+  return "hello";
+}
diff --git a/tests/specs/run/fix_tsc_file_exists/tsc/node_modules/b.js b/tests/specs/run/fix_tsc_file_exists/tsc/node_modules/b.js
new file mode 100644
index 0000000000..1916609355
--- /dev/null
+++ b/tests/specs/run/fix_tsc_file_exists/tsc/node_modules/b.js
@@ -0,0 +1,2 @@
+import c from "./c.js";
+export { c };
diff --git a/tests/specs/run/fix_tsc_file_exists/tsc/node_modules/c.js b/tests/specs/run/fix_tsc_file_exists/tsc/node_modules/c.js
new file mode 100644
index 0000000000..cff71c44a0
--- /dev/null
+++ b/tests/specs/run/fix_tsc_file_exists/tsc/node_modules/c.js
@@ -0,0 +1 @@
+export default function c() {}
diff --git a/tests/specs/run/fix_tsc_file_exists/tsc/test.js b/tests/specs/run/fix_tsc_file_exists/tsc/test.js
new file mode 100644
index 0000000000..b7f46b351f
--- /dev/null
+++ b/tests/specs/run/fix_tsc_file_exists/tsc/test.js
@@ -0,0 +1,4 @@
+import { a } from "./a.js";
+import { c } from "./node_modules/b.js";
+
+console.log("hello");
diff --git a/tests/specs/run/fix_worker_dispatchevent/__test__.jsonc b/tests/specs/run/fix_worker_dispatchevent/__test__.jsonc
new file mode 100644
index 0000000000..45e49b87f9
--- /dev/null
+++ b/tests/specs/run/fix_worker_dispatchevent/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload fix_worker_dispatchevent.ts",
+  "output": "fix_worker_dispatchevent.ts.out"
+}
diff --git a/tests/testdata/run/fix_worker_dispatchevent.ts b/tests/specs/run/fix_worker_dispatchevent/fix_worker_dispatchevent.ts
similarity index 100%
rename from tests/testdata/run/fix_worker_dispatchevent.ts
rename to tests/specs/run/fix_worker_dispatchevent/fix_worker_dispatchevent.ts
diff --git a/tests/testdata/run/fix_worker_dispatchevent.ts.out b/tests/specs/run/fix_worker_dispatchevent/fix_worker_dispatchevent.ts.out
similarity index 100%
rename from tests/testdata/run/fix_worker_dispatchevent.ts.out
rename to tests/specs/run/fix_worker_dispatchevent/fix_worker_dispatchevent.ts.out
diff --git a/tests/specs/run/followup_dyn_import_resolved/__test__.jsonc b/tests/specs/run/followup_dyn_import_resolved/__test__.jsonc
new file mode 100644
index 0000000000..b94e3d8c91
--- /dev/null
+++ b/tests/specs/run/followup_dyn_import_resolved/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read followup_dyn_import_resolves/main.ts",
+  "output": "followup_dyn_import_resolves/main.ts.out"
+}
diff --git a/tests/testdata/run/followup_dyn_import_resolves/main.ts b/tests/specs/run/followup_dyn_import_resolved/followup_dyn_import_resolves/main.ts
similarity index 100%
rename from tests/testdata/run/followup_dyn_import_resolves/main.ts
rename to tests/specs/run/followup_dyn_import_resolved/followup_dyn_import_resolves/main.ts
diff --git a/tests/testdata/run/followup_dyn_import_resolves/main.ts.out b/tests/specs/run/followup_dyn_import_resolved/followup_dyn_import_resolves/main.ts.out
similarity index 100%
rename from tests/testdata/run/followup_dyn_import_resolves/main.ts.out
rename to tests/specs/run/followup_dyn_import_resolved/followup_dyn_import_resolves/main.ts.out
diff --git a/tests/specs/run/followup_dyn_import_resolved/followup_dyn_import_resolves/sub1.ts b/tests/specs/run/followup_dyn_import_resolved/followup_dyn_import_resolves/sub1.ts
new file mode 100644
index 0000000000..d06c30221b
--- /dev/null
+++ b/tests/specs/run/followup_dyn_import_resolved/followup_dyn_import_resolves/sub1.ts
@@ -0,0 +1,2 @@
+await import("./sub2.ts");
+console.log("sub1");
diff --git a/tests/specs/run/followup_dyn_import_resolved/followup_dyn_import_resolves/sub2.ts b/tests/specs/run/followup_dyn_import_resolved/followup_dyn_import_resolves/sub2.ts
new file mode 100644
index 0000000000..cce2b524cd
--- /dev/null
+++ b/tests/specs/run/followup_dyn_import_resolved/followup_dyn_import_resolves/sub2.ts
@@ -0,0 +1 @@
+console.log("sub2");
diff --git a/tests/specs/run/heapstats/__test__.jsonc b/tests/specs/run/heapstats/__test__.jsonc
new file mode 100644
index 0000000000..6429d7cf5f
--- /dev/null
+++ b/tests/specs/run/heapstats/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --v8-flags=--expose-gc heapstats.js",
+  "output": "heapstats.js.out"
+}
diff --git a/tests/testdata/run/heapstats.js b/tests/specs/run/heapstats/heapstats.js
similarity index 100%
rename from tests/testdata/run/heapstats.js
rename to tests/specs/run/heapstats/heapstats.js
diff --git a/tests/testdata/run/heapstats.js.out b/tests/specs/run/heapstats/heapstats.js.out
similarity index 100%
rename from tests/testdata/run/heapstats.js.out
rename to tests/specs/run/heapstats/heapstats.js.out
diff --git a/tests/specs/run/https_import/RootCA.pem b/tests/specs/run/https_import/RootCA.pem
new file mode 100644
index 0000000000..c2f84ceebc
--- /dev/null
+++ b/tests/specs/run/https_import/RootCA.pem
@@ -0,0 +1,19 @@
+-----BEGIN CERTIFICATE-----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+-----END CERTIFICATE-----
diff --git a/tests/specs/run/https_import/__test__.jsonc b/tests/specs/run/https_import/__test__.jsonc
new file mode 100644
index 0000000000..9a37230f27
--- /dev/null
+++ b/tests/specs/run/https_import/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --quiet --reload --cert RootCA.pem https_import.ts",
+  "output": "https_import.ts.out"
+}
diff --git a/tests/specs/run/https_import/https_import.ts b/tests/specs/run/https_import/https_import.ts
new file mode 100644
index 0000000000..d392f4a5d1
--- /dev/null
+++ b/tests/specs/run/https_import/https_import.ts
@@ -0,0 +1,3 @@
+import { printHello } from "./print_hello.ts";
+
+printHello();
diff --git a/tests/specs/run/https_import/https_import.ts.out b/tests/specs/run/https_import/https_import.ts.out
new file mode 100644
index 0000000000..e965047ad7
--- /dev/null
+++ b/tests/specs/run/https_import/https_import.ts.out
@@ -0,0 +1 @@
+Hello
diff --git a/tests/specs/run/https_import/print_hello.ts b/tests/specs/run/https_import/print_hello.ts
new file mode 100644
index 0000000000..b9c0ad5275
--- /dev/null
+++ b/tests/specs/run/https_import/print_hello.ts
@@ -0,0 +1,3 @@
+export function printHello() {
+  console.log("Hello");
+}
diff --git a/tests/specs/run/if_main/__test__.jsonc b/tests/specs/run/if_main/__test__.jsonc
new file mode 100644
index 0000000000..f6e2dbf273
--- /dev/null
+++ b/tests/specs/run/if_main/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload if_main.ts",
+  "output": "if_main.ts.out"
+}
diff --git a/tests/testdata/run/if_main.ts b/tests/specs/run/if_main/if_main.ts
similarity index 100%
rename from tests/testdata/run/if_main.ts
rename to tests/specs/run/if_main/if_main.ts
diff --git a/tests/specs/run/if_main/if_main.ts.out b/tests/specs/run/if_main/if_main.ts.out
new file mode 100644
index 0000000000..ba2906d066
--- /dev/null
+++ b/tests/specs/run/if_main/if_main.ts.out
@@ -0,0 +1 @@
+main
diff --git a/tests/specs/run/import_attributes_dynamic_error/__test__.jsonc b/tests/specs/run/import_attributes_dynamic_error/__test__.jsonc
new file mode 100644
index 0000000000..0a6137a2b5
--- /dev/null
+++ b/tests/specs/run/import_attributes_dynamic_error/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --allow-read dynamic_error.ts",
+  "output": "dynamic_error.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/import_attributes_dynamic_error/data.json b/tests/specs/run/import_attributes_dynamic_error/data.json
new file mode 100644
index 0000000000..37b3ee1e0a
--- /dev/null
+++ b/tests/specs/run/import_attributes_dynamic_error/data.json
@@ -0,0 +1,6 @@
+{
+  "a": "b",
+  "c": {
+    "d": 10
+  }
+}
diff --git a/tests/specs/run/import_attributes_dynamic_error/dynamic_error.out b/tests/specs/run/import_attributes_dynamic_error/dynamic_error.out
new file mode 100644
index 0000000000..24f29de72d
--- /dev/null
+++ b/tests/specs/run/import_attributes_dynamic_error/dynamic_error.out
@@ -0,0 +1,4 @@
+error: Uncaught (in promise) TypeError: Attempted to load JSON module without specifying "type": "json" attribute in the import statement.
+const data = await import("./data.json");
+             ^
+    at async [WILDCARD]dynamic_error.ts:1:14
diff --git a/tests/specs/run/import_attributes_dynamic_error/dynamic_error.ts b/tests/specs/run/import_attributes_dynamic_error/dynamic_error.ts
new file mode 100644
index 0000000000..2d9c6757f6
--- /dev/null
+++ b/tests/specs/run/import_attributes_dynamic_error/dynamic_error.ts
@@ -0,0 +1,3 @@
+const data = await import("./data.json");
+
+console.log(data);
diff --git a/tests/specs/run/import_attributes_dynamic_import/__test__.jsonc b/tests/specs/run/import_attributes_dynamic_import/__test__.jsonc
new file mode 100644
index 0000000000..75962e88db
--- /dev/null
+++ b/tests/specs/run/import_attributes_dynamic_import/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read --check dynamic_import.ts",
+  "output": "dynamic_import.out"
+}
diff --git a/tests/specs/run/import_attributes_dynamic_import/data.json b/tests/specs/run/import_attributes_dynamic_import/data.json
new file mode 100644
index 0000000000..37b3ee1e0a
--- /dev/null
+++ b/tests/specs/run/import_attributes_dynamic_import/data.json
@@ -0,0 +1,6 @@
+{
+  "a": "b",
+  "c": {
+    "d": 10
+  }
+}
diff --git a/tests/specs/run/import_attributes_dynamic_import/dynamic_import.out b/tests/specs/run/import_attributes_dynamic_import/dynamic_import.out
new file mode 100644
index 0000000000..7a7b4c91fe
--- /dev/null
+++ b/tests/specs/run/import_attributes_dynamic_import/dynamic_import.out
@@ -0,0 +1,2 @@
+[WILDCARD]
+[Module: null prototype] { default: { a: "b", c: { d: 10 } } }
diff --git a/tests/specs/run/import_attributes_dynamic_import/dynamic_import.ts b/tests/specs/run/import_attributes_dynamic_import/dynamic_import.ts
new file mode 100644
index 0000000000..093136fb07
--- /dev/null
+++ b/tests/specs/run/import_attributes_dynamic_import/dynamic_import.ts
@@ -0,0 +1,3 @@
+const data1 = await import("./data.json", { with: { type: "json" } });
+
+console.log(data1);
diff --git a/tests/specs/run/import_attributes_static_error/__test__.jsonc b/tests/specs/run/import_attributes_static_error/__test__.jsonc
new file mode 100644
index 0000000000..2d08c66d35
--- /dev/null
+++ b/tests/specs/run/import_attributes_static_error/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --allow-read static_error.ts",
+  "output": "static_error.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/import_attributes_static_error/data.json b/tests/specs/run/import_attributes_static_error/data.json
new file mode 100644
index 0000000000..37b3ee1e0a
--- /dev/null
+++ b/tests/specs/run/import_attributes_static_error/data.json
@@ -0,0 +1,6 @@
+{
+  "a": "b",
+  "c": {
+    "d": 10
+  }
+}
diff --git a/tests/specs/run/import_attributes_static_error/static_error.out b/tests/specs/run/import_attributes_static_error/static_error.out
new file mode 100644
index 0000000000..29b24b965a
--- /dev/null
+++ b/tests/specs/run/import_attributes_static_error/static_error.out
@@ -0,0 +1,3 @@
+error: Expected a JavaScript or TypeScript module, but identified a Json module. Consider importing Json modules with an import attribute with the type of "json".
+  Specifier: [WILDCARD]/data.json
+    at [WILDCARD]static_error.ts:1:18
diff --git a/tests/specs/run/import_attributes_static_error/static_error.ts b/tests/specs/run/import_attributes_static_error/static_error.ts
new file mode 100644
index 0000000000..0bc3a93f88
--- /dev/null
+++ b/tests/specs/run/import_attributes_static_error/static_error.ts
@@ -0,0 +1,3 @@
+import data from "./data.json";
+
+console.log(data);
diff --git a/tests/specs/run/import_attributes_static_export/__test__.jsonc b/tests/specs/run/import_attributes_static_export/__test__.jsonc
new file mode 100644
index 0000000000..05a64aab53
--- /dev/null
+++ b/tests/specs/run/import_attributes_static_export/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read static_export.ts",
+  "output": "static_export.out"
+}
diff --git a/tests/specs/run/import_attributes_static_export/data.json b/tests/specs/run/import_attributes_static_export/data.json
new file mode 100644
index 0000000000..37b3ee1e0a
--- /dev/null
+++ b/tests/specs/run/import_attributes_static_export/data.json
@@ -0,0 +1,6 @@
+{
+  "a": "b",
+  "c": {
+    "d": 10
+  }
+}
diff --git a/tests/specs/run/import_attributes_static_export/static_export.out b/tests/specs/run/import_attributes_static_export/static_export.out
new file mode 100644
index 0000000000..41af79d7c8
--- /dev/null
+++ b/tests/specs/run/import_attributes_static_export/static_export.out
@@ -0,0 +1 @@
+{ a: "b", c: { d: 10 } }
diff --git a/tests/specs/run/import_attributes_static_export/static_export.ts b/tests/specs/run/import_attributes_static_export/static_export.ts
new file mode 100644
index 0000000000..ac3ee694f5
--- /dev/null
+++ b/tests/specs/run/import_attributes_static_export/static_export.ts
@@ -0,0 +1,3 @@
+import data from "./static_reexport.ts";
+
+console.log(data);
diff --git a/tests/specs/run/import_attributes_static_export/static_reexport.ts b/tests/specs/run/import_attributes_static_export/static_reexport.ts
new file mode 100644
index 0000000000..e6175691c6
--- /dev/null
+++ b/tests/specs/run/import_attributes_static_export/static_reexport.ts
@@ -0,0 +1 @@
+export { default } from "./data.json" with { type: "json" };
diff --git a/tests/specs/run/import_attributes_static_import/__test__.jsonc b/tests/specs/run/import_attributes_static_import/__test__.jsonc
new file mode 100644
index 0000000000..4ea39e6d32
--- /dev/null
+++ b/tests/specs/run/import_attributes_static_import/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read static_import.ts",
+  "output": "static_import.out"
+}
diff --git a/tests/specs/run/import_attributes_static_import/data.json b/tests/specs/run/import_attributes_static_import/data.json
new file mode 100644
index 0000000000..37b3ee1e0a
--- /dev/null
+++ b/tests/specs/run/import_attributes_static_import/data.json
@@ -0,0 +1,6 @@
+{
+  "a": "b",
+  "c": {
+    "d": 10
+  }
+}
diff --git a/tests/specs/run/import_attributes_static_import/static_import.out b/tests/specs/run/import_attributes_static_import/static_import.out
new file mode 100644
index 0000000000..e57dffa992
--- /dev/null
+++ b/tests/specs/run/import_attributes_static_import/static_import.out
@@ -0,0 +1,2 @@
+{ a: "b", c: { d: 10 } }
+{ a: "b", c: { d: 10 } }
diff --git a/tests/specs/run/import_attributes_static_import/static_import.ts b/tests/specs/run/import_attributes_static_import/static_import.ts
new file mode 100644
index 0000000000..f585b893f3
--- /dev/null
+++ b/tests/specs/run/import_attributes_static_import/static_import.ts
@@ -0,0 +1,5 @@
+import data1 from "./data.json" with { type: "json" };
+import data2 from "./data.json" with { type: "json" };
+
+console.log(data1);
+console.log(data2);
diff --git a/tests/specs/run/import_attributes_type_check/__test__.jsonc b/tests/specs/run/import_attributes_type_check/__test__.jsonc
new file mode 100644
index 0000000000..89f6e0a79e
--- /dev/null
+++ b/tests/specs/run/import_attributes_type_check/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --allow-read --check type_check.ts",
+  "output": "type_check.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/import_attributes_type_check/data.json b/tests/specs/run/import_attributes_type_check/data.json
new file mode 100644
index 0000000000..37b3ee1e0a
--- /dev/null
+++ b/tests/specs/run/import_attributes_type_check/data.json
@@ -0,0 +1,6 @@
+{
+  "a": "b",
+  "c": {
+    "d": 10
+  }
+}
diff --git a/tests/specs/run/import_attributes_type_check/type_check.out b/tests/specs/run/import_attributes_type_check/type_check.out
new file mode 100644
index 0000000000..2fc26dae36
--- /dev/null
+++ b/tests/specs/run/import_attributes_type_check/type_check.out
@@ -0,0 +1,12 @@
+Check file:///[WILDCARD]/type_check.ts
+error: TS2339 [ERROR]: Property 'foo' does not exist on type '{ a: string; c: { d: number; }; }'.
+console.log(data1.foo);
+                  ~~~
+    at [WILDCARD]type_check.ts:5:19
+
+TS2339 [ERROR]: Property 'foo' does not exist on type '{ a: string; c: { d: number; }; }'.
+console.log(data2.foo);
+                  ~~~
+    at [WILDCARD]type_check.ts:6:19
+
+Found 2 errors.
diff --git a/tests/specs/run/import_attributes_type_check/type_check.ts b/tests/specs/run/import_attributes_type_check/type_check.ts
new file mode 100644
index 0000000000..36e47bd5b8
--- /dev/null
+++ b/tests/specs/run/import_attributes_type_check/type_check.ts
@@ -0,0 +1,6 @@
+import data1 from "./data.json" with { type: "json" };
+// deno-lint-ignore no-import-assertions
+import data2 from "./data.json" assert { type: "json" };
+
+console.log(data1.foo);
+console.log(data2.foo);
diff --git a/tests/specs/run/import_blob_url/__test__.jsonc b/tests/specs/run/import_blob_url/__test__.jsonc
new file mode 100644
index 0000000000..9ae6b5a423
--- /dev/null
+++ b/tests/specs/run/import_blob_url/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload import_blob_url.ts",
+  "output": "import_blob_url.ts.out"
+}
diff --git a/tests/testdata/run/import_blob_url.ts b/tests/specs/run/import_blob_url/import_blob_url.ts
similarity index 100%
rename from tests/testdata/run/import_blob_url.ts
rename to tests/specs/run/import_blob_url/import_blob_url.ts
diff --git a/tests/testdata/run/import_blob_url.ts.out b/tests/specs/run/import_blob_url/import_blob_url.ts.out
similarity index 100%
rename from tests/testdata/run/import_blob_url.ts.out
rename to tests/specs/run/import_blob_url/import_blob_url.ts.out
diff --git a/tests/specs/run/import_blob_url_error_stack/__test__.jsonc b/tests/specs/run/import_blob_url_error_stack/__test__.jsonc
new file mode 100644
index 0000000000..56a1489cd7
--- /dev/null
+++ b/tests/specs/run/import_blob_url_error_stack/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --reload import_blob_url_error_stack.ts",
+  "output": "import_blob_url_error_stack.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/import_blob_url_error_stack.ts b/tests/specs/run/import_blob_url_error_stack/import_blob_url_error_stack.ts
similarity index 100%
rename from tests/testdata/run/import_blob_url_error_stack.ts
rename to tests/specs/run/import_blob_url_error_stack/import_blob_url_error_stack.ts
diff --git a/tests/testdata/run/import_blob_url_error_stack.ts.out b/tests/specs/run/import_blob_url_error_stack/import_blob_url_error_stack.ts.out
similarity index 100%
rename from tests/testdata/run/import_blob_url_error_stack.ts.out
rename to tests/specs/run/import_blob_url_error_stack/import_blob_url_error_stack.ts.out
diff --git a/tests/specs/run/import_blob_url_import_relative/__test__.jsonc b/tests/specs/run/import_blob_url_import_relative/__test__.jsonc
new file mode 100644
index 0000000000..4fda81b311
--- /dev/null
+++ b/tests/specs/run/import_blob_url_import_relative/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --reload import_blob_url_import_relative.ts",
+  "output": "import_blob_url_import_relative.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/import_blob_url_import_relative.ts b/tests/specs/run/import_blob_url_import_relative/import_blob_url_import_relative.ts
similarity index 100%
rename from tests/testdata/run/import_blob_url_import_relative.ts
rename to tests/specs/run/import_blob_url_import_relative/import_blob_url_import_relative.ts
diff --git a/tests/testdata/run/import_blob_url_import_relative.ts.out b/tests/specs/run/import_blob_url_import_relative/import_blob_url_import_relative.ts.out
similarity index 100%
rename from tests/testdata/run/import_blob_url_import_relative.ts.out
rename to tests/specs/run/import_blob_url_import_relative/import_blob_url_import_relative.ts.out
diff --git a/tests/specs/run/import_blob_url_imports/__test__.jsonc b/tests/specs/run/import_blob_url_imports/__test__.jsonc
new file mode 100644
index 0000000000..511d22a593
--- /dev/null
+++ b/tests/specs/run/import_blob_url_imports/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --quiet --reload --allow-net=localhost:4545 import_blob_url_imports.ts",
+  "output": "import_blob_url_imports.ts.out"
+}
diff --git a/tests/testdata/run/import_blob_url_imports.ts b/tests/specs/run/import_blob_url_imports/import_blob_url_imports.ts
similarity index 100%
rename from tests/testdata/run/import_blob_url_imports.ts
rename to tests/specs/run/import_blob_url_imports/import_blob_url_imports.ts
diff --git a/tests/specs/run/import_blob_url_imports/import_blob_url_imports.ts.out b/tests/specs/run/import_blob_url_imports/import_blob_url_imports.ts.out
new file mode 100644
index 0000000000..e965047ad7
--- /dev/null
+++ b/tests/specs/run/import_blob_url_imports/import_blob_url_imports.ts.out
@@ -0,0 +1 @@
+Hello
diff --git a/tests/specs/run/import_blob_url_jsx/__test__.jsonc b/tests/specs/run/import_blob_url_jsx/__test__.jsonc
new file mode 100644
index 0000000000..985c6f8421
--- /dev/null
+++ b/tests/specs/run/import_blob_url_jsx/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload import_blob_url_jsx.ts",
+  "output": "import_blob_url_jsx.ts.out"
+}
diff --git a/tests/testdata/run/import_blob_url_jsx.ts b/tests/specs/run/import_blob_url_jsx/import_blob_url_jsx.ts
similarity index 100%
rename from tests/testdata/run/import_blob_url_jsx.ts
rename to tests/specs/run/import_blob_url_jsx/import_blob_url_jsx.ts
diff --git a/tests/testdata/run/import_blob_url_jsx.ts.out b/tests/specs/run/import_blob_url_jsx/import_blob_url_jsx.ts.out
similarity index 100%
rename from tests/testdata/run/import_blob_url_jsx.ts.out
rename to tests/specs/run/import_blob_url_jsx/import_blob_url_jsx.ts.out
diff --git a/tests/specs/run/import_common_js/__test__.jsonc b/tests/specs/run/import_common_js/__test__.jsonc
index 950c7f68c3..0602a09baa 100644
--- a/tests/specs/run/import_common_js/__test__.jsonc
+++ b/tests/specs/run/import_common_js/__test__.jsonc
@@ -1,16 +1,27 @@
 {
-  "steps": [
-    { "args": "run -R index.cjs", "output": "index.out" },
-    { "args": "run -R main.ts", "output": "main.out" },
-    {
+  "tests": {
+    "cjs_entrypoint": {
+      "args": "run -R index.cjs",
+      "output": "index.out"
+    },
+    "esm_entrypoint": {
+      "args": "run -R main.ts",
+      "output": "main.out"
+    },
+    "module_error": {
       "args": "run module_error.js",
       "output": "module_error.out",
       "exitCode": 1
     },
-    {
+    "exports_error": {
       "args": "run exports_error.js",
       "output": "exports_error.out",
       "exitCode": 1
+    },
+    "require_error": {
+      "args": "run require_error.js",
+      "output": "require_error.out",
+      "exitCode": 1
     }
-  ]
+  }
 }
diff --git a/tests/specs/run/import_common_js/a.js b/tests/specs/run/import_common_js/a.js
deleted file mode 100644
index c465ab588b..0000000000
--- a/tests/specs/run/import_common_js/a.js
+++ /dev/null
@@ -1,7 +0,0 @@
-function foobar() {
-  console.log("foobar");
-}
-
-module.exports = {
-  foobar,
-};
diff --git a/tests/specs/run/import_common_js/exports_error.out b/tests/specs/run/import_common_js/exports_error.out
index 41eda24575..baa44682be 100644
--- a/tests/specs/run/import_common_js/exports_error.out
+++ b/tests/specs/run/import_common_js/exports_error.out
@@ -3,5 +3,9 @@ Object.defineProperty(exports, "__esModule", { value: true });
                       ^
     at [WILDCARD]exports_error.js:1:23
 
-    info: Deno does not support CommonJS modules without `.cjs` extension.
-    hint: Rewrite this module to ESM or change the file extension to `.cjs`.
+    info: Deno supports CommonJS modules in .cjs files, or when the closest
+          package.json has a "type": "commonjs" option.
+    hint: Rewrite this module to ESM,
+          or change the file extension to .cjs,
+          or add package.json next to the file with "type": "commonjs" option.
+    docs: https://docs.deno.com/go/commonjs
diff --git a/tests/specs/run/import_common_js/index.cjs b/tests/specs/run/import_common_js/index.cjs
index 18caf81e94..0026e237d1 100644
--- a/tests/specs/run/import_common_js/index.cjs
+++ b/tests/specs/run/import_common_js/index.cjs
@@ -1,9 +1,7 @@
 const process = require("process");
-const a = require("./a");
 
 console.log(process.cwd());
 
 module.exports = {
   cwd: process.cwd,
-  foobar: a.foobar,
 };
diff --git a/tests/specs/run/import_common_js/index.out b/tests/specs/run/import_common_js/index.out
index 3650631b7a..6a734b9948 100644
--- a/tests/specs/run/import_common_js/index.out
+++ b/tests/specs/run/import_common_js/index.out
@@ -1 +1 @@
-[WILDCARD]import_common_js
+[WILDLINE]import_common_js
diff --git a/tests/specs/run/import_common_js/main.out b/tests/specs/run/import_common_js/main.out
index 03301b3620..9df3129754 100644
--- a/tests/specs/run/import_common_js/main.out
+++ b/tests/specs/run/import_common_js/main.out
@@ -1,5 +1,3 @@
 hello from foo node module
 [WILDCARD]import_common_js
 cjsModule.cwd() [WILDCARD]import_common_js
-foobar
-cjsModule.foobar() undefined
diff --git a/tests/specs/run/import_common_js/module_error.out b/tests/specs/run/import_common_js/module_error.out
index 53a908d291..957b19cb1e 100644
--- a/tests/specs/run/import_common_js/module_error.out
+++ b/tests/specs/run/import_common_js/module_error.out
@@ -3,5 +3,9 @@ module.exports = {
 ^
     at [WILDCARD]module_error.js:1:1
 
-    info: Deno does not support CommonJS modules without `.cjs` extension.
-    hint: Rewrite this module to ESM or change the file extension to `.cjs`.
+    info: Deno supports CommonJS modules in .cjs files, or when the closest
+          package.json has a "type": "commonjs" option.
+    hint: Rewrite this module to ESM,
+          or change the file extension to .cjs,
+          or add package.json next to the file with "type": "commonjs" option.
+    docs: https://docs.deno.com/go/commonjs
diff --git a/tests/specs/run/import_common_js/node_modules/foo/index.mjs b/tests/specs/run/import_common_js/node_modules/foo/index.mjs
index cc93554c73..7a11d39ae6 100644
--- a/tests/specs/run/import_common_js/node_modules/foo/index.mjs
+++ b/tests/specs/run/import_common_js/node_modules/foo/index.mjs
@@ -10,5 +10,4 @@ export default async function () {
     const cjsModule = await import(url.pathToFileURL(cjsFileToImport));
 
     console.log("cjsModule.cwd()", cjsModule.cwd());
-    console.log("cjsModule.foobar()", cjsModule.foobar());
 }
diff --git a/tests/specs/run/import_common_js/require_error.js b/tests/specs/run/import_common_js/require_error.js
new file mode 100644
index 0000000000..9567689331
--- /dev/null
+++ b/tests/specs/run/import_common_js/require_error.js
@@ -0,0 +1,2 @@
+const process = require("process");
+const a = require("./a");
diff --git a/tests/specs/run/import_common_js/require_error.out b/tests/specs/run/import_common_js/require_error.out
new file mode 100644
index 0000000000..e13db85e8e
--- /dev/null
+++ b/tests/specs/run/import_common_js/require_error.out
@@ -0,0 +1,11 @@
+error: Uncaught (in promise) ReferenceError: require is not defined
+const process = require("process");
+                ^
+    at [WILDCARD]require_error.js:1:17
+
+    info: Deno supports CommonJS modules in .cjs files, or when the closest
+          package.json has a "type": "commonjs" option.
+    hint: Rewrite this module to ESM,
+          or change the file extension to .cjs,
+          or add package.json next to the file with "type": "commonjs" option.
+    docs: https://docs.deno.com/go/commonjs
diff --git a/tests/specs/run/import_compression/__test__.jsonc b/tests/specs/run/import_compression/__test__.jsonc
new file mode 100644
index 0000000000..c8f7af9e1c
--- /dev/null
+++ b/tests/specs/run/import_compression/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --quiet --reload --allow-net import_compression/main.ts",
+  "output": "import_compression/main.out"
+}
diff --git a/tests/specs/run/import_compression/import_compression/brotli b/tests/specs/run/import_compression/import_compression/brotli
new file mode 100644
index 0000000000..65f679d571
--- /dev/null
+++ b/tests/specs/run/import_compression/import_compression/brotli
@@ -0,0 +1,2 @@
+�
+�console.log('brotli');
\ No newline at end of file
diff --git a/tests/specs/run/import_compression/import_compression/gziped b/tests/specs/run/import_compression/import_compression/gziped
new file mode 100644
index 0000000000..9f9a7bc690
Binary files /dev/null and b/tests/specs/run/import_compression/import_compression/gziped differ
diff --git a/tests/testdata/run/import_compression/main.out b/tests/specs/run/import_compression/import_compression/main.out
similarity index 100%
rename from tests/testdata/run/import_compression/main.out
rename to tests/specs/run/import_compression/import_compression/main.out
diff --git a/tests/testdata/run/import_compression/main.ts b/tests/specs/run/import_compression/import_compression/main.ts
similarity index 100%
rename from tests/testdata/run/import_compression/main.ts
rename to tests/specs/run/import_compression/import_compression/main.ts
diff --git a/tests/specs/run/import_data_url/__test__.jsonc b/tests/specs/run/import_data_url/__test__.jsonc
new file mode 100644
index 0000000000..95d1c94a34
--- /dev/null
+++ b/tests/specs/run/import_data_url/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload import_data_url.ts",
+  "output": "import_data_url.ts.out"
+}
diff --git a/tests/testdata/run/import_data_url.ts b/tests/specs/run/import_data_url/import_data_url.ts
similarity index 100%
rename from tests/testdata/run/import_data_url.ts
rename to tests/specs/run/import_data_url/import_data_url.ts
diff --git a/tests/testdata/run/import_data_url.ts.out b/tests/specs/run/import_data_url/import_data_url.ts.out
similarity index 100%
rename from tests/testdata/run/import_data_url.ts.out
rename to tests/specs/run/import_data_url/import_data_url.ts.out
diff --git a/tests/specs/run/import_data_url_error_stack/__test__.jsonc b/tests/specs/run/import_data_url_error_stack/__test__.jsonc
new file mode 100644
index 0000000000..851aae191d
--- /dev/null
+++ b/tests/specs/run/import_data_url_error_stack/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --reload import_data_url_error_stack.ts",
+  "output": "import_data_url_error_stack.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/import_data_url_error_stack.ts b/tests/specs/run/import_data_url_error_stack/import_data_url_error_stack.ts
similarity index 100%
rename from tests/testdata/run/import_data_url_error_stack.ts
rename to tests/specs/run/import_data_url_error_stack/import_data_url_error_stack.ts
diff --git a/tests/testdata/run/import_data_url_error_stack.ts.out b/tests/specs/run/import_data_url_error_stack/import_data_url_error_stack.ts.out
similarity index 100%
rename from tests/testdata/run/import_data_url_error_stack.ts.out
rename to tests/specs/run/import_data_url_error_stack/import_data_url_error_stack.ts.out
diff --git a/tests/specs/run/import_data_url_import_relative/__test__.jsonc b/tests/specs/run/import_data_url_import_relative/__test__.jsonc
new file mode 100644
index 0000000000..b241bc917c
--- /dev/null
+++ b/tests/specs/run/import_data_url_import_relative/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --reload import_data_url_import_relative.ts",
+  "output": "import_data_url_import_relative.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/import_data_url_import_relative.ts b/tests/specs/run/import_data_url_import_relative/import_data_url_import_relative.ts
similarity index 100%
rename from tests/testdata/run/import_data_url_import_relative.ts
rename to tests/specs/run/import_data_url_import_relative/import_data_url_import_relative.ts
diff --git a/tests/testdata/run/import_data_url_import_relative.ts.out b/tests/specs/run/import_data_url_import_relative/import_data_url_import_relative.ts.out
similarity index 100%
rename from tests/testdata/run/import_data_url_import_relative.ts.out
rename to tests/specs/run/import_data_url_import_relative/import_data_url_import_relative.ts.out
diff --git a/tests/specs/run/import_data_url_imports/__test__.jsonc b/tests/specs/run/import_data_url_imports/__test__.jsonc
new file mode 100644
index 0000000000..7fc8df315c
--- /dev/null
+++ b/tests/specs/run/import_data_url_imports/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --quiet --reload import_data_url_imports.ts",
+  "output": "import_data_url_imports.ts.out"
+}
diff --git a/tests/testdata/run/import_data_url_imports.ts b/tests/specs/run/import_data_url_imports/import_data_url_imports.ts
similarity index 100%
rename from tests/testdata/run/import_data_url_imports.ts
rename to tests/specs/run/import_data_url_imports/import_data_url_imports.ts
diff --git a/tests/specs/run/import_data_url_imports/import_data_url_imports.ts.out b/tests/specs/run/import_data_url_imports/import_data_url_imports.ts.out
new file mode 100644
index 0000000000..e965047ad7
--- /dev/null
+++ b/tests/specs/run/import_data_url_imports/import_data_url_imports.ts.out
@@ -0,0 +1 @@
+Hello
diff --git a/tests/specs/run/import_data_url_jsx/__test__.jsonc b/tests/specs/run/import_data_url_jsx/__test__.jsonc
new file mode 100644
index 0000000000..8fb1f9a1d9
--- /dev/null
+++ b/tests/specs/run/import_data_url_jsx/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload import_data_url_jsx.ts",
+  "output": "import_data_url_jsx.ts.out"
+}
diff --git a/tests/testdata/run/import_data_url_jsx.ts b/tests/specs/run/import_data_url_jsx/import_data_url_jsx.ts
similarity index 100%
rename from tests/testdata/run/import_data_url_jsx.ts
rename to tests/specs/run/import_data_url_jsx/import_data_url_jsx.ts
diff --git a/tests/testdata/run/import_data_url_jsx.ts.out b/tests/specs/run/import_data_url_jsx/import_data_url_jsx.ts.out
similarity index 100%
rename from tests/testdata/run/import_data_url_jsx.ts.out
rename to tests/specs/run/import_data_url_jsx/import_data_url_jsx.ts.out
diff --git a/tests/specs/run/import_dynamic_data_url/__test__.jsonc b/tests/specs/run/import_dynamic_data_url/__test__.jsonc
new file mode 100644
index 0000000000..09ff77f419
--- /dev/null
+++ b/tests/specs/run/import_dynamic_data_url/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload import_dynamic_data_url.ts",
+  "output": "import_dynamic_data_url.ts.out"
+}
diff --git a/tests/testdata/run/import_dynamic_data_url.ts b/tests/specs/run/import_dynamic_data_url/import_dynamic_data_url.ts
similarity index 100%
rename from tests/testdata/run/import_dynamic_data_url.ts
rename to tests/specs/run/import_dynamic_data_url/import_dynamic_data_url.ts
diff --git a/tests/testdata/run/import_dynamic_data_url.ts.out b/tests/specs/run/import_dynamic_data_url/import_dynamic_data_url.ts.out
similarity index 100%
rename from tests/testdata/run/import_dynamic_data_url.ts.out
rename to tests/specs/run/import_dynamic_data_url/import_dynamic_data_url.ts.out
diff --git a/tests/specs/run/import_extensionless/__test__.jsonc b/tests/specs/run/import_extensionless/__test__.jsonc
new file mode 100644
index 0000000000..cde59b5e22
--- /dev/null
+++ b/tests/specs/run/import_extensionless/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --quiet --reload import_extensionless.ts",
+  "output": "import_extensionless.ts.out"
+}
diff --git a/tests/testdata/run/import_extensionless.ts b/tests/specs/run/import_extensionless/import_extensionless.ts
similarity index 100%
rename from tests/testdata/run/import_extensionless.ts
rename to tests/specs/run/import_extensionless/import_extensionless.ts
diff --git a/tests/specs/run/import_extensionless/import_extensionless.ts.out b/tests/specs/run/import_extensionless/import_extensionless.ts.out
new file mode 100644
index 0000000000..e965047ad7
--- /dev/null
+++ b/tests/specs/run/import_extensionless/import_extensionless.ts.out
@@ -0,0 +1 @@
+Hello
diff --git a/tests/specs/run/import_file_with_colon/__test__.jsonc b/tests/specs/run/import_file_with_colon/__test__.jsonc
new file mode 100644
index 0000000000..5e6602ab3e
--- /dev/null
+++ b/tests/specs/run/import_file_with_colon/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --quiet --reload import_file_with_colon.ts",
+  "output": "import_file_with_colon.ts.out"
+}
diff --git a/tests/testdata/run/import_file_with_colon.ts b/tests/specs/run/import_file_with_colon/import_file_with_colon.ts
similarity index 100%
rename from tests/testdata/run/import_file_with_colon.ts
rename to tests/specs/run/import_file_with_colon/import_file_with_colon.ts
diff --git a/tests/testdata/run/import_file_with_colon.ts.out b/tests/specs/run/import_file_with_colon/import_file_with_colon.ts.out
similarity index 100%
rename from tests/testdata/run/import_file_with_colon.ts.out
rename to tests/specs/run/import_file_with_colon/import_file_with_colon.ts.out
diff --git a/tests/specs/run/import_type/__test__.jsonc b/tests/specs/run/import_type/__test__.jsonc
new file mode 100644
index 0000000000..2958483d00
--- /dev/null
+++ b/tests/specs/run/import_type/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload import_type.ts",
+  "output": "import_type.ts.out"
+}
diff --git a/tests/specs/run/import_type/export_types.ts b/tests/specs/run/import_type/export_types.ts
new file mode 100644
index 0000000000..18c8ed8810
--- /dev/null
+++ b/tests/specs/run/import_type/export_types.ts
@@ -0,0 +1,11 @@
+export interface A {
+  a: string;
+}
+
+export class B implements A {
+  a = "a";
+}
+
+export function create(): B {
+  return new B();
+}
diff --git a/tests/specs/run/import_type/import_type.ts b/tests/specs/run/import_type/import_type.ts
new file mode 100644
index 0000000000..91baba19aa
--- /dev/null
+++ b/tests/specs/run/import_type/import_type.ts
@@ -0,0 +1,5 @@
+import { type B, create } from "./export_types.ts";
+
+const b: B = create();
+
+console.log(b);
diff --git a/tests/testdata/run/import_type.ts.out b/tests/specs/run/import_type/import_type.ts.out
similarity index 100%
rename from tests/testdata/run/import_type.ts.out
rename to tests/specs/run/import_type/import_type.ts.out
diff --git a/tests/specs/run/import_type_no_check/__test__.jsonc b/tests/specs/run/import_type_no_check/__test__.jsonc
new file mode 100644
index 0000000000..d858f5fa10
--- /dev/null
+++ b/tests/specs/run/import_type_no_check/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload --no-check import_type.ts",
+  "output": "import_type.ts.out"
+}
diff --git a/tests/specs/run/import_type_no_check/export_types.ts b/tests/specs/run/import_type_no_check/export_types.ts
new file mode 100644
index 0000000000..18c8ed8810
--- /dev/null
+++ b/tests/specs/run/import_type_no_check/export_types.ts
@@ -0,0 +1,11 @@
+export interface A {
+  a: string;
+}
+
+export class B implements A {
+  a = "a";
+}
+
+export function create(): B {
+  return new B();
+}
diff --git a/tests/specs/run/import_type_no_check/import_type.ts b/tests/specs/run/import_type_no_check/import_type.ts
new file mode 100644
index 0000000000..91baba19aa
--- /dev/null
+++ b/tests/specs/run/import_type_no_check/import_type.ts
@@ -0,0 +1,5 @@
+import { type B, create } from "./export_types.ts";
+
+const b: B = create();
+
+console.log(b);
diff --git a/tests/specs/run/import_type_no_check/import_type.ts.out b/tests/specs/run/import_type_no_check/import_type.ts.out
new file mode 100644
index 0000000000..e35539e352
--- /dev/null
+++ b/tests/specs/run/import_type_no_check/import_type.ts.out
@@ -0,0 +1 @@
+B { a: "a" }
diff --git a/tests/specs/run/inline_js_source_map_2/__test__.jsonc b/tests/specs/run/inline_js_source_map_2/__test__.jsonc
new file mode 100644
index 0000000000..99ca6c1aed
--- /dev/null
+++ b/tests/specs/run/inline_js_source_map_2/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet inline_js_source_map_2.js",
+  "output": "inline_js_source_map_2.js.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/inline_js_source_map_2.js b/tests/specs/run/inline_js_source_map_2/inline_js_source_map_2.js
similarity index 84%
rename from tests/testdata/run/inline_js_source_map_2.js
rename to tests/specs/run/inline_js_source_map_2/inline_js_source_map_2.js
index d14d906b80..87132ee6a7 100644
--- a/tests/testdata/run/inline_js_source_map_2.js
+++ b/tests/specs/run/inline_js_source_map_2/inline_js_source_map_2.js
@@ -1,4 +1,4 @@
 "use strict";
 1 + 1;
 throw new Error("Hello world!");
-//# sourceMappingURL=data:application/json;base64,eyJ2ZXJzaW9uIjozLCJmaWxlIjoiIiwic291cmNlUm9vdCI6IiIsInNvdXJjZXMiOlsiaHR0cDovL2xvY2FsaG9zdDo0NTQ1L3J1bi9pbmxpbmVfanNfc291cmNlX21hcF8yLnRzIl0sIm5hbWVzIjpbXSwibWFwcGluZ3MiOiI7QUFBQSxDQUFDLEdBQUMsQ0FBQyxDQUFDO0FBS0osTUFBTSxJQUFJLEtBQUssQ0FBQyxjQUErQixDQUFDLENBQUMifQ==
\ No newline at end of file
+//# sourceMappingURL=data:application/json;base64,eyJ2ZXJzaW9uIjozLCJmaWxlIjoiIiwic291cmNlUm9vdCI6IiIsInNvdXJjZXMiOlsiaHR0cDovL2xvY2FsaG9zdDo0NTQ1L3J1bi9pbmxpbmVfanNfc291cmNlX21hcF8yLnRzIl0sIm5hbWVzIjpbXSwibWFwcGluZ3MiOiI7QUFBQSxDQUFDLEdBQUMsQ0FBQyxDQUFDO0FBS0osTUFBTSxJQUFJLEtBQUssQ0FBQyxjQUErQixDQUFDLENBQUMifQ==
diff --git a/tests/testdata/run/inline_js_source_map_2.js.out b/tests/specs/run/inline_js_source_map_2/inline_js_source_map_2.js.out
similarity index 100%
rename from tests/testdata/run/inline_js_source_map_2.js.out
rename to tests/specs/run/inline_js_source_map_2/inline_js_source_map_2.js.out
diff --git a/tests/specs/run/inline_js_source_map_2_with_inline_contents/__test__.jsonc b/tests/specs/run/inline_js_source_map_2_with_inline_contents/__test__.jsonc
new file mode 100644
index 0000000000..45fe6eba6d
--- /dev/null
+++ b/tests/specs/run/inline_js_source_map_2_with_inline_contents/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet inline_js_source_map_2_with_inline_contents.js",
+  "output": "inline_js_source_map_2_with_inline_contents.js.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/inline_js_source_map_2_with_inline_contents.js b/tests/specs/run/inline_js_source_map_2_with_inline_contents/inline_js_source_map_2_with_inline_contents.js
similarity index 93%
rename from tests/testdata/run/inline_js_source_map_2_with_inline_contents.js
rename to tests/specs/run/inline_js_source_map_2_with_inline_contents/inline_js_source_map_2_with_inline_contents.js
index 7660cc229b..41bee7fe4d 100644
--- a/tests/testdata/run/inline_js_source_map_2_with_inline_contents.js
+++ b/tests/specs/run/inline_js_source_map_2_with_inline_contents/inline_js_source_map_2_with_inline_contents.js
@@ -1,4 +1,4 @@
 "use strict";
 
 throw new Error("Hello world!");
-//# sourceMappingURL=data:application/json;base64,eyJ2ZXJzaW9uIjozLCJmaWxlIjoiIiwic291cmNlUm9vdCI6IiIsInNvdXJjZXMiOlsiaHR0cDovL2xvY2FsaG9zdDo0NTQ1L3J1bi9pbmxpbmVfanNfc291cmNlX21hcF8yLnRzIl0sInNvdXJjZXNDb250ZW50IjpbIjErMTtcbmludGVyZmFjZSBUZXN0IHtcbiAgaGVsbG86IHN0cmluZztcbn1cblxudGhyb3cgbmV3IEVycm9yKFwiSGVsbG8gd29ybGQhXCIgYXMgdW5rbm93biBhcyBzdHJpbmcpO1xuIl0sIm5hbWVzIjpbXSwibWFwcGluZ3MiOiI7QUFBQSxDQUFDLEdBQUMsQ0FBQyxDQUFDO0FBS0osTUFBTSxJQUFJLEtBQUssQ0FBQyxjQUErQixDQUFDLENBQUMifQ==
\ No newline at end of file
+//# sourceMappingURL=data:application/json;base64,eyJ2ZXJzaW9uIjozLCJmaWxlIjoiIiwic291cmNlUm9vdCI6IiIsInNvdXJjZXMiOlsiaHR0cDovL2xvY2FsaG9zdDo0NTQ1L3J1bi9pbmxpbmVfanNfc291cmNlX21hcF8yLnRzIl0sInNvdXJjZXNDb250ZW50IjpbIjErMTtcbmludGVyZmFjZSBUZXN0IHtcbiAgaGVsbG86IHN0cmluZztcbn1cblxudGhyb3cgbmV3IEVycm9yKFwiSGVsbG8gd29ybGQhXCIgYXMgdW5rbm93biBhcyBzdHJpbmcpO1xuIl0sIm5hbWVzIjpbXSwibWFwcGluZ3MiOiI7QUFBQSxDQUFDLEdBQUMsQ0FBQyxDQUFDO0FBS0osTUFBTSxJQUFJLEtBQUssQ0FBQyxjQUErQixDQUFDLENBQUMifQ==
diff --git a/tests/testdata/run/inline_js_source_map_2_with_inline_contents.js.out b/tests/specs/run/inline_js_source_map_2_with_inline_contents/inline_js_source_map_2_with_inline_contents.js.out
similarity index 100%
rename from tests/testdata/run/inline_js_source_map_2_with_inline_contents.js.out
rename to tests/specs/run/inline_js_source_map_2_with_inline_contents/inline_js_source_map_2_with_inline_contents.js.out
diff --git a/tests/specs/run/inline_js_source_map_with_contents_from_graph/__test__.jsonc b/tests/specs/run/inline_js_source_map_with_contents_from_graph/__test__.jsonc
new file mode 100644
index 0000000000..71dc4d509d
--- /dev/null
+++ b/tests/specs/run/inline_js_source_map_with_contents_from_graph/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --allow-import --quiet inline_js_source_map_with_contents_from_graph.js",
+  "output": "inline_js_source_map_with_contents_from_graph.js.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/inline_js_source_map_with_contents_from_graph.js b/tests/specs/run/inline_js_source_map_with_contents_from_graph/inline_js_source_map_with_contents_from_graph.js
similarity index 86%
rename from tests/testdata/run/inline_js_source_map_with_contents_from_graph.js
rename to tests/specs/run/inline_js_source_map_with_contents_from_graph/inline_js_source_map_with_contents_from_graph.js
index 887f023209..12fa1644df 100644
--- a/tests/testdata/run/inline_js_source_map_with_contents_from_graph.js
+++ b/tests/specs/run/inline_js_source_map_with_contents_from_graph/inline_js_source_map_with_contents_from_graph.js
@@ -1,4 +1,4 @@
 "use strict";
 import "http://localhost:4545/run/inline_js_source_map.ts";
 throw new Error("Hello world!");
-//# sourceMappingURL=data:application/json;base64,eyJ2ZXJzaW9uIjozLCJmaWxlIjoiIiwic291cmNlUm9vdCI6IiIsInNvdXJjZXMiOlsiaHR0cDovL2xvY2FsaG9zdDo0NTQ1L3J1bi9pbmxpbmVfanNfc291cmNlX21hcC50cyJdLCJuYW1lcyI6W10sIm1hcHBpbmdzIjoiO0FBQUEsQ0FBQyxHQUFDLENBQUMsQ0FBQztBQUtKLE1BQU0sSUFBSSxLQUFLLENBQUMsY0FBK0IsQ0FBQyxDQUFDIn0=
\ No newline at end of file
+//# sourceMappingURL=data:application/json;base64,eyJ2ZXJzaW9uIjozLCJmaWxlIjoiIiwic291cmNlUm9vdCI6IiIsInNvdXJjZXMiOlsiaHR0cDovL2xvY2FsaG9zdDo0NTQ1L3J1bi9pbmxpbmVfanNfc291cmNlX21hcC50cyJdLCJuYW1lcyI6W10sIm1hcHBpbmdzIjoiO0FBQUEsQ0FBQyxHQUFDLENBQUMsQ0FBQztBQUtKLE1BQU0sSUFBSSxLQUFLLENBQUMsY0FBK0IsQ0FBQyxDQUFDIn0=
diff --git a/tests/testdata/run/inline_js_source_map_with_contents_from_graph.js.out b/tests/specs/run/inline_js_source_map_with_contents_from_graph/inline_js_source_map_with_contents_from_graph.js.out
similarity index 100%
rename from tests/testdata/run/inline_js_source_map_with_contents_from_graph.js.out
rename to tests/specs/run/inline_js_source_map_with_contents_from_graph/inline_js_source_map_with_contents_from_graph.js.out
diff --git a/tests/specs/run/issue_13562/__test__.jsonc b/tests/specs/run/issue_13562/__test__.jsonc
new file mode 100644
index 0000000000..1971d552b6
--- /dev/null
+++ b/tests/specs/run/issue_13562/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run issue13562.ts",
+  "output": "issue13562.ts.out"
+}
diff --git a/tests/specs/run/issue_13562/issue13562.ts b/tests/specs/run/issue_13562/issue13562.ts
new file mode 100644
index 0000000000..51e97629b6
--- /dev/null
+++ b/tests/specs/run/issue_13562/issue13562.ts
@@ -0,0 +1,3 @@
+import { printHello3 } from "./mod1.ts?q=.json";
+
+printHello3();
diff --git a/tests/specs/run/issue_13562/issue13562.ts.out b/tests/specs/run/issue_13562/issue13562.ts.out
new file mode 100644
index 0000000000..e965047ad7
--- /dev/null
+++ b/tests/specs/run/issue_13562/issue13562.ts.out
@@ -0,0 +1 @@
+Hello
diff --git a/tests/specs/run/issue_13562/mod1.ts b/tests/specs/run/issue_13562/mod1.ts
new file mode 100644
index 0000000000..5e58f432ed
--- /dev/null
+++ b/tests/specs/run/issue_13562/mod1.ts
@@ -0,0 +1,17 @@
+import { printHello2, returnsFoo } from "./subdir2/mod2.ts";
+
+export function returnsHi(): string {
+  return "Hi";
+}
+
+export function returnsFoo2(): string {
+  return returnsFoo();
+}
+
+export function printHello3() {
+  printHello2();
+}
+
+export function throwsError() {
+  throw Error("exception from mod1");
+}
diff --git a/tests/specs/run/issue_13562/print_hello.ts b/tests/specs/run/issue_13562/print_hello.ts
new file mode 100644
index 0000000000..b9c0ad5275
--- /dev/null
+++ b/tests/specs/run/issue_13562/print_hello.ts
@@ -0,0 +1,3 @@
+export function printHello() {
+  console.log("Hello");
+}
diff --git a/tests/specs/run/issue_13562/subdir2/dynamic_import.ts b/tests/specs/run/issue_13562/subdir2/dynamic_import.ts
new file mode 100644
index 0000000000..59beb64c33
--- /dev/null
+++ b/tests/specs/run/issue_13562/subdir2/dynamic_import.ts
@@ -0,0 +1,4 @@
+(async () => {
+  const { printHello } = await import("../mod2.ts");
+  printHello();
+})();
diff --git a/tests/specs/run/issue_13562/subdir2/mod2.ts b/tests/specs/run/issue_13562/subdir2/mod2.ts
new file mode 100644
index 0000000000..9071d0aeb4
--- /dev/null
+++ b/tests/specs/run/issue_13562/subdir2/mod2.ts
@@ -0,0 +1,9 @@
+import { printHello } from "../print_hello.ts";
+
+export function returnsFoo(): string {
+  return "Foo";
+}
+
+export function printHello2() {
+  printHello();
+}
diff --git a/tests/specs/run/js_import_detect/__test__.jsonc b/tests/specs/run/js_import_detect/__test__.jsonc
new file mode 100644
index 0000000000..6a648f4763
--- /dev/null
+++ b/tests/specs/run/js_import_detect/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --reload js_import_detect.ts",
+  "output": "js_import_detect.ts.out",
+  "exitCode": 0
+}
diff --git a/tests/testdata/run/js_import_detect.ts b/tests/specs/run/js_import_detect/js_import_detect.ts
similarity index 100%
rename from tests/testdata/run/js_import_detect.ts
rename to tests/specs/run/js_import_detect/js_import_detect.ts
diff --git a/tests/testdata/run/js_import_detect.ts.out b/tests/specs/run/js_import_detect/js_import_detect.ts.out
similarity index 100%
rename from tests/testdata/run/js_import_detect.ts.out
rename to tests/specs/run/js_import_detect/js_import_detect.ts.out
diff --git a/tests/specs/run/js_root_with_ts_check/__test__.jsonc b/tests/specs/run/js_root_with_ts_check/__test__.jsonc
new file mode 100644
index 0000000000..ebc4d75987
--- /dev/null
+++ b/tests/specs/run/js_root_with_ts_check/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --check js_root_with_ts_check.js",
+  "output": "js_root_with_ts_check.js.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/js_root_with_ts_check.js b/tests/specs/run/js_root_with_ts_check/js_root_with_ts_check.js
similarity index 100%
rename from tests/testdata/run/js_root_with_ts_check.js
rename to tests/specs/run/js_root_with_ts_check/js_root_with_ts_check.js
diff --git a/tests/testdata/run/js_root_with_ts_check.js.out b/tests/specs/run/js_root_with_ts_check/js_root_with_ts_check.js.out
similarity index 100%
rename from tests/testdata/run/js_root_with_ts_check.js.out
rename to tests/specs/run/js_root_with_ts_check/js_root_with_ts_check.js.out
diff --git a/tests/specs/run/js_without_extension/__test__.jsonc b/tests/specs/run/js_without_extension/__test__.jsonc
new file mode 100644
index 0000000000..0d2aac73b4
--- /dev/null
+++ b/tests/specs/run/js_without_extension/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --ext js --check js_without_extension",
+  "output": "js_without_extension.out",
+  "exitCode": 0
+}
diff --git a/tests/specs/run/js_without_extension/js_without_extension b/tests/specs/run/js_without_extension/js_without_extension
new file mode 100644
index 0000000000..4774be3263
--- /dev/null
+++ b/tests/specs/run/js_without_extension/js_without_extension
@@ -0,0 +1,3 @@
+let i = 123;
+i = "hello"
+console.log("executing javascript with no extension");
diff --git a/tests/specs/run/js_without_extension/js_without_extension.out b/tests/specs/run/js_without_extension/js_without_extension.out
new file mode 100644
index 0000000000..1236c1e534
--- /dev/null
+++ b/tests/specs/run/js_without_extension/js_without_extension.out
@@ -0,0 +1 @@
+executing javascript with no extension
diff --git a/tests/specs/run/jsx_import_from_ts/__test__.jsonc b/tests/specs/run/jsx_import_from_ts/__test__.jsonc
new file mode 100644
index 0000000000..0f89205dc1
--- /dev/null
+++ b/tests/specs/run/jsx_import_from_ts/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload jsx_import_from_ts.ts",
+  "output": "jsx_import_from_ts.ts.out"
+}
diff --git a/tests/specs/run/jsx_import_from_ts/jsx_import_from_ts.App.jsx b/tests/specs/run/jsx_import_from_ts/jsx_import_from_ts.App.jsx
new file mode 100644
index 0000000000..649230613c
--- /dev/null
+++ b/tests/specs/run/jsx_import_from_ts/jsx_import_from_ts.App.jsx
@@ -0,0 +1,11 @@
+const React = {
+  createElement() {},
+};
+
+export default function app() {
+  return (
+    <div>
+      <h2>asdf</h2>
+    </div>
+  );
+}
diff --git a/tests/testdata/run/jsx_import_from_ts.ts b/tests/specs/run/jsx_import_from_ts/jsx_import_from_ts.ts
similarity index 100%
rename from tests/testdata/run/jsx_import_from_ts.ts
rename to tests/specs/run/jsx_import_from_ts/jsx_import_from_ts.ts
diff --git a/tests/testdata/run/jsx_import_from_ts.ts.out b/tests/specs/run/jsx_import_from_ts/jsx_import_from_ts.ts.out
similarity index 100%
rename from tests/testdata/run/jsx_import_from_ts.ts.out
rename to tests/specs/run/jsx_import_from_ts/jsx_import_from_ts.ts.out
diff --git a/tests/specs/run/jsx_import_source_error/__test__.jsonc b/tests/specs/run/jsx_import_source_error/__test__.jsonc
new file mode 100644
index 0000000000..22b1d29cab
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_error/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --config jsx/deno-jsx-error.jsonc --check jsx_import_source_no_pragma.tsx",
+  "output": "jsx_import_source_error.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/jsx_import_source_error/jsx/deno-jsx-error.jsonc b/tests/specs/run/jsx_import_source_error/jsx/deno-jsx-error.jsonc
new file mode 100644
index 0000000000..37cb4dd912
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_error/jsx/deno-jsx-error.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "./nonexistent"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_error/jsx/deno-jsx-import-map.jsonc b/tests/specs/run/jsx_import_source_error/jsx/deno-jsx-import-map.jsonc
new file mode 100644
index 0000000000..5adbfa8b5a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_error/jsx/deno-jsx-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_error/jsx/deno-jsx-precompile-skip.jsonc b/tests/specs/run/jsx_import_source_error/jsx/deno-jsx-precompile-skip.jsonc
new file mode 100644
index 0000000000..3c9e4fa1f8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_error/jsx/deno-jsx-precompile-skip.jsonc
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile",
+    "jsxPrecompileSkipElements": ["a", "img"]
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_error/jsx/deno-jsx-precompile.jsonc b/tests/specs/run/jsx_import_source_error/jsx/deno-jsx-precompile.jsonc
new file mode 100644
index 0000000000..95ae1b9f31
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_error/jsx/deno-jsx-precompile.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_error/jsx/deno-jsx.json b/tests/specs/run/jsx_import_source_error/jsx/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_error/jsx/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_error/jsx/deno-jsx.jsonc b/tests/specs/run/jsx_import_source_error/jsx/deno-jsx.jsonc
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_error/jsx/deno-jsx.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_error/jsx/deno-jsxdev-import-map.jsonc b/tests/specs/run/jsx_import_source_error/jsx/deno-jsxdev-import-map.jsonc
new file mode 100644
index 0000000000..7481d5a2d8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_error/jsx/deno-jsxdev-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_error/jsx/deno-jsxdev.jsonc b/tests/specs/run/jsx_import_source_error/jsx/deno-jsxdev.jsonc
new file mode 100644
index 0000000000..ae5bdf9f16
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_error/jsx/deno-jsxdev.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_error/jsx/deno.lock b/tests/specs/run/jsx_import_source_error/jsx/deno.lock
new file mode 100644
index 0000000000..011e8fe108
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_error/jsx/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/jsx/jsx-dev-runtime/index.ts": "183c5bf1cfb82b15fc1e8cca15593d4816035759532d851abd4476df378c8412"
+  }
+}
\ No newline at end of file
diff --git a/tests/specs/run/jsx_import_source_error/jsx/import-map-scoped.json b/tests/specs/run/jsx_import_source_error/jsx/import-map-scoped.json
new file mode 100644
index 0000000000..9b2005128f
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_error/jsx/import-map-scoped.json
@@ -0,0 +1,8 @@
+{
+  "scopes": {
+    "../subdir/": {
+      "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+      "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts"
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_error/jsx/import-map.json b/tests/specs/run/jsx_import_source_error/jsx/import-map.json
new file mode 100644
index 0000000000..1bfa04e2f0
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_error/jsx/import-map.json
@@ -0,0 +1,7 @@
+{
+  "imports": {
+    "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+    "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts",
+    "jsx-precompile/jsx-runtime": "http://localhost:4545/jsx/jsx-precompile/index.ts"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_error/jsx/jsx-dev-runtime/index.ts b/tests/specs/run/jsx_import_source_error/jsx/jsx-dev-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_error/jsx/jsx-dev-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_error/jsx/jsx-precompile/index.ts b/tests/specs/run/jsx_import_source_error/jsx/jsx-precompile/index.ts
new file mode 100644
index 0000000000..0d56095e0b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_error/jsx/jsx-precompile/index.ts
@@ -0,0 +1,23 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+// deno-lint-ignore-file no-explicit-any
+export const jsxAttr = (name: string, value: any) => `${name}="${value}"`;
+// deno-lint-ignore-file no-explicit-any
+export const jsxTemplate = (_template: string[], ..._exprs: any[]) => "";
+// deno-lint-ignore-file no-explicit-any
+export const jsxEscape = (_value: any) => "";
+console.log("imported", import.meta.url);
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      [tagName: string]: Record<string, any>;
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_error/jsx/jsx-runtime/index.ts b/tests/specs/run/jsx_import_source_error/jsx/jsx-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_error/jsx/jsx-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/testdata/run/jsx_import_source_error.out b/tests/specs/run/jsx_import_source_error/jsx_import_source_error.out
similarity index 100%
rename from tests/testdata/run/jsx_import_source_error.out
rename to tests/specs/run/jsx_import_source_error/jsx_import_source_error.out
diff --git a/tests/specs/run/jsx_import_source_error/jsx_import_source_no_pragma.tsx b/tests/specs/run/jsx_import_source_error/jsx_import_source_no_pragma.tsx
new file mode 100644
index 0000000000..2c756054fb
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_error/jsx_import_source_no_pragma.tsx
@@ -0,0 +1,7 @@
+function A() {
+  return "hello";
+}
+
+export function B() {
+  return <A></A>;
+}
diff --git a/tests/specs/run/jsx_import_source_import_map/__test__.jsonc b/tests/specs/run/jsx_import_source_import_map/__test__.jsonc
new file mode 100644
index 0000000000..8a62c5243b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --reload --import-map jsx/import-map.json --no-lock --config jsx/deno-jsx-import-map.jsonc jsx_import_source_no_pragma.tsx",
+  "output": "jsx_import_source_import_map.out"
+}
diff --git a/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsx-error.jsonc b/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsx-error.jsonc
new file mode 100644
index 0000000000..37cb4dd912
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsx-error.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "./nonexistent"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsx-import-map.jsonc b/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsx-import-map.jsonc
new file mode 100644
index 0000000000..5adbfa8b5a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsx-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsx-precompile-skip.jsonc b/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsx-precompile-skip.jsonc
new file mode 100644
index 0000000000..3c9e4fa1f8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsx-precompile-skip.jsonc
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile",
+    "jsxPrecompileSkipElements": ["a", "img"]
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsx-precompile.jsonc b/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsx-precompile.jsonc
new file mode 100644
index 0000000000..95ae1b9f31
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsx-precompile.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsx.json b/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsx.jsonc b/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsx.jsonc
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsx.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsxdev-import-map.jsonc b/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsxdev-import-map.jsonc
new file mode 100644
index 0000000000..7481d5a2d8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsxdev-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsxdev.jsonc b/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsxdev.jsonc
new file mode 100644
index 0000000000..ae5bdf9f16
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map/jsx/deno-jsxdev.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map/jsx/deno.lock b/tests/specs/run/jsx_import_source_import_map/jsx/deno.lock
new file mode 100644
index 0000000000..011e8fe108
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map/jsx/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/jsx/jsx-dev-runtime/index.ts": "183c5bf1cfb82b15fc1e8cca15593d4816035759532d851abd4476df378c8412"
+  }
+}
\ No newline at end of file
diff --git a/tests/specs/run/jsx_import_source_import_map/jsx/import-map-scoped.json b/tests/specs/run/jsx_import_source_import_map/jsx/import-map-scoped.json
new file mode 100644
index 0000000000..9b2005128f
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map/jsx/import-map-scoped.json
@@ -0,0 +1,8 @@
+{
+  "scopes": {
+    "../subdir/": {
+      "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+      "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts"
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map/jsx/import-map.json b/tests/specs/run/jsx_import_source_import_map/jsx/import-map.json
new file mode 100644
index 0000000000..1bfa04e2f0
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map/jsx/import-map.json
@@ -0,0 +1,7 @@
+{
+  "imports": {
+    "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+    "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts",
+    "jsx-precompile/jsx-runtime": "http://localhost:4545/jsx/jsx-precompile/index.ts"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map/jsx/jsx-dev-runtime/index.ts b/tests/specs/run/jsx_import_source_import_map/jsx/jsx-dev-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map/jsx/jsx-dev-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_import_map/jsx/jsx-precompile/index.ts b/tests/specs/run/jsx_import_source_import_map/jsx/jsx-precompile/index.ts
new file mode 100644
index 0000000000..0d56095e0b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map/jsx/jsx-precompile/index.ts
@@ -0,0 +1,23 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+// deno-lint-ignore-file no-explicit-any
+export const jsxAttr = (name: string, value: any) => `${name}="${value}"`;
+// deno-lint-ignore-file no-explicit-any
+export const jsxTemplate = (_template: string[], ..._exprs: any[]) => "";
+// deno-lint-ignore-file no-explicit-any
+export const jsxEscape = (_value: any) => "";
+console.log("imported", import.meta.url);
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      [tagName: string]: Record<string, any>;
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map/jsx/jsx-runtime/index.ts b/tests/specs/run/jsx_import_source_import_map/jsx/jsx-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map/jsx/jsx-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_import_map/jsx_import_source_import_map.out b/tests/specs/run/jsx_import_source_import_map/jsx_import_source_import_map.out
new file mode 100644
index 0000000000..0d32389677
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map/jsx_import_source_import_map.out
@@ -0,0 +1,2 @@
+[WILDCARD]
+imported http://localhost:4545/jsx/jsx-runtime/index.ts
diff --git a/tests/specs/run/jsx_import_source_import_map/jsx_import_source_no_pragma.tsx b/tests/specs/run/jsx_import_source_import_map/jsx_import_source_no_pragma.tsx
new file mode 100644
index 0000000000..2c756054fb
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map/jsx_import_source_no_pragma.tsx
@@ -0,0 +1,7 @@
+function A() {
+  return "hello";
+}
+
+export function B() {
+  return <A></A>;
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_dev/__test__.jsonc b/tests/specs/run/jsx_import_source_import_map_dev/__test__.jsonc
new file mode 100644
index 0000000000..b62e7cb6f3
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_dev/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --reload --import-map jsx/import-map.json --no-lock --config jsx/deno-jsxdev-import-map.jsonc jsx_import_source_no_pragma.tsx",
+  "output": "jsx_import_source_import_map_dev.out"
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsx-error.jsonc b/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsx-error.jsonc
new file mode 100644
index 0000000000..37cb4dd912
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsx-error.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "./nonexistent"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsx-import-map.jsonc b/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsx-import-map.jsonc
new file mode 100644
index 0000000000..5adbfa8b5a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsx-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsx-precompile-skip.jsonc b/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsx-precompile-skip.jsonc
new file mode 100644
index 0000000000..3c9e4fa1f8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsx-precompile-skip.jsonc
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile",
+    "jsxPrecompileSkipElements": ["a", "img"]
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsx-precompile.jsonc b/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsx-precompile.jsonc
new file mode 100644
index 0000000000..95ae1b9f31
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsx-precompile.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsx.json b/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsx.jsonc b/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsx.jsonc
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsx.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsxdev-import-map.jsonc b/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsxdev-import-map.jsonc
new file mode 100644
index 0000000000..7481d5a2d8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsxdev-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsxdev.jsonc b/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsxdev.jsonc
new file mode 100644
index 0000000000..ae5bdf9f16
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno-jsxdev.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno.lock b/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno.lock
new file mode 100644
index 0000000000..011e8fe108
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_dev/jsx/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/jsx/jsx-dev-runtime/index.ts": "183c5bf1cfb82b15fc1e8cca15593d4816035759532d851abd4476df378c8412"
+  }
+}
\ No newline at end of file
diff --git a/tests/specs/run/jsx_import_source_import_map_dev/jsx/import-map-scoped.json b/tests/specs/run/jsx_import_source_import_map_dev/jsx/import-map-scoped.json
new file mode 100644
index 0000000000..9b2005128f
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_dev/jsx/import-map-scoped.json
@@ -0,0 +1,8 @@
+{
+  "scopes": {
+    "../subdir/": {
+      "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+      "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts"
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_dev/jsx/import-map.json b/tests/specs/run/jsx_import_source_import_map_dev/jsx/import-map.json
new file mode 100644
index 0000000000..1bfa04e2f0
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_dev/jsx/import-map.json
@@ -0,0 +1,7 @@
+{
+  "imports": {
+    "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+    "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts",
+    "jsx-precompile/jsx-runtime": "http://localhost:4545/jsx/jsx-precompile/index.ts"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_dev/jsx/jsx-dev-runtime/index.ts b/tests/specs/run/jsx_import_source_import_map_dev/jsx/jsx-dev-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_dev/jsx/jsx-dev-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_import_map_dev/jsx/jsx-precompile/index.ts b/tests/specs/run/jsx_import_source_import_map_dev/jsx/jsx-precompile/index.ts
new file mode 100644
index 0000000000..0d56095e0b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_dev/jsx/jsx-precompile/index.ts
@@ -0,0 +1,23 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+// deno-lint-ignore-file no-explicit-any
+export const jsxAttr = (name: string, value: any) => `${name}="${value}"`;
+// deno-lint-ignore-file no-explicit-any
+export const jsxTemplate = (_template: string[], ..._exprs: any[]) => "";
+// deno-lint-ignore-file no-explicit-any
+export const jsxEscape = (_value: any) => "";
+console.log("imported", import.meta.url);
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      [tagName: string]: Record<string, any>;
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_dev/jsx/jsx-runtime/index.ts b/tests/specs/run/jsx_import_source_import_map_dev/jsx/jsx-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_dev/jsx/jsx-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_import_map_dev/jsx_import_source_import_map_dev.out b/tests/specs/run/jsx_import_source_import_map_dev/jsx_import_source_import_map_dev.out
new file mode 100644
index 0000000000..56f514d90c
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_dev/jsx_import_source_import_map_dev.out
@@ -0,0 +1,2 @@
+[WILDCARD]
+imported http://localhost:4545/jsx/jsx-dev-runtime/index.ts
diff --git a/tests/specs/run/jsx_import_source_import_map_dev/jsx_import_source_no_pragma.tsx b/tests/specs/run/jsx_import_source_import_map_dev/jsx_import_source_no_pragma.tsx
new file mode 100644
index 0000000000..2c756054fb
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_dev/jsx_import_source_no_pragma.tsx
@@ -0,0 +1,7 @@
+function A() {
+  return "hello";
+}
+
+export function B() {
+  return <A></A>;
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_no_check/__test__.jsonc b/tests/specs/run/jsx_import_source_import_map_no_check/__test__.jsonc
new file mode 100644
index 0000000000..ea42654848
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_no_check/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --reload --import-map jsx/import-map.json --no-lock --config jsx/deno-jsx-import-map.jsonc --no-check jsx_import_source_no_pragma.tsx",
+  "output": "jsx_import_source_import_map.out"
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsx-error.jsonc b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsx-error.jsonc
new file mode 100644
index 0000000000..37cb4dd912
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsx-error.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "./nonexistent"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsx-import-map.jsonc b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsx-import-map.jsonc
new file mode 100644
index 0000000000..5adbfa8b5a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsx-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsx-precompile-skip.jsonc b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsx-precompile-skip.jsonc
new file mode 100644
index 0000000000..3c9e4fa1f8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsx-precompile-skip.jsonc
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile",
+    "jsxPrecompileSkipElements": ["a", "img"]
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsx-precompile.jsonc b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsx-precompile.jsonc
new file mode 100644
index 0000000000..95ae1b9f31
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsx-precompile.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsx.json b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsx.jsonc b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsx.jsonc
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsx.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsxdev-import-map.jsonc b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsxdev-import-map.jsonc
new file mode 100644
index 0000000000..7481d5a2d8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsxdev-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsxdev.jsonc b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsxdev.jsonc
new file mode 100644
index 0000000000..ae5bdf9f16
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno-jsxdev.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno.lock b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno.lock
new file mode 100644
index 0000000000..011e8fe108
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/jsx/jsx-dev-runtime/index.ts": "183c5bf1cfb82b15fc1e8cca15593d4816035759532d851abd4476df378c8412"
+  }
+}
\ No newline at end of file
diff --git a/tests/specs/run/jsx_import_source_import_map_no_check/jsx/import-map-scoped.json b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/import-map-scoped.json
new file mode 100644
index 0000000000..9b2005128f
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/import-map-scoped.json
@@ -0,0 +1,8 @@
+{
+  "scopes": {
+    "../subdir/": {
+      "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+      "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts"
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_no_check/jsx/import-map.json b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/import-map.json
new file mode 100644
index 0000000000..1bfa04e2f0
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/import-map.json
@@ -0,0 +1,7 @@
+{
+  "imports": {
+    "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+    "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts",
+    "jsx-precompile/jsx-runtime": "http://localhost:4545/jsx/jsx-precompile/index.ts"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_no_check/jsx/jsx-dev-runtime/index.ts b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/jsx-dev-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/jsx-dev-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_import_map_no_check/jsx/jsx-precompile/index.ts b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/jsx-precompile/index.ts
new file mode 100644
index 0000000000..0d56095e0b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/jsx-precompile/index.ts
@@ -0,0 +1,23 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+// deno-lint-ignore-file no-explicit-any
+export const jsxAttr = (name: string, value: any) => `${name}="${value}"`;
+// deno-lint-ignore-file no-explicit-any
+export const jsxTemplate = (_template: string[], ..._exprs: any[]) => "";
+// deno-lint-ignore-file no-explicit-any
+export const jsxEscape = (_value: any) => "";
+console.log("imported", import.meta.url);
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      [tagName: string]: Record<string, any>;
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_import_map_no_check/jsx/jsx-runtime/index.ts b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/jsx-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_no_check/jsx/jsx-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_import_map_no_check/jsx_import_source_import_map.out b/tests/specs/run/jsx_import_source_import_map_no_check/jsx_import_source_import_map.out
new file mode 100644
index 0000000000..0d32389677
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_no_check/jsx_import_source_import_map.out
@@ -0,0 +1,2 @@
+[WILDCARD]
+imported http://localhost:4545/jsx/jsx-runtime/index.ts
diff --git a/tests/specs/run/jsx_import_source_import_map_no_check/jsx_import_source_no_pragma.tsx b/tests/specs/run/jsx_import_source_import_map_no_check/jsx_import_source_no_pragma.tsx
new file mode 100644
index 0000000000..2c756054fb
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_import_map_no_check/jsx_import_source_no_pragma.tsx
@@ -0,0 +1,7 @@
+function A() {
+  return "hello";
+}
+
+export function B() {
+  return <A></A>;
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma/__test__.jsonc b/tests/specs/run/jsx_import_source_no_pragma/__test__.jsonc
new file mode 100644
index 0000000000..7678e18f46
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --reload --config jsx/deno-jsx.jsonc --no-lock jsx_import_source_no_pragma.tsx",
+  "output": "jsx_import_source.out"
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsx-error.jsonc b/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsx-error.jsonc
new file mode 100644
index 0000000000..37cb4dd912
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsx-error.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "./nonexistent"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsx-import-map.jsonc b/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsx-import-map.jsonc
new file mode 100644
index 0000000000..5adbfa8b5a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsx-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsx-precompile-skip.jsonc b/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsx-precompile-skip.jsonc
new file mode 100644
index 0000000000..3c9e4fa1f8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsx-precompile-skip.jsonc
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile",
+    "jsxPrecompileSkipElements": ["a", "img"]
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsx-precompile.jsonc b/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsx-precompile.jsonc
new file mode 100644
index 0000000000..95ae1b9f31
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsx-precompile.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsx.json b/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsx.jsonc b/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsx.jsonc
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsx.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsxdev-import-map.jsonc b/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsxdev-import-map.jsonc
new file mode 100644
index 0000000000..7481d5a2d8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsxdev-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsxdev.jsonc b/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsxdev.jsonc
new file mode 100644
index 0000000000..ae5bdf9f16
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma/jsx/deno-jsxdev.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma/jsx/deno.lock b/tests/specs/run/jsx_import_source_no_pragma/jsx/deno.lock
new file mode 100644
index 0000000000..011e8fe108
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma/jsx/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/jsx/jsx-dev-runtime/index.ts": "183c5bf1cfb82b15fc1e8cca15593d4816035759532d851abd4476df378c8412"
+  }
+}
\ No newline at end of file
diff --git a/tests/specs/run/jsx_import_source_no_pragma/jsx/import-map-scoped.json b/tests/specs/run/jsx_import_source_no_pragma/jsx/import-map-scoped.json
new file mode 100644
index 0000000000..9b2005128f
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma/jsx/import-map-scoped.json
@@ -0,0 +1,8 @@
+{
+  "scopes": {
+    "../subdir/": {
+      "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+      "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts"
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma/jsx/import-map.json b/tests/specs/run/jsx_import_source_no_pragma/jsx/import-map.json
new file mode 100644
index 0000000000..1bfa04e2f0
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma/jsx/import-map.json
@@ -0,0 +1,7 @@
+{
+  "imports": {
+    "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+    "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts",
+    "jsx-precompile/jsx-runtime": "http://localhost:4545/jsx/jsx-precompile/index.ts"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma/jsx/jsx-dev-runtime/index.ts b/tests/specs/run/jsx_import_source_no_pragma/jsx/jsx-dev-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma/jsx/jsx-dev-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_no_pragma/jsx/jsx-precompile/index.ts b/tests/specs/run/jsx_import_source_no_pragma/jsx/jsx-precompile/index.ts
new file mode 100644
index 0000000000..0d56095e0b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma/jsx/jsx-precompile/index.ts
@@ -0,0 +1,23 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+// deno-lint-ignore-file no-explicit-any
+export const jsxAttr = (name: string, value: any) => `${name}="${value}"`;
+// deno-lint-ignore-file no-explicit-any
+export const jsxTemplate = (_template: string[], ..._exprs: any[]) => "";
+// deno-lint-ignore-file no-explicit-any
+export const jsxEscape = (_value: any) => "";
+console.log("imported", import.meta.url);
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      [tagName: string]: Record<string, any>;
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma/jsx/jsx-runtime/index.ts b/tests/specs/run/jsx_import_source_no_pragma/jsx/jsx-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma/jsx/jsx-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/testdata/run/jsx_import_source.out b/tests/specs/run/jsx_import_source_no_pragma/jsx_import_source.out
similarity index 100%
rename from tests/testdata/run/jsx_import_source.out
rename to tests/specs/run/jsx_import_source_no_pragma/jsx_import_source.out
diff --git a/tests/specs/run/jsx_import_source_no_pragma/jsx_import_source_no_pragma.tsx b/tests/specs/run/jsx_import_source_no_pragma/jsx_import_source_no_pragma.tsx
new file mode 100644
index 0000000000..2c756054fb
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma/jsx_import_source_no_pragma.tsx
@@ -0,0 +1,7 @@
+function A() {
+  return "hello";
+}
+
+export function B() {
+  return <A></A>;
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_dev/__test__.jsonc b/tests/specs/run/jsx_import_source_no_pragma_dev/__test__.jsonc
new file mode 100644
index 0000000000..8f9ee81f69
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_dev/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --reload --config jsx/deno-jsxdev.jsonc --no-lock jsx_import_source_no_pragma.tsx",
+  "output": "jsx_import_source_dev.out"
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsx-error.jsonc b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsx-error.jsonc
new file mode 100644
index 0000000000..37cb4dd912
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsx-error.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "./nonexistent"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsx-import-map.jsonc b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsx-import-map.jsonc
new file mode 100644
index 0000000000..5adbfa8b5a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsx-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsx-precompile-skip.jsonc b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsx-precompile-skip.jsonc
new file mode 100644
index 0000000000..3c9e4fa1f8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsx-precompile-skip.jsonc
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile",
+    "jsxPrecompileSkipElements": ["a", "img"]
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsx-precompile.jsonc b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsx-precompile.jsonc
new file mode 100644
index 0000000000..95ae1b9f31
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsx-precompile.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsx.json b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsx.jsonc b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsx.jsonc
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsx.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsxdev-import-map.jsonc b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsxdev-import-map.jsonc
new file mode 100644
index 0000000000..7481d5a2d8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsxdev-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsxdev.jsonc b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsxdev.jsonc
new file mode 100644
index 0000000000..ae5bdf9f16
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno-jsxdev.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno.lock b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno.lock
new file mode 100644
index 0000000000..011e8fe108
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/jsx/jsx-dev-runtime/index.ts": "183c5bf1cfb82b15fc1e8cca15593d4816035759532d851abd4476df378c8412"
+  }
+}
\ No newline at end of file
diff --git a/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/import-map-scoped.json b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/import-map-scoped.json
new file mode 100644
index 0000000000..9b2005128f
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/import-map-scoped.json
@@ -0,0 +1,8 @@
+{
+  "scopes": {
+    "../subdir/": {
+      "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+      "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts"
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/import-map.json b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/import-map.json
new file mode 100644
index 0000000000..1bfa04e2f0
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/import-map.json
@@ -0,0 +1,7 @@
+{
+  "imports": {
+    "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+    "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts",
+    "jsx-precompile/jsx-runtime": "http://localhost:4545/jsx/jsx-precompile/index.ts"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/jsx-dev-runtime/index.ts b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/jsx-dev-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/jsx-dev-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/jsx-precompile/index.ts b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/jsx-precompile/index.ts
new file mode 100644
index 0000000000..0d56095e0b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/jsx-precompile/index.ts
@@ -0,0 +1,23 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+// deno-lint-ignore-file no-explicit-any
+export const jsxAttr = (name: string, value: any) => `${name}="${value}"`;
+// deno-lint-ignore-file no-explicit-any
+export const jsxTemplate = (_template: string[], ..._exprs: any[]) => "";
+// deno-lint-ignore-file no-explicit-any
+export const jsxEscape = (_value: any) => "";
+console.log("imported", import.meta.url);
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      [tagName: string]: Record<string, any>;
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/jsx-runtime/index.ts b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/jsx-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx/jsx-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/testdata/run/jsx_import_source_dev.out b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx_import_source_dev.out
similarity index 100%
rename from tests/testdata/run/jsx_import_source_dev.out
rename to tests/specs/run/jsx_import_source_no_pragma_dev/jsx_import_source_dev.out
diff --git a/tests/specs/run/jsx_import_source_no_pragma_dev/jsx_import_source_no_pragma.tsx b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx_import_source_no_pragma.tsx
new file mode 100644
index 0000000000..2c756054fb
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_dev/jsx_import_source_no_pragma.tsx
@@ -0,0 +1,7 @@
+function A() {
+  return "hello";
+}
+
+export function B() {
+  return <A></A>;
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_no_check/__test__.jsonc b/tests/specs/run/jsx_import_source_no_pragma_no_check/__test__.jsonc
new file mode 100644
index 0000000000..12cc9b0764
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_no_check/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --reload --config jsx/deno-jsx.jsonc --no-lock --no-check jsx_import_source_no_pragma.tsx",
+  "output": "jsx_import_source.out"
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsx-error.jsonc b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsx-error.jsonc
new file mode 100644
index 0000000000..37cb4dd912
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsx-error.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "./nonexistent"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsx-import-map.jsonc b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsx-import-map.jsonc
new file mode 100644
index 0000000000..5adbfa8b5a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsx-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsx-precompile-skip.jsonc b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsx-precompile-skip.jsonc
new file mode 100644
index 0000000000..3c9e4fa1f8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsx-precompile-skip.jsonc
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile",
+    "jsxPrecompileSkipElements": ["a", "img"]
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsx-precompile.jsonc b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsx-precompile.jsonc
new file mode 100644
index 0000000000..95ae1b9f31
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsx-precompile.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsx.json b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsx.jsonc b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsx.jsonc
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsx.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsxdev-import-map.jsonc b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsxdev-import-map.jsonc
new file mode 100644
index 0000000000..7481d5a2d8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsxdev-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsxdev.jsonc b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsxdev.jsonc
new file mode 100644
index 0000000000..ae5bdf9f16
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno-jsxdev.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno.lock b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno.lock
new file mode 100644
index 0000000000..011e8fe108
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/jsx/jsx-dev-runtime/index.ts": "183c5bf1cfb82b15fc1e8cca15593d4816035759532d851abd4476df378c8412"
+  }
+}
\ No newline at end of file
diff --git a/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/import-map-scoped.json b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/import-map-scoped.json
new file mode 100644
index 0000000000..9b2005128f
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/import-map-scoped.json
@@ -0,0 +1,8 @@
+{
+  "scopes": {
+    "../subdir/": {
+      "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+      "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts"
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/import-map.json b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/import-map.json
new file mode 100644
index 0000000000..1bfa04e2f0
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/import-map.json
@@ -0,0 +1,7 @@
+{
+  "imports": {
+    "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+    "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts",
+    "jsx-precompile/jsx-runtime": "http://localhost:4545/jsx/jsx-precompile/index.ts"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/jsx-dev-runtime/index.ts b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/jsx-dev-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/jsx-dev-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/jsx-precompile/index.ts b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/jsx-precompile/index.ts
new file mode 100644
index 0000000000..0d56095e0b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/jsx-precompile/index.ts
@@ -0,0 +1,23 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+// deno-lint-ignore-file no-explicit-any
+export const jsxAttr = (name: string, value: any) => `${name}="${value}"`;
+// deno-lint-ignore-file no-explicit-any
+export const jsxTemplate = (_template: string[], ..._exprs: any[]) => "";
+// deno-lint-ignore-file no-explicit-any
+export const jsxEscape = (_value: any) => "";
+console.log("imported", import.meta.url);
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      [tagName: string]: Record<string, any>;
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/jsx-runtime/index.ts b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/jsx-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx/jsx-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx_import_source.out b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx_import_source.out
new file mode 100644
index 0000000000..b9555987a6
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx_import_source.out
@@ -0,0 +1,2 @@
+[WILDCARD]
+imported http://localhost:4545/jsx/jsx-runtime
diff --git a/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx_import_source_no_pragma.tsx b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx_import_source_no_pragma.tsx
new file mode 100644
index 0000000000..2c756054fb
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_no_pragma_no_check/jsx_import_source_no_pragma.tsx
@@ -0,0 +1,7 @@
+function A() {
+  return "hello";
+}
+
+export function B() {
+  return <A></A>;
+}
diff --git a/tests/specs/run/jsx_import_source_pragma/__test__.jsonc b/tests/specs/run/jsx_import_source_pragma/__test__.jsonc
new file mode 100644
index 0000000000..9d704c0650
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload --allow-import jsx_import_source_pragma.tsx",
+  "output": "jsx_import_source.out"
+}
diff --git a/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsx-error.jsonc b/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsx-error.jsonc
new file mode 100644
index 0000000000..37cb4dd912
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsx-error.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "./nonexistent"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsx-import-map.jsonc b/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsx-import-map.jsonc
new file mode 100644
index 0000000000..5adbfa8b5a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsx-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsx-precompile-skip.jsonc b/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsx-precompile-skip.jsonc
new file mode 100644
index 0000000000..3c9e4fa1f8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsx-precompile-skip.jsonc
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile",
+    "jsxPrecompileSkipElements": ["a", "img"]
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsx-precompile.jsonc b/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsx-precompile.jsonc
new file mode 100644
index 0000000000..95ae1b9f31
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsx-precompile.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsx.json b/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsx.jsonc b/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsx.jsonc
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsx.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsxdev-import-map.jsonc b/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsxdev-import-map.jsonc
new file mode 100644
index 0000000000..7481d5a2d8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsxdev-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsxdev.jsonc b/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsxdev.jsonc
new file mode 100644
index 0000000000..ae5bdf9f16
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma/jsx/deno-jsxdev.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma/jsx/deno.lock b/tests/specs/run/jsx_import_source_pragma/jsx/deno.lock
new file mode 100644
index 0000000000..011e8fe108
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma/jsx/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/jsx/jsx-dev-runtime/index.ts": "183c5bf1cfb82b15fc1e8cca15593d4816035759532d851abd4476df378c8412"
+  }
+}
\ No newline at end of file
diff --git a/tests/specs/run/jsx_import_source_pragma/jsx/import-map-scoped.json b/tests/specs/run/jsx_import_source_pragma/jsx/import-map-scoped.json
new file mode 100644
index 0000000000..9b2005128f
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma/jsx/import-map-scoped.json
@@ -0,0 +1,8 @@
+{
+  "scopes": {
+    "../subdir/": {
+      "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+      "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts"
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma/jsx/import-map.json b/tests/specs/run/jsx_import_source_pragma/jsx/import-map.json
new file mode 100644
index 0000000000..1bfa04e2f0
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma/jsx/import-map.json
@@ -0,0 +1,7 @@
+{
+  "imports": {
+    "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+    "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts",
+    "jsx-precompile/jsx-runtime": "http://localhost:4545/jsx/jsx-precompile/index.ts"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma/jsx/jsx-dev-runtime/index.ts b/tests/specs/run/jsx_import_source_pragma/jsx/jsx-dev-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma/jsx/jsx-dev-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma/jsx/jsx-precompile/index.ts b/tests/specs/run/jsx_import_source_pragma/jsx/jsx-precompile/index.ts
new file mode 100644
index 0000000000..0d56095e0b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma/jsx/jsx-precompile/index.ts
@@ -0,0 +1,23 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+// deno-lint-ignore-file no-explicit-any
+export const jsxAttr = (name: string, value: any) => `${name}="${value}"`;
+// deno-lint-ignore-file no-explicit-any
+export const jsxTemplate = (_template: string[], ..._exprs: any[]) => "";
+// deno-lint-ignore-file no-explicit-any
+export const jsxEscape = (_value: any) => "";
+console.log("imported", import.meta.url);
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      [tagName: string]: Record<string, any>;
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma/jsx/jsx-runtime/index.ts b/tests/specs/run/jsx_import_source_pragma/jsx/jsx-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma/jsx/jsx-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma/jsx_import_source.out b/tests/specs/run/jsx_import_source_pragma/jsx_import_source.out
new file mode 100644
index 0000000000..b9555987a6
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma/jsx_import_source.out
@@ -0,0 +1,2 @@
+[WILDCARD]
+imported http://localhost:4545/jsx/jsx-runtime
diff --git a/tests/testdata/run/jsx_import_source_pragma.tsx b/tests/specs/run/jsx_import_source_pragma/jsx_import_source_pragma.tsx
similarity index 100%
rename from tests/testdata/run/jsx_import_source_pragma.tsx
rename to tests/specs/run/jsx_import_source_pragma/jsx_import_source_pragma.tsx
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map/__test__.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map/__test__.jsonc
new file mode 100644
index 0000000000..9eafe51968
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --reload --import-map jsx/import-map.json jsx_import_source_pragma_import_map.tsx",
+  "output": "jsx_import_source_import_map.out"
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsx-error.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsx-error.jsonc
new file mode 100644
index 0000000000..37cb4dd912
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsx-error.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "./nonexistent"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsx-import-map.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsx-import-map.jsonc
new file mode 100644
index 0000000000..5adbfa8b5a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsx-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsx-precompile-skip.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsx-precompile-skip.jsonc
new file mode 100644
index 0000000000..3c9e4fa1f8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsx-precompile-skip.jsonc
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile",
+    "jsxPrecompileSkipElements": ["a", "img"]
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsx-precompile.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsx-precompile.jsonc
new file mode 100644
index 0000000000..95ae1b9f31
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsx-precompile.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsx.json b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsx.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsx.jsonc
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsx.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsxdev-import-map.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsxdev-import-map.jsonc
new file mode 100644
index 0000000000..7481d5a2d8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsxdev-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsxdev.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsxdev.jsonc
new file mode 100644
index 0000000000..ae5bdf9f16
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno-jsxdev.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno.lock b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno.lock
new file mode 100644
index 0000000000..011e8fe108
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/jsx/jsx-dev-runtime/index.ts": "183c5bf1cfb82b15fc1e8cca15593d4816035759532d851abd4476df378c8412"
+  }
+}
\ No newline at end of file
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map/jsx/import-map-scoped.json b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/import-map-scoped.json
new file mode 100644
index 0000000000..9b2005128f
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/import-map-scoped.json
@@ -0,0 +1,8 @@
+{
+  "scopes": {
+    "../subdir/": {
+      "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+      "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts"
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map/jsx/import-map.json b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/import-map.json
new file mode 100644
index 0000000000..1bfa04e2f0
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/import-map.json
@@ -0,0 +1,7 @@
+{
+  "imports": {
+    "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+    "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts",
+    "jsx-precompile/jsx-runtime": "http://localhost:4545/jsx/jsx-precompile/index.ts"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map/jsx/jsx-dev-runtime/index.ts b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/jsx-dev-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/jsx-dev-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map/jsx/jsx-precompile/index.ts b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/jsx-precompile/index.ts
new file mode 100644
index 0000000000..0d56095e0b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/jsx-precompile/index.ts
@@ -0,0 +1,23 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+// deno-lint-ignore-file no-explicit-any
+export const jsxAttr = (name: string, value: any) => `${name}="${value}"`;
+// deno-lint-ignore-file no-explicit-any
+export const jsxTemplate = (_template: string[], ..._exprs: any[]) => "";
+// deno-lint-ignore-file no-explicit-any
+export const jsxEscape = (_value: any) => "";
+console.log("imported", import.meta.url);
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      [tagName: string]: Record<string, any>;
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map/jsx/jsx-runtime/index.ts b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/jsx-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map/jsx/jsx-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map/jsx_import_source_import_map.out b/tests/specs/run/jsx_import_source_pragma_import_map/jsx_import_source_import_map.out
new file mode 100644
index 0000000000..0d32389677
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map/jsx_import_source_import_map.out
@@ -0,0 +1,2 @@
+[WILDCARD]
+imported http://localhost:4545/jsx/jsx-runtime/index.ts
diff --git a/tests/testdata/run/jsx_import_source_pragma_import_map.tsx b/tests/specs/run/jsx_import_source_pragma_import_map/jsx_import_source_pragma_import_map.tsx
similarity index 100%
rename from tests/testdata/run/jsx_import_source_pragma_import_map.tsx
rename to tests/specs/run/jsx_import_source_pragma_import_map/jsx_import_source_pragma_import_map.tsx
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_dev/__test__.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map_dev/__test__.jsonc
new file mode 100644
index 0000000000..bb271c0eef
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_dev/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --reload --import-map jsx/import-map.json --config jsx/deno-jsxdev-import-map.jsonc jsx_import_source_pragma_import_map.tsx",
+  "output": "jsx_import_source_import_map_dev.out"
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsx-error.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsx-error.jsonc
new file mode 100644
index 0000000000..37cb4dd912
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsx-error.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "./nonexistent"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsx-import-map.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsx-import-map.jsonc
new file mode 100644
index 0000000000..5adbfa8b5a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsx-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsx-precompile-skip.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsx-precompile-skip.jsonc
new file mode 100644
index 0000000000..3c9e4fa1f8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsx-precompile-skip.jsonc
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile",
+    "jsxPrecompileSkipElements": ["a", "img"]
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsx-precompile.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsx-precompile.jsonc
new file mode 100644
index 0000000000..95ae1b9f31
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsx-precompile.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsx.json b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsx.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsx.jsonc
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsx.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsxdev-import-map.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsxdev-import-map.jsonc
new file mode 100644
index 0000000000..7481d5a2d8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsxdev-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsxdev.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsxdev.jsonc
new file mode 100644
index 0000000000..ae5bdf9f16
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno-jsxdev.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno.lock b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno.lock
new file mode 100644
index 0000000000..011e8fe108
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/jsx/jsx-dev-runtime/index.ts": "183c5bf1cfb82b15fc1e8cca15593d4816035759532d851abd4476df378c8412"
+  }
+}
\ No newline at end of file
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/import-map-scoped.json b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/import-map-scoped.json
new file mode 100644
index 0000000000..9b2005128f
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/import-map-scoped.json
@@ -0,0 +1,8 @@
+{
+  "scopes": {
+    "../subdir/": {
+      "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+      "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts"
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/import-map.json b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/import-map.json
new file mode 100644
index 0000000000..1bfa04e2f0
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/import-map.json
@@ -0,0 +1,7 @@
+{
+  "imports": {
+    "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+    "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts",
+    "jsx-precompile/jsx-runtime": "http://localhost:4545/jsx/jsx-precompile/index.ts"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/jsx-dev-runtime/index.ts b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/jsx-dev-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/jsx-dev-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/jsx-precompile/index.ts b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/jsx-precompile/index.ts
new file mode 100644
index 0000000000..0d56095e0b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/jsx-precompile/index.ts
@@ -0,0 +1,23 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+// deno-lint-ignore-file no-explicit-any
+export const jsxAttr = (name: string, value: any) => `${name}="${value}"`;
+// deno-lint-ignore-file no-explicit-any
+export const jsxTemplate = (_template: string[], ..._exprs: any[]) => "";
+// deno-lint-ignore-file no-explicit-any
+export const jsxEscape = (_value: any) => "";
+console.log("imported", import.meta.url);
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      [tagName: string]: Record<string, any>;
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/jsx-runtime/index.ts b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/jsx-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx/jsx-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx_import_source_import_map_dev.out b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx_import_source_import_map_dev.out
new file mode 100644
index 0000000000..56f514d90c
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx_import_source_import_map_dev.out
@@ -0,0 +1,2 @@
+[WILDCARD]
+imported http://localhost:4545/jsx/jsx-dev-runtime/index.ts
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx_import_source_pragma_import_map.tsx b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx_import_source_pragma_import_map.tsx
new file mode 100644
index 0000000000..548365f182
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_dev/jsx_import_source_pragma_import_map.tsx
@@ -0,0 +1,9 @@
+/** @jsxImportSource jsx */
+
+function A() {
+  return "hello";
+}
+
+export function B() {
+  return <A></A>;
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_no_check/__test__.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/__test__.jsonc
new file mode 100644
index 0000000000..dd42b71fda
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --reload --import-map jsx/import-map.json --no-check jsx_import_source_pragma_import_map.tsx",
+  "output": "jsx_import_source_import_map.out"
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsx-error.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsx-error.jsonc
new file mode 100644
index 0000000000..37cb4dd912
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsx-error.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "./nonexistent"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsx-import-map.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsx-import-map.jsonc
new file mode 100644
index 0000000000..5adbfa8b5a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsx-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsx-precompile-skip.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsx-precompile-skip.jsonc
new file mode 100644
index 0000000000..3c9e4fa1f8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsx-precompile-skip.jsonc
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile",
+    "jsxPrecompileSkipElements": ["a", "img"]
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsx-precompile.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsx-precompile.jsonc
new file mode 100644
index 0000000000..95ae1b9f31
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsx-precompile.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsx.json b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsx.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsx.jsonc
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsx.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsxdev-import-map.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsxdev-import-map.jsonc
new file mode 100644
index 0000000000..7481d5a2d8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsxdev-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsxdev.jsonc b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsxdev.jsonc
new file mode 100644
index 0000000000..ae5bdf9f16
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno-jsxdev.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno.lock b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno.lock
new file mode 100644
index 0000000000..011e8fe108
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/jsx/jsx-dev-runtime/index.ts": "183c5bf1cfb82b15fc1e8cca15593d4816035759532d851abd4476df378c8412"
+  }
+}
\ No newline at end of file
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/import-map-scoped.json b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/import-map-scoped.json
new file mode 100644
index 0000000000..9b2005128f
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/import-map-scoped.json
@@ -0,0 +1,8 @@
+{
+  "scopes": {
+    "../subdir/": {
+      "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+      "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts"
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/import-map.json b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/import-map.json
new file mode 100644
index 0000000000..1bfa04e2f0
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/import-map.json
@@ -0,0 +1,7 @@
+{
+  "imports": {
+    "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+    "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts",
+    "jsx-precompile/jsx-runtime": "http://localhost:4545/jsx/jsx-precompile/index.ts"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/jsx-dev-runtime/index.ts b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/jsx-dev-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/jsx-dev-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/jsx-precompile/index.ts b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/jsx-precompile/index.ts
new file mode 100644
index 0000000000..0d56095e0b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/jsx-precompile/index.ts
@@ -0,0 +1,23 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+// deno-lint-ignore-file no-explicit-any
+export const jsxAttr = (name: string, value: any) => `${name}="${value}"`;
+// deno-lint-ignore-file no-explicit-any
+export const jsxTemplate = (_template: string[], ..._exprs: any[]) => "";
+// deno-lint-ignore-file no-explicit-any
+export const jsxEscape = (_value: any) => "";
+console.log("imported", import.meta.url);
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      [tagName: string]: Record<string, any>;
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/jsx-runtime/index.ts b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/jsx-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx/jsx-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx_import_source_import_map.out b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx_import_source_import_map.out
new file mode 100644
index 0000000000..0d32389677
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx_import_source_import_map.out
@@ -0,0 +1,2 @@
+[WILDCARD]
+imported http://localhost:4545/jsx/jsx-runtime/index.ts
diff --git a/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx_import_source_pragma_import_map.tsx b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx_import_source_pragma_import_map.tsx
new file mode 100644
index 0000000000..548365f182
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_import_map_no_check/jsx_import_source_pragma_import_map.tsx
@@ -0,0 +1,9 @@
+/** @jsxImportSource jsx */
+
+function A() {
+  return "hello";
+}
+
+export function B() {
+  return <A></A>;
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_no_check/__test__.jsonc b/tests/specs/run/jsx_import_source_pragma_no_check/__test__.jsonc
new file mode 100644
index 0000000000..0956b94a76
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_no_check/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --reload --no-check jsx_import_source_pragma.tsx",
+  "output": "jsx_import_source.out"
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsx-error.jsonc b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsx-error.jsonc
new file mode 100644
index 0000000000..37cb4dd912
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsx-error.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "./nonexistent"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsx-import-map.jsonc b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsx-import-map.jsonc
new file mode 100644
index 0000000000..5adbfa8b5a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsx-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsx-precompile-skip.jsonc b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsx-precompile-skip.jsonc
new file mode 100644
index 0000000000..3c9e4fa1f8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsx-precompile-skip.jsonc
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile",
+    "jsxPrecompileSkipElements": ["a", "img"]
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsx-precompile.jsonc b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsx-precompile.jsonc
new file mode 100644
index 0000000000..95ae1b9f31
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsx-precompile.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsx.json b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsx.jsonc b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsx.jsonc
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsx.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsxdev-import-map.jsonc b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsxdev-import-map.jsonc
new file mode 100644
index 0000000000..7481d5a2d8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsxdev-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsxdev.jsonc b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsxdev.jsonc
new file mode 100644
index 0000000000..ae5bdf9f16
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno-jsxdev.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno.lock b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno.lock
new file mode 100644
index 0000000000..011e8fe108
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/jsx/jsx-dev-runtime/index.ts": "183c5bf1cfb82b15fc1e8cca15593d4816035759532d851abd4476df378c8412"
+  }
+}
\ No newline at end of file
diff --git a/tests/specs/run/jsx_import_source_pragma_no_check/jsx/import-map-scoped.json b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/import-map-scoped.json
new file mode 100644
index 0000000000..9b2005128f
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/import-map-scoped.json
@@ -0,0 +1,8 @@
+{
+  "scopes": {
+    "../subdir/": {
+      "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+      "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts"
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_no_check/jsx/import-map.json b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/import-map.json
new file mode 100644
index 0000000000..1bfa04e2f0
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/import-map.json
@@ -0,0 +1,7 @@
+{
+  "imports": {
+    "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+    "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts",
+    "jsx-precompile/jsx-runtime": "http://localhost:4545/jsx/jsx-precompile/index.ts"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_no_check/jsx/jsx-dev-runtime/index.ts b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/jsx-dev-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/jsx-dev-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma_no_check/jsx/jsx-precompile/index.ts b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/jsx-precompile/index.ts
new file mode 100644
index 0000000000..0d56095e0b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/jsx-precompile/index.ts
@@ -0,0 +1,23 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+// deno-lint-ignore-file no-explicit-any
+export const jsxAttr = (name: string, value: any) => `${name}="${value}"`;
+// deno-lint-ignore-file no-explicit-any
+export const jsxTemplate = (_template: string[], ..._exprs: any[]) => "";
+// deno-lint-ignore-file no-explicit-any
+export const jsxEscape = (_value: any) => "";
+console.log("imported", import.meta.url);
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      [tagName: string]: Record<string, any>;
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_no_check/jsx/jsx-runtime/index.ts b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/jsx-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_no_check/jsx/jsx-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma_no_check/jsx_import_source.out b/tests/specs/run/jsx_import_source_pragma_no_check/jsx_import_source.out
new file mode 100644
index 0000000000..b9555987a6
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_no_check/jsx_import_source.out
@@ -0,0 +1,2 @@
+[WILDCARD]
+imported http://localhost:4545/jsx/jsx-runtime
diff --git a/tests/specs/run/jsx_import_source_pragma_no_check/jsx_import_source_pragma.tsx b/tests/specs/run/jsx_import_source_pragma_no_check/jsx_import_source_pragma.tsx
new file mode 100644
index 0000000000..c19e53d4ff
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_no_check/jsx_import_source_pragma.tsx
@@ -0,0 +1,9 @@
+/** @jsxImportSource http://localhost:4545/jsx */
+
+function A() {
+  return "hello";
+}
+
+export function B() {
+  return <A></A>;
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config/__test__.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config/__test__.jsonc
new file mode 100644
index 0000000000..aeaf209c3a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload --allow-import --config jsx/deno-jsx.jsonc --no-lock jsx_import_source_pragma.tsx",
+  "output": "jsx_import_source.out"
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsx-error.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsx-error.jsonc
new file mode 100644
index 0000000000..37cb4dd912
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsx-error.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "./nonexistent"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsx-import-map.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsx-import-map.jsonc
new file mode 100644
index 0000000000..5adbfa8b5a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsx-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsx-precompile-skip.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsx-precompile-skip.jsonc
new file mode 100644
index 0000000000..3c9e4fa1f8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsx-precompile-skip.jsonc
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile",
+    "jsxPrecompileSkipElements": ["a", "img"]
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsx-precompile.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsx-precompile.jsonc
new file mode 100644
index 0000000000..95ae1b9f31
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsx-precompile.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsx.json b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsx.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsx.jsonc
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsx.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsxdev-import-map.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsxdev-import-map.jsonc
new file mode 100644
index 0000000000..7481d5a2d8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsxdev-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsxdev.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsxdev.jsonc
new file mode 100644
index 0000000000..ae5bdf9f16
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno-jsxdev.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno.lock b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno.lock
new file mode 100644
index 0000000000..011e8fe108
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/jsx/jsx-dev-runtime/index.ts": "183c5bf1cfb82b15fc1e8cca15593d4816035759532d851abd4476df378c8412"
+  }
+}
\ No newline at end of file
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config/jsx/import-map-scoped.json b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/import-map-scoped.json
new file mode 100644
index 0000000000..9b2005128f
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/import-map-scoped.json
@@ -0,0 +1,8 @@
+{
+  "scopes": {
+    "../subdir/": {
+      "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+      "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts"
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config/jsx/import-map.json b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/import-map.json
new file mode 100644
index 0000000000..1bfa04e2f0
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/import-map.json
@@ -0,0 +1,7 @@
+{
+  "imports": {
+    "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+    "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts",
+    "jsx-precompile/jsx-runtime": "http://localhost:4545/jsx/jsx-precompile/index.ts"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config/jsx/jsx-dev-runtime/index.ts b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/jsx-dev-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/jsx-dev-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config/jsx/jsx-precompile/index.ts b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/jsx-precompile/index.ts
new file mode 100644
index 0000000000..0d56095e0b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/jsx-precompile/index.ts
@@ -0,0 +1,23 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+// deno-lint-ignore-file no-explicit-any
+export const jsxAttr = (name: string, value: any) => `${name}="${value}"`;
+// deno-lint-ignore-file no-explicit-any
+export const jsxTemplate = (_template: string[], ..._exprs: any[]) => "";
+// deno-lint-ignore-file no-explicit-any
+export const jsxEscape = (_value: any) => "";
+console.log("imported", import.meta.url);
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      [tagName: string]: Record<string, any>;
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config/jsx/jsx-runtime/index.ts b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/jsx-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config/jsx/jsx-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config/jsx_import_source.out b/tests/specs/run/jsx_import_source_pragma_with_config/jsx_import_source.out
new file mode 100644
index 0000000000..b9555987a6
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config/jsx_import_source.out
@@ -0,0 +1,2 @@
+[WILDCARD]
+imported http://localhost:4545/jsx/jsx-runtime
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config/jsx_import_source_pragma.tsx b/tests/specs/run/jsx_import_source_pragma_with_config/jsx_import_source_pragma.tsx
new file mode 100644
index 0000000000..c19e53d4ff
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config/jsx_import_source_pragma.tsx
@@ -0,0 +1,9 @@
+/** @jsxImportSource http://localhost:4545/jsx */
+
+function A() {
+  return "hello";
+}
+
+export function B() {
+  return <A></A>;
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_no_check/__test__.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/__test__.jsonc
new file mode 100644
index 0000000000..3e8089fd2c
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --reload --config jsx/deno-jsx.jsonc --no-lock --no-check jsx_import_source_pragma.tsx",
+  "output": "jsx_import_source.out"
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsx-error.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsx-error.jsonc
new file mode 100644
index 0000000000..37cb4dd912
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsx-error.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "./nonexistent"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsx-import-map.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsx-import-map.jsonc
new file mode 100644
index 0000000000..5adbfa8b5a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsx-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsx-precompile-skip.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsx-precompile-skip.jsonc
new file mode 100644
index 0000000000..3c9e4fa1f8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsx-precompile-skip.jsonc
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile",
+    "jsxPrecompileSkipElements": ["a", "img"]
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsx-precompile.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsx-precompile.jsonc
new file mode 100644
index 0000000000..95ae1b9f31
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsx-precompile.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsx.json b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsx.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsx.jsonc
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsx.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsxdev-import-map.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsxdev-import-map.jsonc
new file mode 100644
index 0000000000..7481d5a2d8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsxdev-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsxdev.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsxdev.jsonc
new file mode 100644
index 0000000000..ae5bdf9f16
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno-jsxdev.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno.lock b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno.lock
new file mode 100644
index 0000000000..011e8fe108
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/jsx/jsx-dev-runtime/index.ts": "183c5bf1cfb82b15fc1e8cca15593d4816035759532d851abd4476df378c8412"
+  }
+}
\ No newline at end of file
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/import-map-scoped.json b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/import-map-scoped.json
new file mode 100644
index 0000000000..9b2005128f
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/import-map-scoped.json
@@ -0,0 +1,8 @@
+{
+  "scopes": {
+    "../subdir/": {
+      "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+      "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts"
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/import-map.json b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/import-map.json
new file mode 100644
index 0000000000..1bfa04e2f0
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/import-map.json
@@ -0,0 +1,7 @@
+{
+  "imports": {
+    "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+    "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts",
+    "jsx-precompile/jsx-runtime": "http://localhost:4545/jsx/jsx-precompile/index.ts"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/jsx-dev-runtime/index.ts b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/jsx-dev-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/jsx-dev-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/jsx-precompile/index.ts b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/jsx-precompile/index.ts
new file mode 100644
index 0000000000..0d56095e0b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/jsx-precompile/index.ts
@@ -0,0 +1,23 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+// deno-lint-ignore-file no-explicit-any
+export const jsxAttr = (name: string, value: any) => `${name}="${value}"`;
+// deno-lint-ignore-file no-explicit-any
+export const jsxTemplate = (_template: string[], ..._exprs: any[]) => "";
+// deno-lint-ignore-file no-explicit-any
+export const jsxEscape = (_value: any) => "";
+console.log("imported", import.meta.url);
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      [tagName: string]: Record<string, any>;
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/jsx-runtime/index.ts b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/jsx-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx/jsx-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx_import_source.out b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx_import_source.out
new file mode 100644
index 0000000000..b9555987a6
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx_import_source.out
@@ -0,0 +1,2 @@
+[WILDCARD]
+imported http://localhost:4545/jsx/jsx-runtime
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx_import_source_pragma.tsx b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx_import_source_pragma.tsx
new file mode 100644
index 0000000000..c19e53d4ff
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_no_check/jsx_import_source_pragma.tsx
@@ -0,0 +1,9 @@
+/** @jsxImportSource http://localhost:4545/jsx */
+
+function A() {
+  return "hello";
+}
+
+export function B() {
+  return <A></A>;
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/__test__.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/__test__.jsonc
new file mode 100644
index 0000000000..03ed1af1b6
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --reload --config jsx/deno-jsx.jsonc --no-lock --vendor jsx_import_source_pragma.tsx",
+  "output": "jsx_import_source.out"
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsx-error.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsx-error.jsonc
new file mode 100644
index 0000000000..37cb4dd912
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsx-error.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "./nonexistent"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsx-import-map.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsx-import-map.jsonc
new file mode 100644
index 0000000000..5adbfa8b5a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsx-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsx-precompile-skip.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsx-precompile-skip.jsonc
new file mode 100644
index 0000000000..3c9e4fa1f8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsx-precompile-skip.jsonc
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile",
+    "jsxPrecompileSkipElements": ["a", "img"]
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsx-precompile.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsx-precompile.jsonc
new file mode 100644
index 0000000000..95ae1b9f31
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsx-precompile.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsx.json b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsx.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsx.jsonc
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsx.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsxdev-import-map.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsxdev-import-map.jsonc
new file mode 100644
index 0000000000..7481d5a2d8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsxdev-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsxdev.jsonc b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsxdev.jsonc
new file mode 100644
index 0000000000..ae5bdf9f16
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno-jsxdev.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno.lock b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno.lock
new file mode 100644
index 0000000000..011e8fe108
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/jsx/jsx-dev-runtime/index.ts": "183c5bf1cfb82b15fc1e8cca15593d4816035759532d851abd4476df378c8412"
+  }
+}
\ No newline at end of file
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/import-map-scoped.json b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/import-map-scoped.json
new file mode 100644
index 0000000000..9b2005128f
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/import-map-scoped.json
@@ -0,0 +1,8 @@
+{
+  "scopes": {
+    "../subdir/": {
+      "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+      "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts"
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/import-map.json b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/import-map.json
new file mode 100644
index 0000000000..1bfa04e2f0
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/import-map.json
@@ -0,0 +1,7 @@
+{
+  "imports": {
+    "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+    "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts",
+    "jsx-precompile/jsx-runtime": "http://localhost:4545/jsx/jsx-precompile/index.ts"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/jsx-dev-runtime/index.ts b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/jsx-dev-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/jsx-dev-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/jsx-precompile/index.ts b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/jsx-precompile/index.ts
new file mode 100644
index 0000000000..0d56095e0b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/jsx-precompile/index.ts
@@ -0,0 +1,23 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+// deno-lint-ignore-file no-explicit-any
+export const jsxAttr = (name: string, value: any) => `${name}="${value}"`;
+// deno-lint-ignore-file no-explicit-any
+export const jsxTemplate = (_template: string[], ..._exprs: any[]) => "";
+// deno-lint-ignore-file no-explicit-any
+export const jsxEscape = (_value: any) => "";
+console.log("imported", import.meta.url);
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      [tagName: string]: Record<string, any>;
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/jsx-runtime/index.ts b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/jsx-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/jsx-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/vendor/http_localhost_4545/jsx/#jsx-runtime_62ac8.js b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/vendor/http_localhost_4545/jsx/#jsx-runtime_62ac8.js
new file mode 100644
index 0000000000..c8f0a908db
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/vendor/http_localhost_4545/jsx/#jsx-runtime_62ac8.js
@@ -0,0 +1,11 @@
+export function jsx(
+  _type,
+  _props,
+  _key,
+  _source,
+  _self,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/vendor/manifest.json b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/vendor/manifest.json
new file mode 100644
index 0000000000..a770c33669
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx/vendor/manifest.json
@@ -0,0 +1,9 @@
+{
+  "modules": {
+    "http://localhost:4545/jsx/jsx-runtime": {
+      "headers": {
+        "content-type": "application/javascript"
+      }
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx_import_source.out b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx_import_source.out
new file mode 100644
index 0000000000..b9555987a6
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx_import_source.out
@@ -0,0 +1,2 @@
+[WILDCARD]
+imported http://localhost:4545/jsx/jsx-runtime
diff --git a/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx_import_source_pragma.tsx b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx_import_source_pragma.tsx
new file mode 100644
index 0000000000..c19e53d4ff
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_config_vendor_dir/jsx_import_source_pragma.tsx
@@ -0,0 +1,9 @@
+/** @jsxImportSource http://localhost:4545/jsx */
+
+function A() {
+  return "hello";
+}
+
+export function B() {
+  return <A></A>;
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_dev_config/__test__.jsonc b/tests/specs/run/jsx_import_source_pragma_with_dev_config/__test__.jsonc
new file mode 100644
index 0000000000..56734e4678
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_dev_config/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload --allow-import --config jsx/deno-jsxdev.jsonc --no-lock jsx_import_source_pragma.tsx",
+  "output": "jsx_import_source_dev.out"
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsx-error.jsonc b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsx-error.jsonc
new file mode 100644
index 0000000000..37cb4dd912
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsx-error.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "./nonexistent"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsx-import-map.jsonc b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsx-import-map.jsonc
new file mode 100644
index 0000000000..5adbfa8b5a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsx-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsx-precompile-skip.jsonc b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsx-precompile-skip.jsonc
new file mode 100644
index 0000000000..3c9e4fa1f8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsx-precompile-skip.jsonc
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile",
+    "jsxPrecompileSkipElements": ["a", "img"]
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsx-precompile.jsonc b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsx-precompile.jsonc
new file mode 100644
index 0000000000..95ae1b9f31
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsx-precompile.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsx.json b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsx.jsonc b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsx.jsonc
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsx.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsxdev-import-map.jsonc b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsxdev-import-map.jsonc
new file mode 100644
index 0000000000..7481d5a2d8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsxdev-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsxdev.jsonc b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsxdev.jsonc
new file mode 100644
index 0000000000..ae5bdf9f16
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno-jsxdev.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno.lock b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno.lock
new file mode 100644
index 0000000000..011e8fe108
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/jsx/jsx-dev-runtime/index.ts": "183c5bf1cfb82b15fc1e8cca15593d4816035759532d851abd4476df378c8412"
+  }
+}
\ No newline at end of file
diff --git a/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/import-map-scoped.json b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/import-map-scoped.json
new file mode 100644
index 0000000000..9b2005128f
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/import-map-scoped.json
@@ -0,0 +1,8 @@
+{
+  "scopes": {
+    "../subdir/": {
+      "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+      "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts"
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/import-map.json b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/import-map.json
new file mode 100644
index 0000000000..1bfa04e2f0
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/import-map.json
@@ -0,0 +1,7 @@
+{
+  "imports": {
+    "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+    "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts",
+    "jsx-precompile/jsx-runtime": "http://localhost:4545/jsx/jsx-precompile/index.ts"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/jsx-dev-runtime/index.ts b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/jsx-dev-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/jsx-dev-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/jsx-precompile/index.ts b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/jsx-precompile/index.ts
new file mode 100644
index 0000000000..0d56095e0b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/jsx-precompile/index.ts
@@ -0,0 +1,23 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+// deno-lint-ignore-file no-explicit-any
+export const jsxAttr = (name: string, value: any) => `${name}="${value}"`;
+// deno-lint-ignore-file no-explicit-any
+export const jsxTemplate = (_template: string[], ..._exprs: any[]) => "";
+// deno-lint-ignore-file no-explicit-any
+export const jsxEscape = (_value: any) => "";
+console.log("imported", import.meta.url);
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      [tagName: string]: Record<string, any>;
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/jsx-runtime/index.ts b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/jsx-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx/jsx-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx_import_source_dev.out b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx_import_source_dev.out
new file mode 100644
index 0000000000..38d7a12f05
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx_import_source_dev.out
@@ -0,0 +1,2 @@
+[WILDCARD]
+imported http://localhost:4545/jsx/jsx-dev-runtime
diff --git a/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx_import_source_pragma.tsx b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx_import_source_pragma.tsx
new file mode 100644
index 0000000000..c19e53d4ff
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_pragma_with_dev_config/jsx_import_source_pragma.tsx
@@ -0,0 +1,9 @@
+/** @jsxImportSource http://localhost:4545/jsx */
+
+function A() {
+  return "hello";
+}
+
+export function B() {
+  return <A></A>;
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map/__test__.jsonc b/tests/specs/run/jsx_import_source_precompile_import_map/__test__.jsonc
new file mode 100644
index 0000000000..c795a9d8e6
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --reload --check --import-map jsx/import-map.json --no-lock --config jsx/deno-jsx-precompile.jsonc jsx_precompile/no_pragma.tsx",
+  "output": "jsx_precompile/no_pragma.out"
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsx-error.jsonc b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsx-error.jsonc
new file mode 100644
index 0000000000..37cb4dd912
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsx-error.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "./nonexistent"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsx-import-map.jsonc b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsx-import-map.jsonc
new file mode 100644
index 0000000000..5adbfa8b5a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsx-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsx-precompile-skip.jsonc b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsx-precompile-skip.jsonc
new file mode 100644
index 0000000000..3c9e4fa1f8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsx-precompile-skip.jsonc
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile",
+    "jsxPrecompileSkipElements": ["a", "img"]
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsx-precompile.jsonc b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsx-precompile.jsonc
new file mode 100644
index 0000000000..95ae1b9f31
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsx-precompile.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsx.json b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsx.jsonc b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsx.jsonc
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsx.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsxdev-import-map.jsonc b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsxdev-import-map.jsonc
new file mode 100644
index 0000000000..7481d5a2d8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsxdev-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsxdev.jsonc b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsxdev.jsonc
new file mode 100644
index 0000000000..ae5bdf9f16
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno-jsxdev.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno.lock b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno.lock
new file mode 100644
index 0000000000..011e8fe108
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/jsx/jsx-dev-runtime/index.ts": "183c5bf1cfb82b15fc1e8cca15593d4816035759532d851abd4476df378c8412"
+  }
+}
\ No newline at end of file
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map/jsx/import-map-scoped.json b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/import-map-scoped.json
new file mode 100644
index 0000000000..9b2005128f
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/import-map-scoped.json
@@ -0,0 +1,8 @@
+{
+  "scopes": {
+    "../subdir/": {
+      "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+      "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts"
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map/jsx/import-map.json b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/import-map.json
new file mode 100644
index 0000000000..1bfa04e2f0
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/import-map.json
@@ -0,0 +1,7 @@
+{
+  "imports": {
+    "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+    "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts",
+    "jsx-precompile/jsx-runtime": "http://localhost:4545/jsx/jsx-precompile/index.ts"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map/jsx/jsx-dev-runtime/index.ts b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/jsx-dev-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/jsx-dev-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map/jsx/jsx-precompile/index.ts b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/jsx-precompile/index.ts
new file mode 100644
index 0000000000..0d56095e0b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/jsx-precompile/index.ts
@@ -0,0 +1,23 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+// deno-lint-ignore-file no-explicit-any
+export const jsxAttr = (name: string, value: any) => `${name}="${value}"`;
+// deno-lint-ignore-file no-explicit-any
+export const jsxTemplate = (_template: string[], ..._exprs: any[]) => "";
+// deno-lint-ignore-file no-explicit-any
+export const jsxEscape = (_value: any) => "";
+console.log("imported", import.meta.url);
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      [tagName: string]: Record<string, any>;
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map/jsx/jsx-runtime/index.ts b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/jsx-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map/jsx/jsx-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/testdata/run/jsx_precompile/no_pragma.out b/tests/specs/run/jsx_import_source_precompile_import_map/jsx_precompile/no_pragma.out
similarity index 67%
rename from tests/testdata/run/jsx_precompile/no_pragma.out
rename to tests/specs/run/jsx_import_source_precompile_import_map/jsx_precompile/no_pragma.out
index 4379959230..f26984258c 100644
--- a/tests/testdata/run/jsx_precompile/no_pragma.out
+++ b/tests/specs/run/jsx_import_source_precompile_import_map/jsx_precompile/no_pragma.out
@@ -1,3 +1,3 @@
 Download http://localhost:4545/jsx/jsx-precompile/index.ts
-Check file:///[WILDCARD]/run/jsx_precompile/no_pragma.tsx
+Check file:///[WILDCARD]/jsx_precompile/no_pragma.tsx
 imported http://localhost:4545/jsx/jsx-precompile/index.ts
diff --git a/tests/testdata/run/jsx_precompile/no_pragma.tsx b/tests/specs/run/jsx_import_source_precompile_import_map/jsx_precompile/no_pragma.tsx
similarity index 100%
rename from tests/testdata/run/jsx_precompile/no_pragma.tsx
rename to tests/specs/run/jsx_import_source_precompile_import_map/jsx_precompile/no_pragma.tsx
diff --git a/tests/testdata/run/jsx_precompile/skip.out b/tests/specs/run/jsx_import_source_precompile_import_map/jsx_precompile/skip.out
similarity index 100%
rename from tests/testdata/run/jsx_precompile/skip.out
rename to tests/specs/run/jsx_import_source_precompile_import_map/jsx_precompile/skip.out
diff --git a/tests/testdata/run/jsx_precompile/skip.tsx b/tests/specs/run/jsx_import_source_precompile_import_map/jsx_precompile/skip.tsx
similarity index 100%
rename from tests/testdata/run/jsx_precompile/skip.tsx
rename to tests/specs/run/jsx_import_source_precompile_import_map/jsx_precompile/skip.tsx
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/__test__.jsonc b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/__test__.jsonc
new file mode 100644
index 0000000000..7163c83d00
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --reload --check --import-map jsx/import-map.json --no-lock --config jsx/deno-jsx-precompile-skip.jsonc jsx_precompile/skip.tsx",
+  "output": "jsx_precompile/skip.out"
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsx-error.jsonc b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsx-error.jsonc
new file mode 100644
index 0000000000..37cb4dd912
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsx-error.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "./nonexistent"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsx-import-map.jsonc b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsx-import-map.jsonc
new file mode 100644
index 0000000000..5adbfa8b5a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsx-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsx-precompile-skip.jsonc b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsx-precompile-skip.jsonc
new file mode 100644
index 0000000000..3c9e4fa1f8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsx-precompile-skip.jsonc
@@ -0,0 +1,7 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile",
+    "jsxPrecompileSkipElements": ["a", "img"]
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsx-precompile.jsonc b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsx-precompile.jsonc
new file mode 100644
index 0000000000..95ae1b9f31
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsx-precompile.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "precompile",
+    "jsxImportSource": "jsx-precompile"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsx.json b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsx.json
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsx.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsx.jsonc b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsx.jsonc
new file mode 100644
index 0000000000..311409ea37
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsx.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsxdev-import-map.jsonc b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsxdev-import-map.jsonc
new file mode 100644
index 0000000000..7481d5a2d8
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsxdev-import-map.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsxdev.jsonc b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsxdev.jsonc
new file mode 100644
index 0000000000..ae5bdf9f16
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno-jsxdev.jsonc
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsxdev",
+    "jsxImportSource": "http://localhost:4545/jsx"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno.lock b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno.lock
new file mode 100644
index 0000000000..011e8fe108
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/deno.lock
@@ -0,0 +1,6 @@
+{
+  "version": "2",
+  "remote": {
+    "http://localhost:4545/jsx/jsx-dev-runtime/index.ts": "183c5bf1cfb82b15fc1e8cca15593d4816035759532d851abd4476df378c8412"
+  }
+}
\ No newline at end of file
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/import-map-scoped.json b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/import-map-scoped.json
new file mode 100644
index 0000000000..9b2005128f
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/import-map-scoped.json
@@ -0,0 +1,8 @@
+{
+  "scopes": {
+    "../subdir/": {
+      "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+      "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts"
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/import-map.json b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/import-map.json
new file mode 100644
index 0000000000..1bfa04e2f0
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/import-map.json
@@ -0,0 +1,7 @@
+{
+  "imports": {
+    "jsx/jsx-runtime": "http://localhost:4545/jsx/jsx-runtime/index.ts",
+    "jsx/jsx-dev-runtime": "http://localhost:4545/jsx/jsx-dev-runtime/index.ts",
+    "jsx-precompile/jsx-runtime": "http://localhost:4545/jsx/jsx-precompile/index.ts"
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/jsx-dev-runtime/index.ts b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/jsx-dev-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/jsx-dev-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/jsx-precompile/index.ts b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/jsx-precompile/index.ts
new file mode 100644
index 0000000000..0d56095e0b
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/jsx-precompile/index.ts
@@ -0,0 +1,23 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+// deno-lint-ignore-file no-explicit-any
+export const jsxAttr = (name: string, value: any) => `${name}="${value}"`;
+// deno-lint-ignore-file no-explicit-any
+export const jsxTemplate = (_template: string[], ..._exprs: any[]) => "";
+// deno-lint-ignore-file no-explicit-any
+export const jsxEscape = (_value: any) => "";
+console.log("imported", import.meta.url);
+
+declare global {
+  namespace JSX {
+    interface IntrinsicElements {
+      [tagName: string]: Record<string, any>;
+    }
+  }
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/jsx-runtime/index.ts b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/jsx-runtime/index.ts
new file mode 100644
index 0000000000..15e2029c8a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx/jsx-runtime/index.ts
@@ -0,0 +1,12 @@
+// deno-lint-ignore-file no-explicit-any
+export function jsx(
+  _type: any,
+  _props: any,
+  _key: any,
+  _source: any,
+  _self: any,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx_precompile/no_pragma.out b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx_precompile/no_pragma.out
new file mode 100644
index 0000000000..f26984258c
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx_precompile/no_pragma.out
@@ -0,0 +1,3 @@
+Download http://localhost:4545/jsx/jsx-precompile/index.ts
+Check file:///[WILDCARD]/jsx_precompile/no_pragma.tsx
+imported http://localhost:4545/jsx/jsx-precompile/index.ts
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx_precompile/no_pragma.tsx b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx_precompile/no_pragma.tsx
new file mode 100644
index 0000000000..7ba21d80d2
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx_precompile/no_pragma.tsx
@@ -0,0 +1,3 @@
+export function A() {
+  return <h1>hello</h1>;
+}
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx_precompile/skip.out b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx_precompile/skip.out
new file mode 100644
index 0000000000..6696c550ca
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx_precompile/skip.out
@@ -0,0 +1,3 @@
+Download http://localhost:4545/jsx/jsx-precompile/index.ts
+Check file:///[WILDCARD]/jsx_precompile/skip.tsx
+imported http://localhost:4545/jsx/jsx-precompile/index.ts
diff --git a/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx_precompile/skip.tsx b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx_precompile/skip.tsx
new file mode 100644
index 0000000000..49bc4e2b7a
--- /dev/null
+++ b/tests/specs/run/jsx_import_source_precompile_import_map_skip_element/jsx_precompile/skip.tsx
@@ -0,0 +1,9 @@
+export function A() {
+  return (
+    <div>
+      <a href="#">foo</a>
+      <p>hello</p>
+      <img src="#" alt="" />
+    </div>
+  );
+}
diff --git a/tests/specs/run/ld_preload/env_arg.out b/tests/specs/run/ld_preload/env_arg.out
index 945737e65b..d87a1115c6 100644
--- a/tests/specs/run/ld_preload/env_arg.out
+++ b/tests/specs/run/ld_preload/env_arg.out
@@ -1,8 +1,8 @@
-NotCapable: Requires --allow-all permissions to spawn subprocess with LD_PRELOAD environment variable.
+NotCapable: Requires --allow-run permissions to spawn subprocess with LD_PRELOAD environment variable. Alternatively, spawn with the environment variable unset.
     [WILDCARD]
   name: "NotCapable"
 }
-NotCapable: Requires --allow-all permissions to spawn subprocess with LD_PRELOAD environment variable.
+NotCapable: Requires --allow-run permissions to spawn subprocess with LD_PRELOAD environment variable. Alternatively, spawn with the environment variable unset.
     [WILDCARD]
   name: "NotCapable"
 }
diff --git a/tests/specs/run/ld_preload/env_arg.ts b/tests/specs/run/ld_preload/env_arg.ts
index d7ca1073df..fe043d56dc 100644
--- a/tests/specs/run/ld_preload/env_arg.ts
+++ b/tests/specs/run/ld_preload/env_arg.ts
@@ -1,5 +1,5 @@
 try {
-  new Deno.Command("echo", {
+  new Deno.Command("curl", {
     env: {
       "LD_PRELOAD": "./libpreload.so",
     },
@@ -10,7 +10,7 @@ try {
 
 try {
   Deno.run({
-    cmd: ["echo"],
+    cmd: ["curl"],
     env: {
       "LD_PRELOAD": "./libpreload.so",
     },
diff --git a/tests/specs/run/ld_preload/set_with_allow_env.out b/tests/specs/run/ld_preload/set_with_allow_env.out
index f89582d6c8..570515fc00 100644
--- a/tests/specs/run/ld_preload/set_with_allow_env.out
+++ b/tests/specs/run/ld_preload/set_with_allow_env.out
@@ -1,8 +1,8 @@
-NotCapable: Requires --allow-all permissions to spawn subprocess with LD_PRELOAD environment variable.
+NotCapable: Requires --allow-run permissions to spawn subprocess with LD_PRELOAD environment variable. Alternatively, spawn with the environment variable unset.
   [WILDCARD]
   name: "NotCapable"
 }
-NotCapable: Requires --allow-all permissions to spawn subprocess with DYLD_FALLBACK_LIBRARY_PATH, LD_PRELOAD environment variables.
+NotCapable: Requires --allow-run permissions to spawn subprocess with DYLD_FALLBACK_LIBRARY_PATH, LD_PRELOAD environment variables. Alternatively, spawn with these environment variables unset.
   [WILDCARD]
   name: "NotCapable"
 }
diff --git a/tests/specs/run/lock_check_ok/003_relative_import.ts b/tests/specs/run/lock_check_ok/003_relative_import.ts
new file mode 100644
index 0000000000..d392f4a5d1
--- /dev/null
+++ b/tests/specs/run/lock_check_ok/003_relative_import.ts
@@ -0,0 +1,3 @@
+import { printHello } from "./print_hello.ts";
+
+printHello();
diff --git a/tests/specs/run/lock_check_ok/003_relative_import.ts.out b/tests/specs/run/lock_check_ok/003_relative_import.ts.out
new file mode 100644
index 0000000000..e965047ad7
--- /dev/null
+++ b/tests/specs/run/lock_check_ok/003_relative_import.ts.out
@@ -0,0 +1 @@
+Hello
diff --git a/tests/specs/run/lock_check_ok/__test__.jsonc b/tests/specs/run/lock_check_ok/__test__.jsonc
new file mode 100644
index 0000000000..e8ce4572e4
--- /dev/null
+++ b/tests/specs/run/lock_check_ok/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --allow-import --lock=lock_check_ok.json 003_relative_import.ts",
+  "output": "003_relative_import.ts.out"
+}
diff --git a/tests/specs/run/lock_check_ok/lock_check_ok.json b/tests/specs/run/lock_check_ok/lock_check_ok.json
new file mode 100644
index 0000000000..20f7e20005
--- /dev/null
+++ b/tests/specs/run/lock_check_ok/lock_check_ok.json
@@ -0,0 +1,4 @@
+{
+  "http://127.0.0.1:4545/print_hello.ts": "fa6692c8f9ff3fb107e773c3ece5274e9d08be282867a1e3ded1d9c00fcaa63c",
+  "http://127.0.0.1:4545/003_relative_import.ts": "a1572e8fd2c2712b33f04aed2561505b5feb2c8696f1f2cded3de7127931b97e"
+}
diff --git a/tests/specs/run/lock_check_ok/print_hello.ts b/tests/specs/run/lock_check_ok/print_hello.ts
new file mode 100644
index 0000000000..b9c0ad5275
--- /dev/null
+++ b/tests/specs/run/lock_check_ok/print_hello.ts
@@ -0,0 +1,3 @@
+export function printHello() {
+  console.log("Hello");
+}
diff --git a/tests/specs/run/lock_check_ok2/019_media_types.ts b/tests/specs/run/lock_check_ok2/019_media_types.ts
new file mode 100644
index 0000000000..d985bd2496
--- /dev/null
+++ b/tests/specs/run/lock_check_ok2/019_media_types.ts
@@ -0,0 +1,24 @@
+// When run against the test HTTP server, it will serve different media types
+// based on the URL containing `.t#.` strings, which exercises the different
+// mapping of media types end to end.
+
+import { loaded as loadedTs1 } from "http://localhost:4545/subdir/mt_text_typescript.t1.ts";
+import { loaded as loadedTs2 } from "http://localhost:4545/subdir/mt_video_vdn.t2.ts";
+import { loaded as loadedTs3 } from "http://localhost:4545/subdir/mt_video_mp2t.t3.ts";
+import { loaded as loadedTs4 } from "http://localhost:4545/subdir/mt_application_x_typescript.t4.ts";
+import { loaded as loadedJs1 } from "http://localhost:4545/subdir/mt_text_javascript.j1.js";
+import { loaded as loadedJs2 } from "http://localhost:4545/subdir/mt_application_ecmascript.j2.js";
+import { loaded as loadedJs3 } from "http://localhost:4545/subdir/mt_text_ecmascript.j3.js";
+import { loaded as loadedJs4 } from "http://localhost:4545/subdir/mt_application_x_javascript.j4.js";
+
+console.log(
+  "success",
+  loadedTs1,
+  loadedTs2,
+  loadedTs3,
+  loadedTs4,
+  loadedJs1,
+  loadedJs2,
+  loadedJs3,
+  loadedJs4,
+);
diff --git a/tests/specs/run/lock_check_ok2/019_media_types.ts.out b/tests/specs/run/lock_check_ok2/019_media_types.ts.out
new file mode 100644
index 0000000000..b3e94678c5
--- /dev/null
+++ b/tests/specs/run/lock_check_ok2/019_media_types.ts.out
@@ -0,0 +1 @@
+[WILDCARD]success true true true true true true true true
diff --git a/tests/specs/run/lock_check_ok2/__test__.jsonc b/tests/specs/run/lock_check_ok2/__test__.jsonc
new file mode 100644
index 0000000000..dc790528a2
--- /dev/null
+++ b/tests/specs/run/lock_check_ok2/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --lock=lock_check_ok2.json 019_media_types.ts",
+  "output": "019_media_types.ts.out"
+}
diff --git a/tests/testdata/run/lock_check_ok2.json b/tests/specs/run/lock_check_ok2/lock_check_ok2.json
similarity index 100%
rename from tests/testdata/run/lock_check_ok2.json
rename to tests/specs/run/lock_check_ok2/lock_check_ok2.json
diff --git a/tests/specs/run/lock_v2_check_ok/003_relative_import.ts b/tests/specs/run/lock_v2_check_ok/003_relative_import.ts
new file mode 100644
index 0000000000..d392f4a5d1
--- /dev/null
+++ b/tests/specs/run/lock_v2_check_ok/003_relative_import.ts
@@ -0,0 +1,3 @@
+import { printHello } from "./print_hello.ts";
+
+printHello();
diff --git a/tests/specs/run/lock_v2_check_ok/003_relative_import.ts.out b/tests/specs/run/lock_v2_check_ok/003_relative_import.ts.out
new file mode 100644
index 0000000000..e965047ad7
--- /dev/null
+++ b/tests/specs/run/lock_v2_check_ok/003_relative_import.ts.out
@@ -0,0 +1 @@
+Hello
diff --git a/tests/specs/run/lock_v2_check_ok/__test__.jsonc b/tests/specs/run/lock_v2_check_ok/__test__.jsonc
new file mode 100644
index 0000000000..d7b819d569
--- /dev/null
+++ b/tests/specs/run/lock_v2_check_ok/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --quiet --lock=lock_v2_check_ok.json 003_relative_import.ts",
+  "output": "003_relative_import.ts.out"
+}
diff --git a/tests/specs/run/lock_v2_check_ok/lock_v2_check_ok.json b/tests/specs/run/lock_v2_check_ok/lock_v2_check_ok.json
new file mode 100644
index 0000000000..47a761fbdb
--- /dev/null
+++ b/tests/specs/run/lock_v2_check_ok/lock_v2_check_ok.json
@@ -0,0 +1,7 @@
+{
+  "version": "2",
+  "remote": {
+    "http://127.0.0.1:4545/print_hello.ts": "fa6692c8f9ff3fb107e773c3ece5274e9d08be282867a1e3ded1d9c00fcaa63c",
+    "http://127.0.0.1:4545/003_relative_import.ts": "a1572e8fd2c2712b33f04aed2561505b5feb2c8696f1f2cded3de7127931b97e"
+  }
+}
diff --git a/tests/specs/run/lock_v2_check_ok/print_hello.ts b/tests/specs/run/lock_v2_check_ok/print_hello.ts
new file mode 100644
index 0000000000..b9c0ad5275
--- /dev/null
+++ b/tests/specs/run/lock_v2_check_ok/print_hello.ts
@@ -0,0 +1,3 @@
+export function printHello() {
+  console.log("Hello");
+}
diff --git a/tests/specs/run/lock_v2_check_ok2/019_media_types.ts b/tests/specs/run/lock_v2_check_ok2/019_media_types.ts
new file mode 100644
index 0000000000..d985bd2496
--- /dev/null
+++ b/tests/specs/run/lock_v2_check_ok2/019_media_types.ts
@@ -0,0 +1,24 @@
+// When run against the test HTTP server, it will serve different media types
+// based on the URL containing `.t#.` strings, which exercises the different
+// mapping of media types end to end.
+
+import { loaded as loadedTs1 } from "http://localhost:4545/subdir/mt_text_typescript.t1.ts";
+import { loaded as loadedTs2 } from "http://localhost:4545/subdir/mt_video_vdn.t2.ts";
+import { loaded as loadedTs3 } from "http://localhost:4545/subdir/mt_video_mp2t.t3.ts";
+import { loaded as loadedTs4 } from "http://localhost:4545/subdir/mt_application_x_typescript.t4.ts";
+import { loaded as loadedJs1 } from "http://localhost:4545/subdir/mt_text_javascript.j1.js";
+import { loaded as loadedJs2 } from "http://localhost:4545/subdir/mt_application_ecmascript.j2.js";
+import { loaded as loadedJs3 } from "http://localhost:4545/subdir/mt_text_ecmascript.j3.js";
+import { loaded as loadedJs4 } from "http://localhost:4545/subdir/mt_application_x_javascript.j4.js";
+
+console.log(
+  "success",
+  loadedTs1,
+  loadedTs2,
+  loadedTs3,
+  loadedTs4,
+  loadedJs1,
+  loadedJs2,
+  loadedJs3,
+  loadedJs4,
+);
diff --git a/tests/specs/run/lock_v2_check_ok2/019_media_types.ts.out b/tests/specs/run/lock_v2_check_ok2/019_media_types.ts.out
new file mode 100644
index 0000000000..b3e94678c5
--- /dev/null
+++ b/tests/specs/run/lock_v2_check_ok2/019_media_types.ts.out
@@ -0,0 +1 @@
+[WILDCARD]success true true true true true true true true
diff --git a/tests/specs/run/lock_v2_check_ok2/__test__.jsonc b/tests/specs/run/lock_v2_check_ok2/__test__.jsonc
new file mode 100644
index 0000000000..a9430b4bcd
--- /dev/null
+++ b/tests/specs/run/lock_v2_check_ok2/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --lock=lock_v2_check_ok2.json 019_media_types.ts",
+  "output": "019_media_types.ts.out"
+}
diff --git a/tests/testdata/run/lock_v2_check_ok2.json b/tests/specs/run/lock_v2_check_ok2/lock_v2_check_ok2.json
similarity index 100%
rename from tests/testdata/run/lock_v2_check_ok2.json
rename to tests/specs/run/lock_v2_check_ok2/lock_v2_check_ok2.json
diff --git a/tests/specs/run/long_data_url_formatting/__test__.jsonc b/tests/specs/run/long_data_url_formatting/__test__.jsonc
new file mode 100644
index 0000000000..f7ae56c635
--- /dev/null
+++ b/tests/specs/run/long_data_url_formatting/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run long_data_url_formatting.ts",
+  "output": "long_data_url_formatting.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/long_data_url_formatting.ts b/tests/specs/run/long_data_url_formatting/long_data_url_formatting.ts
similarity index 100%
rename from tests/testdata/run/long_data_url_formatting.ts
rename to tests/specs/run/long_data_url_formatting/long_data_url_formatting.ts
diff --git a/tests/testdata/run/long_data_url_formatting.ts.out b/tests/specs/run/long_data_url_formatting/long_data_url_formatting.ts.out
similarity index 100%
rename from tests/testdata/run/long_data_url_formatting.ts.out
rename to tests/specs/run/long_data_url_formatting/long_data_url_formatting.ts.out
diff --git a/tests/specs/run/main_module/__test__.jsonc b/tests/specs/run/main_module/__test__.jsonc
new file mode 100644
index 0000000000..0d70eddbd9
--- /dev/null
+++ b/tests/specs/run/main_module/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload main_module/main.ts",
+  "output": "main_module/main.out"
+}
diff --git a/tests/testdata/run/main_module/main.out b/tests/specs/run/main_module/main_module/main.out
similarity index 100%
rename from tests/testdata/run/main_module/main.out
rename to tests/specs/run/main_module/main_module/main.out
diff --git a/tests/testdata/run/main_module/main.ts b/tests/specs/run/main_module/main_module/main.ts
similarity index 100%
rename from tests/testdata/run/main_module/main.ts
rename to tests/specs/run/main_module/main_module/main.ts
diff --git a/tests/testdata/run/main_module/other.ts b/tests/specs/run/main_module/main_module/other.ts
similarity index 100%
rename from tests/testdata/run/main_module/other.ts
rename to tests/specs/run/main_module/main_module/other.ts
diff --git a/tests/specs/run/mts_dmts_mjs/__test__.jsonc b/tests/specs/run/mts_dmts_mjs/__test__.jsonc
new file mode 100644
index 0000000000..b50bb4b19b
--- /dev/null
+++ b/tests/specs/run/mts_dmts_mjs/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run import.mts",
+  "output": "mts_dmts_mjs.out"
+}
diff --git a/tests/specs/run/mts_dmts_mjs/import.mts b/tests/specs/run/mts_dmts_mjs/import.mts
new file mode 100644
index 0000000000..eeb200f598
--- /dev/null
+++ b/tests/specs/run/mts_dmts_mjs/import.mts
@@ -0,0 +1,4 @@
+import * as a from "./mod.mjs";
+import { type A } from "./types.d.mts";
+
+console.log(a.a as A);
diff --git a/tests/specs/run/mts_dmts_mjs/mod.mjs b/tests/specs/run/mts_dmts_mjs/mod.mjs
new file mode 100644
index 0000000000..9233cce2f0
--- /dev/null
+++ b/tests/specs/run/mts_dmts_mjs/mod.mjs
@@ -0,0 +1 @@
+export const a = "a";
diff --git a/tests/testdata/run/mts_dmts_mjs.out b/tests/specs/run/mts_dmts_mjs/mts_dmts_mjs.out
similarity index 100%
rename from tests/testdata/run/mts_dmts_mjs.out
rename to tests/specs/run/mts_dmts_mjs/mts_dmts_mjs.out
diff --git a/tests/specs/run/mts_dmts_mjs/types.d.mts b/tests/specs/run/mts_dmts_mjs/types.d.mts
new file mode 100644
index 0000000000..28c2821466
--- /dev/null
+++ b/tests/specs/run/mts_dmts_mjs/types.d.mts
@@ -0,0 +1 @@
+export type A = "a";
diff --git a/tests/specs/run/mts_dmts_mjs_no_check/__test__.jsonc b/tests/specs/run/mts_dmts_mjs_no_check/__test__.jsonc
new file mode 100644
index 0000000000..0d36517bc1
--- /dev/null
+++ b/tests/specs/run/mts_dmts_mjs_no_check/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --no-check import.mts",
+  "output": "mts_dmts_mjs.out"
+}
diff --git a/tests/specs/run/mts_dmts_mjs_no_check/import.mts b/tests/specs/run/mts_dmts_mjs_no_check/import.mts
new file mode 100644
index 0000000000..eeb200f598
--- /dev/null
+++ b/tests/specs/run/mts_dmts_mjs_no_check/import.mts
@@ -0,0 +1,4 @@
+import * as a from "./mod.mjs";
+import { type A } from "./types.d.mts";
+
+console.log(a.a as A);
diff --git a/tests/specs/run/mts_dmts_mjs_no_check/mod.mjs b/tests/specs/run/mts_dmts_mjs_no_check/mod.mjs
new file mode 100644
index 0000000000..9233cce2f0
--- /dev/null
+++ b/tests/specs/run/mts_dmts_mjs_no_check/mod.mjs
@@ -0,0 +1 @@
+export const a = "a";
diff --git a/tests/specs/run/mts_dmts_mjs_no_check/mts_dmts_mjs.out b/tests/specs/run/mts_dmts_mjs_no_check/mts_dmts_mjs.out
new file mode 100644
index 0000000000..7898192261
--- /dev/null
+++ b/tests/specs/run/mts_dmts_mjs_no_check/mts_dmts_mjs.out
@@ -0,0 +1 @@
+a
diff --git a/tests/specs/run/mts_dmts_mjs_no_check/types.d.mts b/tests/specs/run/mts_dmts_mjs_no_check/types.d.mts
new file mode 100644
index 0000000000..28c2821466
--- /dev/null
+++ b/tests/specs/run/mts_dmts_mjs_no_check/types.d.mts
@@ -0,0 +1 @@
+export type A = "a";
diff --git a/tests/specs/run/nested_error/__test__.jsonc b/tests/specs/run/nested_error/__test__.jsonc
new file mode 100644
index 0000000000..d167832bae
--- /dev/null
+++ b/tests/specs/run/nested_error/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run nested_error/main.ts",
+  "output": "nested_error/main.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/nested_error/main.ts b/tests/specs/run/nested_error/nested_error/main.ts
similarity index 100%
rename from tests/testdata/run/nested_error/main.ts
rename to tests/specs/run/nested_error/nested_error/main.ts
diff --git a/tests/testdata/run/nested_error/main.ts.out b/tests/specs/run/nested_error/nested_error/main.ts.out
similarity index 100%
rename from tests/testdata/run/nested_error/main.ts.out
rename to tests/specs/run/nested_error/nested_error/main.ts.out
diff --git a/tests/specs/run/no_check/006_url_imports.ts b/tests/specs/run/no_check/006_url_imports.ts
new file mode 100644
index 0000000000..ad2d259156
--- /dev/null
+++ b/tests/specs/run/no_check/006_url_imports.ts
@@ -0,0 +1,3 @@
+import { printHello } from "./mod2.ts";
+printHello();
+console.log("success");
diff --git a/tests/specs/run/no_check/006_url_imports.ts.out b/tests/specs/run/no_check/006_url_imports.ts.out
new file mode 100644
index 0000000000..989ce33e93
--- /dev/null
+++ b/tests/specs/run/no_check/006_url_imports.ts.out
@@ -0,0 +1,2 @@
+Hello
+success
diff --git a/tests/specs/run/no_check/__test__.jsonc b/tests/specs/run/no_check/__test__.jsonc
new file mode 100644
index 0000000000..696e08e2ad
--- /dev/null
+++ b/tests/specs/run/no_check/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --quiet --reload --no-check 006_url_imports.ts",
+  "output": "006_url_imports.ts.out"
+}
diff --git a/tests/specs/run/no_check/mod2.ts b/tests/specs/run/no_check/mod2.ts
new file mode 100644
index 0000000000..ce1adc0e81
--- /dev/null
+++ b/tests/specs/run/no_check/mod2.ts
@@ -0,0 +1 @@
+export { printHello } from "./print_hello.ts";
diff --git a/tests/specs/run/no_check/print_hello.ts b/tests/specs/run/no_check/print_hello.ts
new file mode 100644
index 0000000000..b9c0ad5275
--- /dev/null
+++ b/tests/specs/run/no_check/print_hello.ts
@@ -0,0 +1,3 @@
+export function printHello() {
+  console.log("Hello");
+}
diff --git a/tests/specs/run/no_check_decorators/__test__.jsonc b/tests/specs/run/no_check_decorators/__test__.jsonc
new file mode 100644
index 0000000000..da50d30a05
--- /dev/null
+++ b/tests/specs/run/no_check_decorators/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --no-check decorators/experimental/no_check/main.ts",
+  "output": "decorators/experimental/no_check/main.out"
+}
diff --git a/tests/specs/run/no_check_decorators/decorators/experimental/deno.json b/tests/specs/run/no_check_decorators/decorators/experimental/deno.json
new file mode 100644
index 0000000000..504cd646e1
--- /dev/null
+++ b/tests/specs/run/no_check_decorators/decorators/experimental/deno.json
@@ -0,0 +1,5 @@
+{
+  "compilerOptions": {
+    "experimentalDecorators": true
+  }
+}
diff --git a/tests/specs/run/no_check_decorators/decorators/experimental/no_check/main.out b/tests/specs/run/no_check_decorators/decorators/experimental/no_check/main.out
new file mode 100644
index 0000000000..015f7076e8
--- /dev/null
+++ b/tests/specs/run/no_check_decorators/decorators/experimental/no_check/main.out
@@ -0,0 +1,3 @@
+a(): evaluated
+a(): called
+method
diff --git a/tests/specs/run/no_check_decorators/decorators/experimental/no_check/main.ts b/tests/specs/run/no_check_decorators/decorators/experimental/no_check/main.ts
new file mode 100644
index 0000000000..9f7ec550d5
--- /dev/null
+++ b/tests/specs/run/no_check_decorators/decorators/experimental/no_check/main.ts
@@ -0,0 +1,21 @@
+// deno-lint-ignore-file
+function a() {
+  console.log("a(): evaluated");
+  return (
+    _target: any,
+    _propertyKey: string,
+    _descriptor: PropertyDescriptor,
+  ) => {
+    console.log("a(): called");
+  };
+}
+
+class B {
+  @a()
+  method() {
+    console.log("method");
+  }
+}
+
+const b = new B();
+b.method();
diff --git a/tests/specs/run/no_check_decorators/decorators/experimental/runtime/main.out b/tests/specs/run/no_check_decorators/decorators/experimental/runtime/main.out
new file mode 100644
index 0000000000..0fc1d4590e
--- /dev/null
+++ b/tests/specs/run/no_check_decorators/decorators/experimental/runtime/main.out
@@ -0,0 +1,7 @@
+@A evaluated
+@B evaluated
+@B called
+@A called
+fn() called from @A
+fn() called from @B
+C.test() called
diff --git a/tests/specs/run/no_check_decorators/decorators/experimental/runtime/main.ts b/tests/specs/run/no_check_decorators/decorators/experimental/runtime/main.ts
new file mode 100644
index 0000000000..40a26bbd4d
--- /dev/null
+++ b/tests/specs/run/no_check_decorators/decorators/experimental/runtime/main.ts
@@ -0,0 +1,42 @@
+// deno-lint-ignore-file
+function a() {
+  console.log("@A evaluated");
+  return function (
+    target: any,
+    propertyKey: string,
+    descriptor: PropertyDescriptor,
+  ) {
+    console.log("@A called");
+    const fn = descriptor.value;
+    descriptor.value = function () {
+      console.log("fn() called from @A");
+      fn();
+    };
+  };
+}
+
+function b() {
+  console.log("@B evaluated");
+  return function (
+    target: any,
+    propertyKey: string,
+    descriptor: PropertyDescriptor,
+  ) {
+    console.log("@B called");
+    const fn = descriptor.value;
+    descriptor.value = function () {
+      console.log("fn() called from @B");
+      fn();
+    };
+  };
+}
+
+class C {
+  @a()
+  @b()
+  static test() {
+    console.log("C.test() called");
+  }
+}
+
+C.test();
diff --git a/tests/specs/run/no_check_decorators/decorators/experimental/ts/main.out b/tests/specs/run/no_check_decorators/decorators/experimental/ts/main.out
new file mode 100644
index 0000000000..ea64fbaa63
--- /dev/null
+++ b/tests/specs/run/no_check_decorators/decorators/experimental/ts/main.out
@@ -0,0 +1,3 @@
+Warning experimentalDecorators compiler option is deprecated and may be removed at any time
+Check [WILDCARD]
+SomeClass { someField: "asdf" }
diff --git a/tests/specs/run/no_check_decorators/decorators/experimental/ts/main.ts b/tests/specs/run/no_check_decorators/decorators/experimental/ts/main.ts
new file mode 100644
index 0000000000..95fba6cd48
--- /dev/null
+++ b/tests/specs/run/no_check_decorators/decorators/experimental/ts/main.ts
@@ -0,0 +1,14 @@
+// deno-lint-ignore-file
+
+function Decorate() {
+  return function (constructor: any): any {
+    return class extends constructor {
+      protected someField: string = "asdf";
+    };
+  };
+}
+
+@Decorate()
+class SomeClass {}
+
+console.log(new SomeClass());
diff --git a/tests/specs/run/no_check_decorators/decorators/tc39_proposal/main.out b/tests/specs/run/no_check_decorators/decorators/tc39_proposal/main.out
new file mode 100644
index 0000000000..39394952e8
--- /dev/null
+++ b/tests/specs/run/no_check_decorators/decorators/tc39_proposal/main.out
@@ -0,0 +1,3 @@
+starting m with arguments 1
+C.m 1
+ending m
diff --git a/tests/specs/run/no_check_decorators/decorators/tc39_proposal/main.ts b/tests/specs/run/no_check_decorators/decorators/tc39_proposal/main.ts
new file mode 100644
index 0000000000..00c8a85025
--- /dev/null
+++ b/tests/specs/run/no_check_decorators/decorators/tc39_proposal/main.ts
@@ -0,0 +1,21 @@
+// deno-lint-ignore no-explicit-any
+function logged(value: any, { kind, name }: { kind: string; name: string }) {
+  if (kind === "method") {
+    return function (...args: unknown[]) {
+      console.log(`starting ${name} with arguments ${args.join(", ")}`);
+      // @ts-ignore this has implicit any type
+      const ret = value.call(this, ...args);
+      console.log(`ending ${name}`);
+      return ret;
+    };
+  }
+}
+
+class C {
+  @logged
+  m(arg: number) {
+    console.log("C.m", arg);
+  }
+}
+
+new C().m(1);
diff --git a/tests/specs/run/no_config_auto_discovery_for_local_script/__test__.jsonc b/tests/specs/run/no_config_auto_discovery_for_local_script/__test__.jsonc
new file mode 100644
index 0000000000..0a03dbc228
--- /dev/null
+++ b/tests/specs/run/no_config_auto_discovery_for_local_script/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --no-config --check frontend_work.ts",
+  "output": "no_auto_discovery.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/no_config_auto_discovery_for_local_script/frontend_work.ts b/tests/specs/run/no_config_auto_discovery_for_local_script/frontend_work.ts
new file mode 100644
index 0000000000..783af44e4c
--- /dev/null
+++ b/tests/specs/run/no_config_auto_discovery_for_local_script/frontend_work.ts
@@ -0,0 +1,4 @@
+function _main() {
+  console.log(document);
+}
+console.log("ok");
diff --git a/tests/testdata/run/with_config/no_auto_discovery.out b/tests/specs/run/no_config_auto_discovery_for_local_script/no_auto_discovery.out
similarity index 78%
rename from tests/testdata/run/with_config/no_auto_discovery.out
rename to tests/specs/run/no_config_auto_discovery_for_local_script/no_auto_discovery.out
index 59339ebe5f..f45a1097c7 100644
--- a/tests/testdata/run/with_config/no_auto_discovery.out
+++ b/tests/specs/run/no_config_auto_discovery_for_local_script/no_auto_discovery.out
@@ -1,4 +1,4 @@
 error: TS2584 [ERROR]: Cannot find name 'document'. Do you need to change your target library? Try changing the 'lib' compiler option to include 'dom'.
   console.log(document);
               ~~~~~~~~
-    at [WILDCARD]run/with_config/frontend_work.ts:2:15
+    at [WILDCARD]frontend_work.ts:2:15
diff --git a/tests/specs/run/no_deno_json/code/install.out b/tests/specs/run/no_deno_json/code/install.out
index 321dc8ebcb..ddaf104c3b 100644
--- a/tests/specs/run/no_deno_json/code/install.out
+++ b/tests/specs/run/no_deno_json/code/install.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/check-error
-Download http://localhost:4260/@denotest/cjs-default-export
+Download http://localhost:4260/@denotest%2fcheck-error
+Download http://localhost:4260/@denotest%2fcjs-default-export
 Download http://localhost:4260/chalk
 Download http://localhost:4260/ansi-styles
 Download http://localhost:4260/supports-color
diff --git a/tests/specs/run/no_lock_flag/__test__.jsonc b/tests/specs/run/no_lock_flag/__test__.jsonc
new file mode 100644
index 0000000000..b8485c8459
--- /dev/null
+++ b/tests/specs/run/no_lock_flag/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --allow-import --no-lock no_lock_flag/main.ts",
+  "output": "no_lock_flag/main.out",
+  "exitCode": 0
+}
diff --git a/tests/testdata/run/no_lock_flag/deno.json b/tests/specs/run/no_lock_flag/no_lock_flag/deno.json
similarity index 100%
rename from tests/testdata/run/no_lock_flag/deno.json
rename to tests/specs/run/no_lock_flag/no_lock_flag/deno.json
diff --git a/tests/testdata/run/no_lock_flag/deno.lock b/tests/specs/run/no_lock_flag/no_lock_flag/deno.lock
similarity index 100%
rename from tests/testdata/run/no_lock_flag/deno.lock
rename to tests/specs/run/no_lock_flag/no_lock_flag/deno.lock
diff --git a/tests/testdata/run/no_lock_flag/main.out b/tests/specs/run/no_lock_flag/no_lock_flag/main.out
similarity index 100%
rename from tests/testdata/run/no_lock_flag/main.out
rename to tests/specs/run/no_lock_flag/no_lock_flag/main.out
diff --git a/tests/testdata/run/no_lock_flag/main.ts b/tests/specs/run/no_lock_flag/no_lock_flag/main.ts
similarity index 100%
rename from tests/testdata/run/no_lock_flag/main.ts
rename to tests/specs/run/no_lock_flag/no_lock_flag/main.ts
diff --git a/tests/specs/run/no_prompt_flag/__test__.jsonc b/tests/specs/run/no_prompt_flag/__test__.jsonc
new file mode 100644
index 0000000000..2342a63e80
--- /dev/null
+++ b/tests/specs/run/no_prompt_flag/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --no-prompt no_prompt.ts",
+  "output": ""
+}
diff --git a/tests/specs/run/no_prompt_flag/no_prompt.ts b/tests/specs/run/no_prompt_flag/no_prompt.ts
new file mode 100644
index 0000000000..17d54b92c1
--- /dev/null
+++ b/tests/specs/run/no_prompt_flag/no_prompt.ts
@@ -0,0 +1,10 @@
+new Worker("data:,setTimeout(() => Deno.exit(2), 200)", { type: "module" });
+
+try {
+  await new Deno.Command("ps", {
+    stdout: "inherit",
+    stderr: "inherit",
+  }).output();
+} catch {
+  Deno.exit(0);
+}
diff --git a/tests/specs/run/node_env_var_allowlist/__test__.jsonc b/tests/specs/run/node_env_var_allowlist/__test__.jsonc
new file mode 100644
index 0000000000..055ac62e89
--- /dev/null
+++ b/tests/specs/run/node_env_var_allowlist/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --no-prompt node_env_var_allowlist.ts",
+  "output": "node_env_var_allowlist.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/node_env_var_allowlist.ts b/tests/specs/run/node_env_var_allowlist/node_env_var_allowlist.ts
similarity index 100%
rename from tests/testdata/run/node_env_var_allowlist.ts
rename to tests/specs/run/node_env_var_allowlist/node_env_var_allowlist.ts
diff --git a/tests/testdata/run/node_env_var_allowlist.ts.out b/tests/specs/run/node_env_var_allowlist/node_env_var_allowlist.ts.out
similarity index 100%
rename from tests/testdata/run/node_env_var_allowlist.ts.out
rename to tests/specs/run/node_env_var_allowlist/node_env_var_allowlist.ts.out
diff --git a/tests/specs/run/node_globals_hints/__test__.jsonc b/tests/specs/run/node_globals_hints/__test__.jsonc
new file mode 100644
index 0000000000..c5c5d6e42e
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/__test__.jsonc
@@ -0,0 +1,34 @@
+{
+  "tests": {
+    "__dirname": {
+      "args": "run dirname.js",
+      "output": "dirname.out",
+      "exitCode": 1
+    },
+    "__filename": {
+      "args": "run filename.js",
+      "output": "filename.out",
+      "exitCode": 1
+    },
+    "clearImmediate": {
+      "args": "run clear_immediate.js",
+      "output": "clear_immediate.out",
+      "exitCode": 1
+    },
+    "buffer": {
+      "args": "run buffer.js",
+      "output": "buffer.out",
+      "exitCode": 1
+    },
+    "global": {
+      "args": "run global.js",
+      "output": "global.out",
+      "exitCode": 1
+    },
+    "setImmediate": {
+      "args": "run set_immediate.js",
+      "output": "set_immediate.out",
+      "exitCode": 1
+    }
+  }
+}
diff --git a/tests/specs/run/node_globals_hints/buffer.js b/tests/specs/run/node_globals_hints/buffer.js
new file mode 100644
index 0000000000..9809e1656e
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/buffer.js
@@ -0,0 +1 @@
+Buffer;
diff --git a/tests/specs/run/node_globals_hints/buffer.out b/tests/specs/run/node_globals_hints/buffer.out
new file mode 100644
index 0000000000..858f404ab5
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/buffer.out
@@ -0,0 +1,8 @@
+error: Uncaught (in promise) ReferenceError: Buffer is not defined
+Buffer;
+^
+    at [WILDCARD]buffer.js:1:1
+
+    info: Buffer is not available in the global scope in Deno.
+    hint: Import it explicitly with import { Buffer } from "node:buffer";,
+          or run again with --unstable-node-globals flag to add this global.
diff --git a/tests/specs/run/node_globals_hints/clear_immediate.js b/tests/specs/run/node_globals_hints/clear_immediate.js
new file mode 100644
index 0000000000..94b26ae682
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/clear_immediate.js
@@ -0,0 +1 @@
+clearImmediate;
diff --git a/tests/specs/run/node_globals_hints/clear_immediate.out b/tests/specs/run/node_globals_hints/clear_immediate.out
new file mode 100644
index 0000000000..a973a31723
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/clear_immediate.out
@@ -0,0 +1,8 @@
+error: Uncaught (in promise) ReferenceError: clearImmediate is not defined
+clearImmediate;
+^
+    at [WILDCARD]clear_immediate.js:1:1
+
+    info: clearImmediate is not available in the global scope in Deno.
+    hint: Import it explicitly with import { clearImmediate } from "node:timers";,
+          or run again with --unstable-node-globals flag to add this global.
diff --git a/tests/specs/run/node_globals_hints/dirname.js b/tests/specs/run/node_globals_hints/dirname.js
new file mode 100644
index 0000000000..58d9e93794
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/dirname.js
@@ -0,0 +1 @@
+__dirname;
diff --git a/tests/specs/run/node_globals_hints/dirname.out b/tests/specs/run/node_globals_hints/dirname.out
new file mode 100644
index 0000000000..0aa3e4f51b
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/dirname.out
@@ -0,0 +1,7 @@
+error: Uncaught (in promise) ReferenceError: __dirname is not defined
+__dirname;
+^
+    at [WILDCARD]dirname.js:1:1
+
+    info: __dirname global is not available in ES modules.
+    hint: Use import.meta.dirname instead.
diff --git a/tests/specs/run/node_globals_hints/filename.js b/tests/specs/run/node_globals_hints/filename.js
new file mode 100644
index 0000000000..31770bb141
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/filename.js
@@ -0,0 +1 @@
+__filename;
diff --git a/tests/specs/run/node_globals_hints/filename.out b/tests/specs/run/node_globals_hints/filename.out
new file mode 100644
index 0000000000..47b4264fbd
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/filename.out
@@ -0,0 +1,7 @@
+error: Uncaught (in promise) ReferenceError: __filename is not defined
+__filename;
+^
+    at [WILDCARD]filename.js:1:1
+
+    info: __filename global is not available in ES modules.
+    hint: Use import.meta.filename instead.
diff --git a/tests/specs/run/node_globals_hints/global.js b/tests/specs/run/node_globals_hints/global.js
new file mode 100644
index 0000000000..56676d726a
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/global.js
@@ -0,0 +1 @@
+global;
diff --git a/tests/specs/run/node_globals_hints/global.out b/tests/specs/run/node_globals_hints/global.out
new file mode 100644
index 0000000000..ad01ac426d
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/global.out
@@ -0,0 +1,8 @@
+error: Uncaught (in promise) ReferenceError: global is not defined
+global;
+^
+    at [WILDCARD]global.js:1:1
+
+    info: global is not available in the global scope in Deno.
+    hint: Use globalThis instead, or assign globalThis.global = globalThis,
+          or run again with --unstable-node-globals flag to add this global.
diff --git a/tests/specs/run/node_globals_hints/set_immediate.js b/tests/specs/run/node_globals_hints/set_immediate.js
new file mode 100644
index 0000000000..fa29d1e714
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/set_immediate.js
@@ -0,0 +1 @@
+setImmediate;
diff --git a/tests/specs/run/node_globals_hints/set_immediate.out b/tests/specs/run/node_globals_hints/set_immediate.out
new file mode 100644
index 0000000000..b3feb3127d
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/set_immediate.out
@@ -0,0 +1,8 @@
+error: Uncaught (in promise) ReferenceError: setImmediate is not defined
+setImmediate;
+^
+    at [WILDCARD]set_immediate.js:1:1
+
+    info: setImmediate is not available in the global scope in Deno.
+    hint: Import it explicitly with import { setImmediate } from "node:timers";,
+          or run again with --unstable-node-globals flag to add this global.
diff --git a/tests/specs/run/npm_pkg_requires_esm_js/__test__.jsonc b/tests/specs/run/npm_pkg_requires_esm_js/__test__.jsonc
new file mode 100644
index 0000000000..3da8db4048
--- /dev/null
+++ b/tests/specs/run/npm_pkg_requires_esm_js/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run -A main.js",
+  "output": "output.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/npm_pkg_requires_esm_js/file.js b/tests/specs/run/npm_pkg_requires_esm_js/file.js
new file mode 100644
index 0000000000..d9536a69b3
--- /dev/null
+++ b/tests/specs/run/npm_pkg_requires_esm_js/file.js
@@ -0,0 +1 @@
+console.log(import.meta.url);
diff --git a/tests/specs/run/npm_pkg_requires_esm_js/logs_require.js b/tests/specs/run/npm_pkg_requires_esm_js/logs_require.js
new file mode 100644
index 0000000000..984e1f3e74
--- /dev/null
+++ b/tests/specs/run/npm_pkg_requires_esm_js/logs_require.js
@@ -0,0 +1 @@
+console.log(require);
diff --git a/tests/specs/run/npm_pkg_requires_esm_js/main.js b/tests/specs/run/npm_pkg_requires_esm_js/main.js
new file mode 100644
index 0000000000..3704c8bf68
--- /dev/null
+++ b/tests/specs/run/npm_pkg_requires_esm_js/main.js
@@ -0,0 +1,5 @@
+import doRequire from "package";
+import path from "node:path";
+
+doRequire(path.resolve(import.meta.dirname, "file.js"));
+doRequire(path.resolve(import.meta.dirname, "logs_require.js"));
diff --git a/tests/specs/run/npm_pkg_requires_esm_js/node_modules/package/index.js b/tests/specs/run/npm_pkg_requires_esm_js/node_modules/package/index.js
new file mode 100644
index 0000000000..5d78723713
--- /dev/null
+++ b/tests/specs/run/npm_pkg_requires_esm_js/node_modules/package/index.js
@@ -0,0 +1,3 @@
+module.exports = (file) => {
+  return require(file);
+};
diff --git a/tests/specs/run/npm_pkg_requires_esm_js/node_modules/package/package.json b/tests/specs/run/npm_pkg_requires_esm_js/node_modules/package/package.json
new file mode 100644
index 0000000000..5723987e9f
--- /dev/null
+++ b/tests/specs/run/npm_pkg_requires_esm_js/node_modules/package/package.json
@@ -0,0 +1,4 @@
+{
+  "name": "package",
+  "version": "1.0.0"
+}
\ No newline at end of file
diff --git a/tests/specs/run/npm_pkg_requires_esm_js/output.out b/tests/specs/run/npm_pkg_requires_esm_js/output.out
new file mode 100644
index 0000000000..2cae7108b0
--- /dev/null
+++ b/tests/specs/run/npm_pkg_requires_esm_js/output.out
@@ -0,0 +1,12 @@
+file:///[WILDLINE]/file.js
+error: Uncaught (in promise) ReferenceError: require is not defined
+console.log(require);
+            ^
+    at [WILDCARD]
+
+    info: Deno supports CommonJS modules in .cjs files, or when the closest
+          package.json has a "type": "commonjs" option.
+    hint: Rewrite this module to ESM,
+          or change the file extension to .cjs,
+          or add package.json next to the file with "type": "commonjs" option.
+    docs: https://docs.deno.com/go/commonjs
diff --git a/tests/specs/run/npm_pkg_requires_esm_js/package.json b/tests/specs/run/npm_pkg_requires_esm_js/package.json
new file mode 100644
index 0000000000..e69de29bb2
diff --git a/tests/specs/run/onload/__test__.jsonc b/tests/specs/run/onload/__test__.jsonc
new file mode 100644
index 0000000000..b17dc665d1
--- /dev/null
+++ b/tests/specs/run/onload/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --config deno.json onload/main.ts",
+  "output": "onload/main.out"
+}
diff --git a/tests/specs/run/onload/deno.json b/tests/specs/run/onload/deno.json
new file mode 100644
index 0000000000..105514e133
--- /dev/null
+++ b/tests/specs/run/onload/deno.json
@@ -0,0 +1,4 @@
+{
+  "lock": false,
+  "importMap": "../../../../import_map.json"
+}
diff --git a/tests/testdata/run/onload/imported.ts b/tests/specs/run/onload/onload/imported.ts
similarity index 100%
rename from tests/testdata/run/onload/imported.ts
rename to tests/specs/run/onload/onload/imported.ts
diff --git a/tests/testdata/run/onload/main.out b/tests/specs/run/onload/onload/main.out
similarity index 100%
rename from tests/testdata/run/onload/main.out
rename to tests/specs/run/onload/onload/main.out
diff --git a/tests/testdata/run/onload/main.ts b/tests/specs/run/onload/onload/main.ts
similarity index 100%
rename from tests/testdata/run/onload/main.ts
rename to tests/specs/run/onload/onload/main.ts
diff --git a/tests/testdata/run/onload/nest_imported.ts b/tests/specs/run/onload/onload/nest_imported.ts
similarity index 100%
rename from tests/testdata/run/onload/nest_imported.ts
rename to tests/specs/run/onload/onload/nest_imported.ts
diff --git a/tests/specs/run/op_exit_op_set_exit_code_in_worker/__test__.jsonc b/tests/specs/run/op_exit_op_set_exit_code_in_worker/__test__.jsonc
new file mode 100644
index 0000000000..664fcb5c15
--- /dev/null
+++ b/tests/specs/run/op_exit_op_set_exit_code_in_worker/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --no-check --allow-read op_exit_op_set_exit_code_in_worker.ts",
+  "output": "",
+  "exitCode": 21
+}
diff --git a/tests/testdata/run/op_exit_op_set_exit_code_in_worker.ts b/tests/specs/run/op_exit_op_set_exit_code_in_worker/op_exit_op_set_exit_code_in_worker.ts
similarity index 100%
rename from tests/testdata/run/op_exit_op_set_exit_code_in_worker.ts
rename to tests/specs/run/op_exit_op_set_exit_code_in_worker/op_exit_op_set_exit_code_in_worker.ts
diff --git a/tests/specs/run/op_exit_op_set_exit_code_in_worker/op_exit_op_set_exit_code_worker.js b/tests/specs/run/op_exit_op_set_exit_code_in_worker/op_exit_op_set_exit_code_worker.js
new file mode 100644
index 0000000000..9b284c37df
--- /dev/null
+++ b/tests/specs/run/op_exit_op_set_exit_code_in_worker/op_exit_op_set_exit_code_worker.js
@@ -0,0 +1,4 @@
+self.onmessage = () => {
+  Deno[Deno.internal].core.ops.op_set_exit_code(42);
+  Deno.exit();
+};
diff --git a/tests/specs/run/package_json/invalid_value/__test__.jsonc b/tests/specs/run/package_json/invalid_value/__test__.jsonc
index 7f85713cb5..195734d95f 100644
--- a/tests/specs/run/package_json/invalid_value/__test__.jsonc
+++ b/tests/specs/run/package_json/invalid_value/__test__.jsonc
@@ -1,22 +1,29 @@
 {
   "tempDir": true,
-  // TODO(2.0): update the tests, should probably run install first
-  "ignore": true,
   "tests": {
     // should run fine when not referencing a failing dep entry
-    "run_ok": {
-      "args": "run ok.ts",
+    "run_ok_auto": {
+      "args": "run --quiet --node-modules-dir=auto ok.ts",
       "output": "ok.ts.out"
     },
     // should fail when referencing a failing dep entry
-    "run_error": {
-      "args": "run error.ts",
+    "run_error_auto": {
+      "args": "run --node-modules-dir=auto error.ts",
       "exitCode": 1,
-      "output": "error.ts.out"
+      "output": "error_auto.out"
+    },
+    "install_error_byonm": {
+      "args": "install",
+      "output": "install.out",
+      "exitCode": 1
+    },
+    "add_error_byonm": {
+      "args": "add npm:cowsay",
+      "output": "add.out",
+      "exitCode": 1
     },
-    // should output a warning about the failing dep entry
     "task_test": {
-      "args": "task test",
+      "args": "task --node-modules-dir=auto test",
       "output": "task.out"
     }
   }
diff --git a/tests/specs/run/package_json/invalid_value/add.out b/tests/specs/run/package_json/invalid_value/add.out
new file mode 100644
index 0000000000..32d9acaed6
--- /dev/null
+++ b/tests/specs/run/package_json/invalid_value/add.out
@@ -0,0 +1,9 @@
+Add npm:cowsay@1.5.0
+error: Failed to install '@denotest/cjs-default-export'
+    at file:///[WILDLINE]/package.json
+
+Caused by:
+    0: Invalid version requirement
+    1: Unexpected character.
+         invalid stuff that won't parse
+         ~
diff --git a/tests/specs/run/package_json/invalid_value/error.out b/tests/specs/run/package_json/invalid_value/error.out
new file mode 100644
index 0000000000..5975351131
--- /dev/null
+++ b/tests/specs/run/package_json/invalid_value/error.out
@@ -0,0 +1,2 @@
+error: Could not resolve "@denotest/cjs-default-export", but found it in a package.json. Deno expects the node_modules/ directory to be up to date. Did you forget to run `deno install`?
+    at file:///[WILDCARD]/error.ts:2:23
diff --git a/tests/specs/run/package_json/invalid_value/error.ts.out b/tests/specs/run/package_json/invalid_value/error_auto.out
similarity index 50%
rename from tests/specs/run/package_json/invalid_value/error.ts.out
rename to tests/specs/run/package_json/invalid_value/error_auto.out
index 37796d6da1..966375a3df 100644
--- a/tests/specs/run/package_json/invalid_value/error.ts.out
+++ b/tests/specs/run/package_json/invalid_value/error_auto.out
@@ -1,3 +1,6 @@
+Download http://localhost:4260/@denotest%2fesm-basic
+Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
+Initialize @denotest/esm-basic@1.0.0
 error: Invalid version requirement
     0: Unexpected character.
          invalid stuff that won't parse
diff --git a/tests/specs/run/package_json/invalid_value/install.out b/tests/specs/run/package_json/invalid_value/install.out
new file mode 100644
index 0000000000..ca3492ab22
--- /dev/null
+++ b/tests/specs/run/package_json/invalid_value/install.out
@@ -0,0 +1,8 @@
+error: Failed to install '@denotest/cjs-default-export'
+    at file:///[WILDLINE]/package.json
+
+Caused by:
+    0: Invalid version requirement
+    1: Unexpected character.
+         invalid stuff that won't parse
+         ~
diff --git a/tests/specs/run/package_json/invalid_value/ok.ts.out b/tests/specs/run/package_json/invalid_value/ok.ts.out
index e8fff7ed7a..0cfbf08886 100644
--- a/tests/specs/run/package_json/invalid_value/ok.ts.out
+++ b/tests/specs/run/package_json/invalid_value/ok.ts.out
@@ -1,4 +1 @@
-Download http://localhost:4260/@denotest/esm-basic
-Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
-Initialize @denotest/esm-basic@1.0.0
 2
diff --git a/tests/specs/run/package_json/invalid_value/task.out b/tests/specs/run/package_json/invalid_value/task.out
index d0adb05256..2f9580fa61 100644
--- a/tests/specs/run/package_json/invalid_value/task.out
+++ b/tests/specs/run/package_json/invalid_value/task.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 Task test echo 1
diff --git a/tests/specs/run/package_json_auto_discovered_for_local_script_arg_with_stop/__test__.jsonc b/tests/specs/run/package_json_auto_discovered_for_local_script_arg_with_stop/__test__.jsonc
new file mode 100644
index 0000000000..ac66ccdf14
--- /dev/null
+++ b/tests/specs/run/package_json_auto_discovered_for_local_script_arg_with_stop/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run -L debug main.ts",
+  "output": "main.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/package_json_auto_discovered_for_local_script_arg_with_stop/deno.json b/tests/specs/run/package_json_auto_discovered_for_local_script_arg_with_stop/deno.json
new file mode 100644
index 0000000000..36e1765d1a
--- /dev/null
+++ b/tests/specs/run/package_json_auto_discovered_for_local_script_arg_with_stop/deno.json
@@ -0,0 +1,5 @@
+{
+  "tasks": {
+    "dev": "deno run main.ts"
+  }
+}
diff --git a/tests/specs/run/package_json_auto_discovered_for_local_script_arg_with_stop/main.out b/tests/specs/run/package_json_auto_discovered_for_local_script_arg_with_stop/main.out
new file mode 100644
index 0000000000..5ab43ac470
--- /dev/null
+++ b/tests/specs/run/package_json_auto_discovered_for_local_script_arg_with_stop/main.out
@@ -0,0 +1,5 @@
+[WILDCARD]Config file found at '[WILDCARD]deno.json'
+[WILDCARD]
+error: Relative import path "chalk" not prefixed with / or ./ or ../
+  hint: If you want to use a JSR or npm package, try running `deno add jsr:chalk` or `deno add npm:chalk`
+    at file:///[WILDCARD]/main.ts:3:19
diff --git a/tests/specs/run/package_json_auto_discovered_for_local_script_arg_with_stop/main.ts b/tests/specs/run/package_json_auto_discovered_for_local_script_arg_with_stop/main.ts
new file mode 100644
index 0000000000..6016470a10
--- /dev/null
+++ b/tests/specs/run/package_json_auto_discovered_for_local_script_arg_with_stop/main.ts
@@ -0,0 +1,6 @@
+// This import should fail, because `package.json` is not discovered, as we're
+// stopping the discovery when encountering `deno.json`.
+import chalk from "chalk";
+
+console.log("ok");
+console.log(chalk);
diff --git a/tests/specs/run/package_json_type/commonjs/basic/__test__.jsonc b/tests/specs/run/package_json_type/commonjs/basic/__test__.jsonc
new file mode 100644
index 0000000000..85b7219fa0
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/__test__.jsonc
@@ -0,0 +1,34 @@
+{
+  "tests": {
+    "main_cjs": {
+      "args": "run --allow-read=. main_cjs.js",
+      "output": "3\n"
+    },
+    "main_esm": {
+      "args": "run --allow-read=. main_esm.js",
+      "output": "3\n"
+    },
+    "main_mix": {
+      "args": "run --allow-read=. main_mix.js",
+      "output": "main_mix.out",
+      "exitCode": 1
+    },
+    "import_import_meta": {
+      "args": "run import_import_meta.js",
+      "output": "[WILDLINE]/import_meta.js\n"
+    },
+    "main_import_meta": {
+      "args": "run main_esm_import_meta.js",
+      "output": "main_esm_import_meta.out",
+      "exitCode": 1
+    },
+    "not_import_meta": {
+      "args": "run --allow-read=. not_import_meta.js",
+      "output": "3\n"
+    },
+    "tla": {
+      "args": "run --allow-read=. tla.js",
+      "output": "loaded\n"
+    }
+  }
+}
diff --git a/tests/specs/run/package_json_type/commonjs/basic/add.js b/tests/specs/run/package_json_type/commonjs/basic/add.js
new file mode 100644
index 0000000000..2a886fbc18
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/add.js
@@ -0,0 +1,3 @@
+module.exports.add = function (a, b) {
+  return a + b;
+};
diff --git a/tests/specs/run/package_json_type/commonjs/basic/import_import_meta.js b/tests/specs/run/package_json_type/commonjs/basic/import_import_meta.js
new file mode 100644
index 0000000000..f07518985a
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/import_import_meta.js
@@ -0,0 +1,3 @@
+import { value } from "./import_meta.js";
+
+console.log(value);
diff --git a/tests/specs/run/package_json_type/commonjs/basic/import_meta.js b/tests/specs/run/package_json_type/commonjs/basic/import_meta.js
new file mode 100644
index 0000000000..2bdbc30fe6
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/import_meta.js
@@ -0,0 +1 @@
+export const value = import.meta.url;
diff --git a/tests/specs/run/package_json_type/commonjs/basic/main_cjs.js b/tests/specs/run/package_json_type/commonjs/basic/main_cjs.js
new file mode 100644
index 0000000000..365e8e06f8
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/main_cjs.js
@@ -0,0 +1,2 @@
+const { add } = require("./add");
+console.log(add(1, 2));
diff --git a/tests/specs/run/package_json_type/commonjs/basic/main_esm.js b/tests/specs/run/package_json_type/commonjs/basic/main_esm.js
new file mode 100644
index 0000000000..8c55f673b0
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/main_esm.js
@@ -0,0 +1,3 @@
+import { add } from "./add.js";
+
+console.log(add(1, 2));
diff --git a/tests/specs/run/package_json_type/commonjs/basic/main_esm_import_meta.js b/tests/specs/run/package_json_type/commonjs/basic/main_esm_import_meta.js
new file mode 100644
index 0000000000..f1dff20b57
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/main_esm_import_meta.js
@@ -0,0 +1,2 @@
+console.log(import.meta.url);
+console.log(require("./add"));
diff --git a/tests/specs/run/package_json_type/commonjs/basic/main_esm_import_meta.out b/tests/specs/run/package_json_type/commonjs/basic/main_esm_import_meta.out
new file mode 100644
index 0000000000..e177defffd
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/main_esm_import_meta.out
@@ -0,0 +1,2 @@
+[WILDLINE]main_esm_import_meta.js
+error: Uncaught (in promise) ReferenceError: require is not defined[WILDCARD]
diff --git a/tests/specs/run/package_json_type/commonjs/basic/main_mix.js b/tests/specs/run/package_json_type/commonjs/basic/main_mix.js
new file mode 100644
index 0000000000..2a2c2c62a2
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/main_mix.js
@@ -0,0 +1,6 @@
+import { add } from "./add.js";
+
+console.log(add(1, 2));
+
+// will error
+console.log(require("./add").add(1, 2));
diff --git a/tests/specs/run/package_json_type/commonjs/basic/main_mix.out b/tests/specs/run/package_json_type/commonjs/basic/main_mix.out
new file mode 100644
index 0000000000..65671fd618
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/main_mix.out
@@ -0,0 +1,12 @@
+3
+error: Uncaught (in promise) ReferenceError: require is not defined
+console.log(require("./add").add(1, 2));
+        ^
+    at file:///[WILDLINE]main_mix.js:[WILDLINE]
+
+    info: Deno supports CommonJS modules in .cjs files, or when the closest
+          package.json has a "type": "commonjs" option.
+    hint: Rewrite this module to ESM,
+          or change the file extension to .cjs,
+          or add package.json next to the file with "type": "commonjs" option.
+    docs: https://docs.deno.com/go/commonjs
diff --git a/tests/specs/run/package_json_type/commonjs/basic/not_import_meta.js b/tests/specs/run/package_json_type/commonjs/basic/not_import_meta.js
new file mode 100644
index 0000000000..216b900df6
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/not_import_meta.js
@@ -0,0 +1,8 @@
+try {
+  console.log(test.import.meta.url);
+} catch {
+  // ignore
+}
+
+// should work because this is not an ESM file
+console.log(require("./add").add(1, 2));
diff --git a/tests/specs/run/package_json_type/commonjs/basic/package.json b/tests/specs/run/package_json_type/commonjs/basic/package.json
new file mode 100644
index 0000000000..5bbefffbab
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/package.json
@@ -0,0 +1,3 @@
+{
+  "type": "commonjs"
+}
diff --git a/tests/specs/run/package_json_type/commonjs/basic/tla.js b/tests/specs/run/package_json_type/commonjs/basic/tla.js
new file mode 100644
index 0000000000..978578de46
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/tla.js
@@ -0,0 +1,2 @@
+await new Promise((r) => r());
+console.log("loaded");
diff --git a/tests/specs/run/package_json_type/commonjs/jsx/__test__.jsonc b/tests/specs/run/package_json_type/commonjs/jsx/__test__.jsonc
new file mode 100644
index 0000000000..f815fd72cb
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/jsx/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "tempDir": true,
+  "args": "run -A --quiet main.jsx",
+  "output": "main.out"
+}
diff --git a/tests/specs/run/package_json_type/commonjs/jsx/add.js b/tests/specs/run/package_json_type/commonjs/jsx/add.js
new file mode 100644
index 0000000000..2a886fbc18
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/jsx/add.js
@@ -0,0 +1,3 @@
+module.exports.add = function (a, b) {
+  return a + b;
+};
diff --git a/tests/specs/run/package_json_type/commonjs/jsx/deno.jsonc b/tests/specs/run/package_json_type/commonjs/jsx/deno.jsonc
new file mode 100644
index 0000000000..31d05ffb74
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/jsx/deno.jsonc
@@ -0,0 +1,7 @@
+{
+  "nodeModulesDir": "auto",
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "react"
+  }
+}
diff --git a/tests/specs/run/package_json_type/commonjs/jsx/main.jsx b/tests/specs/run/package_json_type/commonjs/jsx/main.jsx
new file mode 100644
index 0000000000..1922fce1bb
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/jsx/main.jsx
@@ -0,0 +1,7 @@
+const { add } = require("./add.js");
+
+console.log(add(1, 2));
+
+console.log(<div /> != null);
+
+require("./tsx.tsx");
diff --git a/tests/specs/run/package_json_type/commonjs/jsx/main.out b/tests/specs/run/package_json_type/commonjs/jsx/main.out
new file mode 100644
index 0000000000..cdcf045418
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/jsx/main.out
@@ -0,0 +1,4 @@
+3
+true
+4
+true
diff --git a/tests/specs/run/package_json_type/commonjs/jsx/package.json b/tests/specs/run/package_json_type/commonjs/jsx/package.json
new file mode 100644
index 0000000000..88afcdcd95
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/jsx/package.json
@@ -0,0 +1,7 @@
+{
+  "type": "commonjs",
+  "dependencies": {
+    "@types/react": "*",
+    "react": "*"
+  }
+}
diff --git a/tests/specs/run/package_json_type/commonjs/jsx/tsx.tsx b/tests/specs/run/package_json_type/commonjs/jsx/tsx.tsx
new file mode 100644
index 0000000000..ad8f0c0a9c
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/jsx/tsx.tsx
@@ -0,0 +1,5 @@
+import mod = require("./add.js");
+
+console.log(mod.add(2, 2));
+
+console.log(<div /> != null);
diff --git a/tests/specs/run/package_json_type/none/__test__.jsonc b/tests/specs/run/package_json_type/none/__test__.jsonc
new file mode 100644
index 0000000000..fa1d22ca18
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/__test__.jsonc
@@ -0,0 +1,18 @@
+{
+  "tests": {
+    "main_cjs": {
+      "args": "run --allow-read=. main_cjs.js",
+      "output": "main_cjs.out",
+      "exitCode": 1
+    },
+    "main_esm": {
+      "args": "run --allow-read=. main_esm.js",
+      "output": "main_esm.out",
+      "exitCode": 1
+    },
+    "sub_folder_cjs": {
+      "args": "run --allow-read=. sub_folder_cjs.js",
+      "output": "3\n"
+    }
+  }
+}
diff --git a/tests/specs/run/package_json_type/none/add.js b/tests/specs/run/package_json_type/none/add.js
new file mode 100644
index 0000000000..2a886fbc18
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/add.js
@@ -0,0 +1,3 @@
+module.exports.add = function (a, b) {
+  return a + b;
+};
diff --git a/tests/specs/run/package_json_type/none/commonjs/add.js b/tests/specs/run/package_json_type/none/commonjs/add.js
new file mode 100644
index 0000000000..2a886fbc18
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/commonjs/add.js
@@ -0,0 +1,3 @@
+module.exports.add = function (a, b) {
+  return a + b;
+};
diff --git a/tests/specs/run/package_json_type/none/commonjs/package.json b/tests/specs/run/package_json_type/none/commonjs/package.json
new file mode 100644
index 0000000000..5bbefffbab
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/commonjs/package.json
@@ -0,0 +1,3 @@
+{
+  "type": "commonjs"
+}
diff --git a/tests/specs/run/package_json_type/none/main_cjs.js b/tests/specs/run/package_json_type/none/main_cjs.js
new file mode 100644
index 0000000000..365e8e06f8
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/main_cjs.js
@@ -0,0 +1,2 @@
+const { add } = require("./add");
+console.log(add(1, 2));
diff --git a/tests/specs/run/package_json_type/none/main_cjs.out b/tests/specs/run/package_json_type/none/main_cjs.out
new file mode 100644
index 0000000000..afa5028f4f
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/main_cjs.out
@@ -0,0 +1,11 @@
+error: Uncaught (in promise) ReferenceError: require is not defined
+const { add } = require("./add");
+                ^
+    at file:///[WILDLINE]
+
+    info: Deno supports CommonJS modules in .cjs files, or when the closest
+          package.json has a "type": "commonjs" option.
+    hint: Rewrite this module to ESM,
+          or change the file extension to .cjs,
+          or add package.json next to the file with "type": "commonjs" option.
+    docs: https://docs.deno.com/go/commonjs
diff --git a/tests/specs/run/package_json_type/none/main_esm.js b/tests/specs/run/package_json_type/none/main_esm.js
new file mode 100644
index 0000000000..8c55f673b0
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/main_esm.js
@@ -0,0 +1,3 @@
+import { add } from "./add.js";
+
+console.log(add(1, 2));
diff --git a/tests/specs/run/package_json_type/none/main_esm.out b/tests/specs/run/package_json_type/none/main_esm.out
new file mode 100644
index 0000000000..5f16c5f350
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/main_esm.out
@@ -0,0 +1,4 @@
+error: Uncaught SyntaxError: The requested module './add.js' does not provide an export named 'add'
+import { add } from "./add.js";
+         ^
+    at <anonymous> (file:///[WILDLINE])
diff --git a/tests/specs/run/package_json_type/none/package.json b/tests/specs/run/package_json_type/none/package.json
new file mode 100644
index 0000000000..2c63c08510
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/package.json
@@ -0,0 +1,2 @@
+{
+}
diff --git a/tests/specs/run/package_json_type/none/sub_folder_cjs.js b/tests/specs/run/package_json_type/none/sub_folder_cjs.js
new file mode 100644
index 0000000000..ad04e67301
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/sub_folder_cjs.js
@@ -0,0 +1,3 @@
+import { add } from "./commonjs/add.js";
+
+console.log(add(1, 2));
diff --git a/tests/specs/run/permission_args/001_hello.js b/tests/specs/run/permission_args/001_hello.js
new file mode 100644
index 0000000000..accefceba6
--- /dev/null
+++ b/tests/specs/run/permission_args/001_hello.js
@@ -0,0 +1 @@
+console.log("Hello World");
diff --git a/tests/specs/run/permission_args/__test__.jsonc b/tests/specs/run/permission_args/__test__.jsonc
new file mode 100644
index 0000000000..2843ee3955
--- /dev/null
+++ b/tests/specs/run/permission_args/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run 001_hello.js --allow-net",
+  "output": "permission_args.out"
+}
diff --git a/tests/testdata/run/permission_args.out b/tests/specs/run/permission_args/permission_args.out
similarity index 100%
rename from tests/testdata/run/permission_args.out
rename to tests/specs/run/permission_args/permission_args.out
diff --git a/tests/specs/run/permission_args_quiet/001_hello.js b/tests/specs/run/permission_args_quiet/001_hello.js
new file mode 100644
index 0000000000..accefceba6
--- /dev/null
+++ b/tests/specs/run/permission_args_quiet/001_hello.js
@@ -0,0 +1 @@
+console.log("Hello World");
diff --git a/tests/specs/run/permission_args_quiet/001_hello.js.out b/tests/specs/run/permission_args_quiet/001_hello.js.out
new file mode 100644
index 0000000000..557db03de9
--- /dev/null
+++ b/tests/specs/run/permission_args_quiet/001_hello.js.out
@@ -0,0 +1 @@
+Hello World
diff --git a/tests/specs/run/permission_args_quiet/__test__.jsonc b/tests/specs/run/permission_args_quiet/__test__.jsonc
new file mode 100644
index 0000000000..2b98b963e3
--- /dev/null
+++ b/tests/specs/run/permission_args_quiet/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet 001_hello.js --allow-net",
+  "output": "001_hello.js.out"
+}
diff --git a/tests/specs/run/private_field_presence/__test__.jsonc b/tests/specs/run/private_field_presence/__test__.jsonc
new file mode 100644
index 0000000000..982b882896
--- /dev/null
+++ b/tests/specs/run/private_field_presence/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload private_field_presence.ts",
+  "output": "private_field_presence.ts.out"
+}
diff --git a/tests/testdata/run/private_field_presence.ts b/tests/specs/run/private_field_presence/private_field_presence.ts
similarity index 100%
rename from tests/testdata/run/private_field_presence.ts
rename to tests/specs/run/private_field_presence/private_field_presence.ts
diff --git a/tests/testdata/run/private_field_presence.ts.out b/tests/specs/run/private_field_presence/private_field_presence.ts.out
similarity index 100%
rename from tests/testdata/run/private_field_presence.ts.out
rename to tests/specs/run/private_field_presence/private_field_presence.ts.out
diff --git a/tests/specs/run/private_field_presence_no_check/__test__.jsonc b/tests/specs/run/private_field_presence_no_check/__test__.jsonc
new file mode 100644
index 0000000000..b7a26db256
--- /dev/null
+++ b/tests/specs/run/private_field_presence_no_check/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload --no-check private_field_presence.ts",
+  "output": "private_field_presence.ts.out"
+}
diff --git a/tests/specs/run/private_field_presence_no_check/private_field_presence.ts b/tests/specs/run/private_field_presence_no_check/private_field_presence.ts
new file mode 100644
index 0000000000..7ce2840d8e
--- /dev/null
+++ b/tests/specs/run/private_field_presence_no_check/private_field_presence.ts
@@ -0,0 +1,20 @@
+export class Person {
+  #name: string;
+  constructor(name: string) {
+    this.#name = name;
+  }
+
+  equals(other: unknown) {
+    return other &&
+      typeof other === "object" &&
+      #name in other &&
+      this.#name === other.#name;
+  }
+}
+
+const a = new Person("alice");
+const b = new Person("bob");
+const c = new Person("alice");
+
+console.log(a.equals(b));
+console.log(a.equals(c));
diff --git a/tests/specs/run/private_field_presence_no_check/private_field_presence.ts.out b/tests/specs/run/private_field_presence_no_check/private_field_presence.ts.out
new file mode 100644
index 0000000000..1d474d5255
--- /dev/null
+++ b/tests/specs/run/private_field_presence_no_check/private_field_presence.ts.out
@@ -0,0 +1,2 @@
+false
+true
diff --git a/tests/specs/run/proto_exploit/__test__.jsonc b/tests/specs/run/proto_exploit/__test__.jsonc
new file mode 100644
index 0000000000..218f38654a
--- /dev/null
+++ b/tests/specs/run/proto_exploit/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run proto_exploit.js",
+  "output": "proto_exploit.js.out"
+}
diff --git a/tests/testdata/run/proto_exploit.js b/tests/specs/run/proto_exploit/proto_exploit.js
similarity index 100%
rename from tests/testdata/run/proto_exploit.js
rename to tests/specs/run/proto_exploit/proto_exploit.js
diff --git a/tests/testdata/run/proto_exploit.js.out b/tests/specs/run/proto_exploit/proto_exploit.js.out
similarity index 100%
rename from tests/testdata/run/proto_exploit.js.out
rename to tests/specs/run/proto_exploit/proto_exploit.js.out
diff --git a/tests/specs/run/queue_microtask_error/__test__.jsonc b/tests/specs/run/queue_microtask_error/__test__.jsonc
new file mode 100644
index 0000000000..30821d67f6
--- /dev/null
+++ b/tests/specs/run/queue_microtask_error/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet queue_microtask_error.ts",
+  "output": "queue_microtask_error.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/queue_microtask_error.ts b/tests/specs/run/queue_microtask_error/queue_microtask_error.ts
similarity index 100%
rename from tests/testdata/run/queue_microtask_error.ts
rename to tests/specs/run/queue_microtask_error/queue_microtask_error.ts
diff --git a/tests/testdata/run/queue_microtask_error.ts.out b/tests/specs/run/queue_microtask_error/queue_microtask_error.ts.out
similarity index 100%
rename from tests/testdata/run/queue_microtask_error.ts.out
rename to tests/specs/run/queue_microtask_error/queue_microtask_error.ts.out
diff --git a/tests/specs/run/queue_microtask_error_handled/__test__.jsonc b/tests/specs/run/queue_microtask_error_handled/__test__.jsonc
new file mode 100644
index 0000000000..c343acfb41
--- /dev/null
+++ b/tests/specs/run/queue_microtask_error_handled/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet queue_microtask_error_handled.ts",
+  "output": "queue_microtask_error_handled.ts.out"
+}
diff --git a/tests/testdata/run/queue_microtask_error_handled.ts b/tests/specs/run/queue_microtask_error_handled/queue_microtask_error_handled.ts
similarity index 100%
rename from tests/testdata/run/queue_microtask_error_handled.ts
rename to tests/specs/run/queue_microtask_error_handled/queue_microtask_error_handled.ts
diff --git a/tests/testdata/run/queue_microtask_error_handled.ts.out b/tests/specs/run/queue_microtask_error_handled/queue_microtask_error_handled.ts.out
similarity index 100%
rename from tests/testdata/run/queue_microtask_error_handled.ts.out
rename to tests/specs/run/queue_microtask_error_handled/queue_microtask_error_handled.ts.out
diff --git a/tests/specs/run/reference_types/__test__.jsonc b/tests/specs/run/reference_types/__test__.jsonc
new file mode 100644
index 0000000000..4e4bd08b89
--- /dev/null
+++ b/tests/specs/run/reference_types/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload --quiet reference_types.ts",
+  "output": "reference_types.ts.out"
+}
diff --git a/tests/testdata/run/reference_types.ts b/tests/specs/run/reference_types/reference_types.ts
similarity index 100%
rename from tests/testdata/run/reference_types.ts
rename to tests/specs/run/reference_types/reference_types.ts
diff --git a/tests/testdata/run/reference_types_remote.ts.out b/tests/specs/run/reference_types/reference_types.ts.out
similarity index 100%
rename from tests/testdata/run/reference_types_remote.ts.out
rename to tests/specs/run/reference_types/reference_types.ts.out
diff --git a/tests/specs/run/reference_types_error/__test__.jsonc b/tests/specs/run/reference_types_error/__test__.jsonc
new file mode 100644
index 0000000000..08450acc10
--- /dev/null
+++ b/tests/specs/run/reference_types_error/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --config checkjs.tsconfig.json --check reference_types_error.js",
+  "output": "reference_types_error.js.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/reference_types_error/checkjs.tsconfig.json b/tests/specs/run/reference_types_error/checkjs.tsconfig.json
new file mode 100644
index 0000000000..08ac60b6cd
--- /dev/null
+++ b/tests/specs/run/reference_types_error/checkjs.tsconfig.json
@@ -0,0 +1,5 @@
+{
+  "compilerOptions": {
+    "checkJs": true
+  }
+}
diff --git a/tests/testdata/run/reference_types_error.js b/tests/specs/run/reference_types_error/reference_types_error.js
similarity index 100%
rename from tests/testdata/run/reference_types_error.js
rename to tests/specs/run/reference_types_error/reference_types_error.js
diff --git a/tests/testdata/run/reference_types_error.js.out b/tests/specs/run/reference_types_error/reference_types_error.js.out
similarity index 100%
rename from tests/testdata/run/reference_types_error.js.out
rename to tests/specs/run/reference_types_error/reference_types_error.js.out
diff --git a/tests/specs/run/reference_types_error_no_check/__test__.jsonc b/tests/specs/run/reference_types_error_no_check/__test__.jsonc
new file mode 100644
index 0000000000..78744759d1
--- /dev/null
+++ b/tests/specs/run/reference_types_error_no_check/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --no-check reference_types_error.js",
+  "output": ""
+}
diff --git a/tests/specs/run/reference_types_error_no_check/reference_types_error.js b/tests/specs/run/reference_types_error_no_check/reference_types_error.js
new file mode 100644
index 0000000000..68b6c21364
--- /dev/null
+++ b/tests/specs/run/reference_types_error_no_check/reference_types_error.js
@@ -0,0 +1,2 @@
+/// <reference types="./nonexistent.d.ts" />
+export const a = 1;
diff --git a/tests/specs/run/reference_types_error_vendor_dir/__test__.jsonc b/tests/specs/run/reference_types_error_vendor_dir/__test__.jsonc
new file mode 100644
index 0000000000..c48dd1d5e1
--- /dev/null
+++ b/tests/specs/run/reference_types_error_vendor_dir/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --config checkjs.tsconfig.json --check --vendor reference_types_error.js",
+  "output": "reference_types_error.js.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/reference_types_error_vendor_dir/checkjs.tsconfig.json b/tests/specs/run/reference_types_error_vendor_dir/checkjs.tsconfig.json
new file mode 100644
index 0000000000..08ac60b6cd
--- /dev/null
+++ b/tests/specs/run/reference_types_error_vendor_dir/checkjs.tsconfig.json
@@ -0,0 +1,5 @@
+{
+  "compilerOptions": {
+    "checkJs": true
+  }
+}
diff --git a/tests/specs/run/reference_types_error_vendor_dir/reference_types_error.js b/tests/specs/run/reference_types_error_vendor_dir/reference_types_error.js
new file mode 100644
index 0000000000..68b6c21364
--- /dev/null
+++ b/tests/specs/run/reference_types_error_vendor_dir/reference_types_error.js
@@ -0,0 +1,2 @@
+/// <reference types="./nonexistent.d.ts" />
+export const a = 1;
diff --git a/tests/specs/run/reference_types_error_vendor_dir/reference_types_error.js.out b/tests/specs/run/reference_types_error_vendor_dir/reference_types_error.js.out
new file mode 100644
index 0000000000..86055f3ac3
--- /dev/null
+++ b/tests/specs/run/reference_types_error_vendor_dir/reference_types_error.js.out
@@ -0,0 +1,2 @@
+error: Module not found "file:///[WILDCARD]/nonexistent.d.ts".
+    at file:///[WILDCARD]/reference_types_error.js:1:22
diff --git a/tests/specs/run/references_types_remote/__test__.jsonc b/tests/specs/run/references_types_remote/__test__.jsonc
new file mode 100644
index 0000000000..3f7f27c268
--- /dev/null
+++ b/tests/specs/run/references_types_remote/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload --quiet reference_types_remote.ts",
+  "output": "reference_types_remote.ts.out"
+}
diff --git a/tests/testdata/run/reference_types_remote.ts b/tests/specs/run/references_types_remote/reference_types_remote.ts
similarity index 100%
rename from tests/testdata/run/reference_types_remote.ts
rename to tests/specs/run/references_types_remote/reference_types_remote.ts
diff --git a/tests/specs/run/references_types_remote/reference_types_remote.ts.out b/tests/specs/run/references_types_remote/reference_types_remote.ts.out
new file mode 100644
index 0000000000..417b7b5370
--- /dev/null
+++ b/tests/specs/run/references_types_remote/reference_types_remote.ts.out
@@ -0,0 +1 @@
+undefined
diff --git a/tests/specs/run/rejection_handled/__test__.jsonc b/tests/specs/run/rejection_handled/__test__.jsonc
new file mode 100644
index 0000000000..7565a7dd10
--- /dev/null
+++ b/tests/specs/run/rejection_handled/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --check rejection_handled.ts",
+  "output": "rejection_handled.out"
+}
diff --git a/tests/testdata/run/rejection_handled.out b/tests/specs/run/rejection_handled/rejection_handled.out
similarity index 100%
rename from tests/testdata/run/rejection_handled.out
rename to tests/specs/run/rejection_handled/rejection_handled.out
diff --git a/tests/testdata/run/rejection_handled.ts b/tests/specs/run/rejection_handled/rejection_handled.ts
similarity index 100%
rename from tests/testdata/run/rejection_handled.ts
rename to tests/specs/run/rejection_handled/rejection_handled.ts
diff --git a/tests/specs/run/remote_cjs_main/__test__.jsonc b/tests/specs/run/remote_cjs_main/__test__.jsonc
new file mode 100644
index 0000000000..f45d09406e
--- /dev/null
+++ b/tests/specs/run/remote_cjs_main/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run http://localhost:4545/run/add.cjs",
+  "output": "output.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/remote_cjs_main/output.out b/tests/specs/run/remote_cjs_main/output.out
new file mode 100644
index 0000000000..360934acb7
--- /dev/null
+++ b/tests/specs/run/remote_cjs_main/output.out
@@ -0,0 +1,3 @@
+Download http://localhost:4545/run/add.cjs
+error: Remote CJS modules are not supported.
+  Specifier: http://localhost:4545/run/add.cjs
diff --git a/tests/specs/run/replace_self/__test__.jsonc b/tests/specs/run/replace_self/__test__.jsonc
new file mode 100644
index 0000000000..cfadbf7918
--- /dev/null
+++ b/tests/specs/run/replace_self/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run replace_self.js",
+  "output": "replace_self.js.out"
+}
diff --git a/tests/testdata/run/replace_self.js b/tests/specs/run/replace_self/replace_self.js
similarity index 100%
rename from tests/testdata/run/replace_self.js
rename to tests/specs/run/replace_self/replace_self.js
diff --git a/tests/testdata/run/replace_self.js.out b/tests/specs/run/replace_self/replace_self.js.out
similarity index 100%
rename from tests/testdata/run/replace_self.js.out
rename to tests/specs/run/replace_self/replace_self.js.out
diff --git a/tests/specs/run/report_error/__test__.jsonc b/tests/specs/run/report_error/__test__.jsonc
new file mode 100644
index 0000000000..0577ad2450
--- /dev/null
+++ b/tests/specs/run/report_error/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet report_error.ts",
+  "output": "report_error.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/report_error.ts b/tests/specs/run/report_error/report_error.ts
similarity index 100%
rename from tests/testdata/run/report_error.ts
rename to tests/specs/run/report_error/report_error.ts
diff --git a/tests/testdata/run/report_error.ts.out b/tests/specs/run/report_error/report_error.ts.out
similarity index 100%
rename from tests/testdata/run/report_error.ts.out
rename to tests/specs/run/report_error/report_error.ts.out
diff --git a/tests/specs/run/report_error_end_of_program/__test__.jsonc b/tests/specs/run/report_error_end_of_program/__test__.jsonc
new file mode 100644
index 0000000000..c34956b74a
--- /dev/null
+++ b/tests/specs/run/report_error_end_of_program/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet report_error_end_of_program.ts",
+  "output": "report_error_end_of_program.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/report_error_end_of_program.ts b/tests/specs/run/report_error_end_of_program/report_error_end_of_program.ts
similarity index 100%
rename from tests/testdata/run/report_error_end_of_program.ts
rename to tests/specs/run/report_error_end_of_program/report_error_end_of_program.ts
diff --git a/tests/testdata/run/report_error_end_of_program.ts.out b/tests/specs/run/report_error_end_of_program/report_error_end_of_program.ts.out
similarity index 100%
rename from tests/testdata/run/report_error_end_of_program.ts.out
rename to tests/specs/run/report_error_end_of_program/report_error_end_of_program.ts.out
diff --git a/tests/specs/run/report_error_handled/__test__.jsonc b/tests/specs/run/report_error_handled/__test__.jsonc
new file mode 100644
index 0000000000..126687b95e
--- /dev/null
+++ b/tests/specs/run/report_error_handled/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet report_error_handled.ts",
+  "output": "report_error_handled.ts.out"
+}
diff --git a/tests/testdata/run/report_error_handled.ts b/tests/specs/run/report_error_handled/report_error_handled.ts
similarity index 100%
rename from tests/testdata/run/report_error_handled.ts
rename to tests/specs/run/report_error_handled/report_error_handled.ts
diff --git a/tests/testdata/run/report_error_handled.ts.out b/tests/specs/run/report_error_handled/report_error_handled.ts.out
similarity index 100%
rename from tests/testdata/run/report_error_handled.ts.out
rename to tests/specs/run/report_error_handled/report_error_handled.ts.out
diff --git a/tests/specs/run/require_esm/main.out b/tests/specs/run/require_esm/main.out
index d17b1ead55..4890e1a492 100644
--- a/tests/specs/run/require_esm/main.out
+++ b/tests/specs/run/require_esm/main.out
@@ -1,13 +1,4 @@
 [Module: null prototype] { sync_js: 1 }
 [Module: null prototype] { sync_mjs: 1 }
-error: Uncaught Error: Top-level await is not allowed in synchronous evaluation
-    at loadESMFromCJS (node:module:[WILDCARD])
-    at Module._compile (node:module:[WILDCARD])
-    at Object.Module._extensions..js (node:module:[WILDCARD])
-    at Module.load (node:module:[WILDCARD])
-    at Function.Module._load (node:module:[WILDCARD])
-    at Module.require (node:module:[WILDCARD])
-    at require (node:module:[WILDCARD])
-    at Object.<anonymous> (file:[WILDCARD]/tests/specs/run/require_esm/main.cjs:[WILDCARD])
-    at Object.<anonymous> (file:[WILDCARD]/tests/specs/run/require_esm/main.cjs:[WILDCARD])
-    at Module._compile (node:module:[WILDCARD])
+error: Uncaught (in promise) Error: Top-level await is not allowed in synchronous evaluation
+    at [WILDCARD]
diff --git a/tests/specs/run/runtime_decorators/__test__.jsonc b/tests/specs/run/runtime_decorators/__test__.jsonc
new file mode 100644
index 0000000000..286fd377d8
--- /dev/null
+++ b/tests/specs/run/runtime_decorators/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --no-check decorators/experimental/runtime/main.ts",
+  "output": "decorators/experimental/runtime/main.out"
+}
diff --git a/tests/specs/run/runtime_decorators/decorators/experimental/deno.json b/tests/specs/run/runtime_decorators/decorators/experimental/deno.json
new file mode 100644
index 0000000000..504cd646e1
--- /dev/null
+++ b/tests/specs/run/runtime_decorators/decorators/experimental/deno.json
@@ -0,0 +1,5 @@
+{
+  "compilerOptions": {
+    "experimentalDecorators": true
+  }
+}
diff --git a/tests/specs/run/runtime_decorators/decorators/experimental/no_check/main.out b/tests/specs/run/runtime_decorators/decorators/experimental/no_check/main.out
new file mode 100644
index 0000000000..015f7076e8
--- /dev/null
+++ b/tests/specs/run/runtime_decorators/decorators/experimental/no_check/main.out
@@ -0,0 +1,3 @@
+a(): evaluated
+a(): called
+method
diff --git a/tests/specs/run/runtime_decorators/decorators/experimental/no_check/main.ts b/tests/specs/run/runtime_decorators/decorators/experimental/no_check/main.ts
new file mode 100644
index 0000000000..9f7ec550d5
--- /dev/null
+++ b/tests/specs/run/runtime_decorators/decorators/experimental/no_check/main.ts
@@ -0,0 +1,21 @@
+// deno-lint-ignore-file
+function a() {
+  console.log("a(): evaluated");
+  return (
+    _target: any,
+    _propertyKey: string,
+    _descriptor: PropertyDescriptor,
+  ) => {
+    console.log("a(): called");
+  };
+}
+
+class B {
+  @a()
+  method() {
+    console.log("method");
+  }
+}
+
+const b = new B();
+b.method();
diff --git a/tests/specs/run/runtime_decorators/decorators/experimental/runtime/main.out b/tests/specs/run/runtime_decorators/decorators/experimental/runtime/main.out
new file mode 100644
index 0000000000..0fc1d4590e
--- /dev/null
+++ b/tests/specs/run/runtime_decorators/decorators/experimental/runtime/main.out
@@ -0,0 +1,7 @@
+@A evaluated
+@B evaluated
+@B called
+@A called
+fn() called from @A
+fn() called from @B
+C.test() called
diff --git a/tests/specs/run/runtime_decorators/decorators/experimental/runtime/main.ts b/tests/specs/run/runtime_decorators/decorators/experimental/runtime/main.ts
new file mode 100644
index 0000000000..40a26bbd4d
--- /dev/null
+++ b/tests/specs/run/runtime_decorators/decorators/experimental/runtime/main.ts
@@ -0,0 +1,42 @@
+// deno-lint-ignore-file
+function a() {
+  console.log("@A evaluated");
+  return function (
+    target: any,
+    propertyKey: string,
+    descriptor: PropertyDescriptor,
+  ) {
+    console.log("@A called");
+    const fn = descriptor.value;
+    descriptor.value = function () {
+      console.log("fn() called from @A");
+      fn();
+    };
+  };
+}
+
+function b() {
+  console.log("@B evaluated");
+  return function (
+    target: any,
+    propertyKey: string,
+    descriptor: PropertyDescriptor,
+  ) {
+    console.log("@B called");
+    const fn = descriptor.value;
+    descriptor.value = function () {
+      console.log("fn() called from @B");
+      fn();
+    };
+  };
+}
+
+class C {
+  @a()
+  @b()
+  static test() {
+    console.log("C.test() called");
+  }
+}
+
+C.test();
diff --git a/tests/specs/run/runtime_decorators/decorators/experimental/ts/main.out b/tests/specs/run/runtime_decorators/decorators/experimental/ts/main.out
new file mode 100644
index 0000000000..ea64fbaa63
--- /dev/null
+++ b/tests/specs/run/runtime_decorators/decorators/experimental/ts/main.out
@@ -0,0 +1,3 @@
+Warning experimentalDecorators compiler option is deprecated and may be removed at any time
+Check [WILDCARD]
+SomeClass { someField: "asdf" }
diff --git a/tests/specs/run/runtime_decorators/decorators/experimental/ts/main.ts b/tests/specs/run/runtime_decorators/decorators/experimental/ts/main.ts
new file mode 100644
index 0000000000..95fba6cd48
--- /dev/null
+++ b/tests/specs/run/runtime_decorators/decorators/experimental/ts/main.ts
@@ -0,0 +1,14 @@
+// deno-lint-ignore-file
+
+function Decorate() {
+  return function (constructor: any): any {
+    return class extends constructor {
+      protected someField: string = "asdf";
+    };
+  };
+}
+
+@Decorate()
+class SomeClass {}
+
+console.log(new SomeClass());
diff --git a/tests/specs/run/runtime_decorators/decorators/tc39_proposal/main.out b/tests/specs/run/runtime_decorators/decorators/tc39_proposal/main.out
new file mode 100644
index 0000000000..39394952e8
--- /dev/null
+++ b/tests/specs/run/runtime_decorators/decorators/tc39_proposal/main.out
@@ -0,0 +1,3 @@
+starting m with arguments 1
+C.m 1
+ending m
diff --git a/tests/specs/run/runtime_decorators/decorators/tc39_proposal/main.ts b/tests/specs/run/runtime_decorators/decorators/tc39_proposal/main.ts
new file mode 100644
index 0000000000..00c8a85025
--- /dev/null
+++ b/tests/specs/run/runtime_decorators/decorators/tc39_proposal/main.ts
@@ -0,0 +1,21 @@
+// deno-lint-ignore no-explicit-any
+function logged(value: any, { kind, name }: { kind: string; name: string }) {
+  if (kind === "method") {
+    return function (...args: unknown[]) {
+      console.log(`starting ${name} with arguments ${args.join(", ")}`);
+      // @ts-ignore this has implicit any type
+      const ret = value.call(this, ...args);
+      console.log(`ending ${name}`);
+      return ret;
+    };
+  }
+}
+
+class C {
+  @logged
+  m(arg: number) {
+    console.log("C.m", arg);
+  }
+}
+
+new C().m(1);
diff --git a/tests/specs/run/seed_random/__test__.jsonc b/tests/specs/run/seed_random/__test__.jsonc
new file mode 100644
index 0000000000..5a1876d6c3
--- /dev/null
+++ b/tests/specs/run/seed_random/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --seed=100 seed_random.js",
+  "output": "seed_random.js.out"
+}
diff --git a/tests/testdata/run/seed_random.js b/tests/specs/run/seed_random/seed_random.js
similarity index 100%
rename from tests/testdata/run/seed_random.js
rename to tests/specs/run/seed_random/seed_random.js
diff --git a/tests/testdata/run/seed_random.js.out b/tests/specs/run/seed_random/seed_random.js.out
similarity index 100%
rename from tests/testdata/run/seed_random.js.out
rename to tests/specs/run/seed_random/seed_random.js.out
diff --git a/tests/specs/run/set_exit_code_0/__test__.jsonc b/tests/specs/run/set_exit_code_0/__test__.jsonc
new file mode 100644
index 0000000000..a5866e8c69
--- /dev/null
+++ b/tests/specs/run/set_exit_code_0/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --no-check set_exit_code_0.ts",
+  "output": "",
+  "exitCode": 0
+}
diff --git a/tests/testdata/run/set_exit_code_0.ts b/tests/specs/run/set_exit_code_0/set_exit_code_0.ts
similarity index 100%
rename from tests/testdata/run/set_exit_code_0.ts
rename to tests/specs/run/set_exit_code_0/set_exit_code_0.ts
diff --git a/tests/specs/run/set_exit_code_1/__test__.jsonc b/tests/specs/run/set_exit_code_1/__test__.jsonc
new file mode 100644
index 0000000000..1ca50c9827
--- /dev/null
+++ b/tests/specs/run/set_exit_code_1/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --no-check set_exit_code_1.ts",
+  "output": "",
+  "exitCode": 42
+}
diff --git a/tests/testdata/run/set_exit_code_1.ts b/tests/specs/run/set_exit_code_1/set_exit_code_1.ts
similarity index 100%
rename from tests/testdata/run/set_exit_code_1.ts
rename to tests/specs/run/set_exit_code_1/set_exit_code_1.ts
diff --git a/tests/specs/run/set_exit_code_2/__test__.jsonc b/tests/specs/run/set_exit_code_2/__test__.jsonc
new file mode 100644
index 0000000000..af7411f7cb
--- /dev/null
+++ b/tests/specs/run/set_exit_code_2/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --no-check set_exit_code_2.ts",
+  "output": "",
+  "exitCode": 42
+}
diff --git a/tests/testdata/run/set_exit_code_2.ts b/tests/specs/run/set_exit_code_2/set_exit_code_2.ts
similarity index 100%
rename from tests/testdata/run/set_exit_code_2.ts
rename to tests/specs/run/set_exit_code_2/set_exit_code_2.ts
diff --git a/tests/specs/run/set_timeout_error/__test__.jsonc b/tests/specs/run/set_timeout_error/__test__.jsonc
new file mode 100644
index 0000000000..eea730fd87
--- /dev/null
+++ b/tests/specs/run/set_timeout_error/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet set_timeout_error.ts",
+  "output": "set_timeout_error.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/set_timeout_error.ts b/tests/specs/run/set_timeout_error/set_timeout_error.ts
similarity index 100%
rename from tests/testdata/run/set_timeout_error.ts
rename to tests/specs/run/set_timeout_error/set_timeout_error.ts
diff --git a/tests/testdata/run/set_timeout_error.ts.out b/tests/specs/run/set_timeout_error/set_timeout_error.ts.out
similarity index 100%
rename from tests/testdata/run/set_timeout_error.ts.out
rename to tests/specs/run/set_timeout_error/set_timeout_error.ts.out
diff --git a/tests/specs/run/set_timeout_error_handled/__test__.jsonc b/tests/specs/run/set_timeout_error_handled/__test__.jsonc
new file mode 100644
index 0000000000..39a9424bbc
--- /dev/null
+++ b/tests/specs/run/set_timeout_error_handled/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet set_timeout_error_handled.ts",
+  "output": "set_timeout_error_handled.ts.out"
+}
diff --git a/tests/testdata/run/set_timeout_error_handled.ts b/tests/specs/run/set_timeout_error_handled/set_timeout_error_handled.ts
similarity index 100%
rename from tests/testdata/run/set_timeout_error_handled.ts
rename to tests/specs/run/set_timeout_error_handled/set_timeout_error_handled.ts
diff --git a/tests/testdata/run/set_timeout_error_handled.ts.out b/tests/specs/run/set_timeout_error_handled/set_timeout_error_handled.ts.out
similarity index 100%
rename from tests/testdata/run/set_timeout_error_handled.ts.out
rename to tests/specs/run/set_timeout_error_handled/set_timeout_error_handled.ts.out
diff --git a/tests/specs/run/shebang_swc/__test__.jsonc b/tests/specs/run/shebang_swc/__test__.jsonc
new file mode 100644
index 0000000000..65e0b5c9b1
--- /dev/null
+++ b/tests/specs/run/shebang_swc/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet shebang.ts",
+  "output": "shebang.ts.out"
+}
diff --git a/tests/testdata/run/shebang.ts b/tests/specs/run/shebang_swc/shebang.ts
similarity index 100%
rename from tests/testdata/run/shebang.ts
rename to tests/specs/run/shebang_swc/shebang.ts
diff --git a/tests/testdata/run/shebang.ts.out b/tests/specs/run/shebang_swc/shebang.ts.out
similarity index 100%
rename from tests/testdata/run/shebang.ts.out
rename to tests/specs/run/shebang_swc/shebang.ts.out
diff --git a/tests/specs/run/shebang_swc/shebang2.ts b/tests/specs/run/shebang_swc/shebang2.ts
new file mode 100644
index 0000000000..da0d7bf0c9
--- /dev/null
+++ b/tests/specs/run/shebang_swc/shebang2.ts
@@ -0,0 +1,3 @@
+#!/usr/bin/env -S deno run
+
+export default 42;
diff --git a/tests/specs/run/shebang_tsc/__test__.jsonc b/tests/specs/run/shebang_tsc/__test__.jsonc
new file mode 100644
index 0000000000..f78971d57d
--- /dev/null
+++ b/tests/specs/run/shebang_tsc/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --check shebang.ts",
+  "output": "shebang.ts.out"
+}
diff --git a/tests/specs/run/shebang_tsc/shebang.ts b/tests/specs/run/shebang_tsc/shebang.ts
new file mode 100644
index 0000000000..00feb2da0a
--- /dev/null
+++ b/tests/specs/run/shebang_tsc/shebang.ts
@@ -0,0 +1,5 @@
+#!/usr/bin/env -S deno run
+
+import test from "./shebang2.ts";
+
+console.log(test as number);
diff --git a/tests/testdata/run/wasm.ts.out b/tests/specs/run/shebang_tsc/shebang.ts.out
similarity index 100%
rename from tests/testdata/run/wasm.ts.out
rename to tests/specs/run/shebang_tsc/shebang.ts.out
diff --git a/tests/specs/run/shebang_tsc/shebang2.ts b/tests/specs/run/shebang_tsc/shebang2.ts
new file mode 100644
index 0000000000..da0d7bf0c9
--- /dev/null
+++ b/tests/specs/run/shebang_tsc/shebang2.ts
@@ -0,0 +1,3 @@
+#!/usr/bin/env -S deno run
+
+export default 42;
diff --git a/tests/specs/run/shebang_with_json_imports_swc/__test__.jsonc b/tests/specs/run/shebang_with_json_imports_swc/__test__.jsonc
new file mode 100644
index 0000000000..90592757fe
--- /dev/null
+++ b/tests/specs/run/shebang_with_json_imports_swc/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --no-check json_with_shebang.ts",
+  "output": "json_with_shebang.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/shebang_with_json_imports_swc/json_with_shebang.json b/tests/specs/run/shebang_with_json_imports_swc/json_with_shebang.json
new file mode 100644
index 0000000000..b695e44571
--- /dev/null
+++ b/tests/specs/run/shebang_with_json_imports_swc/json_with_shebang.json
@@ -0,0 +1,4 @@
+#!/usr/env -S deno run
+{
+  "test": null
+}
diff --git a/tests/specs/run/shebang_with_json_imports_swc/json_with_shebang.ts b/tests/specs/run/shebang_with_json_imports_swc/json_with_shebang.ts
new file mode 100644
index 0000000000..9524026bce
--- /dev/null
+++ b/tests/specs/run/shebang_with_json_imports_swc/json_with_shebang.ts
@@ -0,0 +1,3 @@
+import json from "./json_with_shebang.json" with { type: "json" };
+
+console.log(json);
diff --git a/tests/specs/run/shebang_with_json_imports_swc/json_with_shebang.ts.out b/tests/specs/run/shebang_with_json_imports_swc/json_with_shebang.ts.out
new file mode 100644
index 0000000000..23eb03720e
--- /dev/null
+++ b/tests/specs/run/shebang_with_json_imports_swc/json_with_shebang.ts.out
@@ -0,0 +1 @@
+error: Uncaught SyntaxError: Unexpected token '#', "#!/usr/env"... is not valid JSON
diff --git a/tests/specs/run/shebang_with_json_imports_tsc/__test__.jsonc b/tests/specs/run/shebang_with_json_imports_tsc/__test__.jsonc
new file mode 100644
index 0000000000..7fbb8a5d35
--- /dev/null
+++ b/tests/specs/run/shebang_with_json_imports_tsc/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet json_with_shebang.ts",
+  "output": "json_with_shebang.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/shebang_with_json_imports_tsc/json_with_shebang.json b/tests/specs/run/shebang_with_json_imports_tsc/json_with_shebang.json
new file mode 100644
index 0000000000..b695e44571
--- /dev/null
+++ b/tests/specs/run/shebang_with_json_imports_tsc/json_with_shebang.json
@@ -0,0 +1,4 @@
+#!/usr/env -S deno run
+{
+  "test": null
+}
diff --git a/tests/specs/run/shebang_with_json_imports_tsc/json_with_shebang.ts b/tests/specs/run/shebang_with_json_imports_tsc/json_with_shebang.ts
new file mode 100644
index 0000000000..9524026bce
--- /dev/null
+++ b/tests/specs/run/shebang_with_json_imports_tsc/json_with_shebang.ts
@@ -0,0 +1,3 @@
+import json from "./json_with_shebang.json" with { type: "json" };
+
+console.log(json);
diff --git a/tests/specs/run/shebang_with_json_imports_tsc/json_with_shebang.ts.out b/tests/specs/run/shebang_with_json_imports_tsc/json_with_shebang.ts.out
new file mode 100644
index 0000000000..23eb03720e
--- /dev/null
+++ b/tests/specs/run/shebang_with_json_imports_tsc/json_with_shebang.ts.out
@@ -0,0 +1 @@
+error: Uncaught SyntaxError: Unexpected token '#', "#!/usr/env"... is not valid JSON
diff --git a/tests/specs/run/single_compile_with_reload/__test__.jsonc b/tests/specs/run/single_compile_with_reload/__test__.jsonc
new file mode 100644
index 0000000000..3e2e043790
--- /dev/null
+++ b/tests/specs/run/single_compile_with_reload/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload --allow-read single_compile_with_reload.ts",
+  "output": "single_compile_with_reload.ts.out"
+}
diff --git a/tests/specs/run/single_compile_with_reload/mod1.ts b/tests/specs/run/single_compile_with_reload/mod1.ts
new file mode 100644
index 0000000000..5e58f432ed
--- /dev/null
+++ b/tests/specs/run/single_compile_with_reload/mod1.ts
@@ -0,0 +1,17 @@
+import { printHello2, returnsFoo } from "./subdir2/mod2.ts";
+
+export function returnsHi(): string {
+  return "Hi";
+}
+
+export function returnsFoo2(): string {
+  return returnsFoo();
+}
+
+export function printHello3() {
+  printHello2();
+}
+
+export function throwsError() {
+  throw Error("exception from mod1");
+}
diff --git a/tests/specs/run/single_compile_with_reload/print_hello.ts b/tests/specs/run/single_compile_with_reload/print_hello.ts
new file mode 100644
index 0000000000..b9c0ad5275
--- /dev/null
+++ b/tests/specs/run/single_compile_with_reload/print_hello.ts
@@ -0,0 +1,3 @@
+export function printHello() {
+  console.log("Hello");
+}
diff --git a/tests/testdata/run/single_compile_with_reload.ts b/tests/specs/run/single_compile_with_reload/single_compile_with_reload.ts
similarity index 100%
rename from tests/testdata/run/single_compile_with_reload.ts
rename to tests/specs/run/single_compile_with_reload/single_compile_with_reload.ts
diff --git a/tests/testdata/run/single_compile_with_reload.ts.out b/tests/specs/run/single_compile_with_reload/single_compile_with_reload.ts.out
similarity index 100%
rename from tests/testdata/run/single_compile_with_reload.ts.out
rename to tests/specs/run/single_compile_with_reload/single_compile_with_reload.ts.out
diff --git a/tests/specs/run/single_compile_with_reload/single_compile_with_reload_dyn.ts b/tests/specs/run/single_compile_with_reload/single_compile_with_reload_dyn.ts
new file mode 100644
index 0000000000..c69556be15
--- /dev/null
+++ b/tests/specs/run/single_compile_with_reload/single_compile_with_reload_dyn.ts
@@ -0,0 +1,11 @@
+import { printHello3, returnsFoo2, returnsHi } from "./mod1.ts";
+
+printHello3();
+
+if (returnsHi() !== "Hi") {
+  throw Error("Unexpected");
+}
+
+if (returnsFoo2() !== "Foo") {
+  throw Error("Unexpected");
+}
diff --git a/tests/specs/run/single_compile_with_reload/single_compile_with_reload_worker.ts b/tests/specs/run/single_compile_with_reload/single_compile_with_reload_worker.ts
new file mode 100644
index 0000000000..103cafe20c
--- /dev/null
+++ b/tests/specs/run/single_compile_with_reload/single_compile_with_reload_worker.ts
@@ -0,0 +1,3 @@
+console.log("Hello from worker");
+postMessage(null);
+close();
diff --git a/tests/specs/run/single_compile_with_reload/subdir2/dynamic_import.ts b/tests/specs/run/single_compile_with_reload/subdir2/dynamic_import.ts
new file mode 100644
index 0000000000..59beb64c33
--- /dev/null
+++ b/tests/specs/run/single_compile_with_reload/subdir2/dynamic_import.ts
@@ -0,0 +1,4 @@
+(async () => {
+  const { printHello } = await import("../mod2.ts");
+  printHello();
+})();
diff --git a/tests/specs/run/single_compile_with_reload/subdir2/mod2.ts b/tests/specs/run/single_compile_with_reload/subdir2/mod2.ts
new file mode 100644
index 0000000000..9071d0aeb4
--- /dev/null
+++ b/tests/specs/run/single_compile_with_reload/subdir2/mod2.ts
@@ -0,0 +1,9 @@
+import { printHello } from "../print_hello.ts";
+
+export function returnsFoo(): string {
+  return "Foo";
+}
+
+export function printHello2() {
+  printHello();
+}
diff --git a/tests/specs/run/spawn_stdout_inherit/__test__.jsonc b/tests/specs/run/spawn_stdout_inherit/__test__.jsonc
new file mode 100644
index 0000000000..4dd5fe54ce
--- /dev/null
+++ b/tests/specs/run/spawn_stdout_inherit/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet -A spawn_stdout_inherit.ts",
+  "output": "spawn_stdout_inherit.ts.out"
+}
diff --git a/tests/testdata/run/spawn_stdout_inherit.ts b/tests/specs/run/spawn_stdout_inherit/spawn_stdout_inherit.ts
similarity index 100%
rename from tests/testdata/run/spawn_stdout_inherit.ts
rename to tests/specs/run/spawn_stdout_inherit/spawn_stdout_inherit.ts
diff --git a/tests/testdata/run/spawn_stdout_inherit.ts.out b/tests/specs/run/spawn_stdout_inherit/spawn_stdout_inherit.ts.out
similarity index 100%
rename from tests/testdata/run/spawn_stdout_inherit.ts.out
rename to tests/specs/run/spawn_stdout_inherit/spawn_stdout_inherit.ts.out
diff --git a/tests/specs/run/stdin_read_all/__test__.jsonc b/tests/specs/run/stdin_read_all/__test__.jsonc
new file mode 100644
index 0000000000..6fc035aabd
--- /dev/null
+++ b/tests/specs/run/stdin_read_all/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet stdin_read_all.ts",
+  "output": "stdin_read_all.out",
+  "input": "01234567890123456789012345678901234567890123456789"
+}
diff --git a/tests/testdata/run/stdin_read_all.out b/tests/specs/run/stdin_read_all/stdin_read_all.out
similarity index 100%
rename from tests/testdata/run/stdin_read_all.out
rename to tests/specs/run/stdin_read_all/stdin_read_all.out
diff --git a/tests/testdata/run/stdin_read_all.ts b/tests/specs/run/stdin_read_all/stdin_read_all.ts
similarity index 100%
rename from tests/testdata/run/stdin_read_all.ts
rename to tests/specs/run/stdin_read_all/stdin_read_all.ts
diff --git a/tests/specs/run/stdin_type_cjs/__test__.jsonc b/tests/specs/run/stdin_type_cjs/__test__.jsonc
new file mode 100644
index 0000000000..e60af4a803
--- /dev/null
+++ b/tests/specs/run/stdin_type_cjs/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet -",
+  "output": "1\n",
+  "input": "console.log(1)"
+}
diff --git a/tests/specs/run/stdin_type_cjs/package.json b/tests/specs/run/stdin_type_cjs/package.json
new file mode 100644
index 0000000000..5bbefffbab
--- /dev/null
+++ b/tests/specs/run/stdin_type_cjs/package.json
@@ -0,0 +1,3 @@
+{
+  "type": "commonjs"
+}
diff --git a/tests/specs/run/stdin_type_cjs/stdin_read_all.ts b/tests/specs/run/stdin_type_cjs/stdin_read_all.ts
new file mode 100644
index 0000000000..2ecae40b71
--- /dev/null
+++ b/tests/specs/run/stdin_type_cjs/stdin_read_all.ts
@@ -0,0 +1 @@
+Deno.stdin.readable.pipeTo(Deno.stdout.writable);
diff --git a/tests/specs/run/stdout_write_all/__test__.jsonc b/tests/specs/run/stdout_write_all/__test__.jsonc
new file mode 100644
index 0000000000..2057f4a115
--- /dev/null
+++ b/tests/specs/run/stdout_write_all/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet stdout_write_all.ts",
+  "output": "stdout_write_all.out"
+}
diff --git a/tests/testdata/run/stdout_write_all.out b/tests/specs/run/stdout_write_all/stdout_write_all.out
similarity index 100%
rename from tests/testdata/run/stdout_write_all.out
rename to tests/specs/run/stdout_write_all/stdout_write_all.out
diff --git a/tests/testdata/run/stdout_write_all.ts b/tests/specs/run/stdout_write_all/stdout_write_all.ts
similarity index 100%
rename from tests/testdata/run/stdout_write_all.ts
rename to tests/specs/run/stdout_write_all/stdout_write_all.ts
diff --git a/tests/specs/run/stdout_write_sync_async/__test__.jsonc b/tests/specs/run/stdout_write_sync_async/__test__.jsonc
new file mode 100644
index 0000000000..5032ca015f
--- /dev/null
+++ b/tests/specs/run/stdout_write_sync_async/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet stdout_write_sync_async.ts",
+  "output": "stdout_write_sync_async.out"
+}
diff --git a/tests/testdata/run/stdout_write_sync_async.out b/tests/specs/run/stdout_write_sync_async/stdout_write_sync_async.out
similarity index 100%
rename from tests/testdata/run/stdout_write_sync_async.out
rename to tests/specs/run/stdout_write_sync_async/stdout_write_sync_async.out
diff --git a/tests/testdata/run/stdout_write_sync_async.ts b/tests/specs/run/stdout_write_sync_async/stdout_write_sync_async.ts
similarity index 100%
rename from tests/testdata/run/stdout_write_sync_async.ts
rename to tests/specs/run/stdout_write_sync_async/stdout_write_sync_async.ts
diff --git a/tests/specs/run/swc_syntax_error/__test__.jsonc b/tests/specs/run/swc_syntax_error/__test__.jsonc
new file mode 100644
index 0000000000..842a4fcf8e
--- /dev/null
+++ b/tests/specs/run/swc_syntax_error/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload --check swc_syntax_error.ts",
+  "output": "swc_syntax_error.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/swc_syntax_error.ts b/tests/specs/run/swc_syntax_error/swc_syntax_error.ts
similarity index 100%
rename from tests/testdata/run/swc_syntax_error.ts
rename to tests/specs/run/swc_syntax_error/swc_syntax_error.ts
diff --git a/tests/testdata/run/swc_syntax_error.ts.out b/tests/specs/run/swc_syntax_error/swc_syntax_error.ts.out
similarity index 100%
rename from tests/testdata/run/swc_syntax_error.ts.out
rename to tests/specs/run/swc_syntax_error/swc_syntax_error.ts.out
diff --git a/tests/specs/run/test_and_bench_are_noops_in_run/__test__.jsonc b/tests/specs/run/test_and_bench_are_noops_in_run/__test__.jsonc
new file mode 100644
index 0000000000..3d8d2ba56e
--- /dev/null
+++ b/tests/specs/run/test_and_bench_are_noops_in_run/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run test_and_bench_in_run.js",
+  "output": ""
+}
diff --git a/tests/testdata/run/test_and_bench_in_run.js b/tests/specs/run/test_and_bench_are_noops_in_run/test_and_bench_in_run.js
similarity index 100%
rename from tests/testdata/run/test_and_bench_in_run.js
rename to tests/specs/run/test_and_bench_are_noops_in_run/test_and_bench_in_run.js
diff --git a/tests/specs/run/tls_connecttls/RootCA.pem b/tests/specs/run/tls_connecttls/RootCA.pem
new file mode 100644
index 0000000000..c2f84ceebc
--- /dev/null
+++ b/tests/specs/run/tls_connecttls/RootCA.pem
@@ -0,0 +1,19 @@
+-----BEGIN CERTIFICATE-----
+MIIDIzCCAgugAwIBAgIJAMKPPW4tsOymMA0GCSqGSIb3DQEBCwUAMCcxCzAJBgNV
+BAYTAlVTMRgwFgYDVQQDDA9FeGFtcGxlLVJvb3QtQ0EwIBcNMTkxMDIxMTYyODIy
+WhgPMjExODA5MjcxNjI4MjJaMCcxCzAJBgNVBAYTAlVTMRgwFgYDVQQDDA9FeGFt
+cGxlLVJvb3QtQ0EwggEiMA0GCSqGSIb3DQEBAQUAA4IBDwAwggEKAoIBAQDMH/IO
+2qtHfyBKwANNPB4K0q5JVSg8XxZdRpTTlz0CwU0oRO3uHrI52raCCfVeiQutyZop
+eFZTDWeXGudGAFA2B5m3orWt0s+touPi8MzjsG2TQ+WSI66QgbXTNDitDDBtTVcV
+5G3Ic+3SppQAYiHSekLISnYWgXLl+k5CnEfTowg6cjqjVr0KjL03cTN3H7b+6+0S
+ws4rYbW1j4ExR7K6BFNH6572yq5qR20E6GqlY+EcOZpw4CbCk9lS8/CWuXze/vMs
+OfDcc6K+B625d27wyEGZHedBomT2vAD7sBjvO8hn/DP1Qb46a8uCHR6NSfnJ7bXO
+G1igaIbgY1zXirNdAgMBAAGjUDBOMB0GA1UdDgQWBBTzut+pwwDfqmMYcI9KNWRD
+hxcIpTAfBgNVHSMEGDAWgBTzut+pwwDfqmMYcI9KNWRDhxcIpTAMBgNVHRMEBTAD
+AQH/MA0GCSqGSIb3DQEBCwUAA4IBAQB9AqSbZ+hEglAgSHxAMCqRFdhVu7MvaQM0
+P090mhGlOCt3yB7kdGfsIrUW6nQcTz7PPQFRaJMrFHPvFvPootkBUpTYR4hTkdce
+H6RCRu2Jxl4Y9bY/uezd9YhGCYfUtfjA6/TH9FcuZfttmOOlxOt01XfNvVMIR6RM
+z/AYhd+DeOXjr35F/VHeVpnk+55L0PYJsm1CdEbOs5Hy1ecR7ACuDkXnbM4fpz9I
+kyIWJwk2zJReKcJMgi1aIinDM9ao/dca1G99PHOw8dnr4oyoTiv8ao6PWiSRHHMi
+MNf4EgWfK+tZMnuqfpfO9740KzfcVoMNo4QJD4yn5YxroUOO/Azi
+-----END CERTIFICATE-----
diff --git a/tests/specs/run/tls_connecttls/__test__.jsonc b/tests/specs/run/tls_connecttls/__test__.jsonc
new file mode 100644
index 0000000000..2e8f88339d
--- /dev/null
+++ b/tests/specs/run/tls_connecttls/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-net --allow-read --cert RootCA.pem --config deno.json tls_connecttls.js",
+  "output": "tls.out"
+}
diff --git a/tests/specs/run/tls_connecttls/deno.json b/tests/specs/run/tls_connecttls/deno.json
new file mode 100644
index 0000000000..105514e133
--- /dev/null
+++ b/tests/specs/run/tls_connecttls/deno.json
@@ -0,0 +1,4 @@
+{
+  "lock": false,
+  "importMap": "../../../../import_map.json"
+}
diff --git a/tests/specs/run/tls_connecttls/localhost.crt b/tests/specs/run/tls_connecttls/localhost.crt
new file mode 100644
index 0000000000..a71ae9050f
--- /dev/null
+++ b/tests/specs/run/tls_connecttls/localhost.crt
@@ -0,0 +1,21 @@
+-----BEGIN CERTIFICATE-----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+-----END CERTIFICATE-----
diff --git a/tests/specs/run/tls_connecttls/localhost.key b/tests/specs/run/tls_connecttls/localhost.key
new file mode 100644
index 0000000000..42774c9771
--- /dev/null
+++ b/tests/specs/run/tls_connecttls/localhost.key
@@ -0,0 +1,28 @@
+-----BEGIN PRIVATE KEY-----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+-----END PRIVATE KEY-----
diff --git a/tests/specs/run/tls_connecttls/textproto.ts b/tests/specs/run/tls_connecttls/textproto.ts
new file mode 100644
index 0000000000..9e0f5f5f0a
--- /dev/null
+++ b/tests/specs/run/tls_connecttls/textproto.ts
@@ -0,0 +1,170 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+// Copyright 2009 The Go Authors. All rights reserved.
+// Use of this source code is governed by a BSD-style
+// license that can be found in the LICENSE file.
+
+/** **Deprecated**. Use `TextLineStream` from `std/steams` for line-by-line text reading instead.
+ *
+ * A reader for dealing with low level text based protocols.
+ *
+ * Based on
+ * [net/textproto](https://github.com/golang/go/tree/master/src/net/textproto).
+ *
+ * @deprecated (will be removed after 0.159.0) Use `TextLineStream` from `std/steams` for line-by-line text reading instead.
+ * @module
+ */
+
+import type { BufReader, ReadLineResult } from "@std/io/buf-reader";
+import { concat } from "@std/bytes/concat";
+
+// Constants created for DRY
+const CHAR_SPACE: number = " ".charCodeAt(0);
+const CHAR_TAB: number = "\t".charCodeAt(0);
+const CHAR_COLON: number = ":".charCodeAt(0);
+
+const WHITESPACES: Array<number> = [CHAR_SPACE, CHAR_TAB];
+
+const decoder = new TextDecoder();
+
+// FROM https://github.com/denoland/deno/blob/b34628a26ab0187a827aa4ebe256e23178e25d39/cli/js/web/headers.ts#L9
+const invalidHeaderCharRegex = /[^\t\x20-\x7e\x80-\xff]/g;
+
+function str(buf: Uint8Array | null | undefined): string {
+  return !buf ? "" : decoder.decode(buf);
+}
+
+/**
+ * @deprecated (will be removed after 0.159.0) Use `TextLineStream` from `std/steams` for line-by-line text reading instead.
+ */
+export class TextProtoReader {
+  constructor(readonly r: BufReader) {}
+
+  /** readLine() reads a single line from the TextProtoReader,
+   * eliding the final \n or \r\n from the returned string.
+   */
+  async readLine(): Promise<string | null> {
+    const s = await this.readLineSlice();
+    return s === null ? null : str(s);
+  }
+
+  /** ReadMimeHeader reads a MIME-style header from r.
+   * The header is a sequence of possibly continued Key: Value lines
+   * ending in a blank line.
+   * The returned map m maps CanonicalMIMEHeaderKey(key) to a
+   * sequence of values in the same order encountered in the input.
+   *
+   * For example, consider this input:
+   *
+   * 	My-Key: Value 1
+   * 	Long-Key: Even
+   * 	       Longer Value
+   * 	My-Key: Value 2
+   *
+   * Given that input, ReadMIMEHeader returns the map:
+   *
+   * 	map[string][]string{
+   * 		"My-Key": {"Value 1", "Value 2"},
+   * 		"Long-Key": {"Even Longer Value"},
+   * 	}
+   */
+  async readMimeHeader(): Promise<Headers | null> {
+    const m = new Headers();
+    let line: Uint8Array | undefined;
+
+    // The first line cannot start with a leading space.
+    let buf = await this.r.peek(1);
+    if (buf === null) {
+      return null;
+    } else if (WHITESPACES.includes(buf[0])) {
+      line = (await this.readLineSlice()) as Uint8Array;
+    }
+
+    buf = await this.r.peek(1);
+    if (buf === null) {
+      throw new Deno.errors.UnexpectedEof();
+    } else if (WHITESPACES.includes(buf[0])) {
+      throw new Deno.errors.InvalidData(
+        `malformed MIME header initial line: ${str(line)}`,
+      );
+    }
+
+    while (true) {
+      const kv = await this.readLineSlice(); // readContinuedLineSlice
+      if (kv === null) throw new Deno.errors.UnexpectedEof();
+      if (kv.byteLength === 0) return m;
+
+      // Key ends at first colon
+      let i = kv.indexOf(CHAR_COLON);
+      if (i < 0) {
+        throw new Deno.errors.InvalidData(
+          `malformed MIME header line: ${str(kv)}`,
+        );
+      }
+
+      //let key = canonicalMIMEHeaderKey(kv.subarray(0, endKey));
+      const key = str(kv.subarray(0, i));
+
+      // As per RFC 7230 field-name is a token,
+      // tokens consist of one or more chars.
+      // We could throw `Deno.errors.InvalidData` here,
+      // but better to be liberal in what we
+      // accept, so if we get an empty key, skip it.
+      if (key == "") {
+        continue;
+      }
+
+      // Skip initial spaces in value.
+      i++; // skip colon
+      while (
+        i < kv.byteLength &&
+        (WHITESPACES.includes(kv[i]))
+      ) {
+        i++;
+      }
+      const value = str(kv.subarray(i)).replace(
+        invalidHeaderCharRegex,
+        encodeURI,
+      );
+
+      // In case of invalid header we swallow the error
+      // example: "Audio Mode" => invalid due to space in the key
+      try {
+        m.append(key, value);
+      } catch {
+        // Pass
+      }
+    }
+  }
+
+  async readLineSlice(): Promise<Uint8Array | null> {
+    let line = new Uint8Array(0);
+    let r: ReadLineResult | null = null;
+
+    do {
+      r = await this.r.readLine();
+      // TODO(ry):
+      // This skipSpace() is definitely misplaced, but I don't know where it
+      // comes from nor how to fix it.
+
+      //TODO(SmashingQuasar): Kept skipSpace to preserve behavior but it should be looked into to check if it makes sense when this is used.
+
+      if (r !== null && this.skipSpace(r.line) !== 0) {
+        line = concat([line, r.line]);
+      }
+    } while (r !== null && r.more);
+
+    return r === null ? null : line;
+  }
+
+  skipSpace(l: Uint8Array): number {
+    let n = 0;
+
+    for (const val of l) {
+      if (!WHITESPACES.includes(val)) {
+        n++;
+      }
+    }
+
+    return n;
+  }
+}
diff --git a/tests/testdata/run/tls.out b/tests/specs/run/tls_connecttls/tls.out
similarity index 100%
rename from tests/testdata/run/tls.out
rename to tests/specs/run/tls_connecttls/tls.out
diff --git a/tests/testdata/run/tls_connecttls.js b/tests/specs/run/tls_connecttls/tls_connecttls.js
similarity index 94%
rename from tests/testdata/run/tls_connecttls.js
rename to tests/specs/run/tls_connecttls/tls_connecttls.js
index 07b361f9ce..686b13aea3 100644
--- a/tests/testdata/run/tls_connecttls.js
+++ b/tests/specs/run/tls_connecttls/tls_connecttls.js
@@ -12,8 +12,8 @@ const port = 3505;
 const listener = Deno.listenTls({
   hostname,
   port,
-  cert: Deno.readTextFileSync("./tls/localhost.crt"),
-  key: Deno.readTextFileSync("./tls/localhost.key"),
+  cert: Deno.readTextFileSync("./localhost.crt"),
+  key: Deno.readTextFileSync("./localhost.key"),
 });
 
 const response = encoder.encode(
diff --git a/tests/specs/run/tls_starttls/RootCA.pem b/tests/specs/run/tls_starttls/RootCA.pem
new file mode 100644
index 0000000000..c2f84ceebc
--- /dev/null
+++ b/tests/specs/run/tls_starttls/RootCA.pem
@@ -0,0 +1,19 @@
+-----BEGIN CERTIFICATE-----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+-----END CERTIFICATE-----
diff --git a/tests/specs/run/tls_starttls/__test__.jsonc b/tests/specs/run/tls_starttls/__test__.jsonc
new file mode 100644
index 0000000000..4c1fe6324d
--- /dev/null
+++ b/tests/specs/run/tls_starttls/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-net --allow-read --cert RootCA.pem --config deno.json tls_starttls.js",
+  "output": "tls.out"
+}
diff --git a/tests/specs/run/tls_starttls/deno.json b/tests/specs/run/tls_starttls/deno.json
new file mode 100644
index 0000000000..105514e133
--- /dev/null
+++ b/tests/specs/run/tls_starttls/deno.json
@@ -0,0 +1,4 @@
+{
+  "lock": false,
+  "importMap": "../../../../import_map.json"
+}
diff --git a/tests/specs/run/tls_starttls/localhost.crt b/tests/specs/run/tls_starttls/localhost.crt
new file mode 100644
index 0000000000..a71ae9050f
--- /dev/null
+++ b/tests/specs/run/tls_starttls/localhost.crt
@@ -0,0 +1,21 @@
+-----BEGIN CERTIFICATE-----
+MIIDajCCAlKgAwIBAgIJAOPyQVdy/UpPMA0GCSqGSIb3DQEBCwUAMCcxCzAJBgNV
+BAYTAlVTMRgwFgYDVQQDDA9FeGFtcGxlLVJvb3QtQ0EwIBcNMTkxMDIxMTYyODU4
+WhgPMjExODA5MjcxNjI4NThaMG0xCzAJBgNVBAYTAlVTMRIwEAYDVQQIDAlZb3Vy
+U3RhdGUxETAPBgNVBAcMCFlvdXJDaXR5MR0wGwYDVQQKDBRFeGFtcGxlLUNlcnRp
+ZmljYXRlczEYMBYGA1UEAwwPbG9jYWxob3N0LmxvY2FsMIIBIjANBgkqhkiG9w0B
+AQEFAAOCAQ8AMIIBCgKCAQEAz9svjVdf5jihUBtofd84XKdb8dEHQRJfDNKaJ4Ar
+baqMHAdnqi/fWtlqEEMn8gweZ7+4hshECY5mnx4Hhy7IAbePDsTTbSm01dChhlxF
+uvd9QuvzvrqSjSq+v4Jlau+pQIhUzzV12dF5bFvrIrGWxCZp+W7lLDZI6Pd6Su+y
+ZIeiwrUaPMzdUePNf2hZI/IvWCUMCIyoqrrKHdHoPuvQCW17IyxsnFQJNbmN+Rtp
+BQilhtwvBbggCBWhHxEdiqBaZHDw6Zl+bU7ejx1mu9A95wpQ9SCL2cRkAlz2LDOy
+wznrTAwGcvqvFKxlV+3HsaD7rba4kCA1Ihp5mm/dS2k94QIDAQABo1EwTzAfBgNV
+HSMEGDAWgBTzut+pwwDfqmMYcI9KNWRDhxcIpTAJBgNVHRMEAjAAMAsGA1UdDwQE
+AwIE8DAUBgNVHREEDTALgglsb2NhbGhvc3QwDQYJKoZIhvcNAQELBQADggEBAKVu
+vVpu5nPGAGn1SX4FQUcbn9Z5wgBkjnZxfJHJQX4sYIRlcirZviPHCZGPWex4VHC+
+lFMm+70YEN2uoe5jGrdgcugzx2Amc7/mLrsvvpMsaS0PlxNMcqhdM1WHbGjjdNln
+XICVITSKnB1fSGH6uo9CMCWw5kgPS9o4QWrLLkxnds3hoz7gVEUyi/6V65mcfFNA
+lof9iKcK9JsSHdBs35vpv7UKLX+96RM7Nm2Mu0yue5JiS79/zuMA/Kryxot4jv5z
+ecdWFl0eIyQBZmBzMw2zPUqkxEnXLiKjV8jutEg/4qovTOB6YiA41qbARXdzNA2V
+FYuchcTcWmnmVVRFyyU=
+-----END CERTIFICATE-----
diff --git a/tests/specs/run/tls_starttls/localhost.key b/tests/specs/run/tls_starttls/localhost.key
new file mode 100644
index 0000000000..42774c9771
--- /dev/null
+++ b/tests/specs/run/tls_starttls/localhost.key
@@ -0,0 +1,28 @@
+-----BEGIN PRIVATE KEY-----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+-----END PRIVATE KEY-----
diff --git a/tests/specs/run/tls_starttls/textproto.ts b/tests/specs/run/tls_starttls/textproto.ts
new file mode 100644
index 0000000000..9e0f5f5f0a
--- /dev/null
+++ b/tests/specs/run/tls_starttls/textproto.ts
@@ -0,0 +1,170 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+// Copyright 2009 The Go Authors. All rights reserved.
+// Use of this source code is governed by a BSD-style
+// license that can be found in the LICENSE file.
+
+/** **Deprecated**. Use `TextLineStream` from `std/steams` for line-by-line text reading instead.
+ *
+ * A reader for dealing with low level text based protocols.
+ *
+ * Based on
+ * [net/textproto](https://github.com/golang/go/tree/master/src/net/textproto).
+ *
+ * @deprecated (will be removed after 0.159.0) Use `TextLineStream` from `std/steams` for line-by-line text reading instead.
+ * @module
+ */
+
+import type { BufReader, ReadLineResult } from "@std/io/buf-reader";
+import { concat } from "@std/bytes/concat";
+
+// Constants created for DRY
+const CHAR_SPACE: number = " ".charCodeAt(0);
+const CHAR_TAB: number = "\t".charCodeAt(0);
+const CHAR_COLON: number = ":".charCodeAt(0);
+
+const WHITESPACES: Array<number> = [CHAR_SPACE, CHAR_TAB];
+
+const decoder = new TextDecoder();
+
+// FROM https://github.com/denoland/deno/blob/b34628a26ab0187a827aa4ebe256e23178e25d39/cli/js/web/headers.ts#L9
+const invalidHeaderCharRegex = /[^\t\x20-\x7e\x80-\xff]/g;
+
+function str(buf: Uint8Array | null | undefined): string {
+  return !buf ? "" : decoder.decode(buf);
+}
+
+/**
+ * @deprecated (will be removed after 0.159.0) Use `TextLineStream` from `std/steams` for line-by-line text reading instead.
+ */
+export class TextProtoReader {
+  constructor(readonly r: BufReader) {}
+
+  /** readLine() reads a single line from the TextProtoReader,
+   * eliding the final \n or \r\n from the returned string.
+   */
+  async readLine(): Promise<string | null> {
+    const s = await this.readLineSlice();
+    return s === null ? null : str(s);
+  }
+
+  /** ReadMimeHeader reads a MIME-style header from r.
+   * The header is a sequence of possibly continued Key: Value lines
+   * ending in a blank line.
+   * The returned map m maps CanonicalMIMEHeaderKey(key) to a
+   * sequence of values in the same order encountered in the input.
+   *
+   * For example, consider this input:
+   *
+   * 	My-Key: Value 1
+   * 	Long-Key: Even
+   * 	       Longer Value
+   * 	My-Key: Value 2
+   *
+   * Given that input, ReadMIMEHeader returns the map:
+   *
+   * 	map[string][]string{
+   * 		"My-Key": {"Value 1", "Value 2"},
+   * 		"Long-Key": {"Even Longer Value"},
+   * 	}
+   */
+  async readMimeHeader(): Promise<Headers | null> {
+    const m = new Headers();
+    let line: Uint8Array | undefined;
+
+    // The first line cannot start with a leading space.
+    let buf = await this.r.peek(1);
+    if (buf === null) {
+      return null;
+    } else if (WHITESPACES.includes(buf[0])) {
+      line = (await this.readLineSlice()) as Uint8Array;
+    }
+
+    buf = await this.r.peek(1);
+    if (buf === null) {
+      throw new Deno.errors.UnexpectedEof();
+    } else if (WHITESPACES.includes(buf[0])) {
+      throw new Deno.errors.InvalidData(
+        `malformed MIME header initial line: ${str(line)}`,
+      );
+    }
+
+    while (true) {
+      const kv = await this.readLineSlice(); // readContinuedLineSlice
+      if (kv === null) throw new Deno.errors.UnexpectedEof();
+      if (kv.byteLength === 0) return m;
+
+      // Key ends at first colon
+      let i = kv.indexOf(CHAR_COLON);
+      if (i < 0) {
+        throw new Deno.errors.InvalidData(
+          `malformed MIME header line: ${str(kv)}`,
+        );
+      }
+
+      //let key = canonicalMIMEHeaderKey(kv.subarray(0, endKey));
+      const key = str(kv.subarray(0, i));
+
+      // As per RFC 7230 field-name is a token,
+      // tokens consist of one or more chars.
+      // We could throw `Deno.errors.InvalidData` here,
+      // but better to be liberal in what we
+      // accept, so if we get an empty key, skip it.
+      if (key == "") {
+        continue;
+      }
+
+      // Skip initial spaces in value.
+      i++; // skip colon
+      while (
+        i < kv.byteLength &&
+        (WHITESPACES.includes(kv[i]))
+      ) {
+        i++;
+      }
+      const value = str(kv.subarray(i)).replace(
+        invalidHeaderCharRegex,
+        encodeURI,
+      );
+
+      // In case of invalid header we swallow the error
+      // example: "Audio Mode" => invalid due to space in the key
+      try {
+        m.append(key, value);
+      } catch {
+        // Pass
+      }
+    }
+  }
+
+  async readLineSlice(): Promise<Uint8Array | null> {
+    let line = new Uint8Array(0);
+    let r: ReadLineResult | null = null;
+
+    do {
+      r = await this.r.readLine();
+      // TODO(ry):
+      // This skipSpace() is definitely misplaced, but I don't know where it
+      // comes from nor how to fix it.
+
+      //TODO(SmashingQuasar): Kept skipSpace to preserve behavior but it should be looked into to check if it makes sense when this is used.
+
+      if (r !== null && this.skipSpace(r.line) !== 0) {
+        line = concat([line, r.line]);
+      }
+    } while (r !== null && r.more);
+
+    return r === null ? null : line;
+  }
+
+  skipSpace(l: Uint8Array): number {
+    let n = 0;
+
+    for (const val of l) {
+      if (!WHITESPACES.includes(val)) {
+        n++;
+      }
+    }
+
+    return n;
+  }
+}
diff --git a/tests/specs/run/tls_starttls/tls.out b/tests/specs/run/tls_starttls/tls.out
new file mode 100644
index 0000000000..c8e8a135c9
--- /dev/null
+++ b/tests/specs/run/tls_starttls/tls.out
@@ -0,0 +1 @@
+DONE
diff --git a/tests/testdata/run/tls_starttls.js b/tests/specs/run/tls_starttls/tls_starttls.js
similarity index 94%
rename from tests/testdata/run/tls_starttls.js
rename to tests/specs/run/tls_starttls/tls_starttls.js
index 8e7ac03ee6..cd5718ff5a 100644
--- a/tests/testdata/run/tls_starttls.js
+++ b/tests/specs/run/tls_starttls/tls_starttls.js
@@ -13,8 +13,8 @@ const port = 3504;
 const listener = Deno.listenTls({
   hostname,
   port,
-  cert: Deno.readTextFileSync("./tls/localhost.crt"),
-  key: Deno.readTextFileSync("./tls/localhost.key"),
+  cert: Deno.readTextFileSync("./localhost.crt"),
+  key: Deno.readTextFileSync("./localhost.key"),
 });
 
 const response = encoder.encode(
diff --git a/tests/specs/run/top_level_await/__test__.jsonc b/tests/specs/run/top_level_await/__test__.jsonc
new file mode 100644
index 0000000000..25537db5f4
--- /dev/null
+++ b/tests/specs/run/top_level_await/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read top_level_await/top_level_await.js",
+  "output": "top_level_await/top_level_await.out"
+}
diff --git a/tests/specs/run/top_level_await/hello.txt b/tests/specs/run/top_level_await/hello.txt
new file mode 100644
index 0000000000..6769dd60bd
--- /dev/null
+++ b/tests/specs/run/top_level_await/hello.txt
@@ -0,0 +1 @@
+Hello world!
\ No newline at end of file
diff --git a/tests/testdata/run/top_level_await/circular.js b/tests/specs/run/top_level_await/top_level_await/circular.js
similarity index 100%
rename from tests/testdata/run/top_level_await/circular.js
rename to tests/specs/run/top_level_await/top_level_await/circular.js
diff --git a/tests/testdata/run/top_level_await/circular.out b/tests/specs/run/top_level_await/top_level_await/circular.out
similarity index 100%
rename from tests/testdata/run/top_level_await/circular.out
rename to tests/specs/run/top_level_await/top_level_await/circular.out
diff --git a/tests/specs/run/top_level_await/top_level_await/loop.js b/tests/specs/run/top_level_await/top_level_await/loop.js
new file mode 100644
index 0000000000..f229e03f61
--- /dev/null
+++ b/tests/specs/run/top_level_await/top_level_await/loop.js
@@ -0,0 +1,20 @@
+const importsDir = Deno.readDirSync(
+  Deno.realPathSync("./top_level_await/tla2"),
+);
+
+const resolvedPaths = [];
+
+for (const { name } of importsDir) {
+  const filePath = Deno.realPathSync(`./top_level_await/tla2/${name}`);
+  resolvedPaths.push(filePath);
+}
+
+resolvedPaths.sort();
+
+for (const filePath of resolvedPaths) {
+  console.log("loading", filePath);
+  const mod = await import(`file://${filePath}`);
+  console.log("loaded", mod);
+}
+
+console.log("all loaded");
diff --git a/tests/testdata/run/top_level_await/loop.out b/tests/specs/run/top_level_await/top_level_await/loop.out
similarity index 100%
rename from tests/testdata/run/top_level_await/loop.out
rename to tests/specs/run/top_level_await/top_level_await/loop.out
diff --git a/tests/testdata/run/top_level_await/nested.out b/tests/specs/run/top_level_await/top_level_await/nested.out
similarity index 100%
rename from tests/testdata/run/top_level_await/nested.out
rename to tests/specs/run/top_level_await/top_level_await/nested.out
diff --git a/tests/testdata/run/top_level_await/nested/a.js b/tests/specs/run/top_level_await/top_level_await/nested/a.js
similarity index 100%
rename from tests/testdata/run/top_level_await/nested/a.js
rename to tests/specs/run/top_level_await/top_level_await/nested/a.js
diff --git a/tests/testdata/run/top_level_await/nested/b.js b/tests/specs/run/top_level_await/top_level_await/nested/b.js
similarity index 100%
rename from tests/testdata/run/top_level_await/nested/b.js
rename to tests/specs/run/top_level_await/top_level_await/nested/b.js
diff --git a/tests/testdata/run/top_level_await/nested/main.js b/tests/specs/run/top_level_await/top_level_await/nested/main.js
similarity index 100%
rename from tests/testdata/run/top_level_await/nested/main.js
rename to tests/specs/run/top_level_await/top_level_await/nested/main.js
diff --git a/tests/testdata/run/top_level_await/order.js b/tests/specs/run/top_level_await/top_level_await/order.js
similarity index 100%
rename from tests/testdata/run/top_level_await/order.js
rename to tests/specs/run/top_level_await/top_level_await/order.js
diff --git a/tests/testdata/run/top_level_await/order.out b/tests/specs/run/top_level_await/top_level_await/order.out
similarity index 100%
rename from tests/testdata/run/top_level_await/order.out
rename to tests/specs/run/top_level_await/top_level_await/order.out
diff --git a/tests/specs/run/top_level_await/top_level_await/tla/a.js b/tests/specs/run/top_level_await/top_level_await/tla/a.js
new file mode 100644
index 0000000000..c3ef3f7dbc
--- /dev/null
+++ b/tests/specs/run/top_level_await/top_level_await/tla/a.js
@@ -0,0 +1,3 @@
+import order from "./order.js";
+
+order.push("b");
diff --git a/tests/specs/run/top_level_await/top_level_await/tla/b.js b/tests/specs/run/top_level_await/top_level_await/tla/b.js
new file mode 100644
index 0000000000..3271c92d8f
--- /dev/null
+++ b/tests/specs/run/top_level_await/top_level_await/tla/b.js
@@ -0,0 +1,7 @@
+import order from "./order.js";
+
+await new Promise((resolve) => {
+  setTimeout(resolve, 200);
+});
+
+order.push("a");
diff --git a/tests/specs/run/top_level_await/top_level_await/tla/c.js b/tests/specs/run/top_level_await/top_level_await/tla/c.js
new file mode 100644
index 0000000000..806eb0a8be
--- /dev/null
+++ b/tests/specs/run/top_level_await/top_level_await/tla/c.js
@@ -0,0 +1,3 @@
+import order from "./order.js";
+
+order.push("c");
diff --git a/tests/specs/run/top_level_await/top_level_await/tla/d.js b/tests/specs/run/top_level_await/top_level_await/tla/d.js
new file mode 100644
index 0000000000..283ebf817f
--- /dev/null
+++ b/tests/specs/run/top_level_await/top_level_await/tla/d.js
@@ -0,0 +1,8 @@
+import order from "./order.js";
+
+const end = Date.now() + 500;
+while (end < Date.now()) {
+  // pass
+}
+
+order.push("d");
diff --git a/tests/specs/run/top_level_await/top_level_await/tla/order.js b/tests/specs/run/top_level_await/top_level_await/tla/order.js
new file mode 100644
index 0000000000..f213a562ce
--- /dev/null
+++ b/tests/specs/run/top_level_await/top_level_await/tla/order.js
@@ -0,0 +1 @@
+export default ["order"];
diff --git a/tests/specs/run/top_level_await/top_level_await/tla/parent.js b/tests/specs/run/top_level_await/top_level_await/tla/parent.js
new file mode 100644
index 0000000000..1ecc154634
--- /dev/null
+++ b/tests/specs/run/top_level_await/top_level_await/tla/parent.js
@@ -0,0 +1,9 @@
+import order from "./order.js";
+import "./a.js";
+import "./b.js";
+import "./c.js";
+import "./d.js";
+
+order.push("parent");
+
+export default order;
diff --git a/tests/specs/run/top_level_await/top_level_await/tla2/a.js b/tests/specs/run/top_level_await/top_level_await/tla2/a.js
new file mode 100644
index 0000000000..d07bcb94db
--- /dev/null
+++ b/tests/specs/run/top_level_await/top_level_await/tla2/a.js
@@ -0,0 +1,5 @@
+export default class Foo {
+  constructor(message) {
+    this.message = message;
+  }
+}
diff --git a/tests/specs/run/top_level_await/top_level_await/tla2/b.js b/tests/specs/run/top_level_await/top_level_await/tla2/b.js
new file mode 100644
index 0000000000..68e357c1e9
--- /dev/null
+++ b/tests/specs/run/top_level_await/top_level_await/tla2/b.js
@@ -0,0 +1,5 @@
+export default class Bar {
+  constructor(message) {
+    this.message = message;
+  }
+}
diff --git a/tests/specs/run/top_level_await/top_level_await/tla3/b.js b/tests/specs/run/top_level_await/top_level_await/tla3/b.js
new file mode 100644
index 0000000000..d0349545e9
--- /dev/null
+++ b/tests/specs/run/top_level_await/top_level_await/tla3/b.js
@@ -0,0 +1,7 @@
+import { foo } from "./timeout_loop.js";
+import { collection } from "../circular.js";
+
+console.log("collection in b", collection);
+console.log("foo in b", foo);
+
+export const a = "a";
diff --git a/tests/specs/run/top_level_await/top_level_await/tla3/timeout_loop.js b/tests/specs/run/top_level_await/top_level_await/tla3/timeout_loop.js
new file mode 100644
index 0000000000..860e6cd2ae
--- /dev/null
+++ b/tests/specs/run/top_level_await/top_level_await/tla3/timeout_loop.js
@@ -0,0 +1,23 @@
+export const foo = "foo";
+
+export function delay(ms) {
+  return new Promise((res) =>
+    setTimeout(() => {
+      res();
+    }, ms)
+  );
+}
+
+let i = 0;
+
+async function timeoutLoop() {
+  await delay(1000);
+  console.log("timeout loop", i);
+  i++;
+  if (i > 5) {
+    return;
+  }
+  timeoutLoop();
+}
+
+timeoutLoop();
diff --git a/tests/specs/run/top_level_await/top_level_await/top_level_await.js b/tests/specs/run/top_level_await/top_level_await/top_level_await.js
new file mode 100644
index 0000000000..31c83caedc
--- /dev/null
+++ b/tests/specs/run/top_level_await/top_level_await/top_level_await.js
@@ -0,0 +1,3 @@
+const buf = await Deno.readFile("./hello.txt");
+const n = await Deno.stdout.write(buf);
+console.log(`\n\nwrite ${n}`);
diff --git a/tests/testdata/run/top_level_await/top_level_await.out b/tests/specs/run/top_level_await/top_level_await/top_level_await.out
similarity index 100%
rename from tests/testdata/run/top_level_await/top_level_await.out
rename to tests/specs/run/top_level_await/top_level_await/top_level_await.out
diff --git a/tests/testdata/run/top_level_await/top_level_await.ts b/tests/specs/run/top_level_await/top_level_await/top_level_await.ts
similarity index 100%
rename from tests/testdata/run/top_level_await/top_level_await.ts
rename to tests/specs/run/top_level_await/top_level_await/top_level_await.ts
diff --git a/tests/testdata/run/top_level_await/top_level_for_await.js b/tests/specs/run/top_level_await/top_level_await/top_level_for_await.js
similarity index 100%
rename from tests/testdata/run/top_level_await/top_level_for_await.js
rename to tests/specs/run/top_level_await/top_level_await/top_level_for_await.js
diff --git a/tests/testdata/run/top_level_await/top_level_for_await.out b/tests/specs/run/top_level_await/top_level_await/top_level_for_await.out
similarity index 100%
rename from tests/testdata/run/top_level_await/top_level_for_await.out
rename to tests/specs/run/top_level_await/top_level_await/top_level_for_await.out
diff --git a/tests/testdata/run/top_level_await/top_level_for_await.ts b/tests/specs/run/top_level_await/top_level_await/top_level_for_await.ts
similarity index 100%
rename from tests/testdata/run/top_level_await/top_level_for_await.ts
rename to tests/specs/run/top_level_await/top_level_await/top_level_for_await.ts
diff --git a/tests/testdata/run/top_level_await/unresolved.js b/tests/specs/run/top_level_await/top_level_await/unresolved.js
similarity index 100%
rename from tests/testdata/run/top_level_await/unresolved.js
rename to tests/specs/run/top_level_await/top_level_await/unresolved.js
diff --git a/tests/testdata/run/top_level_await/unresolved.out b/tests/specs/run/top_level_await/top_level_await/unresolved.out
similarity index 100%
rename from tests/testdata/run/top_level_await/unresolved.out
rename to tests/specs/run/top_level_await/top_level_await/unresolved.out
diff --git a/tests/specs/run/top_level_await_circular/__test__.jsonc b/tests/specs/run/top_level_await_circular/__test__.jsonc
new file mode 100644
index 0000000000..3e236b2107
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --allow-read top_level_await/circular.js",
+  "output": "top_level_await/circular.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/circular.js b/tests/specs/run/top_level_await_circular/top_level_await/circular.js
new file mode 100644
index 0000000000..ff2964b6a5
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/circular.js
@@ -0,0 +1,8 @@
+import { foo } from "./tla3/timeout_loop.js";
+
+export const collection = [];
+
+const mod = await import("./tla3/b.js");
+
+console.log("foo in main", foo);
+console.log("mod", mod);
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/circular.out b/tests/specs/run/top_level_await_circular/top_level_await/circular.out
new file mode 100644
index 0000000000..c889789613
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/circular.out
@@ -0,0 +1,10 @@
+timeout loop 0
+timeout loop 1
+timeout loop 2
+timeout loop 3
+timeout loop 4
+timeout loop 5
+error: Top-level await promise never resolved
+const mod = await import("./tla3/b.js");
+            ^
+    at <anonymous> ([WILDCARD]/top_level_await/circular.js:5:13)
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/loop.js b/tests/specs/run/top_level_await_circular/top_level_await/loop.js
new file mode 100644
index 0000000000..f229e03f61
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/loop.js
@@ -0,0 +1,20 @@
+const importsDir = Deno.readDirSync(
+  Deno.realPathSync("./top_level_await/tla2"),
+);
+
+const resolvedPaths = [];
+
+for (const { name } of importsDir) {
+  const filePath = Deno.realPathSync(`./top_level_await/tla2/${name}`);
+  resolvedPaths.push(filePath);
+}
+
+resolvedPaths.sort();
+
+for (const filePath of resolvedPaths) {
+  console.log("loading", filePath);
+  const mod = await import(`file://${filePath}`);
+  console.log("loaded", mod);
+}
+
+console.log("all loaded");
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/loop.out b/tests/specs/run/top_level_await_circular/top_level_await/loop.out
new file mode 100644
index 0000000000..1bdffbf660
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/loop.out
@@ -0,0 +1,5 @@
+loading [WILDCARD]a.js
+loaded [Module: null prototype] { default: [class Foo] }
+loading [WILDCARD]b.js
+loaded [Module: null prototype] { default: [class Bar] }
+all loaded
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/nested.out b/tests/specs/run/top_level_await_circular/top_level_await/nested.out
new file mode 100644
index 0000000000..8a1218a102
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/nested.out
@@ -0,0 +1,5 @@
+1
+2
+3
+4
+5
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/nested/a.js b/tests/specs/run/top_level_await_circular/top_level_await/nested/a.js
new file mode 100644
index 0000000000..74837d4ba1
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/nested/a.js
@@ -0,0 +1,3 @@
+console.log(2);
+await import("./b.js");
+console.log(4);
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/nested/b.js b/tests/specs/run/top_level_await_circular/top_level_await/nested/b.js
new file mode 100644
index 0000000000..3bd241b50e
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/nested/b.js
@@ -0,0 +1 @@
+console.log(3);
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/nested/main.js b/tests/specs/run/top_level_await_circular/top_level_await/nested/main.js
new file mode 100644
index 0000000000..ed46a47175
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/nested/main.js
@@ -0,0 +1,3 @@
+console.log(1);
+await import("./a.js");
+console.log(5);
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/order.js b/tests/specs/run/top_level_await_circular/top_level_await/order.js
new file mode 100644
index 0000000000..30659cdfbf
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/order.js
@@ -0,0 +1,21 @@
+// Ported from Node
+// https://github.com/nodejs/node/blob/54746bb763ebea0dc7e99d88ff4b379bcd680964/test/es-module/test-esm-tla.mjs
+
+const { default: order } = await import("./tla/parent.js");
+
+console.log("order", JSON.stringify(order));
+
+if (
+  !(
+    order[0] === "order" &&
+    order[1] === "b" &&
+    order[2] === "c" &&
+    order[3] === "d" &&
+    order[4] === "a" &&
+    order[5] === "parent"
+  )
+) {
+  throw new Error("TLA wrong order");
+}
+
+console.log("TLA order correct");
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/order.out b/tests/specs/run/top_level_await_circular/top_level_await/order.out
new file mode 100644
index 0000000000..4cc27858cf
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/order.out
@@ -0,0 +1,2 @@
+order ["order","b","c","d","a","parent"]
+TLA order correct
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/tla/a.js b/tests/specs/run/top_level_await_circular/top_level_await/tla/a.js
new file mode 100644
index 0000000000..c3ef3f7dbc
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/tla/a.js
@@ -0,0 +1,3 @@
+import order from "./order.js";
+
+order.push("b");
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/tla/b.js b/tests/specs/run/top_level_await_circular/top_level_await/tla/b.js
new file mode 100644
index 0000000000..3271c92d8f
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/tla/b.js
@@ -0,0 +1,7 @@
+import order from "./order.js";
+
+await new Promise((resolve) => {
+  setTimeout(resolve, 200);
+});
+
+order.push("a");
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/tla/c.js b/tests/specs/run/top_level_await_circular/top_level_await/tla/c.js
new file mode 100644
index 0000000000..806eb0a8be
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/tla/c.js
@@ -0,0 +1,3 @@
+import order from "./order.js";
+
+order.push("c");
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/tla/d.js b/tests/specs/run/top_level_await_circular/top_level_await/tla/d.js
new file mode 100644
index 0000000000..283ebf817f
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/tla/d.js
@@ -0,0 +1,8 @@
+import order from "./order.js";
+
+const end = Date.now() + 500;
+while (end < Date.now()) {
+  // pass
+}
+
+order.push("d");
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/tla/order.js b/tests/specs/run/top_level_await_circular/top_level_await/tla/order.js
new file mode 100644
index 0000000000..f213a562ce
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/tla/order.js
@@ -0,0 +1 @@
+export default ["order"];
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/tla/parent.js b/tests/specs/run/top_level_await_circular/top_level_await/tla/parent.js
new file mode 100644
index 0000000000..1ecc154634
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/tla/parent.js
@@ -0,0 +1,9 @@
+import order from "./order.js";
+import "./a.js";
+import "./b.js";
+import "./c.js";
+import "./d.js";
+
+order.push("parent");
+
+export default order;
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/tla2/a.js b/tests/specs/run/top_level_await_circular/top_level_await/tla2/a.js
new file mode 100644
index 0000000000..d07bcb94db
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/tla2/a.js
@@ -0,0 +1,5 @@
+export default class Foo {
+  constructor(message) {
+    this.message = message;
+  }
+}
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/tla2/b.js b/tests/specs/run/top_level_await_circular/top_level_await/tla2/b.js
new file mode 100644
index 0000000000..68e357c1e9
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/tla2/b.js
@@ -0,0 +1,5 @@
+export default class Bar {
+  constructor(message) {
+    this.message = message;
+  }
+}
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/tla3/b.js b/tests/specs/run/top_level_await_circular/top_level_await/tla3/b.js
new file mode 100644
index 0000000000..d0349545e9
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/tla3/b.js
@@ -0,0 +1,7 @@
+import { foo } from "./timeout_loop.js";
+import { collection } from "../circular.js";
+
+console.log("collection in b", collection);
+console.log("foo in b", foo);
+
+export const a = "a";
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/tla3/timeout_loop.js b/tests/specs/run/top_level_await_circular/top_level_await/tla3/timeout_loop.js
new file mode 100644
index 0000000000..860e6cd2ae
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/tla3/timeout_loop.js
@@ -0,0 +1,23 @@
+export const foo = "foo";
+
+export function delay(ms) {
+  return new Promise((res) =>
+    setTimeout(() => {
+      res();
+    }, ms)
+  );
+}
+
+let i = 0;
+
+async function timeoutLoop() {
+  await delay(1000);
+  console.log("timeout loop", i);
+  i++;
+  if (i > 5) {
+    return;
+  }
+  timeoutLoop();
+}
+
+timeoutLoop();
diff --git a/tests/testdata/run/top_level_await/top_level_await.js b/tests/specs/run/top_level_await_circular/top_level_await/top_level_await.js
similarity index 100%
rename from tests/testdata/run/top_level_await/top_level_await.js
rename to tests/specs/run/top_level_await_circular/top_level_await/top_level_await.js
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/top_level_await.out b/tests/specs/run/top_level_await_circular/top_level_await/top_level_await.out
new file mode 100644
index 0000000000..4b65d15fe3
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/top_level_await.out
@@ -0,0 +1,3 @@
+Hello world!
+
+write 12
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/top_level_await.ts b/tests/specs/run/top_level_await_circular/top_level_await/top_level_await.ts
new file mode 100644
index 0000000000..8d47ceb21e
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/top_level_await.ts
@@ -0,0 +1,3 @@
+const buf: Uint8Array = await Deno.readFile("./assets/hello.txt");
+const n: number = await Deno.stdout.write(buf);
+console.log(`\n\nwrite ${n}`);
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/top_level_for_await.js b/tests/specs/run/top_level_await_circular/top_level_await/top_level_for_await.js
new file mode 100644
index 0000000000..a330f6c711
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/top_level_for_await.js
@@ -0,0 +1,10 @@
+function* asyncGenerator() {
+  let i = 0;
+  while (i < 3) {
+    yield i++;
+  }
+}
+
+for await (const num of asyncGenerator()) {
+  console.log(num);
+}
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/top_level_for_await.out b/tests/specs/run/top_level_await_circular/top_level_await/top_level_for_await.out
new file mode 100644
index 0000000000..4539bbf2d2
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/top_level_for_await.out
@@ -0,0 +1,3 @@
+0
+1
+2
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/top_level_for_await.ts b/tests/specs/run/top_level_await_circular/top_level_await/top_level_for_await.ts
new file mode 100644
index 0000000000..9179322d78
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/top_level_for_await.ts
@@ -0,0 +1,10 @@
+async function* asyncGenerator(): AsyncIterableIterator<number> {
+  let i = 0;
+  while (i < 3) {
+    yield i++;
+  }
+}
+
+for await (const num of asyncGenerator()) {
+  console.log(num);
+}
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/unresolved.js b/tests/specs/run/top_level_await_circular/top_level_await/unresolved.js
new file mode 100644
index 0000000000..231a8cd634
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/unresolved.js
@@ -0,0 +1 @@
+await new Promise(() => {});
diff --git a/tests/specs/run/top_level_await_circular/top_level_await/unresolved.out b/tests/specs/run/top_level_await_circular/top_level_await/unresolved.out
new file mode 100644
index 0000000000..1f4ea5d382
--- /dev/null
+++ b/tests/specs/run/top_level_await_circular/top_level_await/unresolved.out
@@ -0,0 +1,4 @@
+error: Top-level await promise never resolved
+await new Promise(() => {});
+^
+    at <anonymous> ([WILDCARD]top_level_await/unresolved.js:1:1)
diff --git a/tests/specs/run/top_level_await_loop/__test__.jsonc b/tests/specs/run/top_level_await_loop/__test__.jsonc
new file mode 100644
index 0000000000..b2f5c84c03
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read top_level_await/loop.js",
+  "output": "top_level_await/loop.out"
+}
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/circular.js b/tests/specs/run/top_level_await_loop/top_level_await/circular.js
new file mode 100644
index 0000000000..ff2964b6a5
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/circular.js
@@ -0,0 +1,8 @@
+import { foo } from "./tla3/timeout_loop.js";
+
+export const collection = [];
+
+const mod = await import("./tla3/b.js");
+
+console.log("foo in main", foo);
+console.log("mod", mod);
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/circular.out b/tests/specs/run/top_level_await_loop/top_level_await/circular.out
new file mode 100644
index 0000000000..c889789613
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/circular.out
@@ -0,0 +1,10 @@
+timeout loop 0
+timeout loop 1
+timeout loop 2
+timeout loop 3
+timeout loop 4
+timeout loop 5
+error: Top-level await promise never resolved
+const mod = await import("./tla3/b.js");
+            ^
+    at <anonymous> ([WILDCARD]/top_level_await/circular.js:5:13)
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/loop.js b/tests/specs/run/top_level_await_loop/top_level_await/loop.js
new file mode 100644
index 0000000000..f229e03f61
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/loop.js
@@ -0,0 +1,20 @@
+const importsDir = Deno.readDirSync(
+  Deno.realPathSync("./top_level_await/tla2"),
+);
+
+const resolvedPaths = [];
+
+for (const { name } of importsDir) {
+  const filePath = Deno.realPathSync(`./top_level_await/tla2/${name}`);
+  resolvedPaths.push(filePath);
+}
+
+resolvedPaths.sort();
+
+for (const filePath of resolvedPaths) {
+  console.log("loading", filePath);
+  const mod = await import(`file://${filePath}`);
+  console.log("loaded", mod);
+}
+
+console.log("all loaded");
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/loop.out b/tests/specs/run/top_level_await_loop/top_level_await/loop.out
new file mode 100644
index 0000000000..1bdffbf660
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/loop.out
@@ -0,0 +1,5 @@
+loading [WILDCARD]a.js
+loaded [Module: null prototype] { default: [class Foo] }
+loading [WILDCARD]b.js
+loaded [Module: null prototype] { default: [class Bar] }
+all loaded
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/nested.out b/tests/specs/run/top_level_await_loop/top_level_await/nested.out
new file mode 100644
index 0000000000..8a1218a102
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/nested.out
@@ -0,0 +1,5 @@
+1
+2
+3
+4
+5
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/nested/a.js b/tests/specs/run/top_level_await_loop/top_level_await/nested/a.js
new file mode 100644
index 0000000000..74837d4ba1
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/nested/a.js
@@ -0,0 +1,3 @@
+console.log(2);
+await import("./b.js");
+console.log(4);
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/nested/b.js b/tests/specs/run/top_level_await_loop/top_level_await/nested/b.js
new file mode 100644
index 0000000000..3bd241b50e
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/nested/b.js
@@ -0,0 +1 @@
+console.log(3);
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/nested/main.js b/tests/specs/run/top_level_await_loop/top_level_await/nested/main.js
new file mode 100644
index 0000000000..ed46a47175
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/nested/main.js
@@ -0,0 +1,3 @@
+console.log(1);
+await import("./a.js");
+console.log(5);
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/order.js b/tests/specs/run/top_level_await_loop/top_level_await/order.js
new file mode 100644
index 0000000000..30659cdfbf
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/order.js
@@ -0,0 +1,21 @@
+// Ported from Node
+// https://github.com/nodejs/node/blob/54746bb763ebea0dc7e99d88ff4b379bcd680964/test/es-module/test-esm-tla.mjs
+
+const { default: order } = await import("./tla/parent.js");
+
+console.log("order", JSON.stringify(order));
+
+if (
+  !(
+    order[0] === "order" &&
+    order[1] === "b" &&
+    order[2] === "c" &&
+    order[3] === "d" &&
+    order[4] === "a" &&
+    order[5] === "parent"
+  )
+) {
+  throw new Error("TLA wrong order");
+}
+
+console.log("TLA order correct");
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/order.out b/tests/specs/run/top_level_await_loop/top_level_await/order.out
new file mode 100644
index 0000000000..4cc27858cf
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/order.out
@@ -0,0 +1,2 @@
+order ["order","b","c","d","a","parent"]
+TLA order correct
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/tla/a.js b/tests/specs/run/top_level_await_loop/top_level_await/tla/a.js
new file mode 100644
index 0000000000..c3ef3f7dbc
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/tla/a.js
@@ -0,0 +1,3 @@
+import order from "./order.js";
+
+order.push("b");
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/tla/b.js b/tests/specs/run/top_level_await_loop/top_level_await/tla/b.js
new file mode 100644
index 0000000000..3271c92d8f
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/tla/b.js
@@ -0,0 +1,7 @@
+import order from "./order.js";
+
+await new Promise((resolve) => {
+  setTimeout(resolve, 200);
+});
+
+order.push("a");
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/tla/c.js b/tests/specs/run/top_level_await_loop/top_level_await/tla/c.js
new file mode 100644
index 0000000000..806eb0a8be
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/tla/c.js
@@ -0,0 +1,3 @@
+import order from "./order.js";
+
+order.push("c");
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/tla/d.js b/tests/specs/run/top_level_await_loop/top_level_await/tla/d.js
new file mode 100644
index 0000000000..283ebf817f
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/tla/d.js
@@ -0,0 +1,8 @@
+import order from "./order.js";
+
+const end = Date.now() + 500;
+while (end < Date.now()) {
+  // pass
+}
+
+order.push("d");
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/tla/order.js b/tests/specs/run/top_level_await_loop/top_level_await/tla/order.js
new file mode 100644
index 0000000000..f213a562ce
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/tla/order.js
@@ -0,0 +1 @@
+export default ["order"];
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/tla/parent.js b/tests/specs/run/top_level_await_loop/top_level_await/tla/parent.js
new file mode 100644
index 0000000000..1ecc154634
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/tla/parent.js
@@ -0,0 +1,9 @@
+import order from "./order.js";
+import "./a.js";
+import "./b.js";
+import "./c.js";
+import "./d.js";
+
+order.push("parent");
+
+export default order;
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/tla2/a.js b/tests/specs/run/top_level_await_loop/top_level_await/tla2/a.js
new file mode 100644
index 0000000000..d07bcb94db
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/tla2/a.js
@@ -0,0 +1,5 @@
+export default class Foo {
+  constructor(message) {
+    this.message = message;
+  }
+}
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/tla2/b.js b/tests/specs/run/top_level_await_loop/top_level_await/tla2/b.js
new file mode 100644
index 0000000000..68e357c1e9
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/tla2/b.js
@@ -0,0 +1,5 @@
+export default class Bar {
+  constructor(message) {
+    this.message = message;
+  }
+}
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/tla3/b.js b/tests/specs/run/top_level_await_loop/top_level_await/tla3/b.js
new file mode 100644
index 0000000000..d0349545e9
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/tla3/b.js
@@ -0,0 +1,7 @@
+import { foo } from "./timeout_loop.js";
+import { collection } from "../circular.js";
+
+console.log("collection in b", collection);
+console.log("foo in b", foo);
+
+export const a = "a";
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/tla3/timeout_loop.js b/tests/specs/run/top_level_await_loop/top_level_await/tla3/timeout_loop.js
new file mode 100644
index 0000000000..860e6cd2ae
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/tla3/timeout_loop.js
@@ -0,0 +1,23 @@
+export const foo = "foo";
+
+export function delay(ms) {
+  return new Promise((res) =>
+    setTimeout(() => {
+      res();
+    }, ms)
+  );
+}
+
+let i = 0;
+
+async function timeoutLoop() {
+  await delay(1000);
+  console.log("timeout loop", i);
+  i++;
+  if (i > 5) {
+    return;
+  }
+  timeoutLoop();
+}
+
+timeoutLoop();
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/top_level_await.js b/tests/specs/run/top_level_await_loop/top_level_await/top_level_await.js
new file mode 100644
index 0000000000..ea319ea124
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/top_level_await.js
@@ -0,0 +1,3 @@
+const buf = await Deno.readFile("./assets/hello.txt");
+const n = await Deno.stdout.write(buf);
+console.log(`\n\nwrite ${n}`);
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/top_level_await.out b/tests/specs/run/top_level_await_loop/top_level_await/top_level_await.out
new file mode 100644
index 0000000000..4b65d15fe3
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/top_level_await.out
@@ -0,0 +1,3 @@
+Hello world!
+
+write 12
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/top_level_await.ts b/tests/specs/run/top_level_await_loop/top_level_await/top_level_await.ts
new file mode 100644
index 0000000000..8d47ceb21e
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/top_level_await.ts
@@ -0,0 +1,3 @@
+const buf: Uint8Array = await Deno.readFile("./assets/hello.txt");
+const n: number = await Deno.stdout.write(buf);
+console.log(`\n\nwrite ${n}`);
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/top_level_for_await.js b/tests/specs/run/top_level_await_loop/top_level_await/top_level_for_await.js
new file mode 100644
index 0000000000..a330f6c711
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/top_level_for_await.js
@@ -0,0 +1,10 @@
+function* asyncGenerator() {
+  let i = 0;
+  while (i < 3) {
+    yield i++;
+  }
+}
+
+for await (const num of asyncGenerator()) {
+  console.log(num);
+}
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/top_level_for_await.out b/tests/specs/run/top_level_await_loop/top_level_await/top_level_for_await.out
new file mode 100644
index 0000000000..4539bbf2d2
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/top_level_for_await.out
@@ -0,0 +1,3 @@
+0
+1
+2
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/top_level_for_await.ts b/tests/specs/run/top_level_await_loop/top_level_await/top_level_for_await.ts
new file mode 100644
index 0000000000..9179322d78
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/top_level_for_await.ts
@@ -0,0 +1,10 @@
+async function* asyncGenerator(): AsyncIterableIterator<number> {
+  let i = 0;
+  while (i < 3) {
+    yield i++;
+  }
+}
+
+for await (const num of asyncGenerator()) {
+  console.log(num);
+}
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/unresolved.js b/tests/specs/run/top_level_await_loop/top_level_await/unresolved.js
new file mode 100644
index 0000000000..231a8cd634
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/unresolved.js
@@ -0,0 +1 @@
+await new Promise(() => {});
diff --git a/tests/specs/run/top_level_await_loop/top_level_await/unresolved.out b/tests/specs/run/top_level_await_loop/top_level_await/unresolved.out
new file mode 100644
index 0000000000..1f4ea5d382
--- /dev/null
+++ b/tests/specs/run/top_level_await_loop/top_level_await/unresolved.out
@@ -0,0 +1,4 @@
+error: Top-level await promise never resolved
+await new Promise(() => {});
+^
+    at <anonymous> ([WILDCARD]top_level_await/unresolved.js:1:1)
diff --git a/tests/specs/run/top_level_await_nested/__test__.jsonc b/tests/specs/run/top_level_await_nested/__test__.jsonc
new file mode 100644
index 0000000000..376180ecdc
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read top_level_await/nested/main.js",
+  "output": "top_level_await/nested.out"
+}
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/circular.js b/tests/specs/run/top_level_await_nested/top_level_await/circular.js
new file mode 100644
index 0000000000..ff2964b6a5
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/circular.js
@@ -0,0 +1,8 @@
+import { foo } from "./tla3/timeout_loop.js";
+
+export const collection = [];
+
+const mod = await import("./tla3/b.js");
+
+console.log("foo in main", foo);
+console.log("mod", mod);
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/circular.out b/tests/specs/run/top_level_await_nested/top_level_await/circular.out
new file mode 100644
index 0000000000..c889789613
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/circular.out
@@ -0,0 +1,10 @@
+timeout loop 0
+timeout loop 1
+timeout loop 2
+timeout loop 3
+timeout loop 4
+timeout loop 5
+error: Top-level await promise never resolved
+const mod = await import("./tla3/b.js");
+            ^
+    at <anonymous> ([WILDCARD]/top_level_await/circular.js:5:13)
diff --git a/tests/testdata/run/top_level_await/loop.js b/tests/specs/run/top_level_await_nested/top_level_await/loop.js
similarity index 100%
rename from tests/testdata/run/top_level_await/loop.js
rename to tests/specs/run/top_level_await_nested/top_level_await/loop.js
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/loop.out b/tests/specs/run/top_level_await_nested/top_level_await/loop.out
new file mode 100644
index 0000000000..1bdffbf660
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/loop.out
@@ -0,0 +1,5 @@
+loading [WILDCARD]a.js
+loaded [Module: null prototype] { default: [class Foo] }
+loading [WILDCARD]b.js
+loaded [Module: null prototype] { default: [class Bar] }
+all loaded
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/nested.out b/tests/specs/run/top_level_await_nested/top_level_await/nested.out
new file mode 100644
index 0000000000..8a1218a102
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/nested.out
@@ -0,0 +1,5 @@
+1
+2
+3
+4
+5
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/nested/a.js b/tests/specs/run/top_level_await_nested/top_level_await/nested/a.js
new file mode 100644
index 0000000000..74837d4ba1
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/nested/a.js
@@ -0,0 +1,3 @@
+console.log(2);
+await import("./b.js");
+console.log(4);
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/nested/b.js b/tests/specs/run/top_level_await_nested/top_level_await/nested/b.js
new file mode 100644
index 0000000000..3bd241b50e
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/nested/b.js
@@ -0,0 +1 @@
+console.log(3);
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/nested/main.js b/tests/specs/run/top_level_await_nested/top_level_await/nested/main.js
new file mode 100644
index 0000000000..ed46a47175
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/nested/main.js
@@ -0,0 +1,3 @@
+console.log(1);
+await import("./a.js");
+console.log(5);
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/order.js b/tests/specs/run/top_level_await_nested/top_level_await/order.js
new file mode 100644
index 0000000000..30659cdfbf
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/order.js
@@ -0,0 +1,21 @@
+// Ported from Node
+// https://github.com/nodejs/node/blob/54746bb763ebea0dc7e99d88ff4b379bcd680964/test/es-module/test-esm-tla.mjs
+
+const { default: order } = await import("./tla/parent.js");
+
+console.log("order", JSON.stringify(order));
+
+if (
+  !(
+    order[0] === "order" &&
+    order[1] === "b" &&
+    order[2] === "c" &&
+    order[3] === "d" &&
+    order[4] === "a" &&
+    order[5] === "parent"
+  )
+) {
+  throw new Error("TLA wrong order");
+}
+
+console.log("TLA order correct");
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/order.out b/tests/specs/run/top_level_await_nested/top_level_await/order.out
new file mode 100644
index 0000000000..4cc27858cf
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/order.out
@@ -0,0 +1,2 @@
+order ["order","b","c","d","a","parent"]
+TLA order correct
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/tla/a.js b/tests/specs/run/top_level_await_nested/top_level_await/tla/a.js
new file mode 100644
index 0000000000..c3ef3f7dbc
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/tla/a.js
@@ -0,0 +1,3 @@
+import order from "./order.js";
+
+order.push("b");
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/tla/b.js b/tests/specs/run/top_level_await_nested/top_level_await/tla/b.js
new file mode 100644
index 0000000000..3271c92d8f
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/tla/b.js
@@ -0,0 +1,7 @@
+import order from "./order.js";
+
+await new Promise((resolve) => {
+  setTimeout(resolve, 200);
+});
+
+order.push("a");
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/tla/c.js b/tests/specs/run/top_level_await_nested/top_level_await/tla/c.js
new file mode 100644
index 0000000000..806eb0a8be
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/tla/c.js
@@ -0,0 +1,3 @@
+import order from "./order.js";
+
+order.push("c");
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/tla/d.js b/tests/specs/run/top_level_await_nested/top_level_await/tla/d.js
new file mode 100644
index 0000000000..283ebf817f
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/tla/d.js
@@ -0,0 +1,8 @@
+import order from "./order.js";
+
+const end = Date.now() + 500;
+while (end < Date.now()) {
+  // pass
+}
+
+order.push("d");
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/tla/order.js b/tests/specs/run/top_level_await_nested/top_level_await/tla/order.js
new file mode 100644
index 0000000000..f213a562ce
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/tla/order.js
@@ -0,0 +1 @@
+export default ["order"];
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/tla/parent.js b/tests/specs/run/top_level_await_nested/top_level_await/tla/parent.js
new file mode 100644
index 0000000000..1ecc154634
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/tla/parent.js
@@ -0,0 +1,9 @@
+import order from "./order.js";
+import "./a.js";
+import "./b.js";
+import "./c.js";
+import "./d.js";
+
+order.push("parent");
+
+export default order;
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/tla2/a.js b/tests/specs/run/top_level_await_nested/top_level_await/tla2/a.js
new file mode 100644
index 0000000000..d07bcb94db
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/tla2/a.js
@@ -0,0 +1,5 @@
+export default class Foo {
+  constructor(message) {
+    this.message = message;
+  }
+}
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/tla2/b.js b/tests/specs/run/top_level_await_nested/top_level_await/tla2/b.js
new file mode 100644
index 0000000000..68e357c1e9
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/tla2/b.js
@@ -0,0 +1,5 @@
+export default class Bar {
+  constructor(message) {
+    this.message = message;
+  }
+}
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/tla3/b.js b/tests/specs/run/top_level_await_nested/top_level_await/tla3/b.js
new file mode 100644
index 0000000000..d0349545e9
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/tla3/b.js
@@ -0,0 +1,7 @@
+import { foo } from "./timeout_loop.js";
+import { collection } from "../circular.js";
+
+console.log("collection in b", collection);
+console.log("foo in b", foo);
+
+export const a = "a";
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/tla3/timeout_loop.js b/tests/specs/run/top_level_await_nested/top_level_await/tla3/timeout_loop.js
new file mode 100644
index 0000000000..860e6cd2ae
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/tla3/timeout_loop.js
@@ -0,0 +1,23 @@
+export const foo = "foo";
+
+export function delay(ms) {
+  return new Promise((res) =>
+    setTimeout(() => {
+      res();
+    }, ms)
+  );
+}
+
+let i = 0;
+
+async function timeoutLoop() {
+  await delay(1000);
+  console.log("timeout loop", i);
+  i++;
+  if (i > 5) {
+    return;
+  }
+  timeoutLoop();
+}
+
+timeoutLoop();
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/top_level_await.js b/tests/specs/run/top_level_await_nested/top_level_await/top_level_await.js
new file mode 100644
index 0000000000..ea319ea124
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/top_level_await.js
@@ -0,0 +1,3 @@
+const buf = await Deno.readFile("./assets/hello.txt");
+const n = await Deno.stdout.write(buf);
+console.log(`\n\nwrite ${n}`);
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/top_level_await.out b/tests/specs/run/top_level_await_nested/top_level_await/top_level_await.out
new file mode 100644
index 0000000000..4b65d15fe3
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/top_level_await.out
@@ -0,0 +1,3 @@
+Hello world!
+
+write 12
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/top_level_await.ts b/tests/specs/run/top_level_await_nested/top_level_await/top_level_await.ts
new file mode 100644
index 0000000000..8d47ceb21e
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/top_level_await.ts
@@ -0,0 +1,3 @@
+const buf: Uint8Array = await Deno.readFile("./assets/hello.txt");
+const n: number = await Deno.stdout.write(buf);
+console.log(`\n\nwrite ${n}`);
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/top_level_for_await.js b/tests/specs/run/top_level_await_nested/top_level_await/top_level_for_await.js
new file mode 100644
index 0000000000..a330f6c711
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/top_level_for_await.js
@@ -0,0 +1,10 @@
+function* asyncGenerator() {
+  let i = 0;
+  while (i < 3) {
+    yield i++;
+  }
+}
+
+for await (const num of asyncGenerator()) {
+  console.log(num);
+}
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/top_level_for_await.out b/tests/specs/run/top_level_await_nested/top_level_await/top_level_for_await.out
new file mode 100644
index 0000000000..4539bbf2d2
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/top_level_for_await.out
@@ -0,0 +1,3 @@
+0
+1
+2
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/top_level_for_await.ts b/tests/specs/run/top_level_await_nested/top_level_await/top_level_for_await.ts
new file mode 100644
index 0000000000..9179322d78
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/top_level_for_await.ts
@@ -0,0 +1,10 @@
+async function* asyncGenerator(): AsyncIterableIterator<number> {
+  let i = 0;
+  while (i < 3) {
+    yield i++;
+  }
+}
+
+for await (const num of asyncGenerator()) {
+  console.log(num);
+}
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/unresolved.js b/tests/specs/run/top_level_await_nested/top_level_await/unresolved.js
new file mode 100644
index 0000000000..231a8cd634
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/unresolved.js
@@ -0,0 +1 @@
+await new Promise(() => {});
diff --git a/tests/specs/run/top_level_await_nested/top_level_await/unresolved.out b/tests/specs/run/top_level_await_nested/top_level_await/unresolved.out
new file mode 100644
index 0000000000..1f4ea5d382
--- /dev/null
+++ b/tests/specs/run/top_level_await_nested/top_level_await/unresolved.out
@@ -0,0 +1,4 @@
+error: Top-level await promise never resolved
+await new Promise(() => {});
+^
+    at <anonymous> ([WILDCARD]top_level_await/unresolved.js:1:1)
diff --git a/tests/specs/run/top_level_await_order/__test__.jsonc b/tests/specs/run/top_level_await_order/__test__.jsonc
new file mode 100644
index 0000000000..65d00d607d
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read top_level_await/order.js",
+  "output": "top_level_await/order.out"
+}
diff --git a/tests/specs/run/top_level_await_order/top_level_await/circular.js b/tests/specs/run/top_level_await_order/top_level_await/circular.js
new file mode 100644
index 0000000000..ff2964b6a5
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/circular.js
@@ -0,0 +1,8 @@
+import { foo } from "./tla3/timeout_loop.js";
+
+export const collection = [];
+
+const mod = await import("./tla3/b.js");
+
+console.log("foo in main", foo);
+console.log("mod", mod);
diff --git a/tests/specs/run/top_level_await_order/top_level_await/circular.out b/tests/specs/run/top_level_await_order/top_level_await/circular.out
new file mode 100644
index 0000000000..c889789613
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/circular.out
@@ -0,0 +1,10 @@
+timeout loop 0
+timeout loop 1
+timeout loop 2
+timeout loop 3
+timeout loop 4
+timeout loop 5
+error: Top-level await promise never resolved
+const mod = await import("./tla3/b.js");
+            ^
+    at <anonymous> ([WILDCARD]/top_level_await/circular.js:5:13)
diff --git a/tests/specs/run/top_level_await_order/top_level_await/loop.js b/tests/specs/run/top_level_await_order/top_level_await/loop.js
new file mode 100644
index 0000000000..415db5ec78
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/loop.js
@@ -0,0 +1,20 @@
+const importsDir = Deno.readDirSync(
+  Deno.realPathSync("./run/top_level_await/tla2"),
+);
+
+const resolvedPaths = [];
+
+for (const { name } of importsDir) {
+  const filePath = Deno.realPathSync(`./run/top_level_await/tla2/${name}`);
+  resolvedPaths.push(filePath);
+}
+
+resolvedPaths.sort();
+
+for (const filePath of resolvedPaths) {
+  console.log("loading", filePath);
+  const mod = await import(`file://${filePath}`);
+  console.log("loaded", mod);
+}
+
+console.log("all loaded");
diff --git a/tests/specs/run/top_level_await_order/top_level_await/loop.out b/tests/specs/run/top_level_await_order/top_level_await/loop.out
new file mode 100644
index 0000000000..1bdffbf660
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/loop.out
@@ -0,0 +1,5 @@
+loading [WILDCARD]a.js
+loaded [Module: null prototype] { default: [class Foo] }
+loading [WILDCARD]b.js
+loaded [Module: null prototype] { default: [class Bar] }
+all loaded
diff --git a/tests/specs/run/top_level_await_order/top_level_await/nested.out b/tests/specs/run/top_level_await_order/top_level_await/nested.out
new file mode 100644
index 0000000000..8a1218a102
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/nested.out
@@ -0,0 +1,5 @@
+1
+2
+3
+4
+5
diff --git a/tests/specs/run/top_level_await_order/top_level_await/nested/a.js b/tests/specs/run/top_level_await_order/top_level_await/nested/a.js
new file mode 100644
index 0000000000..74837d4ba1
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/nested/a.js
@@ -0,0 +1,3 @@
+console.log(2);
+await import("./b.js");
+console.log(4);
diff --git a/tests/specs/run/top_level_await_order/top_level_await/nested/b.js b/tests/specs/run/top_level_await_order/top_level_await/nested/b.js
new file mode 100644
index 0000000000..3bd241b50e
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/nested/b.js
@@ -0,0 +1 @@
+console.log(3);
diff --git a/tests/specs/run/top_level_await_order/top_level_await/nested/main.js b/tests/specs/run/top_level_await_order/top_level_await/nested/main.js
new file mode 100644
index 0000000000..ed46a47175
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/nested/main.js
@@ -0,0 +1,3 @@
+console.log(1);
+await import("./a.js");
+console.log(5);
diff --git a/tests/specs/run/top_level_await_order/top_level_await/order.js b/tests/specs/run/top_level_await_order/top_level_await/order.js
new file mode 100644
index 0000000000..30659cdfbf
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/order.js
@@ -0,0 +1,21 @@
+// Ported from Node
+// https://github.com/nodejs/node/blob/54746bb763ebea0dc7e99d88ff4b379bcd680964/test/es-module/test-esm-tla.mjs
+
+const { default: order } = await import("./tla/parent.js");
+
+console.log("order", JSON.stringify(order));
+
+if (
+  !(
+    order[0] === "order" &&
+    order[1] === "b" &&
+    order[2] === "c" &&
+    order[3] === "d" &&
+    order[4] === "a" &&
+    order[5] === "parent"
+  )
+) {
+  throw new Error("TLA wrong order");
+}
+
+console.log("TLA order correct");
diff --git a/tests/specs/run/top_level_await_order/top_level_await/order.out b/tests/specs/run/top_level_await_order/top_level_await/order.out
new file mode 100644
index 0000000000..4cc27858cf
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/order.out
@@ -0,0 +1,2 @@
+order ["order","b","c","d","a","parent"]
+TLA order correct
diff --git a/tests/specs/run/top_level_await_order/top_level_await/tla/a.js b/tests/specs/run/top_level_await_order/top_level_await/tla/a.js
new file mode 100644
index 0000000000..c3ef3f7dbc
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/tla/a.js
@@ -0,0 +1,3 @@
+import order from "./order.js";
+
+order.push("b");
diff --git a/tests/specs/run/top_level_await_order/top_level_await/tla/b.js b/tests/specs/run/top_level_await_order/top_level_await/tla/b.js
new file mode 100644
index 0000000000..3271c92d8f
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/tla/b.js
@@ -0,0 +1,7 @@
+import order from "./order.js";
+
+await new Promise((resolve) => {
+  setTimeout(resolve, 200);
+});
+
+order.push("a");
diff --git a/tests/specs/run/top_level_await_order/top_level_await/tla/c.js b/tests/specs/run/top_level_await_order/top_level_await/tla/c.js
new file mode 100644
index 0000000000..806eb0a8be
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/tla/c.js
@@ -0,0 +1,3 @@
+import order from "./order.js";
+
+order.push("c");
diff --git a/tests/specs/run/top_level_await_order/top_level_await/tla/d.js b/tests/specs/run/top_level_await_order/top_level_await/tla/d.js
new file mode 100644
index 0000000000..283ebf817f
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/tla/d.js
@@ -0,0 +1,8 @@
+import order from "./order.js";
+
+const end = Date.now() + 500;
+while (end < Date.now()) {
+  // pass
+}
+
+order.push("d");
diff --git a/tests/specs/run/top_level_await_order/top_level_await/tla/order.js b/tests/specs/run/top_level_await_order/top_level_await/tla/order.js
new file mode 100644
index 0000000000..f213a562ce
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/tla/order.js
@@ -0,0 +1 @@
+export default ["order"];
diff --git a/tests/specs/run/top_level_await_order/top_level_await/tla/parent.js b/tests/specs/run/top_level_await_order/top_level_await/tla/parent.js
new file mode 100644
index 0000000000..1ecc154634
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/tla/parent.js
@@ -0,0 +1,9 @@
+import order from "./order.js";
+import "./a.js";
+import "./b.js";
+import "./c.js";
+import "./d.js";
+
+order.push("parent");
+
+export default order;
diff --git a/tests/specs/run/top_level_await_order/top_level_await/tla2/a.js b/tests/specs/run/top_level_await_order/top_level_await/tla2/a.js
new file mode 100644
index 0000000000..d07bcb94db
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/tla2/a.js
@@ -0,0 +1,5 @@
+export default class Foo {
+  constructor(message) {
+    this.message = message;
+  }
+}
diff --git a/tests/specs/run/top_level_await_order/top_level_await/tla2/b.js b/tests/specs/run/top_level_await_order/top_level_await/tla2/b.js
new file mode 100644
index 0000000000..68e357c1e9
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/tla2/b.js
@@ -0,0 +1,5 @@
+export default class Bar {
+  constructor(message) {
+    this.message = message;
+  }
+}
diff --git a/tests/specs/run/top_level_await_order/top_level_await/tla3/b.js b/tests/specs/run/top_level_await_order/top_level_await/tla3/b.js
new file mode 100644
index 0000000000..d0349545e9
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/tla3/b.js
@@ -0,0 +1,7 @@
+import { foo } from "./timeout_loop.js";
+import { collection } from "../circular.js";
+
+console.log("collection in b", collection);
+console.log("foo in b", foo);
+
+export const a = "a";
diff --git a/tests/specs/run/top_level_await_order/top_level_await/tla3/timeout_loop.js b/tests/specs/run/top_level_await_order/top_level_await/tla3/timeout_loop.js
new file mode 100644
index 0000000000..860e6cd2ae
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/tla3/timeout_loop.js
@@ -0,0 +1,23 @@
+export const foo = "foo";
+
+export function delay(ms) {
+  return new Promise((res) =>
+    setTimeout(() => {
+      res();
+    }, ms)
+  );
+}
+
+let i = 0;
+
+async function timeoutLoop() {
+  await delay(1000);
+  console.log("timeout loop", i);
+  i++;
+  if (i > 5) {
+    return;
+  }
+  timeoutLoop();
+}
+
+timeoutLoop();
diff --git a/tests/specs/run/top_level_await_order/top_level_await/top_level_await.js b/tests/specs/run/top_level_await_order/top_level_await/top_level_await.js
new file mode 100644
index 0000000000..ea319ea124
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/top_level_await.js
@@ -0,0 +1,3 @@
+const buf = await Deno.readFile("./assets/hello.txt");
+const n = await Deno.stdout.write(buf);
+console.log(`\n\nwrite ${n}`);
diff --git a/tests/specs/run/top_level_await_order/top_level_await/top_level_await.out b/tests/specs/run/top_level_await_order/top_level_await/top_level_await.out
new file mode 100644
index 0000000000..4b65d15fe3
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/top_level_await.out
@@ -0,0 +1,3 @@
+Hello world!
+
+write 12
diff --git a/tests/specs/run/top_level_await_order/top_level_await/top_level_await.ts b/tests/specs/run/top_level_await_order/top_level_await/top_level_await.ts
new file mode 100644
index 0000000000..8d47ceb21e
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/top_level_await.ts
@@ -0,0 +1,3 @@
+const buf: Uint8Array = await Deno.readFile("./assets/hello.txt");
+const n: number = await Deno.stdout.write(buf);
+console.log(`\n\nwrite ${n}`);
diff --git a/tests/specs/run/top_level_await_order/top_level_await/top_level_for_await.js b/tests/specs/run/top_level_await_order/top_level_await/top_level_for_await.js
new file mode 100644
index 0000000000..a330f6c711
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/top_level_for_await.js
@@ -0,0 +1,10 @@
+function* asyncGenerator() {
+  let i = 0;
+  while (i < 3) {
+    yield i++;
+  }
+}
+
+for await (const num of asyncGenerator()) {
+  console.log(num);
+}
diff --git a/tests/specs/run/top_level_await_order/top_level_await/top_level_for_await.out b/tests/specs/run/top_level_await_order/top_level_await/top_level_for_await.out
new file mode 100644
index 0000000000..4539bbf2d2
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/top_level_for_await.out
@@ -0,0 +1,3 @@
+0
+1
+2
diff --git a/tests/specs/run/top_level_await_order/top_level_await/top_level_for_await.ts b/tests/specs/run/top_level_await_order/top_level_await/top_level_for_await.ts
new file mode 100644
index 0000000000..9179322d78
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/top_level_for_await.ts
@@ -0,0 +1,10 @@
+async function* asyncGenerator(): AsyncIterableIterator<number> {
+  let i = 0;
+  while (i < 3) {
+    yield i++;
+  }
+}
+
+for await (const num of asyncGenerator()) {
+  console.log(num);
+}
diff --git a/tests/specs/run/top_level_await_order/top_level_await/unresolved.js b/tests/specs/run/top_level_await_order/top_level_await/unresolved.js
new file mode 100644
index 0000000000..231a8cd634
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/unresolved.js
@@ -0,0 +1 @@
+await new Promise(() => {});
diff --git a/tests/specs/run/top_level_await_order/top_level_await/unresolved.out b/tests/specs/run/top_level_await_order/top_level_await/unresolved.out
new file mode 100644
index 0000000000..1f4ea5d382
--- /dev/null
+++ b/tests/specs/run/top_level_await_order/top_level_await/unresolved.out
@@ -0,0 +1,4 @@
+error: Top-level await promise never resolved
+await new Promise(() => {});
+^
+    at <anonymous> ([WILDCARD]top_level_await/unresolved.js:1:1)
diff --git a/tests/specs/run/top_level_await_ts/__test__.jsonc b/tests/specs/run/top_level_await_ts/__test__.jsonc
new file mode 100644
index 0000000000..15f937df19
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --allow-read top_level_await/top_level_await.ts",
+  "output": "top_level_await/top_level_await.out"
+}
diff --git a/tests/specs/run/top_level_await_ts/hello.txt b/tests/specs/run/top_level_await_ts/hello.txt
new file mode 100644
index 0000000000..6769dd60bd
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/hello.txt
@@ -0,0 +1 @@
+Hello world!
\ No newline at end of file
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/circular.js b/tests/specs/run/top_level_await_ts/top_level_await/circular.js
new file mode 100644
index 0000000000..ff2964b6a5
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/circular.js
@@ -0,0 +1,8 @@
+import { foo } from "./tla3/timeout_loop.js";
+
+export const collection = [];
+
+const mod = await import("./tla3/b.js");
+
+console.log("foo in main", foo);
+console.log("mod", mod);
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/circular.out b/tests/specs/run/top_level_await_ts/top_level_await/circular.out
new file mode 100644
index 0000000000..c889789613
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/circular.out
@@ -0,0 +1,10 @@
+timeout loop 0
+timeout loop 1
+timeout loop 2
+timeout loop 3
+timeout loop 4
+timeout loop 5
+error: Top-level await promise never resolved
+const mod = await import("./tla3/b.js");
+            ^
+    at <anonymous> ([WILDCARD]/top_level_await/circular.js:5:13)
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/loop.js b/tests/specs/run/top_level_await_ts/top_level_await/loop.js
new file mode 100644
index 0000000000..415db5ec78
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/loop.js
@@ -0,0 +1,20 @@
+const importsDir = Deno.readDirSync(
+  Deno.realPathSync("./run/top_level_await/tla2"),
+);
+
+const resolvedPaths = [];
+
+for (const { name } of importsDir) {
+  const filePath = Deno.realPathSync(`./run/top_level_await/tla2/${name}`);
+  resolvedPaths.push(filePath);
+}
+
+resolvedPaths.sort();
+
+for (const filePath of resolvedPaths) {
+  console.log("loading", filePath);
+  const mod = await import(`file://${filePath}`);
+  console.log("loaded", mod);
+}
+
+console.log("all loaded");
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/loop.out b/tests/specs/run/top_level_await_ts/top_level_await/loop.out
new file mode 100644
index 0000000000..1bdffbf660
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/loop.out
@@ -0,0 +1,5 @@
+loading [WILDCARD]a.js
+loaded [Module: null prototype] { default: [class Foo] }
+loading [WILDCARD]b.js
+loaded [Module: null prototype] { default: [class Bar] }
+all loaded
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/nested.out b/tests/specs/run/top_level_await_ts/top_level_await/nested.out
new file mode 100644
index 0000000000..8a1218a102
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/nested.out
@@ -0,0 +1,5 @@
+1
+2
+3
+4
+5
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/nested/a.js b/tests/specs/run/top_level_await_ts/top_level_await/nested/a.js
new file mode 100644
index 0000000000..74837d4ba1
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/nested/a.js
@@ -0,0 +1,3 @@
+console.log(2);
+await import("./b.js");
+console.log(4);
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/nested/b.js b/tests/specs/run/top_level_await_ts/top_level_await/nested/b.js
new file mode 100644
index 0000000000..3bd241b50e
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/nested/b.js
@@ -0,0 +1 @@
+console.log(3);
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/nested/main.js b/tests/specs/run/top_level_await_ts/top_level_await/nested/main.js
new file mode 100644
index 0000000000..ed46a47175
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/nested/main.js
@@ -0,0 +1,3 @@
+console.log(1);
+await import("./a.js");
+console.log(5);
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/order.js b/tests/specs/run/top_level_await_ts/top_level_await/order.js
new file mode 100644
index 0000000000..30659cdfbf
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/order.js
@@ -0,0 +1,21 @@
+// Ported from Node
+// https://github.com/nodejs/node/blob/54746bb763ebea0dc7e99d88ff4b379bcd680964/test/es-module/test-esm-tla.mjs
+
+const { default: order } = await import("./tla/parent.js");
+
+console.log("order", JSON.stringify(order));
+
+if (
+  !(
+    order[0] === "order" &&
+    order[1] === "b" &&
+    order[2] === "c" &&
+    order[3] === "d" &&
+    order[4] === "a" &&
+    order[5] === "parent"
+  )
+) {
+  throw new Error("TLA wrong order");
+}
+
+console.log("TLA order correct");
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/order.out b/tests/specs/run/top_level_await_ts/top_level_await/order.out
new file mode 100644
index 0000000000..4cc27858cf
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/order.out
@@ -0,0 +1,2 @@
+order ["order","b","c","d","a","parent"]
+TLA order correct
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/tla/a.js b/tests/specs/run/top_level_await_ts/top_level_await/tla/a.js
new file mode 100644
index 0000000000..c3ef3f7dbc
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/tla/a.js
@@ -0,0 +1,3 @@
+import order from "./order.js";
+
+order.push("b");
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/tla/b.js b/tests/specs/run/top_level_await_ts/top_level_await/tla/b.js
new file mode 100644
index 0000000000..3271c92d8f
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/tla/b.js
@@ -0,0 +1,7 @@
+import order from "./order.js";
+
+await new Promise((resolve) => {
+  setTimeout(resolve, 200);
+});
+
+order.push("a");
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/tla/c.js b/tests/specs/run/top_level_await_ts/top_level_await/tla/c.js
new file mode 100644
index 0000000000..806eb0a8be
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/tla/c.js
@@ -0,0 +1,3 @@
+import order from "./order.js";
+
+order.push("c");
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/tla/d.js b/tests/specs/run/top_level_await_ts/top_level_await/tla/d.js
new file mode 100644
index 0000000000..283ebf817f
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/tla/d.js
@@ -0,0 +1,8 @@
+import order from "./order.js";
+
+const end = Date.now() + 500;
+while (end < Date.now()) {
+  // pass
+}
+
+order.push("d");
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/tla/order.js b/tests/specs/run/top_level_await_ts/top_level_await/tla/order.js
new file mode 100644
index 0000000000..f213a562ce
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/tla/order.js
@@ -0,0 +1 @@
+export default ["order"];
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/tla/parent.js b/tests/specs/run/top_level_await_ts/top_level_await/tla/parent.js
new file mode 100644
index 0000000000..1ecc154634
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/tla/parent.js
@@ -0,0 +1,9 @@
+import order from "./order.js";
+import "./a.js";
+import "./b.js";
+import "./c.js";
+import "./d.js";
+
+order.push("parent");
+
+export default order;
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/tla2/a.js b/tests/specs/run/top_level_await_ts/top_level_await/tla2/a.js
new file mode 100644
index 0000000000..d07bcb94db
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/tla2/a.js
@@ -0,0 +1,5 @@
+export default class Foo {
+  constructor(message) {
+    this.message = message;
+  }
+}
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/tla2/b.js b/tests/specs/run/top_level_await_ts/top_level_await/tla2/b.js
new file mode 100644
index 0000000000..68e357c1e9
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/tla2/b.js
@@ -0,0 +1,5 @@
+export default class Bar {
+  constructor(message) {
+    this.message = message;
+  }
+}
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/tla3/b.js b/tests/specs/run/top_level_await_ts/top_level_await/tla3/b.js
new file mode 100644
index 0000000000..d0349545e9
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/tla3/b.js
@@ -0,0 +1,7 @@
+import { foo } from "./timeout_loop.js";
+import { collection } from "../circular.js";
+
+console.log("collection in b", collection);
+console.log("foo in b", foo);
+
+export const a = "a";
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/tla3/timeout_loop.js b/tests/specs/run/top_level_await_ts/top_level_await/tla3/timeout_loop.js
new file mode 100644
index 0000000000..860e6cd2ae
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/tla3/timeout_loop.js
@@ -0,0 +1,23 @@
+export const foo = "foo";
+
+export function delay(ms) {
+  return new Promise((res) =>
+    setTimeout(() => {
+      res();
+    }, ms)
+  );
+}
+
+let i = 0;
+
+async function timeoutLoop() {
+  await delay(1000);
+  console.log("timeout loop", i);
+  i++;
+  if (i > 5) {
+    return;
+  }
+  timeoutLoop();
+}
+
+timeoutLoop();
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/top_level_await.js b/tests/specs/run/top_level_await_ts/top_level_await/top_level_await.js
new file mode 100644
index 0000000000..ea319ea124
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/top_level_await.js
@@ -0,0 +1,3 @@
+const buf = await Deno.readFile("./assets/hello.txt");
+const n = await Deno.stdout.write(buf);
+console.log(`\n\nwrite ${n}`);
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/top_level_await.out b/tests/specs/run/top_level_await_ts/top_level_await/top_level_await.out
new file mode 100644
index 0000000000..4b65d15fe3
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/top_level_await.out
@@ -0,0 +1,3 @@
+Hello world!
+
+write 12
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/top_level_await.ts b/tests/specs/run/top_level_await_ts/top_level_await/top_level_await.ts
new file mode 100644
index 0000000000..48f66545ac
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/top_level_await.ts
@@ -0,0 +1,3 @@
+const buf: Uint8Array = await Deno.readFile("./hello.txt");
+const n: number = await Deno.stdout.write(buf);
+console.log(`\n\nwrite ${n}`);
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/top_level_for_await.js b/tests/specs/run/top_level_await_ts/top_level_await/top_level_for_await.js
new file mode 100644
index 0000000000..a330f6c711
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/top_level_for_await.js
@@ -0,0 +1,10 @@
+function* asyncGenerator() {
+  let i = 0;
+  while (i < 3) {
+    yield i++;
+  }
+}
+
+for await (const num of asyncGenerator()) {
+  console.log(num);
+}
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/top_level_for_await.out b/tests/specs/run/top_level_await_ts/top_level_await/top_level_for_await.out
new file mode 100644
index 0000000000..4539bbf2d2
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/top_level_for_await.out
@@ -0,0 +1,3 @@
+0
+1
+2
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/top_level_for_await.ts b/tests/specs/run/top_level_await_ts/top_level_await/top_level_for_await.ts
new file mode 100644
index 0000000000..9179322d78
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/top_level_for_await.ts
@@ -0,0 +1,10 @@
+async function* asyncGenerator(): AsyncIterableIterator<number> {
+  let i = 0;
+  while (i < 3) {
+    yield i++;
+  }
+}
+
+for await (const num of asyncGenerator()) {
+  console.log(num);
+}
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/unresolved.js b/tests/specs/run/top_level_await_ts/top_level_await/unresolved.js
new file mode 100644
index 0000000000..231a8cd634
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/unresolved.js
@@ -0,0 +1 @@
+await new Promise(() => {});
diff --git a/tests/specs/run/top_level_await_ts/top_level_await/unresolved.out b/tests/specs/run/top_level_await_ts/top_level_await/unresolved.out
new file mode 100644
index 0000000000..1f4ea5d382
--- /dev/null
+++ b/tests/specs/run/top_level_await_ts/top_level_await/unresolved.out
@@ -0,0 +1,4 @@
+error: Top-level await promise never resolved
+await new Promise(() => {});
+^
+    at <anonymous> ([WILDCARD]top_level_await/unresolved.js:1:1)
diff --git a/tests/specs/run/top_level_await_unresolved/__test__.jsonc b/tests/specs/run/top_level_await_unresolved/__test__.jsonc
new file mode 100644
index 0000000000..a92774c1b8
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run top_level_await/unresolved.js",
+  "output": "top_level_await/unresolved.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/circular.js b/tests/specs/run/top_level_await_unresolved/top_level_await/circular.js
new file mode 100644
index 0000000000..ff2964b6a5
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/circular.js
@@ -0,0 +1,8 @@
+import { foo } from "./tla3/timeout_loop.js";
+
+export const collection = [];
+
+const mod = await import("./tla3/b.js");
+
+console.log("foo in main", foo);
+console.log("mod", mod);
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/circular.out b/tests/specs/run/top_level_await_unresolved/top_level_await/circular.out
new file mode 100644
index 0000000000..c889789613
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/circular.out
@@ -0,0 +1,10 @@
+timeout loop 0
+timeout loop 1
+timeout loop 2
+timeout loop 3
+timeout loop 4
+timeout loop 5
+error: Top-level await promise never resolved
+const mod = await import("./tla3/b.js");
+            ^
+    at <anonymous> ([WILDCARD]/top_level_await/circular.js:5:13)
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/loop.js b/tests/specs/run/top_level_await_unresolved/top_level_await/loop.js
new file mode 100644
index 0000000000..415db5ec78
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/loop.js
@@ -0,0 +1,20 @@
+const importsDir = Deno.readDirSync(
+  Deno.realPathSync("./run/top_level_await/tla2"),
+);
+
+const resolvedPaths = [];
+
+for (const { name } of importsDir) {
+  const filePath = Deno.realPathSync(`./run/top_level_await/tla2/${name}`);
+  resolvedPaths.push(filePath);
+}
+
+resolvedPaths.sort();
+
+for (const filePath of resolvedPaths) {
+  console.log("loading", filePath);
+  const mod = await import(`file://${filePath}`);
+  console.log("loaded", mod);
+}
+
+console.log("all loaded");
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/loop.out b/tests/specs/run/top_level_await_unresolved/top_level_await/loop.out
new file mode 100644
index 0000000000..1bdffbf660
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/loop.out
@@ -0,0 +1,5 @@
+loading [WILDCARD]a.js
+loaded [Module: null prototype] { default: [class Foo] }
+loading [WILDCARD]b.js
+loaded [Module: null prototype] { default: [class Bar] }
+all loaded
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/nested.out b/tests/specs/run/top_level_await_unresolved/top_level_await/nested.out
new file mode 100644
index 0000000000..8a1218a102
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/nested.out
@@ -0,0 +1,5 @@
+1
+2
+3
+4
+5
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/nested/a.js b/tests/specs/run/top_level_await_unresolved/top_level_await/nested/a.js
new file mode 100644
index 0000000000..74837d4ba1
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/nested/a.js
@@ -0,0 +1,3 @@
+console.log(2);
+await import("./b.js");
+console.log(4);
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/nested/b.js b/tests/specs/run/top_level_await_unresolved/top_level_await/nested/b.js
new file mode 100644
index 0000000000..3bd241b50e
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/nested/b.js
@@ -0,0 +1 @@
+console.log(3);
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/nested/main.js b/tests/specs/run/top_level_await_unresolved/top_level_await/nested/main.js
new file mode 100644
index 0000000000..ed46a47175
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/nested/main.js
@@ -0,0 +1,3 @@
+console.log(1);
+await import("./a.js");
+console.log(5);
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/order.js b/tests/specs/run/top_level_await_unresolved/top_level_await/order.js
new file mode 100644
index 0000000000..30659cdfbf
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/order.js
@@ -0,0 +1,21 @@
+// Ported from Node
+// https://github.com/nodejs/node/blob/54746bb763ebea0dc7e99d88ff4b379bcd680964/test/es-module/test-esm-tla.mjs
+
+const { default: order } = await import("./tla/parent.js");
+
+console.log("order", JSON.stringify(order));
+
+if (
+  !(
+    order[0] === "order" &&
+    order[1] === "b" &&
+    order[2] === "c" &&
+    order[3] === "d" &&
+    order[4] === "a" &&
+    order[5] === "parent"
+  )
+) {
+  throw new Error("TLA wrong order");
+}
+
+console.log("TLA order correct");
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/order.out b/tests/specs/run/top_level_await_unresolved/top_level_await/order.out
new file mode 100644
index 0000000000..4cc27858cf
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/order.out
@@ -0,0 +1,2 @@
+order ["order","b","c","d","a","parent"]
+TLA order correct
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/tla/a.js b/tests/specs/run/top_level_await_unresolved/top_level_await/tla/a.js
new file mode 100644
index 0000000000..c3ef3f7dbc
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/tla/a.js
@@ -0,0 +1,3 @@
+import order from "./order.js";
+
+order.push("b");
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/tla/b.js b/tests/specs/run/top_level_await_unresolved/top_level_await/tla/b.js
new file mode 100644
index 0000000000..3271c92d8f
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/tla/b.js
@@ -0,0 +1,7 @@
+import order from "./order.js";
+
+await new Promise((resolve) => {
+  setTimeout(resolve, 200);
+});
+
+order.push("a");
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/tla/c.js b/tests/specs/run/top_level_await_unresolved/top_level_await/tla/c.js
new file mode 100644
index 0000000000..806eb0a8be
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/tla/c.js
@@ -0,0 +1,3 @@
+import order from "./order.js";
+
+order.push("c");
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/tla/d.js b/tests/specs/run/top_level_await_unresolved/top_level_await/tla/d.js
new file mode 100644
index 0000000000..283ebf817f
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/tla/d.js
@@ -0,0 +1,8 @@
+import order from "./order.js";
+
+const end = Date.now() + 500;
+while (end < Date.now()) {
+  // pass
+}
+
+order.push("d");
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/tla/order.js b/tests/specs/run/top_level_await_unresolved/top_level_await/tla/order.js
new file mode 100644
index 0000000000..f213a562ce
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/tla/order.js
@@ -0,0 +1 @@
+export default ["order"];
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/tla/parent.js b/tests/specs/run/top_level_await_unresolved/top_level_await/tla/parent.js
new file mode 100644
index 0000000000..1ecc154634
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/tla/parent.js
@@ -0,0 +1,9 @@
+import order from "./order.js";
+import "./a.js";
+import "./b.js";
+import "./c.js";
+import "./d.js";
+
+order.push("parent");
+
+export default order;
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/tla2/a.js b/tests/specs/run/top_level_await_unresolved/top_level_await/tla2/a.js
new file mode 100644
index 0000000000..d07bcb94db
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/tla2/a.js
@@ -0,0 +1,5 @@
+export default class Foo {
+  constructor(message) {
+    this.message = message;
+  }
+}
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/tla2/b.js b/tests/specs/run/top_level_await_unresolved/top_level_await/tla2/b.js
new file mode 100644
index 0000000000..68e357c1e9
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/tla2/b.js
@@ -0,0 +1,5 @@
+export default class Bar {
+  constructor(message) {
+    this.message = message;
+  }
+}
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/tla3/b.js b/tests/specs/run/top_level_await_unresolved/top_level_await/tla3/b.js
new file mode 100644
index 0000000000..d0349545e9
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/tla3/b.js
@@ -0,0 +1,7 @@
+import { foo } from "./timeout_loop.js";
+import { collection } from "../circular.js";
+
+console.log("collection in b", collection);
+console.log("foo in b", foo);
+
+export const a = "a";
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/tla3/timeout_loop.js b/tests/specs/run/top_level_await_unresolved/top_level_await/tla3/timeout_loop.js
new file mode 100644
index 0000000000..860e6cd2ae
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/tla3/timeout_loop.js
@@ -0,0 +1,23 @@
+export const foo = "foo";
+
+export function delay(ms) {
+  return new Promise((res) =>
+    setTimeout(() => {
+      res();
+    }, ms)
+  );
+}
+
+let i = 0;
+
+async function timeoutLoop() {
+  await delay(1000);
+  console.log("timeout loop", i);
+  i++;
+  if (i > 5) {
+    return;
+  }
+  timeoutLoop();
+}
+
+timeoutLoop();
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/top_level_await.js b/tests/specs/run/top_level_await_unresolved/top_level_await/top_level_await.js
new file mode 100644
index 0000000000..ea319ea124
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/top_level_await.js
@@ -0,0 +1,3 @@
+const buf = await Deno.readFile("./assets/hello.txt");
+const n = await Deno.stdout.write(buf);
+console.log(`\n\nwrite ${n}`);
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/top_level_await.out b/tests/specs/run/top_level_await_unresolved/top_level_await/top_level_await.out
new file mode 100644
index 0000000000..4b65d15fe3
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/top_level_await.out
@@ -0,0 +1,3 @@
+Hello world!
+
+write 12
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/top_level_await.ts b/tests/specs/run/top_level_await_unresolved/top_level_await/top_level_await.ts
new file mode 100644
index 0000000000..8d47ceb21e
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/top_level_await.ts
@@ -0,0 +1,3 @@
+const buf: Uint8Array = await Deno.readFile("./assets/hello.txt");
+const n: number = await Deno.stdout.write(buf);
+console.log(`\n\nwrite ${n}`);
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/top_level_for_await.js b/tests/specs/run/top_level_await_unresolved/top_level_await/top_level_for_await.js
new file mode 100644
index 0000000000..a330f6c711
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/top_level_for_await.js
@@ -0,0 +1,10 @@
+function* asyncGenerator() {
+  let i = 0;
+  while (i < 3) {
+    yield i++;
+  }
+}
+
+for await (const num of asyncGenerator()) {
+  console.log(num);
+}
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/top_level_for_await.out b/tests/specs/run/top_level_await_unresolved/top_level_await/top_level_for_await.out
new file mode 100644
index 0000000000..4539bbf2d2
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/top_level_for_await.out
@@ -0,0 +1,3 @@
+0
+1
+2
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/top_level_for_await.ts b/tests/specs/run/top_level_await_unresolved/top_level_await/top_level_for_await.ts
new file mode 100644
index 0000000000..9179322d78
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/top_level_for_await.ts
@@ -0,0 +1,10 @@
+async function* asyncGenerator(): AsyncIterableIterator<number> {
+  let i = 0;
+  while (i < 3) {
+    yield i++;
+  }
+}
+
+for await (const num of asyncGenerator()) {
+  console.log(num);
+}
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/unresolved.js b/tests/specs/run/top_level_await_unresolved/top_level_await/unresolved.js
new file mode 100644
index 0000000000..231a8cd634
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/unresolved.js
@@ -0,0 +1 @@
+await new Promise(() => {});
diff --git a/tests/specs/run/top_level_await_unresolved/top_level_await/unresolved.out b/tests/specs/run/top_level_await_unresolved/top_level_await/unresolved.out
new file mode 100644
index 0000000000..1f4ea5d382
--- /dev/null
+++ b/tests/specs/run/top_level_await_unresolved/top_level_await/unresolved.out
@@ -0,0 +1,4 @@
+error: Top-level await promise never resolved
+await new Promise(() => {});
+^
+    at <anonymous> ([WILDCARD]top_level_await/unresolved.js:1:1)
diff --git a/tests/specs/run/top_level_for_await/__test__.jsonc b/tests/specs/run/top_level_for_await/__test__.jsonc
new file mode 100644
index 0000000000..198008560b
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet top_level_await/top_level_for_await.js",
+  "output": "top_level_await/top_level_for_await.out"
+}
diff --git a/tests/specs/run/top_level_for_await/top_level_await/circular.js b/tests/specs/run/top_level_for_await/top_level_await/circular.js
new file mode 100644
index 0000000000..ff2964b6a5
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/circular.js
@@ -0,0 +1,8 @@
+import { foo } from "./tla3/timeout_loop.js";
+
+export const collection = [];
+
+const mod = await import("./tla3/b.js");
+
+console.log("foo in main", foo);
+console.log("mod", mod);
diff --git a/tests/specs/run/top_level_for_await/top_level_await/circular.out b/tests/specs/run/top_level_for_await/top_level_await/circular.out
new file mode 100644
index 0000000000..c889789613
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/circular.out
@@ -0,0 +1,10 @@
+timeout loop 0
+timeout loop 1
+timeout loop 2
+timeout loop 3
+timeout loop 4
+timeout loop 5
+error: Top-level await promise never resolved
+const mod = await import("./tla3/b.js");
+            ^
+    at <anonymous> ([WILDCARD]/top_level_await/circular.js:5:13)
diff --git a/tests/specs/run/top_level_for_await/top_level_await/loop.js b/tests/specs/run/top_level_for_await/top_level_await/loop.js
new file mode 100644
index 0000000000..415db5ec78
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/loop.js
@@ -0,0 +1,20 @@
+const importsDir = Deno.readDirSync(
+  Deno.realPathSync("./run/top_level_await/tla2"),
+);
+
+const resolvedPaths = [];
+
+for (const { name } of importsDir) {
+  const filePath = Deno.realPathSync(`./run/top_level_await/tla2/${name}`);
+  resolvedPaths.push(filePath);
+}
+
+resolvedPaths.sort();
+
+for (const filePath of resolvedPaths) {
+  console.log("loading", filePath);
+  const mod = await import(`file://${filePath}`);
+  console.log("loaded", mod);
+}
+
+console.log("all loaded");
diff --git a/tests/specs/run/top_level_for_await/top_level_await/loop.out b/tests/specs/run/top_level_for_await/top_level_await/loop.out
new file mode 100644
index 0000000000..1bdffbf660
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/loop.out
@@ -0,0 +1,5 @@
+loading [WILDCARD]a.js
+loaded [Module: null prototype] { default: [class Foo] }
+loading [WILDCARD]b.js
+loaded [Module: null prototype] { default: [class Bar] }
+all loaded
diff --git a/tests/specs/run/top_level_for_await/top_level_await/nested.out b/tests/specs/run/top_level_for_await/top_level_await/nested.out
new file mode 100644
index 0000000000..8a1218a102
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/nested.out
@@ -0,0 +1,5 @@
+1
+2
+3
+4
+5
diff --git a/tests/specs/run/top_level_for_await/top_level_await/nested/a.js b/tests/specs/run/top_level_for_await/top_level_await/nested/a.js
new file mode 100644
index 0000000000..74837d4ba1
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/nested/a.js
@@ -0,0 +1,3 @@
+console.log(2);
+await import("./b.js");
+console.log(4);
diff --git a/tests/specs/run/top_level_for_await/top_level_await/nested/b.js b/tests/specs/run/top_level_for_await/top_level_await/nested/b.js
new file mode 100644
index 0000000000..3bd241b50e
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/nested/b.js
@@ -0,0 +1 @@
+console.log(3);
diff --git a/tests/specs/run/top_level_for_await/top_level_await/nested/main.js b/tests/specs/run/top_level_for_await/top_level_await/nested/main.js
new file mode 100644
index 0000000000..ed46a47175
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/nested/main.js
@@ -0,0 +1,3 @@
+console.log(1);
+await import("./a.js");
+console.log(5);
diff --git a/tests/specs/run/top_level_for_await/top_level_await/order.js b/tests/specs/run/top_level_for_await/top_level_await/order.js
new file mode 100644
index 0000000000..30659cdfbf
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/order.js
@@ -0,0 +1,21 @@
+// Ported from Node
+// https://github.com/nodejs/node/blob/54746bb763ebea0dc7e99d88ff4b379bcd680964/test/es-module/test-esm-tla.mjs
+
+const { default: order } = await import("./tla/parent.js");
+
+console.log("order", JSON.stringify(order));
+
+if (
+  !(
+    order[0] === "order" &&
+    order[1] === "b" &&
+    order[2] === "c" &&
+    order[3] === "d" &&
+    order[4] === "a" &&
+    order[5] === "parent"
+  )
+) {
+  throw new Error("TLA wrong order");
+}
+
+console.log("TLA order correct");
diff --git a/tests/specs/run/top_level_for_await/top_level_await/order.out b/tests/specs/run/top_level_for_await/top_level_await/order.out
new file mode 100644
index 0000000000..4cc27858cf
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/order.out
@@ -0,0 +1,2 @@
+order ["order","b","c","d","a","parent"]
+TLA order correct
diff --git a/tests/specs/run/top_level_for_await/top_level_await/tla/a.js b/tests/specs/run/top_level_for_await/top_level_await/tla/a.js
new file mode 100644
index 0000000000..c3ef3f7dbc
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/tla/a.js
@@ -0,0 +1,3 @@
+import order from "./order.js";
+
+order.push("b");
diff --git a/tests/specs/run/top_level_for_await/top_level_await/tla/b.js b/tests/specs/run/top_level_for_await/top_level_await/tla/b.js
new file mode 100644
index 0000000000..3271c92d8f
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/tla/b.js
@@ -0,0 +1,7 @@
+import order from "./order.js";
+
+await new Promise((resolve) => {
+  setTimeout(resolve, 200);
+});
+
+order.push("a");
diff --git a/tests/specs/run/top_level_for_await/top_level_await/tla/c.js b/tests/specs/run/top_level_for_await/top_level_await/tla/c.js
new file mode 100644
index 0000000000..806eb0a8be
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/tla/c.js
@@ -0,0 +1,3 @@
+import order from "./order.js";
+
+order.push("c");
diff --git a/tests/specs/run/top_level_for_await/top_level_await/tla/d.js b/tests/specs/run/top_level_for_await/top_level_await/tla/d.js
new file mode 100644
index 0000000000..283ebf817f
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/tla/d.js
@@ -0,0 +1,8 @@
+import order from "./order.js";
+
+const end = Date.now() + 500;
+while (end < Date.now()) {
+  // pass
+}
+
+order.push("d");
diff --git a/tests/specs/run/top_level_for_await/top_level_await/tla/order.js b/tests/specs/run/top_level_for_await/top_level_await/tla/order.js
new file mode 100644
index 0000000000..f213a562ce
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/tla/order.js
@@ -0,0 +1 @@
+export default ["order"];
diff --git a/tests/specs/run/top_level_for_await/top_level_await/tla/parent.js b/tests/specs/run/top_level_for_await/top_level_await/tla/parent.js
new file mode 100644
index 0000000000..1ecc154634
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/tla/parent.js
@@ -0,0 +1,9 @@
+import order from "./order.js";
+import "./a.js";
+import "./b.js";
+import "./c.js";
+import "./d.js";
+
+order.push("parent");
+
+export default order;
diff --git a/tests/specs/run/top_level_for_await/top_level_await/tla2/a.js b/tests/specs/run/top_level_for_await/top_level_await/tla2/a.js
new file mode 100644
index 0000000000..d07bcb94db
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/tla2/a.js
@@ -0,0 +1,5 @@
+export default class Foo {
+  constructor(message) {
+    this.message = message;
+  }
+}
diff --git a/tests/specs/run/top_level_for_await/top_level_await/tla2/b.js b/tests/specs/run/top_level_for_await/top_level_await/tla2/b.js
new file mode 100644
index 0000000000..68e357c1e9
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/tla2/b.js
@@ -0,0 +1,5 @@
+export default class Bar {
+  constructor(message) {
+    this.message = message;
+  }
+}
diff --git a/tests/specs/run/top_level_for_await/top_level_await/tla3/b.js b/tests/specs/run/top_level_for_await/top_level_await/tla3/b.js
new file mode 100644
index 0000000000..d0349545e9
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/tla3/b.js
@@ -0,0 +1,7 @@
+import { foo } from "./timeout_loop.js";
+import { collection } from "../circular.js";
+
+console.log("collection in b", collection);
+console.log("foo in b", foo);
+
+export const a = "a";
diff --git a/tests/specs/run/top_level_for_await/top_level_await/tla3/timeout_loop.js b/tests/specs/run/top_level_for_await/top_level_await/tla3/timeout_loop.js
new file mode 100644
index 0000000000..860e6cd2ae
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/tla3/timeout_loop.js
@@ -0,0 +1,23 @@
+export const foo = "foo";
+
+export function delay(ms) {
+  return new Promise((res) =>
+    setTimeout(() => {
+      res();
+    }, ms)
+  );
+}
+
+let i = 0;
+
+async function timeoutLoop() {
+  await delay(1000);
+  console.log("timeout loop", i);
+  i++;
+  if (i > 5) {
+    return;
+  }
+  timeoutLoop();
+}
+
+timeoutLoop();
diff --git a/tests/specs/run/top_level_for_await/top_level_await/top_level_await.js b/tests/specs/run/top_level_for_await/top_level_await/top_level_await.js
new file mode 100644
index 0000000000..ea319ea124
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/top_level_await.js
@@ -0,0 +1,3 @@
+const buf = await Deno.readFile("./assets/hello.txt");
+const n = await Deno.stdout.write(buf);
+console.log(`\n\nwrite ${n}`);
diff --git a/tests/specs/run/top_level_for_await/top_level_await/top_level_await.out b/tests/specs/run/top_level_for_await/top_level_await/top_level_await.out
new file mode 100644
index 0000000000..4b65d15fe3
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/top_level_await.out
@@ -0,0 +1,3 @@
+Hello world!
+
+write 12
diff --git a/tests/specs/run/top_level_for_await/top_level_await/top_level_await.ts b/tests/specs/run/top_level_for_await/top_level_await/top_level_await.ts
new file mode 100644
index 0000000000..8d47ceb21e
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/top_level_await.ts
@@ -0,0 +1,3 @@
+const buf: Uint8Array = await Deno.readFile("./assets/hello.txt");
+const n: number = await Deno.stdout.write(buf);
+console.log(`\n\nwrite ${n}`);
diff --git a/tests/specs/run/top_level_for_await/top_level_await/top_level_for_await.js b/tests/specs/run/top_level_for_await/top_level_await/top_level_for_await.js
new file mode 100644
index 0000000000..a330f6c711
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/top_level_for_await.js
@@ -0,0 +1,10 @@
+function* asyncGenerator() {
+  let i = 0;
+  while (i < 3) {
+    yield i++;
+  }
+}
+
+for await (const num of asyncGenerator()) {
+  console.log(num);
+}
diff --git a/tests/specs/run/top_level_for_await/top_level_await/top_level_for_await.out b/tests/specs/run/top_level_for_await/top_level_await/top_level_for_await.out
new file mode 100644
index 0000000000..4539bbf2d2
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/top_level_for_await.out
@@ -0,0 +1,3 @@
+0
+1
+2
diff --git a/tests/specs/run/top_level_for_await/top_level_await/top_level_for_await.ts b/tests/specs/run/top_level_for_await/top_level_await/top_level_for_await.ts
new file mode 100644
index 0000000000..9179322d78
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/top_level_for_await.ts
@@ -0,0 +1,10 @@
+async function* asyncGenerator(): AsyncIterableIterator<number> {
+  let i = 0;
+  while (i < 3) {
+    yield i++;
+  }
+}
+
+for await (const num of asyncGenerator()) {
+  console.log(num);
+}
diff --git a/tests/specs/run/top_level_for_await/top_level_await/unresolved.js b/tests/specs/run/top_level_for_await/top_level_await/unresolved.js
new file mode 100644
index 0000000000..231a8cd634
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/unresolved.js
@@ -0,0 +1 @@
+await new Promise(() => {});
diff --git a/tests/specs/run/top_level_for_await/top_level_await/unresolved.out b/tests/specs/run/top_level_for_await/top_level_await/unresolved.out
new file mode 100644
index 0000000000..1f4ea5d382
--- /dev/null
+++ b/tests/specs/run/top_level_for_await/top_level_await/unresolved.out
@@ -0,0 +1,4 @@
+error: Top-level await promise never resolved
+await new Promise(() => {});
+^
+    at <anonymous> ([WILDCARD]top_level_await/unresolved.js:1:1)
diff --git a/tests/specs/run/top_level_for_await_ts/__test__.jsonc b/tests/specs/run/top_level_for_await_ts/__test__.jsonc
new file mode 100644
index 0000000000..22314e8e0d
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet top_level_await/top_level_for_await.ts",
+  "output": "top_level_await/top_level_for_await.out"
+}
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/circular.js b/tests/specs/run/top_level_for_await_ts/top_level_await/circular.js
new file mode 100644
index 0000000000..ff2964b6a5
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/circular.js
@@ -0,0 +1,8 @@
+import { foo } from "./tla3/timeout_loop.js";
+
+export const collection = [];
+
+const mod = await import("./tla3/b.js");
+
+console.log("foo in main", foo);
+console.log("mod", mod);
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/circular.out b/tests/specs/run/top_level_for_await_ts/top_level_await/circular.out
new file mode 100644
index 0000000000..c889789613
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/circular.out
@@ -0,0 +1,10 @@
+timeout loop 0
+timeout loop 1
+timeout loop 2
+timeout loop 3
+timeout loop 4
+timeout loop 5
+error: Top-level await promise never resolved
+const mod = await import("./tla3/b.js");
+            ^
+    at <anonymous> ([WILDCARD]/top_level_await/circular.js:5:13)
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/loop.js b/tests/specs/run/top_level_for_await_ts/top_level_await/loop.js
new file mode 100644
index 0000000000..415db5ec78
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/loop.js
@@ -0,0 +1,20 @@
+const importsDir = Deno.readDirSync(
+  Deno.realPathSync("./run/top_level_await/tla2"),
+);
+
+const resolvedPaths = [];
+
+for (const { name } of importsDir) {
+  const filePath = Deno.realPathSync(`./run/top_level_await/tla2/${name}`);
+  resolvedPaths.push(filePath);
+}
+
+resolvedPaths.sort();
+
+for (const filePath of resolvedPaths) {
+  console.log("loading", filePath);
+  const mod = await import(`file://${filePath}`);
+  console.log("loaded", mod);
+}
+
+console.log("all loaded");
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/loop.out b/tests/specs/run/top_level_for_await_ts/top_level_await/loop.out
new file mode 100644
index 0000000000..1bdffbf660
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/loop.out
@@ -0,0 +1,5 @@
+loading [WILDCARD]a.js
+loaded [Module: null prototype] { default: [class Foo] }
+loading [WILDCARD]b.js
+loaded [Module: null prototype] { default: [class Bar] }
+all loaded
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/nested.out b/tests/specs/run/top_level_for_await_ts/top_level_await/nested.out
new file mode 100644
index 0000000000..8a1218a102
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/nested.out
@@ -0,0 +1,5 @@
+1
+2
+3
+4
+5
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/nested/a.js b/tests/specs/run/top_level_for_await_ts/top_level_await/nested/a.js
new file mode 100644
index 0000000000..74837d4ba1
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/nested/a.js
@@ -0,0 +1,3 @@
+console.log(2);
+await import("./b.js");
+console.log(4);
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/nested/b.js b/tests/specs/run/top_level_for_await_ts/top_level_await/nested/b.js
new file mode 100644
index 0000000000..3bd241b50e
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/nested/b.js
@@ -0,0 +1 @@
+console.log(3);
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/nested/main.js b/tests/specs/run/top_level_for_await_ts/top_level_await/nested/main.js
new file mode 100644
index 0000000000..ed46a47175
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/nested/main.js
@@ -0,0 +1,3 @@
+console.log(1);
+await import("./a.js");
+console.log(5);
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/order.js b/tests/specs/run/top_level_for_await_ts/top_level_await/order.js
new file mode 100644
index 0000000000..30659cdfbf
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/order.js
@@ -0,0 +1,21 @@
+// Ported from Node
+// https://github.com/nodejs/node/blob/54746bb763ebea0dc7e99d88ff4b379bcd680964/test/es-module/test-esm-tla.mjs
+
+const { default: order } = await import("./tla/parent.js");
+
+console.log("order", JSON.stringify(order));
+
+if (
+  !(
+    order[0] === "order" &&
+    order[1] === "b" &&
+    order[2] === "c" &&
+    order[3] === "d" &&
+    order[4] === "a" &&
+    order[5] === "parent"
+  )
+) {
+  throw new Error("TLA wrong order");
+}
+
+console.log("TLA order correct");
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/order.out b/tests/specs/run/top_level_for_await_ts/top_level_await/order.out
new file mode 100644
index 0000000000..4cc27858cf
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/order.out
@@ -0,0 +1,2 @@
+order ["order","b","c","d","a","parent"]
+TLA order correct
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/tla/a.js b/tests/specs/run/top_level_for_await_ts/top_level_await/tla/a.js
new file mode 100644
index 0000000000..c3ef3f7dbc
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/tla/a.js
@@ -0,0 +1,3 @@
+import order from "./order.js";
+
+order.push("b");
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/tla/b.js b/tests/specs/run/top_level_for_await_ts/top_level_await/tla/b.js
new file mode 100644
index 0000000000..3271c92d8f
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/tla/b.js
@@ -0,0 +1,7 @@
+import order from "./order.js";
+
+await new Promise((resolve) => {
+  setTimeout(resolve, 200);
+});
+
+order.push("a");
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/tla/c.js b/tests/specs/run/top_level_for_await_ts/top_level_await/tla/c.js
new file mode 100644
index 0000000000..806eb0a8be
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/tla/c.js
@@ -0,0 +1,3 @@
+import order from "./order.js";
+
+order.push("c");
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/tla/d.js b/tests/specs/run/top_level_for_await_ts/top_level_await/tla/d.js
new file mode 100644
index 0000000000..283ebf817f
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/tla/d.js
@@ -0,0 +1,8 @@
+import order from "./order.js";
+
+const end = Date.now() + 500;
+while (end < Date.now()) {
+  // pass
+}
+
+order.push("d");
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/tla/order.js b/tests/specs/run/top_level_for_await_ts/top_level_await/tla/order.js
new file mode 100644
index 0000000000..f213a562ce
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/tla/order.js
@@ -0,0 +1 @@
+export default ["order"];
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/tla/parent.js b/tests/specs/run/top_level_for_await_ts/top_level_await/tla/parent.js
new file mode 100644
index 0000000000..1ecc154634
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/tla/parent.js
@@ -0,0 +1,9 @@
+import order from "./order.js";
+import "./a.js";
+import "./b.js";
+import "./c.js";
+import "./d.js";
+
+order.push("parent");
+
+export default order;
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/tla2/a.js b/tests/specs/run/top_level_for_await_ts/top_level_await/tla2/a.js
new file mode 100644
index 0000000000..d07bcb94db
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/tla2/a.js
@@ -0,0 +1,5 @@
+export default class Foo {
+  constructor(message) {
+    this.message = message;
+  }
+}
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/tla2/b.js b/tests/specs/run/top_level_for_await_ts/top_level_await/tla2/b.js
new file mode 100644
index 0000000000..68e357c1e9
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/tla2/b.js
@@ -0,0 +1,5 @@
+export default class Bar {
+  constructor(message) {
+    this.message = message;
+  }
+}
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/tla3/b.js b/tests/specs/run/top_level_for_await_ts/top_level_await/tla3/b.js
new file mode 100644
index 0000000000..d0349545e9
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/tla3/b.js
@@ -0,0 +1,7 @@
+import { foo } from "./timeout_loop.js";
+import { collection } from "../circular.js";
+
+console.log("collection in b", collection);
+console.log("foo in b", foo);
+
+export const a = "a";
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/tla3/timeout_loop.js b/tests/specs/run/top_level_for_await_ts/top_level_await/tla3/timeout_loop.js
new file mode 100644
index 0000000000..860e6cd2ae
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/tla3/timeout_loop.js
@@ -0,0 +1,23 @@
+export const foo = "foo";
+
+export function delay(ms) {
+  return new Promise((res) =>
+    setTimeout(() => {
+      res();
+    }, ms)
+  );
+}
+
+let i = 0;
+
+async function timeoutLoop() {
+  await delay(1000);
+  console.log("timeout loop", i);
+  i++;
+  if (i > 5) {
+    return;
+  }
+  timeoutLoop();
+}
+
+timeoutLoop();
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/top_level_await.js b/tests/specs/run/top_level_for_await_ts/top_level_await/top_level_await.js
new file mode 100644
index 0000000000..ea319ea124
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/top_level_await.js
@@ -0,0 +1,3 @@
+const buf = await Deno.readFile("./assets/hello.txt");
+const n = await Deno.stdout.write(buf);
+console.log(`\n\nwrite ${n}`);
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/top_level_await.out b/tests/specs/run/top_level_for_await_ts/top_level_await/top_level_await.out
new file mode 100644
index 0000000000..4b65d15fe3
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/top_level_await.out
@@ -0,0 +1,3 @@
+Hello world!
+
+write 12
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/top_level_await.ts b/tests/specs/run/top_level_for_await_ts/top_level_await/top_level_await.ts
new file mode 100644
index 0000000000..8d47ceb21e
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/top_level_await.ts
@@ -0,0 +1,3 @@
+const buf: Uint8Array = await Deno.readFile("./assets/hello.txt");
+const n: number = await Deno.stdout.write(buf);
+console.log(`\n\nwrite ${n}`);
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/top_level_for_await.js b/tests/specs/run/top_level_for_await_ts/top_level_await/top_level_for_await.js
new file mode 100644
index 0000000000..a330f6c711
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/top_level_for_await.js
@@ -0,0 +1,10 @@
+function* asyncGenerator() {
+  let i = 0;
+  while (i < 3) {
+    yield i++;
+  }
+}
+
+for await (const num of asyncGenerator()) {
+  console.log(num);
+}
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/top_level_for_await.out b/tests/specs/run/top_level_for_await_ts/top_level_await/top_level_for_await.out
new file mode 100644
index 0000000000..4539bbf2d2
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/top_level_for_await.out
@@ -0,0 +1,3 @@
+0
+1
+2
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/top_level_for_await.ts b/tests/specs/run/top_level_for_await_ts/top_level_await/top_level_for_await.ts
new file mode 100644
index 0000000000..9179322d78
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/top_level_for_await.ts
@@ -0,0 +1,10 @@
+async function* asyncGenerator(): AsyncIterableIterator<number> {
+  let i = 0;
+  while (i < 3) {
+    yield i++;
+  }
+}
+
+for await (const num of asyncGenerator()) {
+  console.log(num);
+}
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/unresolved.js b/tests/specs/run/top_level_for_await_ts/top_level_await/unresolved.js
new file mode 100644
index 0000000000..231a8cd634
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/unresolved.js
@@ -0,0 +1 @@
+await new Promise(() => {});
diff --git a/tests/specs/run/top_level_for_await_ts/top_level_await/unresolved.out b/tests/specs/run/top_level_for_await_ts/top_level_await/unresolved.out
new file mode 100644
index 0000000000..1f4ea5d382
--- /dev/null
+++ b/tests/specs/run/top_level_for_await_ts/top_level_await/unresolved.out
@@ -0,0 +1,4 @@
+error: Top-level await promise never resolved
+await new Promise(() => {});
+^
+    at <anonymous> ([WILDCARD]top_level_await/unresolved.js:1:1)
diff --git a/tests/specs/run/ts_decorators/__test__.jsonc b/tests/specs/run/ts_decorators/__test__.jsonc
new file mode 100644
index 0000000000..96e7cdf308
--- /dev/null
+++ b/tests/specs/run/ts_decorators/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload --check decorators/experimental/ts/main.ts",
+  "output": "decorators/experimental/ts/main.out"
+}
diff --git a/tests/specs/run/ts_decorators/decorators/experimental/deno.json b/tests/specs/run/ts_decorators/decorators/experimental/deno.json
new file mode 100644
index 0000000000..504cd646e1
--- /dev/null
+++ b/tests/specs/run/ts_decorators/decorators/experimental/deno.json
@@ -0,0 +1,5 @@
+{
+  "compilerOptions": {
+    "experimentalDecorators": true
+  }
+}
diff --git a/tests/specs/run/ts_decorators/decorators/experimental/no_check/main.out b/tests/specs/run/ts_decorators/decorators/experimental/no_check/main.out
new file mode 100644
index 0000000000..015f7076e8
--- /dev/null
+++ b/tests/specs/run/ts_decorators/decorators/experimental/no_check/main.out
@@ -0,0 +1,3 @@
+a(): evaluated
+a(): called
+method
diff --git a/tests/specs/run/ts_decorators/decorators/experimental/no_check/main.ts b/tests/specs/run/ts_decorators/decorators/experimental/no_check/main.ts
new file mode 100644
index 0000000000..9f7ec550d5
--- /dev/null
+++ b/tests/specs/run/ts_decorators/decorators/experimental/no_check/main.ts
@@ -0,0 +1,21 @@
+// deno-lint-ignore-file
+function a() {
+  console.log("a(): evaluated");
+  return (
+    _target: any,
+    _propertyKey: string,
+    _descriptor: PropertyDescriptor,
+  ) => {
+    console.log("a(): called");
+  };
+}
+
+class B {
+  @a()
+  method() {
+    console.log("method");
+  }
+}
+
+const b = new B();
+b.method();
diff --git a/tests/specs/run/ts_decorators/decorators/experimental/runtime/main.out b/tests/specs/run/ts_decorators/decorators/experimental/runtime/main.out
new file mode 100644
index 0000000000..0fc1d4590e
--- /dev/null
+++ b/tests/specs/run/ts_decorators/decorators/experimental/runtime/main.out
@@ -0,0 +1,7 @@
+@A evaluated
+@B evaluated
+@B called
+@A called
+fn() called from @A
+fn() called from @B
+C.test() called
diff --git a/tests/specs/run/ts_decorators/decorators/experimental/runtime/main.ts b/tests/specs/run/ts_decorators/decorators/experimental/runtime/main.ts
new file mode 100644
index 0000000000..40a26bbd4d
--- /dev/null
+++ b/tests/specs/run/ts_decorators/decorators/experimental/runtime/main.ts
@@ -0,0 +1,42 @@
+// deno-lint-ignore-file
+function a() {
+  console.log("@A evaluated");
+  return function (
+    target: any,
+    propertyKey: string,
+    descriptor: PropertyDescriptor,
+  ) {
+    console.log("@A called");
+    const fn = descriptor.value;
+    descriptor.value = function () {
+      console.log("fn() called from @A");
+      fn();
+    };
+  };
+}
+
+function b() {
+  console.log("@B evaluated");
+  return function (
+    target: any,
+    propertyKey: string,
+    descriptor: PropertyDescriptor,
+  ) {
+    console.log("@B called");
+    const fn = descriptor.value;
+    descriptor.value = function () {
+      console.log("fn() called from @B");
+      fn();
+    };
+  };
+}
+
+class C {
+  @a()
+  @b()
+  static test() {
+    console.log("C.test() called");
+  }
+}
+
+C.test();
diff --git a/tests/specs/run/ts_decorators/decorators/experimental/ts/main.out b/tests/specs/run/ts_decorators/decorators/experimental/ts/main.out
new file mode 100644
index 0000000000..ea64fbaa63
--- /dev/null
+++ b/tests/specs/run/ts_decorators/decorators/experimental/ts/main.out
@@ -0,0 +1,3 @@
+Warning experimentalDecorators compiler option is deprecated and may be removed at any time
+Check [WILDCARD]
+SomeClass { someField: "asdf" }
diff --git a/tests/specs/run/ts_decorators/decorators/experimental/ts/main.ts b/tests/specs/run/ts_decorators/decorators/experimental/ts/main.ts
new file mode 100644
index 0000000000..95fba6cd48
--- /dev/null
+++ b/tests/specs/run/ts_decorators/decorators/experimental/ts/main.ts
@@ -0,0 +1,14 @@
+// deno-lint-ignore-file
+
+function Decorate() {
+  return function (constructor: any): any {
+    return class extends constructor {
+      protected someField: string = "asdf";
+    };
+  };
+}
+
+@Decorate()
+class SomeClass {}
+
+console.log(new SomeClass());
diff --git a/tests/specs/run/ts_decorators/decorators/tc39_proposal/main.out b/tests/specs/run/ts_decorators/decorators/tc39_proposal/main.out
new file mode 100644
index 0000000000..39394952e8
--- /dev/null
+++ b/tests/specs/run/ts_decorators/decorators/tc39_proposal/main.out
@@ -0,0 +1,3 @@
+starting m with arguments 1
+C.m 1
+ending m
diff --git a/tests/specs/run/ts_decorators/decorators/tc39_proposal/main.ts b/tests/specs/run/ts_decorators/decorators/tc39_proposal/main.ts
new file mode 100644
index 0000000000..00c8a85025
--- /dev/null
+++ b/tests/specs/run/ts_decorators/decorators/tc39_proposal/main.ts
@@ -0,0 +1,21 @@
+// deno-lint-ignore no-explicit-any
+function logged(value: any, { kind, name }: { kind: string; name: string }) {
+  if (kind === "method") {
+    return function (...args: unknown[]) {
+      console.log(`starting ${name} with arguments ${args.join(", ")}`);
+      // @ts-ignore this has implicit any type
+      const ret = value.call(this, ...args);
+      console.log(`ending ${name}`);
+      return ret;
+    };
+  }
+}
+
+class C {
+  @logged
+  m(arg: number) {
+    console.log("C.m", arg);
+  }
+}
+
+new C().m(1);
diff --git a/tests/specs/run/ts_import_from_js/005_more_imports.ts b/tests/specs/run/ts_import_from_js/005_more_imports.ts
new file mode 100644
index 0000000000..c69556be15
--- /dev/null
+++ b/tests/specs/run/ts_import_from_js/005_more_imports.ts
@@ -0,0 +1,11 @@
+import { printHello3, returnsFoo2, returnsHi } from "./mod1.ts";
+
+printHello3();
+
+if (returnsHi() !== "Hi") {
+  throw Error("Unexpected");
+}
+
+if (returnsFoo2() !== "Foo") {
+  throw Error("Unexpected");
+}
diff --git a/tests/specs/run/ts_import_from_js/__test__.jsonc b/tests/specs/run/ts_import_from_js/__test__.jsonc
new file mode 100644
index 0000000000..de11873cbc
--- /dev/null
+++ b/tests/specs/run/ts_import_from_js/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --quiet --reload ts_import_from_js/main.js",
+  "output": "ts_import_from_js/main.out"
+}
diff --git a/tests/specs/run/ts_import_from_js/mod1.ts b/tests/specs/run/ts_import_from_js/mod1.ts
new file mode 100644
index 0000000000..5e58f432ed
--- /dev/null
+++ b/tests/specs/run/ts_import_from_js/mod1.ts
@@ -0,0 +1,17 @@
+import { printHello2, returnsFoo } from "./subdir2/mod2.ts";
+
+export function returnsHi(): string {
+  return "Hi";
+}
+
+export function returnsFoo2(): string {
+  return returnsFoo();
+}
+
+export function printHello3() {
+  printHello2();
+}
+
+export function throwsError() {
+  throw Error("exception from mod1");
+}
diff --git a/tests/specs/run/ts_import_from_js/mod2.ts b/tests/specs/run/ts_import_from_js/mod2.ts
new file mode 100644
index 0000000000..ce1adc0e81
--- /dev/null
+++ b/tests/specs/run/ts_import_from_js/mod2.ts
@@ -0,0 +1 @@
+export { printHello } from "./print_hello.ts";
diff --git a/tests/specs/run/ts_import_from_js/print_hello.ts b/tests/specs/run/ts_import_from_js/print_hello.ts
new file mode 100644
index 0000000000..b9c0ad5275
--- /dev/null
+++ b/tests/specs/run/ts_import_from_js/print_hello.ts
@@ -0,0 +1,3 @@
+export function printHello() {
+  console.log("Hello");
+}
diff --git a/tests/specs/run/ts_import_from_js/subdir2/dynamic_import.ts b/tests/specs/run/ts_import_from_js/subdir2/dynamic_import.ts
new file mode 100644
index 0000000000..59beb64c33
--- /dev/null
+++ b/tests/specs/run/ts_import_from_js/subdir2/dynamic_import.ts
@@ -0,0 +1,4 @@
+(async () => {
+  const { printHello } = await import("../mod2.ts");
+  printHello();
+})();
diff --git a/tests/specs/run/ts_import_from_js/subdir2/mod2.ts b/tests/specs/run/ts_import_from_js/subdir2/mod2.ts
new file mode 100644
index 0000000000..9071d0aeb4
--- /dev/null
+++ b/tests/specs/run/ts_import_from_js/subdir2/mod2.ts
@@ -0,0 +1,9 @@
+import { printHello } from "../print_hello.ts";
+
+export function returnsFoo(): string {
+  return "Foo";
+}
+
+export function printHello2() {
+  printHello();
+}
diff --git a/tests/testdata/run/ts_import_from_js/deps.js b/tests/specs/run/ts_import_from_js/ts_import_from_js/deps.js
similarity index 100%
rename from tests/testdata/run/ts_import_from_js/deps.js
rename to tests/specs/run/ts_import_from_js/ts_import_from_js/deps.js
diff --git a/tests/testdata/run/ts_import_from_js/main.js b/tests/specs/run/ts_import_from_js/ts_import_from_js/main.js
similarity index 100%
rename from tests/testdata/run/ts_import_from_js/main.js
rename to tests/specs/run/ts_import_from_js/ts_import_from_js/main.js
diff --git a/tests/testdata/run/ts_import_from_js/main.out b/tests/specs/run/ts_import_from_js/ts_import_from_js/main.out
similarity index 100%
rename from tests/testdata/run/ts_import_from_js/main.out
rename to tests/specs/run/ts_import_from_js/ts_import_from_js/main.out
diff --git a/tests/specs/run/ts_type_imports/__test__.jsonc b/tests/specs/run/ts_type_imports/__test__.jsonc
new file mode 100644
index 0000000000..e9a925d1a8
--- /dev/null
+++ b/tests/specs/run/ts_type_imports/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload --check ts_type_imports.ts",
+  "output": "ts_type_imports.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/ts_type_imports.ts b/tests/specs/run/ts_type_imports/ts_type_imports.ts
similarity index 100%
rename from tests/testdata/run/ts_type_imports.ts
rename to tests/specs/run/ts_type_imports/ts_type_imports.ts
diff --git a/tests/testdata/run/ts_type_imports.ts.out b/tests/specs/run/ts_type_imports/ts_type_imports.ts.out
similarity index 100%
rename from tests/testdata/run/ts_type_imports.ts.out
rename to tests/specs/run/ts_type_imports/ts_type_imports.ts.out
diff --git a/tests/specs/run/ts_type_imports/ts_type_imports_foo.ts b/tests/specs/run/ts_type_imports/ts_type_imports_foo.ts
new file mode 100644
index 0000000000..db20773f63
--- /dev/null
+++ b/tests/specs/run/ts_type_imports/ts_type_imports_foo.ts
@@ -0,0 +1 @@
+export type Foo = Map<string, number>;
diff --git a/tests/specs/run/ts_type_only_import/__test__.jsonc b/tests/specs/run/ts_type_only_import/__test__.jsonc
new file mode 100644
index 0000000000..977a6aba7a
--- /dev/null
+++ b/tests/specs/run/ts_type_only_import/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload --check ts_type_only_import.ts",
+  "output": "ts_type_only_import.ts.out"
+}
diff --git a/tests/specs/run/ts_type_only_import/ts_type_only_import.d.ts b/tests/specs/run/ts_type_only_import/ts_type_only_import.d.ts
new file mode 100644
index 0000000000..d48e4b48ab
--- /dev/null
+++ b/tests/specs/run/ts_type_only_import/ts_type_only_import.d.ts
@@ -0,0 +1,3 @@
+export interface HelloWorld {
+  a: string;
+}
diff --git a/tests/testdata/run/ts_type_only_import.ts b/tests/specs/run/ts_type_only_import/ts_type_only_import.ts
similarity index 100%
rename from tests/testdata/run/ts_type_only_import.ts
rename to tests/specs/run/ts_type_only_import/ts_type_only_import.ts
diff --git a/tests/testdata/run/ts_type_only_import.ts.out b/tests/specs/run/ts_type_only_import/ts_type_only_import.ts.out
similarity index 100%
rename from tests/testdata/run/ts_type_only_import.ts.out
rename to tests/specs/run/ts_type_only_import/ts_type_only_import.ts.out
diff --git a/tests/specs/run/ts_without_extension/__test__.jsonc b/tests/specs/run/ts_without_extension/__test__.jsonc
new file mode 100644
index 0000000000..a6c713bf5a
--- /dev/null
+++ b/tests/specs/run/ts_without_extension/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --ext ts --check ts_without_extension",
+  "output": "ts_without_extension.out",
+  "exitCode": 0
+}
diff --git a/tests/specs/run/ts_without_extension/ts_without_extension b/tests/specs/run/ts_without_extension/ts_without_extension
new file mode 100644
index 0000000000..f10891d7a2
--- /dev/null
+++ b/tests/specs/run/ts_without_extension/ts_without_extension
@@ -0,0 +1,3 @@
+interface Lollipop {}
+
+console.log("executing typescript with no extension");
diff --git a/tests/specs/run/ts_without_extension/ts_without_extension.out b/tests/specs/run/ts_without_extension/ts_without_extension.out
new file mode 100644
index 0000000000..4f02dd4c33
--- /dev/null
+++ b/tests/specs/run/ts_without_extension/ts_without_extension.out
@@ -0,0 +1,2 @@
+Check [WILDCARD]/ts_without_extension
+executing typescript with no extension
diff --git a/tests/specs/run/tsx_imports/046_jsx_test.tsx b/tests/specs/run/tsx_imports/046_jsx_test.tsx
new file mode 100644
index 0000000000..5ed3ff2fab
--- /dev/null
+++ b/tests/specs/run/tsx_imports/046_jsx_test.tsx
@@ -0,0 +1,14 @@
+declare global {
+  export namespace JSX {
+    interface IntrinsicElements {
+      [elemName: string]: any;
+    }
+  }
+}
+const React = {
+  createElement(factory: any, props: any, ...children: any[]) {
+    return { factory, props, children };
+  },
+};
+const View = () => <div class="deno">land</div>;
+console.log(<View />);
diff --git a/tests/specs/run/tsx_imports/__test__.jsonc b/tests/specs/run/tsx_imports/__test__.jsonc
new file mode 100644
index 0000000000..2026804add
--- /dev/null
+++ b/tests/specs/run/tsx_imports/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload --check tsx_imports/tsx_imports.ts",
+  "output": "tsx_imports/tsx_imports.ts.out"
+}
diff --git a/tests/testdata/run/tsx_imports/Component.tsx b/tests/specs/run/tsx_imports/tsx_imports/Component.tsx
similarity index 100%
rename from tests/testdata/run/tsx_imports/Component.tsx
rename to tests/specs/run/tsx_imports/tsx_imports/Component.tsx
diff --git a/tests/testdata/run/tsx_imports/tsx_imports.ts b/tests/specs/run/tsx_imports/tsx_imports/tsx_imports.ts
similarity index 100%
rename from tests/testdata/run/tsx_imports/tsx_imports.ts
rename to tests/specs/run/tsx_imports/tsx_imports/tsx_imports.ts
diff --git a/tests/testdata/run/tsx_imports/tsx_imports.ts.out b/tests/specs/run/tsx_imports/tsx_imports/tsx_imports.ts.out
similarity index 100%
rename from tests/testdata/run/tsx_imports/tsx_imports.ts.out
rename to tests/specs/run/tsx_imports/tsx_imports/tsx_imports.ts.out
diff --git a/tests/specs/run/type_definitions/__test__.jsonc b/tests/specs/run/type_definitions/__test__.jsonc
new file mode 100644
index 0000000000..5030612a51
--- /dev/null
+++ b/tests/specs/run/type_definitions/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload type_definitions.ts",
+  "output": "type_definitions.ts.out"
+}
diff --git a/tests/testdata/run/type_definitions.ts b/tests/specs/run/type_definitions/type_definitions.ts
similarity index 56%
rename from tests/testdata/run/type_definitions.ts
rename to tests/specs/run/type_definitions/type_definitions.ts
index 5948427219..0297c7e3d5 100644
--- a/tests/testdata/run/type_definitions.ts
+++ b/tests/specs/run/type_definitions/type_definitions.ts
@@ -1,11 +1,11 @@
 // deno-lint-ignore-file
 
 // @deno-types="../type_definitions/foo.d.ts"
-import { foo } from "../type_definitions/foo.js";
+import { foo } from "./type_definitions/foo.js";
 // @deno-types="../type_definitions/fizz.d.ts"
-import "../type_definitions/fizz.js";
+import "./type_definitions/fizz.js";
 
-import * as qat from "../type_definitions/qat.ts";
+import * as qat from "./type_definitions/qat.ts";
 
 console.log(foo);
 console.log(fizz);
diff --git a/tests/testdata/run/type_definitions.ts.out b/tests/specs/run/type_definitions/type_definitions.ts.out
similarity index 100%
rename from tests/testdata/run/type_definitions.ts.out
rename to tests/specs/run/type_definitions/type_definitions.ts.out
diff --git a/tests/specs/run/type_definitions/type_definitions/bar.d.ts b/tests/specs/run/type_definitions/type_definitions/bar.d.ts
new file mode 100644
index 0000000000..d43335dbb5
--- /dev/null
+++ b/tests/specs/run/type_definitions/type_definitions/bar.d.ts
@@ -0,0 +1,7 @@
+/// <reference types="baz" />
+
+declare namespace bar {
+  export class Bar {
+    baz: string;
+  }
+}
diff --git a/tests/specs/run/type_definitions/type_definitions/bar.js b/tests/specs/run/type_definitions/type_definitions/bar.js
new file mode 100644
index 0000000000..e9c2e5193c
--- /dev/null
+++ b/tests/specs/run/type_definitions/type_definitions/bar.js
@@ -0,0 +1,5 @@
+export class Bar {
+  constructor() {
+    this.baz = "baz";
+  }
+}
diff --git a/tests/specs/run/type_definitions/type_definitions/fizz.d.ts b/tests/specs/run/type_definitions/type_definitions/fizz.d.ts
new file mode 100644
index 0000000000..34eb41b960
--- /dev/null
+++ b/tests/specs/run/type_definitions/type_definitions/fizz.d.ts
@@ -0,0 +1,2 @@
+/** A global value. */
+declare const fizz: string;
diff --git a/tests/specs/run/type_definitions/type_definitions/fizz.js b/tests/specs/run/type_definitions/type_definitions/fizz.js
new file mode 100644
index 0000000000..852162c940
--- /dev/null
+++ b/tests/specs/run/type_definitions/type_definitions/fizz.js
@@ -0,0 +1 @@
+globalThis.fizz = "fizz";
diff --git a/tests/specs/run/type_definitions/type_definitions/foo.d.ts b/tests/specs/run/type_definitions/type_definitions/foo.d.ts
new file mode 100644
index 0000000000..ce39201e1b
--- /dev/null
+++ b/tests/specs/run/type_definitions/type_definitions/foo.d.ts
@@ -0,0 +1,2 @@
+/** An exported value. */
+export const foo: string;
diff --git a/tests/specs/run/type_definitions/type_definitions/foo.js b/tests/specs/run/type_definitions/type_definitions/foo.js
new file mode 100644
index 0000000000..61d366eb25
--- /dev/null
+++ b/tests/specs/run/type_definitions/type_definitions/foo.js
@@ -0,0 +1 @@
+export const foo = "foo";
diff --git a/tests/specs/run/type_definitions/type_definitions/qat.ts b/tests/specs/run/type_definitions/type_definitions/qat.ts
new file mode 100644
index 0000000000..6196c9d387
--- /dev/null
+++ b/tests/specs/run/type_definitions/type_definitions/qat.ts
@@ -0,0 +1 @@
+export const qat = "qat";
diff --git a/tests/specs/run/type_definitions_for_export/__test__.jsonc b/tests/specs/run/type_definitions_for_export/__test__.jsonc
new file mode 100644
index 0000000000..cf32bc9609
--- /dev/null
+++ b/tests/specs/run/type_definitions_for_export/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --reload --check type_definitions_for_export.ts",
+  "output": "type_definitions_for_export.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/type_definitions_for_export/export_type_def.ts b/tests/specs/run/type_definitions_for_export/export_type_def.ts
new file mode 100644
index 0000000000..e33b70a644
--- /dev/null
+++ b/tests/specs/run/type_definitions_for_export/export_type_def.ts
@@ -0,0 +1,2 @@
+// @deno-types="./type_definitions/foo.d.ts"
+export { foo } from "./type_definitions/foo.js";
diff --git a/tests/specs/run/type_definitions_for_export/type_definitions/bar.d.ts b/tests/specs/run/type_definitions_for_export/type_definitions/bar.d.ts
new file mode 100644
index 0000000000..d43335dbb5
--- /dev/null
+++ b/tests/specs/run/type_definitions_for_export/type_definitions/bar.d.ts
@@ -0,0 +1,7 @@
+/// <reference types="baz" />
+
+declare namespace bar {
+  export class Bar {
+    baz: string;
+  }
+}
diff --git a/tests/specs/run/type_definitions_for_export/type_definitions/bar.js b/tests/specs/run/type_definitions_for_export/type_definitions/bar.js
new file mode 100644
index 0000000000..e9c2e5193c
--- /dev/null
+++ b/tests/specs/run/type_definitions_for_export/type_definitions/bar.js
@@ -0,0 +1,5 @@
+export class Bar {
+  constructor() {
+    this.baz = "baz";
+  }
+}
diff --git a/tests/specs/run/type_definitions_for_export/type_definitions/fizz.d.ts b/tests/specs/run/type_definitions_for_export/type_definitions/fizz.d.ts
new file mode 100644
index 0000000000..34eb41b960
--- /dev/null
+++ b/tests/specs/run/type_definitions_for_export/type_definitions/fizz.d.ts
@@ -0,0 +1,2 @@
+/** A global value. */
+declare const fizz: string;
diff --git a/tests/specs/run/type_definitions_for_export/type_definitions/fizz.js b/tests/specs/run/type_definitions_for_export/type_definitions/fizz.js
new file mode 100644
index 0000000000..852162c940
--- /dev/null
+++ b/tests/specs/run/type_definitions_for_export/type_definitions/fizz.js
@@ -0,0 +1 @@
+globalThis.fizz = "fizz";
diff --git a/tests/specs/run/type_definitions_for_export/type_definitions/foo.d.ts b/tests/specs/run/type_definitions_for_export/type_definitions/foo.d.ts
new file mode 100644
index 0000000000..ce39201e1b
--- /dev/null
+++ b/tests/specs/run/type_definitions_for_export/type_definitions/foo.d.ts
@@ -0,0 +1,2 @@
+/** An exported value. */
+export const foo: string;
diff --git a/tests/specs/run/type_definitions_for_export/type_definitions/foo.js b/tests/specs/run/type_definitions_for_export/type_definitions/foo.js
new file mode 100644
index 0000000000..61d366eb25
--- /dev/null
+++ b/tests/specs/run/type_definitions_for_export/type_definitions/foo.js
@@ -0,0 +1 @@
+export const foo = "foo";
diff --git a/tests/specs/run/type_definitions_for_export/type_definitions/qat.ts b/tests/specs/run/type_definitions_for_export/type_definitions/qat.ts
new file mode 100644
index 0000000000..6196c9d387
--- /dev/null
+++ b/tests/specs/run/type_definitions_for_export/type_definitions/qat.ts
@@ -0,0 +1 @@
+export const qat = "qat";
diff --git a/tests/testdata/run/type_definitions_for_export.ts b/tests/specs/run/type_definitions_for_export/type_definitions_for_export.ts
similarity index 100%
rename from tests/testdata/run/type_definitions_for_export.ts
rename to tests/specs/run/type_definitions_for_export/type_definitions_for_export.ts
diff --git a/tests/testdata/run/type_definitions_for_export.ts.out b/tests/specs/run/type_definitions_for_export/type_definitions_for_export.ts.out
similarity index 100%
rename from tests/testdata/run/type_definitions_for_export.ts.out
rename to tests/specs/run/type_definitions_for_export/type_definitions_for_export.ts.out
diff --git a/tests/specs/run/type_directives_01/__test__.jsonc b/tests/specs/run/type_directives_01/__test__.jsonc
new file mode 100644
index 0000000000..08826b776e
--- /dev/null
+++ b/tests/specs/run/type_directives_01/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --reload --check=all -L debug type_directives_01.ts",
+  "output": "type_directives_01.ts.out"
+}
diff --git a/tests/testdata/run/type_directives_01.ts b/tests/specs/run/type_directives_01/type_directives_01.ts
similarity index 100%
rename from tests/testdata/run/type_directives_01.ts
rename to tests/specs/run/type_directives_01/type_directives_01.ts
diff --git a/tests/testdata/run/type_directives_01.ts.out b/tests/specs/run/type_directives_01/type_directives_01.ts.out
similarity index 100%
rename from tests/testdata/run/type_directives_01.ts.out
rename to tests/specs/run/type_directives_01/type_directives_01.ts.out
diff --git a/tests/specs/run/type_directives_02/__test__.jsonc b/tests/specs/run/type_directives_02/__test__.jsonc
new file mode 100644
index 0000000000..e731e393e1
--- /dev/null
+++ b/tests/specs/run/type_directives_02/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --reload --check=all -L debug type_directives_02.ts",
+  "output": "type_directives_02.ts.out"
+}
diff --git a/tests/specs/run/type_directives_02/type_directives_02.ts b/tests/specs/run/type_directives_02/type_directives_02.ts
new file mode 100644
index 0000000000..f829c0cec3
--- /dev/null
+++ b/tests/specs/run/type_directives_02/type_directives_02.ts
@@ -0,0 +1,3 @@
+import * as foo from "./type_reference.js";
+
+console.log(foo.foo);
diff --git a/tests/specs/run/type_directives_02/type_directives_02.ts.out b/tests/specs/run/type_directives_02/type_directives_02.ts.out
new file mode 100644
index 0000000000..d9bd381504
--- /dev/null
+++ b/tests/specs/run/type_directives_02/type_directives_02.ts.out
@@ -0,0 +1,3 @@
+[WILDCARD]
+DEBUG TS - host.getSourceFile("file:///[WILDCARD]/type_reference.d.ts", Latest)
+[WILDCARD]
\ No newline at end of file
diff --git a/tests/specs/run/type_directives_02/type_reference.d.ts b/tests/specs/run/type_directives_02/type_reference.d.ts
new file mode 100644
index 0000000000..f9b8de5ede
--- /dev/null
+++ b/tests/specs/run/type_directives_02/type_reference.d.ts
@@ -0,0 +1 @@
+export const foo: "foo";
diff --git a/tests/specs/run/type_directives_02/type_reference.js b/tests/specs/run/type_directives_02/type_reference.js
new file mode 100644
index 0000000000..917d891980
--- /dev/null
+++ b/tests/specs/run/type_directives_02/type_reference.js
@@ -0,0 +1,3 @@
+/// <reference types="./type_reference.d.ts" />
+
+export const foo = "foo";
diff --git a/tests/specs/run/type_headers_deno_types/__test__.jsonc b/tests/specs/run/type_headers_deno_types/__test__.jsonc
new file mode 100644
index 0000000000..1a95fa2d45
--- /dev/null
+++ b/tests/specs/run/type_headers_deno_types/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-import --reload --check type_headers_deno_types.ts",
+  "output": "type_headers_deno_types.ts.out"
+}
diff --git a/tests/testdata/run/type_headers_deno_types.ts b/tests/specs/run/type_headers_deno_types/type_headers_deno_types.ts
similarity index 100%
rename from tests/testdata/run/type_headers_deno_types.ts
rename to tests/specs/run/type_headers_deno_types/type_headers_deno_types.ts
diff --git a/tests/testdata/run/type_headers_deno_types.ts.out b/tests/specs/run/type_headers_deno_types/type_headers_deno_types.ts.out
similarity index 100%
rename from tests/testdata/run/type_headers_deno_types.ts.out
rename to tests/specs/run/type_headers_deno_types/type_headers_deno_types.ts.out
diff --git a/tests/specs/run/unbuffered_stderr/__test__.jsonc b/tests/specs/run/unbuffered_stderr/__test__.jsonc
new file mode 100644
index 0000000000..4b8a091f24
--- /dev/null
+++ b/tests/specs/run/unbuffered_stderr/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload unbuffered_stderr.ts",
+  "output": "unbuffered_stderr.ts.out"
+}
diff --git a/tests/testdata/run/unbuffered_stderr.ts b/tests/specs/run/unbuffered_stderr/unbuffered_stderr.ts
similarity index 100%
rename from tests/testdata/run/unbuffered_stderr.ts
rename to tests/specs/run/unbuffered_stderr/unbuffered_stderr.ts
diff --git a/tests/testdata/run/unbuffered_stderr.ts.out b/tests/specs/run/unbuffered_stderr/unbuffered_stderr.ts.out
similarity index 100%
rename from tests/testdata/run/unbuffered_stderr.ts.out
rename to tests/specs/run/unbuffered_stderr/unbuffered_stderr.ts.out
diff --git a/tests/specs/run/unbuffered_stdout/__test__.jsonc b/tests/specs/run/unbuffered_stdout/__test__.jsonc
new file mode 100644
index 0000000000..4225e9d0a2
--- /dev/null
+++ b/tests/specs/run/unbuffered_stdout/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload unbuffered_stdout.ts",
+  "output": "unbuffered_stdout.ts.out"
+}
diff --git a/tests/testdata/run/unbuffered_stdout.ts b/tests/specs/run/unbuffered_stdout/unbuffered_stdout.ts
similarity index 100%
rename from tests/testdata/run/unbuffered_stdout.ts
rename to tests/specs/run/unbuffered_stdout/unbuffered_stdout.ts
diff --git a/tests/testdata/run/unbuffered_stdout.ts.out b/tests/specs/run/unbuffered_stdout/unbuffered_stdout.ts.out
similarity index 100%
rename from tests/testdata/run/unbuffered_stdout.ts.out
rename to tests/specs/run/unbuffered_stdout/unbuffered_stdout.ts.out
diff --git a/tests/specs/run/unhandled_rejection/__test__.jsonc b/tests/specs/run/unhandled_rejection/__test__.jsonc
new file mode 100644
index 0000000000..3a22292062
--- /dev/null
+++ b/tests/specs/run/unhandled_rejection/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --check unhandled_rejection.ts",
+  "output": "unhandled_rejection.ts.out"
+}
diff --git a/tests/testdata/run/unhandled_rejection.ts b/tests/specs/run/unhandled_rejection/unhandled_rejection.ts
similarity index 100%
rename from tests/testdata/run/unhandled_rejection.ts
rename to tests/specs/run/unhandled_rejection/unhandled_rejection.ts
diff --git a/tests/specs/run/unhandled_rejection/unhandled_rejection.ts.out b/tests/specs/run/unhandled_rejection/unhandled_rejection.ts.out
new file mode 100644
index 0000000000..fc5a3915f6
--- /dev/null
+++ b/tests/specs/run/unhandled_rejection/unhandled_rejection.ts.out
@@ -0,0 +1,9 @@
+[WILDCARD]
+unhandled rejection at: Promise {
+  <rejected> Error: bar not available
+    at new Foo (file:///[WILDCARD]/unhandled_rejection.ts:8:20)
+    at file:///[WILDCARD]/unhandled_rejection.ts:12:1
+} reason: Error: bar not available
+    at new Foo (file:///[WILDCARD]/unhandled_rejection.ts:8:20)
+    at file:///[WILDCARD]/unhandled_rejection.ts:12:1
+unhandled rejection at: Promise { <rejected> undefined } reason: undefined
diff --git a/tests/specs/run/unhandled_rejection_dynamic_import/__test__.jsonc b/tests/specs/run/unhandled_rejection_dynamic_import/__test__.jsonc
new file mode 100644
index 0000000000..6ca0d093b9
--- /dev/null
+++ b/tests/specs/run/unhandled_rejection_dynamic_import/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --allow-read unhandled_rejection_dynamic_import/main.ts",
+  "output": "unhandled_rejection_dynamic_import/main.ts.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/unhandled_rejection_dynamic_import/import.ts b/tests/specs/run/unhandled_rejection_dynamic_import/unhandled_rejection_dynamic_import/import.ts
similarity index 100%
rename from tests/testdata/run/unhandled_rejection_dynamic_import/import.ts
rename to tests/specs/run/unhandled_rejection_dynamic_import/unhandled_rejection_dynamic_import/import.ts
diff --git a/tests/testdata/run/unhandled_rejection_dynamic_import/main.ts b/tests/specs/run/unhandled_rejection_dynamic_import/unhandled_rejection_dynamic_import/main.ts
similarity index 100%
rename from tests/testdata/run/unhandled_rejection_dynamic_import/main.ts
rename to tests/specs/run/unhandled_rejection_dynamic_import/unhandled_rejection_dynamic_import/main.ts
diff --git a/tests/testdata/run/unhandled_rejection_dynamic_import/main.ts.out b/tests/specs/run/unhandled_rejection_dynamic_import/unhandled_rejection_dynamic_import/main.ts.out
similarity index 100%
rename from tests/testdata/run/unhandled_rejection_dynamic_import/main.ts.out
rename to tests/specs/run/unhandled_rejection_dynamic_import/unhandled_rejection_dynamic_import/main.ts.out
diff --git a/tests/specs/run/unhandled_rejection_dynamic_import2/__test__.jsonc b/tests/specs/run/unhandled_rejection_dynamic_import2/__test__.jsonc
new file mode 100644
index 0000000000..a4e588f463
--- /dev/null
+++ b/tests/specs/run/unhandled_rejection_dynamic_import2/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read unhandled_rejection_dynamic_import2/main.ts",
+  "output": "unhandled_rejection_dynamic_import2/main.ts.out"
+}
diff --git a/tests/testdata/run/unhandled_rejection_dynamic_import2/import.ts b/tests/specs/run/unhandled_rejection_dynamic_import2/unhandled_rejection_dynamic_import2/import.ts
similarity index 100%
rename from tests/testdata/run/unhandled_rejection_dynamic_import2/import.ts
rename to tests/specs/run/unhandled_rejection_dynamic_import2/unhandled_rejection_dynamic_import2/import.ts
diff --git a/tests/testdata/run/unhandled_rejection_dynamic_import2/main.ts b/tests/specs/run/unhandled_rejection_dynamic_import2/unhandled_rejection_dynamic_import2/main.ts
similarity index 100%
rename from tests/testdata/run/unhandled_rejection_dynamic_import2/main.ts
rename to tests/specs/run/unhandled_rejection_dynamic_import2/unhandled_rejection_dynamic_import2/main.ts
diff --git a/tests/testdata/run/unhandled_rejection_dynamic_import2/main.ts.out b/tests/specs/run/unhandled_rejection_dynamic_import2/unhandled_rejection_dynamic_import2/main.ts.out
similarity index 100%
rename from tests/testdata/run/unhandled_rejection_dynamic_import2/main.ts.out
rename to tests/specs/run/unhandled_rejection_dynamic_import2/unhandled_rejection_dynamic_import2/main.ts.out
diff --git a/tests/specs/run/unhandled_rejection_sync_error/__test__.jsonc b/tests/specs/run/unhandled_rejection_sync_error/__test__.jsonc
new file mode 100644
index 0000000000..3f09f9c369
--- /dev/null
+++ b/tests/specs/run/unhandled_rejection_sync_error/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --check unhandled_rejection_sync_error.ts",
+  "output": "unhandled_rejection_sync_error.ts.out"
+}
diff --git a/tests/testdata/run/unhandled_rejection_sync_error.ts b/tests/specs/run/unhandled_rejection_sync_error/unhandled_rejection_sync_error.ts
similarity index 100%
rename from tests/testdata/run/unhandled_rejection_sync_error.ts
rename to tests/specs/run/unhandled_rejection_sync_error/unhandled_rejection_sync_error.ts
diff --git a/tests/specs/run/unhandled_rejection_sync_error/unhandled_rejection_sync_error.ts.out b/tests/specs/run/unhandled_rejection_sync_error/unhandled_rejection_sync_error.ts.out
new file mode 100644
index 0000000000..0c1115ef24
--- /dev/null
+++ b/tests/specs/run/unhandled_rejection_sync_error/unhandled_rejection_sync_error.ts.out
@@ -0,0 +1,6 @@
+[WILDCARD]
+unhandled rejection at: Promise {
+  <rejected> Error: boom!
+    at file:///[WILDCARD]unhandled_rejection_sync_error.ts:6:7
+} reason: Error: boom!
+    at file:///[WILDCARD]unhandled_rejection_sync_error.ts:6:7
diff --git a/tests/specs/run/unsafe_proto/__test__.jsonc b/tests/specs/run/unsafe_proto/__test__.jsonc
new file mode 100644
index 0000000000..d1c608b515
--- /dev/null
+++ b/tests/specs/run/unsafe_proto/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run -A unsafe_proto/main.js",
+  "output": "unsafe_proto/main.out",
+  "exitCode": 0
+}
diff --git a/tests/testdata/run/unsafe_proto/main.js b/tests/specs/run/unsafe_proto/unsafe_proto/main.js
similarity index 100%
rename from tests/testdata/run/unsafe_proto/main.js
rename to tests/specs/run/unsafe_proto/unsafe_proto/main.js
diff --git a/tests/testdata/run/unsafe_proto/main.out b/tests/specs/run/unsafe_proto/unsafe_proto/main.out
similarity index 100%
rename from tests/testdata/run/unsafe_proto/main.out
rename to tests/specs/run/unsafe_proto/unsafe_proto/main.out
diff --git a/tests/testdata/run/unsafe_proto/main_with_unsafe_proto_flag.out b/tests/specs/run/unsafe_proto/unsafe_proto/main_with_unsafe_proto_flag.out
similarity index 100%
rename from tests/testdata/run/unsafe_proto/main_with_unsafe_proto_flag.out
rename to tests/specs/run/unsafe_proto/unsafe_proto/main_with_unsafe_proto_flag.out
diff --git a/tests/testdata/run/unsafe_proto/worker.js b/tests/specs/run/unsafe_proto/unsafe_proto/worker.js
similarity index 100%
rename from tests/testdata/run/unsafe_proto/worker.js
rename to tests/specs/run/unsafe_proto/unsafe_proto/worker.js
diff --git a/tests/specs/run/unsafe_proto_flag/__test__.jsonc b/tests/specs/run/unsafe_proto_flag/__test__.jsonc
new file mode 100644
index 0000000000..8bd2b56ffc
--- /dev/null
+++ b/tests/specs/run/unsafe_proto_flag/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run -A --unstable-unsafe-proto unsafe_proto/main.js",
+  "output": "unsafe_proto/main_with_unsafe_proto_flag.out",
+  "exitCode": 0
+}
diff --git a/tests/specs/run/unsafe_proto_flag/unsafe_proto/main.js b/tests/specs/run/unsafe_proto_flag/unsafe_proto/main.js
new file mode 100644
index 0000000000..eb95c55a03
--- /dev/null
+++ b/tests/specs/run/unsafe_proto_flag/unsafe_proto/main.js
@@ -0,0 +1,5 @@
+console.log(Object.hasOwn(Object.prototype, "__proto__"));
+
+new Worker(import.meta.resolve("./worker.js"), {
+  type: "module",
+});
diff --git a/tests/specs/run/unsafe_proto_flag/unsafe_proto/main.out b/tests/specs/run/unsafe_proto_flag/unsafe_proto/main.out
new file mode 100644
index 0000000000..4b095fd0ff
--- /dev/null
+++ b/tests/specs/run/unsafe_proto_flag/unsafe_proto/main.out
@@ -0,0 +1,2 @@
+false
+false
diff --git a/tests/specs/run/unsafe_proto_flag/unsafe_proto/main_with_unsafe_proto_flag.out b/tests/specs/run/unsafe_proto_flag/unsafe_proto/main_with_unsafe_proto_flag.out
new file mode 100644
index 0000000000..bb101b641b
--- /dev/null
+++ b/tests/specs/run/unsafe_proto_flag/unsafe_proto/main_with_unsafe_proto_flag.out
@@ -0,0 +1,2 @@
+true
+true
diff --git a/tests/specs/run/unsafe_proto_flag/unsafe_proto/worker.js b/tests/specs/run/unsafe_proto_flag/unsafe_proto/worker.js
new file mode 100644
index 0000000000..b22bc87139
--- /dev/null
+++ b/tests/specs/run/unsafe_proto_flag/unsafe_proto/worker.js
@@ -0,0 +1,2 @@
+console.log(Object.hasOwn(Object.prototype, "__proto__"));
+close();
diff --git a/tests/specs/run/unstable/__test__.jsonc b/tests/specs/run/unstable/__test__.jsonc
index 3ddcdb583c..bceb2ac12b 100644
--- a/tests/specs/run/unstable/__test__.jsonc
+++ b/tests/specs/run/unstable/__test__.jsonc
@@ -20,6 +20,11 @@
       "exitCode": 1,
       "output": "kv.out"
     },
+    "node_globals": {
+      "args": "run --unstable-node-globals node_globals.ts",
+      "exitCode": 0,
+      "output": "node_globals.out"
+    },
     "temporal": {
       "args": "run temporal.ts",
       "exitCode": 1,
diff --git a/tests/specs/run/unstable/node_globals.out b/tests/specs/run/unstable/node_globals.out
new file mode 100644
index 0000000000..77045c7cbd
--- /dev/null
+++ b/tests/specs/run/unstable/node_globals.out
@@ -0,0 +1,4 @@
+global: true
+Buffer: true
+setImmediate: true
+clearImmediate: true
diff --git a/tests/specs/run/unstable/node_globals.ts b/tests/specs/run/unstable/node_globals.ts
new file mode 100644
index 0000000000..706b7eb654
--- /dev/null
+++ b/tests/specs/run/unstable/node_globals.ts
@@ -0,0 +1,7 @@
+import * as nodeBuffer from "node:buffer";
+import * as nodeTimers from "node:timers";
+
+console.log(`global: ${globalThis === global}`);
+console.log(`Buffer: ${Buffer === nodeBuffer.default}`);
+console.log(`setImmediate: ${setImmediate === nodeTimers.setImmediate}`);
+console.log(`clearImmediate: ${clearImmediate === nodeTimers.clearImmediate}`);
diff --git a/tests/specs/run/unstable_broadcast_channel_disabled/__test__.jsonc b/tests/specs/run/unstable_broadcast_channel_disabled/__test__.jsonc
new file mode 100644
index 0000000000..fa12c9f91d
--- /dev/null
+++ b/tests/specs/run/unstable_broadcast_channel_disabled/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-read unstable_broadcast_channel.js",
+  "output": "unstable_broadcast_channel.disabled.out"
+}
diff --git a/tests/testdata/run/unstable_broadcast_channel.disabled.out b/tests/specs/run/unstable_broadcast_channel_disabled/unstable_broadcast_channel.disabled.out
similarity index 100%
rename from tests/testdata/run/unstable_broadcast_channel.disabled.out
rename to tests/specs/run/unstable_broadcast_channel_disabled/unstable_broadcast_channel.disabled.out
diff --git a/tests/testdata/run/unstable_broadcast_channel.js b/tests/specs/run/unstable_broadcast_channel_disabled/unstable_broadcast_channel.js
similarity index 100%
rename from tests/testdata/run/unstable_broadcast_channel.js
rename to tests/specs/run/unstable_broadcast_channel_disabled/unstable_broadcast_channel.js
diff --git a/tests/specs/run/unstable_broadcast_channel_enabled/__test__.jsonc b/tests/specs/run/unstable_broadcast_channel_enabled/__test__.jsonc
new file mode 100644
index 0000000000..f93c7785a4
--- /dev/null
+++ b/tests/specs/run/unstable_broadcast_channel_enabled/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-read --unstable-broadcast-channel unstable_broadcast_channel.js",
+  "output": "unstable_broadcast_channel.enabled.out"
+}
diff --git a/tests/testdata/run/unstable_broadcast_channel.enabled.out b/tests/specs/run/unstable_broadcast_channel_enabled/unstable_broadcast_channel.enabled.out
similarity index 100%
rename from tests/testdata/run/unstable_broadcast_channel.enabled.out
rename to tests/specs/run/unstable_broadcast_channel_enabled/unstable_broadcast_channel.enabled.out
diff --git a/tests/specs/run/unstable_broadcast_channel_enabled/unstable_broadcast_channel.js b/tests/specs/run/unstable_broadcast_channel_enabled/unstable_broadcast_channel.js
new file mode 100644
index 0000000000..b8576aa22f
--- /dev/null
+++ b/tests/specs/run/unstable_broadcast_channel_enabled/unstable_broadcast_channel.js
@@ -0,0 +1,10 @@
+const scope = import.meta.url.slice(-7) === "#worker" ? "worker" : "main";
+
+console.log(scope, globalThis.BroadcastChannel);
+
+if (scope === "worker") {
+  postMessage("done");
+} else {
+  const worker = new Worker(`${import.meta.url}#worker`, { type: "module" });
+  worker.onmessage = () => Deno.exit(0);
+}
diff --git a/tests/specs/run/unstable_cron_disabled/__test__.jsonc b/tests/specs/run/unstable_cron_disabled/__test__.jsonc
new file mode 100644
index 0000000000..be89db40b5
--- /dev/null
+++ b/tests/specs/run/unstable_cron_disabled/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-read unstable_cron.js",
+  "output": "unstable_cron.disabled.out"
+}
diff --git a/tests/testdata/run/unstable_cron.disabled.out b/tests/specs/run/unstable_cron_disabled/unstable_cron.disabled.out
similarity index 100%
rename from tests/testdata/run/unstable_cron.disabled.out
rename to tests/specs/run/unstable_cron_disabled/unstable_cron.disabled.out
diff --git a/tests/testdata/run/unstable_cron.js b/tests/specs/run/unstable_cron_disabled/unstable_cron.js
similarity index 100%
rename from tests/testdata/run/unstable_cron.js
rename to tests/specs/run/unstable_cron_disabled/unstable_cron.js
diff --git a/tests/specs/run/unstable_cron_enabled/__test__.jsonc b/tests/specs/run/unstable_cron_enabled/__test__.jsonc
new file mode 100644
index 0000000000..07a37e3fef
--- /dev/null
+++ b/tests/specs/run/unstable_cron_enabled/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-read --unstable-cron unstable_cron.js",
+  "output": "unstable_cron.enabled.out"
+}
diff --git a/tests/testdata/run/unstable_cron.enabled.out b/tests/specs/run/unstable_cron_enabled/unstable_cron.enabled.out
similarity index 100%
rename from tests/testdata/run/unstable_cron.enabled.out
rename to tests/specs/run/unstable_cron_enabled/unstable_cron.enabled.out
diff --git a/tests/specs/run/unstable_cron_enabled/unstable_cron.js b/tests/specs/run/unstable_cron_enabled/unstable_cron.js
new file mode 100644
index 0000000000..3114f6e555
--- /dev/null
+++ b/tests/specs/run/unstable_cron_enabled/unstable_cron.js
@@ -0,0 +1,10 @@
+const scope = import.meta.url.slice(-7) === "#worker" ? "worker" : "main";
+
+console.log(scope, Deno.cron);
+
+if (scope === "worker") {
+  postMessage("done");
+} else {
+  const worker = new Worker(`${import.meta.url}#worker`, { type: "module" });
+  worker.onmessage = () => Deno.exit(0);
+}
diff --git a/tests/specs/run/unstable_kv_disabled/__test__.jsonc b/tests/specs/run/unstable_kv_disabled/__test__.jsonc
new file mode 100644
index 0000000000..6521c180d8
--- /dev/null
+++ b/tests/specs/run/unstable_kv_disabled/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-read unstable_kv.js",
+  "output": "unstable_kv.disabled.out"
+}
diff --git a/tests/testdata/run/unstable_kv.disabled.out b/tests/specs/run/unstable_kv_disabled/unstable_kv.disabled.out
similarity index 100%
rename from tests/testdata/run/unstable_kv.disabled.out
rename to tests/specs/run/unstable_kv_disabled/unstable_kv.disabled.out
diff --git a/tests/testdata/run/unstable_kv.js b/tests/specs/run/unstable_kv_disabled/unstable_kv.js
similarity index 100%
rename from tests/testdata/run/unstable_kv.js
rename to tests/specs/run/unstable_kv_disabled/unstable_kv.js
diff --git a/tests/specs/run/unstable_kv_enabled/__test__.jsonc b/tests/specs/run/unstable_kv_enabled/__test__.jsonc
new file mode 100644
index 0000000000..6e9fea1000
--- /dev/null
+++ b/tests/specs/run/unstable_kv_enabled/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-read --unstable-kv unstable_kv.js",
+  "output": "unstable_kv.enabled.out"
+}
diff --git a/tests/testdata/run/unstable_kv.enabled.out b/tests/specs/run/unstable_kv_enabled/unstable_kv.enabled.out
similarity index 100%
rename from tests/testdata/run/unstable_kv.enabled.out
rename to tests/specs/run/unstable_kv_enabled/unstable_kv.enabled.out
diff --git a/tests/specs/run/unstable_kv_enabled/unstable_kv.js b/tests/specs/run/unstable_kv_enabled/unstable_kv.js
new file mode 100644
index 0000000000..17c0e05aa5
--- /dev/null
+++ b/tests/specs/run/unstable_kv_enabled/unstable_kv.js
@@ -0,0 +1,14 @@
+const scope = import.meta.url.slice(-7) === "#worker" ? "worker" : "main";
+
+console.log(scope, Deno.AtomicOperation);
+console.log(scope, Deno.Kv);
+console.log(scope, Deno.KvListIterator);
+console.log(scope, Deno.KvU64);
+console.log(scope, Deno.openKv);
+
+if (scope === "worker") {
+  postMessage("done");
+} else {
+  const worker = new Worker(`${import.meta.url}#worker`, { type: "module" });
+  worker.onmessage = () => Deno.exit(0);
+}
diff --git a/tests/specs/run/unstable_net_disabled/__test__.jsonc b/tests/specs/run/unstable_net_disabled/__test__.jsonc
new file mode 100644
index 0000000000..6bccb2ef6c
--- /dev/null
+++ b/tests/specs/run/unstable_net_disabled/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-read unstable_net.js",
+  "output": "unstable_net.disabled.out"
+}
diff --git a/tests/testdata/run/unstable_net.disabled.out b/tests/specs/run/unstable_net_disabled/unstable_net.disabled.out
similarity index 100%
rename from tests/testdata/run/unstable_net.disabled.out
rename to tests/specs/run/unstable_net_disabled/unstable_net.disabled.out
diff --git a/tests/testdata/run/unstable_net.js b/tests/specs/run/unstable_net_disabled/unstable_net.js
similarity index 100%
rename from tests/testdata/run/unstable_net.js
rename to tests/specs/run/unstable_net_disabled/unstable_net.js
diff --git a/tests/specs/run/unstable_net_enabled/__test__.jsonc b/tests/specs/run/unstable_net_enabled/__test__.jsonc
new file mode 100644
index 0000000000..8e9696f44a
--- /dev/null
+++ b/tests/specs/run/unstable_net_enabled/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-read --unstable-net unstable_net.js",
+  "output": "unstable_net.enabled.out"
+}
diff --git a/tests/testdata/run/unstable_net.enabled.out b/tests/specs/run/unstable_net_enabled/unstable_net.enabled.out
similarity index 100%
rename from tests/testdata/run/unstable_net.enabled.out
rename to tests/specs/run/unstable_net_enabled/unstable_net.enabled.out
diff --git a/tests/specs/run/unstable_net_enabled/unstable_net.js b/tests/specs/run/unstable_net_enabled/unstable_net.js
new file mode 100644
index 0000000000..4492b202b1
--- /dev/null
+++ b/tests/specs/run/unstable_net_enabled/unstable_net.js
@@ -0,0 +1,11 @@
+const scope = import.meta.url.slice(-7) === "#worker" ? "worker" : "main";
+
+console.log(scope, Deno.listenDatagram);
+console.log(scope, globalThis.WebSocketStream);
+
+if (scope === "worker") {
+  postMessage("done");
+} else {
+  const worker = new Worker(`${import.meta.url}#worker`, { type: "module" });
+  worker.onmessage = () => Deno.exit(0);
+}
diff --git a/tests/specs/run/unstable_worker/__test__.jsonc b/tests/specs/run/unstable_worker/__test__.jsonc
new file mode 100644
index 0000000000..7a6e9bfbe0
--- /dev/null
+++ b/tests/specs/run/unstable_worker/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --reload --quiet --allow-read unstable_worker.ts",
+  "output": "unstable_worker.ts.out"
+}
diff --git a/tests/testdata/run/unstable_worker.ts b/tests/specs/run/unstable_worker/unstable_worker.ts
similarity index 62%
rename from tests/testdata/run/unstable_worker.ts
rename to tests/specs/run/unstable_worker/unstable_worker.ts
index d111d2c7e3..b0554c5b21 100644
--- a/tests/testdata/run/unstable_worker.ts
+++ b/tests/specs/run/unstable_worker/unstable_worker.ts
@@ -1,5 +1,5 @@
 const w = new Worker(
-  import.meta.resolve("../workers/worker_unstable.ts"),
+  import.meta.resolve("./worker_unstable.ts"),
   { type: "module", name: "Unstable Worker" },
 );
 
diff --git a/tests/testdata/run/unstable_worker.ts.out b/tests/specs/run/unstable_worker/unstable_worker.ts.out
similarity index 100%
rename from tests/testdata/run/unstable_worker.ts.out
rename to tests/specs/run/unstable_worker/unstable_worker.ts.out
diff --git a/tests/specs/run/unstable_worker/worker_unstable.ts b/tests/specs/run/unstable_worker/worker_unstable.ts
new file mode 100644
index 0000000000..219f34e7b8
--- /dev/null
+++ b/tests/specs/run/unstable_worker/worker_unstable.ts
@@ -0,0 +1,5 @@
+console.log(Deno.permissions.query);
+console.log(Deno.consoleSize);
+self.onmessage = () => {
+  self.close();
+};
diff --git a/tests/specs/run/unstable_worker_options_disabled/__test__.jsonc b/tests/specs/run/unstable_worker_options_disabled/__test__.jsonc
new file mode 100644
index 0000000000..30087244ec
--- /dev/null
+++ b/tests/specs/run/unstable_worker_options_disabled/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --reload --allow-read unstable_worker_options.js",
+  "output": "unstable_worker_options.disabled.out",
+  "exitCode": 70
+}
diff --git a/tests/testdata/run/unstable_worker_options.disabled.out b/tests/specs/run/unstable_worker_options_disabled/unstable_worker_options.disabled.out
similarity index 100%
rename from tests/testdata/run/unstable_worker_options.disabled.out
rename to tests/specs/run/unstable_worker_options_disabled/unstable_worker_options.disabled.out
diff --git a/tests/testdata/run/unstable_worker_options.js b/tests/specs/run/unstable_worker_options_disabled/unstable_worker_options.js
similarity index 100%
rename from tests/testdata/run/unstable_worker_options.js
rename to tests/specs/run/unstable_worker_options_disabled/unstable_worker_options.js
diff --git a/tests/specs/run/unstable_worker_options_enabled/__test__.jsonc b/tests/specs/run/unstable_worker_options_enabled/__test__.jsonc
new file mode 100644
index 0000000000..1d397c5f24
--- /dev/null
+++ b/tests/specs/run/unstable_worker_options_enabled/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-read --unstable-worker-options unstable_worker_options.js",
+  "output": "unstable_worker_options.enabled.out"
+}
diff --git a/tests/testdata/run/unstable_worker_options.enabled.out b/tests/specs/run/unstable_worker_options_enabled/unstable_worker_options.enabled.out
similarity index 100%
rename from tests/testdata/run/unstable_worker_options.enabled.out
rename to tests/specs/run/unstable_worker_options_enabled/unstable_worker_options.enabled.out
diff --git a/tests/specs/run/unstable_worker_options_enabled/unstable_worker_options.js b/tests/specs/run/unstable_worker_options_enabled/unstable_worker_options.js
new file mode 100644
index 0000000000..213eb3ee67
--- /dev/null
+++ b/tests/specs/run/unstable_worker_options_enabled/unstable_worker_options.js
@@ -0,0 +1,19 @@
+const scope = import.meta.url.slice(-7) === "#worker" ? "worker" : "main";
+
+new Worker(`data:application/javascript;base64,${btoa(`postMessage("ok");`)}`, {
+  type: "module",
+  deno: {
+    permissions: {
+      read: true,
+    },
+  },
+}).onmessage = ({ data }) => {
+  console.log(scope, data);
+
+  if (scope === "main") {
+    const worker = new Worker(`${import.meta.url}#worker`, { type: "module" });
+    worker.onmessage = () => Deno.exit(0);
+  } else {
+    postMessage("done");
+  }
+};
diff --git a/tests/specs/run/unsupported_dynamic_import_scheme/__test__.jsonc b/tests/specs/run/unsupported_dynamic_import_scheme/__test__.jsonc
new file mode 100644
index 0000000000..7f71dcebae
--- /dev/null
+++ b/tests/specs/run/unsupported_dynamic_import_scheme/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "eval import('xxx:')",
+  "output": "unsupported_dynamic_import_scheme.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/unsupported_dynamic_import_scheme.out b/tests/specs/run/unsupported_dynamic_import_scheme/unsupported_dynamic_import_scheme.out
similarity index 100%
rename from tests/testdata/run/unsupported_dynamic_import_scheme.out
rename to tests/specs/run/unsupported_dynamic_import_scheme/unsupported_dynamic_import_scheme.out
diff --git a/tests/specs/run/v8_flags_env_run/__test__.jsonc b/tests/specs/run/v8_flags_env_run/__test__.jsonc
new file mode 100644
index 0000000000..39ea666b84
--- /dev/null
+++ b/tests/specs/run/v8_flags_env_run/__test__.jsonc
@@ -0,0 +1,7 @@
+{
+  "args": "run v8_flags.js",
+  "output": "v8_flags.js.out",
+  "envs": {
+    "DENO_V8_FLAGS": "--expose-gc"
+  }
+}
diff --git a/tests/testdata/run/v8_flags.js b/tests/specs/run/v8_flags_env_run/v8_flags.js
similarity index 100%
rename from tests/testdata/run/v8_flags.js
rename to tests/specs/run/v8_flags_env_run/v8_flags.js
diff --git a/tests/testdata/run/v8_flags.js.out b/tests/specs/run/v8_flags_env_run/v8_flags.js.out
similarity index 100%
rename from tests/testdata/run/v8_flags.js.out
rename to tests/specs/run/v8_flags_env_run/v8_flags.js.out
diff --git a/tests/specs/run/v8_flags_run/__test__.jsonc b/tests/specs/run/v8_flags_run/__test__.jsonc
new file mode 100644
index 0000000000..ff21fb8c5b
--- /dev/null
+++ b/tests/specs/run/v8_flags_run/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --v8-flags=--expose-gc v8_flags.js",
+  "output": "v8_flags.js.out"
+}
diff --git a/tests/specs/run/v8_flags_run/v8_flags.js b/tests/specs/run/v8_flags_run/v8_flags.js
new file mode 100644
index 0000000000..f7999c4afd
--- /dev/null
+++ b/tests/specs/run/v8_flags_run/v8_flags.js
@@ -0,0 +1 @@
+console.log(typeof gc);
diff --git a/tests/specs/run/v8_flags_run/v8_flags.js.out b/tests/specs/run/v8_flags_run/v8_flags.js.out
new file mode 100644
index 0000000000..e2dbde096f
--- /dev/null
+++ b/tests/specs/run/v8_flags_run/v8_flags.js.out
@@ -0,0 +1 @@
+function
diff --git a/tests/specs/run/v8_flags_unrecognized/__test__.jsonc b/tests/specs/run/v8_flags_unrecognized/__test__.jsonc
new file mode 100644
index 0000000000..93472d0d74
--- /dev/null
+++ b/tests/specs/run/v8_flags_unrecognized/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "repl --v8-flags=--foo,bar,--trace-gc,-baz",
+  "output": "v8_flags_unrecognized.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/v8_flags_unrecognized.out b/tests/specs/run/v8_flags_unrecognized/v8_flags_unrecognized.out
similarity index 100%
rename from tests/testdata/run/v8_flags_unrecognized.out
rename to tests/specs/run/v8_flags_unrecognized/v8_flags_unrecognized.out
diff --git a/tests/specs/run/v8_help/__test__.jsonc b/tests/specs/run/v8_help/__test__.jsonc
new file mode 100644
index 0000000000..90cbeb2748
--- /dev/null
+++ b/tests/specs/run/v8_help/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "repl --v8-flags=--help",
+  "output": "v8_help.out"
+}
diff --git a/tests/testdata/run/v8_help.out b/tests/specs/run/v8_help/v8_help.out
similarity index 100%
rename from tests/testdata/run/v8_help.out
rename to tests/specs/run/v8_help/v8_help.out
diff --git a/tests/specs/run/wasm/__test__.jsonc b/tests/specs/run/wasm/__test__.jsonc
new file mode 100644
index 0000000000..a3c6f58b2b
--- /dev/null
+++ b/tests/specs/run/wasm/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet wasm.ts",
+  "output": "wasm.ts.out"
+}
diff --git a/tests/testdata/run/wasm.ts b/tests/specs/run/wasm/wasm.ts
similarity index 100%
rename from tests/testdata/run/wasm.ts
rename to tests/specs/run/wasm/wasm.ts
diff --git a/tests/specs/run/wasm/wasm.ts.out b/tests/specs/run/wasm/wasm.ts.out
new file mode 100644
index 0000000000..d81cc0710e
--- /dev/null
+++ b/tests/specs/run/wasm/wasm.ts.out
@@ -0,0 +1 @@
+42
diff --git a/tests/specs/run/wasm_async/__test__.jsonc b/tests/specs/run/wasm_async/__test__.jsonc
new file mode 100644
index 0000000000..583da86e01
--- /dev/null
+++ b/tests/specs/run/wasm_async/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run wasm_async.js",
+  "output": "wasm_async.out"
+}
diff --git a/tests/testdata/run/wasm_async.js b/tests/specs/run/wasm_async/wasm_async.js
similarity index 100%
rename from tests/testdata/run/wasm_async.js
rename to tests/specs/run/wasm_async/wasm_async.js
diff --git a/tests/testdata/run/wasm_async.out b/tests/specs/run/wasm_async/wasm_async.out
similarity index 100%
rename from tests/testdata/run/wasm_async.out
rename to tests/specs/run/wasm_async/wasm_async.out
diff --git a/tests/specs/run/wasm_shared/__test__.jsonc b/tests/specs/run/wasm_shared/__test__.jsonc
new file mode 100644
index 0000000000..1b6ececa75
--- /dev/null
+++ b/tests/specs/run/wasm_shared/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet wasm_shared.ts",
+  "output": "wasm_shared.out"
+}
diff --git a/tests/specs/run/wasm_shared/wasm_shared.out b/tests/specs/run/wasm_shared/wasm_shared.out
new file mode 100644
index 0000000000..e69de29bb2
diff --git a/tests/testdata/run/wasm_shared.ts b/tests/specs/run/wasm_shared/wasm_shared.ts
similarity index 100%
rename from tests/testdata/run/wasm_shared.ts
rename to tests/specs/run/wasm_shared/wasm_shared.ts
diff --git a/tests/specs/run/wasm_streaming_panic_test/__test__.jsonc b/tests/specs/run/wasm_streaming_panic_test/__test__.jsonc
new file mode 100644
index 0000000000..e22e1f98a8
--- /dev/null
+++ b/tests/specs/run/wasm_streaming_panic_test/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run wasm_streaming_panic_test.js",
+  "output": "wasm_streaming_panic_test.js.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/wasm_streaming_panic_test.js b/tests/specs/run/wasm_streaming_panic_test/wasm_streaming_panic_test.js
similarity index 100%
rename from tests/testdata/run/wasm_streaming_panic_test.js
rename to tests/specs/run/wasm_streaming_panic_test/wasm_streaming_panic_test.js
diff --git a/tests/testdata/run/wasm_streaming_panic_test.js.out b/tests/specs/run/wasm_streaming_panic_test/wasm_streaming_panic_test.js.out
similarity index 100%
rename from tests/testdata/run/wasm_streaming_panic_test.js.out
rename to tests/specs/run/wasm_streaming_panic_test/wasm_streaming_panic_test.js.out
diff --git a/tests/specs/run/wasm_unreachable/__test__.jsonc b/tests/specs/run/wasm_unreachable/__test__.jsonc
new file mode 100644
index 0000000000..cd6165629c
--- /dev/null
+++ b/tests/specs/run/wasm_unreachable/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --allow-read wasm_unreachable.js",
+  "output": "wasm_unreachable.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/wasm_unreachable/unreachable.wasm b/tests/specs/run/wasm_unreachable/unreachable.wasm
new file mode 100644
index 0000000000..a4110ee393
Binary files /dev/null and b/tests/specs/run/wasm_unreachable/unreachable.wasm differ
diff --git a/tests/testdata/run/wasm_unreachable.js b/tests/specs/run/wasm_unreachable/wasm_unreachable.js
similarity index 82%
rename from tests/testdata/run/wasm_unreachable.js
rename to tests/specs/run/wasm_unreachable/wasm_unreachable.js
index d6a4f59dbc..36aab0d84f 100644
--- a/tests/testdata/run/wasm_unreachable.js
+++ b/tests/specs/run/wasm_unreachable/wasm_unreachable.js
@@ -1,5 +1,5 @@
 // WebAssembly module containing a single function with an unreachable instruction
-const binary = await Deno.readFile("./assets/unreachable.wasm");
+const binary = await Deno.readFile("./unreachable.wasm");
 
 const module = new WebAssembly.Module(binary);
 const instance = new WebAssembly.Instance(module);
diff --git a/tests/testdata/run/wasm_unreachable.out b/tests/specs/run/wasm_unreachable/wasm_unreachable.out
similarity index 100%
rename from tests/testdata/run/wasm_unreachable.out
rename to tests/specs/run/wasm_unreachable/wasm_unreachable.out
diff --git a/tests/specs/run/wasm_url/__test__.jsonc b/tests/specs/run/wasm_url/__test__.jsonc
new file mode 100644
index 0000000000..a776527b1f
--- /dev/null
+++ b/tests/specs/run/wasm_url/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --allow-net=localhost:4545 wasm_url.js",
+  "output": "wasm_url.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/run/wasm_url.js b/tests/specs/run/wasm_url/wasm_url.js
similarity index 100%
rename from tests/testdata/run/wasm_url.js
rename to tests/specs/run/wasm_url/wasm_url.js
diff --git a/tests/testdata/run/wasm_url.out b/tests/specs/run/wasm_url/wasm_url.out
similarity index 100%
rename from tests/testdata/run/wasm_url.out
rename to tests/specs/run/wasm_url/wasm_url.out
diff --git a/tests/specs/run/weakref/__test__.jsonc b/tests/specs/run/weakref/__test__.jsonc
new file mode 100644
index 0000000000..1a5808ec7b
--- /dev/null
+++ b/tests/specs/run/weakref/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload weakref.ts",
+  "output": "weakref.ts.out"
+}
diff --git a/tests/testdata/run/weakref.ts b/tests/specs/run/weakref/weakref.ts
similarity index 100%
rename from tests/testdata/run/weakref.ts
rename to tests/specs/run/weakref/weakref.ts
diff --git a/tests/testdata/run/weakref.ts.out b/tests/specs/run/weakref/weakref.ts.out
similarity index 100%
rename from tests/testdata/run/weakref.ts.out
rename to tests/specs/run/weakref/weakref.ts.out
diff --git a/tests/specs/run/webstorage_serialization/__test__.jsonc b/tests/specs/run/webstorage_serialization/__test__.jsonc
new file mode 100644
index 0000000000..4362a84b26
--- /dev/null
+++ b/tests/specs/run/webstorage_serialization/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run webstorage/serialization.ts",
+  "output": "webstorage/serialization.ts.out"
+}
diff --git a/tests/specs/run/webstorage_serialization/webstorage/config_a.jsonc b/tests/specs/run/webstorage_serialization/webstorage/config_a.jsonc
new file mode 100644
index 0000000000..875cb60012
--- /dev/null
+++ b/tests/specs/run/webstorage_serialization/webstorage/config_a.jsonc
@@ -0,0 +1,3 @@
+{
+  "compilerOptions": {}
+}
diff --git a/tests/specs/run/webstorage_serialization/webstorage/config_b.jsonc b/tests/specs/run/webstorage_serialization/webstorage/config_b.jsonc
new file mode 100644
index 0000000000..875cb60012
--- /dev/null
+++ b/tests/specs/run/webstorage_serialization/webstorage/config_b.jsonc
@@ -0,0 +1,3 @@
+{
+  "compilerOptions": {}
+}
diff --git a/tests/specs/run/webstorage_serialization/webstorage/fixture.ts b/tests/specs/run/webstorage_serialization/webstorage/fixture.ts
new file mode 100644
index 0000000000..cf4bd9f1f1
--- /dev/null
+++ b/tests/specs/run/webstorage_serialization/webstorage/fixture.ts
@@ -0,0 +1,2 @@
+import "./logger.ts";
+import "./setter.ts";
diff --git a/tests/specs/run/webstorage_serialization/webstorage/logger.ts b/tests/specs/run/webstorage_serialization/webstorage/logger.ts
new file mode 100644
index 0000000000..feadd39eb6
--- /dev/null
+++ b/tests/specs/run/webstorage_serialization/webstorage/logger.ts
@@ -0,0 +1 @@
+console.log(globalThis.localStorage);
diff --git a/tests/testdata/run/webstorage/serialization.ts b/tests/specs/run/webstorage_serialization/webstorage/serialization.ts
similarity index 100%
rename from tests/testdata/run/webstorage/serialization.ts
rename to tests/specs/run/webstorage_serialization/webstorage/serialization.ts
diff --git a/tests/testdata/run/webstorage/serialization.ts.out b/tests/specs/run/webstorage_serialization/webstorage/serialization.ts.out
similarity index 100%
rename from tests/testdata/run/webstorage/serialization.ts.out
rename to tests/specs/run/webstorage_serialization/webstorage/serialization.ts.out
diff --git a/tests/specs/run/webstorage_serialization/webstorage/setter.ts b/tests/specs/run/webstorage_serialization/webstorage/setter.ts
new file mode 100644
index 0000000000..cf5a7bfaf6
--- /dev/null
+++ b/tests/specs/run/webstorage_serialization/webstorage/setter.ts
@@ -0,0 +1 @@
+globalThis.localStorage.setItem("hello", "deno");
diff --git a/tests/specs/run/worker_close_in_wasm_reactions/__test__.jsonc b/tests/specs/run/worker_close_in_wasm_reactions/__test__.jsonc
new file mode 100644
index 0000000000..104b547564
--- /dev/null
+++ b/tests/specs/run/worker_close_in_wasm_reactions/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-read worker_close_in_wasm_reactions.js",
+  "output": "worker_close_in_wasm_reactions.js.out"
+}
diff --git a/tests/specs/run/worker_close_in_wasm_reactions/close_in_wasm_reactions.js b/tests/specs/run/worker_close_in_wasm_reactions/close_in_wasm_reactions.js
new file mode 100644
index 0000000000..abe5731085
--- /dev/null
+++ b/tests/specs/run/worker_close_in_wasm_reactions/close_in_wasm_reactions.js
@@ -0,0 +1,21 @@
+// https://github.com/denoland/deno/issues/12263
+// Test for a panic that happens when a worker is closed in the reactions of a
+// WASM async operation.
+
+// The minimum valid wasm module, plus two additional zero bytes.
+const buffer = new Uint8Array([
+  0x00,
+  0x61,
+  0x73,
+  0x6D,
+  0x01,
+  0x00,
+  0x00,
+  0x00,
+  0x00,
+  0x00,
+]);
+WebAssembly.compile(buffer).catch((err) => {
+  console.log("Error:", err);
+  self.close();
+});
diff --git a/tests/testdata/run/worker_close_in_wasm_reactions.js b/tests/specs/run/worker_close_in_wasm_reactions/worker_close_in_wasm_reactions.js
similarity index 80%
rename from tests/testdata/run/worker_close_in_wasm_reactions.js
rename to tests/specs/run/worker_close_in_wasm_reactions/worker_close_in_wasm_reactions.js
index 95f34e944d..828320a240 100644
--- a/tests/testdata/run/worker_close_in_wasm_reactions.js
+++ b/tests/specs/run/worker_close_in_wasm_reactions/worker_close_in_wasm_reactions.js
@@ -5,6 +5,6 @@
 // WASM async operation.
 
 new Worker(
-  import.meta.resolve("../workers/close_in_wasm_reactions.js"),
+  import.meta.resolve("./close_in_wasm_reactions.js"),
   { type: "module" },
 );
diff --git a/tests/testdata/run/worker_close_in_wasm_reactions.js.out b/tests/specs/run/worker_close_in_wasm_reactions/worker_close_in_wasm_reactions.js.out
similarity index 100%
rename from tests/testdata/run/worker_close_in_wasm_reactions.js.out
rename to tests/specs/run/worker_close_in_wasm_reactions/worker_close_in_wasm_reactions.js.out
diff --git a/tests/specs/run/worker_close_nested/__test__.jsonc b/tests/specs/run/worker_close_nested/__test__.jsonc
new file mode 100644
index 0000000000..5cce107c7a
--- /dev/null
+++ b/tests/specs/run/worker_close_nested/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-read worker_close_nested.js",
+  "output": "worker_close_nested.js.out"
+}
diff --git a/tests/specs/run/worker_close_nested/close_nested_child.js b/tests/specs/run/worker_close_nested/close_nested_child.js
new file mode 100644
index 0000000000..97980c689e
--- /dev/null
+++ b/tests/specs/run/worker_close_nested/close_nested_child.js
@@ -0,0 +1,8 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+console.log("Starting the child worker");
+
+setTimeout(() => {
+  console.log("The child worker survived the death of the parent!!!");
+  Deno.exit(1);
+}, 2000);
diff --git a/tests/specs/run/worker_close_nested/close_nested_parent.js b/tests/specs/run/worker_close_nested/close_nested_parent.js
new file mode 100644
index 0000000000..d1fe47553e
--- /dev/null
+++ b/tests/specs/run/worker_close_nested/close_nested_parent.js
@@ -0,0 +1,13 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+console.log("Starting the parent worker");
+
+new Worker(
+  import.meta.resolve("./close_nested_child.js"),
+  { type: "module" },
+);
+
+self.addEventListener("message", () => {
+  console.log("Closing");
+  self.close();
+});
diff --git a/tests/testdata/run/worker_close_nested.js b/tests/specs/run/worker_close_nested/worker_close_nested.js
similarity index 89%
rename from tests/testdata/run/worker_close_nested.js
rename to tests/specs/run/worker_close_nested/worker_close_nested.js
index 37b6ed9c9a..8d9c88d1cf 100644
--- a/tests/testdata/run/worker_close_nested.js
+++ b/tests/specs/run/worker_close_nested/worker_close_nested.js
@@ -6,7 +6,7 @@
 console.log("Starting the main thread");
 
 const worker = new Worker(
-  import.meta.resolve("../workers/close_nested_parent.js"),
+  import.meta.resolve("./close_nested_parent.js"),
   { type: "module" },
 );
 
diff --git a/tests/testdata/run/worker_close_nested.js.out b/tests/specs/run/worker_close_nested/worker_close_nested.js.out
similarity index 100%
rename from tests/testdata/run/worker_close_nested.js.out
rename to tests/specs/run/worker_close_nested/worker_close_nested.js.out
diff --git a/tests/specs/run/worker_close_race/__test__.jsonc b/tests/specs/run/worker_close_race/__test__.jsonc
new file mode 100644
index 0000000000..bdb9665f7e
--- /dev/null
+++ b/tests/specs/run/worker_close_race/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-read worker_close_race.js",
+  "output": "worker_close_race.js.out"
+}
diff --git a/tests/specs/run/worker_close_race/close_race_worker.js b/tests/specs/run/worker_close_race/close_race_worker.js
new file mode 100644
index 0000000000..6964be34a0
--- /dev/null
+++ b/tests/specs/run/worker_close_race/close_race_worker.js
@@ -0,0 +1,6 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+setTimeout(() => {
+  self.postMessage("");
+  self.close();
+}, 500);
diff --git a/tests/testdata/run/worker_close_race.js b/tests/specs/run/worker_close_race/worker_close_race.js
similarity index 85%
rename from tests/testdata/run/worker_close_race.js
rename to tests/specs/run/worker_close_race/worker_close_race.js
index 1da8324259..188cd9ed88 100644
--- a/tests/testdata/run/worker_close_race.js
+++ b/tests/specs/run/worker_close_race/worker_close_race.js
@@ -5,7 +5,7 @@
 // `Worker.prototype.terminate()`.
 
 const worker = new Worker(
-  import.meta.resolve("../workers/close_race_worker.js"),
+  import.meta.resolve("./close_race_worker.js"),
   { type: "module" },
 );
 
diff --git a/tests/specs/run/worker_close_race/worker_close_race.js.out b/tests/specs/run/worker_close_race/worker_close_race.js.out
new file mode 100644
index 0000000000..e69de29bb2
diff --git a/tests/specs/run/worker_drop_handle_race/__test__.jsonc b/tests/specs/run/worker_drop_handle_race/__test__.jsonc
new file mode 100644
index 0000000000..cc600d5ef4
--- /dev/null
+++ b/tests/specs/run/worker_drop_handle_race/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run --quiet --reload --allow-read worker_drop_handle_race.js",
+  "output": "worker_drop_handle_race.js.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/worker_drop_handle_race/drop_handle_race.js b/tests/specs/run/worker_drop_handle_race/drop_handle_race.js
new file mode 100644
index 0000000000..30676a600a
--- /dev/null
+++ b/tests/specs/run/worker_drop_handle_race/drop_handle_race.js
@@ -0,0 +1,3 @@
+setTimeout(() => {
+  throw new Error();
+}, 1000);
diff --git a/tests/testdata/run/worker_drop_handle_race.js b/tests/specs/run/worker_drop_handle_race/worker_drop_handle_race.js
similarity index 88%
rename from tests/testdata/run/worker_drop_handle_race.js
rename to tests/specs/run/worker_drop_handle_race/worker_drop_handle_race.js
index 731a369648..ef9bcbe072 100644
--- a/tests/testdata/run/worker_drop_handle_race.js
+++ b/tests/specs/run/worker_drop_handle_race/worker_drop_handle_race.js
@@ -7,6 +7,6 @@
 // The exception thrown in the worker will not terminate the worker, but it will
 // propagate to the main thread and cause it to exit.
 new Worker(
-  import.meta.resolve("../workers/drop_handle_race.js"),
+  import.meta.resolve("./drop_handle_race.js"),
   { type: "module" },
 );
diff --git a/tests/testdata/run/worker_drop_handle_race.js.out b/tests/specs/run/worker_drop_handle_race/worker_drop_handle_race.js.out
similarity index 79%
rename from tests/testdata/run/worker_drop_handle_race.js.out
rename to tests/specs/run/worker_drop_handle_race/worker_drop_handle_race.js.out
index 0820f164e5..a1c2e30ad4 100644
--- a/tests/testdata/run/worker_drop_handle_race.js.out
+++ b/tests/specs/run/worker_drop_handle_race/worker_drop_handle_race.js.out
@@ -1,7 +1,7 @@
 error: Uncaught (in worker "") Error
   throw new Error();
         ^
-    at [WILDCARD]/workers/drop_handle_race.js:2:9
+    at [WILDCARD]/drop_handle_race.js:2:9
     at [WILDCARD]
 error: Uncaught (in promise) Error: Unhandled error in child worker.
     at Worker.#pollControl [WILDCARD]
diff --git a/tests/specs/run/worker_drop_handle_race_terminate/__test__.jsonc b/tests/specs/run/worker_drop_handle_race_terminate/__test__.jsonc
new file mode 100644
index 0000000000..e752074ebf
--- /dev/null
+++ b/tests/specs/run/worker_drop_handle_race_terminate/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run worker_drop_handle_race_terminate.js",
+  "output": "worker_drop_handle_race_terminate.js.out"
+}
diff --git a/tests/testdata/run/worker_drop_handle_race_terminate.js b/tests/specs/run/worker_drop_handle_race_terminate/worker_drop_handle_race_terminate.js
similarity index 100%
rename from tests/testdata/run/worker_drop_handle_race_terminate.js
rename to tests/specs/run/worker_drop_handle_race_terminate/worker_drop_handle_race_terminate.js
diff --git a/tests/testdata/run/worker_drop_handle_race_terminate.js.out b/tests/specs/run/worker_drop_handle_race_terminate/worker_drop_handle_race_terminate.js.out
similarity index 100%
rename from tests/testdata/run/worker_drop_handle_race_terminate.js.out
rename to tests/specs/run/worker_drop_handle_race_terminate/worker_drop_handle_race_terminate.js.out
diff --git a/tests/specs/run/worker_event_handler_test/__test__.jsonc b/tests/specs/run/worker_event_handler_test/__test__.jsonc
new file mode 100644
index 0000000000..c07fca97c6
--- /dev/null
+++ b/tests/specs/run/worker_event_handler_test/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-read worker_event_handler_test.js",
+  "output": "worker_event_handler_test.js.out"
+}
diff --git a/tests/testdata/run/worker_event_handler_test.js b/tests/specs/run/worker_event_handler_test/worker_event_handler_test.js
similarity index 51%
rename from tests/testdata/run/worker_event_handler_test.js
rename to tests/specs/run/worker_event_handler_test/worker_event_handler_test.js
index a91b0ec0b1..91c5ba9469 100644
--- a/tests/testdata/run/worker_event_handler_test.js
+++ b/tests/specs/run/worker_event_handler_test/worker_event_handler_test.js
@@ -1,5 +1,5 @@
 const w = new Worker(
-  import.meta.resolve("../workers/worker_event_handlers.js"),
+  import.meta.resolve("./worker_event_handlers.js"),
   { type: "module" },
 );
 w.postMessage({});
diff --git a/tests/testdata/run/worker_event_handler_test.js.out b/tests/specs/run/worker_event_handler_test/worker_event_handler_test.js.out
similarity index 100%
rename from tests/testdata/run/worker_event_handler_test.js.out
rename to tests/specs/run/worker_event_handler_test/worker_event_handler_test.js.out
diff --git a/tests/specs/run/worker_event_handler_test/worker_event_handlers.js b/tests/specs/run/worker_event_handler_test/worker_event_handlers.js
new file mode 100644
index 0000000000..5e457cd2e3
--- /dev/null
+++ b/tests/specs/run/worker_event_handler_test/worker_event_handlers.js
@@ -0,0 +1,26 @@
+self.onmessage = (evt) => {
+  console.log("Target from self.onmessage:", String(evt.target));
+};
+
+self.addEventListener("message", (evt) => {
+  console.log("Target from message event listener:", String(evt.target));
+
+  // Throw an error here so the global's error event will fire.
+  throw new Error("Some error message");
+});
+
+self.onerror = (...args) => {
+  // Take the last 100 characters so the filename doesn't get truncated
+  // depending on the dev's FS structure.
+  args = args.map((v) => typeof v == "string" ? v.slice(-100) : v);
+  console.log("Arguments from self.onerror:", args);
+  return true;
+};
+
+self.addEventListener("error", (evt) => {
+  // Returning true from self.onerror means that subsequent event listeners
+  // should see the event as canceled.
+  console.log("Is event canceled?:", evt.defaultPrevented);
+
+  self.close();
+});
diff --git a/tests/specs/run/worker_message_before_close/__test__.jsonc b/tests/specs/run/worker_message_before_close/__test__.jsonc
new file mode 100644
index 0000000000..ae2d65b919
--- /dev/null
+++ b/tests/specs/run/worker_message_before_close/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --quiet --reload --allow-read worker_message_before_close.js",
+  "output": "worker_message_before_close.js.out"
+}
diff --git a/tests/specs/run/worker_message_before_close/message_before_close.js b/tests/specs/run/worker_message_before_close/message_before_close.js
new file mode 100644
index 0000000000..9364b6d824
--- /dev/null
+++ b/tests/specs/run/worker_message_before_close/message_before_close.js
@@ -0,0 +1,4 @@
+onmessage = () => {
+  postMessage({});
+  close();
+};
diff --git a/tests/testdata/run/worker_message_before_close.js b/tests/specs/run/worker_message_before_close/worker_message_before_close.js
similarity index 89%
rename from tests/testdata/run/worker_message_before_close.js
rename to tests/specs/run/worker_message_before_close/worker_message_before_close.js
index 569388b9bb..d613bd1cac 100644
--- a/tests/testdata/run/worker_message_before_close.js
+++ b/tests/specs/run/worker_message_before_close/worker_message_before_close.js
@@ -2,7 +2,7 @@ const messagesReceived = new Set();
 
 for (let i = 0; i < 4; i++) {
   const worker = new Worker(
-    import.meta.resolve("../workers/message_before_close.js"),
+    import.meta.resolve("./message_before_close.js"),
     { type: "module", name: String(i) },
   );
 
diff --git a/tests/testdata/run/worker_message_before_close.js.out b/tests/specs/run/worker_message_before_close/worker_message_before_close.js.out
similarity index 100%
rename from tests/testdata/run/worker_message_before_close.js.out
rename to tests/specs/run/worker_message_before_close/worker_message_before_close.js.out
diff --git a/tests/specs/run/workspaces/wildcard/__test__.jsonc b/tests/specs/run/workspaces/wildcard/__test__.jsonc
new file mode 100644
index 0000000000..ea467e51b4
--- /dev/null
+++ b/tests/specs/run/workspaces/wildcard/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run -L debug -A main.ts",
+  "output": "main.out",
+  "tempDir": true
+}
diff --git a/tests/specs/run/workspaces/wildcard/deno.json b/tests/specs/run/workspaces/wildcard/deno.json
new file mode 100644
index 0000000000..8c39ec6564
--- /dev/null
+++ b/tests/specs/run/workspaces/wildcard/deno.json
@@ -0,0 +1,8 @@
+{
+  "workspace": [
+    "./packages/*"
+  ],
+  "imports": {
+    "chalk": "npm:chalk"
+  }
+}
diff --git a/tests/specs/run/workspaces/wildcard/main.out b/tests/specs/run/workspaces/wildcard/main.out
new file mode 100644
index 0000000000..72165dbdea
--- /dev/null
+++ b/tests/specs/run/workspaces/wildcard/main.out
@@ -0,0 +1,22 @@
+[WILDCARD]Workspace config generated this import map {
+  "imports": {
+    "chalk": "npm:chalk",
+    "chalk/": "npm:/chalk/"
+  },
+  "scopes": {
+    "./packages/bar/": {
+      "@/": "./packages/bar/",
+      "secret_mod/": "./packages/bar/some_mod/"
+    },
+    "./packages/foo/": {
+      "~/": "./packages/foo/",
+      "foo/": "./packages/foo/bar/"
+    }
+  }
+}
+[WILDCARD]
+hello from foo
+buzz from foo
+hello from bar
+buzz from bar
+[Function: chalk][WILDCARD]
\ No newline at end of file
diff --git a/tests/specs/run/workspaces/wildcard/main.ts b/tests/specs/run/workspaces/wildcard/main.ts
new file mode 100644
index 0000000000..e69143370d
--- /dev/null
+++ b/tests/specs/run/workspaces/wildcard/main.ts
@@ -0,0 +1,5 @@
+import chalk from "chalk";
+import "./packages/foo/mod.ts";
+import "./packages/bar/mod.ts";
+
+console.log(chalk);
diff --git a/tests/specs/run/workspaces/wildcard/packages/bar/deno.json b/tests/specs/run/workspaces/wildcard/packages/bar/deno.json
new file mode 100644
index 0000000000..ef3bfc37af
--- /dev/null
+++ b/tests/specs/run/workspaces/wildcard/packages/bar/deno.json
@@ -0,0 +1,8 @@
+{
+  "name": "asdfasdfasdf",
+  "version": "0.0.0",
+  "imports": {
+    "@/": "./",
+    "secret_mod/": "./some_mod/"
+  }
+}
diff --git a/tests/specs/run/workspaces/wildcard/packages/bar/fizz/buzz.ts b/tests/specs/run/workspaces/wildcard/packages/bar/fizz/buzz.ts
new file mode 100644
index 0000000000..f88d62fcc8
--- /dev/null
+++ b/tests/specs/run/workspaces/wildcard/packages/bar/fizz/buzz.ts
@@ -0,0 +1 @@
+export const buzz = "buzz from bar";
diff --git a/tests/specs/run/workspaces/wildcard/packages/bar/mod.ts b/tests/specs/run/workspaces/wildcard/packages/bar/mod.ts
new file mode 100644
index 0000000000..6f898e3898
--- /dev/null
+++ b/tests/specs/run/workspaces/wildcard/packages/bar/mod.ts
@@ -0,0 +1,5 @@
+import { hello } from "secret_mod/hello.ts";
+import { buzz } from "@/fizz/buzz.ts";
+
+console.log(hello);
+console.log(buzz);
diff --git a/tests/specs/run/workspaces/wildcard/packages/bar/some_mod/hello.ts b/tests/specs/run/workspaces/wildcard/packages/bar/some_mod/hello.ts
new file mode 100644
index 0000000000..1013de8d2e
--- /dev/null
+++ b/tests/specs/run/workspaces/wildcard/packages/bar/some_mod/hello.ts
@@ -0,0 +1 @@
+export const hello = "hello from bar";
diff --git a/tests/specs/run/workspaces/wildcard/packages/foo/bar/hello.ts b/tests/specs/run/workspaces/wildcard/packages/foo/bar/hello.ts
new file mode 100644
index 0000000000..c8a7e57c4d
--- /dev/null
+++ b/tests/specs/run/workspaces/wildcard/packages/foo/bar/hello.ts
@@ -0,0 +1 @@
+export const hello = "hello from foo";
diff --git a/tests/specs/run/workspaces/wildcard/packages/foo/deno.json b/tests/specs/run/workspaces/wildcard/packages/foo/deno.json
new file mode 100644
index 0000000000..46d84f06fa
--- /dev/null
+++ b/tests/specs/run/workspaces/wildcard/packages/foo/deno.json
@@ -0,0 +1,8 @@
+{
+  "name": "qwerqwer",
+  "version": "0.0.0",
+  "imports": {
+    "~/": "./",
+    "foo/": "./bar/"
+  }
+}
diff --git a/tests/specs/run/workspaces/wildcard/packages/foo/fizz/buzz.ts b/tests/specs/run/workspaces/wildcard/packages/foo/fizz/buzz.ts
new file mode 100644
index 0000000000..4e03777d1b
--- /dev/null
+++ b/tests/specs/run/workspaces/wildcard/packages/foo/fizz/buzz.ts
@@ -0,0 +1 @@
+export const buzz = "buzz from foo";
diff --git a/tests/specs/run/workspaces/wildcard/packages/foo/mod.ts b/tests/specs/run/workspaces/wildcard/packages/foo/mod.ts
new file mode 100644
index 0000000000..d7b16dcc05
--- /dev/null
+++ b/tests/specs/run/workspaces/wildcard/packages/foo/mod.ts
@@ -0,0 +1,5 @@
+import { hello } from "foo/hello.ts";
+import { buzz } from "~/fizz/buzz.ts";
+
+console.log(hello);
+console.log(buzz);
diff --git a/tests/specs/schema.json b/tests/specs/schema.json
index 8f3953ee44..2b35d9bd7d 100644
--- a/tests/specs/schema.json
+++ b/tests/specs/schema.json
@@ -36,6 +36,9 @@
         "flaky": {
           "type": "boolean"
         },
+        "symlinkedTempDir": {
+          "type": "boolean"
+        },
         "if": {
           "type": "string",
           "examples": [
diff --git a/tests/specs/task/additional_args/__test__.jsonc b/tests/specs/task/additional_args/__test__.jsonc
index b75c638ff2..713c5a6b60 100644
--- a/tests/specs/task/additional_args/__test__.jsonc
+++ b/tests/specs/task/additional_args/__test__.jsonc
@@ -1,7 +1,4 @@
 {
   "args": "task -q --config deno.json echo 2",
-  "output": "task_additional_args.out",
-  "envs": {
-    "NO_COLOR": "1"
-  }
+  "output": "task_additional_args.out"
 }
diff --git a/tests/specs/task/additional_args_nested_strings/__test__.jsonc b/tests/specs/task/additional_args_nested_strings/__test__.jsonc
index e543e31acf..fe0c326b83 100644
--- a/tests/specs/task/additional_args_nested_strings/__test__.jsonc
+++ b/tests/specs/task/additional_args_nested_strings/__test__.jsonc
@@ -1,7 +1,4 @@
 {
   "args": "task -q --config deno.json echo string \"quoted string\"",
-  "output": "task_additional_args_nested_strings.out",
-  "envs": {
-    "NO_COLOR": "1"
-  }
+  "output": "task_additional_args_nested_strings.out"
 }
diff --git a/tests/specs/task/additional_args_no_logic/__test__.jsonc b/tests/specs/task/additional_args_no_logic/__test__.jsonc
index 849f8bf66f..dc4fbf09a9 100644
--- a/tests/specs/task/additional_args_no_logic/__test__.jsonc
+++ b/tests/specs/task/additional_args_no_logic/__test__.jsonc
@@ -1,7 +1,4 @@
 {
   "args": "task -q --config deno.json echo || echo 5",
-  "output": "task_additional_args_no_logic.out",
-  "envs": {
-    "NO_COLOR": "1"
-  }
+  "output": "task_additional_args_no_logic.out"
 }
diff --git a/tests/specs/task/additional_args_no_shell_expansion/__test__.jsonc b/tests/specs/task/additional_args_no_shell_expansion/__test__.jsonc
index 202321e39f..cb467ea83b 100644
--- a/tests/specs/task/additional_args_no_shell_expansion/__test__.jsonc
+++ b/tests/specs/task/additional_args_no_shell_expansion/__test__.jsonc
@@ -1,7 +1,4 @@
 {
   "args": "task -q --config deno.json echo $(echo 5)",
-  "output": "task_additional_args_no_shell_expansion.out",
-  "envs": {
-    "NO_COLOR": "1"
-  }
+  "output": "task_additional_args_no_shell_expansion.out"
 }
diff --git a/tests/specs/task/bin_package/task.out b/tests/specs/task/bin_package/task.out
index 69b4f75082..d2c130905a 100644
--- a/tests/specs/task/bin_package/task.out
+++ b/tests/specs/task/bin_package/task.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Initialize @denotest/bin@1.0.0
 Task sayhi cli-esm hi hello
diff --git a/tests/specs/task/bin_pkg_with_scope_auto/bin_auto.out b/tests/specs/task/bin_pkg_with_scope_auto/bin_auto.out
index 20865898e3..1eb196a7aa 100644
--- a/tests/specs/task/bin_pkg_with_scope_auto/bin_auto.out
+++ b/tests/specs/task/bin_pkg_with_scope_auto/bin_auto.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fbin
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/bin/0.5.0.tgz
 Initialize @denotest/bin@0.5.0
diff --git a/tests/specs/task/bin_pkg_with_scope_auto/bin_none.out b/tests/specs/task/bin_pkg_with_scope_auto/bin_none.out
index 066c67bd8a..f44b234bf3 100644
--- a/tests/specs/task/bin_pkg_with_scope_auto/bin_none.out
+++ b/tests/specs/task/bin_pkg_with_scope_auto/bin_none.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fbin
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/bin/0.5.0.tgz
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
diff --git a/tests/specs/task/bin_pkg_with_scope_none/bin_none.out b/tests/specs/task/bin_pkg_with_scope_none/bin_none.out
index 066c67bd8a..f44b234bf3 100644
--- a/tests/specs/task/bin_pkg_with_scope_none/bin_none.out
+++ b/tests/specs/task/bin_pkg_with_scope_none/bin_none.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fbin
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/bin/0.5.0.tgz
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
diff --git a/tests/specs/task/boolean_logic/__test__.jsonc b/tests/specs/task/boolean_logic/__test__.jsonc
index c96e2256ca..426a558c00 100644
--- a/tests/specs/task/boolean_logic/__test__.jsonc
+++ b/tests/specs/task/boolean_logic/__test__.jsonc
@@ -1,7 +1,4 @@
 {
   "args": "task -q --config deno.json boolean_logic",
-  "output": "task_boolean_logic.out",
-  "envs": {
-    "NO_COLOR": "1"
-  }
+  "output": "task_boolean_logic.out"
 }
diff --git a/tests/specs/task/both_deno_json_selected/__test__.jsonc b/tests/specs/task/both_deno_json_selected/__test__.jsonc
index 7b0d31cbce..333a314ea4 100644
--- a/tests/specs/task/both_deno_json_selected/__test__.jsonc
+++ b/tests/specs/task/both_deno_json_selected/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "task --config deno.json other",
   "output": "deno_selected.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/task/both_no_arg/__test__.jsonc b/tests/specs/task/both_no_arg/__test__.jsonc
index 7f60fcf366..ad469793b8 100644
--- a/tests/specs/task/both_no_arg/__test__.jsonc
+++ b/tests/specs/task/both_no_arg/__test__.jsonc
@@ -1,8 +1,5 @@
 {
   "args": "task --config deno.json",
   "output": "no_args.out",
-  "envs": {
-    "NO_COLOR": "1"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/task/both_package_json_selected/install.out b/tests/specs/task/both_package_json_selected/install.out
index 645501a3d9..08b70a0f21 100644
--- a/tests/specs/task/both_package_json_selected/install.out
+++ b/tests/specs/task/both_package_json_selected/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Initialize @denotest/bin@1.0.0
diff --git a/tests/specs/task/both_prefers_deno/__test__.jsonc b/tests/specs/task/both_prefers_deno/__test__.jsonc
index 74bfedf8c2..99e9e822ba 100644
--- a/tests/specs/task/both_prefers_deno/__test__.jsonc
+++ b/tests/specs/task/both_prefers_deno/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "task --config deno.json output some text",
   "output": "prefers_deno.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/task/cwd/__test__.jsonc b/tests/specs/task/cwd/__test__.jsonc
index c291fe0c9b..49b6b41782 100644
--- a/tests/specs/task/cwd/__test__.jsonc
+++ b/tests/specs/task/cwd/__test__.jsonc
@@ -1,8 +1,5 @@
 {
   "args": "task -q --config deno.json --cwd .. echo_cwd",
   "output": "task_cwd.out",
-  "envs": {
-    "NO_COLOR": "1"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/task/cwd_resolves_config_from_specified_dir/__test__.jsonc b/tests/specs/task/cwd_resolves_config_from_specified_dir/__test__.jsonc
index d8ba8d97f1..9fc3a488c9 100644
--- a/tests/specs/task/cwd_resolves_config_from_specified_dir/__test__.jsonc
+++ b/tests/specs/task/cwd_resolves_config_from_specified_dir/__test__.jsonc
@@ -1,8 +1,5 @@
 {
   "args": "task -q --cwd deno.json",
   "output": "task_no_args.out",
-  "envs": {
-    "NO_COLOR": "1"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/task/deno_exe_no_env/__test__.jsonc b/tests/specs/task/deno_exe_no_env/__test__.jsonc
index b021669e06..289f9483a5 100644
--- a/tests/specs/task/deno_exe_no_env/__test__.jsonc
+++ b/tests/specs/task/deno_exe_no_env/__test__.jsonc
@@ -1,7 +1,4 @@
 {
   "args": "task -q --config deno.json deno_echo",
-  "output": "task_deno_exe_no_env.out",
-  "envs": {
-    "NO_COLOR": "1"
-  }
+  "output": "task_deno_exe_no_env.out"
 }
diff --git a/tests/specs/task/deno_no_pre_post/__test__.jsonc b/tests/specs/task/deno_no_pre_post/__test__.jsonc
index 17bdc9acef..a29eece48b 100644
--- a/tests/specs/task/deno_no_pre_post/__test__.jsonc
+++ b/tests/specs/task/deno_no_pre_post/__test__.jsonc
@@ -1,8 +1,5 @@
 {
   "args": "task --config deno.json test",
   "output": "bin.out",
-  "envs": {
-    "NO_COLOR": "1"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/task/doc_comments_incorrect/__test__.jsonc b/tests/specs/task/doc_comments_incorrect/__test__.jsonc
index e564690e6d..7346290292 100644
--- a/tests/specs/task/doc_comments_incorrect/__test__.jsonc
+++ b/tests/specs/task/doc_comments_incorrect/__test__.jsonc
@@ -1,6 +1,5 @@
 {
   "args": "task doesntexist",
-  "envs": { "NO_COLOR": "1" },
   "output": "task.out",
   "exitCode": 1
 }
diff --git a/tests/specs/task/doc_comments_no_args/__test__.jsonc b/tests/specs/task/doc_comments_no_args/__test__.jsonc
index 9843fa5abb..f3e76cdaa7 100644
--- a/tests/specs/task/doc_comments_no_args/__test__.jsonc
+++ b/tests/specs/task/doc_comments_no_args/__test__.jsonc
@@ -1,6 +1,5 @@
 {
   "args": "task",
-  "envs": { "NO_COLOR": "1" },
   "output": "task.out",
   "exitCode": 0
 }
diff --git a/tests/specs/task/exit_code_5/__test__.jsonc b/tests/specs/task/exit_code_5/__test__.jsonc
index 123710b788..0a09cd57f8 100644
--- a/tests/specs/task/exit_code_5/__test__.jsonc
+++ b/tests/specs/task/exit_code_5/__test__.jsonc
@@ -1,8 +1,5 @@
 {
   "args": "task --config deno.json exit_code_5",
   "output": "task_exit_code_5.out",
-  "envs": {
-    "NO_COLOR": "1"
-  },
   "exitCode": 5
 }
diff --git a/tests/specs/task/init_cwd/__test__.jsonc b/tests/specs/task/init_cwd/__test__.jsonc
index e40d7fef3d..b228e94e6a 100644
--- a/tests/specs/task/init_cwd/__test__.jsonc
+++ b/tests/specs/task/init_cwd/__test__.jsonc
@@ -1,8 +1,5 @@
 {
   "args": "task -q --config deno.json --cwd .. echo_init_cwd",
   "output": "task_init_cwd.out",
-  "envs": {
-    "NO_COLOR": "1"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/task/init_cwd_already_set/__test__.jsonc b/tests/specs/task/init_cwd_already_set/__test__.jsonc
index 30e2091ea7..27b817916f 100644
--- a/tests/specs/task/init_cwd_already_set/__test__.jsonc
+++ b/tests/specs/task/init_cwd_already_set/__test__.jsonc
@@ -2,7 +2,6 @@
   "args": "task -q --config deno.json echo_init_cwd",
   "output": "task_init_cwd_already_set.out",
   "envs": {
-    "NO_COLOR": "1",
     "INIT_CWD": "HELLO"
   },
   "exitCode": 0
diff --git a/tests/specs/task/no_args/__test__.jsonc b/tests/specs/task/no_args/__test__.jsonc
index 6347c5989c..6a0c23750a 100644
--- a/tests/specs/task/no_args/__test__.jsonc
+++ b/tests/specs/task/no_args/__test__.jsonc
@@ -1,8 +1,5 @@
 {
   "args": "task -q --config deno.json",
   "output": "task_no_args.out",
-  "envs": {
-    "NO_COLOR": "1"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/task/non_existent/__test__.jsonc b/tests/specs/task/non_existent/__test__.jsonc
index e34674beef..f0394819be 100644
--- a/tests/specs/task/non_existent/__test__.jsonc
+++ b/tests/specs/task/non_existent/__test__.jsonc
@@ -1,8 +1,5 @@
 {
   "args": "task --config deno.json non_existent",
   "output": "task_non_existent.out",
-  "envs": {
-    "NO_COLOR": "1"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/task/npx_non_existent/__test__.jsonc b/tests/specs/task/npx_non_existent/__test__.jsonc
index 8678a37bd3..d0d3416464 100644
--- a/tests/specs/task/npx_non_existent/__test__.jsonc
+++ b/tests/specs/task/npx_non_existent/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "task non-existent",
   "output": "non_existent.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/task/package_json_echo/__test__.jsonc b/tests/specs/task/package_json_echo/__test__.jsonc
index 616f72f78f..e6f0708b84 100644
--- a/tests/specs/task/package_json_echo/__test__.jsonc
+++ b/tests/specs/task/package_json_echo/__test__.jsonc
@@ -1,9 +1,5 @@
 {
   "args": "task --quiet echo",
   "output": "echo.out",
-  "envs": {
-    "NO_COLOR": "1",
-    "NPM_CONFIG_REGISTRY": "http://localhost:4260/"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/task/package_json_no_arg/__test__.jsonc b/tests/specs/task/package_json_no_arg/__test__.jsonc
index 4ee627dd2e..6b4ffa96d7 100644
--- a/tests/specs/task/package_json_no_arg/__test__.jsonc
+++ b/tests/specs/task/package_json_no_arg/__test__.jsonc
@@ -1,8 +1,5 @@
 {
   "args": "task",
   "output": "no_args.out",
-  "envs": {
-    "NO_COLOR": "1"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/task/package_json_node_modules_dir_none/__test__.jsonc b/tests/specs/task/package_json_node_modules_dir_none/__test__.jsonc
new file mode 100644
index 0000000000..21d9d73ba0
--- /dev/null
+++ b/tests/specs/task/package_json_node_modules_dir_none/__test__.jsonc
@@ -0,0 +1,6 @@
+{
+  "tempDir": true,
+  "args": "task echo",
+  "output": "bin.out",
+  "exitCode": 0
+}
diff --git a/tests/specs/task/package_json_node_modules_dir_none/bin.out b/tests/specs/task/package_json_node_modules_dir_none/bin.out
new file mode 100644
index 0000000000..ff60cc3d0b
--- /dev/null
+++ b/tests/specs/task/package_json_node_modules_dir_none/bin.out
@@ -0,0 +1,8 @@
+[UNORDERED_START]
+Download http://localhost:4260/@denotest%2fbin
+Download http://localhost:4260/@denotest/bin/1.0.0.tgz
+Download http://localhost:4260/@denotest/bin/0.5.0.tgz
+[UNORDERED_END]
+Task echo deno eval 'console.log(1)' && cli-esm hi
+1
+hi
diff --git a/tests/specs/task/package_json_node_modules_dir_none/deno.json b/tests/specs/task/package_json_node_modules_dir_none/deno.json
new file mode 100644
index 0000000000..38af4024b0
--- /dev/null
+++ b/tests/specs/task/package_json_node_modules_dir_none/deno.json
@@ -0,0 +1,3 @@
+{
+  "nodeModulesDir": "none"
+}
diff --git a/tests/testdata/task/package_json_node_modules_dir_false/package.json b/tests/specs/task/package_json_node_modules_dir_none/package.json
similarity index 67%
rename from tests/testdata/task/package_json_node_modules_dir_false/package.json
rename to tests/specs/task/package_json_node_modules_dir_none/package.json
index 081e076b9f..713a9dc5b4 100644
--- a/tests/testdata/task/package_json_node_modules_dir_false/package.json
+++ b/tests/specs/task/package_json_node_modules_dir_none/package.json
@@ -1,6 +1,6 @@
 {
   "scripts": {
-    "echo": "deno eval 'console.log(1)'"
+    "echo": "deno eval 'console.log(1)' && cli-esm hi"
   },
   "dependencies": {
     "@denotest/bin": "0.5",
diff --git a/tests/specs/task/piped_stdin/__test__.jsonc b/tests/specs/task/piped_stdin/__test__.jsonc
index 73220430a2..541e53b177 100644
--- a/tests/specs/task/piped_stdin/__test__.jsonc
+++ b/tests/specs/task/piped_stdin/__test__.jsonc
@@ -1,7 +1,4 @@
 {
   "args": "task -q --config deno.json piped",
-  "output": "task_piped_stdin.out",
-  "envs": {
-    "NO_COLOR": "1"
-  }
+  "output": "task_piped_stdin.out"
 }
diff --git a/tests/specs/task/post/__test__.jsonc b/tests/specs/task/post/__test__.jsonc
index 3ea55d4561..d22f77cc2b 100644
--- a/tests/specs/task/post/__test__.jsonc
+++ b/tests/specs/task/post/__test__.jsonc
@@ -1,8 +1,5 @@
 {
   "args": "task test",
   "output": "bin.out",
-  "envs": {
-    "NO_COLOR": "1"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/task/post_only/__test__.jsonc b/tests/specs/task/post_only/__test__.jsonc
index 4c37e3e63e..606f9eb1f5 100644
--- a/tests/specs/task/post_only/__test__.jsonc
+++ b/tests/specs/task/post_only/__test__.jsonc
@@ -1,8 +1,5 @@
 {
   "args": "task test",
   "output": "bin.out",
-  "envs": {
-    "NO_COLOR": "1"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/task/pre/__test__.jsonc b/tests/specs/task/pre/__test__.jsonc
index 3ea55d4561..d22f77cc2b 100644
--- a/tests/specs/task/pre/__test__.jsonc
+++ b/tests/specs/task/pre/__test__.jsonc
@@ -1,8 +1,5 @@
 {
   "args": "task test",
   "output": "bin.out",
-  "envs": {
-    "NO_COLOR": "1"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/task/pre_only/__test__.jsonc b/tests/specs/task/pre_only/__test__.jsonc
index 4c37e3e63e..606f9eb1f5 100644
--- a/tests/specs/task/pre_only/__test__.jsonc
+++ b/tests/specs/task/pre_only/__test__.jsonc
@@ -1,8 +1,5 @@
 {
   "args": "task test",
   "output": "bin.out",
-  "envs": {
-    "NO_COLOR": "1"
-  },
   "exitCode": 1
 }
diff --git a/tests/specs/task/pre_post/__test__.jsonc b/tests/specs/task/pre_post/__test__.jsonc
index 3ea55d4561..d22f77cc2b 100644
--- a/tests/specs/task/pre_post/__test__.jsonc
+++ b/tests/specs/task/pre_post/__test__.jsonc
@@ -1,8 +1,5 @@
 {
   "args": "task test",
   "output": "bin.out",
-  "envs": {
-    "NO_COLOR": "1"
-  },
   "exitCode": 0
 }
diff --git a/tests/specs/test/captured_output/__test__.jsonc b/tests/specs/test/captured_output/__test__.jsonc
index f56c54555f..f320f9581d 100644
--- a/tests/specs/test/captured_output/__test__.jsonc
+++ b/tests/specs/test/captured_output/__test__.jsonc
@@ -1,6 +1,5 @@
 {
   "args": "test -A captured_output.ts",
   "output": "main.out",
-  "envs": { "NO_COLOR": "1" },
   "exitCode": 0
 }
diff --git a/tests/specs/test/doc_ts_expect_error/__test__.jsonc b/tests/specs/test/doc_ts_expect_error/__test__.jsonc
new file mode 100644
index 0000000000..ba64887a32
--- /dev/null
+++ b/tests/specs/test/doc_ts_expect_error/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "test --doc mod.ts",
+  "exitCode": 0,
+  "output": "mod.out"
+}
diff --git a/tests/specs/test/doc_ts_expect_error/mod.out b/tests/specs/test/doc_ts_expect_error/mod.out
new file mode 100644
index 0000000000..d464d13d71
--- /dev/null
+++ b/tests/specs/test/doc_ts_expect_error/mod.out
@@ -0,0 +1,8 @@
+Check [WILDCARD]/mod.ts
+Check [WILDCARD]/mod.ts$2-10.ts
+running 0 tests from ./mod.ts
+running 1 test from ./mod.ts$2-10.ts
+[WILDCARD]/mod.ts$2-10.ts ... ok ([WILDCARD]ms)
+
+ok | 1 passed | 0 failed ([WILDCARD]ms)
+
diff --git a/tests/specs/test/doc_ts_expect_error/mod.ts b/tests/specs/test/doc_ts_expect_error/mod.ts
new file mode 100644
index 0000000000..eeace602a9
--- /dev/null
+++ b/tests/specs/test/doc_ts_expect_error/mod.ts
@@ -0,0 +1,13 @@
+/**
+ * ```ts
+ * import { add } from "./mod.ts";
+ *
+ * add(1, 2);
+ *
+ * // @ts-expect-error: can only add numbers
+ * add('1', '2');
+ * ```
+ */
+export function add(first: number, second: number) {
+  return first + second;
+}
diff --git a/tests/specs/test/document/__test__.jsonc b/tests/specs/test/document/__test__.jsonc
new file mode 100644
index 0000000000..cf73b4bab8
--- /dev/null
+++ b/tests/specs/test/document/__test__.jsonc
@@ -0,0 +1,9 @@
+{
+  "tests": {
+    "document": {
+      "args": "test document_test.js",
+      "exitCode": 1,
+      "output": "document_test.out"
+    }
+  }
+}
diff --git a/tests/specs/test/document/document_test.js b/tests/specs/test/document/document_test.js
new file mode 100644
index 0000000000..d60d6893cc
--- /dev/null
+++ b/tests/specs/test/document/document_test.js
@@ -0,0 +1,3 @@
+Deno.test("document query selector", () => {
+  document.querySelector("div");
+});
diff --git a/tests/specs/test/document/document_test.out b/tests/specs/test/document/document_test.out
new file mode 100644
index 0000000000..342cee0e47
--- /dev/null
+++ b/tests/specs/test/document/document_test.out
@@ -0,0 +1,22 @@
+running 1 test from ./document_test.js
+document query selector ... FAILED [WILDCARD]
+
+ ERRORS 
+
+document query selector => ./document_test.js:1:6
+error: ReferenceError: document is not defined
+  document.querySelector("div");
+  ^
+    at [WILDCARD]document_test.js:2:3
+
+    info: document global is not available in Deno.
+    hint: Use a library like happy-dom, deno_dom, linkedom or JSDom
+          and setup the document global according to the library documentation.
+
+ FAILURES 
+
+document query selector => ./document_test.js:1:6
+
+FAILED | 0 passed | 1 failed ([WILDCARD])
+
+error: Test failed
diff --git a/tests/specs/test/markdown_ts_expect_error/__test__.jsonc b/tests/specs/test/markdown_ts_expect_error/__test__.jsonc
new file mode 100644
index 0000000000..ad73f6df6f
--- /dev/null
+++ b/tests/specs/test/markdown_ts_expect_error/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "test --doc main.md",
+  "exitCode": 0,
+  "output": "main.out"
+}
diff --git a/tests/specs/test/markdown_ts_expect_error/main.md b/tests/specs/test/markdown_ts_expect_error/main.md
new file mode 100644
index 0000000000..9be70e919c
--- /dev/null
+++ b/tests/specs/test/markdown_ts_expect_error/main.md
@@ -0,0 +1,8 @@
+# Documentation
+
+This test case checks if `@ts-expect-error` comment works as expected.
+
+```ts
+// @ts-expect-error
+const a: string = 42;
+```
diff --git a/tests/specs/test/markdown_ts_expect_error/main.out b/tests/specs/test/markdown_ts_expect_error/main.out
new file mode 100644
index 0000000000..65990cd3f0
--- /dev/null
+++ b/tests/specs/test/markdown_ts_expect_error/main.out
@@ -0,0 +1,6 @@
+Check [WILDCARD]/main.md$5-9.ts
+running 1 test from ./main.md$5-9.ts
+[WILDCARD]/main.md$5-9.ts ... ok ([WILDCARD]ms)
+
+ok | 1 passed | 0 failed ([WILDCARD]ms)
+
diff --git a/tests/specs/test/no_color/__test__.jsonc b/tests/specs/test/no_color/__test__.jsonc
index 154baa8c19..2c4ae3868d 100644
--- a/tests/specs/test/no_color/__test__.jsonc
+++ b/tests/specs/test/no_color/__test__.jsonc
@@ -1,8 +1,5 @@
 {
   "args": "test main.ts",
   "exitCode": 1,
-  "envs": {
-    "NO_COLOR": "1"
-  },
   "output": "main.out"
 }
diff --git a/tests/specs/test/package_json_basic/install.out b/tests/specs/test/package_json_basic/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/test/package_json_basic/install.out
+++ b/tests/specs/test/package_json_basic/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/test/package_json_basic_auto_install/test.out b/tests/specs/test/package_json_basic_auto_install/test.out
index 2f109ef38e..749c395485 100644
--- a/tests/specs/test/package_json_basic_auto_install/test.out
+++ b/tests/specs/test/package_json_basic_auto_install/test.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 Check file://[WILDCARD]/lib.test.ts
diff --git a/tests/specs/test/steps_tap_failing_steps/__test__.jsonc b/tests/specs/test/steps_tap_failing_steps/__test__.jsonc
index fc83a7cdf9..f1e5b21082 100644
--- a/tests/specs/test/steps_tap_failing_steps/__test__.jsonc
+++ b/tests/specs/test/steps_tap_failing_steps/__test__.jsonc
@@ -1,8 +1,5 @@
 {
   "args": "test --reporter=tap failing_steps.ts",
   "exitCode": 1,
-  "envs": {
-    "NO_COLOR": "1"
-  },
   "output": "failing_steps.tap.out"
 }
diff --git a/tests/testdata/assets/node-gyp/node-v20.11.1-headers.tar.gz b/tests/testdata/assets/node-gyp/node-v20.11.1-headers.tar.gz
new file mode 100644
index 0000000000..f63aba0db0
Binary files /dev/null and b/tests/testdata/assets/node-gyp/node-v20.11.1-headers.tar.gz differ
diff --git a/tests/testdata/assets/node-gyp/v20.11.1__win-x64__node.lib.tar.gz b/tests/testdata/assets/node-gyp/v20.11.1__win-x64__node.lib.tar.gz
new file mode 100644
index 0000000000..dccc662432
Binary files /dev/null and b/tests/testdata/assets/node-gyp/v20.11.1__win-x64__node.lib.tar.gz differ
diff --git a/tests/testdata/compile/node_modules_symlink_outside/main_compile_folder.out b/tests/testdata/compile/node_modules_symlink_outside/main_compile_folder.out
index 2067bf1c60..1a7eb0a4f2 100644
--- a/tests/testdata/compile/node_modules_symlink_outside/main_compile_folder.out
+++ b/tests/testdata/compile/node_modules_symlink_outside/main_compile_folder.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 Check file:///[WILDCARD]/node_modules_symlink_outside/main.ts
diff --git a/tests/testdata/coverage/complex.ts b/tests/testdata/coverage/complex.ts
index d128b54373..316986cd22 100644
--- a/tests/testdata/coverage/complex.ts
+++ b/tests/testdata/coverage/complex.ts
@@ -1,3 +1,8 @@
+/**
+ * @module
+ * Complex module
+ */
+
 // This entire interface should be completely ignored by the coverage tool.
 export interface Complex {
   // These comments should be ignored.
@@ -19,6 +24,7 @@ function dependency(
   bar: string,
   baz: string,
 ): Complex {
+  // inline comment in tested function
   return {
     foo,
     bar,
@@ -34,6 +40,9 @@ export function complex(
   bar: string,
   baz: string,
 ): Complex {
+  /*
+   * block comment in tested function
+   */
   return dependency(
     foo,
     bar,
@@ -48,6 +57,7 @@ export function unused(
   bar: string,
   baz: string,
 ): Complex {
+  // inline comment in untested function
   return complex(
     foo,
     bar,
@@ -62,6 +72,9 @@ export const π = Math.PI;
 // And same applies for this one, this one is unused and will show up in
 // lacking coverage.
 export function ƒ(): number {
+  /*
+   * block comment in untested function
+   */
   return (
     0
   );
diff --git a/tests/testdata/coverage/complex_expected.lcov b/tests/testdata/coverage/complex_expected.lcov
index 94b86465ae..7e5c0f40f6 100644
--- a/tests/testdata/coverage/complex_expected.lcov
+++ b/tests/testdata/coverage/complex_expected.lcov
@@ -1,8 +1,8 @@
 SF:[WILDCARD]complex.ts
-FN:17,dependency
-FN:32,complex
-FN:46,unused
-FN:64,ƒ
+FN:22,dependency
+FN:38,complex
+FN:55,unused
+FN:74,ƒ
 FNDA:1,dependency
 FNDA:1,complex
 FNDA:0,unused
@@ -11,57 +11,41 @@ FNF:4
 FNH:2
 BRF:0
 BRH:0
-DA:1,1
-DA:13,1
-DA:14,1
-DA:15,1
-DA:16,1
-DA:17,2
-DA:18,2
-DA:19,2
-DA:20,2
 DA:22,2
 DA:23,2
 DA:24,2
 DA:25,2
-DA:26,2
-DA:27,2
-DA:29,1
-DA:30,1
-DA:31,1
-DA:32,1
-DA:33,1
-DA:34,1
-DA:35,1
-DA:37,2
-DA:38,2
-DA:39,2
-DA:40,2
-DA:42,2
-DA:44,1
-DA:45,1
-DA:46,0
-DA:47,0
-DA:48,0
-DA:49,0
-DA:51,0
-DA:52,0
-DA:53,0
-DA:54,0
+DA:28,2
+DA:29,2
+DA:30,2
+DA:31,2
+DA:32,2
+DA:33,2
+DA:38,1
+DA:39,1
+DA:40,1
+DA:41,1
+DA:46,2
+DA:47,2
+DA:48,2
+DA:49,2
+DA:51,2
+DA:55,0
 DA:56,0
-DA:58,1
-DA:59,1
-DA:60,1
-DA:62,1
-DA:63,1
+DA:57,0
+DA:58,0
+DA:61,0
+DA:62,0
+DA:63,0
 DA:64,0
-DA:65,0
 DA:66,0
-DA:68,0
 DA:70,1
-DA:71,0
-DA:73,1
-DA:74,1
-LH:37
-LF:51
+DA:74,0
+DA:78,0
+DA:79,0
+DA:81,0
+DA:84,0
+DA:87,1
+LH:21
+LF:35
 end_of_record
diff --git a/tests/testdata/coverage/complex_expected.out b/tests/testdata/coverage/complex_expected.out
index 3d5f6a0ab6..f626024b96 100644
--- a/tests/testdata/coverage/complex_expected.out
+++ b/tests/testdata/coverage/complex_expected.out
@@ -1,20 +1,21 @@
-cover [WILDCARD]/coverage/complex.ts ... 72.549% (37/51)
-  46 | export function unused(
-  47 |   foo: string,
-  48 |   bar: string,
-  49 |   baz: string,
+cover [WILDCARD]/coverage/complex.ts ... 60.000% (21/35)
+  55 | export function unused(
+  56 |   foo: string,
+  57 |   bar: string,
+  58 |   baz: string,
 -----|-----
-  51 |   return complex(
-  52 |     foo,
-  53 |     bar,
-  54 |     baz,
+  61 |   return complex(
+  62 |     foo,
+  63 |     bar,
+  64 |     baz,
 -----|-----
-  56 | }
+  66 | }
 -----|-----
-  64 | export function ƒ(): number {
-  65 |   return (
-  66 |     0
+  74 | export function ƒ(): number {
 -----|-----
-  68 | }
+  78 |   return (
+  79 |     0
 -----|-----
-  71 | console.log("%s", () => 1);
+  81 | }
+-----|-----
+  84 | console.log("%s", () => 1);
diff --git a/tests/testdata/npm/deno_run_cowsay_no_permissions.out b/tests/testdata/npm/deno_run_cowsay_no_permissions.out
index 6434620e2e..25b79d9a7d 100644
--- a/tests/testdata/npm/deno_run_cowsay_no_permissions.out
+++ b/tests/testdata/npm/deno_run_cowsay_no_permissions.out
@@ -1,2 +1,2 @@
-error: Uncaught NotCapable: Requires read access to <CWD>, specify the required permissions during compilation using `deno compile --allow-read`
+error: Uncaught (in promise) NotCapable: Requires read access to <CWD>, specify the required permissions during compilation using `deno compile --allow-read`
 [WILDCARD]
diff --git a/tests/testdata/npm/peer_deps_with_copied_folders/main.out b/tests/testdata/npm/peer_deps_with_copied_folders/main.out
index 3c133bcde4..b7a5835577 100644
--- a/tests/testdata/npm/peer_deps_with_copied_folders/main.out
+++ b/tests/testdata/npm/peer_deps_with_copied_folders/main.out
@@ -1,7 +1,7 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/peer-dep-test-child
-Download http://localhost:4260/@denotest/peer-dep-test-grandchild
-Download http://localhost:4260/@denotest/peer-dep-test-peer
+Download http://localhost:4260/@denotest%2fpeer-dep-test-child
+Download http://localhost:4260/@denotest%2fpeer-dep-test-grandchild
+Download http://localhost:4260/@denotest%2fpeer-dep-test-peer
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/peer-dep-test-child/1.0.0.tgz
diff --git a/tests/testdata/npm/peer_deps_with_copied_folders/main_node_modules_reload.out b/tests/testdata/npm/peer_deps_with_copied_folders/main_node_modules_reload.out
index 9c81452118..18d7f7865b 100644
--- a/tests/testdata/npm/peer_deps_with_copied_folders/main_node_modules_reload.out
+++ b/tests/testdata/npm/peer_deps_with_copied_folders/main_node_modules_reload.out
@@ -1,7 +1,7 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/peer-dep-test-child
-Download http://localhost:4260/@denotest/peer-dep-test-grandchild
-Download http://localhost:4260/@denotest/peer-dep-test-peer
+Download http://localhost:4260/@denotest%2fpeer-dep-test-child
+Download http://localhost:4260/@denotest%2fpeer-dep-test-grandchild
+Download http://localhost:4260/@denotest%2fpeer-dep-test-peer
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/peer-dep-test-child/1.0.0.tgz
diff --git a/tests/testdata/npm/run_existing_npm_package/main.out b/tests/testdata/npm/run_existing_npm_package/main.out
index 147ed6a995..373059db53 100644
--- a/tests/testdata/npm/run_existing_npm_package/main.out
+++ b/tests/testdata/npm/run_existing_npm_package/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/bin/0.5.0.tgz
 Initialize @denotest/bin@0.5.0
diff --git a/tests/testdata/run/014_duplicate_import.ts b/tests/testdata/run/014_duplicate_import.ts
deleted file mode 100644
index c7dd881cf0..0000000000
--- a/tests/testdata/run/014_duplicate_import.ts
+++ /dev/null
@@ -1,9 +0,0 @@
-// with all the imports of the same module, the module should only be
-// instantiated once
-import "../subdir/auto_print_hello.ts";
-
-import "../subdir/auto_print_hello.ts";
-
-(async () => {
-  await import("../subdir/auto_print_hello.ts");
-})();
diff --git a/tests/testdata/run/020_json_modules.ts b/tests/testdata/run/020_json_modules.ts
deleted file mode 100644
index b4ae606654..0000000000
--- a/tests/testdata/run/020_json_modules.ts
+++ /dev/null
@@ -1,2 +0,0 @@
-import config from "../subdir/config.json";
-console.log(JSON.stringify(config));
diff --git a/tests/testdata/run/021_mjs_modules.ts b/tests/testdata/run/021_mjs_modules.ts
deleted file mode 100644
index 838cd2c382..0000000000
--- a/tests/testdata/run/021_mjs_modules.ts
+++ /dev/null
@@ -1,2 +0,0 @@
-import { isMod5 } from "../subdir/mod5.mjs";
-console.log(isMod5);
diff --git a/tests/testdata/run/035_cached_only_flag.out b/tests/testdata/run/035_cached_only_flag.out
deleted file mode 100644
index f677ec9153..0000000000
--- a/tests/testdata/run/035_cached_only_flag.out
+++ /dev/null
@@ -1 +0,0 @@
-error: Specifier not found in cache: "http://127.0.0.1:4545/run/019_media_types.ts", --cached-only is specified.
diff --git a/tests/testdata/run/044_bad_resource.ts b/tests/testdata/run/044_bad_resource.ts
deleted file mode 100644
index b956a3e3f2..0000000000
--- a/tests/testdata/run/044_bad_resource.ts
+++ /dev/null
@@ -1,3 +0,0 @@
-const file = await Deno.open("./run/044_bad_resource.ts", { read: true });
-file.close();
-await file.seek(10, 0);
diff --git a/tests/testdata/run/add.cjs b/tests/testdata/run/add.cjs
new file mode 100644
index 0000000000..2a886fbc18
--- /dev/null
+++ b/tests/testdata/run/add.cjs
@@ -0,0 +1,3 @@
+module.exports.add = function (a, b) {
+  return a + b;
+};
diff --git a/tests/testdata/run/config_json_import.ts b/tests/testdata/run/config_json_import.ts
deleted file mode 100644
index 7141f14950..0000000000
--- a/tests/testdata/run/config_json_import.ts
+++ /dev/null
@@ -1,2 +0,0 @@
-import config from "../jsx/deno-jsx.json" with { type: "json" };
-console.log(config);
diff --git a/tests/testdata/run/error_002.ts b/tests/testdata/run/error_002.ts
deleted file mode 100644
index 5f8179bbeb..0000000000
--- a/tests/testdata/run/error_002.ts
+++ /dev/null
@@ -1,7 +0,0 @@
-import { throwsError } from "../subdir/mod1.ts";
-
-function foo() {
-  throwsError();
-}
-
-foo();
diff --git a/tests/testdata/run/error_015_dynamic_import_permissions.js b/tests/testdata/run/error_015_dynamic_import_permissions.js
deleted file mode 100644
index bdf423b59c..0000000000
--- a/tests/testdata/run/error_015_dynamic_import_permissions.js
+++ /dev/null
@@ -1,3 +0,0 @@
-(async () => {
-  await import("" + "http://example.com/subdir/mod4.js");
-})();
diff --git a/tests/testdata/run/error_no_check.ts b/tests/testdata/run/error_no_check.ts
deleted file mode 100644
index 2da01e639a..0000000000
--- a/tests/testdata/run/error_no_check.ts
+++ /dev/null
@@ -1 +0,0 @@
-export { AnInterface, isAnInterface } from "../subdir/type_and_code.ts";
diff --git a/tests/testdata/run/error_no_check.ts.out b/tests/testdata/run/error_no_check.ts.out
deleted file mode 100644
index 78f478045d..0000000000
--- a/tests/testdata/run/error_no_check.ts.out
+++ /dev/null
@@ -1,2 +0,0 @@
-error: Uncaught SyntaxError: The requested module '../subdir/type_and_code.ts' does not provide an export named 'AnInterface'
-[WILDCARD]
\ No newline at end of file
diff --git a/tests/testdata/run/error_type_definitions.ts b/tests/testdata/run/error_type_definitions.ts
deleted file mode 100644
index 86675cbaae..0000000000
--- a/tests/testdata/run/error_type_definitions.ts
+++ /dev/null
@@ -1,5 +0,0 @@
-// @deno-types="../type_definitions/bar.d.ts"
-import { Bar } from "../type_definitions/bar.js";
-
-const bar = new Bar();
-console.log(bar);
diff --git a/tests/testdata/run/fix_emittable_skipped.js b/tests/testdata/run/fix_emittable_skipped.js
deleted file mode 100644
index a4ccc9efda..0000000000
--- a/tests/testdata/run/fix_emittable_skipped.js
+++ /dev/null
@@ -1,7 +0,0 @@
-/// <reference types="../subdir/emittable.d.ts" />
-
-import "../subdir/polyfill.ts";
-
-export const a = "a";
-
-console.log(globalThis.polyfill);
diff --git a/tests/testdata/run/fix_js_import_js.ts b/tests/testdata/run/fix_js_import_js.ts
deleted file mode 100644
index 0f01877cd8..0000000000
--- a/tests/testdata/run/fix_js_import_js.ts
+++ /dev/null
@@ -1,3 +0,0 @@
-import { isMod4 } from "../subdir/mod6.js";
-
-console.log(isMod4);
diff --git a/tests/testdata/run/fix_js_imports.ts b/tests/testdata/run/fix_js_imports.ts
deleted file mode 100644
index 6ed13bae30..0000000000
--- a/tests/testdata/run/fix_js_imports.ts
+++ /dev/null
@@ -1,3 +0,0 @@
-import * as amdLike from "../subdir/amd_like.js";
-
-console.log(amdLike);
diff --git a/tests/testdata/run/import_type.ts b/tests/testdata/run/import_type.ts
deleted file mode 100644
index 22c639cbcf..0000000000
--- a/tests/testdata/run/import_type.ts
+++ /dev/null
@@ -1,5 +0,0 @@
-import { type B, create } from "../subdir/export_types.ts";
-
-const b: B = create();
-
-console.log(b);
diff --git a/tests/testdata/run/issue13562.ts b/tests/testdata/run/issue13562.ts
deleted file mode 100644
index afbf69f99e..0000000000
--- a/tests/testdata/run/issue13562.ts
+++ /dev/null
@@ -1,3 +0,0 @@
-import { printHello3 } from "../subdir/mod1.ts?q=.json";
-
-printHello3();
diff --git a/tests/testdata/run/lock_check_ok.json b/tests/testdata/run/lock_check_ok.json
deleted file mode 100644
index 94de0f6307..0000000000
--- a/tests/testdata/run/lock_check_ok.json
+++ /dev/null
@@ -1,4 +0,0 @@
-{
-  "http://127.0.0.1:4545/subdir/print_hello.ts": "fa6692c8f9ff3fb107e773c3ece5274e9d08be282867a1e3ded1d9c00fcaa63c",
-  "http://127.0.0.1:4545/run/003_relative_import.ts": "a1572e8fd2c2712b33f04aed2561505b5feb2c8696f1f2cded3de7127931b97e"
-}
diff --git a/tests/testdata/run/lock_v2_check_ok.json b/tests/testdata/run/lock_v2_check_ok.json
deleted file mode 100644
index 63bec862a7..0000000000
--- a/tests/testdata/run/lock_v2_check_ok.json
+++ /dev/null
@@ -1,7 +0,0 @@
-{
-  "version": "2",
-  "remote": {
-    "http://127.0.0.1:4545/subdir/print_hello.ts": "fa6692c8f9ff3fb107e773c3ece5274e9d08be282867a1e3ded1d9c00fcaa63c",
-    "http://127.0.0.1:4545/run/003_relative_import.ts": "a1572e8fd2c2712b33f04aed2561505b5feb2c8696f1f2cded3de7127931b97e"
-  }
-}
diff --git a/tests/testdata/run/permission_request_no_prompt.ts b/tests/testdata/run/permission_request_no_prompt.ts
new file mode 100644
index 0000000000..e33ffe3ce8
--- /dev/null
+++ b/tests/testdata/run/permission_request_no_prompt.ts
@@ -0,0 +1 @@
+console.log(await Deno.permissions.request({ name: "read" }));
diff --git a/tests/testdata/run/type_directives_02.ts b/tests/testdata/run/type_directives_02.ts
deleted file mode 100644
index 0c59346e2b..0000000000
--- a/tests/testdata/run/type_directives_02.ts
+++ /dev/null
@@ -1,3 +0,0 @@
-import * as foo from "../subdir/type_reference.js";
-
-console.log(foo.foo);
diff --git a/tests/testdata/run/type_directives_02.ts.out b/tests/testdata/run/type_directives_02.ts.out
deleted file mode 100644
index b064483b41..0000000000
--- a/tests/testdata/run/type_directives_02.ts.out
+++ /dev/null
@@ -1,3 +0,0 @@
-[WILDCARD]
-DEBUG TS - host.getSourceFile("file:///[WILDCARD]/subdir/type_reference.d.ts", Latest)
-[WILDCARD]
\ No newline at end of file
diff --git a/tests/testdata/run/unhandled_rejection.ts.out b/tests/testdata/run/unhandled_rejection.ts.out
deleted file mode 100644
index 6ab1667dc1..0000000000
--- a/tests/testdata/run/unhandled_rejection.ts.out
+++ /dev/null
@@ -1,9 +0,0 @@
-[WILDCARD]
-unhandled rejection at: Promise {
-  <rejected> Error: bar not available
-    at new Foo (file:///[WILDCARD]/testdata/run/unhandled_rejection.ts:8:20)
-    at file:///[WILDCARD]/testdata/run/unhandled_rejection.ts:12:1
-} reason: Error: bar not available
-    at new Foo (file:///[WILDCARD]/testdata/run/unhandled_rejection.ts:8:20)
-    at file:///[WILDCARD]/testdata/run/unhandled_rejection.ts:12:1
-unhandled rejection at: Promise { <rejected> undefined } reason: undefined
diff --git a/tests/testdata/run/unhandled_rejection_sync_error.ts.out b/tests/testdata/run/unhandled_rejection_sync_error.ts.out
deleted file mode 100644
index e178373f03..0000000000
--- a/tests/testdata/run/unhandled_rejection_sync_error.ts.out
+++ /dev/null
@@ -1,6 +0,0 @@
-[WILDCARD]
-unhandled rejection at: Promise {
-  <rejected> Error: boom!
-    at file:///[WILDCARD]testdata/run/unhandled_rejection_sync_error.ts:6:7
-} reason: Error: boom!
-    at file:///[WILDCARD]testdata/run/unhandled_rejection_sync_error.ts:6:7
diff --git a/tests/testdata/run/warn_on_deprecated_api/main.js b/tests/testdata/run/warn_on_deprecated_api/main.js
deleted file mode 100644
index 8811df78de..0000000000
--- a/tests/testdata/run/warn_on_deprecated_api/main.js
+++ /dev/null
@@ -1,34 +0,0 @@
-import { runEcho as runEcho2 } from "http://localhost:4545/run/warn_on_deprecated_api/mod.ts";
-
-// @ts-ignore `Deno.run()` was soft-removed in Deno 2.
-const p = Deno.run({
-  cmd: [
-    Deno.execPath(),
-    "eval",
-    "console.log('hello world')",
-  ],
-});
-await p.status();
-p.close();
-
-async function runEcho() {
-  // @ts-ignore `Deno.run()` was soft-removed in Deno 2.
-  const p = Deno.run({
-    cmd: [
-      Deno.execPath(),
-      "eval",
-      "console.log('hello world')",
-    ],
-  });
-  await p.status();
-  p.close();
-}
-
-await runEcho();
-await runEcho();
-
-for (let i = 0; i < 10; i++) {
-  await runEcho();
-}
-
-await runEcho2();
diff --git a/tests/testdata/run/warn_on_deprecated_api/main.out b/tests/testdata/run/warn_on_deprecated_api/main.out
deleted file mode 100644
index ef85a6f99b..0000000000
--- a/tests/testdata/run/warn_on_deprecated_api/main.out
+++ /dev/null
@@ -1,15 +0,0 @@
-Download http://localhost:4545/run/warn_on_deprecated_api/mod.ts
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
diff --git a/tests/testdata/run/warn_on_deprecated_api/main.verbose.out b/tests/testdata/run/warn_on_deprecated_api/main.verbose.out
deleted file mode 100644
index e17562eef3..0000000000
--- a/tests/testdata/run/warn_on_deprecated_api/main.verbose.out
+++ /dev/null
@@ -1,60 +0,0 @@
-Download http://localhost:4545/run/warn_on_deprecated_api/mod.ts
-
-See the Deno 1 to 2 Migration Guide for more information at https://docs.deno.com/runtime/manual/advanced/migrate_deprecations
-
-Stack trace:
-  at [WILDCARD]warn_on_deprecated_api/main.js:3:16
-
-hint: Use "Deno.Command()" API instead.
-
-hello world
-
-See the Deno 1 to 2 Migration Guide for more information at https://docs.deno.com/runtime/manual/advanced/migrate_deprecations
-
-Stack trace:
-  at runEcho ([WILDCARD]warn_on_deprecated_api/main.js:14:18)
-  at [WILDCARD]warn_on_deprecated_api/main.js:25:7
-
-hint: Use "Deno.Command()" API instead.
-
-hello world
-
-See the Deno 1 to 2 Migration Guide for more information at https://docs.deno.com/runtime/manual/advanced/migrate_deprecations
-
-Stack trace:
-  at runEcho ([WILDCARD]warn_on_deprecated_api/main.js:14:18)
-  at [WILDCARD]warn_on_deprecated_api/main.js:26:7
-
-hint: Use "Deno.Command()" API instead.
-
-hello world
-
-See the Deno 1 to 2 Migration Guide for more information at https://docs.deno.com/runtime/manual/advanced/migrate_deprecations
-
-Stack trace:
-  at runEcho ([WILDCARD]warn_on_deprecated_api/main.js:14:18)
-  at [WILDCARD]warn_on_deprecated_api/main.js:29:9
-
-hint: Use "Deno.Command()" API instead.
-
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-
-See the Deno 1 to 2 Migration Guide for more information at https://docs.deno.com/runtime/manual/advanced/migrate_deprecations
-
-Stack trace:
-  at runEcho (http://localhost:4545/run/warn_on_deprecated_api/mod.ts:2:18)
-  at [WILDCARD]warn_on_deprecated_api/main.js:32:7
-
-hint: Use "Deno.Command()" API instead.
-hint: It appears this API is used by a remote dependency. Try upgrading to the latest version of that dependency.
-
-hello world
diff --git a/tests/testdata/run/warn_on_deprecated_api/main_disabled_env.out b/tests/testdata/run/warn_on_deprecated_api/main_disabled_env.out
deleted file mode 100644
index ef85a6f99b..0000000000
--- a/tests/testdata/run/warn_on_deprecated_api/main_disabled_env.out
+++ /dev/null
@@ -1,15 +0,0 @@
-Download http://localhost:4545/run/warn_on_deprecated_api/mod.ts
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
diff --git a/tests/testdata/run/warn_on_deprecated_api/main_disabled_flag.out b/tests/testdata/run/warn_on_deprecated_api/main_disabled_flag.out
deleted file mode 100644
index ce3755d166..0000000000
--- a/tests/testdata/run/warn_on_deprecated_api/main_disabled_flag.out
+++ /dev/null
@@ -1,14 +0,0 @@
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
-hello world
diff --git a/tests/testdata/run/warn_on_deprecated_api/mod.ts b/tests/testdata/run/warn_on_deprecated_api/mod.ts
deleted file mode 100644
index f74632b2cd..0000000000
--- a/tests/testdata/run/warn_on_deprecated_api/mod.ts
+++ /dev/null
@@ -1,11 +0,0 @@
-export async function runEcho() {
-  const p = Deno.run({
-    cmd: [
-      Deno.execPath(),
-      "eval",
-      "console.log('hello world')",
-    ],
-  });
-  await p.status();
-  p.close();
-}
diff --git a/tests/testdata/run/with_package_json/with_stop/main.out b/tests/testdata/run/with_package_json/with_stop/main.out
deleted file mode 100644
index 44098a2d86..0000000000
--- a/tests/testdata/run/with_package_json/with_stop/main.out
+++ /dev/null
@@ -1,5 +0,0 @@
-[WILDCARD]Config file found at '[WILDCARD]with_package_json[WILDCARD]with_stop[WILDCARD]some[WILDCARD]nested[WILDCARD]deno.json'
-[WILDCARD]
-error: Relative import path "chalk" not prefixed with / or ./ or ../
-  hint: If you want to use a JSR or npm package, try running `deno add jsr:chalk` or `deno add npm:chalk`
-    at file:///[WILDCARD]with_package_json/with_stop/some/nested/dir/main.ts:3:19
diff --git a/tests/testdata/task/package_json_node_modules_dir_false/bin.out b/tests/testdata/task/package_json_node_modules_dir_false/bin.out
deleted file mode 100644
index d5d59d5515..0000000000
--- a/tests/testdata/task/package_json_node_modules_dir_false/bin.out
+++ /dev/null
@@ -1,2 +0,0 @@
-Task echo deno eval 'console.log(1)'
-1
diff --git a/tests/testdata/task/package_json_node_modules_dir_false/deno.json b/tests/testdata/task/package_json_node_modules_dir_false/deno.json
deleted file mode 100644
index 23a325cfc2..0000000000
--- a/tests/testdata/task/package_json_node_modules_dir_false/deno.json
+++ /dev/null
@@ -1,3 +0,0 @@
-{
-  "nodeModulesDir": false
-}
diff --git a/tests/unit/command_test.ts b/tests/unit/command_test.ts
index 51bbdd8600..8345548f85 100644
--- a/tests/unit/command_test.ts
+++ b/tests/unit/command_test.ts
@@ -14,27 +14,31 @@ Deno.test(
     const enc = new TextEncoder();
     const cwd = await Deno.makeTempDir({ prefix: "deno_command_test" });
 
+    const exitCodeFileLock = "deno_was_here.lock";
     const exitCodeFile = "deno_was_here";
     const programFile = "poll_exit.ts";
     const program = `
+const file = await Deno.open("${exitCodeFileLock}", { write: true, create: true });
 async function tryExit() {
+  await file.lock(true);
   try {
     const code = parseInt(await Deno.readTextFile("${exitCodeFile}"));
     Deno.exit(code);
   } catch {
     // Retry if we got here before deno wrote the file.
     setTimeout(tryExit, 0.01);
+  } finally {
+    await file.unlock();
   }
 }
 
 tryExit();
 `;
-
     Deno.writeFileSync(`${cwd}/${programFile}`, enc.encode(program));
 
     const command = new Deno.Command(Deno.execPath(), {
       cwd,
-      args: ["run", "--allow-read", programFile],
+      args: ["run", "-RW", programFile],
       stdout: "inherit",
       stderr: "inherit",
     });
@@ -43,12 +47,18 @@ tryExit();
     // Write the expected exit code *after* starting deno.
     // This is how we verify that `Child` is actually asynchronous.
     const code = 84;
-    Deno.writeFileSync(`${cwd}/${exitCodeFile}`, enc.encode(`${code}`));
 
+    await using file = await Deno.open(`${cwd}/${exitCodeFileLock}`, {
+      write: true,
+      create: true,
+    });
+    await file.lock(true);
+    Deno.writeFileSync(`${cwd}/${exitCodeFile}`, enc.encode(`${code}`));
+    await file.unlock();
     const status = await child.status;
     await Deno.remove(cwd, { recursive: true });
-    assertEquals(status.success, false);
     assertEquals(status.code, code);
+    assertEquals(status.success, false);
     assertEquals(status.signal, null);
   },
 );
diff --git a/tests/unit/console_test.ts b/tests/unit/console_test.ts
index 201d18f004..06f5dd7e61 100644
--- a/tests/unit/console_test.ts
+++ b/tests/unit/console_test.ts
@@ -1162,7 +1162,7 @@ Deno.test(function consoleTestWithIntegerFormatSpecifier() {
   assertEquals(stringify("%i"), "%i");
   assertEquals(stringify("%i", 42.0), "42");
   assertEquals(stringify("%i", 42), "42");
-  assertEquals(stringify("%i", "42"), "NaN");
+  assertEquals(stringify("%i", "42"), "42");
   assertEquals(stringify("%i", 1.5), "1");
   assertEquals(stringify("%i", -0.5), "0");
   assertEquals(stringify("%i", ""), "NaN");
@@ -1172,7 +1172,7 @@ Deno.test(function consoleTestWithIntegerFormatSpecifier() {
   assertEquals(stringify("%d", 12345678901234567890123), "1");
   assertEquals(
     stringify("%i", 12345678901234567890123n),
-    "12345678901234567890123n",
+    "1.2345678901234568e+22",
   );
 });
 
@@ -1180,13 +1180,13 @@ Deno.test(function consoleTestWithFloatFormatSpecifier() {
   assertEquals(stringify("%f"), "%f");
   assertEquals(stringify("%f", 42.0), "42");
   assertEquals(stringify("%f", 42), "42");
-  assertEquals(stringify("%f", "42"), "NaN");
+  assertEquals(stringify("%f", "42"), "42");
   assertEquals(stringify("%f", 1.5), "1.5");
   assertEquals(stringify("%f", -0.5), "-0.5");
   assertEquals(stringify("%f", Math.PI), "3.141592653589793");
   assertEquals(stringify("%f", ""), "NaN");
   assertEquals(stringify("%f", Symbol("foo")), "NaN");
-  assertEquals(stringify("%f", 5n), "NaN");
+  assertEquals(stringify("%f", 5n), "5");
   assertEquals(stringify("%f %f", 42, 43), "42 43");
   assertEquals(stringify("%f %f", 42), "42 %f");
 });
@@ -1227,6 +1227,7 @@ Deno.test(function consoleParseCssColor() {
   assertEquals(parseCssColor("inherit"), null);
   assertEquals(parseCssColor("black"), [0, 0, 0]);
   assertEquals(parseCssColor("darkmagenta"), [139, 0, 139]);
+  assertEquals(parseCssColor("darkMaGenta"), [139, 0, 139]);
   assertEquals(parseCssColor("slateblue"), [106, 90, 205]);
   assertEquals(parseCssColor("#ffaa00"), [255, 170, 0]);
   assertEquals(parseCssColor("#ffAA00"), [255, 170, 0]);
@@ -1913,6 +1914,21 @@ Deno.test(function consoleLogWhenCauseIsAssignedShouldNotPrintCauseTwice() {
   });
 });
 
+Deno.test(function consoleLogCauseNotFilteredOnNonError() {
+  mockConsole((console, out) => {
+    const foo = {
+      a: 1,
+      b: 2,
+      cause: 3,
+    };
+    console.log(foo);
+
+    const result = stripAnsiCode(out.toString());
+    const expected = "{ a: 1, b: 2, cause: 3 }\n";
+    assertEquals(result.trim(), expected.trim());
+  });
+});
+
 // console.log(new Proxy(new RegExp(), {}))
 Deno.test(function consoleLogShouldNotThrowErrorWhenInputIsProxiedRegExp() {
   mockConsole((console, out) => {
diff --git a/tests/unit/globals_test.ts b/tests/unit/globals_test.ts
index 45a0458357..6de228e1c9 100644
--- a/tests/unit/globals_test.ts
+++ b/tests/unit/globals_test.ts
@@ -1,4 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+// deno-lint-ignore-file no-node-globals
 
 import {
   assert,
diff --git a/tests/unit/permissions_test.ts b/tests/unit/permissions_test.ts
index 82524d556c..f981b10fd6 100644
--- a/tests/unit/permissions_test.ts
+++ b/tests/unit/permissions_test.ts
@@ -20,54 +20,72 @@ Deno.test(function permissionInvalidNameSync() {
   }, TypeError);
 });
 
-Deno.test(async function permissionNetInvalidHost() {
-  await assertRejects(async () => {
-    await Deno.permissions.query({ name: "net", host: ":" });
-  }, URIError);
-});
+Deno.test(
+  { permissions: { net: [] } },
+  async function permissionNetInvalidHost() {
+    await assertRejects(async () => {
+      await Deno.permissions.query({ name: "net", host: ":" });
+    }, URIError);
+  },
+);
 
-Deno.test(function permissionNetInvalidHostSync() {
-  assertThrows(() => {
-    Deno.permissions.querySync({ name: "net", host: ":" });
-  }, URIError);
-});
+Deno.test(
+  { permissions: { net: [] } },
+  function permissionNetInvalidHostSync() {
+    assertThrows(() => {
+      Deno.permissions.querySync({ name: "net", host: ":" });
+    }, URIError);
+  },
+);
 
-Deno.test(async function permissionSysValidKind() {
-  await Deno.permissions.query({ name: "sys", kind: "loadavg" });
-  await Deno.permissions.query({ name: "sys", kind: "osRelease" });
-  await Deno.permissions.query({ name: "sys", kind: "osUptime" });
-  await Deno.permissions.query({ name: "sys", kind: "networkInterfaces" });
-  await Deno.permissions.query({ name: "sys", kind: "systemMemoryInfo" });
-  await Deno.permissions.query({ name: "sys", kind: "hostname" });
-  await Deno.permissions.query({ name: "sys", kind: "uid" });
-  await Deno.permissions.query({ name: "sys", kind: "gid" });
-  await Deno.permissions.query({ name: "sys", kind: "cpus" });
-});
+Deno.test(
+  { permissions: { sys: [] } },
+  async function permissionSysValidKind() {
+    await Deno.permissions.query({ name: "sys", kind: "loadavg" });
+    await Deno.permissions.query({ name: "sys", kind: "osRelease" });
+    await Deno.permissions.query({ name: "sys", kind: "osUptime" });
+    await Deno.permissions.query({ name: "sys", kind: "networkInterfaces" });
+    await Deno.permissions.query({ name: "sys", kind: "systemMemoryInfo" });
+    await Deno.permissions.query({ name: "sys", kind: "hostname" });
+    await Deno.permissions.query({ name: "sys", kind: "uid" });
+    await Deno.permissions.query({ name: "sys", kind: "gid" });
+    await Deno.permissions.query({ name: "sys", kind: "cpus" });
+  },
+);
 
-Deno.test(function permissionSysValidKindSync() {
-  Deno.permissions.querySync({ name: "sys", kind: "loadavg" });
-  Deno.permissions.querySync({ name: "sys", kind: "osRelease" });
-  Deno.permissions.querySync({ name: "sys", kind: "networkInterfaces" });
-  Deno.permissions.querySync({ name: "sys", kind: "systemMemoryInfo" });
-  Deno.permissions.querySync({ name: "sys", kind: "hostname" });
-  Deno.permissions.querySync({ name: "sys", kind: "uid" });
-  Deno.permissions.querySync({ name: "sys", kind: "gid" });
-  Deno.permissions.querySync({ name: "sys", kind: "cpus" });
-});
+Deno.test(
+  { permissions: { sys: [] } },
+  function permissionSysValidKindSync() {
+    Deno.permissions.querySync({ name: "sys", kind: "loadavg" });
+    Deno.permissions.querySync({ name: "sys", kind: "osRelease" });
+    Deno.permissions.querySync({ name: "sys", kind: "networkInterfaces" });
+    Deno.permissions.querySync({ name: "sys", kind: "systemMemoryInfo" });
+    Deno.permissions.querySync({ name: "sys", kind: "hostname" });
+    Deno.permissions.querySync({ name: "sys", kind: "uid" });
+    Deno.permissions.querySync({ name: "sys", kind: "gid" });
+    Deno.permissions.querySync({ name: "sys", kind: "cpus" });
+  },
+);
 
-Deno.test(async function permissionSysInvalidKind() {
-  await assertRejects(async () => {
-    // deno-lint-ignore no-explicit-any
-    await Deno.permissions.query({ name: "sys", kind: "abc" as any });
-  }, TypeError);
-});
+Deno.test(
+  { permissions: { sys: [] } },
+  async function permissionSysInvalidKind() {
+    await assertRejects(async () => {
+      // deno-lint-ignore no-explicit-any
+      await Deno.permissions.query({ name: "sys", kind: "abc" as any });
+    }, TypeError);
+  },
+);
 
-Deno.test(function permissionSysInvalidKindSync() {
-  assertThrows(() => {
-    // deno-lint-ignore no-explicit-any
-    Deno.permissions.querySync({ name: "sys", kind: "abc" as any });
-  }, TypeError);
-});
+Deno.test(
+  { permissions: { sys: [] } },
+  function permissionSysInvalidKindSync() {
+    assertThrows(() => {
+      // deno-lint-ignore no-explicit-any
+      Deno.permissions.querySync({ name: "sys", kind: "abc" as any });
+    }, TypeError);
+  },
+);
 
 Deno.test(async function permissionQueryReturnsEventTarget() {
   const status = await Deno.permissions.query({ name: "read", path: "." });
@@ -134,29 +152,35 @@ Deno.test(function permissionStatusIllegalConstructor() {
 });
 
 // Regression test for https://github.com/denoland/deno/issues/17020
-Deno.test(async function permissionURL() {
-  const path = new URL(".", import.meta.url);
+Deno.test(
+  { permissions: { read: [], write: [], ffi: [], run: [] } },
+  async function permissionURL() {
+    const path = new URL(".", import.meta.url);
 
-  await Deno.permissions.query({ name: "read", path });
-  await Deno.permissions.query({ name: "write", path });
-  await Deno.permissions.query({ name: "ffi", path });
-  await Deno.permissions.query({ name: "run", command: path });
-});
+    await Deno.permissions.query({ name: "read", path });
+    await Deno.permissions.query({ name: "write", path });
+    await Deno.permissions.query({ name: "ffi", path });
+    await Deno.permissions.query({ name: "run", command: path });
+  },
+);
 
-Deno.test(function permissionURLSync() {
-  Deno.permissions.querySync({
-    name: "read",
-    path: new URL(".", import.meta.url),
-  });
-  Deno.permissions.querySync({
-    name: "write",
-    path: new URL(".", import.meta.url),
-  });
-  Deno.permissions.querySync({
-    name: "run",
-    command: new URL(".", import.meta.url),
-  });
-});
+Deno.test(
+  { permissions: { read: [], write: [], ffi: [], run: [] } },
+  function permissionURLSync() {
+    Deno.permissions.querySync({
+      name: "read",
+      path: new URL(".", import.meta.url),
+    });
+    Deno.permissions.querySync({
+      name: "write",
+      path: new URL(".", import.meta.url),
+    });
+    Deno.permissions.querySync({
+      name: "run",
+      command: new URL(".", import.meta.url),
+    });
+  },
+);
 
 Deno.test(async function permissionDescriptorValidation() {
   for (const value of [undefined, null, {}]) {
diff --git a/tests/unit/serve_test.ts b/tests/unit/serve_test.ts
index 439d71d553..7d8c6ca06d 100644
--- a/tests/unit/serve_test.ts
+++ b/tests/unit/serve_test.ts
@@ -4270,3 +4270,60 @@ Deno.test({
   assertEquals(hostname, "0.0.0.0");
   await server.shutdown();
 });
+
+Deno.test({
+  name: "AbortSignal aborted when request is cancelled",
+}, async () => {
+  const { promise, resolve } = Promise.withResolvers<void>();
+
+  let cancelled = false;
+
+  const server = Deno.serve({
+    hostname: "0.0.0.0",
+    port: servePort,
+    onListen: () => resolve(),
+  }, async (request) => {
+    request.signal.addEventListener("abort", () => cancelled = true);
+    assert(!request.signal.aborted);
+    await new Promise((resolve) => setTimeout(resolve, 3000)); // abort during waiting
+    assert(request.signal.aborted);
+    return new Response("Ok");
+  });
+
+  await promise;
+  await fetch(`http://localhost:${servePort}/`, {
+    signal: AbortSignal.timeout(1000),
+  }).catch(() => {});
+
+  await server.shutdown();
+
+  assert(cancelled);
+});
+
+Deno.test({
+  name: "AbortSignal event aborted when request is cancelled",
+}, async () => {
+  const { promise, resolve } = Promise.withResolvers<void>();
+
+  const server = Deno.serve({
+    hostname: "0.0.0.0",
+    port: servePort,
+    onListen: () => resolve(),
+  }, async (request) => {
+    const { promise: promiseAbort, resolve: resolveAbort } = Promise
+      .withResolvers<void>();
+    request.signal.addEventListener("abort", () => resolveAbort());
+    assert(!request.signal.aborted);
+
+    await promiseAbort;
+
+    return new Response("Ok");
+  });
+
+  await promise;
+  await fetch(`http://localhost:${servePort}/`, {
+    signal: AbortSignal.timeout(100),
+  }).catch(() => {});
+
+  await server.shutdown();
+});
diff --git a/tests/unit/signal_test.ts b/tests/unit/signal_test.ts
index 65b5ba78e1..8923aa75bf 100644
--- a/tests/unit/signal_test.ts
+++ b/tests/unit/signal_test.ts
@@ -5,101 +5,101 @@ Deno.test(
   { ignore: Deno.build.os !== "windows" },
   function signalsNotImplemented() {
     const msg =
-      "Windows only supports ctrl-c (SIGINT) and ctrl-break (SIGBREAK).";
+      "Windows only supports ctrl-c (SIGINT) and ctrl-break (SIGBREAK), but got ";
     assertThrows(
       () => {
         Deno.addSignalListener("SIGALRM", () => {});
       },
       Error,
-      msg,
+      msg + "SIGALRM",
     );
     assertThrows(
       () => {
         Deno.addSignalListener("SIGCHLD", () => {});
       },
       Error,
-      msg,
+      msg + "SIGCHLD",
     );
     assertThrows(
       () => {
         Deno.addSignalListener("SIGHUP", () => {});
       },
       Error,
-      msg,
+      msg + "SIGHUP",
     );
     assertThrows(
       () => {
         Deno.addSignalListener("SIGIO", () => {});
       },
       Error,
-      msg,
+      msg + "SIGIO",
     );
     assertThrows(
       () => {
         Deno.addSignalListener("SIGPIPE", () => {});
       },
       Error,
-      msg,
+      msg + "SIGPIPE",
     );
     assertThrows(
       () => {
         Deno.addSignalListener("SIGQUIT", () => {});
       },
       Error,
-      msg,
+      msg + "SIGQUIT",
     );
     assertThrows(
       () => {
         Deno.addSignalListener("SIGTERM", () => {});
       },
       Error,
-      msg,
+      msg + "SIGTERM",
     );
     assertThrows(
       () => {
         Deno.addSignalListener("SIGUSR1", () => {});
       },
       Error,
-      msg,
+      msg + "SIGUSR1",
     );
     assertThrows(
       () => {
         Deno.addSignalListener("SIGUSR2", () => {});
       },
       Error,
-      msg,
+      msg + "SIGUSR2",
     );
     assertThrows(
       () => {
         Deno.addSignalListener("SIGWINCH", () => {});
       },
       Error,
-      msg,
+      msg + "SIGWINCH",
     );
     assertThrows(
       () => Deno.addSignalListener("SIGKILL", () => {}),
       Error,
-      msg,
+      msg + "SIGKILL",
     );
     assertThrows(
       () => Deno.addSignalListener("SIGSTOP", () => {}),
       Error,
-      msg,
+      msg + "SIGSTOP",
     );
     assertThrows(
       () => Deno.addSignalListener("SIGILL", () => {}),
       Error,
-      msg,
+      msg + "SIGILL",
     );
     assertThrows(
       () => Deno.addSignalListener("SIGFPE", () => {}),
       Error,
-      msg,
+      msg + "SIGFPE",
     );
     assertThrows(
       () => Deno.addSignalListener("SIGSEGV", () => {}),
       Error,
-      msg,
+      msg + "SIGSEGV",
     );
   },
 );
diff --git a/tests/unit/stat_test.ts b/tests/unit/stat_test.ts
index 59831a069f..0609035b41 100644
--- a/tests/unit/stat_test.ts
+++ b/tests/unit/stat_test.ts
@@ -31,6 +31,13 @@ Deno.test(
     assert(
       tempInfo.birthtime === null || now - tempInfo.birthtime.valueOf() < 1000,
     );
+    assert(tempInfo.ctime !== null && now - tempInfo.ctime.valueOf() < 1000);
+    const mode = tempInfo.mode! & 0o777;
+    if (Deno.build.os === "windows") {
+      assertEquals(mode, 0o666);
+    } else {
+      assertEquals(mode, 0o600);
+    }
 
     const readmeInfoByUrl = Deno.statSync(pathToAbsoluteFileUrl("README.md"));
     assert(readmeInfoByUrl.isFile);
@@ -65,6 +72,10 @@ Deno.test(
       tempInfoByUrl.birthtime === null ||
         now - tempInfoByUrl.birthtime.valueOf() < 1000,
     );
+    assert(
+      tempInfoByUrl.ctime !== null &&
+        now - tempInfoByUrl.ctime.valueOf() < 1000,
+    );
 
     Deno.removeSync(tempFile, { recursive: true });
     Deno.removeSync(tempFileForUrl, { recursive: true });
@@ -171,6 +182,7 @@ Deno.test(
     assert(
       tempInfo.birthtime === null || now - tempInfo.birthtime.valueOf() < 1000,
     );
+    assert(tempInfo.ctime !== null && now - tempInfo.ctime.valueOf() < 1000);
 
     const tempFileForUrl = await Deno.makeTempFile();
     const tempInfoByUrl = await Deno.stat(
@@ -191,7 +203,10 @@ Deno.test(
       tempInfoByUrl.birthtime === null ||
         now - tempInfoByUrl.birthtime.valueOf() < 1000,
     );
-
+    assert(
+      tempInfoByUrl.ctime !== null &&
+        now - tempInfoByUrl.ctime.valueOf() < 1000,
+    );
     Deno.removeSync(tempFile, { recursive: true });
     Deno.removeSync(tempFileForUrl, { recursive: true });
   },
@@ -271,7 +286,6 @@ Deno.test(
     const s = Deno.statSync(filename);
     assert(s.dev !== 0);
     assert(s.ino === null);
-    assert(s.mode === null);
     assert(s.nlink === null);
     assert(s.uid === null);
     assert(s.gid === null);
diff --git a/tests/unit/urlpattern_test.ts b/tests/unit/urlpattern_test.ts
index 65c2241737..3c1fb0cf19 100644
--- a/tests/unit/urlpattern_test.ts
+++ b/tests/unit/urlpattern_test.ts
@@ -63,9 +63,3 @@ Deno.test(function urlPatternWithPrototypePollution() {
     RegExp.prototype.exec = originalExec;
   }
 });
-
-Deno.test(function urlPatternEmptyFallback() {
-  const p = new URLPattern({ pathname: "/foo/bar{/:qaz}?" });
-  const match = p.exec("https://example.com/foo/bar");
-  assertEquals(match!.pathname.groups.qaz, "");
-});
diff --git a/tests/unit/webcrypto_test.ts b/tests/unit/webcrypto_test.ts
index 57aa19eaee..09552a0587 100644
--- a/tests/unit/webcrypto_test.ts
+++ b/tests/unit/webcrypto_test.ts
@@ -2045,3 +2045,43 @@ Deno.test(async function p521Generate() {
   assert(key.privateKey instanceof CryptoKey);
   assert(key.publicKey instanceof CryptoKey);
 });
+
+Deno.test(async function x25519SharedSecret() {
+  const alicesKeyPair = await crypto.subtle.generateKey(
+    {
+      name: "X25519",
+    },
+    false,
+    ["deriveBits"],
+  ) as CryptoKeyPair;
+
+  const bobsKeyPair = await crypto.subtle.generateKey(
+    {
+      name: "X25519",
+    },
+    false,
+    ["deriveBits"],
+  ) as CryptoKeyPair;
+
+  const sharedSecret1 = await crypto.subtle.deriveBits(
+    {
+      name: "X25519",
+      public: bobsKeyPair.publicKey,
+    },
+    alicesKeyPair.privateKey,
+    128,
+  );
+
+  const sharedSecret2 = await crypto.subtle.deriveBits(
+    {
+      name: "X25519",
+      public: alicesKeyPair.publicKey,
+    },
+    bobsKeyPair.privateKey,
+    128,
+  );
+
+  assertEquals(sharedSecret1.byteLength, sharedSecret2.byteLength);
+  assertEquals(sharedSecret1.byteLength, 16);
+  assertEquals(new Uint8Array(sharedSecret1), new Uint8Array(sharedSecret2));
+});
diff --git a/tests/unit/websocket_test.ts b/tests/unit/websocket_test.ts
index 7db876b177..3aafe8da22 100644
--- a/tests/unit/websocket_test.ts
+++ b/tests/unit/websocket_test.ts
@@ -453,7 +453,8 @@ Deno.test("invalid server", async () => {
   const { promise, resolve } = Promise.withResolvers<void>();
   const ws = new WebSocket("ws://localhost:2121");
   let err = false;
-  ws.onerror = () => {
+  ws.onerror = (e) => {
+    assert("error" in e);
     err = true;
   };
   ws.onclose = () => {
diff --git a/tests/unit/webstorage_test.ts b/tests/unit/webstorage_test.ts
index 9dc560af1b..aa832b1c4b 100644
--- a/tests/unit/webstorage_test.ts
+++ b/tests/unit/webstorage_test.ts
@@ -50,3 +50,8 @@ Deno.test(function webstorageProxy() {
   assertEquals(localStorage[symbol as any], "bar");
   assertEquals(symbol in localStorage, true);
 });
+
+Deno.test(function webstorageGetOwnPropertyDescriptorSymbol() {
+  localStorage.clear();
+  Object.getOwnPropertyDescriptor(localStorage, Symbol("foo"));
+});
diff --git a/tests/unit_node/_fs/_fs_stat_test.ts b/tests/unit_node/_fs/_fs_stat_test.ts
index 02c620e2dc..e42aa34a9a 100644
--- a/tests/unit_node/_fs/_fs_stat_test.ts
+++ b/tests/unit_node/_fs/_fs_stat_test.ts
@@ -18,9 +18,11 @@ export function assertStats(actual: Stats, expected: Deno.FileInfo) {
   assertEquals(actual.atime?.getTime(), expected.atime?.getTime());
   assertEquals(actual.mtime?.getTime(), expected.mtime?.getTime());
   assertEquals(actual.birthtime?.getTime(), expected.birthtime?.getTime());
+  assertEquals(actual.ctime?.getTime(), expected.ctime?.getTime());
   assertEquals(actual.atimeMs ?? undefined, expected.atime?.getTime());
   assertEquals(actual.mtimeMs ?? undefined, expected.mtime?.getTime());
   assertEquals(actual.birthtimeMs ?? undefined, expected.birthtime?.getTime());
+  assertEquals(actual.ctimeMs ?? undefined, expected.ctime?.getTime());
   assertEquals(actual.isFile(), expected.isFile);
   assertEquals(actual.isDirectory(), expected.isDirectory);
   assertEquals(actual.isSymbolicLink(), expected.isSymlink);
@@ -49,6 +51,7 @@ export function assertStatsBigInt(
   assertEquals(actual.atime?.getTime(), expected.atime?.getTime());
   assertEquals(actual.mtime?.getTime(), expected.mtime?.getTime());
   assertEquals(actual.birthtime?.getTime(), expected.birthtime?.getTime());
+  assertEquals(actual.ctime?.getTime(), expected.ctime?.getTime());
   assertEquals(
     actual.atimeMs === null ? undefined : Number(actual.atimeMs),
     expected.atime?.getTime(),
@@ -61,6 +64,10 @@ export function assertStatsBigInt(
     actual.birthtimeMs === null ? undefined : Number(actual.birthtimeMs),
     expected.birthtime?.getTime(),
   );
+  assertEquals(
+    actual.ctimeMs === null ? undefined : Number(actual.ctimeMs),
+    expected.ctime?.getTime(),
+  );
   assertEquals(actual.atimeNs === null, actual.atime === null);
   assertEquals(actual.mtimeNs === null, actual.mtime === null);
   assertEquals(actual.birthtimeNs === null, actual.birthtime === null);
diff --git a/tests/unit_node/child_process_test.ts b/tests/unit_node/child_process_test.ts
index f776fa4acd..0ea3c46cf0 100644
--- a/tests/unit_node/child_process_test.ts
+++ b/tests/unit_node/child_process_test.ts
@@ -1045,3 +1045,19 @@ Deno.test(async function sendAfterClosedThrows() {
 
   await timeout.promise;
 });
+
+Deno.test(async function noWarningsFlag() {
+  const code = ``;
+  const file = await Deno.makeTempFile();
+  await Deno.writeTextFile(file, code);
+  const timeout = withTimeout<void>();
+  const child = CP.fork(file, [], {
+    execArgv: ["--no-warnings"],
+    stdio: ["inherit", "inherit", "inherit", "ipc"],
+  });
+  child.on("close", () => {
+    timeout.resolve();
+  });
+
+  await timeout.promise;
+});
diff --git a/tests/unit_node/crypto/crypto_key_test.ts b/tests/unit_node/crypto/crypto_key_test.ts
index 7995ce5d3f..3c7ad44232 100644
--- a/tests/unit_node/crypto/crypto_key_test.ts
+++ b/tests/unit_node/crypto/crypto_key_test.ts
@@ -656,3 +656,24 @@ z6TExWlQMjt66nV7R8cRAkzmABrG+NW3e8Zpac7Lkuv+zu0S+K7c
   assertEquals(publicKey.type, "public");
   assertEquals(publicKey.asymmetricKeyType, "rsa");
 });
+
+// https://github.com/denoland/deno/issues/26188
+Deno.test("generateKeyPair large pem", function () {
+  const passphrase = "mypassphrase";
+  const cipher = "aes-256-cbc";
+  const modulusLength = 4096;
+
+  generateKeyPairSync("rsa", {
+    modulusLength,
+    publicKeyEncoding: {
+      type: "spki",
+      format: "pem",
+    },
+    privateKeyEncoding: {
+      type: "pkcs8",
+      format: "pem",
+      cipher,
+      passphrase,
+    },
+  });
+});
diff --git a/tests/unit_node/crypto/crypto_misc_test.ts b/tests/unit_node/crypto/crypto_misc_test.ts
index 47a48b1bf8..007009339d 100644
--- a/tests/unit_node/crypto/crypto_misc_test.ts
+++ b/tests/unit_node/crypto/crypto_misc_test.ts
@@ -1,5 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-import { randomFillSync, randomUUID } from "node:crypto";
+import { randomFillSync, randomUUID, timingSafeEqual } from "node:crypto";
+import { Buffer } from "node:buffer";
 import { assert, assertEquals } from "../../unit/test_util.ts";
 import { assertNotEquals } from "@std/assert";
 
@@ -28,3 +29,10 @@ Deno.test("[node/crypto.randomFillSync] array buffer view", () => {
   assertEquals(buf.subarray(0, 8), new Uint8Array(8));
   assertEquals(buf.subarray(24, 32), new Uint8Array(8));
 });
+
+Deno.test("[node/crypto.timingSafeEqual] compares equal Buffer with different byteOffset", () => {
+  const a = Buffer.from([212, 213]);
+  const b = Buffer.from([0, 0, 0, 0, 0, 0, 0, 0, 212, 213]).subarray(8);
+
+  assert(timingSafeEqual(a, b));
+});
diff --git a/tests/unit_node/fs_test.ts b/tests/unit_node/fs_test.ts
index b1f7c53e8d..631608d7cc 100644
--- a/tests/unit_node/fs_test.ts
+++ b/tests/unit_node/fs_test.ts
@@ -1,25 +1,32 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-import { assert, assertEquals, assertThrows } from "@std/assert";
+/// <reference lib="deno.ns" />
+import { assert, assertEquals, assertRejects, assertThrows } from "@std/assert";
 import { join } from "node:path";
 import { tmpdir } from "node:os";
 import {
+  closeSync,
   constants,
+  copyFileSync,
   createWriteStream,
   existsSync,
   lstatSync,
   mkdtempSync,
+  openSync,
   promises,
   readFileSync,
+  readSync,
   Stats,
   statSync,
   writeFileSync,
 } from "node:fs";
 import {
   constants as fsPromiseConstants,
+  copyFile,
   cp,
   FileHandle,
   open,
+  stat,
   writeFile,
 } from "node:fs/promises";
 import process from "node:process";
@@ -117,6 +124,48 @@ Deno.test(
   },
 );
 
+Deno.test(
+  "[node/fs statSync] throw error with path information",
+  () => {
+    const file = "non-exist-file";
+    const fileUrl = new URL(file, import.meta.url);
+
+    assertThrows(() => {
+      statSync(file);
+    }, "Error: ENOENT: no such file or directory, stat 'non-exist-file'");
+
+    assertThrows(() => {
+      statSync(fileUrl);
+    }, `Error: ENOENT: no such file or directory, stat '${fileUrl.pathname}'`);
+  },
+);
+
+Deno.test(
+  "[node/fs/promises stat] throw error with path information",
+  async () => {
+    const file = "non-exist-file";
+    const fileUrl = new URL(file, import.meta.url);
+
+    try {
+      await stat(file);
+    } catch (error: unknown) {
+      assertEquals(
+        `${error}`,
+        "Error: ENOENT: no such file or directory, stat 'non-exist-file'",
+      );
+    }
+
+    try {
+      await stat(fileUrl);
+    } catch (error: unknown) {
+      assertEquals(
+        `${error}`,
+        `Error: ENOENT: no such file or directory, stat '${fileUrl.pathname}'`,
+      );
+    }
+  },
+);
+
 Deno.test(
   "[node/fs/promises cp] copy file",
   async () => {
@@ -201,3 +250,40 @@ Deno.test(
     assertEquals(res, [0, 1, 2, 3, 4, 5]);
   },
 );
+
+Deno.test("[node/fs] readSync works", () => {
+  const fd = openSync("tests/testdata/assets/hello.txt", "r");
+  const buf = new Uint8Array(256);
+  const bytesRead = readSync(fd!, buf);
+  assertEquals(bytesRead, 12);
+  closeSync(fd!);
+});
+
+Deno.test("[node/fs] copyFile COPYFILE_EXCL works", async () => {
+  const dir = mkdtempSync(join(tmpdir(), "foo-"));
+  const src = join(dir, "src.txt");
+  const dest = join(dir, "dest.txt");
+  await writeFile(src, "");
+  await copyFile(src, dest, fsPromiseConstants.COPYFILE_EXCL);
+  assert(existsSync(dest));
+  await assertRejects(() =>
+    copyFile(src, dest, fsPromiseConstants.COPYFILE_EXCL)
+  );
+  const dest2 = join(dir, "dest2.txt");
+  copyFileSync(src, dest2, fsPromiseConstants.COPYFILE_EXCL);
+  assert(existsSync(dest2));
+  assertThrows(() =>
+    copyFileSync(src, dest2, fsPromiseConstants.COPYFILE_EXCL)
+  );
+});
+
+Deno.test("[node/fs] statSync throws ENOENT for invalid path containing colon in it", () => {
+  // deno-lint-ignore no-explicit-any
+  const err: any = assertThrows(() => {
+    // Note: Deno.stat throws ERROR_INVALID_NAME (os error 123) instead of
+    // ERROR_FILE_NOT_FOUND (os error 2) on windows. This case checks that
+    // ERROR_INVALID_NAME is mapped to ENOENT correctly on node compat layer.
+    statSync("jsr:@std/assert");
+  });
+  assertEquals(err.code, "ENOENT");
+});
diff --git a/tests/unit_node/http2_test.ts b/tests/unit_node/http2_test.ts
index 7473a487ad..c540c90f7e 100644
--- a/tests/unit_node/http2_test.ts
+++ b/tests/unit_node/http2_test.ts
@@ -10,6 +10,11 @@ import * as net from "node:net";
 import { assert, assertEquals } from "@std/assert";
 import { curlRequest } from "../unit/test_util.ts";
 
+// Increase the timeout for the auto select family to avoid flakiness
+net.setDefaultAutoSelectFamilyAttemptTimeout(
+  net.getDefaultAutoSelectFamilyAttemptTimeout() * 30,
+);
+
 for (const url of ["http://localhost:4246", "https://localhost:4247"]) {
   Deno.test(`[node/http2 client] ${url}`, {
     ignore: Deno.build.os === "windows",
diff --git a/tests/unit_node/http_test.ts b/tests/unit_node/http_test.ts
index f85b1466b5..2b3b8f509f 100644
--- a/tests/unit_node/http_test.ts
+++ b/tests/unit_node/http_test.ts
@@ -3,10 +3,14 @@
 // deno-lint-ignore-file no-console
 
 import EventEmitter from "node:events";
-import http, { type RequestOptions, type ServerResponse } from "node:http";
+import http, {
+  IncomingMessage,
+  type RequestOptions,
+  ServerResponse,
+} from "node:http";
 import url from "node:url";
 import https from "node:https";
-import net from "node:net";
+import net, { Socket } from "node:net";
 import fs from "node:fs";
 import { text } from "node:stream/consumers";
 
@@ -1143,6 +1147,34 @@ Deno.test("[node/http] ServerResponse appendHeader set-cookie", async () => {
   await promise;
 });
 
+Deno.test("[node/http] ServerResponse header names case insensitive", async () => {
+  const { promise, resolve } = Promise.withResolvers<void>();
+  const server = http.createServer((_req, res) => {
+    res.setHeader("Content-Length", "12345");
+    res.removeHeader("content-length");
+    assertEquals(res.getHeader("Content-Length"), undefined);
+    assert(!res.hasHeader("Content-Length"));
+    res.appendHeader("content-length", "12345");
+    res.removeHeader("Content-Length");
+    assertEquals(res.getHeader("content-length"), undefined);
+    assert(!res.hasHeader("content-length"));
+    res.end("Hello World");
+  });
+
+  server.listen(async () => {
+    const { port } = server.address() as { port: number };
+    const res = await fetch(`http://localhost:${port}`);
+    assertEquals(res.headers.get("Content-Length"), null);
+    assertEquals(res.headers.get("content-length"), null);
+    assertEquals(await res.text(), "Hello World");
+    server.close(() => {
+      resolve();
+    });
+  });
+
+  await promise;
+});
+
 Deno.test("[node/http] IncomingMessage override", () => {
   const req = new http.IncomingMessage(new net.Socket());
   // https://github.com/dougmoscrop/serverless-http/blob/3aaa6d0fe241109a8752efb011c242d249f32368/lib/request.js#L20-L30
@@ -1672,3 +1704,75 @@ Deno.test("[node/http] upgraded socket closes when the server closed without clo
   await clientSocketClosed.promise;
   await serverProcessClosed.promise;
 });
+
+// deno-lint-ignore require-await
+Deno.test("[node/http] ServerResponse.call()", async () => {
+  function Wrapper(this: unknown, req: IncomingMessage) {
+    ServerResponse.call(this, req);
+  }
+  Object.setPrototypeOf(Wrapper.prototype, ServerResponse.prototype);
+
+  // deno-lint-ignore no-explicit-any
+  const wrapper = new (Wrapper as any)(new IncomingMessage(new Socket()));
+
+  assert(wrapper instanceof ServerResponse);
+});
+
+Deno.test("[node/http] ServerResponse _header", async () => {
+  const { promise, resolve } = Promise.withResolvers<void>();
+  const server = http.createServer((_req, res) => {
+    assert(Object.hasOwn(res, "_header"));
+    res.end();
+  });
+
+  server.listen(async () => {
+    const { port } = server.address() as { port: number };
+    const res = await fetch(`http://localhost:${port}`);
+    await res.body?.cancel();
+    server.close(() => {
+      resolve();
+    });
+  });
+
+  await promise;
+});
+
+Deno.test("[node/http] ServerResponse connection", async () => {
+  const { promise, resolve } = Promise.withResolvers<void>();
+  const server = http.createServer((_req, res) => {
+    assert(Object.hasOwn(res, "connection"));
+    assert(res.connection instanceof Socket);
+    res.end();
+  });
+
+  server.listen(async () => {
+    const { port } = server.address() as { port: number };
+    const res = await fetch(`http://localhost:${port}`);
+    await res.body?.cancel();
+    server.close(() => {
+      resolve();
+    });
+  });
+
+  await promise;
+});
+
+Deno.test("[node/http] ServerResponse socket", async () => {
+  const { promise, resolve } = Promise.withResolvers<void>();
+  const server = http.createServer((_req, res) => {
+    assert(Object.hasOwn(res, "socket"));
+    assert(res.socket instanceof Socket);
+    res.end();
+  });
+
+  server.listen(async () => {
+    const { port } = server.address() as { port: number };
+    const res = await fetch(`http://localhost:${port}`);
+    await res.body?.cancel();
+    server.close(() => {
+      resolve();
+    });
+  });
+
+  await promise;
+});
diff --git a/tests/unit_node/perf_hooks_test.ts b/tests/unit_node/perf_hooks_test.ts
index d5b9000410..8247f9fd3a 100644
--- a/tests/unit_node/perf_hooks_test.ts
+++ b/tests/unit_node/perf_hooks_test.ts
@@ -1,6 +1,10 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 import * as perfHooks from "node:perf_hooks";
-import { performance, PerformanceObserver } from "node:perf_hooks";
+import {
+  monitorEventLoopDelay,
+  performance,
+  PerformanceObserver,
+} from "node:perf_hooks";
 import { assertEquals, assertThrows } from "@std/assert";
 
 Deno.test({
@@ -68,3 +72,12 @@ Deno.test("[perf_hooks]: eventLoopUtilization", () => {
   assertEquals(typeof obj.active, "number");
   assertEquals(typeof obj.utilization, "number");
 });
+
+Deno.test("[perf_hooks]: monitorEventLoopDelay", () => {
+  const e = assertThrows(() => {
+    monitorEventLoopDelay({ resolution: 1 });
+  });
+
+  // deno-lint-ignore no-explicit-any
+  assertEquals((e as any).code, "ERR_NOT_IMPLEMENTED");
+});
diff --git a/tests/unit_node/process_test.ts b/tests/unit_node/process_test.ts
index add9e1280a..49de2dce1d 100644
--- a/tests/unit_node/process_test.ts
+++ b/tests/unit_node/process_test.ts
@@ -25,7 +25,6 @@ import {
   assertThrows,
   fail,
 } from "@std/assert";
-import { assertSpyCall, assertSpyCalls, spy } from "@std/testing/mock";
 import { stripAnsiCode } from "@std/fmt/colors";
 import * as path from "@std/path";
 import { delay } from "@std/async/delay";
@@ -239,33 +238,6 @@ Deno.test({
   },
 });
 
-Deno.test({
-  name: "process.on - ignored signals on windows",
-  ignore: Deno.build.os !== "windows",
-  fn() {
-    const ignoredSignals = ["SIGHUP", "SIGUSR1", "SIGUSR2"];
-
-    for (const signal of ignoredSignals) {
-      using consoleSpy = spy(console, "warn");
-      const handler = () => {};
-      process.on(signal, handler);
-      process.off(signal, handler);
-      assertSpyCall(consoleSpy, 0, {
-        args: [`Ignoring signal "${signal}" on Windows`],
-      });
-    }
-
-    {
-      using consoleSpy = spy(console, "warn");
-      const handler = () => {};
-      process.on("SIGTERM", handler);
-      process.off("SIGTERM", handler);
-      // No warning is made for SIGTERM
-      assertSpyCalls(consoleSpy, 0);
-    }
-  },
-});
-
 Deno.test(
   { permissions: { run: true, read: true } },
   async function processKill() {
@@ -691,6 +663,16 @@ Deno.test({
       assertStrictEquals(process.stdout.clearLine, undefined);
       assertStrictEquals(process.stdout.clearScreenDown, undefined);
     }
+
+    // Allows overwriting `process.stdout.isTTY`
+    // https://github.com/denoland/deno/issues/26123
+    const original = process.stdout.isTTY;
+    try {
+      process.stdout.isTTY = !isTTY;
+      assertEquals(process.stdout.isTTY, !isTTY);
+    } finally {
+      process.stdout.isTTY = original;
+    }
   },
 });
 
@@ -1165,3 +1147,14 @@ Deno.test("process.cpuUsage()", () => {
   assert(typeof cpuUsage.user === "number");
   assert(typeof cpuUsage.system === "number");
 });
+
+Deno.test("process.stdout.columns writable", () => {
+  process.stdout.columns = 80;
+  assertEquals(process.stdout.columns, 80);
+});
+
+Deno.test("getBuiltinModule", () => {
+  assert(process.getBuiltinModule("fs"));
+  assert(process.getBuiltinModule("node:fs"));
+  assertEquals(process.getBuiltinModule("something"), undefined);
+});
diff --git a/tests/unit_node/tls_test.ts b/tests/unit_node/tls_test.ts
index 93eacd5ec2..43d6205b0b 100644
--- a/tests/unit_node/tls_test.ts
+++ b/tests/unit_node/tls_test.ts
@@ -229,3 +229,31 @@ Deno.test("tls.rootCertificates is not empty", () => {
     (tls.rootCertificates as string[]).push("new cert");
   }, TypeError);
 });
+
+Deno.test("TLSSocket.alpnProtocol is set for client", async () => {
+  const listener = Deno.listenTls({
+    hostname: "localhost",
+    port: 0,
+    key,
+    cert,
+    alpnProtocols: ["a"],
+  });
+  const outgoing = tls.connect({
+    host: "::1",
+    servername: "localhost",
+    port: listener.addr.port,
+    ALPNProtocols: ["a"],
+    secureContext: {
+      ca: rootCaCert,
+      // deno-lint-ignore no-explicit-any
+    } as any,
+  });
+
+  const conn = await listener.accept();
+  const handshake = await conn.handshake();
+  assertEquals(handshake.alpnProtocol, "a");
+  conn.close();
+  outgoing.destroy();
+  listener.close();
+  await new Promise((resolve) => outgoing.on("close", resolve));
+});
diff --git a/tests/unit_node/util_test.ts b/tests/unit_node/util_test.ts
index edd5002623..6267018b12 100644
--- a/tests/unit_node/util_test.ts
+++ b/tests/unit_node/util_test.ts
@@ -348,3 +348,13 @@ Deno.test("[util] aborted()", async () => {
   await promise;
   assertEquals(done, true);
 });
+
+Deno.test("[util] styleText()", () => {
+  const redText = util.styleText("red", "error");
+  assertEquals(redText, "\x1B[31merror\x1B[39m");
+});
+
+Deno.test("[util] styleText() with array of formats", () => {
+  const colored = util.styleText(["red", "green"], "error");
+  assertEquals(colored, "\x1b[32m\x1b[31merror\x1b[39m\x1b[39m");
+});
diff --git a/tests/unit_node/worker_threads_test.ts b/tests/unit_node/worker_threads_test.ts
index ac797601f5..24a9107898 100644
--- a/tests/unit_node/worker_threads_test.ts
+++ b/tests/unit_node/worker_threads_test.ts
@@ -621,3 +621,204 @@ Deno.test({
     worker.terminate();
   },
 });
+
+Deno.test({
+  name: "[node/worker_threads] receiveMessageOnPort doesn't exit receive loop",
+  async fn() {
+    const worker = new workerThreads.Worker(
+      `
+      import { parentPort, receiveMessageOnPort } from "node:worker_threads";
+      parentPort.on("message", (msg) => {
+        const port = msg.port;
+        port.on("message", (msg2) => {
+          if (msg2 === "c") {
+            port.postMessage("done");
+            port.unref();
+            parentPort.unref();
+          }
+        });
+        parentPort.postMessage("ready");
+        const msg2 = receiveMessageOnPort(port);
+      });
+      `,
+      { eval: true },
+    );
+
+    const { port1, port2 } = new workerThreads.MessageChannel();
+
+    worker.postMessage({ port: port2 }, [port2]);
+
+    const done = Promise.withResolvers<boolean>();
+
+    port1.on("message", (msg) => {
+      assertEquals(msg, "done");
+      worker.unref();
+      port1.close();
+      done.resolve(true);
+    });
+    worker.on("message", (msg) => {
+      assertEquals(msg, "ready");
+      port1.postMessage("a");
+      port1.postMessage("b");
+      port1.postMessage("c");
+    });
+
+    const timeout = setTimeout(() => {
+      fail("Test timed out");
+    }, 20_000);
+    try {
+      const result = await done.promise;
+      assertEquals(result, true);
+    } finally {
+      clearTimeout(timeout);
+    }
+  },
+});
+
+Deno.test({
+  name: "[node/worker_threads] MessagePort.unref doesn't exit receive loop",
+  async fn() {
+    const worker = new workerThreads.Worker(
+      `
+      import { parentPort } from "node:worker_threads";
+      const assertEquals = (a, b) => {
+        if (a !== b) {
+          throw new Error();
+        }
+      };
+      let state = 0;
+      parentPort.on("message", (msg) => {
+        const port = msg.port;
+        const expect = ["a", "b", "c"];
+        port.on("message", (msg2) => {
+          assertEquals(msg2, expect[state++]);
+          if (msg2 === "c") {
+            port.postMessage({ type: "done", got: msg2 });
+            parentPort.unref();
+          }
+        });
+        port.unref();
+        parentPort.postMessage("ready");
+      });
+      `,
+      { eval: true },
+    );
+
+    const { port1, port2 } = new workerThreads.MessageChannel();
+
+    const done = Promise.withResolvers<boolean>();
+
+    port1.on("message", (msg) => {
+      assertEquals(msg.type, "done");
+      assertEquals(msg.got, "c");
+      worker.unref();
+      port1.close();
+      done.resolve(true);
+    });
+    worker.on("message", (msg) => {
+      assertEquals(msg, "ready");
+      port1.postMessage("a");
+      port1.postMessage("b");
+      port1.postMessage("c");
+    });
+    worker.postMessage({ port: port2 }, [port2]);
+
+    const timeout = setTimeout(() => {
+      fail("Test timed out");
+    }, 20_000);
+    try {
+      const result = await done.promise;
+      assertEquals(result, true);
+    } finally {
+      clearTimeout(timeout);
+    }
+  },
+});
+
+Deno.test({
+  name: "[node/worker_threads] npm:piscina wait loop hang regression",
+  async fn() {
+    const worker = new workerThreads.Worker(
+      `
+      import { assert, assertEquals } from "@std/assert";
+      import { parentPort, receiveMessageOnPort } from "node:worker_threads";
+
+      assert(parentPort !== null);
+
+      let currentTasks = 0;
+      let lastSeen = 0;
+
+      parentPort.on("message", (msg) => {
+        (async () => {
+          assert(typeof msg === "object" && msg !== null);
+          assert(msg.buf !== undefined);
+          assert(msg.port !== undefined);
+          const { buf, port } = msg;
+          port.postMessage("ready");
+          port.on("message", (msg) => onMessage(msg, buf, port));
+          atomicsWaitLoop(buf, port);
+        })();
+      });
+
+      function onMessage(msg, buf, port) {
+        currentTasks++;
+        (async () => {
+          assert(msg.taskName !== undefined);
+          port.postMessage({ type: "response", taskName: msg.taskName });
+          currentTasks--;
+          atomicsWaitLoop(buf, port);
+        })();
+      }
+
+      function atomicsWaitLoop(buf, port) {
+        while (currentTasks === 0) {
+          Atomics.wait(buf, 0, lastSeen);
+          lastSeen = Atomics.load(buf, 0);
+          let task;
+          while ((task = receiveMessageOnPort(port)) !== undefined) {
+            onMessage(task.message, buf, port);
+          }
+        }
+      }
+      `,
+      { eval: true },
+    );
+
+    const sab = new SharedArrayBuffer(4);
+    const buf = new Int32Array(sab);
+    const { port1, port2 } = new workerThreads.MessageChannel();
+
+    const done = Promise.withResolvers<boolean>();
+
+    port1.unref();
+
+    worker.postMessage({
+      type: "init",
+      buf,
+      port: port2,
+    }, [port2]);
+
+    let count = 0;
+    port1.on("message", (msg) => {
+      if (count++ === 0) {
+        assertEquals(msg, "ready");
+      } else {
+        assertEquals(msg.type, "response");
+        port1.close();
+        done.resolve(true);
+      }
+    });
+
+    port1.postMessage({
+      taskName: "doThing",
+    });
+
+    Atomics.add(buf, 0, 1);
+    Atomics.notify(buf, 0, 1);
+
+    worker.unref();
+
+    const result = await done.promise;
+    assertEquals(result, true);
+  },
+});
diff --git a/tests/unit_node/zlib_test.ts b/tests/unit_node/zlib_test.ts
index 8bce5ce7d1..de2d2450d1 100644
--- a/tests/unit_node/zlib_test.ts
+++ b/tests/unit_node/zlib_test.ts
@@ -7,9 +7,11 @@ import {
   brotliCompressSync,
   brotliDecompressSync,
   constants,
+  crc32,
   createBrotliCompress,
   createBrotliDecompress,
   createDeflate,
+  gzip,
   gzipSync,
   unzipSync,
 } from "node:zlib";
@@ -210,3 +212,21 @@ Deno.test("createBrotliCompress params", async () => {
   );
   assertEquals(output.length, input.length);
 });
+
+Deno.test("gzip() and gzipSync() accept ArrayBuffer", async () => {
+  const deffered = Promise.withResolvers<void>();
+  const buf = new ArrayBuffer(0);
+  let output: Buffer;
+  gzip(buf, (_err, data) => {
+    output = data;
+    deffered.resolve();
+  });
+  await deffered.promise;
+  assert(output! instanceof Buffer);
+  const outputSync = gzipSync(buf);
+  assert(outputSync instanceof Buffer);
+});
+
+Deno.test("crc32()", () => {
+  assertEquals(crc32("hello world"), 222957957);
+});
diff --git a/tests/util/server/Cargo.toml b/tests/util/server/Cargo.toml
index a321501b85..efc81da17c 100644
--- a/tests/util/server/Cargo.toml
+++ b/tests/util/server/Cargo.toml
@@ -21,6 +21,7 @@ bytes.workspace = true
 console_static_text.workspace = true
 deno_unsync = "0"
 denokv_proto.workspace = true
+faster-hex.workspace = true
 fastwebsockets.workspace = true
 flate2 = { workspace = true, features = ["default"] }
 futures.workspace = true
@@ -35,7 +36,7 @@ lazy-regex.workspace = true
 libc.workspace = true
 lsp-types.workspace = true
 monch.workspace = true
-nix.workspace = true
+nix = { workspace = true, features = ["fs", "term", "signal"] }
 once_cell.workspace = true
 os_pipe.workspace = true
 parking_lot.workspace = true
diff --git a/tests/util/server/src/builders.rs b/tests/util/server/src/builders.rs
index 4a4b6a7613..4a1510ce4c 100644
--- a/tests/util/server/src/builders.rs
+++ b/tests/util/server/src/builders.rs
@@ -28,6 +28,7 @@ use crate::fs::PathRef;
 use crate::http_server;
 use crate::jsr_registry_unset_url;
 use crate::lsp::LspClientBuilder;
+use crate::nodejs_org_mirror_unset_url;
 use crate::npm_registry_unset_url;
 use crate::pty::Pty;
 use crate::strip_ansi_codes;
@@ -78,6 +79,7 @@ impl DiagnosticLogger {
         logger.write_all(text.as_ref().as_bytes()).unwrap();
         logger.write_all(b"\n").unwrap();
       }
+      #[allow(clippy::print_stderr)]
       None => eprintln!("{}", text.as_ref()),
     }
   }
@@ -842,6 +844,12 @@ impl TestCommandBuilder {
     if !envs.contains_key("JSR_URL") {
       envs.insert("JSR_URL".to_string(), jsr_registry_unset_url());
     }
+    if !envs.contains_key("NODEJS_ORG_MIRROR") {
+      envs.insert(
+        "NODEJS_ORG_MIRROR".to_string(),
+        nodejs_org_mirror_unset_url(),
+      );
+    }
     for key in &self.envs_remove {
       envs.remove(key);
     }
diff --git a/tests/util/server/src/fs.rs b/tests/util/server/src/fs.rs
index 47d0d61fa1..7feb0799ae 100644
--- a/tests/util/server/src/fs.rs
+++ b/tests/util/server/src/fs.rs
@@ -285,7 +285,10 @@ impl PathRef {
   #[track_caller]
   pub fn assert_matches_file(&self, wildcard_file: impl AsRef<Path>) -> &Self {
     let wildcard_file = testdata_path().join(wildcard_file);
-    println!("output path {}", wildcard_file);
+    #[allow(clippy::print_stdout)]
+    {
+      println!("output path {}", wildcard_file);
+    }
     let expected_text = wildcard_file.read_to_string();
     self.assert_matches_text(&expected_text)
   }
diff --git a/tests/util/server/src/lib.rs b/tests/util/server/src/lib.rs
index 88e8287e08..89dc1ffc3b 100644
--- a/tests/util/server/src/lib.rs
+++ b/tests/util/server/src/lib.rs
@@ -1,8 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-#![allow(clippy::print_stdout)]
-#![allow(clippy::print_stderr)]
-
 use std::collections::HashMap;
 use std::env;
 use std::io::Write;
@@ -55,6 +52,7 @@ static GUARD: Lazy<Mutex<HttpServerCount>> = Lazy::new(Default::default);
 pub fn env_vars_for_npm_tests() -> Vec<(String, String)> {
   vec![
     ("NPM_CONFIG_REGISTRY".to_string(), npm_registry_url()),
+    ("NODEJS_ORG_MIRROR".to_string(), nodejs_org_mirror_url()),
     ("NO_COLOR".to_string(), "1".to_string()),
   ]
 }
@@ -133,6 +131,7 @@ pub fn env_vars_for_jsr_npm_tests() -> Vec<(String, String)> {
     ),
     ("DISABLE_JSR_PROVENANCE".to_string(), "true".to_string()),
     ("NO_COLOR".to_string(), "1".to_string()),
+    ("NODEJS_ORG_MIRROR".to_string(), nodejs_org_mirror_url()),
   ]
 }
 
@@ -178,27 +177,41 @@ pub fn deno_config_path() -> PathRef {
 
 /// Test server registry url.
 pub fn npm_registry_url() -> String {
-  "http://localhost:4260/".to_string()
+  format!("http://localhost:{}/", servers::PUBLIC_NPM_REGISTRY_PORT)
 }
 
 pub fn npm_registry_unset_url() -> String {
   "http://NPM_CONFIG_REGISTRY.is.unset".to_string()
 }
 
+pub fn nodejs_org_mirror_url() -> String {
+  format!(
+    "http://127.0.0.1:{}/",
+    servers::NODEJS_ORG_MIRROR_SERVER_PORT
+  )
+}
+
+pub fn nodejs_org_mirror_unset_url() -> String {
+  "http://NODEJS_ORG_MIRROR.is.unset".to_string()
+}
+
 pub fn jsr_registry_url() -> String {
-  "http://127.0.0.1:4250/".to_string()
+  format!("http://127.0.0.1:{}/", servers::JSR_REGISTRY_SERVER_PORT)
 }
 
 pub fn rekor_url() -> String {
-  "http://127.0.0.1:4251".to_string()
+  format!("http://127.0.0.1:{}", servers::PROVENANCE_MOCK_SERVER_PORT)
 }
 
 pub fn fulcio_url() -> String {
-  "http://127.0.0.1:4251".to_string()
+  format!("http://127.0.0.1:{}", servers::PROVENANCE_MOCK_SERVER_PORT)
 }
 
 pub fn gha_token_url() -> String {
-  "http://127.0.0.1:4251/gha_oidc?test=true".to_string()
+  format!(
+    "http://127.0.0.1:{}/gha_oidc?test=true",
+    servers::PROVENANCE_MOCK_SERVER_PORT
+  )
 }
 
 pub fn jsr_registry_unset_url() -> String {
@@ -302,12 +315,15 @@ async fn get_tcp_listener_stream(
     .collect::<Vec<_>>();
 
   // Eye catcher for HttpServerCount
-  println!("ready: {name} on {:?}", addresses);
+  #[allow(clippy::print_stdout)]
+  {
+    println!("ready: {name} on {:?}", addresses);
+  }
 
   futures::stream::select_all(listeners)
 }
 
-pub const TEST_SERVERS_COUNT: usize = 30;
+pub const TEST_SERVERS_COUNT: usize = 33;
 
 #[derive(Default)]
 struct HttpServerCount {
@@ -345,7 +361,10 @@ struct HttpServerStarter {
 
 impl Default for HttpServerStarter {
   fn default() -> Self {
-    println!("test_server starting...");
+    #[allow(clippy::print_stdout)]
+    {
+      println!("test_server starting...");
+    }
     let mut test_server = Command::new(test_server_path())
       .current_dir(testdata_path())
       .stdout(Stdio::piped())
@@ -479,6 +498,7 @@ pub fn run_collect(
   } = prog.wait_with_output().expect("failed to wait on child");
   let stdout = String::from_utf8(stdout).unwrap();
   let stderr = String::from_utf8(stderr).unwrap();
+  #[allow(clippy::print_stderr)]
   if expect_success != status.success() {
     eprintln!("stdout: <<<{stdout}>>>");
     eprintln!("stderr: <<<{stderr}>>>");
@@ -539,6 +559,7 @@ pub fn run_and_collect_output_with_args(
   } = deno.wait_with_output().expect("failed to wait on child");
   let stdout = String::from_utf8(stdout).unwrap();
   let stderr = String::from_utf8(stderr).unwrap();
+  #[allow(clippy::print_stderr)]
   if expect_success != status.success() {
     eprintln!("stdout: <<<{stdout}>>>");
     eprintln!("stderr: <<<{stderr}>>>");
@@ -560,9 +581,11 @@ pub fn deno_cmd_with_deno_dir(deno_dir: &TempDir) -> TestCommandBuilder {
   TestCommandBuilder::new(deno_dir.clone())
     .env("DENO_DIR", deno_dir.path())
     .env("NPM_CONFIG_REGISTRY", npm_registry_unset_url())
+    .env("NODEJS_ORG_MIRROR", nodejs_org_mirror_unset_url())
     .env("JSR_URL", jsr_registry_unset_url())
 }
 
+#[allow(clippy::print_stdout)]
 pub fn run_powershell_script_file(
   script_file_path: &str,
   args: Vec<&str>,
@@ -654,6 +677,7 @@ impl<'a> CheckOutputIntegrationTest<'a> {
 }
 
 pub fn wildcard_match(pattern: &str, text: &str) -> bool {
+  #[allow(clippy::print_stderr)]
   match wildcard_match_detailed(pattern, text) {
     WildcardMatchResult::Success => true,
     WildcardMatchResult::Fail(debug_output) => {
diff --git a/tests/util/server/src/lsp.rs b/tests/util/server/src/lsp.rs
index ffe72b88af..d34deb2161 100644
--- a/tests/util/server/src/lsp.rs
+++ b/tests/util/server/src/lsp.rs
@@ -157,6 +157,7 @@ impl LspStdoutReader {
     self.pending_messages.0.lock().len()
   }
 
+  #[allow(clippy::print_stderr)]
   pub fn output_pending_messages(&self) {
     let messages = self.pending_messages.0.lock();
     eprintln!("{:?}", messages);
@@ -308,34 +309,6 @@ impl InitializeParamsBuilder {
     self
   }
 
-  pub fn enable_inlay_hints(&mut self) -> &mut Self {
-    let options = self.initialization_options_mut();
-    options.insert(
-      "inlayHints".to_string(),
-      json!({
-        "parameterNames": {
-          "enabled": "all"
-        },
-        "parameterTypes": {
-          "enabled": true
-        },
-        "variableTypes": {
-          "enabled": true
-        },
-        "propertyDeclarationTypes": {
-          "enabled": true
-        },
-        "functionLikeReturnTypes": {
-          "enabled": true
-        },
-        "enumMemberValues": {
-          "enabled": true
-        }
-      }),
-    );
-    self
-  }
-
   pub fn disable_testing_api(&mut self) -> &mut Self {
     let obj = self
       .params
@@ -601,6 +574,7 @@ impl LspClientBuilder {
         for line in stderr.lines() {
           match line {
             Ok(line) => {
+              #[allow(clippy::print_stderr)]
               if print_stderr {
                 eprintln!("{}", line);
               }
@@ -615,7 +589,10 @@ impl LspClientBuilder {
                       continue;
                     }
                     Err(err) => {
-                      eprintln!("failed to parse perf record: {:#}", err);
+                      #[allow(clippy::print_stderr)]
+                      {
+                        eprintln!("failed to parse perf record: {:#}", err);
+                      }
                     }
                   }
                 }
@@ -810,11 +787,14 @@ impl LspClient {
       std::thread::sleep(Duration::from_millis(20));
     }
 
-    eprintln!("==== STDERR OUTPUT ====");
-    for line in found_lines {
-      eprintln!("{}", line)
+    #[allow(clippy::print_stderr)]
+    {
+      eprintln!("==== STDERR OUTPUT ====");
+      for line in found_lines {
+        eprintln!("{}", line)
+      }
+      eprintln!("== END STDERR OUTPUT ==");
     }
-    eprintln!("== END STDERR OUTPUT ==");
 
     panic!("Timed out waiting on condition.")
   }
diff --git a/tests/util/server/src/macros.rs b/tests/util/server/src/macros.rs
index fdbb977e9f..e076583f19 100644
--- a/tests/util/server/src/macros.rs
+++ b/tests/util/server/src/macros.rs
@@ -33,6 +33,7 @@ macro_rules! timeout {
           use std::io::Write;
           eprintln!("Test {function} timed out after {timeout} seconds, aborting");
           _ = std::io::stderr().flush();
+          #[allow(clippy::disallowed_methods)]
           ::std::process::exit(1);
         }
       });
diff --git a/tests/util/server/src/npm.rs b/tests/util/server/src/npm.rs
index f1c341738a..31686fa854 100644
--- a/tests/util/server/src/npm.rs
+++ b/tests/util/server/src/npm.rs
@@ -18,6 +18,7 @@ use crate::PathRef;
 
 pub const DENOTEST_SCOPE_NAME: &str = "@denotest";
 pub const DENOTEST2_SCOPE_NAME: &str = "@denotest2";
+pub const DENOTEST3_SCOPE_NAME: &str = "@denotest3";
 
 pub static PUBLIC_TEST_NPM_REGISTRY: Lazy<TestNpmRegistry> = Lazy::new(|| {
   TestNpmRegistry::new(
@@ -54,6 +55,18 @@ pub static PRIVATE_TEST_NPM_REGISTRY_2: Lazy<TestNpmRegistry> =
     )
   });
 
+pub static PRIVATE_TEST_NPM_REGISTRY_3: Lazy<TestNpmRegistry> =
+  Lazy::new(|| {
+    TestNpmRegistry::new(
+      NpmRegistryKind::Private,
+      &format!(
+        "http://localhost:{}",
+        crate::servers::PRIVATE_NPM_REGISTRY_3_PORT
+      ),
+      "npm-private3",
+    )
+  });
+
 pub enum NpmRegistryKind {
   Public,
   Private,
@@ -161,6 +174,17 @@ impl TestNpmRegistry {
       return Some((DENOTEST2_SCOPE_NAME, package_name_with_path));
     }
 
+    let prefix1 = format!("/{}/", DENOTEST3_SCOPE_NAME);
+    let prefix2 = format!("/{}%2f", DENOTEST3_SCOPE_NAME);
+
+    let maybe_package_name_with_path = uri_path
+      .strip_prefix(&prefix1)
+      .or_else(|| uri_path.strip_prefix(&prefix2));
+
+    if let Some(package_name_with_path) = maybe_package_name_with_path {
+      return Some((DENOTEST3_SCOPE_NAME, package_name_with_path));
+    }
+
     None
   }
 }
diff --git a/tests/util/server/src/pty.rs b/tests/util/server/src/pty.rs
index 5d8049fee9..07659262cf 100644
--- a/tests/util/server/src/pty.rs
+++ b/tests/util/server/src/pty.rs
@@ -61,7 +61,10 @@ impl Pty {
     if is_windows && *IS_CI {
       // the pty tests don't really start up on the windows CI for some reason
       // so ignore them for now
-      eprintln!("Ignoring windows CI.");
+      #[allow(clippy::print_stderr)]
+      {
+        eprintln!("Ignoring windows CI.");
+      }
       false
     } else {
       true
@@ -250,11 +253,14 @@ impl Pty {
     }
 
     let text = self.next_text();
-    eprintln!(
-      "------ Start Full Text ------\n{:?}\n------- End Full Text -------",
-      String::from_utf8_lossy(&self.read_bytes)
-    );
-    eprintln!("Next text: {:?}", text);
+    #[allow(clippy::print_stderr)]
+    {
+      eprintln!(
+        "------ Start Full Text ------\n{:?}\n------- End Full Text -------",
+        String::from_utf8_lossy(&self.read_bytes)
+      );
+      eprintln!("Next text: {:?}", text);
+    }
 
     false
   }
@@ -297,10 +303,12 @@ fn setup_pty(fd: i32) {
   use nix::sys::termios::tcsetattr;
   use nix::sys::termios::SetArg;
 
-  let mut term = tcgetattr(fd).unwrap();
+  // SAFETY: Nix crate requires value to implement the AsFd trait
+  let as_fd = unsafe { std::os::fd::BorrowedFd::borrow_raw(fd) };
+  let mut term = tcgetattr(as_fd).unwrap();
   // disable cooked mode
   term.local_flags.remove(termios::LocalFlags::ICANON);
-  tcsetattr(fd, SetArg::TCSANOW, &term).unwrap();
+  tcsetattr(as_fd, SetArg::TCSANOW, &term).unwrap();
 
   // turn on non-blocking mode so we get timeouts
   let flags = fcntl(fd, FcntlArg::F_GETFL).unwrap();
diff --git a/tests/util/server/src/servers/hyper_utils.rs b/tests/util/server/src/servers/hyper_utils.rs
index c2db7ea668..8e01151ed4 100644
--- a/tests/util/server/src/servers/hyper_utils.rs
+++ b/tests/util/server/src/servers/hyper_utils.rs
@@ -42,7 +42,10 @@ where
   let fut: Pin<Box<dyn Future<Output = Result<(), anyhow::Error>>>> =
     async move {
       let listener = TcpListener::bind(options.addr).await?;
-      println!("ready: {}", options.addr);
+      #[allow(clippy::print_stdout)]
+      {
+        println!("ready: {}", options.addr);
+      }
       loop {
         let (stream, _) = listener.accept().await?;
         let io = TokioIo::new(stream);
@@ -58,6 +61,7 @@ where
 
   if let Err(e) = fut.await {
     let err_str = e.to_string();
+    #[allow(clippy::print_stderr)]
     if !err_str.contains("early eof") {
       eprintln!("{}: {:?}", options.error_msg, e);
     }
@@ -89,6 +93,7 @@ pub async fn run_server_with_acceptor<'a, A, F, S>(
 
   if let Err(e) = fut.await {
     let err_str = e.to_string();
+    #[allow(clippy::print_stderr)]
     if !err_str.contains("early eof") {
       eprintln!("{}: {:?}", error_msg, e);
     }
@@ -135,6 +140,7 @@ async fn hyper_serve_connection<I, F, S>(
 
   if let Err(e) = result {
     let err_str = e.to_string();
+    #[allow(clippy::print_stderr)]
     if !err_str.contains("early eof") {
       eprintln!("{}: {:?}", error_msg, e);
     }
diff --git a/tests/util/server/src/servers/mod.rs b/tests/util/server/src/servers/mod.rs
index 3e18aafce4..0b1d99aeb9 100644
--- a/tests/util/server/src/servers/mod.rs
+++ b/tests/util/server/src/servers/mod.rs
@@ -39,6 +39,7 @@ use tokio::net::TcpStream;
 mod grpc;
 mod hyper_utils;
 mod jsr_registry;
+mod nodejs_org_mirror;
 mod npm_registry;
 mod ws;
 
@@ -86,11 +87,13 @@ const WS_CLOSE_PORT: u16 = 4244;
 const WS_PING_PORT: u16 = 4245;
 const H2_GRPC_PORT: u16 = 4246;
 const H2S_GRPC_PORT: u16 = 4247;
-const JSR_REGISTRY_SERVER_PORT: u16 = 4250;
-const PROVENANCE_MOCK_SERVER_PORT: u16 = 4251;
+pub(crate) const JSR_REGISTRY_SERVER_PORT: u16 = 4250;
+pub(crate) const PROVENANCE_MOCK_SERVER_PORT: u16 = 4251;
+pub(crate) const NODEJS_ORG_MIRROR_SERVER_PORT: u16 = 4252;
 pub(crate) const PUBLIC_NPM_REGISTRY_PORT: u16 = 4260;
 pub(crate) const PRIVATE_NPM_REGISTRY_1_PORT: u16 = 4261;
 pub(crate) const PRIVATE_NPM_REGISTRY_2_PORT: u16 = 4262;
+pub(crate) const PRIVATE_NPM_REGISTRY_3_PORT: u16 = 4263;
 
 // Use the single-threaded scheduler. The hyper server is used as a point of
 // comparison for the (single-threaded!) benchmarks in cli/bench. We're not
@@ -143,6 +146,12 @@ pub async fn run_all_servers() {
     npm_registry::private_npm_registry1(PRIVATE_NPM_REGISTRY_1_PORT);
   let private_npm_registry_2_server_futs =
     npm_registry::private_npm_registry2(PRIVATE_NPM_REGISTRY_2_PORT);
+  let private_npm_registry_3_server_futs =
+    npm_registry::private_npm_registry3(PRIVATE_NPM_REGISTRY_3_PORT);
+
+  // for serving node header files to node-gyp in tests
+  let node_js_mirror_server_fut =
+    nodejs_org_mirror::nodejs_org_mirror(NODEJS_ORG_MIRROR_SERVER_PORT);
 
   let mut futures = vec![
     redirect_server_fut.boxed_local(),
@@ -169,10 +178,12 @@ pub async fn run_all_servers() {
     h2_grpc_server_fut.boxed_local(),
     registry_server_fut.boxed_local(),
     provenance_mock_server_fut.boxed_local(),
+    node_js_mirror_server_fut.boxed_local(),
   ];
   futures.extend(npm_registry_server_futs);
   futures.extend(private_npm_registry_1_server_futs);
   futures.extend(private_npm_registry_2_server_futs);
+  futures.extend(private_npm_registry_3_server_futs);
 
   assert_eq!(futures.len(), TEST_SERVERS_COUNT);
 
@@ -194,7 +205,6 @@ fn json_body(value: serde_json::Value) -> UnsyncBoxBody<Bytes, Infallible> {
 
 /// Benchmark server that just serves "hello world" responses.
 async fn hyper_hello(port: u16) {
-  println!("hyper hello");
   let addr = SocketAddr::from(([127, 0, 0, 1], port));
   let handler = move |_: Request<hyper::body::Incoming>| async move {
     Ok::<_, anyhow::Error>(Response::new(UnsyncBoxBody::new(
@@ -338,7 +348,10 @@ async fn get_tcp_listener_stream(
     .collect::<Vec<_>>();
 
   // Eye catcher for HttpServerCount
-  println!("ready: {name} on {:?}", addresses);
+  #[allow(clippy::print_stdout)]
+  {
+    println!("ready: {name} on {:?}", addresses);
+  }
 
   futures::stream::select_all(listeners)
 }
@@ -354,7 +367,10 @@ async fn run_tls_client_auth_server(port: u16) {
   while let Some(Ok(mut tls_stream)) = tls.next().await {
     tokio::spawn(async move {
       let Ok(handshake) = tls_stream.handshake().await else {
-        eprintln!("Failed to handshake");
+        #[allow(clippy::print_stderr)]
+        {
+          eprintln!("Failed to handshake");
+        }
         return;
       };
       // We only need to check for the presence of client certificates
@@ -401,7 +417,6 @@ async fn absolute_redirect(
       .collect();
 
     if let Some(url) = query_params.get("redirect_to") {
-      println!("URL: {url:?}");
       let redirect = redirect_resp(url.to_owned());
       return Ok(redirect);
     }
@@ -409,7 +424,6 @@ async fn absolute_redirect(
 
   if path.starts_with("/REDIRECT") {
     let url = &req.uri().path()[9..];
-    println!("URL: {url:?}");
     let redirect = redirect_resp(url.to_string());
     return Ok(redirect);
   }
@@ -793,17 +807,17 @@ async fn main_server(
     (_, "/jsx/jsx-runtime") | (_, "/jsx/jsx-dev-runtime") => {
       let mut res = Response::new(string_body(
         r#"export function jsx(
-          _type,
-          _props,
-          _key,
-          _source,
-          _self,
-        ) {}
-        export const jsxs = jsx;
-        export const jsxDEV = jsx;
-        export const Fragment = Symbol("Fragment");
-        console.log("imported", import.meta.url);
-        "#,
+  _type,
+  _props,
+  _key,
+  _source,
+  _self,
+) {}
+export const jsxs = jsx;
+export const jsxDEV = jsx;
+export const Fragment = Symbol("Fragment");
+console.log("imported", import.meta.url);
+"#,
       ));
       res.headers_mut().insert(
         "Content-type",
@@ -1353,6 +1367,7 @@ async fn wrap_client_auth_https_server(port: u16) {
       // here. Rusttls ensures that they are valid and signed by the CA.
       match handshake.has_peer_certificates {
         true => { yield Ok(tls); },
+        #[allow(clippy::print_stderr)]
         false => { eprintln!("https_client_auth: no valid client certificate"); },
       };
     }
diff --git a/tests/util/server/src/servers/nodejs_org_mirror.rs b/tests/util/server/src/servers/nodejs_org_mirror.rs
new file mode 100644
index 0000000000..521e79d3c4
--- /dev/null
+++ b/tests/util/server/src/servers/nodejs_org_mirror.rs
@@ -0,0 +1,245 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+//! Server for NodeJS header tarballs, used by `node-gyp` in tests to download headers
+//!
+//! Loads from `testdata/assets`, if we update our node version in `process.versions` we'll need to
+//! update the header tarball there.
+
+#![allow(clippy::print_stderr)]
+
+use std::collections::HashMap;
+use std::convert::Infallible;
+use std::net::SocketAddr;
+use std::sync::LazyLock;
+
+use bytes::Bytes;
+use http::Response;
+use http::StatusCode;
+use http_body_util::combinators::UnsyncBoxBody;
+use http_body_util::Full;
+use parking_lot::Mutex;
+
+use crate::servers::hyper_utils::run_server;
+use crate::servers::hyper_utils::ServerKind;
+use crate::servers::hyper_utils::ServerOptions;
+use crate::servers::string_body;
+use crate::testdata_path;
+use crate::PathRef;
+
+/// a little helper extension trait to log errors but convert to option
+trait OkWarn<T, E> {
+  fn ok_warn(self) -> Option<T>;
+}
+
+impl<T, E> OkWarn<T, E> for Result<T, E>
+where
+  E: std::fmt::Display,
+{
+  fn ok_warn(self) -> Option<T> {
+    self
+      .inspect_err(|err| {
+        eprintln!(
+          "test_server warning: error occurred in nodejs_org_mirror.rs: {err}"
+        )
+      })
+      .ok()
+  }
+}
+
+pub static NODEJS_MIRROR: LazyLock<NodeJsMirror> =
+  LazyLock::new(NodeJsMirror::default);
+
+#[derive(Default)]
+pub struct NodeJsMirror {
+  cache: Mutex<HashMap<String, Bytes>>,
+  checksum_cache: Mutex<HashMap<String, String>>,
+}
+
+fn asset_file_path(file: &str) -> PathRef {
+  testdata_path().join("assets").join("node-gyp").join(file)
+}
+
+impl NodeJsMirror {
+  pub fn get_header_bytes(&self, file: &str) -> Option<Bytes> {
+    let mut cache = self.cache.lock();
+    let entry = cache.entry(file.to_owned());
+    match entry {
+      std::collections::hash_map::Entry::Occupied(occupied) => {
+        Some(occupied.get().clone())
+      }
+      std::collections::hash_map::Entry::Vacant(vacant) => {
+        let contents = asset_file_path(file);
+        let contents = contents
+          .read_to_bytes_if_exists()
+          .ok_warn()
+          .map(Bytes::from)?;
+        vacant.insert(contents.clone());
+        Some(contents)
+      }
+    }
+  }
+
+  fn get_checksum(&self, file: &str, bytes: Bytes) -> String {
+    use sha2::Digest;
+    if let Some(checksum) = self.checksum_cache.lock().get(file).cloned() {
+      return checksum;
+    }
+    let mut hasher = sha2::Sha256::new();
+    hasher.update(&bytes);
+    let checksum = faster_hex::hex_string(hasher.finalize().as_ref());
+    self
+      .checksum_cache
+      .lock()
+      .insert(file.to_owned(), checksum.clone());
+    checksum
+  }
+
+  pub fn get_checksum_file(&self, version: &str) -> Option<String> {
+    let mut entries = Vec::with_capacity(2);
+
+    let header_file = header_tar_name(version);
+    let header_bytes = self.get_header_bytes(&header_file)?;
+    let header_checksum = self.get_checksum(&header_file, header_bytes);
+    entries.push((header_file, header_checksum));
+
+    if cfg!(windows) {
+      if !cfg!(target_arch = "x86_64") {
+        panic!("unsupported target arch on windows, only support x86_64");
+      }
+      let Some(bytes) = self.get_node_lib_bytes(version, "win-x64") else {
+        eprintln!("test server failed to get node lib");
+        return None;
+      };
+      {
+        let file = format!("{version}/win-x64/node.lib");
+        let checksum = self.get_checksum(&file, bytes);
+        let filename_for_checksum =
+          file.trim_start_matches(&format!("{version}/"));
+        entries.push((filename_for_checksum.to_owned(), checksum));
+      }
+    }
+
+    Some(
+      entries
+        .into_iter()
+        .map(|(file, checksum)| format!("{checksum}  {file}"))
+        .collect::<Vec<_>>()
+        .join("\n"),
+    )
+  }
+
+  pub fn get_node_lib_bytes(
+    &self,
+    version: &str,
+    platform: &str,
+  ) -> Option<Bytes> {
+    let mut cache = self.cache.lock();
+    let file_name = format!("{version}/{platform}/node.lib");
+    let entry = cache.entry(file_name);
+    match entry {
+      std::collections::hash_map::Entry::Occupied(occupied) => {
+        Some(occupied.get().clone())
+      }
+      std::collections::hash_map::Entry::Vacant(vacant) => {
+        let tarball_filename =
+          format!("{version}__{platform}__node.lib.tar.gz");
+        let contents = asset_file_path(&tarball_filename);
+        let contents = contents.read_to_bytes_if_exists().ok_warn()?;
+        let extracted = Bytes::from(extract_tarball(&contents)?);
+        vacant.insert(extracted.clone());
+        Some(extracted)
+      }
+    }
+  }
+}
+
+fn header_tar_name(version: &str) -> String {
+  format!("node-{version}-headers.tar.gz")
+}
+
+fn extract_tarball(compressed: &[u8]) -> Option<Vec<u8>> {
+  let mut out = Vec::with_capacity(compressed.len());
+  let decoder = flate2::read::GzDecoder::new(compressed);
+  let mut archive = tar::Archive::new(decoder);
+  for file in archive.entries().ok_warn()? {
+    let mut file = file.ok_warn()?;
+
+    std::io::copy(&mut file, &mut out).ok_warn()?;
+  }
+  Some(out)
+}
+
+/// Server for node JS header tarballs, used by `node-gyp` in tests
+pub async fn nodejs_org_mirror(port: u16) {
+  let addr = SocketAddr::from(([127, 0, 0, 1], port));
+
+  run_server(
+    ServerOptions {
+      addr,
+      error_msg: "nodejs mirror server error",
+      kind: ServerKind::Auto,
+    },
+    |req| async move {
+      let path = req.uri().path();
+      if path.contains("-headers.tar.gz")
+        || path.contains("SHASUMS256.txt")
+        || path.contains("node.lib")
+      {
+        let mut parts = path.split('/');
+        let _ = parts.next(); // empty
+        let Some(version) = parts.next() else {
+          return not_found(format!("missing node version in path: {path}"));
+        };
+        let Some(file) = parts.next() else {
+          return not_found(format!("missing file version in path: {path}"));
+        };
+        if file == "SHASUMS256.txt" {
+          let Some(checksum_file) = NODEJS_MIRROR.get_checksum_file(version)
+          else {
+            return not_found(format!("failed to get header checksum: {path}"));
+          };
+          return Ok(Response::new(string_body(&checksum_file)));
+        } else if !file.contains("headers") {
+          let platform = file;
+          let Some(file) = parts.next() else {
+            return not_found("expected file");
+          };
+          if file != "node.lib" {
+            return not_found(format!(
+              "unexpected file name, expected node.lib, got: {file}"
+            ));
+          }
+          let Some(bytes) = NODEJS_MIRROR.get_node_lib_bytes(version, platform)
+          else {
+            return not_found("expected node lib bytes");
+          };
+
+          return Ok(Response::new(UnsyncBoxBody::new(Full::new(bytes))));
+        }
+
+        let Some(bytes) = NODEJS_MIRROR.get_header_bytes(file) else {
+          return not_found(format!(
+            "couldn't find headers for version {version}, missing file: {file}"
+          ));
+        };
+        Ok(Response::new(UnsyncBoxBody::new(Full::new(bytes))))
+      } else {
+        not_found(format!("unexpected request path: {path}"))
+      }
+    },
+  )
+  .await
+}
+
+fn not_found(
+  msg: impl AsRef<str>,
+) -> Result<Response<UnsyncBoxBody<Bytes, Infallible>>, anyhow::Error> {
+  let msg = msg.as_ref();
+  eprintln!(
+    "test_server warning: error likely occurred in nodejs_org_mirror.rs: {msg}"
+  );
+  Response::builder()
+    .status(StatusCode::NOT_FOUND)
+    .body(string_body(msg))
+    .map_err(|e| e.into())
+}
diff --git a/tests/util/server/src/servers/npm_registry.rs b/tests/util/server/src/servers/npm_registry.rs
index acbd9cab48..4ada468fac 100644
--- a/tests/util/server/src/servers/npm_registry.rs
+++ b/tests/util/server/src/servers/npm_registry.rs
@@ -56,6 +56,14 @@ pub fn private_npm_registry2(port: u16) -> Vec<LocalBoxFuture<'static, ()>> {
   )
 }
 
+pub fn private_npm_registry3(port: u16) -> Vec<LocalBoxFuture<'static, ()>> {
+  run_npm_server(
+    port,
+    "npm private registry server error",
+    private_npm_registry3_handler,
+  )
+}
+
 fn run_npm_server<F, S>(
   port: u16,
   error_msg: &'static str,
@@ -141,6 +149,13 @@ async fn private_npm_registry2_handler(
   handle_req_for_registry(req, &npm::PRIVATE_TEST_NPM_REGISTRY_2).await
 }
 
+async fn private_npm_registry3_handler(
+  req: Request<hyper::body::Incoming>,
+) -> Result<Response<UnsyncBoxBody<Bytes, Infallible>>, anyhow::Error> {
+  // No auth for this registry
+  handle_req_for_registry(req, &npm::PRIVATE_TEST_NPM_REGISTRY_3).await
+}
+
 async fn handle_req_for_registry(
   req: Request<Incoming>,
   test_npm_registry: &npm::TestNpmRegistry,
diff --git a/tests/util/server/src/servers/ws.rs b/tests/util/server/src/servers/ws.rs
index 815119b6a1..dd4efbf659 100644
--- a/tests/util/server/src/servers/ws.rs
+++ b/tests/util/server/src/servers/ws.rs
@@ -76,6 +76,7 @@ pub async fn run_wss2_server(port: u16) {
       let server: Handshake<_, Bytes> = h2.handshake(tls);
       let mut server = match server.await {
         Ok(server) => server,
+        #[allow(clippy::print_stdout)]
         Err(e) => {
           println!("Failed to handshake h2: {e:?}");
           return;
@@ -87,6 +88,7 @@ pub async fn run_wss2_server(port: u16) {
         };
         let (recv, send) = match conn {
           Ok(conn) => conn,
+          #[allow(clippy::print_stdout)]
           Err(e) => {
             println!("Failed to accept a connection: {e:?}");
             break;
@@ -137,6 +139,7 @@ where
           .map_err(|e| anyhow!("Error upgrading websocket connection: {}", e))
           .unwrap();
 
+        #[allow(clippy::print_stderr)]
         if let Err(e) = handler(ws).await {
           eprintln!("Error in websocket connection: {}", e);
         }
@@ -152,6 +155,7 @@ where
       .serve_connection(io, service)
       .with_upgrades();
 
+    #[allow(clippy::print_stderr)]
     if let Err(e) = conn.await {
       eprintln!("websocket server error: {e:?}");
     }
@@ -162,16 +166,19 @@ async fn handle_wss_stream(
   recv: Request<RecvStream>,
   mut send: SendResponse<Bytes>,
 ) -> Result<(), h2::Error> {
+  #[allow(clippy::print_stderr)]
   if recv.method() != Method::CONNECT {
     eprintln!("wss2: refusing non-CONNECT stream");
     send.send_reset(Reason::REFUSED_STREAM);
     return Ok(());
   }
+  #[allow(clippy::print_stderr)]
   let Some(protocol) = recv.extensions().get::<h2::ext::Protocol>() else {
     eprintln!("wss2: refusing no-:protocol stream");
     send.send_reset(Reason::REFUSED_STREAM);
     return Ok(());
   };
+  #[allow(clippy::print_stderr)]
   if protocol.as_str() != "websocket" && protocol.as_str() != "WebSocket" {
     eprintln!("wss2: refusing non-websocket stream");
     send.send_reset(Reason::REFUSED_STREAM);
diff --git a/tests/wpt/runner/expectation.json b/tests/wpt/runner/expectation.json
index 1b31f26e5a..3477d8d9bf 100644
--- a/tests/wpt/runner/expectation.json
+++ b/tests/wpt/runner/expectation.json
@@ -54,127 +54,65 @@
       "pbkdf2.https.any.worker.html?7001-8000": true,
       "pbkdf2.https.any.worker.html?8001-last": true,
       "cfrg_curves_bits.https.any.html": [
-        "X25519 key derivation checks for all-zero value result with a key of order 0",
-        "X25519 key derivation checks for all-zero value result with a key of order 1",
-        "X25519 key derivation checks for all-zero value result with a key of order 8",
-        "X25519 key derivation checks for all-zero value result with a key of order p-1 (order 2)",
-        "X25519 key derivation checks for all-zero value result with a key of order p (=0, order 4)",
-        "X25519 key derivation checks for all-zero value result with a key of order p+1 (=1, order 1)",
         "X448 key derivation checks for all-zero value result with a key of order 0",
         "X448 key derivation checks for all-zero value result with a key of order 1",
         "X448 key derivation checks for all-zero value result with a key of order p-1 (order 2)",
         "X448 key derivation checks for all-zero value result with a key of order p (=0, order 4)",
         "X448 key derivation checks for all-zero value result with a key of order p+1 (=1, order 1)",
-        "X25519 good parameters",
-        "X25519 mixed case parameters",
-        "X25519 short result",
-        "X25519 non-multiple of 8 bits",
-        "X25519 mismatched algorithms",
-        "X25519 no deriveBits usage for base key",
         "X448 good parameters",
         "X448 mixed case parameters",
         "X448 short result",
         "X448 non-multiple of 8 bits",
         "X448 mismatched algorithms",
         "X448 no deriveBits usage for base key",
-        "X448 base key is not a private key",
         "X448 public property value is a private key",
         "X448 public property value is a secret key",
         "X448 asking for too many bits"
       ],
       "cfrg_curves_bits.https.any.worker.html": [
-        "X25519 key derivation checks for all-zero value result with a key of order 0",
-        "X25519 key derivation checks for all-zero value result with a key of order 1",
-        "X25519 key derivation checks for all-zero value result with a key of order 8",
-        "X25519 key derivation checks for all-zero value result with a key of order p-1 (order 2)",
-        "X25519 key derivation checks for all-zero value result with a key of order p (=0, order 4)",
-        "X25519 key derivation checks for all-zero value result with a key of order p+1 (=1, order 1)",
         "X448 key derivation checks for all-zero value result with a key of order 0",
         "X448 key derivation checks for all-zero value result with a key of order 1",
         "X448 key derivation checks for all-zero value result with a key of order p-1 (order 2)",
         "X448 key derivation checks for all-zero value result with a key of order p (=0, order 4)",
         "X448 key derivation checks for all-zero value result with a key of order p+1 (=1, order 1)",
-        "X25519 good parameters",
-        "X25519 mixed case parameters",
-        "X25519 short result",
-        "X25519 non-multiple of 8 bits",
-        "X25519 mismatched algorithms",
-        "X25519 no deriveBits usage for base key",
         "X448 good parameters",
         "X448 mixed case parameters",
         "X448 short result",
         "X448 non-multiple of 8 bits",
         "X448 mismatched algorithms",
         "X448 no deriveBits usage for base key",
-        "X448 base key is not a private key",
         "X448 public property value is a private key",
         "X448 public property value is a secret key",
         "X448 asking for too many bits"
       ],
       "cfrg_curves_keys.https.any.html": [
-        "X25519 deriveBits checks for all-zero value result with a key of order 0",
-        "X25519 deriveBits checks for all-zero value result with a key of order 1",
-        "X25519 deriveBits checks for all-zero value result with a key of order 8",
-        "X25519 deriveBits checks for all-zero value result with a key of order p-1 (order 2)",
-        "X25519 deriveBits checks for all-zero value result with a key of order p (=0, order 4)",
-        "X25519 deriveBits checks for all-zero value result with a key of order p+1 (=1, order 1)",
         "X448 deriveBits checks for all-zero value result with a key of order 0",
         "X448 deriveBits checks for all-zero value result with a key of order 1",
         "X448 deriveBits checks for all-zero value result with a key of order p-1 (order 2)",
         "X448 deriveBits checks for all-zero value result with a key of order p (=0, order 4)",
         "X448 deriveBits checks for all-zero value result with a key of order p+1 (=1, order 1)",
-        "Key derivation using a X25519 generated keys.",
-        "Key derivation using a X448 generated keys.",
-        "X25519 good parameters",
-        "X25519 mixed case parameters",
-        "X25519 mismatched algorithms",
         "X448 good parameters",
         "X448 mixed case parameters",
         "X448 mismatched algorithms",
         "X448 no deriveKey usage for base key",
-        "X448 base key is not a private key",
         "X448 public property value is a private key",
         "X448 public property value is a secret key"
       ],
       "cfrg_curves_keys.https.any.worker.html": [
-        "X25519 deriveBits checks for all-zero value result with a key of order 0",
-        "X25519 deriveBits checks for all-zero value result with a key of order 1",
-        "X25519 deriveBits checks for all-zero value result with a key of order 8",
-        "X25519 deriveBits checks for all-zero value result with a key of order p-1 (order 2)",
-        "X25519 deriveBits checks for all-zero value result with a key of order p (=0, order 4)",
-        "X25519 deriveBits checks for all-zero value result with a key of order p+1 (=1, order 1)",
         "X448 deriveBits checks for all-zero value result with a key of order 0",
         "X448 deriveBits checks for all-zero value result with a key of order 1",
         "X448 deriveBits checks for all-zero value result with a key of order p-1 (order 2)",
         "X448 deriveBits checks for all-zero value result with a key of order p (=0, order 4)",
         "X448 deriveBits checks for all-zero value result with a key of order p+1 (=1, order 1)",
-        "Key derivation using a X25519 generated keys.",
-        "Key derivation using a X448 generated keys.",
-        "X25519 good parameters",
-        "X25519 mixed case parameters",
-        "X25519 mismatched algorithms",
         "X448 good parameters",
         "X448 mixed case parameters",
         "X448 mismatched algorithms",
         "X448 no deriveKey usage for base key",
-        "X448 base key is not a private key",
         "X448 public property value is a private key",
         "X448 public property value is a secret key"
       ],
-      "derived_bits_length.https.any.html": [
-        "X25519 derivation with 256 as 'length' parameter",
-        "X25519 derivation with 0 as 'length' parameter",
-        "X25519 derivation with null as 'length' parameter",
-        "X25519 derivation with undefined as 'length' parameter",
-        "X25519 derivation with omitted as 'length' parameter"
-      ],
-      "derived_bits_length.https.any.worker.html": [
-        "X25519 derivation with 256 as 'length' parameter",
-        "X25519 derivation with 0 as 'length' parameter",
-        "X25519 derivation with null as 'length' parameter",
-        "X25519 derivation with undefined as 'length' parameter",
-        "X25519 derivation with omitted as 'length' parameter"
-      ]
+      "derived_bits_length.https.any.html": true,
+      "derived_bits_length.https.any.worker.html": true
     },
     "digest": {
       "digest.https.any.html": true,
@@ -819,82 +757,16 @@
       ],
       "failures_X25519.https.any.html": true,
       "failures_X25519.https.any.worker.html": true,
-      "failures_X448.https.any.html": [
-        "Bad usages: generateKey({name: X448}, true, [encrypt])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, encrypt])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, deriveKey, encrypt])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, encrypt])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits, deriveKey, deriveBits, encrypt])",
-        "Bad usages: generateKey({name: X448}, true, [decrypt])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, decrypt])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, deriveKey, decrypt])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, decrypt])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits, deriveKey, deriveBits, decrypt])",
-        "Bad usages: generateKey({name: X448}, true, [sign])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, sign])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, deriveKey, sign])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, sign])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits, deriveKey, deriveBits, sign])",
-        "Bad usages: generateKey({name: X448}, true, [verify])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, verify])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, deriveKey, verify])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, verify])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits, deriveKey, deriveBits, verify])",
-        "Bad usages: generateKey({name: X448}, true, [wrapKey])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, wrapKey])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, deriveKey, wrapKey])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, wrapKey])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits, deriveKey, deriveBits, wrapKey])",
-        "Bad usages: generateKey({name: X448}, true, [unwrapKey])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, unwrapKey])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, deriveKey, unwrapKey])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, unwrapKey])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits, deriveKey, deriveBits, unwrapKey])",
-        "Empty usages: generateKey({name: X448}, false, [])",
-        "Empty usages: generateKey({name: X448}, true, [])"
-      ],
-      "failures_X448.https.any.worker.html": [
-        "Bad usages: generateKey({name: X448}, true, [encrypt])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, encrypt])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, deriveKey, encrypt])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, encrypt])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits, deriveKey, deriveBits, encrypt])",
-        "Bad usages: generateKey({name: X448}, true, [decrypt])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, decrypt])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, deriveKey, decrypt])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, decrypt])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits, deriveKey, deriveBits, decrypt])",
-        "Bad usages: generateKey({name: X448}, true, [sign])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, sign])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, deriveKey, sign])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, sign])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits, deriveKey, deriveBits, sign])",
-        "Bad usages: generateKey({name: X448}, true, [verify])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, verify])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, deriveKey, verify])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, verify])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits, deriveKey, deriveBits, verify])",
-        "Bad usages: generateKey({name: X448}, true, [wrapKey])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, wrapKey])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, deriveKey, wrapKey])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, wrapKey])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits, deriveKey, deriveBits, wrapKey])",
-        "Bad usages: generateKey({name: X448}, true, [unwrapKey])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, unwrapKey])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, deriveKey, unwrapKey])",
-        "Bad usages: generateKey({name: X448}, true, [deriveBits, unwrapKey])",
-        "Bad usages: generateKey({name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits, deriveKey, deriveBits, unwrapKey])",
-        "Empty usages: generateKey({name: X448}, false, [])",
-        "Empty usages: generateKey({name: X448}, true, [])"
-      ],
+      "failures_X448.https.any.html": true,
+      "failures_X448.https.any.worker.html": true,
       "successes_Ed25519.https.any.html": true,
       "successes_Ed25519.https.any.worker.html": true,
       "successes_Ed448.https.any.html": false,
       "successes_Ed448.https.any.worker.html": false,
       "successes_X25519.https.any.html": true,
       "successes_X25519.https.any.worker.html": true,
-      "successes_X448.https.any.html": false,
-      "successes_X448.https.any.worker.html": false
+      "successes_X448.https.any.html": true,
+      "successes_X448.https.any.worker.html": true
     },
     "historical.any.html": false,
     "historical.any.worker.html": false,
@@ -981,10 +853,6 @@
         "Good parameters with ignored JWK alg: X25519 (jwk, object(crv, d, x, kty), {name: X25519}, true, [deriveBits])",
         "Good parameters: X25519 bits (jwk, object(crv, d, x, kty), {name: X25519}, true, [deriveKey, deriveBits, deriveKey, deriveBits])",
         "Good parameters with ignored JWK alg: X25519 (jwk, object(crv, d, x, kty), {name: X25519}, true, [deriveKey, deriveBits, deriveKey, deriveBits])",
-        "Good parameters: X448 bits (spki, buffer(68), {name: X448}, true, [])",
-        "Good parameters: X448 bits (jwk, object(kty, crv, x), {name: X448}, true, [])",
-        "Good parameters with ignored JWK alg: X448 (jwk, object(kty, crv, x), {name: X448}, true, [])",
-        "Good parameters: X448 bits (raw, buffer(56), {name: X448}, true, [])",
         "Good parameters: X448 bits (pkcs8, buffer(72), {name: X448}, true, [deriveKey])",
         "Good parameters: X448 bits (jwk, object(crv, d, x, kty), {name: X448}, true, [deriveKey])",
         "Good parameters with ignored JWK alg: X448 (jwk, object(crv, d, x, kty), {name: X448}, true, [deriveKey])",
@@ -997,17 +865,10 @@
         "Good parameters: X448 bits (pkcs8, buffer(72), {name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits])",
         "Good parameters: X448 bits (jwk, object(crv, d, x, kty), {name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits])",
         "Good parameters with ignored JWK alg: X448 (jwk, object(crv, d, x, kty), {name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits])",
-        "Good parameters: X448 bits (spki, buffer(68), {name: X448}, false, [])",
-        "Good parameters: X448 bits (jwk, object(kty, crv, x), {name: X448}, false, [])",
-        "Good parameters: X448 bits (raw, buffer(56), {name: X448}, false, [])",
         "Good parameters: X448 bits (pkcs8, buffer(72), {name: X448}, false, [deriveKey])",
-        "Good parameters: X448 bits (jwk, object(crv, d, x, kty), {name: X448}, false, [deriveKey])",
         "Good parameters: X448 bits (pkcs8, buffer(72), {name: X448}, false, [deriveBits, deriveKey])",
-        "Good parameters: X448 bits (jwk, object(crv, d, x, kty), {name: X448}, false, [deriveBits, deriveKey])",
         "Good parameters: X448 bits (pkcs8, buffer(72), {name: X448}, false, [deriveBits])",
-        "Good parameters: X448 bits (jwk, object(crv, d, x, kty), {name: X448}, false, [deriveBits])",
-        "Good parameters: X448 bits (pkcs8, buffer(72), {name: X448}, false, [deriveKey, deriveBits, deriveKey, deriveBits])",
-        "Good parameters: X448 bits (jwk, object(crv, d, x, kty), {name: X448}, false, [deriveKey, deriveBits, deriveKey, deriveBits])"
+        "Good parameters: X448 bits (pkcs8, buffer(72), {name: X448}, false, [deriveKey, deriveBits, deriveKey, deriveBits])"
       ],
       "okp_importKey.https.any.worker.html": [
         "Good parameters: Ed448 bits (spki, buffer(69), {name: Ed448}, true, [verify])",
@@ -1049,10 +910,6 @@
         "Good parameters with ignored JWK alg: X25519 (jwk, object(crv, d, x, kty), {name: X25519}, true, [deriveBits])",
         "Good parameters: X25519 bits (jwk, object(crv, d, x, kty), {name: X25519}, true, [deriveKey, deriveBits, deriveKey, deriveBits])",
         "Good parameters with ignored JWK alg: X25519 (jwk, object(crv, d, x, kty), {name: X25519}, true, [deriveKey, deriveBits, deriveKey, deriveBits])",
-        "Good parameters: X448 bits (spki, buffer(68), {name: X448}, true, [])",
-        "Good parameters: X448 bits (jwk, object(kty, crv, x), {name: X448}, true, [])",
-        "Good parameters with ignored JWK alg: X448 (jwk, object(kty, crv, x), {name: X448}, true, [])",
-        "Good parameters: X448 bits (raw, buffer(56), {name: X448}, true, [])",
         "Good parameters: X448 bits (pkcs8, buffer(72), {name: X448}, true, [deriveKey])",
         "Good parameters: X448 bits (jwk, object(crv, d, x, kty), {name: X448}, true, [deriveKey])",
         "Good parameters with ignored JWK alg: X448 (jwk, object(crv, d, x, kty), {name: X448}, true, [deriveKey])",
@@ -1065,17 +922,10 @@
         "Good parameters: X448 bits (pkcs8, buffer(72), {name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits])",
         "Good parameters: X448 bits (jwk, object(crv, d, x, kty), {name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits])",
         "Good parameters with ignored JWK alg: X448 (jwk, object(crv, d, x, kty), {name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits])",
-        "Good parameters: X448 bits (spki, buffer(68), {name: X448}, false, [])",
-        "Good parameters: X448 bits (jwk, object(kty, crv, x), {name: X448}, false, [])",
-        "Good parameters: X448 bits (raw, buffer(56), {name: X448}, false, [])",
         "Good parameters: X448 bits (pkcs8, buffer(72), {name: X448}, false, [deriveKey])",
-        "Good parameters: X448 bits (jwk, object(crv, d, x, kty), {name: X448}, false, [deriveKey])",
         "Good parameters: X448 bits (pkcs8, buffer(72), {name: X448}, false, [deriveBits, deriveKey])",
-        "Good parameters: X448 bits (jwk, object(crv, d, x, kty), {name: X448}, false, [deriveBits, deriveKey])",
         "Good parameters: X448 bits (pkcs8, buffer(72), {name: X448}, false, [deriveBits])",
-        "Good parameters: X448 bits (jwk, object(crv, d, x, kty), {name: X448}, false, [deriveBits])",
-        "Good parameters: X448 bits (pkcs8, buffer(72), {name: X448}, false, [deriveKey, deriveBits, deriveKey, deriveBits])",
-        "Good parameters: X448 bits (jwk, object(crv, d, x, kty), {name: X448}, false, [deriveKey, deriveBits, deriveKey, deriveBits])"
+        "Good parameters: X448 bits (pkcs8, buffer(72), {name: X448}, false, [deriveKey, deriveBits, deriveKey, deriveBits])"
       ],
       "okp_importKey_failures_Ed25519.https.any.html": [
         "Bad key length: importKey(raw, {name: Ed25519}, true, [verify])",
@@ -1155,8 +1005,62 @@
         "Invalid key pair: importKey(jwk(private), {name: X25519}, true, [deriveBits])",
         "Invalid key pair: importKey(jwk(private), {name: X25519}, true, [deriveKey, deriveBits, deriveKey, deriveBits])"
       ],
-      "okp_importKey_failures_X448.https.any.html": false,
-      "okp_importKey_failures_X448.https.any.worker.html": false,
+      "okp_importKey_failures_X448.https.any.html": [
+        "Empty usages: importKey(pkcs8, {name: X448}, true, [])",
+        "Empty usages: importKey(pkcs8, {name: X448}, false, [])",
+        "Bad key length: importKey(raw, {name: X448}, true, [])",
+        "Bad key length: importKey(raw, {name: X448}, false, [])",
+        "Bad key length: importKey(jwk(private), {name: X448}, true, [deriveKey])",
+        "Bad key length: importKey(jwk(private), {name: X448}, false, [deriveKey])",
+        "Bad key length: importKey(jwk(private), {name: X448}, true, [deriveBits, deriveKey])",
+        "Bad key length: importKey(jwk(private), {name: X448}, false, [deriveBits, deriveKey])",
+        "Bad key length: importKey(jwk(private), {name: X448}, true, [deriveBits])",
+        "Bad key length: importKey(jwk(private), {name: X448}, false, [deriveBits])",
+        "Bad key length: importKey(jwk(private), {name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits])",
+        "Bad key length: importKey(jwk(private), {name: X448}, false, [deriveKey, deriveBits, deriveKey, deriveBits])",
+        "Bad key length: importKey(jwk (public) , {name: X448}, true, [])",
+        "Bad key length: importKey(jwk (public) , {name: X448}, false, [])",
+        "Missing JWK 'x' parameter: importKey(jwk(private), {name: X448}, true, [deriveKey])",
+        "Missing JWK 'x' parameter: importKey(jwk(private), {name: X448}, false, [deriveKey])",
+        "Missing JWK 'x' parameter: importKey(jwk(private), {name: X448}, true, [deriveBits, deriveKey])",
+        "Missing JWK 'x' parameter: importKey(jwk(private), {name: X448}, false, [deriveBits, deriveKey])",
+        "Missing JWK 'x' parameter: importKey(jwk(private), {name: X448}, true, [deriveBits])",
+        "Missing JWK 'x' parameter: importKey(jwk(private), {name: X448}, false, [deriveBits])",
+        "Missing JWK 'x' parameter: importKey(jwk(private), {name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits])",
+        "Missing JWK 'x' parameter: importKey(jwk(private), {name: X448}, false, [deriveKey, deriveBits, deriveKey, deriveBits])",
+        "Invalid key pair: importKey(jwk(private), {name: X448}, true, [deriveKey])",
+        "Invalid key pair: importKey(jwk(private), {name: X448}, true, [deriveBits, deriveKey])",
+        "Invalid key pair: importKey(jwk(private), {name: X448}, true, [deriveBits])",
+        "Invalid key pair: importKey(jwk(private), {name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits])"
+      ],
+      "okp_importKey_failures_X448.https.any.worker.html": [
+        "Empty usages: importKey(pkcs8, {name: X448}, true, [])",
+        "Empty usages: importKey(pkcs8, {name: X448}, false, [])",
+        "Bad key length: importKey(raw, {name: X448}, true, [])",
+        "Bad key length: importKey(raw, {name: X448}, false, [])",
+        "Bad key length: importKey(jwk(private), {name: X448}, true, [deriveKey])",
+        "Bad key length: importKey(jwk(private), {name: X448}, false, [deriveKey])",
+        "Bad key length: importKey(jwk(private), {name: X448}, true, [deriveBits, deriveKey])",
+        "Bad key length: importKey(jwk(private), {name: X448}, false, [deriveBits, deriveKey])",
+        "Bad key length: importKey(jwk(private), {name: X448}, true, [deriveBits])",
+        "Bad key length: importKey(jwk(private), {name: X448}, false, [deriveBits])",
+        "Bad key length: importKey(jwk(private), {name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits])",
+        "Bad key length: importKey(jwk(private), {name: X448}, false, [deriveKey, deriveBits, deriveKey, deriveBits])",
+        "Bad key length: importKey(jwk (public) , {name: X448}, true, [])",
+        "Bad key length: importKey(jwk (public) , {name: X448}, false, [])",
+        "Missing JWK 'x' parameter: importKey(jwk(private), {name: X448}, true, [deriveKey])",
+        "Missing JWK 'x' parameter: importKey(jwk(private), {name: X448}, false, [deriveKey])",
+        "Missing JWK 'x' parameter: importKey(jwk(private), {name: X448}, true, [deriveBits, deriveKey])",
+        "Missing JWK 'x' parameter: importKey(jwk(private), {name: X448}, false, [deriveBits, deriveKey])",
+        "Missing JWK 'x' parameter: importKey(jwk(private), {name: X448}, true, [deriveBits])",
+        "Missing JWK 'x' parameter: importKey(jwk(private), {name: X448}, false, [deriveBits])",
+        "Missing JWK 'x' parameter: importKey(jwk(private), {name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits])",
+        "Missing JWK 'x' parameter: importKey(jwk(private), {name: X448}, false, [deriveKey, deriveBits, deriveKey, deriveBits])",
+        "Invalid key pair: importKey(jwk(private), {name: X448}, true, [deriveKey])",
+        "Invalid key pair: importKey(jwk(private), {name: X448}, true, [deriveBits, deriveKey])",
+        "Invalid key pair: importKey(jwk(private), {name: X448}, true, [deriveBits])",
+        "Invalid key pair: importKey(jwk(private), {name: X448}, true, [deriveKey, deriveBits, deriveKey, deriveBits])"
+      ],
       "crashtests": {
         "importKey-unsettled-promise.https.any.html": true,
         "importKey-unsettled-promise.https.any.worker.html": true
@@ -1531,18 +1435,28 @@
     },
     "wrapKey_unwrapKey": {
       "wrapKey_unwrapKey.https.any.html": [
-        "Can wrap and unwrap X25519 private key keys as non-extractable using pkcs8 and AES-CTR",
-        "Can wrap and unwrap X25519 private key keys as non-extractable using pkcs8 and AES-CBC",
-        "Can wrap and unwrap X25519 private key keys as non-extractable using pkcs8 and AES-GCM",
-        "Can wrap and unwrap X25519 private key keys as non-extractable using pkcs8 and AES-KW",
-        "Can wrap and unwrap X25519 private key keys as non-extractable using pkcs8 and RSA-OAEP"
+        "Can wrap and unwrap X448 private key keys using pkcs8 and AES-CTR",
+        "Can wrap and unwrap X448 private key keys as non-extractable using pkcs8 and AES-CTR",
+        "Can wrap and unwrap X448 private key keys using pkcs8 and AES-CBC",
+        "Can wrap and unwrap X448 private key keys as non-extractable using pkcs8 and AES-CBC",
+        "Can wrap and unwrap X448 private key keys using pkcs8 and AES-GCM",
+        "Can wrap and unwrap X448 private key keys as non-extractable using pkcs8 and AES-GCM",
+        "Can wrap and unwrap X448 private key keys using pkcs8 and AES-KW",
+        "Can wrap and unwrap X448 private key keys as non-extractable using pkcs8 and AES-KW",
+        "Can wrap and unwrap X448 private key keys using pkcs8 and RSA-OAEP",
+        "Can wrap and unwrap X448 private key keys as non-extractable using pkcs8 and RSA-OAEP"
       ],
       "wrapKey_unwrapKey.https.any.worker.html": [
-        "Can wrap and unwrap X25519 private key keys as non-extractable using pkcs8 and AES-CTR",
-        "Can wrap and unwrap X25519 private key keys as non-extractable using pkcs8 and AES-CBC",
-        "Can wrap and unwrap X25519 private key keys as non-extractable using pkcs8 and AES-GCM",
-        "Can wrap and unwrap X25519 private key keys as non-extractable using pkcs8 and AES-KW",
-        "Can wrap and unwrap X25519 private key keys as non-extractable using pkcs8 and RSA-OAEP"
+        "Can wrap and unwrap X448 private key keys using pkcs8 and AES-CTR",
+        "Can wrap and unwrap X448 private key keys as non-extractable using pkcs8 and AES-CTR",
+        "Can wrap and unwrap X448 private key keys using pkcs8 and AES-CBC",
+        "Can wrap and unwrap X448 private key keys as non-extractable using pkcs8 and AES-CBC",
+        "Can wrap and unwrap X448 private key keys using pkcs8 and AES-GCM",
+        "Can wrap and unwrap X448 private key keys as non-extractable using pkcs8 and AES-GCM",
+        "Can wrap and unwrap X448 private key keys using pkcs8 and AES-KW",
+        "Can wrap and unwrap X448 private key keys as non-extractable using pkcs8 and AES-KW",
+        "Can wrap and unwrap X448 private key keys using pkcs8 and RSA-OAEP",
+        "Can wrap and unwrap X448 private key keys as non-extractable using pkcs8 and RSA-OAEP"
       ]
     }
   },
@@ -11711,9 +11625,6 @@
         "ctor-1.html": false,
         "ctor-null.html": false,
         "ctor-undefined.html": false,
-        "same-origin.html": [
-          "non-parsable URL"
-        ],
         "terminate.html": true,
         "use-base-url.html": false
       },
@@ -12297,18 +12208,8 @@
       "Component: hash Left: {\"hash\":\"a\"} Right: {\"hash\":\"b\"}"
     ],
     "urlpattern.any.html": [
-      "Pattern: [{\"pathname\":\"/foo/:bar?\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/:bar*\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/(.*)?\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/*?\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/(.*)*\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/**\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [\"https://(sub.)?example.com/foo\"] Inputs: [\"https://example.com/foo\"]",
-      "Pattern: [\"https://(sub(?:.))?example.com/foo\"] Inputs: [\"https://example.com/foo\"]",
-      "Pattern: [\"data\\\\:text/javascript,let x = 100/:tens?5;\"] Inputs: [\"data:text/javascript,let x = 100/5;\"]",
       "Pattern: [{\"hostname\":\"bad\\\\:hostname\"}] Inputs: undefined",
       "Pattern: [] Inputs: []",
-      "Pattern: [{\"pathname\":\"*{}**?\"}] Inputs: [{\"pathname\":\"foobar\"}]",
       "Pattern: [{\"pathname\":\"/foo/bar\"},{\"ignoreCase\":true}] Inputs: [{\"pathname\":\"/FOO/BAR\"}]",
       "Pattern: [\"https://example.com:8080/foo?bar#baz\",{\"ignoreCase\":true}] Inputs: [{\"pathname\":\"/FOO\",\"search\":\"BAR\",\"hash\":\"BAZ\",\"baseURL\":\"https://example.com:8080\"}]",
       "Pattern: [{\"pathname\":\"/([[a-z]--a])\"}] Inputs: [{\"pathname\":\"/a\"}]",
@@ -12317,18 +12218,8 @@
       "Pattern: [{\"pathname\":\"/([\\\\d&&[0-1]])\"}] Inputs: [{\"pathname\":\"/3\"}]"
     ],
     "urlpattern.any.worker.html": [
-      "Pattern: [{\"pathname\":\"/foo/:bar?\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/:bar*\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/(.*)?\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/*?\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/(.*)*\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/**\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [\"https://(sub.)?example.com/foo\"] Inputs: [\"https://example.com/foo\"]",
-      "Pattern: [\"https://(sub(?:.))?example.com/foo\"] Inputs: [\"https://example.com/foo\"]",
-      "Pattern: [\"data\\\\:text/javascript,let x = 100/:tens?5;\"] Inputs: [\"data:text/javascript,let x = 100/5;\"]",
       "Pattern: [{\"hostname\":\"bad\\\\:hostname\"}] Inputs: undefined",
       "Pattern: [] Inputs: []",
-      "Pattern: [{\"pathname\":\"*{}**?\"}] Inputs: [{\"pathname\":\"foobar\"}]",
       "Pattern: [{\"pathname\":\"/foo/bar\"},{\"ignoreCase\":true}] Inputs: [{\"pathname\":\"/FOO/BAR\"}]",
       "Pattern: [\"https://example.com:8080/foo?bar#baz\",{\"ignoreCase\":true}] Inputs: [{\"pathname\":\"/FOO\",\"search\":\"BAR\",\"hash\":\"BAZ\",\"baseURL\":\"https://example.com:8080\"}]",
       "Pattern: [{\"pathname\":\"/([[a-z]--a])\"}] Inputs: [{\"pathname\":\"/a\"}]",
@@ -12337,18 +12228,8 @@
       "Pattern: [{\"pathname\":\"/([\\\\d&&[0-1]])\"}] Inputs: [{\"pathname\":\"/3\"}]"
     ],
     "urlpattern.https.any.html": [
-      "Pattern: [{\"pathname\":\"/foo/:bar?\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/:bar*\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/(.*)?\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/*?\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/(.*)*\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/**\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [\"https://(sub.)?example.com/foo\"] Inputs: [\"https://example.com/foo\"]",
-      "Pattern: [\"https://(sub(?:.))?example.com/foo\"] Inputs: [\"https://example.com/foo\"]",
-      "Pattern: [\"data\\\\:text/javascript,let x = 100/:tens?5;\"] Inputs: [\"data:text/javascript,let x = 100/5;\"]",
       "Pattern: [{\"hostname\":\"bad\\\\:hostname\"}] Inputs: undefined",
       "Pattern: [] Inputs: []",
-      "Pattern: [{\"pathname\":\"*{}**?\"}] Inputs: [{\"pathname\":\"foobar\"}]",
       "Pattern: [{\"pathname\":\"/foo/bar\"},{\"ignoreCase\":true}] Inputs: [{\"pathname\":\"/FOO/BAR\"}]",
       "Pattern: [\"https://example.com:8080/foo?bar#baz\",{\"ignoreCase\":true}] Inputs: [{\"pathname\":\"/FOO\",\"search\":\"BAR\",\"hash\":\"BAZ\",\"baseURL\":\"https://example.com:8080\"}]",
       "Pattern: [{\"pathname\":\"/([[a-z]--a])\"}] Inputs: [{\"pathname\":\"/a\"}]",
@@ -12357,18 +12238,8 @@
       "Pattern: [{\"pathname\":\"/([\\\\d&&[0-1]])\"}] Inputs: [{\"pathname\":\"/3\"}]"
     ],
     "urlpattern.https.any.worker.html": [
-      "Pattern: [{\"pathname\":\"/foo/:bar?\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/:bar*\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/(.*)?\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/*?\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/(.*)*\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [{\"pathname\":\"/foo/**\"}] Inputs: [{\"pathname\":\"/foo\"}]",
-      "Pattern: [\"https://(sub.)?example.com/foo\"] Inputs: [\"https://example.com/foo\"]",
-      "Pattern: [\"https://(sub(?:.))?example.com/foo\"] Inputs: [\"https://example.com/foo\"]",
-      "Pattern: [\"data\\\\:text/javascript,let x = 100/:tens?5;\"] Inputs: [\"data:text/javascript,let x = 100/5;\"]",
       "Pattern: [{\"hostname\":\"bad\\\\:hostname\"}] Inputs: undefined",
       "Pattern: [] Inputs: []",
-      "Pattern: [{\"pathname\":\"*{}**?\"}] Inputs: [{\"pathname\":\"foobar\"}]",
       "Pattern: [{\"pathname\":\"/foo/bar\"},{\"ignoreCase\":true}] Inputs: [{\"pathname\":\"/FOO/BAR\"}]",
       "Pattern: [\"https://example.com:8080/foo?bar#baz\",{\"ignoreCase\":true}] Inputs: [{\"pathname\":\"/FOO\",\"search\":\"BAR\",\"hash\":\"BAZ\",\"baseURL\":\"https://example.com:8080\"}]",
       "Pattern: [{\"pathname\":\"/([[a-z]--a])\"}] Inputs: [{\"pathname\":\"/a\"}]",
diff --git a/tests/wpt/runner/utils.ts b/tests/wpt/runner/utils.ts
index 1674419cd1..140c388ec2 100644
--- a/tests/wpt/runner/utils.ts
+++ b/tests/wpt/runner/utils.ts
@@ -76,7 +76,10 @@ export function getManifest(): Manifest {
 
 /// WPT TEST EXPECTATIONS
 
-const EXPECTATION_PATH = join(ROOT_PATH, "./tests/wpt/runner/expectation.json");
+export const EXPECTATION_PATH = join(
+  ROOT_PATH,
+  "./tests/wpt/runner/expectation.json",
+);
 
 export interface Expectation {
   [key: string]: Expectation | boolean | string[] | { ignore: boolean };
@@ -87,9 +90,12 @@ export function getExpectation(): Expectation {
   return JSON.parse(expectationText);
 }
 
-export function saveExpectation(expectation: Expectation) {
+export function saveExpectation(
+  expectation: Expectation,
+  path: string = EXPECTATION_PATH,
+) {
   Deno.writeTextFileSync(
-    EXPECTATION_PATH,
+    path,
     JSON.stringify(expectation, undefined, "  ") + "\n",
   );
 }
@@ -134,6 +140,15 @@ export function runPy<T extends Omit<Deno.CommandOptions, "cwd">>(
   }).spawn();
 }
 
+export async function runGitDiff(args: string[]): string {
+  await new Deno.Command("git", {
+    args: ["diff", ...args],
+    stdout: "inherit",
+    stderr: "inherit",
+    cwd: ROOT_PATH,
+  }).output();
+}
+
 export async function checkPy3Available() {
   const { success, stdout } = await runPy(["--version"], {
     stdout: "piped",
diff --git a/tests/wpt/wpt.ts b/tests/wpt/wpt.ts
index c42ff51e6e..b13a10cf4c 100755
--- a/tests/wpt/wpt.ts
+++ b/tests/wpt/wpt.ts
@@ -18,6 +18,7 @@ import {
   checkPy3Available,
   escapeLoneSurrogates,
   Expectation,
+  EXPECTATION_PATH,
   generateRunInfo,
   getExpectation,
   getExpectFailForCase,
@@ -30,6 +31,7 @@ import {
   noIgnore,
   quiet,
   rest,
+  runGitDiff,
   runPy,
   updateManifest,
   wptreport,
@@ -256,7 +258,16 @@ async function run() {
     await Deno.writeTextFile(wptreport, JSON.stringify(report) + "\n");
   }
 
+  const newExpectations = newExpectation(results);
+  const tmp = Deno.makeTempFileSync();
+  saveExpectation(newExpectations, tmp);
+
   const code = reportFinal(results, endTime - startTime);
+
+  // Run git diff to see what changed
+  await runGitDiff([EXPECTATION_PATH, tmp]);
+  Deno.removeSync(tmp);
+
   Deno.exit(code);
 }
 
@@ -390,6 +401,19 @@ async function update() {
     await Deno.writeTextFile(json, JSON.stringify(results) + "\n");
   }
 
+  const newExpectations = newExpectation(results);
+  saveExpectation(newExpectations);
+
+  reportFinal(results, endTime - startTime);
+
+  console.log(blue("Updated expectation.json to match reality."));
+
+  Deno.exit(0);
+}
+
+function newExpectation(
+  results: { test: TestToRun; result: TestResult }[],
+): Expectation {
   const resultTests: Record<
     string,
     { passed: string[]; failed: string[]; testSucceeded: boolean }
@@ -431,13 +455,7 @@ async function update() {
     );
   }
 
-  saveExpectation(currentExpectation);
-
-  reportFinal(results, endTime - startTime);
-
-  console.log(blue("Updated expectation.json to match reality."));
-
-  Deno.exit(0);
+  return currentExpectation;
 }
 
 function insertExpectation(
diff --git a/tools/core_import_map.json b/tools/core_import_map.json
index aae4e63a45..0811672b16 100644
--- a/tools/core_import_map.json
+++ b/tools/core_import_map.json
@@ -247,6 +247,7 @@
     "ext:runtime/41_prompt.js": "../runtime/js/41_prompt.js",
     "ext:runtime/90_deno_ns.js": "../runtime/js/90_deno_ns.js",
     "ext:runtime/98_global_scope.js": "../runtime/js/98_global_scope.js",
+    "ext:runtime/telemetry.js": "../runtime/js/telemetry.js",
     "ext:deno_node/_util/std_fmt_colors.ts": "../ext/node/polyfills/_util/std_fmt_colors.ts",
     "@std/archive": "../tests/util/std/archive/mod.ts",
     "@std/archive/tar": "../tests/util/std/archive/tar.ts",
diff --git a/tools/format.js b/tools/format.js
index 74c608644b..b29667ca77 100755
--- a/tools/format.js
+++ b/tools/format.js
@@ -1,4 +1,4 @@
-#!/usr/bin/env -S deno run --allow-write --allow-read --allow-run=deno --allow-net --config=tests/config/deno.json
+#!/usr/bin/env -S deno run --allow-all --config=tests/config/deno.json
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 import { join, ROOT_PATH } from "./util.js";
 
diff --git a/tools/lint.js b/tools/lint.js
index 04e72c4c90..21064a05bf 100755
--- a/tools/lint.js
+++ b/tools/lint.js
@@ -1,4 +1,4 @@
-#!/usr/bin/env -S deno run --allow-write --allow-read --allow-run --allow-net --config=tests/config/deno.json
+#!/usr/bin/env -S deno run --allow-all --config=tests/config/deno.json
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 // deno-lint-ignore-file no-console
@@ -56,12 +56,13 @@ async function dlint() {
     ":!:cli/tsc/compiler.d.ts",
     ":!:runtime/examples/",
     ":!:target/",
+    ":!:tests/ffi/tests/test.js",
     ":!:tests/registry/**",
     ":!:tests/specs/**",
     ":!:tests/testdata/**",
     ":!:tests/unit_node/testdata/**",
-    ":!:tests/wpt/suite/**",
     ":!:tests/wpt/runner/**",
+    ":!:tests/wpt/suite/**",
   ]);
 
   if (!sourceFiles.length) {
@@ -198,7 +199,7 @@ async function ensureNoNewITests() {
     "bench_tests.rs": 0,
     "cache_tests.rs": 0,
     "cert_tests.rs": 0,
-    "check_tests.rs": 18,
+    "check_tests.rs": 2,
     "compile_tests.rs": 0,
     "coverage_tests.rs": 0,
     "eval_tests.rs": 0,
@@ -218,9 +219,9 @@ async function ensureNoNewITests() {
     "pm_tests.rs": 0,
     "publish_tests.rs": 0,
     "repl_tests.rs": 0,
-    "run_tests.rs": 331,
+    "run_tests.rs": 20,
     "shared_library_tests.rs": 0,
-    "task_tests.rs": 3,
+    "task_tests.rs": 2,
     "test_tests.rs": 0,
     "upgrade_tests.rs": 0,
     "vendor_tests.rs": 1,
diff --git a/tools/napi/generate_symbols_lists.js b/tools/napi/generate_symbols_lists.js
index 11cf1c434a..efb0edc043 100755
--- a/tools/napi/generate_symbols_lists.js
+++ b/tools/napi/generate_symbols_lists.js
@@ -1,7 +1,7 @@
 #!/usr/bin/env -S deno run --allow-read --allow-write
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-import exports from "../../cli/napi/sym/symbol_exports.json" with {
+import exports from "../../ext/napi/sym/symbol_exports.json" with {
   type: "json",
 };
 
@@ -17,7 +17,7 @@ const symbolExportLists = {
 
 for await (const [os, def] of Object.entries(symbolExportLists)) {
   const defUrl = new URL(
-    `../../cli/napi/generated_symbol_exports_list_${os}.def`,
+    `../../ext/napi/generated_symbol_exports_list_${os}.def`,
     import.meta.url,
   );
   await Deno.writeTextFile(defUrl.pathname, def, { create: true });
diff --git a/tools/release/promote_to_release.ts b/tools/release/promote_to_release.ts
old mode 100644
new mode 100755
index c14b590cab..046f4d33a8
--- a/tools/release/promote_to_release.ts
+++ b/tools/release/promote_to_release.ts
@@ -5,7 +5,7 @@
 
 import { $ } from "jsr:@david/dax@0.41.0";
 import { gray } from "jsr:@std/fmt@1/colors";
-import { patchver } from "jsr:@deno/patchver@0.1.0";
+import { patchver } from "jsr:@deno/patchver@0.2.0";
 
 const SUPPORTED_TARGETS = [
   "aarch64-apple-darwin",
diff --git a/tools/release/release_doc_template.md b/tools/release/release_doc_template.md
index fec1746bfb..b372185337 100644
--- a/tools/release/release_doc_template.md
+++ b/tools/release/release_doc_template.md
@@ -30,7 +30,7 @@ Release checklist: <LINK TO THIS FORKED GIST GOES HERE>
 
 ## Patch release preparation
 
-**If you are cutting a patch release**: First you need to sync commits to the
+⛔ **If you are cutting a patch release**: First you need to sync commits to the
 `v$MINOR_VERSION` branch in the `deno` repo.
 
 To do that, you need to cherry-pick commits from the main branch to the
@@ -75,13 +75,13 @@ verify on GitHub that everything looks correct.
   1. Click on the "Run workflow" button.
   1. In the drop down, select the minor branch (`v$MINOR_VERSION`) if doing a
      patch release or the main branch if doing a minor release.
-  1. For the kind of release, select either "patch", "minor", or "major".
+  1. For the kind of release, select either `patch` or `minor`.
   1. Run the workflow.
 
 - [ ] Wait for the workflow to complete and for a pull request to be
       automatically opened. Review the pull request, make any necessary changes,
       and merge it.
-  - ⛔ DO NOT create a release tag manually That will automatically happen.
+  - ⛔ **DO NOT** create a release tag manually That will automatically happen.
 
   <details>
      <summary>Failure Steps</summary>
@@ -120,7 +120,8 @@ verify on GitHub that everything looks correct.
   (https://github.com/denoland/deno/releases).
 
 - ⛔ Verify that:
-  - [ ] There are 14 assets on the release draft.
+  - [ ] There are 24 assets on the
+        [GitHub release draft](https://github.com/denoland/deno/releases/v$VERSION).
   - [ ] There are 10 zip files for this version on
         [dl.deno.land](https://console.cloud.google.com/storage/browser/dl.deno.land/release/v$VERSION).
 
diff --git a/tools/util.js b/tools/util.js
index 99133628ce..8c7cea15d8 100644
--- a/tools/util.js
+++ b/tools/util.js
@@ -11,7 +11,7 @@ export { delay } from "@std/async/delay";
 
 // [toolName] --version output
 const versions = {
-  "dlint": "dlint 0.60.0",
+  "dlint": "dlint 0.68.0",
 };
 
 const compressed = new Set(["ld64.lld", "rcodesign"]);
@@ -178,7 +178,7 @@ export function getPrebuiltToolPath(toolName) {
   return join(PREBUILT_TOOL_DIR, toolName + executableSuffix);
 }
 
-const commitId = "b8aac22e0cd7c1c6557a56a813fe0c25486fafee";
+const commitId = "7a3a6fee951b3381c59aa4c907274957f324ce8c";
 const downloadUrl =
   `https://raw.githubusercontent.com/denoland/deno_third_party/${commitId}/prebuilt/${platformDirName}`;