diff --git a/.dprint.json b/.dprint.json
index 082eb30058..3b2376f786 100644
--- a/.dprint.json
+++ b/.dprint.json
@@ -65,11 +65,15 @@
     "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-0.6.3.wasm",
     "https://plugins.dprint.dev/exec-0.5.0.json@8d9972eee71fa1590e04873540421f3eda7674d0f1aae3d7c788615e7b7413d0",
diff --git a/.github/workflows/cargo_publish.yml b/.github/workflows/cargo_publish.yml
index 8d164ea1bf..3af97f4662 100644
--- a/.github/workflows/cargo_publish.yml
+++ b/.github/workflows/cargo_publish.yml
@@ -10,7 +10,7 @@ concurrency:
 jobs:
   build:
     name: cargo publish
-    runs-on: ubuntu-20.04-xl
+    runs-on: ubuntu-24.04-xl
     timeout-minutes: 90
 
     env:
@@ -33,7 +33,7 @@ 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/ci.generate.ts b/.github/workflows/ci.generate.ts
index 98272abe4e..5ed02d3cde 100755
--- a/.github/workflows/ci.generate.ts
+++ b/.github/workflows/ci.generate.ts
@@ -5,15 +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 = 21;
+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 selfHostedMacosArmRunner = "self-hosted";
 
 const Runners = {
   linuxX86: {
@@ -40,7 +41,8 @@ const Runners = {
   macosArm: {
     os: "macos",
     arch: "aarch64",
-    runner: macosArmRunner,
+    runner:
+      `\${{ github.repository == 'denoland/deno' && startsWith(github.ref, 'refs/tags/') && '${selfHostedMacosArmRunner}' || '${macosArmRunner}' }}`,
   },
   windowsX86: {
     os: "windows",
@@ -59,7 +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 = {
@@ -71,7 +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" |
@@ -86,7 +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
@@ -193,7 +195,7 @@ const installNodeStep = {
 };
 const installDenoStep = {
   name: "Install Deno",
-  uses: "denoland/setup-deno@v1",
+  uses: "denoland/setup-deno@v2",
   with: { "deno-version": "v1.x" },
 };
 
diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 161b8719c8..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: '${{ (!contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'')) && ''ubuntu-22.04'' || ''macos-14'' }}'
+            runner: '${{ (!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
@@ -252,22 +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
@@ -299,8 +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=$(pwd)/target/release/lto-cache
@@ -310,8 +310,8 @@ jobs:
           __1
           RUSTDOCFLAGS<<__1
             -C linker-plugin-lto=true
-            -C linker=clang-18
-            -C link-arg=-fuse-ld=lld-18
+            -C linker=clang-19
+            -C link-arg=-fuse-ld=lld-19
             -C link-arg=-ldl
             -C link-arg=-Wl,--allow-shlib-undefined
             -C link-arg=-Wl,--thinlto-cache-dir=$(pwd)/target/release/lto-cache
@@ -319,7 +319,7 @@ jobs:
             --cfg tokio_unstable
             $RUSTFLAGS
           __1
-          CC=/usr/bin/clang-18
+          CC=/usr/bin/clang-19
           CFLAGS=-flto=thin $CFLAGS
           " > $GITHUB_ENV
       - name: Remove macOS cURL --ipv4 flag
@@ -361,8 +361,8 @@ jobs:
           path: |-
             ~/.cargo/registry/index
             ~/.cargo/registry/cache
-          key: '21-cargo-home-${{ matrix.os }}-${{ matrix.arch }}-${{ hashFiles(''Cargo.lock'') }}'
-          restore-keys: '21-cargo-home-${{ matrix.os }}-${{ matrix.arch }}'
+          key: '25-cargo-home-${{ matrix.os }}-${{ matrix.arch }}-${{ hashFiles(''Cargo.lock'') }}'
+          restore-keys: '25-cargo-home-${{ matrix.os }}-${{ matrix.arch }}'
         if: '!(matrix.skip)'
       - name: Restore cache build output (PR)
         uses: actions/cache/restore@v4
@@ -375,7 +375,7 @@ jobs:
             !./target/*/*.zip
             !./target/*/*.tar.gz
           key: never_saved
-          restore-keys: '21-cargo-target-${{ matrix.os }}-${{ matrix.arch }}-${{ matrix.profile }}-${{ matrix.job }}-'
+          restore-keys: '25-cargo-target-${{ matrix.os }}-${{ matrix.arch }}-${{ matrix.profile }}-${{ matrix.job }}-'
       - name: Apply and update mtime cache
         if: '!(matrix.skip) && (!startsWith(github.ref, ''refs/tags/''))'
         uses: ./.github/mtime_cache
@@ -685,10 +685,10 @@ jobs:
             !./target/*/*.zip
             !./target/*/*.sha256sum
             !./target/*/*.tar.gz
-          key: '21-cargo-target-${{ 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 bdcb483e38..b86b8acd94 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -765,6 +765,8 @@ dependencies = [
  "fastwebsockets",
  "file_test_runner",
  "flaky_test",
+ "hickory-client",
+ "hickory-server",
  "http 1.1.0",
  "http-body-util",
  "hyper 1.4.1",
@@ -778,8 +780,6 @@ dependencies = [
  "serde",
  "test_server",
  "tokio",
- "trust-dns-client",
- "trust-dns-server",
  "url",
  "uuid",
  "zeromq",
@@ -1154,7 +1154,7 @@ dependencies = [
 
 [[package]]
 name = "deno"
-version = "2.0.2"
+version = "2.0.6"
 dependencies = [
  "anstream",
  "async-trait",
@@ -1196,7 +1196,6 @@ dependencies = [
  "dprint-plugin-markdown",
  "dprint-plugin-typescript",
  "env_logger",
- "eszip",
  "fancy-regex",
  "faster-hex",
  "flate2",
@@ -1214,7 +1213,6 @@ dependencies = [
  "lazy-regex",
  "libc",
  "libsui",
- "libuv-sys-lite",
  "libz-sys",
  "log",
  "lsp-types",
@@ -1222,7 +1220,6 @@ dependencies = [
  "markup_fmt",
  "memmem",
  "monch",
- "napi_sym",
  "nix",
  "node_resolver",
  "notify",
@@ -1263,9 +1260,7 @@ dependencies = [
  "walkdir",
  "which 4.4.2",
  "winapi",
- "windows-sys 0.52.0",
  "winres",
- "yoke",
  "zeromq",
  "zip",
  "zstd",
@@ -1284,9 +1279,9 @@ dependencies = [
 
 [[package]]
 name = "deno_ast"
-version = "0.42.2"
+version = "0.43.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b2b9d03b1bbeeecdac54367f075d572131736d06c5be3bc49037855bc5ab1bbb"
+checksum = "48d00b724e06d2081a141ec1155756a0b465d413d8e2a7515221f61d482eb2ee"
 dependencies = [
  "base64 0.21.7",
  "deno_media_type",
@@ -1328,7 +1323,7 @@ dependencies = [
 
 [[package]]
 name = "deno_bench_util"
-version = "0.167.0"
+version = "0.171.0"
 dependencies = [
  "bencher",
  "deno_core",
@@ -1337,7 +1332,7 @@ dependencies = [
 
 [[package]]
 name = "deno_broadcast_channel"
-version = "0.167.0"
+version = "0.171.0"
 dependencies = [
  "async-trait",
  "deno_core",
@@ -1348,7 +1343,7 @@ dependencies = [
 
 [[package]]
 name = "deno_cache"
-version = "0.105.0"
+version = "0.109.0"
 dependencies = [
  "async-trait",
  "deno_core",
@@ -1361,9 +1356,9 @@ dependencies = [
 
 [[package]]
 name = "deno_cache_dir"
-version = "0.13.0"
+version = "0.13.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "186a102b13b4512841f5f40784cd25822042d22954afe3b5b070d406d15eb4f2"
+checksum = "08c1f52170cd7715f8006da54cde1444863a0d6fbd9c11d037a737db2dec8e22"
 dependencies = [
  "base32",
  "deno_media_type",
@@ -1381,7 +1376,7 @@ dependencies = [
 
 [[package]]
 name = "deno_canvas"
-version = "0.42.0"
+version = "0.46.0"
 dependencies = [
  "deno_core",
  "deno_webgpu",
@@ -1392,9 +1387,9 @@ dependencies = [
 
 [[package]]
 name = "deno_config"
-version = "0.37.1"
+version = "0.38.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "3cb7a1723676fba5964f8d7441d8b53748f9e74d6d4241be7de9730da021859a"
+checksum = "966825073480a6ac7e01977a3879d13edc8d6ea2d65ea164b37156a5fb206e9a"
 dependencies = [
  "anyhow",
  "deno_package_json",
@@ -1416,16 +1411,16 @@ dependencies = [
 
 [[package]]
 name = "deno_console"
-version = "0.173.0"
+version = "0.177.0"
 dependencies = [
  "deno_core",
 ]
 
 [[package]]
 name = "deno_core"
-version = "0.314.2"
+version = "0.318.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "83138917579676069b423c3eb9be3c1e579f60dc022d85f6ded4c792456255ff"
+checksum = "10cae2393219ff9278123f7b24799cdfab37c7d6561b69ca06ced115cac92111"
 dependencies = [
  "anyhow",
  "bincode",
@@ -1461,7 +1456,7 @@ checksum = "a13951ea98c0a4c372f162d669193b4c9d991512de9f2381dd161027f34b26b1"
 
 [[package]]
 name = "deno_cron"
-version = "0.53.0"
+version = "0.57.0"
 dependencies = [
  "anyhow",
  "async-trait",
@@ -1474,7 +1469,7 @@ dependencies = [
 
 [[package]]
 name = "deno_crypto"
-version = "0.187.0"
+version = "0.191.0"
 dependencies = [
  "aes",
  "aes-gcm",
@@ -1511,9 +1506,9 @@ dependencies = [
 
 [[package]]
 name = "deno_doc"
-version = "0.154.0"
+version = "0.156.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "17e204e45b0d79750880114e37b34abe19ad0710d8435a8da8f23a528fe98de4"
+checksum = "2585b98d6ad76dae30bf2d7b6d71b8363cae041158b8780d14a2f4fe17590a61"
 dependencies = [
  "anyhow",
  "cfg-if",
@@ -1536,7 +1531,7 @@ dependencies = [
 
 [[package]]
 name = "deno_fetch"
-version = "0.197.0"
+version = "0.201.0"
 dependencies = [
  "base64 0.21.7",
  "bytes",
@@ -1569,7 +1564,7 @@ dependencies = [
 
 [[package]]
 name = "deno_ffi"
-version = "0.160.0"
+version = "0.164.0"
 dependencies = [
  "deno_core",
  "deno_permissions",
@@ -1578,6 +1573,7 @@ dependencies = [
  "libffi",
  "libffi-sys",
  "log",
+ "num-bigint",
  "serde",
  "serde-value",
  "serde_json",
@@ -1588,7 +1584,7 @@ dependencies = [
 
 [[package]]
 name = "deno_fs"
-version = "0.83.0"
+version = "0.87.0"
 dependencies = [
  "async-trait",
  "base32",
@@ -1610,9 +1606,9 @@ dependencies = [
 
 [[package]]
 name = "deno_graph"
-version = "0.83.3"
+version = "0.84.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "77163c46755676d8f793fc19e365537ba660a8db173cd1e02d21eb010c0b3cef"
+checksum = "cd4f4a14aa069087be41c2998077b0453f0191747898f96e6343f700abfc2c18"
 dependencies = [
  "anyhow",
  "async-trait",
@@ -1639,7 +1635,7 @@ dependencies = [
 
 [[package]]
 name = "deno_http"
-version = "0.171.0"
+version = "0.175.0"
 dependencies = [
  "async-compression",
  "async-trait",
@@ -1678,7 +1674,7 @@ dependencies = [
 
 [[package]]
 name = "deno_io"
-version = "0.83.0"
+version = "0.87.0"
 dependencies = [
  "async-trait",
  "deno_core",
@@ -1699,7 +1695,7 @@ dependencies = [
 
 [[package]]
 name = "deno_kv"
-version = "0.81.0"
+version = "0.85.0"
 dependencies = [
  "anyhow",
  "async-trait",
@@ -1730,9 +1726,9 @@ dependencies = [
 
 [[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",
@@ -1760,9 +1756,9 @@ 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",
@@ -1771,12 +1767,17 @@ dependencies = [
 
 [[package]]
 name = "deno_napi"
-version = "0.104.0"
+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]]
@@ -1794,24 +1795,24 @@ dependencies = [
 
 [[package]]
 name = "deno_net"
-version = "0.165.0"
+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 = "0.110.0"
+version = "0.114.0"
 dependencies = [
  "aead-gcm-stream",
  "aes",
@@ -1920,9 +1921,9 @@ dependencies = [
 
 [[package]]
 name = "deno_ops"
-version = "0.190.1"
+version = "0.194.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "26f46d4e4f52f26c882b74a9b58810ea75252b807cf0966166ec333077cdfd85"
+checksum = "f760b492bd638c1dc3e992d11672c259fbe9a233162099a8347591c9e22d0391"
 dependencies = [
  "proc-macro-rules",
  "proc-macro2",
@@ -1960,7 +1961,7 @@ dependencies = [
 
 [[package]]
 name = "deno_permissions"
-version = "0.33.0"
+version = "0.37.0"
 dependencies = [
  "deno_core",
  "deno_path_util",
@@ -1971,13 +1972,14 @@ dependencies = [
  "once_cell",
  "percent-encoding",
  "serde",
+ "thiserror",
  "which 4.4.2",
  "winapi",
 ]
 
 [[package]]
 name = "deno_resolver"
-version = "0.5.0"
+version = "0.9.0"
 dependencies = [
  "anyhow",
  "base32",
@@ -1993,7 +1995,7 @@ dependencies = [
 
 [[package]]
 name = "deno_runtime"
-version = "0.182.0"
+version = "0.186.0"
 dependencies = [
  "color-print",
  "deno_ast",
@@ -2043,11 +2045,13 @@ dependencies = [
  "percent-encoding",
  "regex",
  "rustyline",
+ "same-file",
  "serde",
  "signal-hook",
  "signal-hook-registry",
  "tempfile",
  "test_server",
+ "thiserror",
  "tokio",
  "tokio-metrics",
  "twox-hash",
@@ -2059,9 +2063,9 @@ dependencies = [
 
 [[package]]
 name = "deno_semver"
-version = "0.5.14"
+version = "0.5.16"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "670fec7ef309384e23c2a90ac5d2d9d91a776d225306c75f5cdd28cf6cc8a59f"
+checksum = "c957c6a57c38b7dde2315df0da0ec228911e56a74f185b108a488d0401841a67"
 dependencies = [
  "monch",
  "once_cell",
@@ -2109,7 +2113,7 @@ dependencies = [
 
 [[package]]
 name = "deno_tls"
-version = "0.160.0"
+version = "0.164.0"
 dependencies = [
  "deno_core",
  "deno_native_certs",
@@ -2158,7 +2162,7 @@ dependencies = [
 
 [[package]]
 name = "deno_url"
-version = "0.173.0"
+version = "0.177.0"
 dependencies = [
  "deno_bench_util",
  "deno_console",
@@ -2170,7 +2174,7 @@ dependencies = [
 
 [[package]]
 name = "deno_web"
-version = "0.204.0"
+version = "0.208.0"
 dependencies = [
  "async-trait",
  "base64-simd 0.8.0",
@@ -2192,7 +2196,7 @@ dependencies = [
 
 [[package]]
 name = "deno_webgpu"
-version = "0.140.0"
+version = "0.144.0"
 dependencies = [
  "deno_core",
  "raw-window-handle",
@@ -2205,7 +2209,7 @@ dependencies = [
 
 [[package]]
 name = "deno_webidl"
-version = "0.173.0"
+version = "0.177.0"
 dependencies = [
  "deno_bench_util",
  "deno_core",
@@ -2213,7 +2217,7 @@ dependencies = [
 
 [[package]]
 name = "deno_websocket"
-version = "0.178.0"
+version = "0.182.0"
 dependencies = [
  "bytes",
  "deno_core",
@@ -2235,7 +2239,7 @@ dependencies = [
 
 [[package]]
 name = "deno_webstorage"
-version = "0.168.0"
+version = "0.172.0"
 dependencies = [
  "deno_core",
  "deno_web",
@@ -2563,9 +2567,9 @@ 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",
@@ -2577,9 +2581,9 @@ 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",
@@ -2605,9 +2609,9 @@ 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",
@@ -2635,15 +2639,6 @@ 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"
@@ -2891,29 +2886,6 @@ version = "1.0.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "31ae425815400e5ed474178a7a22e275a9687086a12ca63ec793ff292d8fdae8"
 
-[[package]]
-name = "eszip"
-version = "0.79.1"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "8eb55c89bdde75a3826a79d49c9d847623ae7fbdb2695b542982982da990d33e"
-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"
@@ -3525,15 +3497,6 @@ 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"
@@ -3573,6 +3536,92 @@ 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"
@@ -4034,9 +4083,9 @@ 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",
 ]
@@ -4223,9 +4272,9 @@ dependencies = [
 
 [[package]]
 name = "libsui"
-version = "0.4.0"
+version = "0.5.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "205eca4e7beaad637dcd38fe41292065894ee7f498077cf3c135d5f7252b9f27"
+checksum = "89795977654ad6250d6c0915411b622bac22f9efb4f852af94b2e00964cab832"
 dependencies = [
  "editpe",
  "libc",
@@ -4327,9 +4376,9 @@ 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",
@@ -4340,9 +4389,9 @@ dependencies = [
 
 [[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",
@@ -4512,7 +4561,7 @@ dependencies = [
 
 [[package]]
 name = "napi_sym"
-version = "0.103.0"
+version = "0.107.0"
 dependencies = [
  "quote",
  "serde",
@@ -4567,7 +4616,7 @@ dependencies = [
 
 [[package]]
 name = "node_resolver"
-version = "0.12.0"
+version = "0.16.0"
 dependencies = [
  "anyhow",
  "async-trait",
@@ -5811,7 +5860,7 @@ dependencies = [
  "bitflags 2.6.0",
  "fallible-iterator",
  "fallible-streaming-iterator",
- "hashlink 0.9.1",
+ "hashlink",
  "libsqlite3-sys",
  "smallvec",
 ]
@@ -6175,15 +6224,6 @@ 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"
@@ -6198,9 +6238,9 @@ dependencies = [
 
 [[package]]
 name = "serde_v8"
-version = "0.223.1"
+version = "0.227.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "9cf3d859dda87ee96423c01244f10af864fa6d6a9fcdc2b77e0595078ea0ea11"
+checksum = "0a8294c2223c53bed343be8b80564ece4dc0d03b643b06fa86c4ccc0e064eda0"
 dependencies = [
  "num-bigint",
  "serde",
@@ -7150,6 +7190,7 @@ dependencies = [
  "console_static_text",
  "deno_unsync",
  "denokv_proto",
+ "faster-hex",
  "fastwebsockets",
  "flate2",
  "futures",
@@ -7397,40 +7438,6 @@ dependencies = [
  "serde",
 ]
 
-[[package]]
-name = "toml"
-version = "0.7.8"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "dd79e69d3b627db300ff956027cc6c3798cef26d22526befdfcd12feeb6d2257"
-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",
-]
-
 [[package]]
 name = "tower"
 version = "0.4.13"
@@ -7520,95 +7527,6 @@ 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"
@@ -8358,15 +8276,6 @@ 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"
@@ -8402,7 +8311,7 @@ version = "0.1.12"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "b68db261ef59e9e52806f688020631e987592bd83619edccda9c47d42cde4f6c"
 dependencies = [
- "toml 0.5.11",
+ "toml",
 ]
 
 [[package]]
@@ -8479,7 +8388,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "2a6a39b6b5ba0d02c910d05d7fbc366a4befb8901ea107dcde9c1c97acb8a366"
 dependencies = [
  "rowan",
- "winnow 0.6.15",
+ "winnow",
 ]
 
 [[package]]
diff --git a/Cargo.toml b/Cargo.toml
index 9f15d03a54..d83ca2e413 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",
@@ -19,6 +18,7 @@ members = [
   "ext/io",
   "ext/kv",
   "ext/napi",
+  "ext/napi/sym",
   "ext/net",
   "ext/node",
   "ext/url",
@@ -45,19 +45,19 @@ license = "MIT"
 repository = "https://github.com/denoland/deno"
 
 [workspace.dependencies]
-deno_ast = { version = "=0.42.2", features = ["transpiling"] }
-deno_core = { version = "0.314.2" }
+deno_ast = { version = "=0.43.3", features = ["transpiling"] }
+deno_core = { version = "0.318.0" }
 
-deno_bench_util = { version = "0.167.0", path = "./bench_util" }
+deno_bench_util = { version = "0.171.0", path = "./bench_util" }
 deno_lockfile = "=0.23.1"
-deno_media_type = { version = "0.1.4", features = ["module_specifier"] }
+deno_media_type = { version = "0.2.0", features = ["module_specifier"] }
 deno_npm = "=0.25.4"
 deno_path_util = "=0.2.1"
-deno_permissions = { version = "0.33.0", path = "./runtime/permissions" }
-deno_runtime = { version = "0.182.0", path = "./runtime" }
-deno_semver = "=0.5.14"
+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 = "0.103.0", 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"
@@ -66,32 +66,32 @@ denokv_remote = "0.8.1"
 denokv_sqlite = { default-features = false, version = "0.8.2" }
 
 # exts
-deno_broadcast_channel = { version = "0.167.0", path = "./ext/broadcast_channel" }
-deno_cache = { version = "0.105.0", path = "./ext/cache" }
-deno_canvas = { version = "0.42.0", path = "./ext/canvas" }
-deno_console = { version = "0.173.0", path = "./ext/console" }
-deno_cron = { version = "0.53.0", path = "./ext/cron" }
-deno_crypto = { version = "0.187.0", path = "./ext/crypto" }
-deno_fetch = { version = "0.197.0", path = "./ext/fetch" }
-deno_ffi = { version = "0.160.0", path = "./ext/ffi" }
-deno_fs = { version = "0.83.0", path = "./ext/fs" }
-deno_http = { version = "0.171.0", path = "./ext/http" }
-deno_io = { version = "0.83.0", path = "./ext/io" }
-deno_kv = { version = "0.81.0", path = "./ext/kv" }
-deno_napi = { version = "0.104.0", path = "./ext/napi" }
-deno_net = { version = "0.165.0", path = "./ext/net" }
-deno_node = { version = "0.110.0", path = "./ext/node" }
-deno_tls = { version = "0.160.0", path = "./ext/tls" }
-deno_url = { version = "0.173.0", path = "./ext/url" }
-deno_web = { version = "0.204.0", path = "./ext/web" }
-deno_webgpu = { version = "0.140.0", path = "./ext/webgpu" }
-deno_webidl = { version = "0.173.0", path = "./ext/webidl" }
-deno_websocket = { version = "0.178.0", path = "./ext/websocket" }
-deno_webstorage = { version = "0.168.0", path = "./ext/webstorage" }
+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 = "0.5.0", path = "./resolvers/deno" }
-node_resolver = { version = "0.12.0", path = "./resolvers/node" }
+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"
@@ -111,7 +111,7 @@ console_static_text = "=0.8.1"
 dashmap = "5.5.3"
 data-encoding = "2.3.3"
 data-url = "=0.3.0"
-deno_cache_dir = "=0.13.0"
+deno_cache_dir = "=0.13.2"
 deno_package_json = { version = "0.1.2", default-features = false }
 dlopen2 = "0.6.1"
 ecb = "=0.1.2"
@@ -137,7 +137,7 @@ 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 = "1.1.20", default-features = false }
@@ -187,7 +187,7 @@ 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"
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 08562134a1..5ce25815bd 100644
--- a/Releases.md
+++ b/Releases.md
@@ -6,6 +6,124 @@ 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)
diff --git a/bench_util/Cargo.toml b/bench_util/Cargo.toml
index fbf30b9fcf..d6eefc3a5d 100644
--- a/bench_util/Cargo.toml
+++ b/bench_util/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_bench_util"
-version = "0.167.0"
+version = "0.171.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/cli/Cargo.toml b/cli/Cargo.toml
index 7d6fc71622..e98e0ac001 100644
--- a/cli/Cargo.toml
+++ b/cli/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno"
-version = "2.0.2"
+version = "2.0.6"
 authors.workspace = true
 default-run = "deno"
 edition.workspace = true
@@ -70,11 +70,11 @@ 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 = "=0.37.1", features = ["workspace", "sync"] }
+deno_config = { version = "=0.38.2", features = ["workspace", "sync"] }
 deno_core = { workspace = true, features = ["include_js_files_for_snapshotting"] }
-deno_doc = { version = "0.154.0", default-features = false, features = ["rust", "html", "syntect"] }
-deno_graph = { version = "=0.83.3" }
-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.workspace = true
 deno_package_json.workspace = true
@@ -84,9 +84,7 @@ deno_runtime = { workspace = true, features = ["include_js_files_for_snapshottin
 deno_semver.workspace = true
 deno_task_shell = "=0.18.1"
 deno_terminal.workspace = true
-eszip = "=0.79.1"
-libsui = "0.4.0"
-napi_sym.workspace = true
+libsui = "0.5.0"
 node_resolver.workspace = true
 
 anstream = "0.6.14"
@@ -106,10 +104,10 @@ 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
@@ -123,15 +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
+jsonc-parser = { workspace = true, features = ["cst", "serde"] }
 jupyter_runtime = { package = "runtimelib", version = "=0.14.0" }
 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
@@ -168,7 +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
@@ -176,14 +173,12 @@ zstd.workspace = true
 [target.'cfg(windows)'.dependencies]
 junction.workspace = true
 winapi = { workspace = true, features = ["knownfolders", "mswsock", "objbase", "shlobj", "tlhelp32", "winbase", "winerror", "winsock2"] }
-windows-sys.workspace = true
 
 [target.'cfg(unix)'.dependencies]
 nix.workspace = true
 
 [dev-dependencies]
 deno_bench_util.workspace = true
-libuv-sys-lite = "=1.48.2"
 pretty_assertions.workspace = true
 test_util.workspace = true
 
diff --git a/cli/args/flags.rs b/cli/args/flags.rs
index cb3d55e50d..eb77971748 100644
--- a/cli/args/flags.rs
+++ b/cli/args/flags.rs
@@ -1179,8 +1179,8 @@ static DENO_HELP: &str = cstr!(
   <y>Dependency management:</>
     <g>add</>          Add dependencies
                   <p(245)>deno add jsr:@std/assert  |  deno add npm:express</>
-    <g>install</>      Install script as an executable
-    <g>uninstall</>    Uninstall a script previously installed with deno install
+    <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:</>
@@ -1856,6 +1856,7 @@ 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())
       }
     )
@@ -2273,7 +2274,7 @@ 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")
@@ -3387,8 +3388,7 @@ 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)
         }
@@ -4373,6 +4373,7 @@ 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;
@@ -6800,6 +6801,32 @@ 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]
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/mod.rs b/cli/args/mod.rs
index f905e186ba..e19025f8b1 100644
--- a/cli/args/mod.rs
+++ b/cli/args/mod.rs
@@ -46,6 +46,7 @@ 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;
@@ -200,6 +201,8 @@ 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,
@@ -578,6 +581,7 @@ 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))
   }
 
@@ -963,6 +967,9 @@ 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(),
     }
   }
@@ -1448,6 +1455,12 @@ 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 {
@@ -1591,6 +1604,15 @@ 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
@@ -1668,6 +1690,10 @@ 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)));
diff --git a/cli/args/package_json.rs b/cli/args/package_json.rs
index 2ef39a30d2..7dc75550c3 100644
--- a/cli/args/package_json.rs
+++ b/cli/args/package_json.rs
@@ -5,10 +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 {
@@ -23,11 +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<PackageJsonDepValueParseError>,
+  pkg_json_dep_errors: Vec<PackageJsonDepValueParseWithLocationError>,
 }
 
 impl NpmInstallDepsProvider {
@@ -89,7 +100,13 @@ impl NpmInstallDepsProvider {
           let dep = match dep {
             Ok(dep) => dep,
             Err(err) => {
-              pkg_json_dep_errors.push(err);
+              pkg_json_dep_errors.push(
+                PackageJsonDepValueParseWithLocationError {
+                  location: pkg_json.specifier(),
+                  alias,
+                  source: err,
+                },
+              );
               continue;
             }
           };
@@ -150,7 +167,9 @@ impl NpmInstallDepsProvider {
     &self.workspace_pkgs
   }
 
-  pub fn pkg_json_dep_errors(&self) -> &[PackageJsonDepValueParseError] {
+  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/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 aa5d3d18c6..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();
@@ -374,58 +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",
-    );
-
-  println!("cargo:rustc-rerun-if-changed={}", symbols_path.display());
-
-  #[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/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 ded163b4e4..50fc135ddf 100644
--- a/cli/cache/mod.rs
+++ b/cli/cache/mod.rs
@@ -8,14 +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::resolver::CliNodeResolver;
 use crate::util::fs::atomic_write_file_with_retries;
 use crate::util::fs::atomic_write_file_with_retries_and_fs;
 use crate::util::fs::AtomicWriteFileFsAdapter;
-use crate::util::path::specifier_has_extension;
-use crate::util::text_encoding::arc_str_to_bytes;
-use crate::util::text_encoding::from_utf8_lossy_owned;
 
 use deno_ast::MediaType;
 use deno_core::futures;
@@ -25,7 +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;
@@ -60,7 +57,6 @@ pub use fast_check::FastCheckCache;
 pub use incremental::IncrementalCache;
 pub use module_info::ModuleInfoCache;
 pub use node::NodeAnalysisCache;
-pub use parsed_source::EsmOrCjsChecker;
 pub use parsed_source::LazyGraphSourceParser;
 pub use parsed_source::ParsedSourceCache;
 
@@ -181,46 +177,40 @@ pub struct FetchCacherOptions {
   pub permissions: PermissionsContainer,
   /// If we're publishing for `deno publish`.
   pub is_deno_publish: bool,
-  pub unstable_detect_cjs: bool,
 }
 
 /// 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 {
   pub file_header_overrides: HashMap<ModuleSpecifier, HashMap<String, String>>,
-  esm_or_cjs_checker: Arc<EsmOrCjsChecker>,
   file_fetcher: Arc<FileFetcher>,
+  fs: Arc<dyn deno_fs::FileSystem>,
   global_http_cache: Arc<GlobalHttpCache>,
-  node_resolver: Arc<CliNodeResolver>,
-  npm_resolver: Arc<dyn CliNpmResolver>,
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
   module_info_cache: Arc<ModuleInfoCache>,
   permissions: PermissionsContainer,
   is_deno_publish: bool,
-  unstable_detect_cjs: bool,
   cache_info_enabled: bool,
 }
 
 impl FetchCacher {
   pub fn new(
-    esm_or_cjs_checker: Arc<EsmOrCjsChecker>,
     file_fetcher: Arc<FileFetcher>,
+    fs: Arc<dyn deno_fs::FileSystem>,
     global_http_cache: Arc<GlobalHttpCache>,
-    node_resolver: Arc<CliNodeResolver>,
-    npm_resolver: Arc<dyn CliNpmResolver>,
+    in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
     module_info_cache: Arc<ModuleInfoCache>,
     options: FetchCacherOptions,
   ) -> Self {
     Self {
       file_fetcher,
-      esm_or_cjs_checker,
+      fs,
       global_http_cache,
-      node_resolver,
-      npm_resolver,
+      in_npm_pkg_checker,
       module_info_cache,
       file_header_overrides: options.file_header_overrides,
       permissions: options.permissions,
       is_deno_publish: options.is_deno_publish,
-      unstable_detect_cjs: options.unstable_detect_cjs,
       cache_info_enabled: false,
     }
   }
@@ -271,70 +261,23 @@ 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 },
         ))));
       }
-
-      if self.unstable_detect_cjs && specifier_has_extension(specifier, "js") {
-        if let Ok(Some(pkg_json)) =
-          self.node_resolver.get_closest_package_json(specifier)
-        {
-          if pkg_json.typ == "commonjs" {
-            if let Ok(path) = specifier.to_file_path() {
-              if let Ok(bytes) = std::fs::read(&path) {
-                let text: Arc<str> = from_utf8_lossy_owned(bytes).into();
-                let is_es_module = match self.esm_or_cjs_checker.is_esm(
-                  specifier,
-                  text.clone(),
-                  MediaType::JavaScript,
-                ) {
-                  Ok(value) => value,
-                  Err(err) => {
-                    return Box::pin(futures::future::ready(Err(err.into())));
-                  }
-                };
-                if !is_es_module {
-                  self.node_resolver.mark_cjs_resolution(specifier.clone());
-                  return Box::pin(futures::future::ready(Ok(Some(
-                    LoadResponse::External {
-                      specifier: specifier.clone(),
-                    },
-                  ))));
-                } else {
-                  return Box::pin(futures::future::ready(Ok(Some(
-                    LoadResponse::Module {
-                      specifier: specifier.clone(),
-                      content: arc_str_to_bytes(text),
-                      maybe_headers: None,
-                    },
-                  ))));
-                }
-              }
-            }
-          }
-        }
-      }
     }
 
     if self.is_deno_publish
@@ -378,6 +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 df6e45c35e..7e819ae998 100644
--- a/cli/cache/parsed_source.rs
+++ b/cli/cache/parsed_source.rs
@@ -5,12 +5,11 @@ use std::sync::Arc;
 
 use deno_ast::MediaType;
 use deno_ast::ModuleSpecifier;
-use deno_ast::ParseDiagnostic;
 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;
 
@@ -47,7 +46,7 @@ impl<'a> LazyGraphSourceParser<'a> {
   }
 }
 
-#[derive(Default)]
+#[derive(Debug, Default)]
 pub struct ParsedSourceCache {
   sources: Mutex<HashMap<ModuleSpecifier, ParsedSource>>,
 }
@@ -58,12 +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,
     })
   }
@@ -87,10 +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.
@@ -100,8 +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)
   }
 }
 
@@ -150,42 +147,3 @@ impl deno_graph::ParsedSourceStore for ParsedSourceCache {
     }
   }
 }
-
-pub struct EsmOrCjsChecker {
-  parsed_source_cache: Arc<ParsedSourceCache>,
-}
-
-impl EsmOrCjsChecker {
-  pub fn new(parsed_source_cache: Arc<ParsedSourceCache>) -> Self {
-    Self {
-      parsed_source_cache,
-    }
-  }
-
-  pub fn is_esm(
-    &self,
-    specifier: &ModuleSpecifier,
-    source: Arc<str>,
-    media_type: MediaType,
-  ) -> Result<bool, ParseDiagnostic> {
-    // todo(dsherret): add a file cache here to avoid parsing with swc on each run
-    let source = match self.parsed_source_cache.get_parsed_source(specifier) {
-      Some(source) => source.clone(),
-      None => {
-        let source = deno_ast::parse_program(deno_ast::ParseParams {
-          specifier: specifier.clone(),
-          text: source,
-          media_type,
-          capture_tokens: true, // capture because it's used for cjs export analysis
-          scope_analysis: false,
-          maybe_syntax: None,
-        })?;
-        self
-          .parsed_source_cache
-          .set_parsed_source(specifier.clone(), source.clone());
-        source
-      }
-    };
-    Ok(source.is_module())
-  }
-}
diff --git a/cli/emit.rs b/cli/emit.rs
index b3f4a4477a..8c4f2091cf 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)
       }
     }
   }
@@ -169,6 +181,7 @@ impl Emitter {
   pub async fn load_and_emit_for_hmr(
     &self,
     specifier: &ModuleSpecifier,
+    module_kind: deno_ast::ModuleKind,
   ) -> Result<String, AnyError> {
     let media_type = MediaType::from_specifier(specifier);
     let source_code = tokio::fs::read_to_string(
@@ -191,9 +204,14 @@ impl Emitter {
         let mut options = self.transpile_and_emit_options.1.clone();
         options.source_map = SourceMapOption::None;
         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(module_kind),
+            },
+            &options,
+          )?
+          .into_source();
         Ok(transpiled_source.text)
       }
       MediaType::JavaScript
@@ -204,7 +222,7 @@ 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 +235,17 @@ 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 +256,15 @@ 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 +273,24 @@ 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 +299,20 @@ 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 +344,7 @@ 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 25f3551102..4a36c75ba2 100644
--- a/cli/factory.rs
+++ b/cli/factory.rs
@@ -11,10 +11,10 @@ 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;
-use crate::cache::EsmOrCjsChecker;
 use crate::cache::GlobalHttpCache;
 use crate::cache::HttpCache;
 use crate::cache::LocalHttpCache;
@@ -33,12 +33,16 @@ 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::CliNpmResolverCreateOptions;
-use crate::npm::CliNpmResolverManagedCreateOptions;
 use crate::npm::CliNpmResolverManagedSnapshotOption;
-use crate::resolver::CjsResolutionStore;
+use crate::npm::CreateInNpmPkgCheckerOptions;
+use crate::resolver::CjsTracker;
+use crate::resolver::CjsTrackerOptions;
 use crate::resolver::CliDenoResolverFs;
 use crate::resolver::CliGraphResolver;
 use crate::resolver::CliGraphResolverOptions;
@@ -51,6 +55,7 @@ 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;
@@ -59,6 +64,7 @@ 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;
@@ -68,6 +74,7 @@ use deno_core::FeatureChecker;
 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;
@@ -77,6 +84,7 @@ 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;
@@ -164,39 +172,41 @@ 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_node_resolver: Deferred<Arc<CliNodeResolver>>,
+  cli_options: Deferred<Arc<CliOptions>>,
+  code_cache: Deferred<Arc<CodeCache>>,
+  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>>,
-  esm_or_cjs_checker: Deferred<Arc<EsmOrCjsChecker>>,
-  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_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<CliGraphResolver>>,
+  root_cert_store_provider: Deferred<Arc<dyn RootCertStoreProvider>>,
   root_permissions_container: Deferred<PermissionsContainer>,
   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>>,
 }
 
@@ -300,12 +310,6 @@ impl CliFactory {
       .get_or_init(|| ProgressBar::new(ProgressBarStyle::TextOnly))
   }
 
-  pub fn esm_or_cjs_checker(&self) -> &Arc<EsmOrCjsChecker> {
-    self.services.esm_or_cjs_checker.get_or_init(|| {
-      Arc::new(EsmOrCjsChecker::new(self.parsed_source_cache().clone()))
-    })
-  }
-
   pub fn global_http_cache(&self) -> Result<&Arc<GlobalHttpCache>, AnyError> {
     self.services.global_http_cache.get_or_try_init(|| {
       Ok(Arc::new(GlobalHttpCache::new(
@@ -359,56 +363,112 @@ 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(CliByonmNpmResolverCreateOptions {
-            fs: CliDenoResolverFs(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
   }
 
@@ -513,6 +573,7 @@ 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(),
       )))
     })
   }
@@ -541,6 +602,7 @@ 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,
@@ -564,7 +626,9 @@ impl CliFactory {
         async {
           Ok(Arc::new(NodeResolver::new(
             DenoFsNodeResolverEnv::new(self.fs().clone()),
+            self.in_npm_pkg_checker()?.clone(),
             self.npm_resolver().await?.clone().into_npm_resolver(),
+            self.pkg_json_resolver().clone(),
           )))
         }
         .boxed_local(),
@@ -582,24 +646,35 @@ 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()),
+          self.cli_options()?.is_npm_main(),
         );
 
         Ok(Arc::new(NodeCodeTranslator::new(
           cjs_esm_analyzer,
           DenoFsNodeResolverEnv::new(self.fs().clone()),
-          self.node_resolver().await?.clone(),
+          self.in_npm_pkg_checker()?.clone(),
+          node_resolver,
           self.npm_resolver().await?.clone().into_npm_resolver(),
+          self.pkg_json_resolver().clone(),
         )))
       })
       .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
@@ -608,6 +683,10 @@ 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(),
@@ -626,19 +705,18 @@ 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.esm_or_cjs_checker().clone(),
+          cli_options.clone(),
+          self.file_fetcher()?.clone(),
           self.fs().clone(),
-          self.resolver().await?.clone(),
-          self.cli_node_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(),
         )))
       })
@@ -710,8 +788,17 @@ impl CliFactory {
       .await
   }
 
-  pub fn cjs_resolutions(&self) -> &Arc<CjsResolutionStore> {
-    self.services.cjs_resolutions.get_or_init(Default::default)
+  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(),
+        CjsTrackerOptions {
+          unstable_detect_cjs: options.unstable_detect_cjs(),
+        },
+      )))
+    })
   }
 
   pub async fn cli_node_resolver(
@@ -722,8 +809,9 @@ impl CliFactory {
       .cli_node_resolver
       .get_or_try_init_async(async {
         Ok(Arc::new(CliNodeResolver::new(
-          self.cjs_resolutions().clone(),
+          self.cjs_tracker()?.clone(),
           self.fs().clone(),
+          self.in_npm_pkg_checker()?.clone(),
           self.node_resolver().await?.clone(),
           self.npm_resolver().await?.clone(),
         )))
@@ -761,7 +849,9 @@ 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(),
@@ -790,53 +880,60 @@ 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();
 
     Ok(CliMainWorkerFactory::new(
       self.blob_store().clone(),
-      self.cjs_resolutions().clone(),
       if cli_options.code_cache_enabled() {
         Some(self.code_cache()?.clone())
       } else {
         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(),
+        node_code_translator.clone(),
         cli_node_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(),
+      pkg_json_resolver,
       self.root_cert_store_provider().clone(),
       self.root_permissions_container()?.clone(),
       StorageKeyResolver::from_options(cli_options),
@@ -852,8 +949,10 @@ impl CliFactory {
     let create_hmr_runner = if cli_options.has_hmr() {
       let watcher_communicator = self.watcher_communicator.clone().unwrap();
       let emitter = self.emitter()?.clone();
+      let cjs_tracker = self.cjs_tracker()?.clone();
       let fn_: crate::worker::CreateHmrRunnerCb = Box::new(move |session| {
         Box::new(HmrRunner::new(
+          cjs_tracker.clone(),
           emitter.clone(),
           session,
           watcher_communicator.clone(),
@@ -890,7 +989,6 @@ 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
@@ -908,7 +1006,6 @@ impl CliFactory {
       node_ipc: cli_options.node_ipc_fd(),
       serve_port: cli_options.serve_port(),
       serve_host: cli_options.serve_host(),
-      unstable_detect_cjs: cli_options.unstable_detect_cjs(),
     })
   }
 }
diff --git a/cli/file_fetcher.rs b/cli/file_fetcher.rs
index e92aca5420..95d778f0bb 100644
--- a/cli/file_fetcher.rs
+++ b/cli/file_fetcher.rs
@@ -24,6 +24,7 @@ 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 http::header;
 use log::debug;
 use std::borrow::Cow;
 use std::collections::HashMap;
@@ -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>,
 }
@@ -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
     }
@@ -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),
         },
@@ -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),
         },
diff --git a/cli/graph_util.rs b/cli/graph_util.rs
index e67ae7821b..46257cf785 100644
--- a/cli/graph_util.rs
+++ b/cli/graph_util.rs
@@ -6,7 +6,6 @@ use crate::args::CliLockfile;
 use crate::args::CliOptions;
 use crate::args::DENO_DISABLE_PEDANTIC_NODE_WARNINGS;
 use crate::cache;
-use crate::cache::EsmOrCjsChecker;
 use crate::cache::GlobalHttpCache;
 use crate::cache::ModuleInfoCache;
 use crate::cache::ParsedSourceCache;
@@ -15,7 +14,6 @@ use crate::errors::get_error_class_name;
 use crate::file_fetcher::FileFetcher;
 use crate::npm::CliNpmResolver;
 use crate::resolver::CliGraphResolver;
-use crate::resolver::CliNodeResolver;
 use crate::resolver::CliSloppyImportsResolver;
 use crate::resolver::SloppyImportsCachedFs;
 use crate::tools::check;
@@ -50,6 +48,7 @@ use deno_runtime::deno_permissions::PermissionsContainer;
 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;
@@ -379,54 +378,51 @@ pub struct BuildFastCheckGraphOptions<'a> {
 }
 
 pub struct ModuleGraphBuilder {
-  options: Arc<CliOptions>,
   caches: Arc<cache::Caches>,
-  esm_or_cjs_checker: Arc<EsmOrCjsChecker>,
+  cli_options: Arc<CliOptions>,
+  file_fetcher: Arc<FileFetcher>,
   fs: Arc<dyn FileSystem>,
-  resolver: Arc<CliGraphResolver>,
-  node_resolver: Arc<CliNodeResolver>,
-  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<CliGraphResolver>,
   root_permissions_container: PermissionsContainer,
 }
 
 impl ModuleGraphBuilder {
   #[allow(clippy::too_many_arguments)]
   pub fn new(
-    options: Arc<CliOptions>,
     caches: Arc<cache::Caches>,
-    esm_or_cjs_checker: Arc<EsmOrCjsChecker>,
+    cli_options: Arc<CliOptions>,
+    file_fetcher: Arc<FileFetcher>,
     fs: Arc<dyn FileSystem>,
-    resolver: Arc<CliGraphResolver>,
-    node_resolver: Arc<CliNodeResolver>,
-    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<CliGraphResolver>,
     root_permissions_container: PermissionsContainer,
   ) -> Self {
     Self {
-      options,
       caches,
-      esm_or_cjs_checker,
+      cli_options,
+      file_fetcher,
       fs,
-      resolver,
-      node_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,
     }
   }
@@ -512,13 +508,11 @@ 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()),
@@ -566,7 +560,7 @@ 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)
@@ -677,10 +671,10 @@ impl ModuleGraphBuilder {
 
     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),
+        jsr_url_provider: &CliJsrUrlProvider,
         resolver: Some(graph_resolver),
         npm_resolver: Some(&graph_npm_resolver),
         workspace_fast_check: options.workspace_fast_check,
@@ -699,20 +693,18 @@ impl ModuleGraphBuilder {
     permissions: PermissionsContainer,
   ) -> cache::FetchCacher {
     cache::FetchCacher::new(
-      self.esm_or_cjs_checker.clone(),
       self.file_fetcher.clone(),
+      self.fs.clone(),
       self.global_http_cache.clone(),
-      self.node_resolver.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 { .. }
         ),
-        unstable_detect_cjs: self.options.unstable_detect_cjs(),
       },
     )
   }
@@ -737,12 +729,12 @@ 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,
       },
     )
@@ -1009,7 +1001,11 @@ 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 {
diff --git a/cli/http_util.rs b/cli/http_util.rs
index 9c9ae9e413..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)?;
@@ -792,6 +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 {
@@ -818,6 +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 {
@@ -845,6 +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 {
@@ -866,6 +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);
@@ -885,6 +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 {
@@ -914,6 +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 {
@@ -939,6 +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 {
@@ -974,6 +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 {
@@ -1021,6 +1033,7 @@ mod test {
           maybe_etag: None,
           maybe_auth_token: None,
           maybe_progress_guard: None,
+          maybe_auth: None,
         })
         .await;
 
@@ -1083,6 +1096,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
 
@@ -1136,6 +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 {
@@ -1177,6 +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 {
@@ -1199,6 +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);
@@ -1233,6 +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 {
@@ -1262,6 +1280,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     assert!(result.is_err());
@@ -1283,6 +1302,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
 
@@ -1306,6 +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 8c2e8bb1dc..98215855c9 100644
--- a/cli/lsp/analysis.rs
+++ b/cli/lsp/analysis.rs
@@ -12,13 +12,14 @@ use super::urls::url_to_uri;
 use crate::args::jsr_url;
 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;
@@ -37,9 +38,9 @@ use deno_semver::package::PackageReq;
 use deno_semver::package::PackageReqReference;
 use deno_semver::Version;
 use import_map::ImportMap;
-use node_resolver::NpmResolver;
 use once_cell::sync::Lazy;
 use regex::Regex;
+use std::borrow::Cow;
 use std::cmp::Ordering;
 use std::collections::HashMap;
 use std::collections::HashSet;
@@ -229,6 +230,7 @@ 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,
 }
 
@@ -237,12 +239,14 @@ 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(),
     }
   }
@@ -336,7 +340,12 @@ impl<'a> TsResponseImportMapper<'a> {
       .resolver
       .maybe_managed_npm_resolver(Some(&self.file_referrer))
     {
-      if npm_resolver.in_npm_package(specifier) {
+      let in_npm_pkg = self
+        .resolver
+        .maybe_node_resolver(Some(&self.file_referrer))
+        .map(|n| n.in_npm_package(specifier))
+        .unwrap_or(false);
+      if in_npm_pkg {
         if let Ok(Some(pkg_id)) =
           npm_resolver.resolve_pkg_id_from_specifier(specifier)
         {
@@ -383,6 +392,11 @@ 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
@@ -453,19 +467,36 @@ impl<'a> TsResponseImportMapper<'a> {
     specifier: &str,
     referrer: &ModuleSpecifier,
   ) -> 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_graph_resolver(Some(&self.file_referrer))
+        .resolve(
+          &specifier,
+          &deno_graph::Range {
+            specifier: referrer.clone(),
+            start: deno_graph::Position::zeroed(),
+            end: deno_graph::Position::zeroed(),
+          },
+          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
@@ -555,8 +586,9 @@ fn try_reverse_map_package_json_exports(
 pub fn fix_ts_import_changes(
   referrer: &ModuleSpecifier,
   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();
@@ -598,68 +630,63 @@ 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<Option<tsc::CodeFixAction>, AnyError> {
-  if matches!(
+  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)
+  {
+    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(Some(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) {
-        return Ok(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) {
+    None
+  } else {
+    Some(Cow::Borrowed(action))
   }
-
-  Ok(Some(action.clone()))
 }
 
 /// Determines if two TypeScript diagnostic codes are effectively equivalent.
@@ -730,7 +757,7 @@ pub fn ts_changes_to_edit(
   }))
 }
 
-#[derive(Debug, Deserialize)]
+#[derive(Debug, Deserialize, Serialize)]
 #[serde(rename_all = "camelCase")]
 pub struct CodeActionData {
   pub specifier: ModuleSpecifier,
@@ -1000,11 +1027,7 @@ impl CodeActionCollection {
         "The action returned from TypeScript is unsupported.",
       ));
     }
-    let Some(action) = fix_ts_import_action(
-      specifier,
-      action,
-      &language_server.get_ts_response_import_mapper(specifier),
-    )?
+    let Some(action) = fix_ts_import_action(specifier, action, language_server)
     else {
       return Ok(());
     };
@@ -1027,7 +1050,7 @@ 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)) =
@@ -1054,10 +1077,12 @@ 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 {
@@ -1206,14 +1231,11 @@ impl CodeActionCollection {
         }),
       );
 
-      match parsed_source.program_ref() {
-        deno_ast::swc::ast::Program::Module(module) => module
-          .body
-          .iter()
-          .find(|i| i.range().contains(&specifier_range))
-          .map(|i| text_info.line_and_column_index(i.range().start)),
-        deno_ast::swc::ast::Program::Script(_) => None,
-      }
+      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(
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/config.rs b/cli/lsp/config.rs
index 74f3583d68..34bf64446d 100644
--- a/cli/lsp/config.rs
+++ b/cli/lsp/config.rs
@@ -41,6 +41,7 @@ use deno_runtime::deno_node::PackageJson;
 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;
@@ -439,6 +440,8 @@ 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 {
@@ -449,6 +452,7 @@ 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,
     }
   }
 }
@@ -981,7 +985,7 @@ impl Config {
       | MediaType::Tsx => Some(&workspace_settings.typescript),
       MediaType::Json
       | MediaType::Wasm
-      | MediaType::TsBuildInfo
+      | MediaType::Css
       | MediaType::SourceMap
       | MediaType::Unknown => None,
     }
@@ -1187,6 +1191,7 @@ pub struct ConfigData {
   pub resolver: Arc<WorkspaceResolver>,
   pub sloppy_imports_resolver: Option<Arc<CliSloppyImportsResolver>>,
   pub import_map_from_settings: Option<ModuleSpecifier>,
+  pub unstable: BTreeSet<String>,
   watched_files: HashMap<ModuleSpecifier, ConfigWatchedFileType>,
 }
 
@@ -1584,9 +1589,16 @@ 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(CliSloppyImportsResolver::new(
         SloppyImportsCachedFs::new_without_stat_cache(Arc::new(
@@ -1627,6 +1639,7 @@ impl ConfigData {
       lockfile,
       npmrc,
       import_map_from_settings,
+      unstable,
       watched_files,
     }
   }
@@ -2251,6 +2264,7 @@ 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,
@@ -2296,6 +2310,7 @@ 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 caabd3f04e..83c00d27ed 100644
--- a/cli/lsp/diagnostics.rs
+++ b/cli/lsp/diagnostics.rs
@@ -1499,7 +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(
diff --git a/cli/lsp/documents.rs b/cli/lsp/documents.rs
index 7d1ca6810d..ce13c32157 100644
--- a/cli/lsp/documents.rs
+++ b/cli/lsp/documents.rs
@@ -272,7 +272,7 @@ 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)
@@ -332,12 +332,8 @@ 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(
@@ -399,7 +395,6 @@ impl Document {
       &self.specifier,
       self.maybe_headers.as_ref(),
       self.maybe_language_id,
-      &resolver,
     );
     let dependencies;
     let maybe_types_dependency;
@@ -764,14 +759,7 @@ 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,
@@ -1071,34 +1059,6 @@ 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,
@@ -1561,7 +1521,7 @@ 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,
diff --git a/cli/lsp/language_server.rs b/cli/lsp/language_server.rs
index 908afa1657..2554fa34b1 100644
--- a/cli/lsp/language_server.rs
+++ b/cli/lsp/language_server.rs
@@ -863,7 +863,10 @@ 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
@@ -904,7 +907,7 @@ 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;
@@ -1384,14 +1387,10 @@ 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();
@@ -1838,7 +1837,7 @@ impl Inner {
         fix_ts_import_changes(
           &code_action_data.specifier,
           &combined_code_actions.changes,
-          &self.get_ts_response_import_mapper(&code_action_data.specifier),
+          self,
         )
         .map_err(|err| {
           error!("Unable to remap changes: {:#}", err);
@@ -1891,7 +1890,7 @@ impl Inner {
         refactor_edit_info.edits = fix_ts_import_changes(
           &action_data.specifier,
           &refactor_edit_info.edits,
-          &self.get_ts_response_import_mapper(&action_data.specifier),
+          self,
         )
         .map_err(|err| {
           error!("Unable to remap changes: {:#}", err);
@@ -1922,7 +1921,8 @@ 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,
     )
   }
@@ -2285,7 +2285,11 @@ 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(
@@ -3812,7 +3816,7 @@ 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);
@@ -3948,7 +3952,9 @@ 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/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/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/resolver.rs b/cli/lsp/resolver.rs
index c89273147a..f5df24d575 100644
--- a/cli/lsp/resolver.rs
+++ b/cli/lsp/resolver.rs
@@ -2,6 +2,8 @@
 
 use dashmap::DashMap;
 use deno_ast::MediaType;
+use deno_ast::ParsedSource;
+use deno_cache_dir::npm::NpmCacheDir;
 use deno_cache_dir::HttpCache;
 use deno_config::workspace::PackageJsonDepResolution;
 use deno_config::workspace::WorkspaceResolver;
@@ -14,15 +16,15 @@ use deno_path_util::url_to_file_path;
 use deno_runtime::deno_fs;
 use deno_runtime::deno_node::NodeResolver;
 use deno_runtime::deno_node::PackageJson;
+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::NodeResolutionMode;
-use node_resolver::NpmResolver;
 use std::borrow::Cow;
 use std::collections::BTreeMap;
 use std::collections::BTreeSet;
@@ -36,6 +38,7 @@ use crate::args::create_default_npmrc;
 use crate::args::CacheSetting;
 use crate::args::CliLockfile;
 use crate::args::NpmInstallDepsProvider;
+use crate::cache::DenoCacheEnvFsAdapter;
 use crate::graph_util::CliJsrUrlProvider;
 use crate::http_util::HttpClientProvider;
 use crate::lsp::config::Config;
@@ -43,40 +46,50 @@ 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::CliNpmResolverCreateOptions;
-use crate::npm::CliNpmResolverManagedCreateOptions;
 use crate::npm::CliNpmResolverManagedSnapshotOption;
+use crate::npm::CreateInNpmPkgCheckerOptions;
 use crate::npm::ManagedCliNpmResolver;
-use crate::resolver::CjsResolutionStore;
+use crate::resolver::CjsTracker;
+use crate::resolver::CjsTrackerOptions;
 use crate::resolver::CliDenoResolverFs;
 use crate::resolver::CliGraphResolver;
 use crate::resolver::CliGraphResolverOptions;
 use crate::resolver::CliNodeResolver;
 use crate::resolver::WorkerCliNpmGraphResolver;
+use crate::tsc::into_specifier_and_media_type;
 use crate::util::progress_bar::ProgressBar;
 use crate::util::progress_bar::ProgressBarStyle;
 
 #[derive(Debug, Clone)]
 struct LspScopeResolver {
+  cjs_tracker: Option<Arc<LspCjsTracker>>,
   graph_resolver: Arc<CliGraphResolver>,
   jsr_resolver: Option<Arc<JsrCacheResolver>>,
   npm_resolver: Option<Arc<dyn CliNpmResolver>>,
   node_resolver: Option<Arc<CliNodeResolver>>,
+  pkg_json_resolver: Option<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 {
     Self {
+      cjs_tracker: None,
       graph_resolver: create_graph_resolver(None, None, None),
       jsr_resolver: None,
       npm_resolver: None,
       node_resolver: None,
+      pkg_json_resolver: None,
       redirect_resolver: None,
       graph_imports: Default::default(),
+      package_json_deps_by_resolution: Default::default(),
       config_data: None,
     }
   }
@@ -90,14 +103,35 @@ impl LspScopeResolver {
   ) -> Self {
     let mut npm_resolver = None;
     let mut node_resolver = None;
+    let mut lsp_cjs_tracker = None;
+    let fs = Arc::new(deno_fs::RealFs);
+    let pkg_json_resolver = Arc::new(PackageJsonResolver::new(
+      deno_runtime::deno_node::DenoFsNodeResolverEnv::new(fs.clone()),
+    ));
     if let Some(http_client) = http_client_provider {
       npm_resolver = create_npm_resolver(
         config_data.map(|d| d.as_ref()),
         cache,
         http_client,
+        &pkg_json_resolver,
       )
       .await;
-      node_resolver = create_node_resolver(npm_resolver.as_ref());
+      if let Some(npm_resolver) = &npm_resolver {
+        let in_npm_pkg_checker = create_in_npm_pkg_checker(npm_resolver);
+        let cjs_tracker = create_cjs_tracker(
+          in_npm_pkg_checker.clone(),
+          pkg_json_resolver.clone(),
+        );
+        lsp_cjs_tracker =
+          Some(Arc::new(LspCjsTracker::new(cjs_tracker.clone())));
+        node_resolver = Some(create_node_resolver(
+          cjs_tracker,
+          fs.clone(),
+          in_npm_pkg_checker,
+          npm_resolver,
+          pkg_json_resolver.clone(),
+        ));
+      }
     }
     let graph_resolver = create_graph_resolver(
       config_data.map(|d| d.as_ref()),
@@ -133,13 +167,43 @@ impl LspScopeResolver {
         )
       })
       .unwrap_or_default();
+    let package_json_deps_by_resolution = (|| {
+      let node_resolver = node_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(
+            node_resolver
+              .resolve_req_reference(
+                &req_ref,
+                &referrer,
+                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 {
+      cjs_tracker: lsp_cjs_tracker,
       graph_resolver,
       jsr_resolver,
       npm_resolver,
       node_resolver,
+      pkg_json_resolver: Some(pkg_json_resolver),
       redirect_resolver,
       graph_imports,
+      package_json_deps_by_resolution,
       config_data: config_data.cloned(),
     }
   }
@@ -147,19 +211,44 @@ impl LspScopeResolver {
   fn snapshot(&self) -> Arc<Self> {
     let npm_resolver =
       self.npm_resolver.as_ref().map(|r| r.clone_snapshotted());
-    let node_resolver = create_node_resolver(npm_resolver.as_ref());
+    let fs = Arc::new(deno_fs::RealFs);
+    let pkg_json_resolver = Arc::new(PackageJsonResolver::new(
+      deno_runtime::deno_node::DenoFsNodeResolverEnv::new(fs.clone()),
+    ));
+    let mut node_resolver = None;
+    let mut lsp_cjs_tracker = None;
+    if let Some(npm_resolver) = &npm_resolver {
+      let in_npm_pkg_checker = create_in_npm_pkg_checker(npm_resolver);
+      let cjs_tracker = create_cjs_tracker(
+        in_npm_pkg_checker.clone(),
+        pkg_json_resolver.clone(),
+      );
+      lsp_cjs_tracker = Some(Arc::new(LspCjsTracker::new(cjs_tracker.clone())));
+      node_resolver = Some(create_node_resolver(
+        cjs_tracker,
+        fs,
+        in_npm_pkg_checker,
+        npm_resolver,
+        pkg_json_resolver.clone(),
+      ));
+    }
     let graph_resolver = create_graph_resolver(
       self.config_data.as_deref(),
       npm_resolver.as_ref(),
       node_resolver.as_ref(),
     );
     Arc::new(Self {
+      cjs_tracker: lsp_cjs_tracker,
       graph_resolver,
       jsr_resolver: self.jsr_resolver.clone(),
       npm_resolver,
       node_resolver,
       redirect_resolver: self.redirect_resolver.clone(),
+      pkg_json_resolver: Some(pkg_json_resolver),
       graph_imports: self.graph_imports.clone(),
+      package_json_deps_by_resolution: self
+        .package_json_deps_by_resolution
+        .clone(),
       config_data: self.config_data.clone(),
     })
   }
@@ -261,6 +350,22 @@ impl LspResolver {
     resolver.graph_resolver.create_graph_npm_resolver()
   }
 
+  pub fn maybe_cjs_tracker(
+    &self,
+    file_referrer: Option<&ModuleSpecifier>,
+  ) -> Option<&Arc<LspCjsTracker>> {
+    let resolver = self.get_scope_resolver(file_referrer);
+    resolver.cjs_tracker.as_ref()
+  }
+
+  pub fn maybe_node_resolver(
+    &self,
+    file_referrer: Option<&ModuleSpecifier>,
+  ) -> Option<&Arc<CliNodeResolver>> {
+    let resolver = self.get_scope_resolver(file_referrer);
+    resolver.node_resolver.as_ref()
+  }
+
   pub fn maybe_managed_npm_resolver(
     &self,
     file_referrer: Option<&ModuleSpecifier>,
@@ -328,13 +433,25 @@ impl LspResolver {
   ) -> 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(Some(
+    Some(into_specifier_and_media_type(Some(
       node_resolver
         .resolve_req_reference(req_ref, referrer, 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 {
     fn has_node_modules_dir(specifier: &ModuleSpecifier) -> bool {
       // consider any /node_modules/ directory as being in the node_modules
@@ -346,14 +463,10 @@ 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;
       }
     }
@@ -361,18 +474,6 @@ impl LspResolver {
     has_node_modules_dir(specifier)
   }
 
-  pub fn node_media_type(
-    &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)
-  }
-
   pub fn is_bare_package_json_dep(
     &self,
     specifier_text: &str,
@@ -398,10 +499,10 @@ 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 {
+    let Some(pkg_json_resolver) = resolver.pkg_json_resolver.as_ref() else {
       return Ok(None);
     };
-    node_resolver.get_closest_package_json(referrer)
+    pkg_json_resolver.get_closest_package_json(referrer)
   }
 
   pub fn resolve_redirects(
@@ -457,11 +558,13 @@ async fn create_npm_resolver(
   config_data: Option<&ConfigData>,
   cache: &LspCache,
   http_client_provider: &Arc<HttpClientProvider>,
+  pkg_json_resolver: &Arc<PackageJsonResolver>,
 ) -> Option<Arc<dyn CliNpmResolver>> {
   let enable_byonm = 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: pkg_json_resolver.clone(),
       root_node_modules_dir: config_data.and_then(|config_data| {
         config_data.node_modules_dir.clone().or_else(|| {
           url_to_file_path(&config_data.scope)
@@ -471,7 +574,15 @@ async fn create_npm_resolver(
       }),
     })
   } else {
-    CliNpmResolverCreateOptions::Managed(CliNpmResolverManagedCreateOptions {
+    let npmrc = config_data
+      .and_then(|d| d.npmrc.clone())
+      .unwrap_or_else(create_default_npmrc);
+    let npm_cache_dir = Arc::new(NpmCacheDir::new(
+      &DenoCacheEnvFsAdapter(&deno_fs::RealFs),
+      cache.deno_dir().npm_folder_path(),
+      npmrc.get_all_known_registries_urls(),
+    ));
+    CliNpmResolverCreateOptions::Managed(CliManagedNpmResolverCreateOptions {
       http_client_provider: http_client_provider.clone(),
       snapshot: match config_data.and_then(|d| d.lockfile.as_ref()) {
         Some(lockfile) => {
@@ -485,7 +596,7 @@ async fn create_npm_resolver(
       // 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(),
+      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
@@ -496,9 +607,7 @@ async fn create_npm_resolver(
         .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
-        .and_then(|d| d.npmrc.clone())
-        .unwrap_or_else(create_default_npmrc),
+      npmrc,
       npm_system_info: NpmSystemInfo::default(),
       lifecycle_scripts: Default::default(),
     })
@@ -506,28 +615,59 @@ async fn create_npm_resolver(
   Some(create_cli_npm_resolver_for_lsp(options).await)
 }
 
+fn create_cjs_tracker(
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+  pkg_json_resolver: Arc<PackageJsonResolver>,
+) -> Arc<CjsTracker> {
+  Arc::new(CjsTracker::new(
+    in_npm_pkg_checker,
+    pkg_json_resolver,
+    CjsTrackerOptions {
+      // todo(dsherret): support in the lsp by stabilizing the feature
+      // so that we don't have to pipe the config in here
+      unstable_detect_cjs: false,
+    },
+  ))
+}
+
+fn create_in_npm_pkg_checker(
+  npm_resolver: &Arc<dyn CliNpmResolver>,
+) -> Arc<dyn InNpmPackageChecker> {
+  crate::npm::create_in_npm_pkg_checker(match npm_resolver.as_inner() {
+    crate::npm::InnerCliNpmResolverRef::Byonm(_) => {
+      CreateInNpmPkgCheckerOptions::Byonm
+    }
+    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(),
+        },
+      )
+    }
+  })
+}
+
 fn create_node_resolver(
-  npm_resolver: Option<&Arc<dyn CliNpmResolver>>,
-) -> Option<Arc<CliNodeResolver>> {
-  use once_cell::sync::Lazy;
-
-  // 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);
-
-  let npm_resolver = npm_resolver?;
-  let fs = Arc::new(deno_fs::RealFs);
+  cjs_tracker: Arc<CjsTracker>,
+  fs: Arc<dyn deno_fs::FileSystem>,
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+  npm_resolver: &Arc<dyn CliNpmResolver>,
+  pkg_json_resolver: Arc<PackageJsonResolver>,
+) -> Arc<CliNodeResolver> {
   let node_resolver_inner = Arc::new(NodeResolver::new(
     deno_runtime::deno_node::DenoFsNodeResolverEnv::new(fs.clone()),
+    in_npm_pkg_checker.clone(),
     npm_resolver.clone().into_npm_resolver(),
+    pkg_json_resolver.clone(),
   ));
-  Some(Arc::new(CliNodeResolver::new(
-    CJS_RESOLUTIONS.clone(),
+  Arc::new(CliNodeResolver::new(
+    cjs_tracker.clone(),
     fs,
+    in_npm_pkg_checker,
     node_resolver_inner,
     npm_resolver.clone(),
-  )))
+  ))
 }
 
 fn create_graph_resolver(
@@ -555,8 +695,8 @@ fn create_graph_resolver(
       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")),
+    bare_node_builtins_enabled: config_data
+      .is_some_and(|d| d.unstable.contains("bare-node-builtins")),
     sloppy_imports_resolver: config_data
       .and_then(|d| d.sloppy_imports_resolver.clone()),
   }))
@@ -702,6 +842,45 @@ impl RedirectResolver {
   }
 }
 
+#[derive(Debug)]
+pub struct LspCjsTracker {
+  cjs_tracker: Arc<CjsTracker>,
+}
+
+impl LspCjsTracker {
+  pub fn new(cjs_tracker: Arc<CjsTracker>) -> Self {
+    Self { cjs_tracker }
+  }
+
+  pub fn is_cjs(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+    maybe_parsed_source: Option<&ParsedSource>,
+  ) -> bool {
+    if let Some(module_kind) =
+      self.cjs_tracker.get_known_kind(specifier, media_type)
+    {
+      module_kind.is_cjs()
+    } else {
+      let maybe_is_script = maybe_parsed_source.map(|p| p.compute_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)
+        })
+    }
+  }
+}
+
 #[cfg(test)]
 mod tests {
   use super::*;
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 cfab39b20b..6f63ced5be 100644
--- a/cli/lsp/tsc.rs
+++ b/cli/lsp/tsc.rs
@@ -236,7 +236,7 @@ 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 +882,22 @@ 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 +2184,50 @@ 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 +2249,7 @@ 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 +2257,23 @@ 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,
@@ -3584,6 +3644,12 @@ 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 +3711,17 @@ 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 +3754,28 @@ 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 +3924,24 @@ 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
@@ -4154,6 +4244,13 @@ 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 +4368,7 @@ 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,
   };
@@ -4304,14 +4401,25 @@ fn op_load<'s>(
       None
     } else {
       let asset_or_document = state.get_asset_or_document(&specifier);
-      asset_or_document.map(|doc| LoadResponse {
-        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
-        ),
+      asset_or_document.map(|doc| {
+        let maybe_cjs_tracker = state
+          .state_snapshot
+          .resolver
+          .maybe_cjs_tracker(Some(&specifier));
+        LoadResponse {
+          data: doc.text(),
+          script_kind: crate::tsc::as_ts_script_kind(doc.media_type()),
+          version: state.script_version(&specifier),
+          is_cjs: maybe_cjs_tracker
+            .map(|t| {
+              t.is_cjs(
+                &specifier,
+                doc.media_type(),
+                doc.maybe_parsed_source().and_then(|p| p.as_ref().ok()),
+              )
+            })
+            .unwrap_or(false),
+        }
       })
     };
 
@@ -4540,7 +4648,10 @@ 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))
@@ -4892,6 +5003,10 @@ 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 +5024,7 @@ 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 +5129,9 @@ 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
     }
   }
@@ -5958,6 +6077,7 @@ mod tests {
         Some(temp_dir.url()),
       )
       .await
+      .unwrap()
       .unwrap();
     assert_eq!(info.entries.len(), 22);
     let details = ts_server
@@ -6117,6 +6237,7 @@ mod tests {
         Some(temp_dir.url()),
       )
       .await
+      .unwrap()
       .unwrap();
     let entry = info
       .entries
@@ -6154,7 +6275,7 @@ 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 d99a4c402a..04daff6700 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;
@@ -136,7 +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(
@@ -169,10 +168,10 @@ async fn run_subcommand(flags: Arc<Flags>) -> Result<i32, AnyError> {
       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"));
       }
diff --git a/cli/mainrt.rs b/cli/mainrt.rs
index 02d58fcee1..f5b798f817 100644
--- a/cli/mainrt.rs
+++ b/cli/mainrt.rs
@@ -88,11 +88,10 @@ 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?;
+      Ok(Some(data)) => {
+        util::logger::init(data.metadata.log_level);
+        load_env_vars(&data.metadata.env_vars_from_env_file);
+        let exit_code = standalone::run(data).await?;
         std::process::exit(exit_code);
       }
       Ok(None) => Ok(()),
diff --git a/cli/module_loader.rs b/cli/module_loader.rs
index 37d42f78e5..43c9e1aa07 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;
@@ -23,19 +24,23 @@ use crate::graph_container::ModuleGraphUpdatePermit;
 use crate::graph_util::CreateGraphOptions;
 use crate::graph_util::ModuleGraphBuilder;
 use crate::node;
+use crate::node::CliNodeCodeTranslator;
 use crate::npm::CliNpmResolver;
+use crate::resolver::CjsTracker;
 use crate::resolver::CliGraphResolver;
 use crate::resolver::CliNodeResolver;
 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;
@@ -63,9 +68,12 @@ 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_permissions::PermissionsContainer;
 use deno_semver::npm::NpmPackageReqReference;
+use node_resolver::InNpmPackageChecker;
 use node_resolver::NodeResolutionMode;
 
 pub struct ModuleLoadPreparer {
@@ -198,11 +206,16 @@ struct SharedCliModuleLoaderState {
   lib_worker: TsTypeLib,
   initial_cwd: PathBuf,
   is_inspecting: bool,
+  is_npm_main: 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_code_translator: Arc<CliNodeCodeTranslator>,
   node_resolver: Arc<CliNodeResolver>,
   npm_resolver: Arc<dyn CliNpmResolver>,
   npm_module_loader: NpmModuleLoader,
@@ -218,10 +231,14 @@ 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_code_translator: Arc<CliNodeCodeTranslator>,
     node_resolver: Arc<CliNodeResolver>,
     npm_resolver: Arc<dyn CliNpmResolver>,
     npm_module_loader: NpmModuleLoader,
@@ -235,14 +252,19 @@ impl CliModuleLoaderFactory {
         lib_worker: options.ts_type_lib_worker(),
         initial_cwd: options.initial_cwd().to_path_buf(),
         is_inspecting: options.is_inspecting(),
+        is_npm_main: options.is_npm_main(),
         is_repl: matches!(
           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_resolver,
         npm_module_loader,
@@ -259,19 +281,30 @@ 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,
+  ) -> CreateModuleLoaderResult {
+    let module_loader =
+      Rc::new(CliModuleLoader(Rc::new(CliModuleLoaderInner {
+        lib,
+        is_worker,
+        is_npm_main: self.shared.is_npm_main,
+        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::new(
+      self.shared.emitter.clone(),
+      self.shared.fs.clone(),
       graph_container,
-      emitter: self.shared.emitter.clone(),
-      parsed_source_cache: self.shared.parsed_source_cache.clone(),
-      shared: self.shared.clone(),
-    })));
-    ModuleLoaderAndSourceMapGetter {
-      module_loader: loader,
+      self.shared.in_npm_pkg_checker.clone(),
+      self.shared.npm_resolver.clone(),
+    ));
+    CreateModuleLoaderResult {
+      module_loader,
+      node_require_loader,
     }
   }
 }
@@ -280,7 +313,7 @@ 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,
@@ -294,7 +327,7 @@ 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(
@@ -310,6 +343,7 @@ impl ModuleLoaderFactory for CliModuleLoaderFactory {
 
 struct CliModuleLoaderInner<TGraphContainer: ModuleGraphContainer> {
   lib: TsTypeLib,
+  is_npm_main: bool,
   is_worker: bool,
   /// The initial set of permissions used to resolve the static imports in the
   /// worker. These are "allow all" for main worker, and parent thread
@@ -318,6 +352,7 @@ 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,
 }
@@ -331,24 +366,7 @@ impl<TGraphContainer: ModuleGraphContainer>
     maybe_referrer: Option<&ModuleSpecifier>,
     requested_module_type: RequestedModuleType,
   ) -> Result<ModuleSource, AnyError> {
-    let code_source = match self.load_prepared_module(specifier).await? {
-      Some(code_source) => code_source,
-      None => {
-        if self.shared.npm_module_loader.if_in_npm_package(specifier) {
-          self
-            .shared
-            .npm_module_loader
-            .load(specifier, maybe_referrer)
-            .await?
-        } else {
-          let mut msg = format!("Loading unprepared module: {specifier}");
-          if let Some(referrer) = maybe_referrer {
-            msg = format!("{}, imported from: {}", msg, referrer.as_str());
-          }
-          return Err(anyhow!(msg));
-        }
-      }
-    };
+    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
@@ -402,6 +420,29 @@ 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.node_resolver.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,
@@ -474,15 +515,11 @@ impl<TGraphContainer: ModuleGraphContainer>
     if self.shared.is_repl {
       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 self.shared.node_resolver.resolve_req_reference(
+          &reference,
+          referrer,
+          NodeResolutionMode::Execution,
+        );
       }
     }
 
@@ -506,13 +543,15 @@ impl<TGraphContainer: ModuleGraphContainer>
           .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(),
     };
@@ -534,23 +573,32 @@ impl<TGraphContainer: ModuleGraphContainer>
       }) => {
         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(Some(ModuleCodeStringSource {
-          code: ModuleSourceCode::Bytes(transpile_result),
+          // 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,
         }))
       }
+      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,
   ) -> Result<Option<ModuleCodeStringSource>, AnyError> {
@@ -563,19 +611,31 @@ impl<TGraphContainer: ModuleGraphContainer>
         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(Some(ModuleCodeStringSource {
-          code: ModuleSourceCode::Bytes(transpile_result),
+          // 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,
         }))
       }
+      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),
     }
   }
@@ -605,20 +665,40 @@ impl<TGraphContainer: ModuleGraphContainer>
         source,
         media_type,
         specifier,
+        is_script,
         ..
       })) => {
+        // todo(dsherret): revert in https://github.com/denoland/deno/pull/26439
+        if self.is_npm_main && *is_script
+          || 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::Cjs | MediaType::Cts => {
+            return Ok(Some(CodeOrDeferredEmit::Cjs {
+              specifier,
+              media_type: *media_type,
+              source,
+            }));
+          }
           MediaType::TypeScript
           | MediaType::Mts
-          | MediaType::Cts
           | MediaType::Jsx
           | MediaType::Tsx => {
             return Ok(Some(CodeOrDeferredEmit::DeferredEmit {
@@ -627,7 +707,7 @@ impl<TGraphContainer: ModuleGraphContainer>
               source,
             }));
           }
-          MediaType::TsBuildInfo | MediaType::Wasm | MediaType::SourceMap => {
+          MediaType::Css | MediaType::Wasm | MediaType::SourceMap => {
             panic!("Unexpected media type {media_type} for {specifier}")
           }
         };
@@ -649,6 +729,48 @@ impl<TGraphContainer: ModuleGraphContainer>
       | 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> {
@@ -658,6 +780,11 @@ 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
@@ -819,7 +946,10 @@ impl<TGraphContainer: ModuleGraphContainer> ModuleLoader
       "wasm" | "file" | "http" | "https" | "data" | "blob" => (),
       _ => return None,
     }
-    let source = self.0.load_prepared_module_sync(&specifier).ok()??;
+    let source = self
+      .0
+      .load_prepared_module_for_source_map_sync(&specifier)
+      .ok()??;
     source_map_from_code(source.code.as_bytes())
   }
 
@@ -898,3 +1028,79 @@ impl ModuleGraphUpdatePermit for WorkerModuleGraphUpdatePermit {
     drop(self.permit); // explicit drop for clarity
   }
 }
+
+#[derive(Debug)]
+struct CliNodeRequireLoader<TGraphContainer: ModuleGraphContainer> {
+  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>
+  CliNodeRequireLoader<TGraphContainer>
+{
+  pub fn new(
+    emitter: Arc<Emitter>,
+    fs: Arc<dyn FileSystem>,
+    graph_container: TGraphContainer,
+    in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+    npm_resolver: Arc<dyn CliNpmResolver>,
+  ) -> Self {
+    Self {
+      emitter,
+      fs,
+      graph_container,
+      in_npm_pkg_checker,
+      npm_resolver,
+    }
+  }
+}
+
+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)
+    }
+  }
+}
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 811efb1ecc..0000000000
--- a/cli/napi/mod.rs
+++ /dev/null
@@ -1,21 +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;
-pub mod uv;
diff --git a/cli/node.rs b/cli/node.rs
index 733d5f8717..1d410a726a 100644
--- a/cli/node.rs
+++ b/cli/node.rs
@@ -1,11 +1,14 @@
 // 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_path_util::url_from_file_path;
+use deno_path_util::url_to_file_path;
 use deno_runtime::deno_fs;
 use deno_runtime::deno_node::DenoFsNodeResolverEnv;
 use node_resolver::analyze::CjsAnalysis as ExtNodeCjsAnalysis;
@@ -18,8 +21,8 @@ use serde::Serialize;
 use crate::cache::CacheDBHash;
 use crate::cache::NodeAnalysisCache;
 use crate::cache::ParsedSourceCache;
-use crate::resolver::CliNodeResolver;
-use crate::util::fs::canonicalize_path_maybe_not_exists;
+use crate::resolver::CjsTracker;
+use crate::util::fs::canonicalize_path_maybe_not_exists_with_fs;
 
 pub type CliNodeCodeTranslator =
   NodeCodeTranslator<CliCjsCodeAnalyzer, DenoFsNodeResolverEnv>;
@@ -32,14 +35,14 @@ 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()
+  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| canonicalize_path_maybe_not_exists(&path).ok())
-    .and_then(|path| ModuleSpecifier::from_file_path(path).ok())
+    .and_then(|path| canonicalize_path_maybe_not_exists_with_fs(&path, fs).ok())
+    .and_then(|path| url_from_file_path(&path).ok())
     .unwrap_or_else(|| specifier.clone())
 }
 
@@ -56,23 +59,29 @@ 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>>,
+  // todo(dsherret): hack, remove in https://github.com/denoland/deno/pull/26439
+  // For example, this does not properly handle if cjs analysis was already done
+  // and has been cached.
+  is_npm_main: bool,
 }
 
 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>>,
+    is_npm_main: bool,
   ) -> Self {
     Self {
       cache,
+      cjs_tracker,
       fs,
-      node_resolver,
       parsed_source_cache,
+      is_npm_main,
     }
   }
 
@@ -88,7 +97,7 @@ 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![],
@@ -96,62 +105,53 @@ 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_npm_main = self.is_npm_main;
+    let is_maybe_cjs =
+      cjs_tracker.is_maybe_cjs(specifier, media_type)? || is_npm_main;
+    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 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 =
-          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,
+      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,
+          )? || is_script && is_npm_main;
+          if is_cjs {
+            let analysis = parsed_source.analyze_cjs();
+            Ok(CliCjsAnalysis::Cjs {
+              exports: analysis.exports,
+              reexports: analysis.reexports,
             })
-          })?;
-        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)
+          } else {
+            Ok(CliCjsAnalysis::Esm)
+          }
         }
-      }
-    })
-    .await
-    .unwrap()?;
+      })
+      .await
+      .unwrap()?
+    } else {
+      CliCjsAnalysis::Esm
+    };
 
     self
       .cache
@@ -163,11 +163,11 @@ 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 => {
@@ -175,7 +175,7 @@ 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 fc095ab16f..45fa4cfd1f 100644
--- a/cli/npm/byonm.rs
+++ b/cli/npm/byonm.rs
@@ -10,8 +10,8 @@ use deno_core::serde_json;
 use deno_core::url::Url;
 use deno_resolver::npm::ByonmNpmResolver;
 use deno_resolver::npm::ByonmNpmResolverCreateOptions;
+use deno_runtime::deno_node::DenoFsNodeResolverEnv;
 use deno_runtime::deno_node::NodePermissions;
-use deno_runtime::deno_node::NodeRequireResolver;
 use deno_runtime::ops::process::NpmProcessStateProvider;
 use deno_semver::package::PackageReq;
 use node_resolver::NpmResolver;
@@ -25,30 +25,14 @@ use super::InnerCliNpmResolverRef;
 use super::ResolvePkgFolderFromDenoReqError;
 
 pub type CliByonmNpmResolverCreateOptions =
-  ByonmNpmResolverCreateOptions<CliDenoResolverFs>;
-pub type CliByonmNpmResolver = ByonmNpmResolver<CliDenoResolverFs>;
+  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)]
 struct CliByonmWrapper(Arc<CliByonmNpmResolver>);
 
-impl NodeRequireResolver for CliByonmWrapper {
-  fn ensure_read_permission<'a>(
-    &self,
-    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)
-    } else {
-      Ok(Cow::Borrowed(path))
-    }
-  }
-}
-
 impl NpmProcessStateProvider for CliByonmWrapper {
   fn get_npm_process_state(&self) -> String {
     serde_json::to_string(&NpmProcessState {
@@ -67,10 +51,6 @@ impl CliNpmResolver for CliByonmNpmResolver {
     self
   }
 
-  fn into_require_resolver(self: Arc<Self>) -> Arc<dyn NodeRequireResolver> {
-    Arc::new(CliByonmWrapper(self))
-  }
-
   fn into_process_state_provider(
     self: Arc<Self>,
   ) -> Arc<dyn NpmProcessStateProvider> {
@@ -100,6 +80,21 @@ impl CliNpmResolver for CliByonmNpmResolver {
     .map_err(ResolvePkgFolderFromDenoReqError::Byonm)
   }
 
+  fn ensure_read_permission<'a>(
+    &self,
+    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))
+    }
+  }
+
   fn check_state_hash(&self) -> Option<u64> {
     // it is very difficult to determine the check state hash for byonm
     // so we just return None to signify check caching is not supported
diff --git a/cli/npm/common.rs b/cli/npm/common.rs
index de282310a1..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 fa0e8c8a59..8ae99f41e0 100644
--- a/cli/npm/managed/cache/mod.rs
+++ b/cli/npm/managed/cache/mod.rs
@@ -26,7 +26,7 @@ use crate::cache::CACHE_PERM;
 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;
 
@@ -36,7 +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
@@ -45,7 +45,7 @@ pub struct NpmCache {
 
 impl NpmCache {
   pub fn new(
-    cache_dir: NpmCacheDir,
+    cache_dir: Arc<NpmCacheDir>,
     cache_setting: CacheSetting,
     npmrc: Arc<ResolvedNpmRc>,
   ) -> Self {
@@ -61,6 +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()
   }
@@ -152,10 +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,
diff --git a/cli/npm/managed/cache/registry_info.rs b/cli/npm/managed/cache/registry_info.rs
index 6c4a7503b5..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) {
@@ -239,36 +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);
-    // 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()
-  }
+}
+
+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/mod.rs b/cli/npm/managed/mod.rs
index ec50a9c65a..4a91bc3474 100644
--- a/cli/npm/managed/mod.rs
+++ b/cli/npm/managed/mod.rs
@@ -12,6 +12,7 @@ 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;
@@ -24,12 +25,12 @@ use deno_npm::NpmSystemInfo;
 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::InNpmPackageChecker;
 use node_resolver::NpmResolver;
 use resolution::AddPkgReqsResult;
 
@@ -38,7 +39,7 @@ use crate::args::LifecycleScriptsConfig;
 use crate::args::NpmInstallDepsProvider;
 use crate::args::NpmProcessState;
 use crate::args::NpmProcessStateKind;
-use crate::cache::DenoCacheEnvFsAdapter;
+use crate::args::PackageJsonDepValueParseWithLocationError;
 use crate::cache::FastInsecureHasher;
 use crate::http_util::HttpClientProvider;
 use crate::util::fs::canonicalize_path_maybe_not_exists_with_fs;
@@ -55,7 +56,7 @@ use super::CliNpmResolver;
 use super::InnerCliNpmResolverRef;
 use super::ResolvePkgFolderFromDenoReqError;
 
-mod cache;
+pub mod cache;
 mod registry;
 mod resolution;
 mod resolvers;
@@ -65,12 +66,12 @@ 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>,
@@ -81,7 +82,7 @@ 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());
@@ -114,7 +115,7 @@ 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());
@@ -188,20 +189,16 @@ fn create_inner(
   ))
 }
 
-fn create_cache(options: &CliNpmResolverManagedCreateOptions) -> Arc<NpmCache> {
+fn create_cache(options: &CliManagedNpmResolverCreateOptions) -> Arc<NpmCache> {
   Arc::new(NpmCache::new(
-    NpmCacheDir::new(
-      &DenoCacheEnvFsAdapter(options.fs.as_ref()),
-      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(
@@ -258,6 +255,35 @@ 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 {
@@ -480,19 +506,24 @@ impl ManagedCliNpmResolver {
     self.resolution.resolve_pkg_id_from_pkg_req(req)
   }
 
-  pub fn ensure_no_pkg_json_dep_errors(&self) -> Result<(), AnyError> {
+  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 {
+      match &err.source {
         deno_package_json::PackageJsonDepValueParseError::VersionReq(_) => {
-          return Err(
-            AnyError::from(err.clone())
-              .context("Failed to install from package.json"),
-          );
+          return Err(Box::new(err.clone()));
         }
         deno_package_json::PackageJsonDepValueParseError::Unsupported {
           ..
         } => {
-          log::warn!("{} {} in package.json", colors::yellow("Warning"), err)
+          // only warn for this one
+          log::warn!(
+            "{} {}\n    at {}",
+            colors::yellow("Warning"),
+            err.source,
+            err.location,
+          )
         }
       }
     }
@@ -549,8 +580,16 @@ 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()
   }
 }
 
@@ -585,22 +624,6 @@ 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<'a>(
-    &self,
-    permissions: &mut dyn NodePermissions,
-    path: &'a Path,
-  ) -> Result<Cow<'a, Path>, AnyError> {
-    self.fs_resolver.ensure_read_permission(permissions, path)
-  }
 }
 
 impl NpmProcessStateProvider for ManagedCliNpmResolver {
@@ -617,10 +640,6 @@ impl CliNpmResolver for ManagedCliNpmResolver {
     self
   }
 
-  fn into_require_resolver(self: Arc<Self>) -> Arc<dyn NodeRequireResolver> {
-    self
-  }
-
   fn into_process_state_provider(
     self: Arc<Self>,
   ) -> Arc<dyn NpmProcessStateProvider> {
@@ -681,6 +700,14 @@ impl CliNpmResolver for ManagedCliNpmResolver {
       .map_err(ResolvePkgFolderFromDenoReqError::Managed)
   }
 
+  fn ensure_read_permission<'a>(
+    &self,
+    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> {
     // We could go further and check all the individual
     // npm packages, but that's probably overkill.
diff --git a/cli/npm/managed/resolvers/common.rs b/cli/npm/managed/resolvers/common.rs
index 867bb4168a..eee11c7604 100644
--- a/cli/npm/managed/resolvers/common.rs
+++ b/cli/npm/managed/resolvers/common.rs
@@ -17,7 +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;
@@ -30,9 +29,6 @@ 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<&Path>;
 
@@ -137,7 +133,7 @@ impl RegistryReadPermissionChecker {
       }
     }
 
-    permissions.check_read_path(path)
+    permissions.check_read_path(path).map_err(Into::into)
   }
 }
 
diff --git a/cli/npm/managed/resolvers/global.rs b/cli/npm/managed/resolvers/global.rs
index 5be315e992..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,
@@ -69,10 +68,6 @@ 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<&Path> {
     None
   }
diff --git a/cli/npm/managed/resolvers/local.rs b/cli/npm/managed/resolvers/local.rs
index 54f7576ade..eddb0dc9b6 100644
--- a/cli/npm/managed/resolvers/local.rs
+++ b/cli/npm/managed/resolvers/local.rs
@@ -155,10 +155,6 @@ 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<&Path> {
     Some(self.root_node_modules_path.as_ref())
   }
@@ -1039,12 +1035,18 @@ 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/mod.rs b/cli/npm/mod.rs
index 53baaf77b4..0d434ca27f 100644
--- a/cli/npm/mod.rs
+++ b/cli/npm/mod.rs
@@ -4,30 +4,37 @@ mod byonm;
 mod common;
 mod managed;
 
+use std::borrow::Cow;
 use std::path::Path;
 use std::path::PathBuf;
 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_resolver::npm::ByonmInNpmPackageChecker;
 use deno_resolver::npm::ByonmNpmResolver;
 use deno_resolver::npm::ByonmResolvePkgFolderFromDenoReqError;
-use deno_runtime::deno_node::NodeRequireResolver;
+use deno_runtime::deno_node::NodePermissions;
 use deno_runtime::ops::process::NpmProcessStateProvider;
 use deno_semver::package::PackageNv;
 use deno_semver::package::PackageReq;
+use managed::cache::registry_info::get_package_url;
+use managed::create_managed_in_npm_pkg_checker;
+use node_resolver::InNpmPackageChecker;
 use node_resolver::NpmResolver;
 use thiserror::Error;
 
-use crate::args::npm_registry_url;
 use crate::file_fetcher::FileFetcher;
 
 pub use self::byonm::CliByonmNpmResolver;
 pub use self::byonm::CliByonmNpmResolverCreateOptions;
-pub use self::managed::CliNpmResolverManagedCreateOptions;
+pub use self::managed::CliManagedInNpmPkgCheckerCreateOptions;
+pub use self::managed::CliManagedNpmResolverCreateOptions;
 pub use self::managed::CliNpmResolverManagedSnapshotOption;
 pub use self::managed::ManagedCliNpmResolver;
 
@@ -40,7 +47,7 @@ pub enum ResolvePkgFolderFromDenoReqError {
 }
 
 pub enum CliNpmResolverCreateOptions {
-  Managed(CliNpmResolverManagedCreateOptions),
+  Managed(CliManagedNpmResolverCreateOptions),
   Byonm(CliByonmNpmResolverCreateOptions),
 }
 
@@ -66,6 +73,22 @@ pub async fn create_cli_npm_resolver(
   }
 }
 
+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)]
@@ -74,7 +97,6 @@ pub enum InnerCliNpmResolverRef<'a> {
 
 pub trait CliNpmResolver: NpmResolver {
   fn into_npm_resolver(self: Arc<Self>) -> Arc<dyn NpmResolver>;
-  fn into_require_resolver(self: Arc<Self>) -> Arc<dyn NodeRequireResolver>;
   fn into_process_state_provider(
     self: Arc<Self>,
   ) -> Arc<dyn NpmProcessStateProvider>;
@@ -105,6 +127,12 @@ pub trait CliNpmResolver: NpmResolver {
     referrer: &ModuleSpecifier,
   ) -> Result<PathBuf, ResolvePkgFolderFromDenoReqError>;
 
+  fn ensure_read_permission<'a>(
+    &self,
+    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.
   fn check_state_hash(&self) -> Option<u64>;
@@ -115,14 +143,19 @@ 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,
     }
   }
 
@@ -157,11 +190,21 @@ 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()??;
@@ -172,3 +215,15 @@ 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 5d1e6e746d..1f4a4bd9b5 100644
--- a/cli/ops/bench.rs
+++ b/cli/ops/bench.rs
@@ -2,7 +2,6 @@
 
 use std::sync::atomic::AtomicUsize;
 use std::sync::atomic::Ordering;
-use std::time;
 
 use deno_core::error::generic_error;
 use deno_core::error::type_error;
@@ -13,6 +12,7 @@ use deno_core::ModuleSpecifier;
 use deno_core::OpState;
 use deno_runtime::deno_permissions::ChildPermissionsArg;
 use deno_runtime::deno_permissions::PermissionsContainer;
+use deno_runtime::deno_web::StartTime;
 use tokio::sync::mpsc::UnboundedSender;
 use uuid::Uuid;
 
@@ -56,7 +56,7 @@ 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 parent_permissions = state.borrow_mut::<PermissionsContainer>();
   let worker_permissions = parent_permissions.create_child_permissions(args)?;
@@ -147,8 +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 c3f469656c..00aafb8286 100644
--- a/cli/ops/testing.rs
+++ b/cli/ops/testing.rs
@@ -51,7 +51,7 @@ 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 parent_permissions = state.borrow_mut::<PermissionsContainer>();
   let worker_permissions = parent_permissions.create_child_permissions(args)?;
@@ -150,7 +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 {
@@ -169,7 +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 84c671268a..710b975093 100644
--- a/cli/resolver.rs
+++ b/cli/resolver.rs
@@ -4,6 +4,7 @@ use async_trait::async_trait;
 use dashmap::DashMap;
 use dashmap::DashSet;
 use deno_ast::MediaType;
+use deno_ast::ModuleKind;
 use deno_config::workspace::MappedResolution;
 use deno_config::workspace::MappedResolutionDiagnostic;
 use deno_config::workspace::MappedResolutionError;
@@ -11,6 +12,7 @@ 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;
@@ -29,6 +31,7 @@ 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::deno_node::PackageJsonResolver;
 use deno_semver::npm::NpmPackageReqReference;
 use deno_semver::package::PackageReq;
 use node_resolver::errors::ClosestPkgJsonError;
@@ -38,21 +41,22 @@ 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::errors::PackageSubpathResolveError;
+use node_resolver::InNpmPackageChecker;
 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::path::specifier_has_extension;
 use crate::util::sync::AtomicFlag;
 use crate::util::text_encoding::from_utf8_lossy_owned;
 
@@ -104,36 +108,32 @@ impl deno_resolver::fs::DenoResolverFs for CliDenoResolverFs {
 
 #[derive(Debug)]
 pub struct CliNodeResolver {
-  cjs_resolutions: Arc<CjsResolutionStore>,
+  cjs_tracker: Arc<CjsTracker>,
   fs: Arc<dyn deno_fs::FileSystem>,
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
   node_resolver: Arc<NodeResolver>,
   npm_resolver: Arc<dyn CliNpmResolver>,
 }
 
 impl CliNodeResolver {
   pub fn new(
-    cjs_resolutions: Arc<CjsResolutionStore>,
+    cjs_tracker: Arc<CjsTracker>,
     fs: Arc<dyn deno_fs::FileSystem>,
+    in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
     node_resolver: Arc<NodeResolver>,
     npm_resolver: Arc<dyn CliNpmResolver>,
   ) -> Self {
     Self {
-      cjs_resolutions,
+      cjs_tracker,
       fs,
+      in_npm_pkg_checker,
       node_resolver,
       npm_resolver,
     }
   }
 
   pub fn in_npm_package(&self, specifier: &ModuleSpecifier) -> bool {
-    self.npm_resolver.in_npm_package(specifier)
-  }
-
-  pub fn get_closest_package_json(
-    &self,
-    referrer: &ModuleSpecifier,
-  ) -> Result<Option<Arc<PackageJson>>, ClosestPkgJsonError> {
-    self.node_resolver.get_closest_package_json(referrer)
+    self.in_npm_pkg_checker.in_npm_package(specifier)
   }
 
   pub fn resolve_if_for_npm_pkg(
@@ -153,8 +153,7 @@ impl CliNodeResolver {
           | NodeResolveErrorKind::UnsupportedEsmUrlScheme(_)
           | NodeResolveErrorKind::DataUrlReferrer(_)
           | NodeResolveErrorKind::TypesNotFound(_)
-          | NodeResolveErrorKind::FinalizeResolution(_)
-          | NodeResolveErrorKind::UrlToNodeResolution(_) => Err(err.into()),
+          | NodeResolveErrorKind::FinalizeResolution(_) => Err(err.into()),
           NodeResolveErrorKind::PackageResolve(err) => {
             let err = err.into_kind();
             match err {
@@ -216,7 +215,11 @@ impl CliNodeResolver {
     referrer: &ModuleSpecifier,
     mode: NodeResolutionMode,
   ) -> Result<NodeResolution, NodeResolveError> {
-    let referrer_kind = if self.cjs_resolutions.is_known_cjs(referrer) {
+    let referrer_kind = if self
+      .cjs_tracker
+      .is_maybe_cjs(referrer, MediaType::from_specifier(referrer))
+      .map_err(|err| NodeResolveErrorKind::PackageResolve(err.into()))?
+    {
       NodeModuleKind::Cjs
     } else {
       NodeModuleKind::Esm
@@ -226,7 +229,7 @@ impl CliNodeResolver {
       self
         .node_resolver
         .resolve(specifier, referrer, referrer_kind, mode)?;
-    Ok(self.handle_node_resolution(res))
+    Ok(res)
   }
 
   pub fn resolve_req_reference(
@@ -234,7 +237,7 @@ impl CliNodeResolver {
     req_ref: &NpmPackageReqReference,
     referrer: &ModuleSpecifier,
     mode: NodeResolutionMode,
-  ) -> Result<NodeResolution, AnyError> {
+  ) -> Result<ModuleSpecifier, AnyError> {
     self.resolve_req_with_sub_path(
       req_ref.req(),
       req_ref.sub_path(),
@@ -249,7 +252,7 @@ impl CliNodeResolver {
     sub_path: Option<&str>,
     referrer: &ModuleSpecifier,
     mode: NodeResolutionMode,
-  ) -> Result<NodeResolution, AnyError> {
+  ) -> Result<ModuleSpecifier, AnyError> {
     let package_folder = self
       .npm_resolver
       .resolve_pkg_folder_from_deno_module_req(req, referrer)?;
@@ -260,7 +263,7 @@ impl CliNodeResolver {
       mode,
     );
     match resolution_result {
-      Ok(resolution) => Ok(resolution),
+      Ok(url) => Ok(url),
       Err(err) => {
         if self.npm_resolver.as_byonm().is_some() {
           let package_json_path = package_folder.join("package.json");
@@ -271,7 +274,7 @@ impl CliNodeResolver {
             ));
           }
         }
-        Err(err)
+        Err(err.into())
       }
     }
   }
@@ -282,16 +285,13 @@ impl CliNodeResolver {
     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))
+  ) -> Result<ModuleSpecifier, PackageSubpathResolveError> {
+    self.node_resolver.resolve_package_subpath_from_deno_module(
+      package_folder,
+      sub_path,
+      maybe_referrer,
+      mode,
+    )
   }
 
   pub fn handle_if_in_node_modules(
@@ -306,71 +306,45 @@ impl CliNodeResolver {
       // 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)?;
-        let resolution = self.handle_node_resolution(resolution);
-        return Ok(Some(resolution.into_url()));
-      }
+      let specifier = crate::node::resolve_specifier_into_node_modules(
+        specifier,
+        self.fs.as_ref(),
+      );
+      return Ok(Some(specifier));
     }
 
     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.mark_cjs_resolution(specifier.clone());
-    }
-    resolution
-  }
-
-  pub fn mark_cjs_resolution(&self, specifier: ModuleSpecifier) {
-    self.cjs_resolutions.insert(specifier);
-  }
 }
 
-// todo(dsherret): move to module_loader.rs
+#[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 fn if_in_npm_package(&self, specifier: &ModuleSpecifier) -> bool {
-    self.node_resolver.in_npm_package(specifier)
-      || self.cjs_resolutions.is_known_cjs(specifier)
-  }
-
   pub async fn load(
     &self,
     specifier: &ModuleSpecifier,
@@ -413,20 +387,30 @@ impl NpmModuleLoader {
         }
       })?;
 
-    let code = if self.cjs_resolutions.is_known_cjs(specifier) {
+    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 = 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(),
@@ -435,21 +419,165 @@ impl NpmModuleLoader {
   }
 }
 
+pub struct CjsTrackerOptions {
+  pub unstable_detect_cjs: bool,
+}
+
 /// Keeps track of what module specifiers were resolved as CJS.
-#[derive(Debug, Default)]
-pub struct CjsResolutionStore(DashSet<ModuleSpecifier>);
+///
+/// Modules that are `.js` or `.ts` 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 {
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+  pkg_json_resolver: Arc<PackageJsonResolver>,
+  unstable_detect_cjs: bool,
+  known: DashMap<ModuleSpecifier, ModuleKind>,
+}
 
-impl CjsResolutionStore {
-  pub fn is_known_cjs(&self, specifier: &ModuleSpecifier) -> bool {
-    if specifier.scheme() != "file" {
-      return false;
+impl CjsTracker {
+  pub fn new(
+    in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+    pkg_json_resolver: Arc<PackageJsonResolver>,
+    options: CjsTrackerOptions,
+  ) -> Self {
+    Self {
+      in_npm_pkg_checker,
+      pkg_json_resolver,
+      unstable_detect_cjs: options.unstable_detect_cjs,
+      known: Default::default(),
     }
-
-    specifier_has_extension(specifier, "cjs") || self.0.contains(specifier)
   }
 
-  pub fn insert(&self, specifier: ModuleSpecifier) {
-    self.0.insert(specifier);
+  /// 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: &ModuleSpecifier,
+    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: &ModuleSpecifier,
+    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: &ModuleSpecifier,
+    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.check_based_on_pkg_json(specifier)?,
+    };
+    Ok(kind.is_cjs())
+  }
+
+  pub fn get_known_kind(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+  ) -> Option<ModuleKind> {
+    self.get_known_kind_with_is_script(specifier, media_type, None)
+  }
+
+  fn get_known_kind_with_is_script(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+    is_script: Option<bool>,
+  ) -> Option<ModuleKind> {
+    if specifier.scheme() != "file" {
+      return Some(ModuleKind::Esm);
+    }
+
+    match media_type {
+      MediaType::Mts | MediaType::Mjs | MediaType::Dmts => Some(ModuleKind::Esm),
+      MediaType::Cjs | MediaType::Cts | MediaType::Dcts => Some(ModuleKind::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) = self.known.get(specifier).map(|v| *v) {
+          Some(value)
+        } else {
+          let value = self.check_based_on_pkg_json(specifier).ok();
+          if let Some(value) = value {
+            self.known.insert(specifier.clone(), value);
+          }
+          Some(value.unwrap_or(ModuleKind::Esm))
+        }
+      }
+      MediaType::Wasm |
+      MediaType::Json => Some(ModuleKind::Esm),
+      MediaType::JavaScript
+      | MediaType::Jsx
+      | MediaType::TypeScript
+      | MediaType::Tsx
+      // treat these as unknown
+      | MediaType::Css
+      | MediaType::SourceMap
+      | MediaType::Unknown => {
+        if let Some(value) = self.known.get(specifier).map(|v| *v) {
+          if value.is_cjs() && is_script == Some(false) {
+            // we now know this is actually esm
+            self.known.insert(specifier.clone(), ModuleKind::Esm);
+            Some(ModuleKind::Esm)
+          } else {
+            Some(value)
+          }
+        } else if is_script == Some(false) {
+          // we know this is esm
+          self.known.insert(specifier.clone(), ModuleKind::Esm);
+          Some(ModuleKind::Esm)
+        } else {
+          None
+        }
+      }
+    }
+  }
+
+  fn check_based_on_pkg_json(
+    &self,
+    specifier: &ModuleSpecifier,
+  ) -> Result<ModuleKind, 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(ModuleKind::from_is_cjs(is_file_location_cjs))
+      } else {
+        Ok(ModuleKind::Cjs)
+      }
+    } else if self.unstable_detect_cjs {
+      if let Some(pkg_json) =
+        self.pkg_json_resolver.get_closest_package_json(specifier)?
+      {
+        let is_cjs_type = pkg_json.typ == "commonjs";
+        Ok(ModuleKind::from_is_cjs(is_cjs_type))
+      } else {
+        Ok(ModuleKind::Esm)
+      }
+    } else {
+      Ok(ModuleKind::Esm)
+    }
   }
 }
 
@@ -633,8 +761,7 @@ impl Resolver for CliGraphResolver {
             Some(referrer),
             to_node_mode(mode),
           )
-          .map_err(ResolveError::Other)
-          .map(|res| res.into_url()),
+          .map_err(|e| ResolveError::Other(e.into())),
         MappedResolution::PackageJson {
           dep_result,
           alias,
@@ -665,19 +792,17 @@ impl Resolver for CliGraphResolver {
                 )
                 .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(),
-                  )
+                  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),
+                    )
+                    .map_err(|e| ResolveError::Other(e.into()))
                 }),
             })
         }
@@ -717,23 +842,20 @@ impl Resolver for CliGraphResolver {
               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(),
-            );
+            return node_resolver
+              .resolve_package_sub_path_from_deno_module(
+                pkg_folder,
+                npm_req_ref.sub_path(),
+                Some(referrer),
+                to_node_mode(mode),
+              )
+              .map_err(|e| ResolveError::Other(e.into()));
           }
 
           // 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());
           }
         }
@@ -751,9 +873,7 @@ impl Resolver for CliGraphResolver {
             .map_err(ResolveError::Other)?;
           if let Some(res) = maybe_resolution {
             match res {
-              NodeResolution::Esm(url) | NodeResolution::CommonJs(url) => {
-                return Ok(url)
-              }
+              NodeResolution::Module(url) => return Ok(url),
               NodeResolution::BuiltIn(_) => {
                 // don't resolve bare specifiers for built-in modules via node resolution
               }
diff --git a/cli/schemas/config-file.v1.json b/cli/schemas/config-file.v1.json
index 4a6239f0d4..27c8499ea2 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
@@ -531,6 +531,7 @@
           "detect-cjs",
           "ffi",
           "fs",
+          "fmt-component",
           "http",
           "kv",
           "net",
diff --git a/cli/standalone/binary.rs b/cli/standalone/binary.rs
index 52ee4eeb28..9e26512268 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 +35,22 @@ 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_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 +63,12 @@ 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 +76,63 @@ 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 {
@@ -120,78 +187,23 @@ pub struct Metadata {
   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))
-}
-
 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 +213,11 @@ 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 +233,67 @@ 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 +301,67 @@ 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 +372,9 @@ 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 +382,9 @@ impl<'a> DenoCompileBinaryWriter<'a> {
     npm_system_info: NpmSystemInfo,
   ) -> Self {
     Self {
+      cjs_tracker,
       deno_dir,
+      emitter,
       file_fetcher,
       http_client_provider,
       npm_resolver,
@@ -362,8 +396,8 @@ 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 +424,17 @@ 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(
@@ -493,12 +529,12 @@ 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,
@@ -512,19 +548,17 @@ 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| {
@@ -536,18 +570,16 @@ 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| {
@@ -560,9 +592,69 @@ 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) => {
@@ -636,14 +728,14 @@ impl<'a> DenoCompileBinaryWriter<'a> {
       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,
@@ -664,8 +756,9 @@ 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
@@ -675,12 +768,12 @@ 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) {
@@ -715,6 +808,8 @@ 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 314444630b..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<()> {
diff --git a/cli/standalone/mod.rs b/cli/standalone/mod.rs
index 60018228b7..85610f4c20 100644
--- a/cli/standalone/mod.rs
+++ b/cli/standalone/mod.rs
@@ -5,6 +5,8 @@
 #![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;
@@ -17,6 +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;
@@ -28,7 +31,9 @@ use deno_npm::npm_rc::ResolvedNpmRc;
 use deno_package_json::PackageJsonDepValue;
 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;
@@ -38,10 +43,10 @@ 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::NodeResolutionMode;
+use serialization::DenoCompileModuleSource;
 use std::borrow::Cow;
 use std::rc::Rc;
 use std::sync::Arc;
@@ -54,17 +59,24 @@ 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::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::resolver::CjsResolutionStore;
+use crate::npm::CreateInNpmPkgCheckerOptions;
+use crate::resolver::CjsTracker;
+use crate::resolver::CjsTrackerOptions;
 use crate::resolver::CliDenoResolverFs;
 use crate::resolver::CliNodeResolver;
 use crate::resolver::NpmModuleLoader;
@@ -73,60 +85,30 @@ 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,
+  cjs_tracker: Arc<CjsTracker>,
+  fs: Arc<dyn deno_fs::FileSystem>,
+  modules: StandaloneModules,
+  node_code_translator: Arc<CliNodeCodeTranslator>,
   node_resolver: Arc<CliNodeResolver>,
   npm_module_loader: Arc<NpmModuleLoader>,
+  npm_resolver: Arc<dyn CliNpmResolver>,
+  workspace_resolver: WorkspaceResolver,
 }
 
 #[derive(Clone)]
@@ -134,6 +116,12 @@ 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";
 
@@ -191,8 +179,7 @@ impl ModuleLoader for EmbeddedModuleLoader {
             sub_path.as_deref(),
             Some(&referrer),
             NodeResolutionMode::Execution,
-          )?
-          .into_url(),
+          )?,
       ),
       Ok(MappedResolution::PackageJson {
         dep_result,
@@ -200,16 +187,14 @@ impl ModuleLoader for EmbeddedModuleLoader {
         alias,
         ..
       }) => match dep_result.as_ref().map_err(|e| AnyError::from(e.clone()))? {
-        PackageJsonDepValue::Req(req) => self
-          .shared
-          .node_resolver
-          .resolve_req_with_sub_path(
+        PackageJsonDepValue::Req(req) => {
+          self.shared.node_resolver.resolve_req_with_sub_path(
             req,
             sub_path.as_deref(),
             &referrer,
             NodeResolutionMode::Execution,
           )
-          .map(|res| res.into_url()),
+        }
         PackageJsonDepValue::Workspace(version_req) => {
           let pkg_folder = self
             .shared
@@ -227,8 +212,7 @@ impl ModuleLoader for EmbeddedModuleLoader {
                 sub_path.as_deref(),
                 Some(&referrer),
                 NodeResolutionMode::Execution,
-              )?
-              .into_url(),
+              )?,
           )
         }
       },
@@ -237,20 +221,18 @@ 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 self.shared.node_resolver.resolve_req_reference(
+            &reference,
+            &referrer,
+            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());
           }
         }
 
@@ -345,82 +327,140 @@ 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)?)
+  }
 }
 
 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()
   }
 }
 
@@ -439,13 +479,15 @@ 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,
@@ -459,44 +501,50 @@ 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(
-    &RealDenoCacheEnv,
-    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,
@@ -505,50 +553,54 @@ 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(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,
@@ -557,42 +609,52 @@ 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()),
+    in_npm_pkg_checker.clone(),
     npm_resolver.clone().into_npm_resolver(),
+    pkg_json_resolver.clone(),
+  ));
+  let cjs_tracker = Arc::new(CjsTracker::new(
+    in_npm_pkg_checker.clone(),
+    pkg_json_resolver.clone(),
+    CjsTrackerOptions {
+      unstable_detect_cjs: metadata.unstable_config.detect_cjs,
+    },
   ));
-  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(),
+    cjs_tracker.clone(),
     fs.clone(),
+    in_npm_pkg_checker.clone(),
     node_resolver.clone(),
     npm_resolver.clone(),
   ));
   let cjs_esm_code_analyzer = CliCjsCodeAnalyzer::new(
     node_analysis_cache,
+    cjs_tracker.clone(),
     fs.clone(),
-    cli_node_resolver.clone(),
     None,
+    false,
   );
   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(),
+    pkg_json_resolver.clone(),
   ));
   let workspace_resolver = {
     let import_map = match metadata.workspace_resolver.import_map {
@@ -645,37 +707,35 @@ pub async fn run(
   };
   let module_loader_factory = StandaloneModuleLoaderFactory {
     shared: Arc::new(SharedModuleLoaderState {
-      eszip: WorkspaceEszip {
-        eszip,
-        root_dir_url,
-      },
-      workspace_resolver,
+      cjs_tracker: cjs_tracker.clone(),
+      fs: fs.clone(),
+      modules,
+      node_code_translator: node_code_translator.clone(),
       node_resolver: cli_node_resolver.clone(),
       npm_module_loader: Arc::new(NpmModuleLoader::new(
-        cjs_resolutions.clone(),
-        node_code_translator,
+        cjs_tracker.clone(),
         fs.clone(),
-        cli_node_resolver,
+        node_code_translator,
       )),
+      npm_resolver: npm_resolver.clone(),
+      workspace_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()]);
       }
     }
 
@@ -697,7 +757,6 @@ pub async fn run(
   });
   let worker_factory = CliMainWorkerFactory::new(
     Arc::new(BlobStore::default()),
-    cjs_resolutions,
     // Code cache is not supported for standalone binary yet.
     None,
     feature_checker,
@@ -708,6 +767,7 @@ pub async fn run(
     Box::new(module_loader_factory),
     node_resolver,
     npm_resolver,
+    pkg_json_resolver,
     root_cert_store_provider,
     permissions,
     StorageKeyResolver::empty(),
@@ -723,7 +783,6 @@ 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)
@@ -740,7 +799,6 @@ pub async fn run(
       node_ipc: None,
       serve_port: None,
       serve_host: None,
-      unstable_detect_cjs: metadata.unstable_config.detect_cjs,
     },
   );
 
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..0ae00accbf 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<_>>(),
@@ -751,14 +795,14 @@ 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 +871,15 @@ 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 +888,27 @@ 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 +946,7 @@ 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 +959,23 @@ 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 +1092,7 @@ 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 +1143,7 @@ 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 418043b23f..43840e868d 100644
--- a/cli/task_runner.rs
+++ b/cli/task_runner.rs
@@ -155,6 +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,
@@ -204,7 +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('-'))
@@ -267,10 +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 3cc4414fcb..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()?;
@@ -54,16 +53,6 @@ pub async fn compile(
     );
   }
 
-  if cli_options.unstable_detect_cjs() {
-    log::warn!(
-      concat!(
-        "{} --unstable-detect-cjs is not properly supported in deno compile. ",
-        "The compiled executable may encounter runtime errors.",
-      ),
-      crate::colors::yellow("Warning"),
-    );
-  }
-
   let output_path = resolve_compile_executable_output_path(
     http_client,
     &compile_flags,
@@ -80,7 +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?
@@ -91,11 +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(
@@ -106,17 +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"),
@@ -143,15 +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..f593332475 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();
@@ -468,7 +486,7 @@ fn filter_coverages(
         || 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 5e18546a28..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 => {
diff --git a/cli/tools/fmt.rs b/cli/tools/fmt.rs
index 8a4bc4e6c8..f7f8dabc6f 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)?;
@@ -978,6 +993,7 @@ 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 +1032,7 @@ 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 +1052,7 @@ 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 {
diff --git a/cli/tools/info.rs b/cli/tools/info.rs
index 3febaff579..c2f5a8cb8d 100644
--- a/cli/tools/info.rs
+++ b/cli/tools/info.rs
@@ -530,7 +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),
     }
 
@@ -538,7 +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()),
@@ -645,10 +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/registry/pm.rs b/cli/tools/registry/pm.rs
index 02731d3039..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;
@@ -38,236 +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.dependencies.swap_remove(&name);
-      self.dev_dependencies.insert(name, version);
-    } else {
-      self.dev_dependencies.swap_remove(&name);
-      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;
@@ -275,76 +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();
   }
 }
 
@@ -401,11 +291,27 @@ impl std::fmt::Display for AddCommandName {
 fn load_configs(
   flags: &Arc<Flags>,
   has_jsr_specifiers: impl FnOnce() -> bool,
-) -> Result<(CliFactory, Option<NpmConfig>, Option<DenoConfig>), AnyError> {
+) -> 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() && !has_jsr_specifiers() => {
       (cli_factory, None)
@@ -413,11 +319,16 @@ fn load_configs(
     _ => {
       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)?,
+        )?),
       )
     }
   };
@@ -425,20 +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, || {
-    add_flags.packages.iter().any(|s| s.starts_with("jsr:"))
-  })?;
-  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. ",
@@ -446,11 +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(
@@ -461,10 +393,14 @@ 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());
@@ -521,15 +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);
       }
@@ -545,7 +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 {
@@ -558,18 +511,11 @@ 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()?;
   }
 
   npm_install_after_modification(flags, Some(jsr_resolver)).await?;
@@ -584,76 +530,144 @@ 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: AddRmPackageReq,
 ) -> Result<PackageAndVersion, AnyError> {
-  match add_package_req.value {
-    AddRmPackageReqValue::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 if req.version_req.version_text() == nv.version.to_string() {
-        ""
-      } 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
     }
-    AddRmPackageReqValue::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 if req.version_req.version_text() == nv.version.to_string() {
-        ""
-      } 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
     }
   }
 }
@@ -754,33 +768,13 @@ impl AddRmPackageReq {
   }
 }
 
-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() {
-    if index == 0 {
-      contents.push(String::new()); // force a newline at the start
-    }
-    // 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, || 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![];
 
@@ -817,7 +811,7 @@ pub async fn remove(
       log::info!("Removed {}", crate::colors::green(package));
     }
     for config in configs.into_iter().flatten() {
-      config.commit().await?;
+      config.commit()?;
     }
 
     npm_install_after_modification(flags, None).await?;
@@ -844,88 +838,11 @@ async fn npm_install_after_modification(
   // npm install
   cache_deps::cache_top_level_deps(&cli_factory, jsr_resolver).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(),
-          })
-        }
-      }
-
-      // 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!(),
-    }
+  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)]
diff --git a/cli/tools/registry/pm/cache_deps.rs b/cli/tools/registry/pm/cache_deps.rs
index b4cd1c2532..d3c8da868c 100644
--- a/cli/tools/registry/pm/cache_deps.rs
+++ b/cli/tools/registry/pm/cache_deps.rs
@@ -44,7 +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;
       };
@@ -89,10 +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/repl/session.rs b/cli/tools/repl/session.rs
index 484664dae4..23b0f11ac5 100644
--- a/cli/tools/repl/session.rs
+++ b/cli/tools/repl/session.rs
@@ -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;
@@ -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
diff --git a/cli/tools/run/hmr.rs b/cli/tools/run/hmr.rs
index 6ccf8e344b..6cebedd012 100644
--- a/cli/tools/run/hmr.rs
+++ b/cli/tools/run/hmr.rs
@@ -1,9 +1,11 @@
 // 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_ast::MediaType;
+use deno_ast::ModuleKind;
 use deno_core::error::generic_error;
 use deno_core::error::AnyError;
 use deno_core::futures::StreamExt;
@@ -12,11 +14,14 @@ 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::resolver::CjsTracker;
+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",
@@ -58,6 +63,7 @@ pub struct HmrRunner {
   session: LocalInspectorSession,
   watcher_communicator: Arc<WatcherCommunicator>,
   script_ids: HashMap<String, String>,
+  cjs_tracker: Arc<CjsTracker>,
   emitter: Arc<Emitter>,
 }
 
@@ -139,7 +145,8 @@ impl crate::worker::HmrRunner for HmrRunner {
             };
 
             let source_code = self.emitter.load_and_emit_for_hmr(
-              &module_url
+              &module_url,
+              ModuleKind::from_is_cjs(self.cjs_tracker.is_maybe_cjs(&module_url, MediaType::from_specifier(&module_url))?),
             ).await?;
 
             let mut tries = 1;
@@ -172,12 +179,14 @@ impl crate::worker::HmrRunner for HmrRunner {
 
 impl HmrRunner {
   pub fn new(
+    cjs_tracker: Arc<CjsTracker>,
     emitter: Arc<Emitter>,
     session: LocalInspectorSession,
     watcher_communicator: Arc<WatcherCommunicator>,
   ) -> Self {
     Self {
       session,
+      cjs_tracker,
       emitter,
       watcher_communicator,
       script_ids: HashMap::new(),
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/test/mod.rs b/cli/tools/test/mod.rs
index e81abad0b2..fa849614fa 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(()),
diff --git a/cli/tools/upgrade.rs b/cli/tools/upgrade.rs
index b1b09d1a6f..77a9f72b80 100644
--- a/cli/tools/upgrade.rs
+++ b/cli/tools/upgrade.rs
@@ -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 {
@@ -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:' $_.ProcessId
+  }
+}"#,
+    ])
+    .stdout(get_pipe())
+    .stderr(get_pipe())
+    .output();
+}
+
 fn set_exe_permissions(
   current_exe_path: &Path,
   output_exe_path: &Path,
diff --git a/cli/tsc/99_main_compiler.js b/cli/tsc/99_main_compiler.js
index 719f2b9824..52c9134dad 100644
--- a/cli/tsc/99_main_compiler.js
+++ b/cli/tsc/99_main_compiler.js
@@ -516,7 +516,6 @@ delete Object.prototype.__proto__;
   /** @typedef {{
    *    ls: ts.LanguageService & { [k:string]: any },
    *    compilerOptions: ts.CompilerOptions,
-   *    forceEnabledVerbatimModuleSyntax: boolean,
    *  }} LanguageServiceEntry */
   /** @type {{ unscoped: LanguageServiceEntry, byScope: Map<string, LanguageServiceEntry> }} */
   const languageServiceEntries = {
@@ -802,13 +801,18 @@ delete Object.prototype.__proto__;
       if (logDebug) {
         debug(`host.getScriptSnapshot("${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) {
@@ -846,6 +850,8 @@ 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 +1032,7 @@ 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 +1047,11 @@ 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 +1148,10 @@ 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 +1217,8 @@ 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()) {
@@ -1305,7 +1283,7 @@ 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 +1344,12 @@ 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..6e0e84b687 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.
diff --git a/cli/tsc/mod.rs b/cli/tsc/mod.rs
index 0e3387494a..dc7fc38f7a 100644
--- a/cli/tsc/mod.rs
+++ b/cli/tsc/mod.rs
@@ -3,8 +3,11 @@
 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::npm::ResolvePkgFolderFromDenoReqError;
+use crate::resolver::CjsTracker;
 use crate::util::checksum;
 use crate::util::path::mapped_specifier_for_tsc;
 
@@ -31,12 +34,13 @@ use deno_graph::GraphKind;
 use deno_graph::Module;
 use deno_graph::ModuleGraph;
 use deno_graph::ResolutionResolved;
+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 +49,7 @@ use std::fmt;
 use std::path::Path;
 use std::path::PathBuf;
 use std::sync::Arc;
+use thiserror::Error;
 
 mod diagnostics;
 
@@ -299,8 +304,76 @@ 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 {
+    if let Some(module_kind) =
+      self.cjs_tracker.get_known_kind(specifier, media_type)
+    {
+      module_kind.is_cjs()
+    } else {
+      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)
+        })
+    }
+  }
+}
+
 #[derive(Debug)]
 pub struct RequestNpmState {
+  pub cjs_tracker: Arc<TypeCheckingCjsTracker>,
   pub node_resolver: Arc<NodeResolver>,
   pub npm_resolver: Arc<dyn CliNpmResolver>,
 }
@@ -453,7 +526,7 @@ 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 +559,22 @@ 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 +627,9 @@ fn op_load_inner(
       match module {
         Module::Js(module) => {
           media_type = module.media_type;
+          if matches!(media_type, MediaType::Cjs | MediaType::Cts) {
+            is_cjs = true;
+          }
           let source = module
             .fast_check_module()
             .map(|m| &*m.source)
@@ -570,11 +643,13 @@ 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 +662,7 @@ 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,
       )?))
@@ -688,12 +763,30 @@ fn op_resolve_inner(
       Some(ResolutionResolved { specifier, .. }) => {
         resolve_graph_specifier_types(specifier, &referrer, state)?
       }
-      _ => resolve_non_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()),
+        }
+      }
     };
     let result = match maybe_result {
       Some((specifier, media_type)) => {
@@ -718,7 +811,13 @@ 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(),
@@ -789,41 +888,50 @@ fn resolve_graph_specifier_types(
             Some(referrer),
             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 +939,7 @@ 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 +947,8 @@ 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)
@@ -858,17 +967,15 @@ fn resolve_non_graph_specifier_types(
       Some(referrer),
       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)
   }
diff --git a/cli/util/extract.rs b/cli/util/extract.rs
index 873b7e7f2d..f577cbefec 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(),
@@ -570,14 +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,
@@ -1416,7 +1416,7 @@ console.log(Foo);
       })
       .unwrap();
 
-      collector.visit_program(parsed.program_ref());
+      parsed.program_ref().visit_with(&mut collector);
       collector
     }
 
diff --git a/cli/util/file_watcher.rs b/cli/util/file_watcher.rs
index d92d880bc1..8d734af88e 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 {
diff --git a/cli/util/fs.rs b/cli/util/fs.rs
index 2c34f486ad..d36c02242c 100644
--- a/cli/util/fs.rs
+++ b/cli/util/fs.rs
@@ -565,7 +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));
         }
       }
diff --git a/cli/util/logger.rs b/cli/util/logger.rs
index cdc89411fe..d93753dfd3 100644
--- a/cli/util/logger.rs
+++ b/cli/util/logger.rs
@@ -65,6 +65,8 @@ 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/path.rs b/cli/util/path.rs
index e4ae6e7cb1..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!(
@@ -350,18 +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/text_encoding.rs b/cli/util/text_encoding.rs
index 0b7601cb9c..8524e63ebb 100644
--- a/cli/util/text_encoding.rs
+++ b/cli/util/text_encoding.rs
@@ -97,12 +97,28 @@ 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/worker.rs b/cli/worker.rs
index e230197d2b..baacd681a1 100644
--- a/cli/worker.rs
+++ b/cli/worker.rs
@@ -14,16 +14,17 @@ 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;
@@ -42,7 +43,6 @@ use deno_runtime::WorkerExecutionMode;
 use deno_runtime::WorkerLogLevel;
 use deno_semver::npm::NpmPackageReqReference;
 use deno_terminal::colors;
-use node_resolver::NodeResolution;
 use node_resolver::NodeResolutionMode;
 use tokio::select;
 
@@ -51,28 +51,27 @@ use crate::args::DenoSubcommand;
 use crate::args::StorageKeyResolver;
 use crate::errors;
 use crate::npm::CliNpmResolver;
-use crate::resolver::CjsResolutionStore;
 use crate::util::checksum;
 use crate::util::file_watcher::WatcherCommunicator;
 use crate::util::file_watcher::WatcherRestartMode;
-use crate::util::path::specifier_has_extension;
 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)]
@@ -109,7 +108,6 @@ 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>,
@@ -122,13 +120,11 @@ pub struct CliMainWorkerOptions {
   pub node_ipc: Option<i64>,
   pub serve_port: Option<u16>,
   pub serve_host: Option<String>,
-  pub unstable_detect_cjs: bool,
 }
 
 struct SharedWorkerState {
   blob_store: Arc<BlobStore>,
   broadcast_channel: InMemoryBroadcastChannel,
-  cjs_resolution_store: Arc<CjsResolutionStore>,
   code_cache: Option<Arc<dyn code_cache::CodeCache>>,
   compiled_wasm_module_store: CompiledWasmModuleStore,
   feature_checker: Arc<FeatureChecker>,
@@ -139,6 +135,7 @@ struct SharedWorkerState {
   module_loader_factory: Box<dyn ModuleLoaderFactory>,
   node_resolver: Arc<NodeResolver>,
   npm_resolver: Arc<dyn CliNpmResolver>,
+  pkg_json_resolver: Arc<PackageJsonResolver>,
   root_cert_store_provider: Arc<dyn RootCertStoreProvider>,
   root_permissions: PermissionsContainer,
   shared_array_buffer_store: SharedArrayBufferStore,
@@ -148,11 +145,15 @@ struct SharedWorkerState {
 }
 
 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(),
+      pkg_json_resolver: self.pkg_json_resolver.clone(),
     }
   }
 
@@ -163,7 +164,6 @@ impl SharedWorkerState {
 
 pub struct CliMainWorker {
   main_module: ModuleSpecifier,
-  is_main_cjs: bool,
   worker: MainWorker,
   shared: Arc<SharedWorkerState>,
 }
@@ -185,17 +185,7 @@ 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 {
@@ -283,22 +273,7 @@ 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;
 
@@ -339,24 +314,13 @@ 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
   }
 
@@ -426,7 +390,6 @@ impl CliMainWorkerFactory {
   #[allow(clippy::too_many_arguments)]
   pub fn new(
     blob_store: Arc<BlobStore>,
-    cjs_resolution_store: Arc<CjsResolutionStore>,
     code_cache: Option<Arc<dyn code_cache::CodeCache>>,
     feature_checker: Arc<FeatureChecker>,
     fs: Arc<dyn deno_fs::FileSystem>,
@@ -436,6 +399,7 @@ impl CliMainWorkerFactory {
     module_loader_factory: Box<dyn ModuleLoaderFactory>,
     node_resolver: Arc<NodeResolver>,
     npm_resolver: Arc<dyn CliNpmResolver>,
+    pkg_json_resolver: Arc<PackageJsonResolver>,
     root_cert_store_provider: Arc<dyn RootCertStoreProvider>,
     root_permissions: PermissionsContainer,
     storage_key_resolver: StorageKeyResolver,
@@ -446,7 +410,6 @@ impl CliMainWorkerFactory {
       shared: Arc::new(SharedWorkerState {
         blob_store,
         broadcast_channel: Default::default(),
-        cjs_resolution_store,
         code_cache,
         compiled_wasm_module_store: Default::default(),
         feature_checker,
@@ -457,6 +420,7 @@ impl CliMainWorkerFactory {
         module_loader_factory,
         node_resolver,
         npm_resolver,
+        pkg_json_resolver,
         root_cert_store_provider,
         root_permissions,
         shared_array_buffer_store: Default::default(),
@@ -492,10 +456,13 @@ impl CliMainWorkerFactory {
     stdio: deno_runtime::deno_io::Stdio,
   ) -> Result<CliMainWorker, AnyError> {
     let shared = &self.shared;
-    let ModuleLoaderAndSourceMapGetter { module_loader } = shared
+    let CreateModuleLoaderResult {
+      module_loader,
+      node_require_loader,
+    } = shared
       .module_loader_factory
       .create_for_main(permissions.clone());
-    let (main_module, is_main_cjs) = if let Ok(package_ref) =
+    let main_module = if let Ok(package_ref) =
       NpmPackageReqReference::from_specifier(&main_module)
     {
       if let Some(npm_resolver) = shared.npm_resolver.as_managed() {
@@ -515,9 +482,8 @@ 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
@@ -526,36 +492,9 @@ 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_maybe_cjs_js_ext = self.shared.options.unstable_detect_cjs
-        && specifier_has_extension(&main_module, "js")
-        && self
-          .shared
-          .node_resolver
-          .get_closest_package_json(&main_module)
-          .ok()
-          .flatten()
-          .map(|pkg_json| pkg_json.typ == "commonjs")
-          .unwrap_or(false);
-      let is_cjs = if is_maybe_cjs_js_ext {
-        // fill the cjs resolution store by preparing the module load
-        module_loader
-          .prepare_load(&main_module, None, false)
-          .await?;
-        self.shared.cjs_resolution_store.is_known_cjs(&main_module)
-      } else {
-        main_module.scheme() == "file"
-          && specifier_has_extension(&main_module, "cjs")
-      };
-      (main_module, is_cjs)
+      main_module
     };
 
     let maybe_inspector_server = shared.maybe_inspector_server.clone();
@@ -597,7 +536,9 @@ impl CliMainWorkerFactory {
       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_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(),
@@ -682,7 +623,6 @@ impl CliMainWorkerFactory {
 
     Ok(CliMainWorker {
       main_module,
-      is_main_cjs,
       worker,
       shared: shared.clone(),
     })
@@ -692,19 +632,19 @@ 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)
@@ -719,7 +659,7 @@ 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
@@ -728,7 +668,7 @@ impl CliMainWorkerFactory {
       return Ok(None);
     }
 
-    let resolution = self
+    let specifier = self
       .shared
       .node_resolver
       .resolve_package_subpath_from_deno_module(
@@ -737,19 +677,14 @@ impl CliMainWorkerFactory {
         /* referrer */ None,
         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)
     }
   }
 }
@@ -761,11 +696,13 @@ 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());
 
@@ -795,7 +732,9 @@ fn create_web_worker_callback(
       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_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()),
diff --git a/ext/broadcast_channel/Cargo.toml b/ext/broadcast_channel/Cargo.toml
index 7ca058a44a..90ac038357 100644
--- a/ext/broadcast_channel/Cargo.toml
+++ b/ext/broadcast_channel/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_broadcast_channel"
-version = "0.167.0"
+version = "0.171.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/cache/Cargo.toml b/ext/cache/Cargo.toml
index dee4d7274d..56fa0a527f 100644
--- a/ext/cache/Cargo.toml
+++ b/ext/cache/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_cache"
-version = "0.105.0"
+version = "0.109.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/cache/lib.rs b/ext/cache/lib.rs
index b9cc5427c2..524d4cea05 100644
--- a/ext/cache/lib.rs
+++ b/ext/cache/lib.rs
@@ -33,7 +33,9 @@ pub enum CacheError {
 }
 
 #[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 ],
@@ -231,7 +233,7 @@ 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 {
diff --git a/ext/cache/sqlite.rs b/ext/cache/sqlite.rs
index e4991c32f1..6efceda11e 100644
--- a/ext/cache/sqlite.rs
+++ b/ext/cache/sqlite.rs
@@ -42,7 +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");
@@ -57,18 +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 (
@@ -86,12 +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,
-      }
+      })
     }
   }
 }
diff --git a/ext/canvas/Cargo.toml b/ext/canvas/Cargo.toml
index 6ca3d76c05..4231d7c84d 100644
--- a/ext/canvas/Cargo.toml
+++ b/ext/canvas/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_canvas"
-version = "0.42.0"
+version = "0.46.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/console/01_console.js b/ext/console/01_console.js
index 3c07cf64aa..3803492b90 100644
--- a/ext/console/01_console.js
+++ b/ext/console/01_console.js
@@ -2653,6 +2653,7 @@ const HSL_PATTERN = new SafeRegExp(
 );
 
 function parseCssColor(colorString) {
+  colorString = StringPrototypeToLowerCase(colorString);
   if (colorKeywords.has(colorString)) {
     colorString = colorKeywords.get(colorString);
   }
diff --git a/ext/console/Cargo.toml b/ext/console/Cargo.toml
index f83f7138d8..80f1cca84d 100644
--- a/ext/console/Cargo.toml
+++ b/ext/console/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_console"
-version = "0.173.0"
+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 ccd81de0cc..966ccdc958 100644
--- a/ext/cron/Cargo.toml
+++ b/ext/cron/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_cron"
-version = "0.53.0"
+version = "0.57.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/crypto/Cargo.toml b/ext/crypto/Cargo.toml
index 2f970ca535..a5794dc68b 100644
--- a/ext/crypto/Cargo.toml
+++ b/ext/crypto/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_crypto"
-version = "0.187.0"
+version = "0.191.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = 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/Cargo.toml b/ext/fetch/Cargo.toml
index afffd3ffb1..56d416bbb8 100644
--- a/ext/fetch/Cargo.toml
+++ b/ext/fetch/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_fetch"
-version = "0.197.0"
+version = "0.201.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/fetch/lib.rs b/ext/fetch/lib.rs
index 4df8dc3d72..7ef26431c2 100644
--- a/ext/fetch/lib.rs
+++ b/ext/fetch/lib.rs
@@ -39,6 +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;
@@ -149,7 +150,7 @@ pub enum FetchError {
   #[error(transparent)]
   Resource(deno_core::error::AnyError),
   #[error(transparent)]
-  Permission(deno_core::error::AnyError),
+  Permission(#[from] PermissionCheckError),
   #[error("NetworkError when attempting to fetch resource")]
   NetworkError,
   #[error("Fetching files only supports the GET method: received {0}")]
@@ -346,13 +347,13 @@ pub trait FetchPermissions {
     &mut self,
     url: &Url,
     api_name: &str,
-  ) -> Result<(), deno_core::error::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>, deno_core::error::AnyError>;
+  ) -> Result<Cow<'a, Path>, PermissionCheckError>;
 }
 
 impl FetchPermissions for deno_permissions::PermissionsContainer {
@@ -361,7 +362,7 @@ impl FetchPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     url: &Url,
     api_name: &str,
-  ) -> Result<(), deno_core::error::AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_net_url(self, url, api_name)
   }
 
@@ -370,7 +371,7 @@ impl FetchPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     path: &'a Path,
     api_name: &str,
-  ) -> Result<Cow<'a, Path>, deno_core::error::AnyError> {
+  ) -> Result<Cow<'a, Path>, PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_read_path(
       self,
       path,
@@ -414,9 +415,7 @@ where
     "file" => {
       let path = url.to_file_path().map_err(|_| FetchError::NetworkError)?;
       let permissions = state.borrow_mut::<FP>();
-      let path = permissions
-        .check_read(&path, "fetch()")
-        .map_err(FetchError::Permission)?;
+      let path = permissions.check_read(&path, "fetch()")?;
       let url = match path {
         Cow::Owned(path) => Url::from_file_path(path).unwrap(),
         Cow::Borrowed(_) => url,
@@ -442,9 +441,7 @@ where
     }
     "http" | "https" => {
       let permissions = state.borrow_mut::<FP>();
-      permissions
-        .check_net_url(&url, "fetch()")
-        .map_err(FetchError::Resource)?;
+      permissions.check_net_url(&url, "fetch()")?;
 
       let maybe_authority = extract_authority(&mut url);
       let uri = url
@@ -863,9 +860,7 @@ where
   if let Some(proxy) = args.proxy.clone() {
     let permissions = state.borrow_mut::<FP>();
     let url = Url::parse(&proxy.url)?;
-    permissions
-      .check_net_url(&url, "Deno.createHttpClient()")
-      .map_err(FetchError::Permission)?;
+    permissions.check_net_url(&url, "Deno.createHttpClient()")?;
   }
 
   let options = state.borrow::<Options>();
diff --git a/ext/ffi/Cargo.toml b/ext/ffi/Cargo.toml
index 80b0180d0b..295e8be846 100644
--- a/ext/ffi/Cargo.toml
+++ b/ext/ffi/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_ffi"
-version = "0.160.0"
+version = "0.164.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -21,6 +21,7 @@ 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"
diff --git a/ext/ffi/call.rs b/ext/ffi/call.rs
index d337b29b00..bbff0ee48f 100644
--- a/ext/ffi/call.rs
+++ b/ext/ffi/call.rs
@@ -9,12 +9,14 @@ use crate::FfiPermissions;
 use crate::ForeignFunction;
 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;
@@ -30,7 +32,9 @@ pub enum CallError {
   #[error("Invalid FFI symbol name: '{0}'")]
   InvalidSymbol(String),
   #[error(transparent)]
-  Permission(deno_core::error::AnyError),
+  Permission(#[from] deno_permissions::PermissionCheckError),
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
   #[error(transparent)]
   Callback(#[from] super::CallbackError),
 }
@@ -202,6 +206,7 @@ where
 #[serde(untagged)]
 pub enum FfiValue {
   Value(Value),
+  BigInt(V8BigInt),
   External(ExternalPointer),
 }
 
@@ -251,18 +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)))
       }
@@ -298,9 +303,7 @@ where
   {
     let mut state = state.borrow_mut();
     let permissions = state.borrow_mut::<FP>();
-    permissions
-      .check_partial_no_path()
-      .map_err(CallError::Permission)?;
+    permissions.check_partial_no_path()?;
   };
 
   let symbol = PtrSymbol::new(pointer, &def)?;
@@ -344,7 +347,7 @@ pub fn op_ffi_call_nonblocking(
     let resource = state
       .resource_table
       .get::<DynamicLibraryResource>(rid)
-      .map_err(CallError::Permission)?;
+      .map_err(CallError::Resource)?;
     let symbols = &resource.symbols;
     *symbols
       .get(&symbol)
@@ -398,9 +401,7 @@ where
   {
     let mut state = state.borrow_mut();
     let permissions = state.borrow_mut::<FP>();
-    permissions
-      .check_partial_no_path()
-      .map_err(CallError::Permission)?;
+    permissions.check_partial_no_path()?;
   };
 
   let symbol = PtrSymbol::new(pointer, &def)?;
diff --git a/ext/ffi/callback.rs b/ext/ffi/callback.rs
index f33e0413a3..29583c800c 100644
--- a/ext/ffi/callback.rs
+++ b/ext/ffi/callback.rs
@@ -38,7 +38,7 @@ pub enum CallbackError {
   #[error(transparent)]
   Resource(deno_core::error::AnyError),
   #[error(transparent)]
-  Permission(deno_core::error::AnyError),
+  Permission(#[from] deno_permissions::PermissionCheckError),
   #[error(transparent)]
   Other(deno_core::error::AnyError),
 }
@@ -572,9 +572,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(CallbackError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   let thread_id: u32 = LOCAL_THREAD_ID.with(|s| {
     let value = *s.borrow();
diff --git a/ext/ffi/dlfcn.rs b/ext/ffi/dlfcn.rs
index 53bdcbc5cc..55909468f8 100644
--- a/ext/ffi/dlfcn.rs
+++ b/ext/ffi/dlfcn.rs
@@ -30,7 +30,7 @@ pub enum DlfcnError {
   #[error(transparent)]
   Dlopen(#[from] dlopen2::Error),
   #[error(transparent)]
-  Permission(deno_core::error::AnyError),
+  Permission(#[from] deno_permissions::PermissionCheckError),
   #[error(transparent)]
   Other(deno_core::error::AnyError),
 }
@@ -133,9 +133,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  let path = permissions
-    .check_partial_with_path(&args.path)
-    .map_err(DlfcnError::Permission)?;
+  let path = permissions.check_partial_with_path(&args.path)?;
 
   let lib = Library::open(&path).map_err(|e| {
     dlopen2::Error::OpeningLibraryError(std::io::Error::new(
diff --git a/ext/ffi/lib.rs b/ext/ffi/lib.rs
index 237f8c3b05..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;
@@ -31,6 +29,7 @@ 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;
@@ -48,17 +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)
   }
 
@@ -66,7 +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 2f04f4feb4..fd8a2c8e70 100644
--- a/ext/ffi/repr.rs
+++ b/ext/ffi/repr.rs
@@ -46,7 +46,7 @@ pub enum ReprError {
   #[error("Invalid pointer pointer, pointer is null")]
   InvalidPointer,
   #[error(transparent)]
-  Permission(deno_core::error::AnyError),
+  Permission(#[from] deno_permissions::PermissionCheckError),
 }
 
 #[op2(fast)]
@@ -58,9 +58,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   Ok(ptr_number as *mut c_void)
 }
@@ -75,9 +73,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   Ok(a == b)
 }
@@ -91,9 +87,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   Ok(buf as *mut c_void)
 }
@@ -107,9 +101,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   let Some(buf) = buf.get_backing_store() else {
     return Ok(0 as _);
@@ -130,9 +122,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
     return Err(ReprError::InvalidOffset);
@@ -162,9 +152,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   Ok(ptr as usize)
 }
@@ -181,9 +169,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
     return Err(ReprError::InvalidArrayBuffer);
@@ -215,9 +201,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   if src.is_null() {
     Err(ReprError::InvalidArrayBuffer)
@@ -246,9 +230,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
     return Err(ReprError::InvalidCString);
@@ -272,9 +254,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
     return Err(ReprError::InvalidBool);
@@ -294,9 +274,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
     return Err(ReprError::InvalidU8);
@@ -318,9 +296,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
     return Err(ReprError::InvalidI8);
@@ -342,9 +318,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
     return Err(ReprError::InvalidU16);
@@ -366,9 +340,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
     return Err(ReprError::InvalidI16);
@@ -390,9 +362,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
     return Err(ReprError::InvalidU32);
@@ -412,9 +382,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
     return Err(ReprError::InvalidI32);
@@ -437,9 +405,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
     return Err(ReprError::InvalidU64);
@@ -465,9 +431,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
     return Err(ReprError::InvalidI64);
@@ -490,9 +454,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
     return Err(ReprError::InvalidF32);
@@ -512,9 +474,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
     return Err(ReprError::InvalidF64);
@@ -534,9 +494,7 @@ where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions
-    .check_partial_no_path()
-    .map_err(ReprError::Permission)?;
+  permissions.check_partial_no_path()?;
 
   if ptr.is_null() {
     return Err(ReprError::InvalidPointer);
diff --git a/ext/fs/Cargo.toml b/ext/fs/Cargo.toml
index ab0bf22fd3..e85f349b15 100644
--- a/ext/fs/Cargo.toml
+++ b/ext/fs/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_fs"
-version = "0.83.0"
+version = "0.87.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -31,7 +31,7 @@ serde.workspace = true
 thiserror.workspace = true
 
 [target.'cfg(unix)'.dependencies]
-nix = { workspace = true, features = ["user"] }
+nix = { workspace = true, features = ["fs", "user"] }
 
 [target.'cfg(windows)'.dependencies]
 winapi = { workspace = true, features = ["winbase"] }
diff --git a/ext/fs/lib.rs b/ext/fs/lib.rs
index cd2baf22a9..dd852e6be8 100644
--- a/ext/fs/lib.rs
+++ b/ext/fs/lib.rs
@@ -22,8 +22,8 @@ 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;
@@ -42,45 +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,
@@ -140,7 +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)
   }
 
@@ -148,7 +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,
@@ -160,7 +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,
     )
@@ -170,7 +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)
   }
 
@@ -178,7 +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,
     )
@@ -188,7 +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,
     )
@@ -199,17 +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 a3f59da4ea..9b76b49e61 100644
--- a/ext/fs/ops.rs
+++ b/ext/fs/ops.rs
@@ -10,6 +10,12 @@ use std::path::PathBuf;
 use std::path::StripPrefixError;
 use std::rc::Rc;
 
+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;
@@ -20,18 +26,12 @@ 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}")]
@@ -39,7 +39,7 @@ pub enum FsOpsError {
   #[error("{0}")]
   OperationError(#[source] OperationError),
   #[error(transparent)]
-  Permission(deno_core::error::AnyError),
+  Permission(#[from] PermissionCheckError),
   #[error(transparent)]
   Resource(deno_core::error::AnyError),
   #[error("File name or path {0:?} is not valid UTF-8")]
@@ -150,8 +150,7 @@ where
   let path = fs.cwd()?;
   state
     .borrow_mut::<P>()
-    .check_read_blind(&path, "CWD", "Deno.cwd()")
-    .map_err(FsOpsError::Permission)?;
+    .check_read_blind(&path, "CWD", "Deno.cwd()")?;
   let path_str = path_into_string(path.into_os_string())?;
   Ok(path_str)
 }
@@ -166,8 +165,7 @@ where
 {
   let d = state
     .borrow_mut::<P>()
-    .check_read(directory, "Deno.chdir()")
-    .map_err(FsOpsError::Permission)?;
+    .check_read(directory, "Deno.chdir()")?;
   state
     .borrow::<FileSystemRc>()
     .chdir(&d)
@@ -253,8 +251,7 @@ where
 
   let path = state
     .borrow_mut::<P>()
-    .check_write(&path, "Deno.mkdirSync()")
-    .map_err(FsOpsError::Permission)?;
+    .check_write(&path, "Deno.mkdirSync()")?;
 
   let fs = state.borrow::<FileSystemRc>();
   fs.mkdir_sync(&path, recursive, Some(mode))
@@ -277,10 +274,7 @@ where
 
   let (fs, path) = {
     let mut state = state.borrow_mut();
-    let path = state
-      .borrow_mut::<P>()
-      .check_write(&path, "Deno.mkdir()")
-      .map_err(FsOpsError::Permission)?;
+    let path = state.borrow_mut::<P>().check_write(&path, "Deno.mkdir()")?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
 
@@ -302,8 +296,7 @@ where
 {
   let path = state
     .borrow_mut::<P>()
-    .check_write(&path, "Deno.chmodSync()")
-    .map_err(FsOpsError::Permission)?;
+    .check_write(&path, "Deno.chmodSync()")?;
   let fs = state.borrow::<FileSystemRc>();
   fs.chmod_sync(&path, mode).context_path("chmod", &path)?;
   Ok(())
@@ -320,10 +313,7 @@ where
 {
   let (fs, path) = {
     let mut state = state.borrow_mut();
-    let path = state
-      .borrow_mut::<P>()
-      .check_write(&path, "Deno.chmod()")
-      .map_err(FsOpsError::Permission)?;
+    let path = state.borrow_mut::<P>().check_write(&path, "Deno.chmod()")?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
   fs.chmod_async(path.clone(), mode)
@@ -344,8 +334,7 @@ where
 {
   let path = state
     .borrow_mut::<P>()
-    .check_write(&path, "Deno.chownSync()")
-    .map_err(FsOpsError::Permission)?;
+    .check_write(&path, "Deno.chownSync()")?;
   let fs = state.borrow::<FileSystemRc>();
   fs.chown_sync(&path, uid, gid)
     .context_path("chown", &path)?;
@@ -364,10 +353,7 @@ where
 {
   let (fs, path) = {
     let mut state = state.borrow_mut();
-    let path = state
-      .borrow_mut::<P>()
-      .check_write(&path, "Deno.chown()")
-      .map_err(FsOpsError::Permission)?;
+    let path = state.borrow_mut::<P>().check_write(&path, "Deno.chown()")?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
   fs.chown_async(path.clone(), uid, gid)
@@ -387,8 +373,7 @@ where
 {
   let path = state
     .borrow_mut::<P>()
-    .check_write(path, "Deno.removeSync()")
-    .map_err(FsOpsError::Permission)?;
+    .check_write(path, "Deno.removeSync()")?;
 
   let fs = state.borrow::<FileSystemRc>();
   fs.remove_sync(&path, recursive)
@@ -411,13 +396,11 @@ where
     let path = if recursive {
       state
         .borrow_mut::<P>()
-        .check_write(&path, "Deno.remove()")
-        .map_err(FsOpsError::Permission)?
+        .check_write(&path, "Deno.remove()")?
     } else {
       state
         .borrow_mut::<P>()
-        .check_write_partial(&path, "Deno.remove()")
-        .map_err(FsOpsError::Permission)?
+        .check_write_partial(&path, "Deno.remove()")?
     };
 
     (state.borrow::<FileSystemRc>().clone(), path)
@@ -440,12 +423,8 @@ where
   P: FsPermissions + 'static,
 {
   let permissions = state.borrow_mut::<P>();
-  let from = permissions
-    .check_read(from, "Deno.copyFileSync()")
-    .map_err(FsOpsError::Permission)?;
-  let to = permissions
-    .check_write(to, "Deno.copyFileSync()")
-    .map_err(FsOpsError::Permission)?;
+  let from = permissions.check_read(from, "Deno.copyFileSync()")?;
+  let to = permissions.check_write(to, "Deno.copyFileSync()")?;
 
   let fs = state.borrow::<FileSystemRc>();
   fs.copy_file_sync(&from, &to)
@@ -466,12 +445,8 @@ where
   let (fs, from, to) = {
     let mut state = state.borrow_mut();
     let permissions = state.borrow_mut::<P>();
-    let from = permissions
-      .check_read(&from, "Deno.copyFile()")
-      .map_err(FsOpsError::Permission)?;
-    let to = permissions
-      .check_write(&to, "Deno.copyFile()")
-      .map_err(FsOpsError::Permission)?;
+    let from = permissions.check_read(&from, "Deno.copyFile()")?;
+    let to = permissions.check_write(&to, "Deno.copyFile()")?;
     (state.borrow::<FileSystemRc>().clone(), from, to)
   };
 
@@ -493,8 +468,7 @@ where
 {
   let path = state
     .borrow_mut::<P>()
-    .check_read(&path, "Deno.statSync()")
-    .map_err(FsOpsError::Permission)?;
+    .check_read(&path, "Deno.statSync()")?;
   let fs = state.borrow::<FileSystemRc>();
   let stat = fs.stat_sync(&path).context_path("stat", &path)?;
   let serializable_stat = SerializableStat::from(stat);
@@ -514,9 +488,7 @@ where
   let (fs, path) = {
     let mut state = state.borrow_mut();
     let permissions = state.borrow_mut::<P>();
-    let path = permissions
-      .check_read(&path, "Deno.stat()")
-      .map_err(FsOpsError::Permission)?;
+    let path = permissions.check_read(&path, "Deno.stat()")?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
   let stat = fs
@@ -537,8 +509,7 @@ where
 {
   let path = state
     .borrow_mut::<P>()
-    .check_read(&path, "Deno.lstatSync()")
-    .map_err(FsOpsError::Permission)?;
+    .check_read(&path, "Deno.lstatSync()")?;
   let fs = state.borrow::<FileSystemRc>();
   let stat = fs.lstat_sync(&path).context_path("lstat", &path)?;
   let serializable_stat = SerializableStat::from(stat);
@@ -558,9 +529,7 @@ where
   let (fs, path) = {
     let mut state = state.borrow_mut();
     let permissions = state.borrow_mut::<P>();
-    let path = permissions
-      .check_read(&path, "Deno.lstat()")
-      .map_err(FsOpsError::Permission)?;
+    let path = permissions.check_read(&path, "Deno.lstat()")?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
   let stat = fs
@@ -581,13 +550,9 @@ where
 {
   let fs = state.borrow::<FileSystemRc>().clone();
   let permissions = state.borrow_mut::<P>();
-  let path = permissions
-    .check_read(&path, "Deno.realPathSync()")
-    .map_err(FsOpsError::Permission)?;
+  let path = permissions.check_read(&path, "Deno.realPathSync()")?;
   if path.is_relative() {
-    permissions
-      .check_read_blind(&fs.cwd()?, "CWD", "Deno.realPathSync()")
-      .map_err(FsOpsError::Permission)?;
+    permissions.check_read_blind(&fs.cwd()?, "CWD", "Deno.realPathSync()")?;
   }
 
   let resolved_path =
@@ -610,13 +575,9 @@ where
     let mut state = state.borrow_mut();
     let fs = state.borrow::<FileSystemRc>().clone();
     let permissions = state.borrow_mut::<P>();
-    let path = permissions
-      .check_read(&path, "Deno.realPath()")
-      .map_err(FsOpsError::Permission)?;
+    let path = permissions.check_read(&path, "Deno.realPath()")?;
     if path.is_relative() {
-      permissions
-        .check_read_blind(&fs.cwd()?, "CWD", "Deno.realPath()")
-        .map_err(FsOpsError::Permission)?;
+      permissions.check_read_blind(&fs.cwd()?, "CWD", "Deno.realPath()")?;
     }
     (fs, path)
   };
@@ -640,8 +601,7 @@ where
 {
   let path = state
     .borrow_mut::<P>()
-    .check_read(&path, "Deno.readDirSync()")
-    .map_err(FsOpsError::Permission)?;
+    .check_read(&path, "Deno.readDirSync()")?;
 
   let fs = state.borrow::<FileSystemRc>();
   let entries = fs.read_dir_sync(&path).context_path("readdir", &path)?;
@@ -662,8 +622,7 @@ where
     let mut state = state.borrow_mut();
     let path = state
       .borrow_mut::<P>()
-      .check_read(&path, "Deno.readDir()")
-      .map_err(FsOpsError::Permission)?;
+      .check_read(&path, "Deno.readDir()")?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
 
@@ -685,15 +644,9 @@ where
   P: FsPermissions + 'static,
 {
   let permissions = state.borrow_mut::<P>();
-  let _ = permissions
-    .check_read(&oldpath, "Deno.renameSync()")
-    .map_err(FsOpsError::Permission)?;
-  let oldpath = permissions
-    .check_write(&oldpath, "Deno.renameSync()")
-    .map_err(FsOpsError::Permission)?;
-  let newpath = permissions
-    .check_write(&newpath, "Deno.renameSync()")
-    .map_err(FsOpsError::Permission)?;
+  let _ = permissions.check_read(&oldpath, "Deno.renameSync()")?;
+  let oldpath = permissions.check_write(&oldpath, "Deno.renameSync()")?;
+  let newpath = permissions.check_write(&newpath, "Deno.renameSync()")?;
 
   let fs = state.borrow::<FileSystemRc>();
   fs.rename_sync(&oldpath, &newpath)
@@ -714,15 +667,9 @@ where
   let (fs, oldpath, newpath) = {
     let mut state = state.borrow_mut();
     let permissions = state.borrow_mut::<P>();
-    _ = permissions
-      .check_read(&oldpath, "Deno.rename()")
-      .map_err(FsOpsError::Permission)?;
-    let oldpath = permissions
-      .check_write(&oldpath, "Deno.rename()")
-      .map_err(FsOpsError::Permission)?;
-    let newpath = permissions
-      .check_write(&newpath, "Deno.rename()")
-      .map_err(FsOpsError::Permission)?;
+    _ = permissions.check_read(&oldpath, "Deno.rename()")?;
+    let oldpath = permissions.check_write(&oldpath, "Deno.rename()")?;
+    let newpath = permissions.check_write(&newpath, "Deno.rename()")?;
     (state.borrow::<FileSystemRc>().clone(), oldpath, newpath)
   };
 
@@ -743,18 +690,10 @@ where
   P: FsPermissions + 'static,
 {
   let permissions = state.borrow_mut::<P>();
-  _ = permissions
-    .check_read(oldpath, "Deno.linkSync()")
-    .map_err(FsOpsError::Permission)?;
-  let oldpath = permissions
-    .check_write(oldpath, "Deno.linkSync()")
-    .map_err(FsOpsError::Permission)?;
-  _ = permissions
-    .check_read(newpath, "Deno.linkSync()")
-    .map_err(FsOpsError::Permission)?;
-  let newpath = permissions
-    .check_write(newpath, "Deno.linkSync()")
-    .map_err(FsOpsError::Permission)?;
+  _ = permissions.check_read(oldpath, "Deno.linkSync()")?;
+  let oldpath = permissions.check_write(oldpath, "Deno.linkSync()")?;
+  _ = permissions.check_read(newpath, "Deno.linkSync()")?;
+  let newpath = permissions.check_write(newpath, "Deno.linkSync()")?;
 
   let fs = state.borrow::<FileSystemRc>();
   fs.link_sync(&oldpath, &newpath)
@@ -775,18 +714,10 @@ where
   let (fs, oldpath, newpath) = {
     let mut state = state.borrow_mut();
     let permissions = state.borrow_mut::<P>();
-    _ = permissions
-      .check_read(&oldpath, "Deno.link()")
-      .map_err(FsOpsError::Permission)?;
-    let oldpath = permissions
-      .check_write(&oldpath, "Deno.link()")
-      .map_err(FsOpsError::Permission)?;
-    _ = permissions
-      .check_read(&newpath, "Deno.link()")
-      .map_err(FsOpsError::Permission)?;
-    let newpath = permissions
-      .check_write(&newpath, "Deno.link()")
-      .map_err(FsOpsError::Permission)?;
+    _ = permissions.check_read(&oldpath, "Deno.link()")?;
+    let oldpath = permissions.check_write(&oldpath, "Deno.link()")?;
+    _ = permissions.check_read(&newpath, "Deno.link()")?;
+    let newpath = permissions.check_write(&newpath, "Deno.link()")?;
     (state.borrow::<FileSystemRc>().clone(), oldpath, newpath)
   };
 
@@ -811,12 +742,8 @@ where
   let newpath = PathBuf::from(newpath);
 
   let permissions = state.borrow_mut::<P>();
-  permissions
-    .check_write_all("Deno.symlinkSync()")
-    .map_err(FsOpsError::Permission)?;
-  permissions
-    .check_read_all("Deno.symlinkSync()")
-    .map_err(FsOpsError::Permission)?;
+  permissions.check_write_all("Deno.symlinkSync()")?;
+  permissions.check_read_all("Deno.symlinkSync()")?;
 
   let fs = state.borrow::<FileSystemRc>();
   fs.symlink_sync(&oldpath, &newpath, file_type)
@@ -841,12 +768,8 @@ where
   let fs = {
     let mut state = state.borrow_mut();
     let permissions = state.borrow_mut::<P>();
-    permissions
-      .check_write_all("Deno.symlink()")
-      .map_err(FsOpsError::Permission)?;
-    permissions
-      .check_read_all("Deno.symlink()")
-      .map_err(FsOpsError::Permission)?;
+    permissions.check_write_all("Deno.symlink()")?;
+    permissions.check_read_all("Deno.symlink()")?;
     state.borrow::<FileSystemRc>().clone()
   };
 
@@ -868,8 +791,7 @@ where
 {
   let path = state
     .borrow_mut::<P>()
-    .check_read(&path, "Deno.readLink()")
-    .map_err(FsOpsError::Permission)?;
+    .check_read(&path, "Deno.readLink()")?;
 
   let fs = state.borrow::<FileSystemRc>();
 
@@ -891,8 +813,7 @@ where
     let mut state = state.borrow_mut();
     let path = state
       .borrow_mut::<P>()
-      .check_read(&path, "Deno.readLink()")
-      .map_err(FsOpsError::Permission)?;
+      .check_read(&path, "Deno.readLink()")?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
 
@@ -915,8 +836,7 @@ where
 {
   let path = state
     .borrow_mut::<P>()
-    .check_write(path, "Deno.truncateSync()")
-    .map_err(FsOpsError::Permission)?;
+    .check_write(path, "Deno.truncateSync()")?;
 
   let fs = state.borrow::<FileSystemRc>();
   fs.truncate_sync(&path, len)
@@ -938,8 +858,7 @@ where
     let mut state = state.borrow_mut();
     let path = state
       .borrow_mut::<P>()
-      .check_write(&path, "Deno.truncate()")
-      .map_err(FsOpsError::Permission)?;
+      .check_write(&path, "Deno.truncate()")?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
 
@@ -962,10 +881,7 @@ pub fn op_fs_utime_sync<P>(
 where
   P: FsPermissions + 'static,
 {
-  let path = state
-    .borrow_mut::<P>()
-    .check_write(path, "Deno.utime()")
-    .map_err(FsOpsError::Permission)?;
+  let path = state.borrow_mut::<P>().check_write(path, "Deno.utime()")?;
 
   let fs = state.borrow::<FileSystemRc>();
   fs.utime_sync(&path, atime_secs, atime_nanos, mtime_secs, mtime_nanos)
@@ -988,10 +904,7 @@ where
 {
   let (fs, path) = {
     let mut state = state.borrow_mut();
-    let path = state
-      .borrow_mut::<P>()
-      .check_write(&path, "Deno.utime()")
-      .map_err(FsOpsError::Permission)?;
+    let path = state.borrow_mut::<P>().check_write(&path, "Deno.utime()")?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
 
@@ -1219,16 +1132,12 @@ where
 {
   let fs = state.borrow::<FileSystemRc>().clone();
   let dir = match dir {
-    Some(dir) => state
-      .borrow_mut::<P>()
-      .check_write(dir, api_name)
-      .map_err(FsOpsError::Permission)?,
+    Some(dir) => state.borrow_mut::<P>().check_write(dir, api_name)?,
     None => {
       let dir = fs.tmp_dir().context("tmpdir")?;
       state
         .borrow_mut::<P>()
-        .check_write_blind(&dir, "TMP", api_name)
-        .map_err(FsOpsError::Permission)?;
+        .check_write_blind(&dir, "TMP", api_name)?;
       dir
     }
   };
@@ -1246,16 +1155,12 @@ where
   let mut state = state.borrow_mut();
   let fs = state.borrow::<FileSystemRc>().clone();
   let dir = match dir {
-    Some(dir) => state
-      .borrow_mut::<P>()
-      .check_write(dir, api_name)
-      .map_err(FsOpsError::Permission)?,
+    Some(dir) => state.borrow_mut::<P>().check_write(dir, api_name)?,
     None => {
       let dir = fs.tmp_dir().context("tmpdir")?;
       state
         .borrow_mut::<P>()
-        .check_write_blind(&dir, "TMP", api_name)
-        .map_err(FsOpsError::Permission)?;
+        .check_write_blind(&dir, "TMP", api_name)?;
       dir
     }
   };
diff --git a/ext/http/00_serve.ts b/ext/http/00_serve.ts
index 1b70cf2129..7bf83e49c3 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,
@@ -373,6 +374,18 @@ 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 {
diff --git a/ext/http/Cargo.toml b/ext/http/Cargo.toml
index 6fa7598cb5..ed98fe349c 100644
--- a/ext/http/Cargo.toml
+++ b/ext/http/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_http"
-version = "0.171.0"
+version = "0.175.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/http/http_next.rs b/ext/http/http_next.rs
index 56c46de925..1251f00cc0 100644
--- a/ext/http/http_next.rs
+++ b/ext/http/http_next.rs
@@ -564,6 +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,
     _ => (),
@@ -700,6 +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)]
diff --git a/ext/http/lib.rs b/ext/http/lib.rs
index 6243804a14..49893b1b92 100644
--- a/ext/http/lib.rs
+++ b/ext/http/lib.rs
@@ -112,7 +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>,
diff --git a/ext/http/service.rs b/ext/http/service.rs
index 75f93d77c2..ce24dea43f 100644
--- a/ext/http/service.rs
+++ b/ext/http/service.rs
@@ -27,6 +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>;
@@ -211,6 +212,7 @@ 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>,
@@ -276,6 +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,
@@ -312,6 +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,
@@ -390,6 +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).
diff --git a/ext/io/Cargo.toml b/ext/io/Cargo.toml
index 8f407c820c..6ef049ff9b 100644
--- a/ext/io/Cargo.toml
+++ b/ext/io/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_io"
-version = "0.83.0"
+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 b6fc70ca24..3492e2f441 100644
--- a/ext/io/bi_pipe.rs
+++ b/ext/io/bi_pipe.rs
@@ -183,9 +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 }))
 }
@@ -280,7 +281,7 @@ pub fn bi_pipe_pair_raw(
     // 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;
@@ -301,13 +302,13 @@ pub fn bi_pipe_pair_raw(
     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));
         }
@@ -323,13 +324,9 @@ pub fn bi_pipe_pair_raw(
         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];
diff --git a/ext/io/fs.rs b/ext/io/fs.rs
index 06fc3da098..8854265209 100644
--- a/ext/io/fs.rs
+++ b/ext/io/fs.rs
@@ -1,6 +1,7 @@
 // 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;
@@ -21,6 +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 {
@@ -55,20 +71,6 @@ impl From<io::ErrorKind> for FsError {
   }
 }
 
-impl From<FsError> for deno_core::error::AnyError {
-  fn from(err: FsError) -> Self {
-    match err {
-      FsError::Io(err) => err.into(),
-      FsError::FileBusy => deno_core::error::resource_unavailable(),
-      FsError::NotSupported => deno_core::error::not_supported(),
-      FsError::NotCapable(err) => deno_core::error::custom_error(
-        "NotCapable",
-        format!("permission denied: {err}"),
-      ),
-    }
-  }
-}
-
 impl From<JoinError> for FsError {
   fn from(err: JoinError) -> Self {
     if err.is_cancelled() {
diff --git a/ext/kv/Cargo.toml b/ext/kv/Cargo.toml
index f7b28af675..1d7b91770f 100644
--- a/ext/kv/Cargo.toml
+++ b/ext/kv/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_kv"
-version = "0.81.0"
+version = "0.85.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
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 0b4a3693c4..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::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 ef2e41d57e..df3ec0287b 100644
--- a/ext/napi/Cargo.toml
+++ b/ext/napi/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_napi"
-version = "0.104.0"
+version = "0.108.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -16,5 +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 100%
rename from cli/napi/generated_symbol_exports_list_linux.def
rename to ext/napi/generated_symbol_exports_list_linux.def
diff --git a/cli/napi/generated_symbol_exports_list_macos.def b/ext/napi/generated_symbol_exports_list_macos.def
similarity index 100%
rename from cli/napi/generated_symbol_exports_list_macos.def
rename to ext/napi/generated_symbol_exports_list_macos.def
diff --git a/cli/napi/generated_symbol_exports_list_windows.def b/ext/napi/generated_symbol_exports_list_windows.def
similarity index 100%
rename from cli/napi/generated_symbol_exports_list_windows.def
rename to ext/napi/generated_symbol_exports_list_windows.def
diff --git a/cli/napi/js_native_api.rs b/ext/napi/js_native_api.rs
similarity index 99%
rename from cli/napi/js_native_api.rs
rename to ext/napi/js_native_api.rs
index 35e7690c3c..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;
 
@@ -1083,7 +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,
@@ -1647,7 +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();
       }
diff --git a/ext/napi/lib.rs b/ext/napi/lib.rs
index 0b2b3eb5e7..88b8c238df 100644
--- a/ext/napi/lib.rs
+++ b/ext/napi/lib.rs
@@ -5,6 +5,22 @@
 #![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::op2;
 use deno_core::parking_lot::RwLock;
@@ -27,7 +43,7 @@ pub enum NApiError {
   #[error("Unable to find register Node-API module at {}", .0.display())]
   ModuleNotFound(PathBuf),
   #[error(transparent)]
-  Permission(deno_core::error::AnyError),
+  Permission(#[from] PermissionCheckError),
 }
 
 #[cfg(unix)]
@@ -39,6 +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;
@@ -492,20 +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,
-  ) -> Result<PathBuf, deno_core::error::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, deno_core::error::AnyError> {
+  fn check(&mut self, path: &str) -> Result<PathBuf, PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_ffi(self, path)
   }
 }
@@ -537,7 +548,7 @@ where
   let (async_work_sender, cleanup_hooks, external_ops_tracker, path) = {
     let mut op_state = op_state.borrow_mut();
     let permissions = op_state.borrow_mut::<NP>();
-    let path = permissions.check(&path).map_err(NApiError::Permission)?;
+    let path = permissions.check(&path)?;
     let napi_state = op_state.borrow::<NapiState>();
     (
       op_state.borrow::<V8CrossThreadTaskSpawner>().clone(),
@@ -631,3 +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 98%
rename from cli/napi/node_api.rs
rename to ext/napi/node_api.rs
index 4497a4695a..186ae42c48 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;
@@ -488,7 +488,7 @@ 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 +537,10 @@ 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);
 
@@ -560,7 +563,10 @@ fn napi_get_uv_event_loop(
 }
 
 #[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);
 
@@ -897,7 +903,7 @@ 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 7c9bf208c7..7c13a9165c 100644
--- a/cli/napi/sym/Cargo.toml
+++ b/ext/napi/sym/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "napi_sym"
-version = "0.103.0"
+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 100%
rename from cli/napi/sym/symbol_exports.json
rename to ext/napi/sym/symbol_exports.json
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/cli/napi/uv.rs b/ext/napi/uv.rs
similarity index 95%
rename from cli/napi/uv.rs
rename to ext/napi/uv.rs
index d4cb5c0b36..6f728a92b3 100644
--- a/cli/napi/uv.rs
+++ b/ext/napi/uv.rs
@@ -1,7 +1,7 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
+use crate::*;
 use deno_core::parking_lot::Mutex;
-use deno_runtime::deno_napi::*;
 use std::mem::MaybeUninit;
 use std::ptr::addr_of_mut;
 
@@ -16,10 +16,10 @@ fn assert_ok(res: c_int) -> c_int {
   res
 }
 
-use crate::napi::js_native_api::napi_create_string_utf8;
-use crate::napi::node_api::napi_create_async_work;
-use crate::napi::node_api::napi_delete_async_work;
-use crate::napi::node_api::napi_queue_async_work;
+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 = {
diff --git a/ext/net/Cargo.toml b/ext/net/Cargo.toml
index 634dd7dda4..245deedd2d 100644
--- a/ext/net/Cargo.toml
+++ b/ext/net/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_net"
-version = "0.165.0"
+version = "0.169.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -17,11 +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/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 0f92dead0c..9a8b70f0f6 100644
--- a/ext/net/ops.rs
+++ b/ext/net/ops.rs
@@ -18,6 +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;
@@ -33,16 +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::ResolveError;
-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")]
@@ -81,8 +81,8 @@ pub enum NetError {
   Io(#[from] std::io::Error),
   #[error("Another accept task is ongoing")]
   AcceptTaskOngoing,
-  #[error("{0}")]
-  Permission(deno_core::error::AnyError),
+  #[error(transparent)]
+  Permission(#[from] deno_permissions::PermissionCheckError),
   #[error("{0}")]
   Resource(deno_core::error::AnyError),
   #[error("No resolved address found")]
@@ -195,12 +195,10 @@ where
 {
   {
     let mut s = state.borrow_mut();
-    s.borrow_mut::<NP>()
-      .check_net(
-        &(&addr.hostname, Some(addr.port)),
-        "Deno.DatagramConn.send()",
-      )
-      .map_err(NetError::Permission)?;
+    s.borrow_mut::<NP>().check_net(
+      &(&addr.hostname, Some(addr.port)),
+      "Deno.DatagramConn.send()",
+    )?;
   }
   let addr = resolve_addr(&addr.hostname, addr.port)
     .await?
@@ -369,8 +367,7 @@ where
     let mut state_ = state.borrow_mut();
     state_
       .borrow_mut::<NP>()
-      .check_net(&(&addr.hostname, Some(addr.port)), "Deno.connect()")
-      .map_err(NetError::Permission)?;
+      .check_net(&(&addr.hostname, Some(addr.port)), "Deno.connect()")?;
   }
 
   let addr = resolve_addr(&addr.hostname, addr.port)
@@ -420,8 +417,7 @@ where
   }
   state
     .borrow_mut::<NP>()
-    .check_net(&(&addr.hostname, Some(addr.port)), "Deno.listen()")
-    .map_err(NetError::Permission)?;
+    .check_net(&(&addr.hostname, Some(addr.port)), "Deno.listen()")?;
   let addr = resolve_addr_sync(&addr.hostname, addr.port)?
     .next()
     .ok_or_else(|| NetError::NoResolvedAddress)?;
@@ -449,8 +445,7 @@ where
 {
   state
     .borrow_mut::<NP>()
-    .check_net(&(&addr.hostname, Some(addr.port)), "Deno.listenDatagram()")
-    .map_err(NetError::Permission)?;
+    .check_net(&(&addr.hostname, Some(addr.port)), "Deno.listenDatagram()")?;
   let addr = resolve_addr_sync(&addr.hostname, addr.port)?
     .next()
     .ok_or_else(|| NetError::NoResolvedAddress)?;
@@ -647,9 +642,7 @@ where
       let socker_addr = &ns.socket_addr;
       let ip = socker_addr.ip().to_string();
       let port = socker_addr.port();
-      perm
-        .check_net(&(ip, Some(port)), "Deno.resolveDns()")
-        .map_err(NetError::Permission)?;
+      perm.check_net(&(ip, Some(port)), "Deno.resolveDns()")?;
     }
   }
 
@@ -834,6 +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;
@@ -842,21 +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() {
@@ -1041,7 +1035,7 @@ mod tests {
       &mut self,
       _host: &(T, Option<u16>),
       _api_name: &str,
-    ) -> Result<(), deno_core::error::AnyError> {
+    ) -> Result<(), PermissionCheckError> {
       Ok(())
     }
 
@@ -1049,7 +1043,7 @@ mod tests {
       &mut self,
       p: &str,
       _api_name: &str,
-    ) -> Result<PathBuf, deno_core::error::AnyError> {
+    ) -> Result<PathBuf, PermissionCheckError> {
       Ok(PathBuf::from(p))
     }
 
@@ -1057,7 +1051,7 @@ mod tests {
       &mut self,
       p: &str,
       _api_name: &str,
-    ) -> Result<PathBuf, deno_core::error::AnyError> {
+    ) -> Result<PathBuf, PermissionCheckError> {
       Ok(PathBuf::from(p))
     }
 
@@ -1065,7 +1059,7 @@ mod tests {
       &mut self,
       p: &'a Path,
       _api_name: &str,
-    ) -> Result<Cow<'a, Path>, deno_core::error::AnyError> {
+    ) -> Result<Cow<'a, Path>, PermissionCheckError> {
       Ok(Cow::Borrowed(p))
     }
   }
diff --git a/ext/node/Cargo.toml b/ext/node/Cargo.toml
index 55d53d0ce0..9e1a3495b5 100644
--- a/ext/node/Cargo.toml
+++ b/ext/node/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_node"
-version = "0.110.0"
+version = "0.114.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/node/lib.rs b/ext/node/lib.rs
index 9b22add453..9ca21e9941 100644
--- a/ext/node/lib.rs
+++ b/ext/node/lib.rs
@@ -9,25 +9,22 @@ 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 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 +46,18 @@ 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"]
@@ -60,20 +65,24 @@ 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>;
+  ) -> Result<Cow<'a, Path>, PermissionCheckError>;
   fn query_read_all(&mut self) -> bool;
-  fn check_sys(&mut self, kind: &str, api_name: &str) -> Result<(), AnyError>;
+  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 {
@@ -82,16 +91,24 @@ 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,
     )
@@ -100,7 +117,7 @@ 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)
   }
 
@@ -113,28 +130,33 @@ impl NodePermissions for deno_permissions::PermissionsContainer {
     &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 {
+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: &'a Path,
   ) -> Result<Cow<'a, Path>, AnyError>;
+
+  fn load_text_file_lossy(&self, path: &Path) -> Result<String, AnyError>;
 }
 
 pub static NODE_ENV_VAR_ALLOWLIST: Lazy<HashSet<String>> = Lazy::new(|| {
@@ -152,10 +174,12 @@ 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 pkg_json_resolver: PackageJsonResolverRc,
 }
 
 deno_core::extension!(deno_node,
@@ -348,7 +372,7 @@ 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>,
@@ -387,6 +411,15 @@ 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 = [
@@ -595,8 +628,8 @@ 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",
@@ -639,9 +672,10 @@ 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,
@@ -761,33 +795,16 @@ 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/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 ac62f5ccae..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 {
@@ -2025,7 +2268,7 @@ pub fn op_node_export_public_key_pem(
   };
 
   let pem_len = der::pem::encapsulated_len(label, LineEnding::LF, data.len())
-    .map_err(|_| type_error("very large data"))?;
+    .map_err(|_| ExportPublicKeyPemError::VeryLargeData)?;
   let mut out = vec![0; pem_len];
   let mut writer = PemWriter::new(label, LineEnding::LF, &mut out)?;
   writer.write(&data)?;
@@ -2040,22 +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 {
@@ -2066,7 +2319,7 @@ pub fn op_node_export_private_key_pem(
   };
 
   let pem_len = der::pem::encapsulated_len(label, LineEnding::LF, data.len())
-    .map_err(|_| type_error("very large data"))?;
+    .map_err(|_| ExportPrivateKeyPemError::VeryLargeData)?;
   let mut out = vec![0; pem_len];
   let mut writer = PemWriter::new(label, LineEnding::LF, &mut out)?;
   writer.write(&data)?;
@@ -2081,10 +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)
 }
 
@@ -2102,7 +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 730e1e482b..69571078fe 100644
--- a/ext/node/ops/http.rs
+++ b/ext/node/ops/http.rs
@@ -78,9 +78,7 @@ where
 
   {
     let permissions = state.borrow_mut::<P>();
-    permissions
-      .check_net_url(&url, "ClientRequest")
-      .map_err(FetchError::Permission)?;
+    permissions.check_net_url(&url, "ClientRequest")?;
   }
 
   let mut header_map = HeaderMap::new();
diff --git a/ext/node/ops/http2.rs b/ext/node/ops/http2.rs
index 705a8ecdcb..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;
 
@@ -478,11 +502,12 @@ 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 {
@@ -525,7 +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 7d85ee8532..30db8b6293 100644
--- a/ext/node/ops/require.rs
+++ b/ext/node/ops/require.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::generic_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::url::Url;
 use deno_core::v8;
@@ -12,6 +9,7 @@ use deno_core::OpState;
 use deno_fs::FileSystemRc;
 use deno_package_json::PackageJsonRc;
 use deno_path_util::normalize_path;
+use deno_path_util::url_to_file_path;
 use node_resolver::NodeModuleKind;
 use node_resolver::NodeResolutionMode;
 use node_resolver::REQUIRE_CONDITIONS;
@@ -22,21 +20,52 @@ 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::PackageJsonResolverRc;
 
 #[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: &'a Path,
-) -> Result<Cow<'a, Path>, AnyError>
+) -> 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]
@@ -95,7 +124,7 @@ 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,
 {
@@ -104,13 +133,10 @@ 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_path_util::normalize_path(current_dir.join(from))
+    let current_dir = &fs.cwd().map_err(RequireError::UnableToGetCwd)?;
+    normalize_path(current_dir.join(from))
   };
 
-  let 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();
@@ -131,7 +157,7 @@ where
   }
 
   let mut paths = Vec::with_capacity(from.components().count());
-  let mut current_path = from.as_ref();
+  let mut current_path = from.as_path();
   let mut maybe_parent = Some(current_path);
   while let Some(parent) = maybe_parent {
     if !parent.ends_with("node_modules") {
@@ -209,8 +235,11 @@ 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]
@@ -264,7 +293,7 @@ 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,
 {
@@ -287,12 +316,13 @@ 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);
-  let path = 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_path_util::strip_unc_prefix(fs.realpath_sync(&path)?);
@@ -319,12 +349,14 @@ 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",
+    ))
   }
 }
 
@@ -332,12 +364,14 @@ 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",
+    ))
   }
 }
 
@@ -348,7 +382,7 @@ 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,
 {
@@ -378,7 +412,7 @@ 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,
 {
@@ -386,8 +420,8 @@ 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();
@@ -416,6 +450,7 @@ 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,
@@ -440,14 +475,18 @@ 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);
-  let 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]
@@ -472,16 +511,17 @@ 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
@@ -495,7 +535,7 @@ 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);
   };
@@ -503,12 +543,16 @@ 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,
@@ -525,16 +569,14 @@ where
 pub fn op_require_read_closest_package_json<P>(
   state: &mut OpState,
   #[string] filename: String,
-) -> Result<Option<PackageJsonRc>, AnyError>
+) -> Result<Option<PackageJsonRc>, node_resolver::errors::ClosestPkgJsonError>
 where
   P: NodePermissions + 'static,
 {
   let filename = PathBuf::from(filename);
   // permissions: allow reading the closest package.json files
-  let node_resolver = state.borrow::<NodeResolverRc>().clone();
-  node_resolver
-    .get_closest_package_json_from_path(&filename)
-    .map_err(AnyError::from)
+  let pkg_json_resolver = state.borrow::<PackageJsonResolverRc>();
+  pkg_json_resolver.get_closest_package_json_from_path(&filename)
 }
 
 #[op2]
@@ -546,13 +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()
@@ -564,22 +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);
-  let referrer_path = 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),
@@ -604,20 +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 e9dbadb6f7..cb053774ef 100644
--- a/ext/node/ops/winerror.rs
+++ b/ext/node/ops/winerror.rs
@@ -62,7 +62,7 @@ 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",
diff --git a/ext/node/ops/worker_threads.rs b/ext/node/ops/worker_threads.rs
index 5f139c5dc8..d2e5758826 100644
--- a/ext/node/ops/worker_threads.rs
+++ b/ext/node/ops/worker_threads.rs
@@ -1,39 +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;
 
 #[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: &'a Path,
-) -> Result<Cow<'a, Path>, AnyError>
+) -> 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,
 {
@@ -45,44 +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);
     }
-    let path = 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_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)))?;
-  let url_path = 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..e75ef050d2 100644
--- a/ext/node/ops/zlib/mod.rs
+++ b/ext/node/ops/zlib/mod.rs
@@ -1,6 +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 std::borrow::Cow;
 use std::cell::RefCell;
@@ -8,7 +7,7 @@ use zlib::*;
 
 mod alloc;
 pub mod brotli;
-mod mode;
+pub mod mode;
 mod stream;
 
 use mode::Flush;
@@ -17,11 +16,11 @@ 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 +55,7 @@ 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 +64,11 @@ 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 +80,10 @@ 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 +129,7 @@ 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 +183,7 @@ 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 +201,7 @@ 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 +210,7 @@ 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 +224,8 @@ 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 +243,7 @@ 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 +256,20 @@ 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 +290,9 @@ 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 +313,9 @@ 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 +352,11 @@ 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 +364,10 @@ 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
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..d818bb5727 100644
--- a/ext/node/polyfills/01_require.js
+++ b/ext/node/polyfills/01_require.js
@@ -523,17 +523,13 @@ function resolveExports(
     return;
   }
 
-  if (!parentPath) {
-    return false;
-  }
-
   return op_require_resolve_exports(
     usesLocalNodeModulesDir,
     modulesPath,
     request,
     name,
     expansion,
-    parentPath,
+    parentPath ?? "",
   ) ?? false;
 }
 
@@ -1075,13 +1071,35 @@ Module._extensions[".js"] = function (module, filename) {
     } else if (pkg?.type === "commonjs") {
       format = "commonjs";
     }
-  } else if (StringPrototypeEndsWith(filename, ".cjs")) {
-    format = "commonjs";
   }
 
   module._compile(content, filename, format);
 };
 
+Module._extensions[".ts"] =
+  Module._extensions[".jsx"] =
+  Module._extensions[".tsx"] =
+    function (module, filename) {
+      const content = op_require_read_file(filename);
+
+      let format;
+      const pkg = op_require_read_closest_package_json(filename);
+      if (pkg?.type === "module") {
+        format = "module";
+      } else if (pkg?.type === "commonjs") {
+        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(
     url.pathToFileURL(filename).toString(),
@@ -1091,7 +1109,10 @@ 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);
 };
 
@@ -1291,6 +1312,8 @@ export function findSourceMap(_path) {
   return undefined;
 }
 
+Module.findSourceMap = findSourceMap;
+
 /**
  * @param {string | URL} _specifier
  * @param {string | URL} _parentUrl
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_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_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_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..d00c81ffb6 100644
--- a/ext/node/polyfills/_fs/_fs_stat.ts
+++ b/ext/node/polyfills/_fs/_fs_stat.ts
@@ -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 62470c564e..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())
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/_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/http.ts b/ext/node/polyfills/http.ts
index 20bef30099..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,
@@ -50,7 +51,6 @@ import { urlToHttpOptions } from "ext:deno_node/internal/url.ts";
 import { kEmptyObject } from "ext:deno_node/internal/util.mjs";
 import { constants, TCP } from "ext:deno_node/internal_binding/tcp_wrap.ts";
 import { notImplemented, warnNotImplemented } from "ext:deno_node/_utils.ts";
-import { isWindows } from "ext:deno_node/_util/os.ts";
 import {
   connResetException,
   ERR_HTTP_HEADERS_SENT,
@@ -70,6 +70,7 @@ import { resourceForReadableStream } from "ext:deno_web/06_streams.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, StringPrototypeToLowerCase } = primordials;
@@ -1184,49 +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,
@@ -1235,16 +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) => {
@@ -1260,193 +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[StringPrototypeToLowerCase(name)] = value;
-    return this;
-  }
+  this._readable = readable;
+  this._resolve = resolve;
+  this.socket = socket;
 
-  appendHeader(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;
+  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[key])) {
-        this.#headers[key] = [this.#headers[key]];
+      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[key];
-      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[StringPrototypeToLowerCase(name)];
-  }
-  removeHeader(name: string) {
-    delete this.#headers[StringPrototypeToLowerCase(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 {
@@ -1588,8 +1711,9 @@ export class ServerImpl extends EventEmitter {
       port = options.port | 0;
     }
 
-    // Use 0.0.0.0 for Windows, and [::] for other platforms.
-    let hostname = options.host ?? (isWindows ? "0.0.0.0" : "[::]");
+    // TODO(bnoordhuis) Node prefers [::] when host is omitted,
+    // we on the other hand default to 0.0.0.0.
+    let hostname = options.host ?? "0.0.0.0";
     if (hostname == "localhost") {
       hostname = "127.0.0.1";
     }
@@ -1678,6 +1802,8 @@ export class ServerImpl extends EventEmitter {
       this.#server.ref();
     }
     this.#unref = false;
+
+    return this;
   }
 
   unref() {
@@ -1685,6 +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/https.ts b/ext/node/polyfills/https.ts
index dd24cf048c..f60c5e471a 100644
--- a/ext/node/polyfills/https.ts
+++ b/ext/node/polyfills/https.ts
@@ -1,6 +1,9 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 // Copyright Joyent and Node contributors. All rights reserved. MIT license.
 
+// TODO(petamoriken): enable prefer-primordials for node polyfills
+// deno-lint-ignore-file prefer-primordials
+
 import { notImplemented } from "ext:deno_node/_utils.ts";
 import { urlToHttpOptions } from "ext:deno_node/internal/url.ts";
 import {
@@ -14,14 +17,6 @@ import { type ServerHandler, ServerImpl as HttpServer } from "node:http";
 import { validateObject } from "ext:deno_node/internal/validators.mjs";
 import { kEmptyObject } from "ext:deno_node/internal/util.mjs";
 import { Buffer } from "node:buffer";
-import { primordials } from "ext:core/mod.js";
-const {
-  ArrayPrototypeShift,
-  ArrayPrototypeUnshift,
-  ArrayIsArray,
-  ObjectPrototypeIsPrototypeOf,
-  ObjectAssign,
-} = primordials;
 
 export class Server extends HttpServer {
   constructor(opts, requestListener?: ServerHandler) {
@@ -34,11 +29,11 @@ export class Server extends HttpServer {
       validateObject(opts, "options");
     }
 
-    if (opts.cert && ArrayIsArray(opts.cert)) {
+    if (opts.cert && Array.isArray(opts.cert)) {
       notImplemented("https.Server.opts.cert array type");
     }
 
-    if (opts.key && ArrayIsArray(opts.key)) {
+    if (opts.key && Array.isArray(opts.key)) {
       notImplemented("https.Server.opts.key array type");
     }
 
@@ -47,12 +42,10 @@ export class Server extends HttpServer {
 
   _additionalServeOptions() {
     return {
-      cert: ObjectPrototypeIsPrototypeOf(Buffer, this._opts.cert)
-        // deno-lint-ignore prefer-primordials
+      cert: this._opts.cert instanceof Buffer
         ? this._opts.cert.toString()
         : this._opts.cert,
-      key: ObjectPrototypeIsPrototypeOf(Buffer, this._opts.key)
-        // deno-lint-ignore prefer-primordials
+      key: this._opts.key instanceof Buffer
         ? this._opts.key.toString()
         : this._opts.key,
     };
@@ -166,18 +159,18 @@ export function request(...args: any[]) {
   let options = {};
 
   if (typeof args[0] === "string") {
-    const urlStr = ArrayPrototypeShift(args);
+    const urlStr = args.shift();
     options = urlToHttpOptions(new URL(urlStr));
-  } else if (ObjectPrototypeIsPrototypeOf(URL, args[0])) {
-    options = urlToHttpOptions(ArrayPrototypeShift(args));
+  } else if (args[0] instanceof URL) {
+    options = urlToHttpOptions(args.shift());
   }
 
   if (args[0] && typeof args[0] !== "function") {
-    ObjectAssign(options, ArrayPrototypeShift(args));
+    Object.assign(options, args.shift());
   }
 
   options._defaultAgent = globalAgent;
-  ArrayPrototypeUnshift(args, options);
+  args.unshift(options);
 
   return new HttpsClientRequest(args[0], args[1]);
 }
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/child_process.ts b/ext/node/polyfills/internal/child_process.ts
index 65d825fd25..cfff1079ff 100644
--- a/ext/node/polyfills/internal/child_process.ts
+++ b/ext/node/polyfills/internal/child_process.ts
@@ -1339,7 +1339,7 @@ export function setupChannel(target: any, ipc: number) {
           }
         }
 
-        process.nextTick(handleMessage, msg);
+        nextTick(handleMessage, msg);
       }
     } catch (err) {
       if (
@@ -1400,7 +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));
       }
@@ -1416,7 +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];
@@ -1433,7 +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/dns/utils.ts b/ext/node/polyfills/internal/dns/utils.ts
index 1e0c3d9ed6..226fce93dd 100644
--- a/ext/node/polyfills/internal/dns/utils.ts
+++ b/ext/node/polyfills/internal/dns/utils.ts
@@ -416,10 +416,20 @@ export function emitInvalidHostnameWarning(hostname: string) {
   );
 }
 
-let dnsOrder = getOptionValue("--dns-result-order") || "verbatim";
+let dnsOrder = getOptionValue("--dns-result-order") || "ipv4first";
 
 export function getDefaultVerbatim() {
-  return dnsOrder !== "ipv4first";
+  switch (dnsOrder) {
+    case "verbatim": {
+      return true;
+    }
+    case "ipv4first": {
+      return false;
+    }
+    default: {
+      return false;
+    }
+  }
 }
 
 /**
diff --git a/ext/node/polyfills/internal/errors.ts b/ext/node/polyfills/internal/errors.ts
index 51bd7a0250..5a3d4437a1 100644
--- a/ext/node/polyfills/internal/errors.ts
+++ b/ext/node/polyfills/internal/errors.ts
@@ -2558,19 +2558,6 @@ 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(
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/cares_wrap.ts b/ext/node/polyfills/internal_binding/cares_wrap.ts
index cbfea40b22..6feb7faf0d 100644
--- a/ext/node/polyfills/internal_binding/cares_wrap.ts
+++ b/ext/node/polyfills/internal_binding/cares_wrap.ts
@@ -75,18 +75,11 @@ export function getaddrinfo(
 
   const recordTypes: ("A" | "AAAA")[] = [];
 
-  if (family === 6) {
+  if (family === 0 || family === 4) {
+    recordTypes.push("A");
+  }
+  if (family === 0 || family === 6) {
     recordTypes.push("AAAA");
-  } else if (family === 4) {
-    recordTypes.push("A");
-  } else if (family === 0 && hostname === "localhost") {
-    // Ipv6 is preferred over Ipv4 for localhost
-    recordTypes.push("AAAA");
-    recordTypes.push("A");
-  } else if (family === 0) {
-    // Only get Ipv4 addresses for the other hostnames
-    // This simulates what `getaddrinfo` does when the family is not specified
-    recordTypes.push("A");
   }
 
   (async () => {
diff --git a/ext/node/polyfills/internal_binding/http_parser.ts b/ext/node/polyfills/internal_binding/http_parser.ts
index ca4f896e20..bad10d9851 100644
--- a/ext/node/polyfills/internal_binding/http_parser.ts
+++ b/ext/node/polyfills/internal_binding/http_parser.ts
@@ -126,6 +126,7 @@ 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,
diff --git a/ext/node/polyfills/net.ts b/ext/node/polyfills/net.ts
index 35d273be93..48e1d0de87 100644
--- a/ext/node/polyfills/net.ts
+++ b/ext/node/polyfills/net.ts
@@ -1871,13 +1871,23 @@ function _setupListenHandle(
 
     // Try to bind to the unspecified IPv6 address, see if IPv6 is available
     if (!address && typeof fd !== "number") {
-      if (isWindows) {
-        address = DEFAULT_IPV4_ADDR;
-        addressType = 4;
-      } else {
-        address = DEFAULT_IPV6_ADDR;
-        addressType = 6;
-      }
+      // TODO(@bartlomieju): differs from Node which tries to bind to IPv6 first
+      // when no address is provided.
+      //
+      // Forcing IPv4 as a workaround for Deno not aligning with Node on
+      // implicit binding on Windows.
+      //
+      // REF: https://github.com/denoland/deno/issues/10762
+      // rval = _createServerHandle(DEFAULT_IPV6_ADDR, port, 6, fd, flags);
+
+      // if (typeof rval === "number") {
+      //   rval = null;
+      address = DEFAULT_IPV4_ADDR;
+      addressType = 4;
+      // } else {
+      //   address = DEFAULT_IPV6_ADDR;
+      //   addressType = 6;
+      // }
     }
 
     if (rval === null) {
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/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/tls/Cargo.toml b/ext/tls/Cargo.toml
index b060f28298..943fc8413e 100644
--- a/ext/tls/Cargo.toml
+++ b/ext/tls/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_tls"
-version = "0.160.0"
+version = "0.164.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/url/Cargo.toml b/ext/url/Cargo.toml
index ceef18f45a..557a4669e6 100644
--- a/ext/url/Cargo.toml
+++ b/ext/url/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_url"
-version = "0.173.0"
+version = "0.177.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
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/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 395ea182f9..db28d0e578 100644
--- a/ext/web/Cargo.toml
+++ b/ext/web/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_web"
-version = "0.204.0"
+version = "0.208.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/web/lib.rs b/ext/web/lib.rs
index 4935af5bd3..af0fc2c276 100644
--- a/ext/web/lib.rs
+++ b/ext/web/lib.rs
@@ -52,7 +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,
@@ -84,6 +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,
@@ -123,7 +125,7 @@ deno_core::extension!(deno_web,
     if let Some(location) = options.maybe_location {
       state.put(Location(location));
     }
-    state.put(StartTime::now());
+    state.put(StartTime::default());
   }
 );
 
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 7354919d4a..f23bb8371e 100644
--- a/ext/webgpu/Cargo.toml
+++ b/ext/webgpu/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_webgpu"
-version = "0.140.0"
+version = "0.144.0"
 authors = ["the Deno authors"]
 edition.workspace = true
 license = "MIT"
diff --git a/ext/webidl/Cargo.toml b/ext/webidl/Cargo.toml
index d069b32125..8c3f6f6128 100644
--- a/ext/webidl/Cargo.toml
+++ b/ext/webidl/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_webidl"
-version = "0.173.0"
+version = "0.177.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/websocket/Cargo.toml b/ext/websocket/Cargo.toml
index ec359100d4..61f1f5959c 100644
--- a/ext/websocket/Cargo.toml
+++ b/ext/websocket/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_websocket"
-version = "0.178.0"
+version = "0.182.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/websocket/lib.rs b/ext/websocket/lib.rs
index 2a67ac5a17..a5734271cf 100644
--- a/ext/websocket/lib.rs
+++ b/ext/websocket/lib.rs
@@ -50,6 +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;
@@ -75,7 +76,7 @@ pub enum WebsocketError {
   #[error(transparent)]
   Url(url::ParseError),
   #[error(transparent)]
-  Permission(deno_core::error::AnyError),
+  Permission(#[from] PermissionCheckError),
   #[error(transparent)]
   Resource(deno_core::error::AnyError),
   #[error(transparent)]
@@ -112,7 +113,7 @@ pub trait WebSocketPermissions {
     &mut self,
     _url: &url::Url,
     _api_name: &str,
-  ) -> Result<(), deno_core::error::AnyError>;
+  ) -> Result<(), PermissionCheckError>;
 }
 
 impl WebSocketPermissions for deno_permissions::PermissionsContainer {
@@ -121,7 +122,7 @@ impl WebSocketPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     url: &url::Url,
     api_name: &str,
-  ) -> Result<(), deno_core::error::AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     deno_permissions::PermissionsContainer::check_net_url(self, url, api_name)
   }
 }
@@ -158,13 +159,10 @@ pub fn op_ws_check_permission_and_cancel_handle<WP>(
 where
   WP: WebSocketPermissions + 'static,
 {
-  state
-    .borrow_mut::<WP>()
-    .check_net_url(
-      &url::Url::parse(&url).map_err(WebsocketError::Url)?,
-      &api_name,
-    )
-    .map_err(WebsocketError::Permission)?;
+  state.borrow_mut::<WP>().check_net_url(
+    &url::Url::parse(&url).map_err(WebsocketError::Url)?,
+    &api_name,
+  )?;
 
   if cancel_handle {
     let rid = state
diff --git a/ext/webstorage/Cargo.toml b/ext/webstorage/Cargo.toml
index 0d6fcd6a0d..01e23ab839 100644
--- a/ext/webstorage/Cargo.toml
+++ b/ext/webstorage/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_webstorage"
-version = "0.168.0"
+version = "0.172.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/resolvers/deno/Cargo.toml b/resolvers/deno/Cargo.toml
index e75a9a1014..24d50587b3 100644
--- a/resolvers/deno/Cargo.toml
+++ b/resolvers/deno/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_resolver"
-version = "0.5.0"
+version = "0.9.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/resolvers/deno/fs.rs b/resolvers/deno/fs.rs
index b08be37982..44495fa7c2 100644
--- a/resolvers/deno/fs.rs
+++ b/resolvers/deno/fs.rs
@@ -15,13 +15,3 @@ pub trait DenoResolverFs {
   fn is_dir_sync(&self, path: &Path) -> bool;
   fn read_dir_sync(&self, dir_path: &Path) -> std::io::Result<Vec<DirEntry>>;
 }
-
-pub(crate) struct DenoPkgJsonFsAdapter<'a, Fs: DenoResolverFs>(pub &'a Fs);
-
-impl<'a, Fs: DenoResolverFs> deno_package_json::fs::DenoPkgJsonFs
-  for DenoPkgJsonFsAdapter<'a, Fs>
-{
-  fn read_to_string_lossy(&self, path: &Path) -> std::io::Result<String> {
-    self.0.read_to_string_lossy(path)
-  }
-}
diff --git a/resolvers/deno/npm/byonm.rs b/resolvers/deno/npm/byonm.rs
index 3394b3e501..b85117052c 100644
--- a/resolvers/deno/npm/byonm.rs
+++ b/resolvers/deno/npm/byonm.rs
@@ -10,16 +10,17 @@ 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::load_pkg_json;
+use node_resolver::InNpmPackageChecker;
 use node_resolver::NpmResolver;
+use node_resolver::PackageJsonResolverRc;
 use thiserror::Error;
 use url::Url;
 
-use crate::fs::DenoPkgJsonFsAdapter;
 use crate::fs::DenoResolverFs;
 
 use super::local::normalize_pkg_name_for_node_modules_deno_folder;
@@ -36,32 +37,41 @@ pub enum ByonmResolvePkgFolderFromDenoReqError {
   Io(#[from] std::io::Error),
 }
 
-pub struct ByonmNpmResolverCreateOptions<Fs: DenoResolverFs> {
-  pub fs: Fs,
+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> {
+pub struct ByonmNpmResolver<Fs: DenoResolverFs, TEnv: NodeResolverEnv> {
   fs: Fs,
+  pkg_json_resolver: PackageJsonResolverRc<TEnv>,
   root_node_modules_dir: Option<PathBuf>,
 }
 
-impl<Fs: DenoResolverFs + Clone> Clone for ByonmNpmResolver<Fs> {
+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> ByonmNpmResolver<Fs> {
-  pub fn new(options: ByonmNpmResolverCreateOptions<Fs>) -> Self {
+impl<Fs: DenoResolverFs, TEnv: NodeResolverEnv> ByonmNpmResolver<Fs, TEnv> {
+  pub fn new(options: ByonmNpmResolverCreateOptions<Fs, TEnv>) -> Self {
     Self {
-      fs: options.fs,
       root_node_modules_dir: options.root_node_modules_dir,
+      fs: options.fs,
+      pkg_json_resolver: options.pkg_json_resolver,
     }
   }
 
@@ -73,7 +83,7 @@ impl<Fs: DenoResolverFs> ByonmNpmResolver<Fs> {
     &self,
     path: &Path,
   ) -> Result<Option<Arc<PackageJson>>, PackageJsonLoadError> {
-    load_pkg_json(&DenoPkgJsonFsAdapter(&self.fs), path)
+    self.pkg_json_resolver.load_package_json(path)
   }
 
   /// Finds the ancestor package.json that contains the specified dependency.
@@ -290,8 +300,10 @@ impl<Fs: DenoResolverFs> ByonmNpmResolver<Fs> {
   }
 }
 
-impl<Fs: DenoResolverFs + Send + Sync + std::fmt::Debug> NpmResolver
-  for ByonmNpmResolver<Fs>
+impl<
+    Fs: DenoResolverFs + Send + Sync + std::fmt::Debug,
+    TEnv: NodeResolverEnv,
+  > NpmResolver for ByonmNpmResolver<Fs, TEnv>
 {
   fn resolve_package_folder_from_package(
     &self,
@@ -342,7 +354,12 @@ impl<Fs: DenoResolverFs + Send + Sync + std::fmt::Debug> NpmResolver
       .into()
     })
   }
+}
 
+#[derive(Debug)]
+pub struct ByonmInNpmPackageChecker;
+
+impl InNpmPackageChecker for ByonmInNpmPackageChecker {
   fn in_npm_package(&self, specifier: &Url) -> bool {
     specifier.scheme() == "file"
       && specifier
diff --git a/resolvers/deno/npm/mod.rs b/resolvers/deno/npm/mod.rs
index 9d885cad31..45e2341c78 100644
--- a/resolvers/deno/npm/mod.rs
+++ b/resolvers/deno/npm/mod.rs
@@ -3,6 +3,7 @@
 mod byonm;
 mod local;
 
+pub use byonm::ByonmInNpmPackageChecker;
 pub use byonm::ByonmNpmResolver;
 pub use byonm::ByonmNpmResolverCreateOptions;
 pub use byonm::ByonmResolvePkgFolderFromDenoReqError;
diff --git a/resolvers/deno/sloppy_imports.rs b/resolvers/deno/sloppy_imports.rs
index e215e87686..7aba5b771a 100644
--- a/resolvers/deno/sloppy_imports.rs
+++ b/resolvers/deno/sloppy_imports.rs
@@ -232,7 +232,7 @@ impl<Fs: SloppyImportResolverFs> SloppyImportsResolver<Fs> {
             | MediaType::Tsx
             | MediaType::Json
             | MediaType::Wasm
-            | MediaType::TsBuildInfo
+            | MediaType::Css
             | MediaType::SourceMap => {
               return None;
             }
diff --git a/resolvers/node/Cargo.toml b/resolvers/node/Cargo.toml
index 44549bec19..6c2407ad9f 100644
--- a/resolvers/node/Cargo.toml
+++ b/resolvers/node/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "node_resolver"
-version = "0.12.0"
+version = "0.16.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/resolvers/node/analyze.rs b/resolvers/node/analyze.rs
index 009296006a..c7415933d7 100644
--- a/resolvers/node/analyze.rs
+++ b/resolvers/node/analyze.rs
@@ -19,18 +19,19 @@ use anyhow::Error as AnyError;
 use url::Url;
 
 use crate::env::NodeResolverEnv;
-use crate::package_json::load_pkg_json;
+use crate::npm::InNpmPackageCheckerRc;
 use crate::resolution::NodeResolverRc;
 use crate::NodeModuleKind;
 use crate::NodeResolutionMode;
 use crate::NpmResolverRc;
+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),
 }
 
@@ -50,11 +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<
@@ -63,8 +64,10 @@ pub struct NodeCodeTranslator<
 > {
   cjs_code_analyzer: TCjsCodeAnalyzer,
   env: TNodeResolverEnv,
+  in_npm_pkg_checker: InNpmPackageCheckerRc,
   node_resolver: NodeResolverRc<TNodeResolverEnv>,
   npm_resolver: NpmResolverRc,
+  pkg_json_resolver: PackageJsonResolverRc<TNodeResolverEnv>,
 }
 
 impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
@@ -73,14 +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,
+    pkg_json_resolver: PackageJsonResolverRc<TNodeResolverEnv>,
   ) -> Self {
     Self {
       cjs_code_analyzer,
       env,
+      in_npm_pkg_checker,
       node_resolver,
       npm_resolver,
+      pkg_json_resolver,
     }
   }
 
@@ -90,11 +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
@@ -108,7 +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(),
     ];
@@ -135,7 +142,12 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
     }
 
     source.push(format!(
-      "const mod = require(\"{}\");",
+      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()
@@ -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>>;
@@ -329,8 +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(
@@ -356,8 +369,9 @@ 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(url_from_file_path(&d.join(main).clean())?));
@@ -382,7 +396,7 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
     // 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") {
diff --git a/resolvers/node/errors.rs b/resolvers/node/errors.rs
index 4ba829eda5..aacbecefb4 100644
--- a/resolvers/node/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/resolvers/node/lib.rs b/resolvers/node/lib.rs
index f03f770486..18b0a85363 100644
--- a/resolvers/node/lib.rs
+++ b/resolvers/node/lib.rs
@@ -13,9 +13,12 @@ mod resolution;
 mod sync;
 
 pub use deno_package_json::PackageJson;
+pub use npm::InNpmPackageChecker;
+pub use npm::InNpmPackageCheckerRc;
 pub use npm::NpmResolver;
 pub use npm::NpmResolverRc;
-pub use package_json::load_pkg_json;
+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;
diff --git a/resolvers/node/npm.rs b/resolvers/node/npm.rs
index 6b5f21db62..2132f0b545 100644
--- a/resolvers/node/npm.rs
+++ b/resolvers/node/npm.rs
@@ -22,7 +22,13 @@ pub trait NpmResolver: std::fmt::Debug + MaybeSend + MaybeSync {
     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 {
diff --git a/resolvers/node/package_json.rs b/resolvers/node/package_json.rs
index de750f1d7e..6967779e5d 100644
--- a/resolvers/node/package_json.rs
+++ b/resolvers/node/package_json.rs
@@ -2,15 +2,21 @@
 
 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;
 
-// use a thread local cache so that workers have their own distinct cache
+// todo(dsherret): this isn't exactly correct and we should change it to instead
+// be created per worker and passed down as a ctor arg to the pkg json resolver
 thread_local! {
   static CACHE: RefCell<HashMap<PathBuf, PackageJsonRc>> = RefCell::new(HashMap::new());
 }
@@ -33,21 +39,91 @@ impl deno_package_json::PackageJsonCache for PackageJsonThreadLocalCache {
   }
 }
 
-/// 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 =>
-    {
+#[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)
     }
-    Err(err) => Err(PackageJsonLoadError(err)),
+
+    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/resolution.rs b/resolvers/node/resolution.rs
index 811583a5ee..d44539e978 100644
--- a/resolvers/node/resolution.rs
+++ b/resolvers/node/resolution.rs
@@ -6,9 +6,6 @@ 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::strip_unc_prefix;
 use deno_path_util::url_from_file_path;
 use serde_json::Map;
 use serde_json::Value;
@@ -16,8 +13,6 @@ 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;
@@ -32,7 +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;
@@ -42,14 +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::npm::InNpmPackageCheckerRc;
 use crate::NpmResolverRc;
+use crate::PackageJsonResolverRc;
 use crate::PathClean;
 use deno_package_json::PackageJson;
 
@@ -73,16 +66,14 @@ 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 +83,6 @@ 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 +91,28 @@ pub type NodeResolverRc<TEnv> = crate::sync::MaybeArc<NodeResolver<TEnv>>;
 #[derive(Debug)]
 pub struct NodeResolver<TEnv: NodeResolverEnv> {
   env: TEnv,
+  in_npm_pkg_checker: InNpmPackageCheckerRc,
   npm_resolver: NpmResolverRc,
+  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_resolver: NpmResolverRc,
+    pkg_json_resolver: PackageJsonResolverRc<TEnv>,
+  ) -> Self {
+    Self {
+      env,
+      in_npm_pkg_checker,
+      npm_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 +133,7 @@ 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 +158,7 @@ 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));
       }
     }
 
@@ -212,7 +179,7 @@ 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 +203,7 @@ 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)))?;
@@ -332,7 +300,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     package_subpath: Option<&str>,
     maybe_referrer: Option<&Url>,
     mode: NodeResolutionMode,
-  ) -> Result<NodeResolution, ResolvePkgSubpathFromDenoModuleError> {
+  ) -> Result<Url, PackageSubpathResolveError> {
     let node_module_kind = NodeModuleKind::Esm;
     let package_subpath = package_subpath
       .map(|s| format!("./{s}"))
@@ -345,10 +313,9 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
       DEFAULT_CONDITIONS,
       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 +323,9 @@ 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 +350,11 @@ 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,
       });
@@ -396,37 +367,9 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
       })?;
     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.
@@ -1101,7 +1044,9 @@ 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 {
@@ -1216,7 +1161,10 @@ 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,
@@ -1337,70 +1285,6 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     }
   }
 
-  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(
-      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,
diff --git a/runtime/Cargo.toml b/runtime/Cargo.toml
index dcb6b1ade6..ba236de149 100644
--- a/runtime/Cargo.toml
+++ b/runtime/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_runtime"
-version = "0.182.0"
+version = "0.186.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -117,10 +117,12 @@ once_cell.workspace = true
 percent-encoding.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/errors.rs b/runtime/errors.rs
index 9fc84407a9..0c26e0e47a 100644
--- a/runtime/errors.rs
+++ b/runtime/errors.rs
@@ -9,6 +9,16 @@
 //!   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;
@@ -40,6 +50,12 @@ 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;
@@ -49,11 +65,60 @@ 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 {
@@ -436,7 +501,7 @@ fn get_napi_error_class(e: &NApiError) -> &'static str {
     NApiError::InvalidPath
     | NApiError::LibLoading(_)
     | NApiError::ModuleNotFound(_) => "TypeError",
-    NApiError::Permission(e) => get_error_class_name(e).unwrap_or("Error"),
+    NApiError::Permission(e) => get_permission_check_error_class(e),
   }
 }
 
@@ -514,7 +579,7 @@ fn get_ffi_repr_error_class(e: &ReprError) -> &'static str {
     ReprError::InvalidF32 => "TypeError",
     ReprError::InvalidF64 => "TypeError",
     ReprError::InvalidPointer => "TypeError",
-    ReprError::Permission(e) => get_error_class_name(e).unwrap_or("Error"),
+    ReprError::Permission(e) => get_permission_check_error_class(e),
   }
 }
 
@@ -522,7 +587,7 @@ fn get_ffi_dlfcn_error_class(e: &DlfcnError) -> &'static str {
   match e {
     DlfcnError::RegisterSymbol { .. } => "Error",
     DlfcnError::Dlopen(_) => "Error",
-    DlfcnError::Permission(e) => get_error_class_name(e).unwrap_or("Error"),
+    DlfcnError::Permission(e) => get_permission_check_error_class(e),
     DlfcnError::Other(e) => get_error_class_name(e).unwrap_or("Error"),
   }
 }
@@ -540,7 +605,7 @@ 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_error_class_name(e).unwrap_or("Error"),
+    CallbackError::Permission(e) => get_permission_check_error_class(e),
   }
 }
 
@@ -549,15 +614,16 @@ fn get_ffi_call_error_class(e: &CallError) -> &'static str {
     CallError::IR(_) => "TypeError",
     CallError::NonblockingCallFailure(_) => "Error",
     CallError::InvalidSymbol(_) => "TypeError",
-    CallError::Permission(e) => get_error_class_name(e).unwrap_or("Error"),
+    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(_) => todo!(),
+    WebStorageError::Sqlite(_) => "Error",
     WebStorageError::Io(e) => get_io_error_class(e),
     WebStorageError::StorageExceeded => "DOMExceptionQuotaExceededError",
   }
@@ -624,9 +690,8 @@ fn get_broadcast_channel_error(error: &BroadcastChannelError) -> &'static str {
 
 fn get_fetch_error(error: &FetchError) -> &'static str {
   match error {
-    FetchError::Resource(e) | FetchError::Permission(e) => {
-      get_error_class_name(e).unwrap_or("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",
@@ -660,9 +725,8 @@ fn get_http_client_create_error(error: &HttpClientCreateError) -> &'static str {
 
 fn get_websocket_error(error: &WebsocketError) -> &'static str {
   match error {
-    WebsocketError::Permission(e) | WebsocketError::Resource(e) => {
-      get_error_class_name(e).unwrap_or("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",
@@ -695,18 +759,14 @@ fn get_websocket_handshake_error(error: &HandshakeError) -> &'static str {
   }
 }
 
-fn get_fs_error(error: &FsOpsError) -> &'static str {
+fn get_fs_ops_error(error: &FsOpsError) -> &'static str {
   match error {
     FsOpsError::Io(e) => get_io_error_class(e),
-    FsOpsError::OperationError(e) => match &e.err {
-      FsError::Io(e) => get_io_error_class(e),
-      FsError::FileBusy => "Busy",
-      FsError::NotSupported => "NotSupported",
-      FsError::NotCapable(_) => "NotCapable",
-    },
-    FsOpsError::Permission(e)
-    | FsOpsError::Resource(e)
-    | FsOpsError::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+    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) => {
@@ -773,9 +833,10 @@ fn get_net_error(error: &NetError) -> &'static str {
     NetError::SocketBusy => "Busy",
     NetError::Io(e) => get_io_error_class(e),
     NetError::AcceptTaskOngoing => "Busy",
-    NetError::RootCertStore(e)
-    | NetError::Permission(e)
-    | NetError::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+    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),
@@ -806,6 +867,121 @@ fn get_net_map_error(error: &deno_net::io::MapError) -> &'static str {
   }
 }
 
+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) => {
@@ -859,10 +1035,712 @@ fn get_websocket_upgrade_error(error: &WebSocketUpgradeError) -> &'static str {
   }
 }
 
+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(|| {
+      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)
@@ -884,7 +1762,7 @@ pub fn get_error_class_name(e: &AnyError) -> Option<&'static str> {
       e.downcast_ref::<WebSocketUpgradeError>()
         .map(get_websocket_upgrade_error)
     })
-    .or_else(|| e.downcast_ref::<FsOpsError>().map(get_fs_error))
+    .or_else(|| e.downcast_ref::<FsOpsError>().map(get_fs_ops_error))
     .or_else(|| {
       e.downcast_ref::<DlfcnError>()
         .map(get_ffi_dlfcn_error_class)
diff --git a/runtime/fmt_errors.rs b/runtime/fmt_errors.rs
index 8476aab28c..4cd8a06345 100644
--- a/runtime/fmt_errors.rs
+++ b/runtime/fmt_errors.rs
@@ -1,12 +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)]
@@ -25,6 +23,7 @@ struct IndexedErrorReference<'a> {
 enum FixSuggestionKind {
   Info,
   Hint,
+  Docs,
 }
 
 #[derive(Debug)]
@@ -67,6 +66,13 @@ impl<'a> FixSuggestion<'a> {
       message: FixSuggestionMessage::Multiline(messages),
     }
   }
+
+  pub fn docs(url: &'a str) -> Self {
+    Self {
+      kind: FixSuggestionKind::Docs,
+      message: FixSuggestionMessage::Single(url),
+    }
+  }
 }
 
 struct AnsiColors;
@@ -79,10 +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(),
     }
   }
 }
@@ -115,7 +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,
     );
   }
 
@@ -128,9 +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);
@@ -201,7 +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();
     }
   }
 
@@ -239,7 +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![])
     };
@@ -256,12 +264,23 @@ 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()
+        }
       };
       match suggestion.message {
         FixSuggestionMessage::Single(msg) => {
-          write!(s, "{}", msg).unwrap();
+          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() {
@@ -300,7 +319,49 @@ fn get_suggestions_for_terminal_errors(e: &JsError) -> Vec<FixSuggestion> {
           cstr!("or add <u>package.json</> next to the file with <i>\"type\": \"commonjs\"</> option"),
           cstr!("and pass <i>--unstable-detect-cjs</> flag."),
         ]),
-        FixSuggestion::hint("See https://docs.deno.com/go/commonjs for details"),
+        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(cstr!("Import it explicitly with <u>import { Buffer } from \"node:buffer\";</>.")),
+      ];
+    } 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(cstr!("Import it explicitly with <u>import { clearImmediate } from \"node:timers\";</>.")),
+      ];
+    } 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(cstr!("Import it explicitly with <u>import { setImmediate } from \"node:timers\";</>.")),
+      ];
+    } 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(cstr!("Use <u>globalThis</> instead, or assign <u>globalThis.global = globalThis</>.")),
       ];
     } else if msg.contains("openKv is not a function") {
       return vec![
diff --git a/runtime/inspector_server.rs b/runtime/inspector_server.rs
index 33b2ab8727..a789dd3dca 100644
--- a/runtime/inspector_server.rs
+++ b/runtime/inspector_server.rs
@@ -19,11 +19,12 @@ 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;
 use fastwebsockets::OpCode;
-use fastwebsockets::Payload;
 use fastwebsockets::WebSocket;
 use hyper::body::Bytes;
 use hyper_util::rt::TokioIo;
@@ -34,7 +35,6 @@ use std::pin::pin;
 use std::process;
 use std::rc::Rc;
 use std::thread;
-use std::time::Duration;
 use tokio::net::TcpListener;
 use tokio::sync::broadcast;
 use uuid::Uuid;
@@ -194,6 +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.");
@@ -395,13 +400,8 @@ async fn pump_websocket_messages(
   inbound_tx: UnboundedSender<String>,
   mut outbound_rx: UnboundedReceiver<InspectorMsg>,
 ) {
-  let mut ticker = tokio::time::interval(Duration::from_secs(30));
-
   'pump: loop {
     tokio::select! {
-        _ = ticker.tick() => {
-            let _ = websocket.write_frame(Frame::new(true, OpCode::Ping, None, Payload::Borrowed(&[]))).await;
-        }
         Some(msg) = outbound_rx.next() => {
             let msg = Frame::text(msg.content.into_bytes().into());
             let _ = websocket.write_frame(msg).await;
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/99_main.js b/runtime/js/99_main.js
index 56a5b411bb..6ddaa1335e 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,
@@ -642,7 +641,7 @@ function bootstrapMainRuntime(runtimeOptions, warmup = false) {
 
     removeImportedOps();
 
-    performance.setTimeOrigin(DateNow());
+    performance.setTimeOrigin();
     globalThis_ = globalThis;
 
     // Remove bootstrapping data from the global scope
@@ -696,6 +695,7 @@ function bootstrapMainRuntime(runtimeOptions, warmup = false) {
     // are lost.
     let jupyterNs = undefined;
     ObjectDefineProperty(finalDenoNs, "jupyter", {
+      __proto__: null,
       get() {
         if (jupyterNs) {
           return jupyterNs;
@@ -857,7 +857,7 @@ function bootstrapWorkerRuntime(
       7: nodeDebug,
     } = runtimeOptions;
 
-    performance.setTimeOrigin(DateNow());
+    performance.setTimeOrigin();
     globalThis_ = globalThis;
 
     // Remove bootstrapping data from the global scope
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 cbabbe22c5..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)
@@ -30,7 +46,7 @@ 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()?;
@@ -45,7 +61,7 @@ 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()?;
@@ -61,7 +77,7 @@ 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()?;
@@ -73,5 +89,5 @@ fn op_http_start(
     ));
   }
 
-  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..67065b901b 100644
--- a/runtime/ops/mod.rs
+++ b/runtime/ops/mod.rs
@@ -9,7 +9,6 @@ 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 bd9260e97e..9bee9d8234 100644
--- a/runtime/ops/os/mod.rs
+++ b/runtime/ops/os/mod.rs
@@ -1,9 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use super::utils::into_string;
 use crate::worker::ExitCode;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::v8;
 use deno_core::OpState;
@@ -73,9 +70,27 @@ 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 +98,10 @@ 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 +109,16 @@ 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 +126,9 @@ 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 +138,7 @@ 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 +146,11 @@ 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 +164,10 @@ 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(())
@@ -178,7 +192,9 @@ fn op_exit(state: &mut OpState) {
 
 #[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 +203,9 @@ 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 +214,9 @@ 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 +227,7 @@ 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 +279,7 @@ 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 +289,9 @@ 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 +305,9 @@ 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 +317,9 @@ 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 +333,9 @@ 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 +513,7 @@ 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 +522,8 @@ 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/permissions.rs b/runtime/ops/permissions.rs
index 1dbc852596..9ad963f3bc 100644
--- a/runtime/ops/permissions.rs
+++ b/runtime/ops/permissions.rs
@@ -2,8 +2,6 @@
 
 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;
@@ -47,12 +45,26 @@ 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> {
+) -> Result<PermissionStatus, PermissionError> {
   let permissions = state.borrow::<PermissionsContainer>();
   let perm = match args.name.as_ref() {
     "read" => permissions.query_read(args.path.as_deref())?,
@@ -62,12 +74,7 @@ pub fn op_query_permission(
     "sys" => permissions.query_sys(args.kind.as_deref())?,
     "run" => permissions.query_run(args.command.as_deref())?,
     "ffi" => permissions.query_ffi(args.path.as_deref())?,
-    n => {
-      return Err(custom_error(
-        "ReferenceError",
-        format!("No such permission name: {n}"),
-      ))
-    }
+    _ => return Err(PermissionError::InvalidPermissionName(args.name)),
   };
   Ok(PermissionStatus::from(perm))
 }
@@ -77,7 +84,7 @@ pub fn op_query_permission(
 pub fn op_revoke_permission(
   state: &mut OpState,
   #[serde] args: PermissionArgs,
-) -> Result<PermissionStatus, AnyError> {
+) -> Result<PermissionStatus, PermissionError> {
   let permissions = state.borrow::<PermissionsContainer>();
   let perm = match args.name.as_ref() {
     "read" => permissions.revoke_read(args.path.as_deref())?,
@@ -87,12 +94,7 @@ pub fn op_revoke_permission(
     "sys" => permissions.revoke_sys(args.kind.as_deref())?,
     "run" => permissions.revoke_run(args.command.as_deref())?,
     "ffi" => permissions.revoke_ffi(args.path.as_deref())?,
-    n => {
-      return Err(custom_error(
-        "ReferenceError",
-        format!("No such permission name: {n}"),
-      ))
-    }
+    _ => return Err(PermissionError::InvalidPermissionName(args.name)),
   };
   Ok(PermissionStatus::from(perm))
 }
@@ -102,7 +104,7 @@ pub fn op_revoke_permission(
 pub fn op_request_permission(
   state: &mut OpState,
   #[serde] args: PermissionArgs,
-) -> Result<PermissionStatus, AnyError> {
+) -> Result<PermissionStatus, PermissionError> {
   let permissions = state.borrow::<PermissionsContainer>();
   let perm = match args.name.as_ref() {
     "read" => permissions.request_read(args.path.as_deref())?,
@@ -112,12 +114,7 @@ pub fn op_request_permission(
     "sys" => permissions.request_sys(args.kind.as_deref())?,
     "run" => permissions.request_run(args.command.as_deref())?,
     "ffi" => permissions.request_ffi(args.path.as_deref())?,
-    n => {
-      return Err(custom_error(
-        "ReferenceError",
-        format!("No such permission name: {n}"),
-      ))
-    }
+    _ => return Err(PermissionError::InvalidPermissionName(args.name)),
   };
   Ok(PermissionStatus::from(perm))
 }
diff --git a/runtime/ops/process.rs b/runtime/ops/process.rs
index f6555e9324..de3141f1f9 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();
@@ -683,7 +726,7 @@ 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)),
     }
   }
 }
@@ -692,12 +735,20 @@ fn resolve_path(path: &str, cwd: &Path) -> PathBuf {
   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(
   state: &mut OpState,
   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
@@ -705,14 +756,14 @@ 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(
+      return Err(CheckRunPermissionError::Other(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 { "" }
         )
-      ));
+      )));
     }
     permissions.check_run(cmd, api_name)?;
   }
@@ -754,7 +805,7 @@ 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 +822,23 @@ 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 +846,14 @@ 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 +876,15 @@ 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 +930,9 @@ 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 +1044,12 @@ 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 +1072,17 @@ 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 +1096,9 @@ 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 +1132,10 @@ 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 3bf43d6e15..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 {
@@ -153,18 +187,18 @@ macro_rules! first_literal {
   };
 }
 macro_rules! signal_dict {
-  ($error_msg:expr, $(($number:literal, $($name:literal)|+)),*) => {
-    pub fn signal_str_to_int(s: &str) -> Result<libc::c_int, AnyError> {
+  ($(($number:literal, $($name:literal)|+)),*) => {
+    pub fn signal_str_to_int(s: &str) -> Result<libc::c_int, SignalError> {
       match s {
         $($($name)|* => Ok($number),)*
-        _ => Err(type_error($error_msg(s))),
+        _ => Err(SignalError::InvalidSignalStr(s.to_string())),
       }
     }
 
-    pub fn signal_int_to_str(s: libc::c_int) -> Result<&'static str, AnyError> {
+    pub fn signal_int_to_str(s: libc::c_int) -> Result<&'static str, SignalError> {
       match s {
         $($number => Ok(first_literal!($($name),+)),)*
-        _ => Err(type_error($error_msg(s))),
+        _ => Err(SignalError::InvalidSignalInt(s)),
       }
     }
   }
@@ -172,7 +206,6 @@ macro_rules! signal_dict {
 
 #[cfg(target_os = "freebsd")]
 signal_dict!(
-  |s| { format!("Invalid signal : {}", s) },
   (1, "SIGHUP"),
   (2, "SIGINT"),
   (3, "SIGQUIT"),
@@ -210,7 +243,6 @@ signal_dict!(
 
 #[cfg(target_os = "openbsd")]
 signal_dict!(
-  |s| { format!("Invalid signal : {}", s) },
   (1, "SIGHUP"),
   (2, "SIGINT"),
   (3, "SIGQUIT"),
@@ -246,7 +278,6 @@ signal_dict!(
 
 #[cfg(any(target_os = "android", target_os = "linux"))]
 signal_dict!(
-  |s| { format!("Invalid signal : {s}") },
   (1, "SIGHUP"),
   (2, "SIGINT"),
   (3, "SIGQUIT"),
@@ -282,7 +313,6 @@ signal_dict!(
 
 #[cfg(target_os = "macos")]
 signal_dict!(
-  |s| { format!("Invalid signal : {s}") },
   (1, "SIGHUP"),
   (2, "SIGINT"),
   (3, "SIGQUIT"),
@@ -318,7 +348,6 @@ signal_dict!(
 
 #[cfg(any(target_os = "solaris", target_os = "illumos"))]
 signal_dict!(
-  |s| { format!("Invalid signal : {s}") },
   (1, "SIGHUP"),
   (2, "SIGINT"),
   (3, "SIGQUIT"),
@@ -362,11 +391,7 @@ signal_dict!(
 );
 
 #[cfg(target_os = "windows")]
-signal_dict!(
-  |_| { "Windows only supports ctrl-c (SIGINT) and ctrl-break (SIGBREAK)." },
-  (2, "SIGINT"),
-  (21, "SIGBREAK")
-);
+signal_dict!((2, "SIGINT"), (21, "SIGBREAK"));
 
 #[cfg(unix)]
 #[op2(fast)]
@@ -374,12 +399,10 @@ signal_dict!(
 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))?);
@@ -413,7 +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 {
@@ -437,7 +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
@@ -456,7 +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 77e1330b51..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(())
@@ -252,7 +267,8 @@ fn op_set_raw(
         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
         }
@@ -274,11 +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)?;
       }
     }
 
@@ -290,13 +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;
@@ -419,7 +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.");
 
@@ -439,6 +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 e28bf2192f..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()
@@ -50,7 +50,6 @@ async fn op_worker_recv_message(
     .recv(state.clone())
     .or_cancel(handle.cancel)
     .await?
-    .map_err(|e| e.into())
 }
 
 #[op2(fast)]
diff --git a/runtime/ops/web_worker/sync_fetch.rs b/runtime/ops/web_worker/sync_fetch.rs
index bd55a5fc8c..d1f133d3d2 100644
--- a/runtime/ops/web_worker/sync_fetch.rs
+++ b/runtime/ops/web_worker/sync_fetch.rs
@@ -4,14 +4,12 @@ use std::sync::Arc;
 
 use crate::web_worker::WebWorkerInternalHandle;
 use crate::web_worker::WebWorkerType;
-use deno_core::error::custom_error;
-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 http_body_util::BodyExt;
 use hyper::body::Bytes;
@@ -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".
@@ -107,30 +130,32 @@ 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);
 
@@ -139,10 +164,11 @@ pub fn op_worker_sync_fetch(
                 (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(),
+                  ),
+                )
               }
             };
 
@@ -151,17 +177,11 @@ pub fn op_worker_sync_fetch(
               match mime_type.as_deref() {
                 Some("application/javascript" | "text/javascript") => {}
                 Some(mime_type) => {
-                  return Err(custom_error(
-                    "DOMExceptionNetworkError",
-                    format!("Invalid MIME type {mime_type:?}."),
-                  ))
-                }
-                None => {
-                  return Err(custom_error(
-                    "DOMExceptionNetworkError",
-                    "Missing MIME type.",
+                  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 d85541d51d..521284a6a0 100644
--- a/runtime/ops/worker_host.rs
+++ b/runtime/ops/worker_host.rs
@@ -10,8 +10,6 @@ use crate::web_worker::WorkerControlEvent;
 use crate::web_worker::WorkerId;
 use crate::web_worker::WorkerMetadata;
 use crate::worker::FormatJsErrorFn;
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::serde::Deserialize;
 use deno_core::CancelFuture;
@@ -22,6 +20,7 @@ use deno_permissions::ChildPermissionsArg;
 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;
@@ -119,6 +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]
@@ -126,7 +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())
@@ -137,10 +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(custom_error(
-        "DOMExceptionNotSupportedError",
-        "Classic workers are not supported.",
-      ));
+      return Err(CreateWorkerError::ClassicWorkers);
     }
   }
 
@@ -154,7 +164,9 @@ fn op_create_worker(
   let parent_permissions = state.borrow_mut::<PermissionsContainer>();
   let worker_permissions = if let Some(child_permissions_arg) = args.permissions
   {
-    parent_permissions.create_child_permissions(child_permissions_arg)?
+    parent_permissions
+      .create_child_permissions(child_permissions_arg)
+      .map_err(CreateWorkerError::Permission)?
   } else {
     parent_permissions.clone()
   };
@@ -166,9 +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}"));
@@ -202,7 +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
@@ -218,7 +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(),
@@ -291,7 +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>();
@@ -300,7 +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;
     }
   };
 
@@ -309,22 +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
     }
   }
 }
@@ -334,7 +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>();
@@ -359,7 +369,7 @@ async fn op_host_recv_message(
       }
       Ok(ret)
     }
-    Ok(Err(err)) => Err(err.into()),
+    Ok(Err(err)) => Err(err),
     Err(_) => {
       // The worker was terminated.
       Ok(None)
@@ -373,7 +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 fa62227e0d..e8460e03f8 100644
--- a/runtime/permissions.rs
+++ b/runtime/permissions.rs
@@ -3,9 +3,6 @@
 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_path_util::normalize_path;
 use deno_permissions::AllowRunDescriptor;
 use deno_permissions::AllowRunDescriptorParseResult;
@@ -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))
     }
@@ -97,9 +96,9 @@ 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::parse(text.to_string())?)
     }
@@ -108,21 +107,21 @@ impl deno_permissions::PermissionDescriptorParser
   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 d7f2364a56..e088eb8ce5 100644
--- a/runtime/permissions/Cargo.toml
+++ b/runtime/permissions/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_permissions"
-version = "0.33.0"
+version = "0.37.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -23,6 +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 1e1321bb2f..6480f4bf58 100644
--- a/runtime/permissions/lib.rs
+++ b/runtime/permissions/lib.rs
@@ -1,11 +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::parking_lot::Mutex;
 use deno_core::serde::de;
 use deno_core::serde::Deserialize;
@@ -43,6 +37,21 @@ 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 {
+  access: String,
+  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.
 macro_rules! skip_check_if_is_permission_fully_granted {
@@ -104,7 +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
@@ -120,53 +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);
@@ -246,7 +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 {
@@ -262,7 +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 => {
@@ -270,7 +276,7 @@ impl UnitPermission {
       }
       ChildUnitPermissionArg::Granted => {
         if self.check().is_err() {
-          return Err(escalation_error());
+          return Err(ChildPermissionError::Escalation);
         }
         perm.state = PermissionState::Granted;
       }
@@ -327,7 +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;
@@ -402,7 +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)
   }
@@ -412,7 +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(
@@ -599,11 +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 {
@@ -612,7 +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;
       }
@@ -621,13 +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);
         }
       }
     }
@@ -698,7 +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)
   }
@@ -761,7 +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)
   }
@@ -796,22 +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 {
@@ -822,11 +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))
     }
@@ -870,7 +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)
   }
@@ -896,39 +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, ""),
@@ -943,11 +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)
@@ -956,10 +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))
@@ -1011,7 +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)
   }
@@ -1038,15 +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);
 
@@ -1084,7 +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)
   }
@@ -1131,14 +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 {
@@ -1210,7 +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)
   }
@@ -1280,6 +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);
 
@@ -1360,17 +1447,29 @@ 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(String);
 
 impl SysDescriptor {
-  pub fn parse(kind: String) -> Result<Self, AnyError> {
+  pub fn parse(kind: String) -> Result<Self, SysDescriptorParseError> {
     match kind.as_str() {
       "hostname" | "osRelease" | "osUptime" | "loadavg"
       | "networkInterfaces" | "systemMemoryInfo" | "uid" | "gid" | "cpus"
-      | "homedir" | "getegid" | "username" | "statfs" | "getPriority"
-      | "setPriority" => Ok(Self(kind)),
-      _ => Err(type_error(format!("unknown system info kind \"{kind}\""))),
+      | "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)),
     }
   }
 
@@ -1407,7 +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)
   }
@@ -1468,7 +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)
   }
@@ -1520,7 +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)
   }
@@ -1530,12 +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)
   }
@@ -1564,7 +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)
   }
@@ -1574,12 +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)
   }
@@ -1602,12 +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)
   }
@@ -1633,12 +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)
   }
@@ -1664,12 +1769,12 @@ 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)
   }
@@ -1692,12 +1797,12 @@ impl UnaryPermission<SysDescriptor> {
     &mut self,
     kind: &SysDescriptor,
     api_name: Option<&str>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionDeniedError> {
     skip_check_if_is_permission_fully_granted!(self);
     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)
   }
@@ -1726,11 +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)
   }
 
@@ -1773,7 +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)
   }
@@ -1781,12 +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"))
   }
@@ -1826,23 +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 {
@@ -1858,15 +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) => {
@@ -1885,10 +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
@@ -1940,14 +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)
@@ -1956,7 +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)
@@ -1965,7 +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)
@@ -1974,14 +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)
@@ -1990,14 +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),
     })
   }
@@ -2029,14 +2156,14 @@ 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),
     }
   }
@@ -2048,6 +2175,38 @@ pub enum CheckSpecifierKind {
   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
@@ -2080,7 +2239,7 @@ impl PermissionsContainer {
   pub fn create_child_permissions(
     &self,
     child_permissions_arg: ChildPermissionsArg,
-  ) -> Result<PermissionsContainer, AnyError> {
+  ) -> Result<PermissionsContainer, ChildPermissionError> {
     fn is_granted_unary(arg: &ChildUnaryPermissionArg) -> bool {
       match arg {
         ChildUnaryPermissionArg::Inherit | ChildUnaryPermissionArg::Granted => {
@@ -2118,48 +2277,71 @@ impl PermissionsContainer {
 
     // 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(Some(self.descriptor_parser.parse_read_descriptor(text)?))
-      })?;
-    worker_perms.write = inner
-      .write
-      .create_child_permissions(child_permissions_arg.write, |text| {
-        Ok(Some(self.descriptor_parser.parse_write_descriptor(text)?))
-      })?;
-    worker_perms.import = inner
-      .import
-      .create_child_permissions(child_permissions_arg.import, |text| {
-        Ok(Some(self.descriptor_parser.parse_import_descriptor(text)?))
-      })?;
-    worker_perms.net = inner
-      .net
-      .create_child_permissions(child_permissions_arg.net, |text| {
-        Ok(Some(self.descriptor_parser.parse_net_descriptor(text)?))
-      })?;
-    worker_perms.env = inner
-      .env
-      .create_child_permissions(child_permissions_arg.env, |text| {
-        Ok(Some(self.descriptor_parser.parse_env_descriptor(text)?))
-      })?;
-    worker_perms.sys = inner
-      .sys
-      .create_child_permissions(child_permissions_arg.sys, |text| {
-        Ok(Some(self.descriptor_parser.parse_sys_descriptor(text)?))
-      })?;
+    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(None),
+        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(Some(self.descriptor_parser.parse_ffi_descriptor(text)?))
-      })?;
+    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(),
@@ -2172,7 +2354,7 @@ impl PermissionsContainer {
     &self,
     specifier: &ModuleSpecifier,
     kind: CheckSpecifierKind,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     let mut inner = self.inner.lock();
     match specifier.scheme() {
       "file" => {
@@ -2181,17 +2363,20 @@ impl PermissionsContainer {
         }
 
         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()"),
-          ),
-          Err(_) => Err(uri_error(format!(
-            "Invalid file path.\n  Specifier: {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(()),
@@ -2216,7 +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))
   }
 
@@ -2226,7 +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() {
@@ -2244,7 +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() {
@@ -2268,7 +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);
@@ -2279,12 +2464,17 @@ 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)]
@@ -2298,7 +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))
   }
 
@@ -2308,7 +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() {
@@ -2326,7 +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() {
@@ -2343,8 +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
@@ -2355,7 +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);
@@ -2366,7 +2560,8 @@ impl PermissionsContainer {
       }
       .into_write(),
       Some(api_name),
-    )
+    )?;
+    Ok(())
   }
 
   #[inline(always)]
@@ -2374,7 +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() {
@@ -2391,13 +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)]
@@ -2406,38 +2606,50 @@ impl PermissionsContainer {
   }
 
   #[inline(always)]
-  pub fn check_sys(&self, kind: &str, api_name: &str) -> Result<(), AnyError> {
+  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
@@ -2549,13 +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)]
@@ -2563,17 +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() {
@@ -2587,14 +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"]
@@ -2602,7 +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() {
@@ -2620,7 +2838,7 @@ impl PermissionsContainer {
   pub fn query_read(
     &self,
     path: Option<&str>,
-  ) -> Result<PermissionState, AnyError> {
+  ) -> Result<PermissionState, PathResolveError> {
     let inner = self.inner.lock();
     let permission = &inner.read;
     if permission.is_allow_all() {
@@ -2630,7 +2848,7 @@ impl PermissionsContainer {
       permission.query(
         path
           .map(|path| {
-            Result::<_, AnyError>::Ok(
+            Ok::<_, PathResolveError>(
               self.descriptor_parser.parse_path_query(path)?.into_read(),
             )
           })
@@ -2644,7 +2862,7 @@ impl PermissionsContainer {
   pub fn query_write(
     &self,
     path: Option<&str>,
-  ) -> Result<PermissionState, AnyError> {
+  ) -> Result<PermissionState, PathResolveError> {
     let inner = self.inner.lock();
     let permission = &inner.write;
     if permission.is_allow_all() {
@@ -2654,7 +2872,7 @@ impl PermissionsContainer {
       permission.query(
         path
           .map(|path| {
-            Result::<_, AnyError>::Ok(
+            Ok::<_, PathResolveError>(
               self.descriptor_parser.parse_path_query(path)?.into_write(),
             )
           })
@@ -2668,7 +2886,7 @@ impl PermissionsContainer {
   pub fn query_net(
     &self,
     host: Option<&str>,
-  ) -> Result<PermissionState, AnyError> {
+  ) -> Result<PermissionState, NetDescriptorParseError> {
     let inner = self.inner.lock();
     let permission = &inner.net;
     if permission.is_allow_all() {
@@ -2699,7 +2917,7 @@ impl PermissionsContainer {
   pub fn query_sys(
     &self,
     kind: Option<&str>,
-  ) -> Result<PermissionState, AnyError> {
+  ) -> Result<PermissionState, SysDescriptorParseError> {
     let inner = self.inner.lock();
     let permission = &inner.sys;
     if permission.is_allow_all() {
@@ -2719,7 +2937,7 @@ impl PermissionsContainer {
   pub fn query_run(
     &self,
     cmd: Option<&str>,
-  ) -> Result<PermissionState, AnyError> {
+  ) -> Result<PermissionState, RunDescriptorParseError> {
     let inner = self.inner.lock();
     let permission = &inner.run;
     if permission.is_allow_all() {
@@ -2739,7 +2957,7 @@ impl PermissionsContainer {
   pub fn query_ffi(
     &self,
     path: Option<&str>,
-  ) -> Result<PermissionState, AnyError> {
+  ) -> Result<PermissionState, PathResolveError> {
     let inner = self.inner.lock();
     let permission = &inner.ffi;
     if permission.is_allow_all() {
@@ -2749,7 +2967,7 @@ impl PermissionsContainer {
       permission.query(
         path
           .map(|path| {
-            Result::<_, AnyError>::Ok(
+            Ok::<_, PathResolveError>(
               self.descriptor_parser.parse_path_query(path)?.into_ffi(),
             )
           })
@@ -2765,12 +2983,12 @@ impl PermissionsContainer {
   pub fn revoke_read(
     &self,
     path: Option<&str>,
-  ) -> Result<PermissionState, AnyError> {
+  ) -> Result<PermissionState, PathResolveError> {
     Ok(
       self.inner.lock().read.revoke(
         path
           .map(|path| {
-            Result::<_, AnyError>::Ok(
+            Ok::<_, PathResolveError>(
               self.descriptor_parser.parse_path_query(path)?.into_read(),
             )
           })
@@ -2784,12 +3002,12 @@ impl PermissionsContainer {
   pub fn revoke_write(
     &self,
     path: Option<&str>,
-  ) -> Result<PermissionState, AnyError> {
+  ) -> Result<PermissionState, PathResolveError> {
     Ok(
       self.inner.lock().write.revoke(
         path
           .map(|path| {
-            Result::<_, AnyError>::Ok(
+            Ok::<_, PathResolveError>(
               self.descriptor_parser.parse_path_query(path)?.into_write(),
             )
           })
@@ -2803,7 +3021,7 @@ impl PermissionsContainer {
   pub fn revoke_net(
     &self,
     host: Option<&str>,
-  ) -> Result<PermissionState, AnyError> {
+  ) -> Result<PermissionState, NetDescriptorParseError> {
     Ok(
       self.inner.lock().net.revoke(
         match host {
@@ -2824,7 +3042,7 @@ impl PermissionsContainer {
   pub fn revoke_sys(
     &self,
     kind: Option<&str>,
-  ) -> Result<PermissionState, AnyError> {
+  ) -> Result<PermissionState, SysDescriptorParseError> {
     Ok(
       self.inner.lock().sys.revoke(
         kind
@@ -2839,7 +3057,7 @@ impl PermissionsContainer {
   pub fn revoke_run(
     &self,
     cmd: Option<&str>,
-  ) -> Result<PermissionState, AnyError> {
+  ) -> Result<PermissionState, RunDescriptorParseError> {
     Ok(
       self.inner.lock().run.revoke(
         cmd
@@ -2854,12 +3072,12 @@ impl PermissionsContainer {
   pub fn revoke_ffi(
     &self,
     path: Option<&str>,
-  ) -> Result<PermissionState, AnyError> {
+  ) -> Result<PermissionState, PathResolveError> {
     Ok(
       self.inner.lock().ffi.revoke(
         path
           .map(|path| {
-            Result::<_, AnyError>::Ok(
+            Ok::<_, PathResolveError>(
               self.descriptor_parser.parse_path_query(path)?.into_ffi(),
             )
           })
@@ -2875,12 +3093,12 @@ impl PermissionsContainer {
   pub fn request_read(
     &self,
     path: Option<&str>,
-  ) -> Result<PermissionState, AnyError> {
+  ) -> Result<PermissionState, PathResolveError> {
     Ok(
       self.inner.lock().read.request(
         path
           .map(|path| {
-            Result::<_, AnyError>::Ok(
+            Ok::<_, PathResolveError>(
               self.descriptor_parser.parse_path_query(path)?.into_read(),
             )
           })
@@ -2894,12 +3112,12 @@ impl PermissionsContainer {
   pub fn request_write(
     &self,
     path: Option<&str>,
-  ) -> Result<PermissionState, AnyError> {
+  ) -> Result<PermissionState, PathResolveError> {
     Ok(
       self.inner.lock().write.request(
         path
           .map(|path| {
-            Result::<_, AnyError>::Ok(
+            Ok::<_, PathResolveError>(
               self.descriptor_parser.parse_path_query(path)?.into_write(),
             )
           })
@@ -2913,7 +3131,7 @@ impl PermissionsContainer {
   pub fn request_net(
     &self,
     host: Option<&str>,
-  ) -> Result<PermissionState, AnyError> {
+  ) -> Result<PermissionState, NetDescriptorParseError> {
     Ok(
       self.inner.lock().net.request(
         match host {
@@ -2934,7 +3152,7 @@ impl PermissionsContainer {
   pub fn request_sys(
     &self,
     kind: Option<&str>,
-  ) -> Result<PermissionState, AnyError> {
+  ) -> Result<PermissionState, SysDescriptorParseError> {
     Ok(
       self.inner.lock().sys.request(
         kind
@@ -2949,7 +3167,7 @@ impl PermissionsContainer {
   pub fn request_run(
     &self,
     cmd: Option<&str>,
-  ) -> Result<PermissionState, AnyError> {
+  ) -> Result<PermissionState, RunDescriptorParseError> {
     Ok(
       self.inner.lock().run.request(
         cmd
@@ -2964,12 +3182,12 @@ impl PermissionsContainer {
   pub fn request_ffi(
     &self,
     path: Option<&str>,
-  ) -> Result<PermissionState, AnyError> {
+  ) -> Result<PermissionState, PathResolveError> {
     Ok(
       self.inner.lock().ffi.request(
         path
           .map(|path| {
-            Result::<_, AnyError>::Ok(
+            Ok::<_, PathResolveError>(
               self.descriptor_parser.parse_path_query(path)?.into_ffi(),
             )
           })
@@ -3005,10 +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,
@@ -3269,65 +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>;
+  ) -> Result<RunQueryDescriptor, RunDescriptorParseError>;
 }
 
 static IS_STANDALONE: AtomicFlag = AtomicFlag::lowered();
@@ -3370,49 +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> {
+    ) -> 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)),
       ))
@@ -3421,7 +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 {
@@ -3432,14 +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(),
@@ -3449,8 +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)
     }
   }
 
@@ -4331,7 +4553,6 @@ mod tests {
         None,
         false,
       )
-      .unwrap()
     };
 
     prompt_value.set(true);
@@ -4558,13 +4779,12 @@ mod tests {
         .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()
       }
     );
diff --git a/runtime/permissions/prompter.rs b/runtime/permissions/prompter.rs
index 316911edc1..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;
@@ -101,8 +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;
@@ -117,7 +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
@@ -137,7 +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)
@@ -156,8 +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;
@@ -194,18 +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;
@@ -220,34 +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(())
@@ -269,7 +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)
   }
 }
diff --git a/runtime/shared.rs b/runtime/shared.rs
index 02dfd18719..f7d76f67a7 100644
--- a/runtime/shared.rs
+++ b/runtime/shared.rs
@@ -98,6 +98,7 @@ 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 +110,9 @@ 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 041132f971..251ee5f41c 100644
--- a/runtime/snapshot.rs
+++ b/runtime/snapshot.rs
@@ -5,12 +5,12 @@ use crate::ops::bootstrap::SnapshotOptions;
 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;
@@ -26,7 +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!")
   }
 }
@@ -42,7 +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!")
   }
 
@@ -50,28 +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!")
   }
 }
@@ -81,20 +79,27 @@ 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 {
@@ -104,14 +109,14 @@ impl deno_node::NodePermissions for Permissions {
     &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!")
   }
 }
@@ -121,7 +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!")
   }
 
@@ -129,7 +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!")
   }
 
@@ -137,7 +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!")
   }
 
@@ -145,7 +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!")
   }
 }
@@ -158,7 +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!")
   }
 
@@ -166,11 +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!")
   }
 
@@ -179,7 +187,7 @@ impl deno_fs::FsPermissions for Permissions {
     _path: &Path,
     _display: &str,
     _api_name: &str,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 
@@ -187,7 +195,7 @@ impl deno_fs::FsPermissions for Permissions {
     &mut self,
     _path: &str,
     _api_name: &str,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 
@@ -195,11 +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!")
   }
 
@@ -208,7 +219,7 @@ impl deno_fs::FsPermissions for Permissions {
     _path: &Path,
     _display: &str,
     _api_name: &str,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 
@@ -216,7 +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!")
   }
 
@@ -224,7 +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!")
   }
 }
@@ -234,7 +245,7 @@ impl deno_kv::sqlite::SqliteDbHandlerPermissions for Permissions {
     &mut self,
     _path: &str,
     _api_name: &str,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, PermissionCheckError> {
     unreachable!("snapshotting!")
   }
 
@@ -242,7 +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!")
   }
 }
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 f560ce17ec..61e5c77029 100644
--- a/runtime/web_worker.rs
+++ b/runtime/web_worker.rs
@@ -166,7 +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.
@@ -176,8 +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
@@ -263,11 +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
@@ -562,7 +562,7 @@ impl WebWorker {
       extension_transpiler: Some(Rc::new(|specifier, source| {
         maybe_transpile_source(specifier, source)
       })),
-      inspector: services.maybe_inspector_server.is_some(),
+      inspector: true,
       feature_checker: Some(services.feature_checker),
       op_metrics_factory_fn,
       import_meta_resolve_callback: Some(Box::new(
@@ -579,18 +579,18 @@ impl WebWorker {
       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) = services.maybe_inspector_server {
       server.register_inspector(
         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) = {
diff --git a/runtime/worker.rs b/runtime/worker.rs
index 477d3b880c..88a61fa938 100644
--- a/runtime/worker.rs
+++ b/runtime/worker.rs
@@ -20,6 +20,8 @@ use deno_core::CompiledWasmModuleStore;
 use deno_core::Extension;
 use deno_core::FeatureChecker;
 use deno_core::GetErrorClassFn;
+use deno_core::InspectorSessionKind;
+use deno_core::InspectorSessionOptions;
 use deno_core::JsRuntime;
 use deno_core::LocalInspectorSession;
 use deno_core::ModuleCodeString;
@@ -486,7 +488,7 @@ impl MainWorker {
       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(services.feature_checker.clone()),
       op_metrics_factory_fn,
@@ -544,6 +546,12 @@ 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(),
@@ -551,13 +559,8 @@ 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,
@@ -792,7 +795,11 @@ 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/rust-toolchain.toml b/rust-toolchain.toml
index f19c7df470..3d572e0d69 100644
--- a/rust-toolchain.toml
+++ b/rust-toolchain.toml
@@ -1,3 +1,3 @@
 [toolchain]
-channel = "1.81.0"
+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/flags_tests.rs b/tests/integration/flags_tests.rs
index 455507b9fa..663da363da 100644
--- a/tests/integration/flags_tests.rs
+++ b/tests/integration/flags_tests.rs
@@ -18,8 +18,8 @@ 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",
     "Type-check the dependencies",
     "Compile the script into a self contained executable",
diff --git a/tests/integration/lsp_tests.rs b/tests/integration/lsp_tests.rs
index 85e02041ed..af5f9de23e 100644
--- a/tests/integration/lsp_tests.rs
+++ b/tests/integration/lsp_tests.rs
@@ -1827,15 +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;
         }
 
@@ -1854,8 +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",
@@ -1864,65 +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();
 }
@@ -5853,7 +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": {
@@ -6294,6 +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() {
@@ -6367,6 +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",
@@ -6477,6 +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",
@@ -6505,23 +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(
@@ -6666,7 +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",
           }],
         }],
       },
@@ -6675,6 +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();
@@ -6986,7 +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"
           }]
         }]
       }
@@ -7039,7 +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"
           }]
         }]
       },
@@ -7139,7 +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",
           }],
         }],
       },
@@ -7183,7 +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",
           }],
         }],
       },
@@ -7863,6 +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();
@@ -7975,8 +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;
@@ -8057,7 +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",
               },
             ],
           },
@@ -15261,25 +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!(
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/run_tests.rs b/tests/integration/run_tests.rs
index db9f79556e..e29ecc486c 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()
@@ -1234,141 +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:
@@ -1378,60 +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",
@@ -1439,42 +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,
@@ -1489,138 +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();
@@ -1642,216 +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",
@@ -1866,131 +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",
@@ -2003,289 +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()
@@ -2523,7 +1172,6 @@ fn dont_cache_on_check_fail() {
 
 mod permissions {
   use test_util as util;
-  use test_util::itest;
   use util::TestContext;
 
   #[test]
@@ -2973,31 +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()
@@ -3033,63 +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() {
@@ -3137,24 +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() {
@@ -3278,85 +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
@@ -3395,81 +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();
@@ -3502,18 +1898,6 @@ 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()
@@ -3544,57 +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();
@@ -3605,18 +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",
@@ -3627,51 +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();
@@ -3890,6 +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;
@@ -3897,11 +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;
 
@@ -3911,9 +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())
     }
@@ -4211,48 +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();
@@ -4434,24 +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() {
@@ -4559,12 +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",
@@ -4678,25 +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",
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/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/node_compat/config.jsonc b/tests/node_compat/config.jsonc
index 75f463342e..16951d9ede 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",
@@ -90,8 +87,6 @@
       "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 +235,7 @@
       "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",
@@ -450,6 +446,7 @@
       "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/runner/TODO.md b/tests/node_compat/runner/TODO.md
index 11b5d28053..231a4f62c9 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)
@@ -1879,7 +1878,6 @@ 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/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/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-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/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/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/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/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/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/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/package.json.out b/tests/specs/add/dev/package.json.out
index 866724397f..d5ca56e004 100644
--- a/tests/specs/add/dev/package.json.out
+++ b/tests/specs/add/dev/package.json.out
@@ -1,5 +1,3 @@
 {
-  "devDependencies": {
-    "@denotest/esm-basic": "^1.0.0"
-  }
+  "devDependencies": { "@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/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_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/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/testdata/run/check_js_points_to_ts/foo.d.ts b/tests/specs/add/package_json_and_deno_json/subdir/mod.ts
similarity index 100%
rename from tests/testdata/run/check_js_points_to_ts/foo.d.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/empty.ts b/tests/specs/add/update_lockfile_if_package_json/package.json
similarity index 100%
rename from tests/testdata/run/empty.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/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/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/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/detect_cjs/__test__.jsonc b/tests/specs/compile/detect_cjs/__test__.jsonc
index 32bebb7a57..0abf121f05 100644
--- a/tests/specs/compile/detect_cjs/__test__.jsonc
+++ b/tests/specs/compile/detect_cjs/__test__.jsonc
@@ -1,24 +1,27 @@
 {
   "tempDir": true,
   "steps": [{
+    "args": "install",
+    "output": "[WILDCARD]"
+  }, {
     "if": "unix",
-    "args": "compile --allow-read --output main main.js",
+    "args": "compile --output main main.js",
     "output": "compile.out"
   }, {
     "if": "unix",
     "commandName": "./main",
     "args": [],
     "output": "output.out",
-    "exitCode": 1
+    "exitCode": 0
   }, {
     "if": "windows",
-    "args": "compile --allow-read --output main.exe main.js",
+    "args": "compile --output main.exe main.js",
     "output": "compile.out"
   }, {
     "if": "windows",
     "commandName": "./main.exe",
     "args": [],
     "output": "output.out",
-    "exitCode": 1
+    "exitCode": 0
   }]
 }
diff --git a/tests/specs/compile/detect_cjs/add.js b/tests/specs/compile/detect_cjs/add.js
index 2a886fbc18..94b0263f0e 100644
--- a/tests/specs/compile/detect_cjs/add.js
+++ b/tests/specs/compile/detect_cjs/add.js
@@ -1,3 +1,3 @@
 module.exports.add = function (a, b) {
-  return a + b;
+  return require("./subtract.ts").subtract(a, -b);
 };
diff --git a/tests/specs/compile/detect_cjs/compile.out b/tests/specs/compile/detect_cjs/compile.out
index 6509b7f29c..913e363c3e 100644
--- a/tests/specs/compile/detect_cjs/compile.out
+++ b/tests/specs/compile/detect_cjs/compile.out
@@ -1,3 +1,2 @@
-Warning --unstable-detect-cjs is not properly supported in deno compile. The compiled executable may encounter runtime errors.
 Check file:///[WILDLINE]/main.js
 Compile file:///[WILDLINE]
diff --git a/tests/specs/compile/detect_cjs/output.out b/tests/specs/compile/detect_cjs/output.out
index b53c443698..00750edc07 100644
--- a/tests/specs/compile/detect_cjs/output.out
+++ b/tests/specs/compile/detect_cjs/output.out
@@ -1 +1 @@
-error: Module not found: file:///[WILDLINE]/add.js
+3
diff --git a/tests/specs/compile/detect_cjs/package.json b/tests/specs/compile/detect_cjs/package.json
index 5bbefffbab..6e65b32ed5 100644
--- a/tests/specs/compile/detect_cjs/package.json
+++ b/tests/specs/compile/detect_cjs/package.json
@@ -1,3 +1,6 @@
 {
-  "type": "commonjs"
+  "type": "commonjs",
+  "dependencies": {
+    "@types/node": "*"
+  }
 }
diff --git a/tests/specs/compile/detect_cjs/subtract.ts b/tests/specs/compile/detect_cjs/subtract.ts
new file mode 100644
index 0000000000..e4f6760b77
--- /dev/null
+++ b/tests/specs/compile/detect_cjs/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/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/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/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/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/lint/node_globals_no_duplicate_imports/main.out b/tests/specs/lint/node_globals_no_duplicate_imports/main.out
index 56df10eba4..058b80795d 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 +2,6 @@ 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";.
diff --git a/tests/specs/lockfile/frozen_lockfile/__test__.jsonc b/tests/specs/lockfile/frozen_lockfile/__test__.jsonc
index 7a7b9c233a..07ec2c4c14 100644
--- a/tests/specs/lockfile/frozen_lockfile/__test__.jsonc
+++ b/tests/specs/lockfile/frozen_lockfile/__test__.jsonc
@@ -183,6 +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/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/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/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/compare_globals/__test__.jsonc b/tests/specs/npm/compare_globals/__test__.jsonc
index e096ddeb22..96458306a7 100644
--- a/tests/specs/npm/compare_globals/__test__.jsonc
+++ b/tests/specs/npm/compare_globals/__test__.jsonc
@@ -1,4 +1,4 @@
 {
-  "args": "run --allow-read --check=all compare_globals/main.ts",
-  "output": "compare_globals/main.out"
+  "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 90%
rename from tests/specs/npm/compare_globals/compare_globals/main.out
rename to tests/specs/npm/compare_globals/main.out
index 5be6125b08..290e9c3b23 100644
--- a/tests/specs/npm/compare_globals/compare_globals/main.out
+++ b/tests/specs/npm/compare_globals/main.out
@@ -8,10 +8,11 @@ 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/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_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/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 d715db8a94..00750edc07 100644
--- a/tests/specs/npm/require_type_commonjs/main.out
+++ b/tests/specs/npm/require_type_commonjs/main.out
@@ -1,4 +1 @@
-error: 'import', and 'export' cannot be used outside of module code at file://[WILDCARD]/@denotest/type-commonjs/1.0.0/index.js:1:1
-
-  export {};
-  ~~~~~~
+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/typescript_file_in_package/__test__.jsonc b/tests/specs/npm/typescript_file_in_package/__test__.jsonc
index 08979ed257..7b5c5e1b67 100644
--- a/tests/specs/npm/typescript_file_in_package/__test__.jsonc
+++ b/tests/specs/npm/typescript_file_in_package/__test__.jsonc
@@ -1,5 +1,5 @@
 {
-  "args": "run typescript_file_in_package/main.ts",
-  "output": "typescript_file_in_package/main.out",
+  "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 b3faa87900..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%2ftypescript-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/remove/package_json/rm_add_package.json.out b/tests/specs/remove/package_json/rm_add_package.json.out
index 866724397f..d5ca56e004 100644
--- a/tests/specs/remove/package_json/rm_add_package.json.out
+++ b/tests/specs/remove/package_json/rm_add_package.json.out
@@ -1,5 +1,3 @@
 {
-  "devDependencies": {
-    "@denotest/esm-basic": "^1.0.0"
-  }
+  "devDependencies": { "@denotest/esm-basic": "^1.0.0" }
 }
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/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/package_json_type/commonjs/add.js b/tests/specs/run/cts/cjs_import_cts/add.cts
similarity index 100%
rename from tests/specs/run/package_json_type/commonjs/add.js
rename to tests/specs/run/cts/cjs_import_cts/add.cts
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 100%
rename from tests/testdata/run/deny_some_permission_args.out
rename to tests/specs/run/deny_some_permission_args/deny_some_permission_args.out
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/exports_error.out b/tests/specs/run/import_common_js/exports_error.out
index 299a46438c..b979cce5c7 100644
--- a/tests/specs/run/import_common_js/exports_error.out
+++ b/tests/specs/run/import_common_js/exports_error.out
@@ -9,4 +9,4 @@ Object.defineProperty(exports, "__esModule", { value: true });
           or change the file extension to .cjs,
           or add package.json next to the file with "type": "commonjs" option
           and pass --unstable-detect-cjs flag.
-    hint: See https://docs.deno.com/go/commonjs for details
+    docs: https://docs.deno.com/go/commonjs
diff --git a/tests/specs/run/import_common_js/module_error.out b/tests/specs/run/import_common_js/module_error.out
index 1c1140fe42..654ee838dd 100644
--- a/tests/specs/run/import_common_js/module_error.out
+++ b/tests/specs/run/import_common_js/module_error.out
@@ -9,4 +9,4 @@ module.exports = {
           or change the file extension to .cjs,
           or add package.json next to the file with "type": "commonjs" option
           and pass --unstable-detect-cjs flag.
-    hint: See https://docs.deno.com/go/commonjs for details
+    docs: https://docs.deno.com/go/commonjs
diff --git a/tests/specs/run/import_common_js/require_error.out b/tests/specs/run/import_common_js/require_error.out
index ebc6b6fa43..81ffd6591f 100644
--- a/tests/specs/run/import_common_js/require_error.out
+++ b/tests/specs/run/import_common_js/require_error.out
@@ -9,4 +9,4 @@ const process = require("process");
           or change the file extension to .cjs,
           or add package.json next to the file with "type": "commonjs" option
           and pass --unstable-detect-cjs flag.
-    hint: See https://docs.deno.com/go/commonjs for details
+    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/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_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..4980e6d129
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/buffer.out
@@ -0,0 +1,7 @@
+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";.
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..ecd34babef
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/clear_immediate.out
@@ -0,0 +1,7 @@
+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";.
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..e090d32e29
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/global.out
@@ -0,0 +1,7 @@
+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.
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..38859ff5d7
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/set_immediate.out
@@ -0,0 +1,7 @@
+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";.
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/add.out b/tests/specs/run/package_json/invalid_value/add.out
index 9b7493c1a2..32d9acaed6 100644
--- a/tests/specs/run/package_json/invalid_value/add.out
+++ b/tests/specs/run/package_json/invalid_value/add.out
@@ -1,5 +1,6 @@
 Add npm:cowsay@1.5.0
-error: Failed to install from package.json
+error: Failed to install '@denotest/cjs-default-export'
+    at file:///[WILDLINE]/package.json
 
 Caused by:
     0: Invalid version requirement
diff --git a/tests/specs/run/package_json/invalid_value/install.out b/tests/specs/run/package_json/invalid_value/install.out
index cc82b345b0..ca3492ab22 100644
--- a/tests/specs/run/package_json/invalid_value/install.out
+++ b/tests/specs/run/package_json/invalid_value/install.out
@@ -1,4 +1,5 @@
-error: Failed to install from package.json
+error: Failed to install '@denotest/cjs-default-export'
+    at file:///[WILDLINE]/package.json
 
 Caused by:
     0: Invalid version requirement
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/__test__.jsonc b/tests/specs/run/package_json_type/commonjs/basic/__test__.jsonc
similarity index 100%
rename from tests/specs/run/package_json_type/commonjs/__test__.jsonc
rename to tests/specs/run/package_json_type/commonjs/basic/__test__.jsonc
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/deno.jsonc b/tests/specs/run/package_json_type/commonjs/basic/deno.jsonc
similarity index 100%
rename from tests/specs/run/package_json_type/commonjs/deno.jsonc
rename to tests/specs/run/package_json_type/commonjs/basic/deno.jsonc
diff --git a/tests/specs/run/package_json_type/commonjs/import_import_meta.js b/tests/specs/run/package_json_type/commonjs/basic/import_import_meta.js
similarity index 100%
rename from tests/specs/run/package_json_type/commonjs/import_import_meta.js
rename to tests/specs/run/package_json_type/commonjs/basic/import_import_meta.js
diff --git a/tests/specs/run/package_json_type/commonjs/import_meta.js b/tests/specs/run/package_json_type/commonjs/basic/import_meta.js
similarity index 100%
rename from tests/specs/run/package_json_type/commonjs/import_meta.js
rename to tests/specs/run/package_json_type/commonjs/basic/import_meta.js
diff --git a/tests/specs/run/package_json_type/commonjs/main_cjs.js b/tests/specs/run/package_json_type/commonjs/basic/main_cjs.js
similarity index 100%
rename from tests/specs/run/package_json_type/commonjs/main_cjs.js
rename to tests/specs/run/package_json_type/commonjs/basic/main_cjs.js
diff --git a/tests/specs/run/package_json_type/commonjs/main_esm.js b/tests/specs/run/package_json_type/commonjs/basic/main_esm.js
similarity index 100%
rename from tests/specs/run/package_json_type/commonjs/main_esm.js
rename to tests/specs/run/package_json_type/commonjs/basic/main_esm.js
diff --git a/tests/specs/run/package_json_type/commonjs/main_esm_import_meta.js b/tests/specs/run/package_json_type/commonjs/basic/main_esm_import_meta.js
similarity index 100%
rename from tests/specs/run/package_json_type/commonjs/main_esm_import_meta.js
rename to tests/specs/run/package_json_type/commonjs/basic/main_esm_import_meta.js
diff --git a/tests/specs/run/package_json_type/commonjs/main_esm_import_meta.out b/tests/specs/run/package_json_type/commonjs/basic/main_esm_import_meta.out
similarity index 100%
rename from tests/specs/run/package_json_type/commonjs/main_esm_import_meta.out
rename to tests/specs/run/package_json_type/commonjs/basic/main_esm_import_meta.out
diff --git a/tests/specs/run/package_json_type/commonjs/main_mix.js b/tests/specs/run/package_json_type/commonjs/basic/main_mix.js
similarity index 100%
rename from tests/specs/run/package_json_type/commonjs/main_mix.js
rename to tests/specs/run/package_json_type/commonjs/basic/main_mix.js
diff --git a/tests/specs/run/package_json_type/commonjs/main_mix.out b/tests/specs/run/package_json_type/commonjs/basic/main_mix.out
similarity index 90%
rename from tests/specs/run/package_json_type/commonjs/main_mix.out
rename to tests/specs/run/package_json_type/commonjs/basic/main_mix.out
index 67d316fcd1..78f421644c 100644
--- a/tests/specs/run/package_json_type/commonjs/main_mix.out
+++ b/tests/specs/run/package_json_type/commonjs/basic/main_mix.out
@@ -10,4 +10,4 @@ console.log(require("./add").add(1, 2));
           or change the file extension to .cjs,
           or add package.json next to the file with "type": "commonjs" option
           and pass --unstable-detect-cjs flag.
-    hint: See https://docs.deno.com/go/commonjs for details
+    docs: https://docs.deno.com/go/commonjs
diff --git a/tests/specs/run/package_json_type/commonjs/not_import_meta.js b/tests/specs/run/package_json_type/commonjs/basic/not_import_meta.js
similarity index 100%
rename from tests/specs/run/package_json_type/commonjs/not_import_meta.js
rename to tests/specs/run/package_json_type/commonjs/basic/not_import_meta.js
diff --git a/tests/specs/run/package_json_type/commonjs/package.json b/tests/specs/run/package_json_type/commonjs/basic/package.json
similarity index 100%
rename from tests/specs/run/package_json_type/commonjs/package.json
rename to tests/specs/run/package_json_type/commonjs/basic/package.json
diff --git a/tests/specs/run/package_json_type/commonjs/tla.js b/tests/specs/run/package_json_type/commonjs/basic/tla.js
similarity index 100%
rename from tests/specs/run/package_json_type/commonjs/tla.js
rename to tests/specs/run/package_json_type/commonjs/basic/tla.js
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..192ddb98c4
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/jsx/deno.jsonc
@@ -0,0 +1,10 @@
+{
+  "nodeModulesDir": "auto",
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "react"
+  },
+  "unstable": [
+    "detect-cjs"
+  ]
+}
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/main_cjs.out b/tests/specs/run/package_json_type/none/main_cjs.out
index 66213dbdb0..8d34808fb1 100644
--- a/tests/specs/run/package_json_type/none/main_cjs.out
+++ b/tests/specs/run/package_json_type/none/main_cjs.out
@@ -9,4 +9,4 @@ const { add } = require("./add");
           or change the file extension to .cjs,
           or add package.json next to the file with "type": "commonjs" option
           and pass --unstable-detect-cjs flag.
-    hint: See https://docs.deno.com/go/commonjs for details
+    docs: https://docs.deno.com/go/commonjs
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/output.out b/tests/specs/run/remote_cjs_main/output.out
index f75c33907a..360934acb7 100644
--- a/tests/specs/run/remote_cjs_main/output.out
+++ b/tests/specs/run/remote_cjs_main/output.out
@@ -1,3 +1,3 @@
 Download http://localhost:4545/run/add.cjs
-error: Expected a JavaScript or TypeScript module, but identified a Cjs module. Importing these types of modules is currently not supported.
+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..57b842b345 100644
--- a/tests/specs/run/require_esm/main.out
+++ b/tests/specs/run/require_esm/main.out
@@ -1,6 +1,6 @@
 [Module: null prototype] { sync_js: 1 }
 [Module: null prototype] { sync_mjs: 1 }
-error: Uncaught Error: Top-level await is not allowed in synchronous evaluation
+error: Uncaught (in promise) 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])
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/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-----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+-----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-----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+-----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_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/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/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/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/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/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/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/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 42cff7c705..06f5dd7e61 100644
--- a/tests/unit/console_test.ts
+++ b/tests/unit/console_test.ts
@@ -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]);
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/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_node/fs_test.ts b/tests/unit_node/fs_test.ts
index ac9c4a53e7..631608d7cc 100644
--- a/tests/unit_node/fs_test.ts
+++ b/tests/unit_node/fs_test.ts
@@ -26,6 +26,7 @@ import {
   cp,
   FileHandle,
   open,
+  stat,
   writeFile,
 } from "node:fs/promises";
 import process from "node:process";
@@ -123,6 +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 () => {
@@ -233,3 +276,14 @@ Deno.test("[node/fs] copyFile COPYFILE_EXCL works", async () => {
     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/http_test.ts b/tests/unit_node/http_test.ts
index 0faf7fb345..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";
 
@@ -318,14 +322,10 @@ Deno.test("[node/http] IncomingRequest socket has remoteAddress + remotePort", a
     // deno-lint-ignore no-explicit-any
     const port = (server.address() as any).port;
     const res = await fetch(
-      `http://localhost:${port}/`,
+      `http://127.0.0.1:${port}/`,
     );
     await res.arrayBuffer();
-    if (Deno.build.os === "windows") {
-      assertEquals(remoteAddress, "127.0.0.1");
-    } else {
-      assertEquals(remoteAddress, "::1");
-    }
+    assertEquals(remoteAddress, "127.0.0.1");
     assertEquals(typeof remotePort, "number");
     server.close(() => resolve());
   });
@@ -1704,3 +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:${port}`);
+    await res.body?.cancel();
+    server.close(() => {
+      resolve();
+    });
+  });
+
+  await promise;
+});
diff --git a/tests/unit_node/tls_test.ts b/tests/unit_node/tls_test.ts
index 847ec2dde3..43d6205b0b 100644
--- a/tests/unit_node/tls_test.ts
+++ b/tests/unit_node/tls_test.ts
@@ -32,15 +32,13 @@ for (
 ) {
   Deno.test(`tls.connect sends correct ALPN: '${alpnServer}' + '${alpnClient}' = '${expected}'`, async () => {
     const listener = Deno.listenTls({
-      hostname: "localhost",
       port: 0,
       key,
       cert,
       alpnProtocols: alpnServer,
     });
     const outgoing = tls.connect({
-      host: "::1",
-      servername: "localhost",
+      host: "localhost",
       port: listener.addr.port,
       ALPNProtocols: alpnClient,
       secureContext: {
@@ -63,7 +61,6 @@ Deno.test("tls.connect makes tls connection", async () => {
   const ctl = new AbortController();
   let port;
   const serve = Deno.serve({
-    hostname: "localhost",
     port: 0,
     key,
     cert,
@@ -74,8 +71,7 @@ Deno.test("tls.connect makes tls connection", async () => {
   await delay(200);
 
   const conn = tls.connect({
-    host: "::1",
-    servername: "localhost",
+    host: "localhost",
     port,
     secureContext: {
       ca: rootCaCert,
@@ -106,7 +102,6 @@ Deno.test("tls.connect mid-read tcp->tls upgrade", async () => {
   const { promise, resolve } = Promise.withResolvers<void>();
   const ctl = new AbortController();
   const serve = Deno.serve({
-    hostname: "localhost",
     port: 8443,
     key,
     cert,
@@ -116,8 +111,7 @@ Deno.test("tls.connect mid-read tcp->tls upgrade", async () => {
   await delay(200);
 
   const conn = tls.connect({
-    host: "::1",
-    servername: "localhost",
+    host: "localhost",
     port: 8443,
     secureContext: {
       ca: rootCaCert,
@@ -235,3 +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 a47c231a18..6267018b12 100644
--- a/tests/unit_node/util_test.ts
+++ b/tests/unit_node/util_test.ts
@@ -353,3 +353,8 @@ 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/zlib_test.ts b/tests/unit_node/zlib_test.ts
index 8bce5ce7d1..0eff95445d 100644
--- a/tests/unit_node/zlib_test.ts
+++ b/tests/unit_node/zlib_test.ts
@@ -10,6 +10,7 @@ import {
   createBrotliCompress,
   createBrotliDecompress,
   createDeflate,
+  gzip,
   gzipSync,
   unzipSync,
 } from "node:zlib";
@@ -210,3 +211,17 @@ 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);
+});
diff --git a/tests/util/server/Cargo.toml b/tests/util/server/Cargo.toml
index aee7ef0be6..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
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/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 8d42fed78b..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
   }
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..d9adde5420 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);
   }
@@ -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/tools/lint.js b/tools/lint.js
index 1f3f56498b..cc595c2b13 100755
--- a/tools/lint.js
+++ b/tools/lint.js
@@ -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) {
@@ -218,7 +219,7 @@ async function ensureNoNewITests() {
     "pm_tests.rs": 0,
     "publish_tests.rs": 0,
     "repl_tests.rs": 0,
-    "run_tests.rs": 331,
+    "run_tests.rs": 24,
     "shared_library_tests.rs": 0,
     "task_tests.rs": 2,
     "test_tests.rs": 0,
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/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}`;