diff --git a/cli/node/mod.rs b/cli/node/mod.rs
index fc4db33ee2..fa6f0bddaa 100644
--- a/cli/node/mod.rs
+++ b/cli/node/mod.rs
@@ -636,17 +636,22 @@ pub fn load_cjs_module_from_ext_node(
   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(module) {{
+    r#"(function loadCjsModule(module, inspectBrk) {{
+      if (inspectBrk) {{
+        Deno[Deno.internal].require.setInspectBrk();
+      }}
       Deno[Deno.internal].require.Module._load(module, null, {main});
-    }})('{module}');"#,
+    }})('{module}', {inspect_brk});"#,
     main = main,
     module = escape_for_single_quote_string(module),
+    inspect_brk = inspect_brk,
   );
 
   js_runtime.execute_script(&located_script_name!(), source_code)?;
diff --git a/cli/tests/inspector_tests.rs b/cli/tests/inspector_tests.rs
index 94ebbb2058..407e8f071f 100644
--- a/cli/tests/inspector_tests.rs
+++ b/cli/tests/inspector_tests.rs
@@ -12,6 +12,7 @@ use std::io::BufRead;
 use std::pin::Pin;
 use test_util as util;
 use tokio::net::TcpStream;
+use util::http_server;
 
 mod inspector {
   use super::*;
@@ -1133,4 +1134,177 @@ mod inspector {
     child.kill().unwrap();
     child.wait().unwrap();
   }
+
+  #[tokio::test]
+  async fn inspector_break_on_first_line_npm_esm() {
+    let _server = http_server();
+
+    let mut child = util::deno_cmd()
+      .arg("run")
+      .arg("--quiet")
+      .arg(inspect_flag_with_unique_port("--inspect-brk"))
+      .arg("npm:@denotest/bin/cli-esm")
+      .arg("this")
+      .arg("is")
+      .arg("a")
+      .arg("test")
+      .envs(util::env_vars_for_npm_tests())
+      .stdout(std::process::Stdio::piped())
+      .stderr(std::process::Stdio::piped())
+      .spawn()
+      .unwrap();
+
+    let stderr = child.stderr.as_mut().unwrap();
+    let mut stderr_lines =
+      std::io::BufReader::new(stderr).lines().map(|r| r.unwrap());
+    let ws_url = extract_ws_url_from_stderr(&mut stderr_lines);
+
+    let (socket, response) =
+      tokio_tungstenite::connect_async(ws_url).await.unwrap();
+    assert_eq!(response.status(), 101); // Switching protocols.
+
+    let (mut socket_tx, socket_rx) = socket.split();
+    let mut socket_rx = socket_rx
+      .map(|msg| msg.unwrap().to_string())
+      .filter(|msg| {
+        let pass = !msg.starts_with(r#"{"method":"Debugger.scriptParsed","#);
+        futures::future::ready(pass)
+      })
+      .boxed_local();
+
+    let stdout = child.stdout.as_mut().unwrap();
+    let mut stdout_lines =
+      std::io::BufReader::new(stdout).lines().map(|r| r.unwrap());
+
+    assert_stderr_for_inspect_brk(&mut stderr_lines);
+
+    assert_inspector_messages(
+      &mut socket_tx,
+      &[
+        r#"{"id":1,"method":"Runtime.enable"}"#,
+        r#"{"id":2,"method":"Debugger.enable"}"#,
+      ],
+      &mut socket_rx,
+      &[
+        r#"{"id":1,"result":{}}"#,
+        r#"{"id":2,"result":{"debuggerId":"#,
+      ],
+      &[
+        r#"{"method":"Runtime.executionContextCreated","params":{"context":{"id":1,"#,
+      ],
+    )
+    .await;
+
+    assert_inspector_messages(
+      &mut socket_tx,
+      &[r#"{"id":3,"method":"Runtime.runIfWaitingForDebugger"}"#],
+      &mut socket_rx,
+      &[r#"{"id":3,"result":{}}"#],
+      &[r#"{"method":"Debugger.paused","#],
+    )
+    .await;
+
+    assert_inspector_messages(
+      &mut socket_tx,
+      &[r#"{"id":4,"method":"Debugger.resume"}"#],
+      &mut socket_rx,
+      &[r#"{"id":4,"result":{}}"#],
+      &[],
+    )
+    .await;
+
+    assert_eq!(&stdout_lines.next().unwrap(), "this");
+    assert_eq!(&stdout_lines.next().unwrap(), "is");
+    assert_eq!(&stdout_lines.next().unwrap(), "a");
+    assert_eq!(&stdout_lines.next().unwrap(), "test");
+
+    child.kill().unwrap();
+    child.wait().unwrap();
+  }
+
+  #[tokio::test]
+  async fn inspector_break_on_first_line_npm_cjs() {
+    let _server = http_server();
+    let mut child = util::deno_cmd()
+      .arg("run")
+      .arg("--quiet")
+      .arg(inspect_flag_with_unique_port("--inspect-brk"))
+      .arg("npm:@denotest/bin/cli-cjs")
+      .arg("this")
+      .arg("is")
+      .arg("a")
+      .arg("test")
+      .envs(util::env_vars_for_npm_tests())
+      .stdout(std::process::Stdio::piped())
+      .stderr(std::process::Stdio::piped())
+      .spawn()
+      .unwrap();
+
+    let stderr = child.stderr.as_mut().unwrap();
+    let mut stderr_lines =
+      std::io::BufReader::new(stderr).lines().map(|r| r.unwrap());
+    let ws_url = extract_ws_url_from_stderr(&mut stderr_lines);
+
+    let (socket, response) =
+      tokio_tungstenite::connect_async(ws_url).await.unwrap();
+    assert_eq!(response.status(), 101); // Switching protocols.
+
+    let (mut socket_tx, socket_rx) = socket.split();
+    let mut socket_rx = socket_rx
+      .map(|msg| msg.unwrap().to_string())
+      .filter(|msg| {
+        let pass = !msg.starts_with(r#"{"method":"Debugger.scriptParsed","#);
+        futures::future::ready(pass)
+      })
+      .boxed_local();
+
+    let stdout = child.stdout.as_mut().unwrap();
+    let mut stdout_lines =
+      std::io::BufReader::new(stdout).lines().map(|r| r.unwrap());
+
+    assert_stderr_for_inspect_brk(&mut stderr_lines);
+
+    assert_inspector_messages(
+      &mut socket_tx,
+      &[
+        r#"{"id":1,"method":"Runtime.enable"}"#,
+        r#"{"id":2,"method":"Debugger.enable"}"#,
+      ],
+      &mut socket_rx,
+      &[
+        r#"{"id":1,"result":{}}"#,
+        r#"{"id":2,"result":{"debuggerId":"#,
+      ],
+      &[
+        r#"{"method":"Runtime.executionContextCreated","params":{"context":{"id":1,"#,
+      ],
+    )
+    .await;
+
+    assert_inspector_messages(
+      &mut socket_tx,
+      &[r#"{"id":3,"method":"Runtime.runIfWaitingForDebugger"}"#],
+      &mut socket_rx,
+      &[r#"{"id":3,"result":{}}"#],
+      &[r#"{"method":"Debugger.paused","#],
+    )
+    .await;
+
+    assert_inspector_messages(
+      &mut socket_tx,
+      &[r#"{"id":4,"method":"Debugger.resume"}"#],
+      &mut socket_rx,
+      &[r#"{"id":4,"result":{}}"#],
+      &[],
+    )
+    .await;
+
+    assert_eq!(&stdout_lines.next().unwrap(), "this");
+    assert_eq!(&stdout_lines.next().unwrap(), "is");
+    assert_eq!(&stdout_lines.next().unwrap(), "a");
+    assert_eq!(&stdout_lines.next().unwrap(), "test");
+
+    child.kill().unwrap();
+    child.wait().unwrap();
+  }
 }
diff --git a/cli/tests/npm_tests.rs b/cli/tests/npm_tests.rs
index 3939ee7bec..9c53fdeac4 100644
--- a/cli/tests/npm_tests.rs
+++ b/cli/tests/npm_tests.rs
@@ -8,6 +8,8 @@ mod npm {
   use std::process::Stdio;
   use test_util as util;
   use util::assert_contains;
+  use util::env_vars_for_npm_tests;
+  use util::env_vars_for_npm_tests_no_sync_download;
   use util::http_server;
 
   // NOTE: See how to make test npm packages at ./testdata/npm/README.md
@@ -15,7 +17,7 @@ mod npm {
   itest!(esm_module {
     args: "run --allow-read --allow-env npm/esm/main.js",
     output: "npm/esm/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
@@ -25,56 +27,56 @@ mod npm {
     "import chalk from 'npm:chalk@5'; console.log(chalk.green('chalk esm loads'));",
   ],
   output: "npm/esm/main.out",
-  envs: env_vars(),
+  envs: env_vars_for_npm_tests(),
   http_server: true,
 });
 
   itest!(esm_module_deno_test {
     args: "test --allow-read --allow-env --unstable npm/esm/test.js",
     output: "npm/esm/test.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(esm_import_cjs_default {
   args: "run --allow-read --allow-env --unstable --quiet --check=all npm/esm_import_cjs_default/main.ts",
   output: "npm/esm_import_cjs_default/main.out",
-  envs: env_vars(),
+  envs: env_vars_for_npm_tests(),
   http_server: true,
 });
 
   itest!(cjs_with_deps {
     args: "run --allow-read --allow-env npm/cjs_with_deps/main.js",
     output: "npm/cjs_with_deps/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(cjs_sub_path {
     args: "run --allow-read npm/cjs_sub_path/main.js",
     output: "npm/cjs_sub_path/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(cjs_local_global_decls {
     args: "run --allow-read npm/cjs_local_global_decls/main.ts",
     output: "npm/cjs_local_global_decls/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(cjs_reexport_collision {
     args: "run -A --quiet npm/cjs_reexport_collision/main.ts",
     output: "npm/cjs_reexport_collision/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(cjs_this_in_exports {
     args: "run --allow-read --quiet npm/cjs_this_in_exports/main.js",
     output: "npm/cjs_this_in_exports/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
     exit_code: 1,
   });
@@ -82,49 +84,49 @@ mod npm {
   itest!(translate_cjs_to_esm {
     args: "run -A --quiet npm/translate_cjs_to_esm/main.js",
     output: "npm/translate_cjs_to_esm/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(compare_globals {
     args: "run --allow-read --unstable --check=all npm/compare_globals/main.ts",
     output: "npm/compare_globals/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(conditional_exports {
     args: "run --allow-read npm/conditional_exports/main.js",
     output: "npm/conditional_exports/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(dual_cjs_esm {
     args: "run -A --quiet npm/dual_cjs_esm/main.ts",
     output: "npm/dual_cjs_esm/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(child_process_fork_test {
     args: "run -A --quiet npm/child_process_fork_test/main.ts",
     output: "npm/child_process_fork_test/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(cjs_module_export_assignment {
   args: "run -A --unstable --quiet --check=all npm/cjs_module_export_assignment/main.ts",
   output: "npm/cjs_module_export_assignment/main.out",
-  envs: env_vars(),
+  envs: env_vars_for_npm_tests(),
   http_server: true,
 });
 
   itest!(cjs_module_export_assignment_number {
   args: "run -A --unstable --quiet --check=all npm/cjs_module_export_assignment_number/main.ts",
   output: "npm/cjs_module_export_assignment_number/main.out",
-  envs: env_vars(),
+  envs: env_vars_for_npm_tests(),
   http_server: true,
 });
 
@@ -132,7 +134,7 @@ mod npm {
     args: "run npm/mixed_case_package_name/global.ts",
     output: "npm/mixed_case_package_name/global.out",
     exit_code: 0,
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
@@ -141,7 +143,7 @@ mod npm {
       "run --node-modules-dir -A $TESTDATA/npm/mixed_case_package_name/local.ts",
     output: "npm/mixed_case_package_name/local.out",
     exit_code: 0,
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
     temp_cwd: true,
   });
@@ -151,21 +153,21 @@ mod npm {
   // itest!(dynamic_import {
   //   args: "run --allow-read --allow-env npm/dynamic_import/main.ts",
   //   output: "npm/dynamic_import/main.out",
-  //   envs: env_vars(),
+  //   envs: env_vars_for_npm_tests(),
   //   http_server: true,
   // });
 
   itest!(dynamic_import_reload_same_package {
     args: "run -A --reload npm/dynamic_import_reload_same_package/main.ts",
     output: "npm/dynamic_import_reload_same_package/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(env_var_re_export_dev {
     args: "run --allow-read --allow-env --quiet npm/env_var_re_export/main.js",
     output_str: Some("dev\n"),
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
@@ -173,7 +175,7 @@ mod npm {
     args: "run --allow-read --allow-env --quiet npm/env_var_re_export/main.js",
     output_str: Some("prod\n"),
     envs: {
-      let mut vars = env_vars();
+      let mut vars = env_vars_for_npm_tests();
       vars.push(("NODE_ENV".to_string(), "production".to_string()));
       vars
     },
@@ -183,21 +185,21 @@ mod npm {
   itest!(cached_only {
     args: "run --cached-only npm/cached_only/main.ts",
     output: "npm/cached_only/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     exit_code: 1,
   });
 
   itest!(import_map {
   args: "run --allow-read --allow-env --import-map npm/import_map/import_map.json npm/import_map/main.js",
   output: "npm/import_map/main.out",
-  envs: env_vars(),
+  envs: env_vars_for_npm_tests(),
   http_server: true,
 });
 
   itest!(lock_file {
   args: "run --allow-read --allow-env --lock npm/lock_file/lock.json npm/lock_file/main.js",
   output: "npm/lock_file/main.out",
-  envs: env_vars(),
+  envs: env_vars_for_npm_tests(),
   http_server: true,
   exit_code: 10,
 });
@@ -205,14 +207,14 @@ mod npm {
   itest!(sub_paths {
     args: "run -A --quiet npm/sub_paths/main.jsx",
     output: "npm/sub_paths/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(remote_npm_specifier {
     args: "run --quiet npm/remote_npm_specifier/main.ts",
     output: "npm/remote_npm_specifier/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
     exit_code: 1,
   });
@@ -220,14 +222,14 @@ mod npm {
   itest!(tarball_with_global_header {
     args: "run -A --quiet npm/tarball_with_global_header/main.js",
     output: "npm/tarball_with_global_header/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(nonexistent_file {
     args: "run -A --quiet npm/nonexistent_file/main.js",
     output: "npm/nonexistent_file/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
     exit_code: 1,
   });
@@ -235,21 +237,21 @@ mod npm {
   itest!(invalid_package_name {
     args: "run -A --quiet npm/invalid_package_name/main.js",
     output: "npm/invalid_package_name/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     exit_code: 1,
   });
 
   itest!(require_json {
     args: "run -A --quiet npm/require_json/main.js",
     output: "npm/require_json/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(error_version_after_subpath {
     args: "run -A --quiet npm/error_version_after_subpath/main.js",
     output: "npm/error_version_after_subpath/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
     exit_code: 1,
   });
@@ -257,14 +259,14 @@ mod npm {
   itest!(deno_cache {
     args: "cache --reload npm:chalk npm:mkdirp",
     output: "npm/deno_cache.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(check_all {
     args: "check --remote npm/check_errors/main.ts",
     output: "npm/check_errors/main_all.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
     exit_code: 1,
   });
@@ -272,7 +274,7 @@ mod npm {
   itest!(check_local {
     args: "check npm/check_errors/main.ts",
     output: "npm/check_errors/main_local.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
     exit_code: 1,
   });
@@ -280,7 +282,7 @@ mod npm {
   itest!(types {
     args: "check --quiet npm/types/main.ts",
     output: "npm/types/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
     exit_code: 1,
   });
@@ -288,7 +290,7 @@ mod npm {
   itest!(types_ambient_module {
     args: "check --quiet npm/types_ambient_module/main.ts",
     output: "npm/types_ambient_module/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
     exit_code: 1,
   });
@@ -296,7 +298,7 @@ mod npm {
   itest!(types_ambient_module_import_map {
   args: "check --quiet --import-map=npm/types_ambient_module/import_map.json npm/types_ambient_module/main_import_map.ts",
   output: "npm/types_ambient_module/main_import_map.out",
-  envs: env_vars(),
+  envs: env_vars_for_npm_tests(),
   http_server: true,
   exit_code: 1,
 });
@@ -305,14 +307,14 @@ mod npm {
     args: "run --check --unstable npm/no_types_in_conditional_exports/main.ts",
     output: "npm/no_types_in_conditional_exports/main.out",
     exit_code: 0,
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(types_entry_value_not_exists {
     args: "run --check=all npm/types_entry_value_not_exists/main.ts",
     output: "npm/types_entry_value_not_exists/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
     exit_code: 0,
   });
@@ -320,7 +322,7 @@ mod npm {
   itest!(types_no_types_entry {
     args: "run --check=all npm/types_no_types_entry/main.ts",
     output: "npm/types_no_types_entry/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
     exit_code: 0,
   });
@@ -328,7 +330,7 @@ mod npm {
   itest!(typescript_file_in_package {
     args: "run npm/typescript_file_in_package/main.ts",
     output: "npm/typescript_file_in_package/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
     exit_code: 1,
   });
@@ -345,7 +347,7 @@ mod npm {
       ],
       None,
       // don't use the sync env var
-      Some(env_vars_no_sync_download()),
+      Some(env_vars_for_npm_tests_no_sync_download()),
       true,
     );
     assert!(out.contains("chalk cjs loads"));
@@ -364,7 +366,7 @@ mod npm {
       .arg("--allow-env")
       .arg("npm/cached_only_after_first_run/main1.ts")
       .env("NO_COLOR", "1")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -384,7 +386,7 @@ mod npm {
       .arg("--cached-only")
       .arg("npm/cached_only_after_first_run/main2.ts")
       .env("NO_COLOR", "1")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -407,7 +409,7 @@ mod npm {
       .arg("--cached-only")
       .arg("npm/cached_only_after_first_run/main1.ts")
       .env("NO_COLOR", "1")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -434,7 +436,7 @@ mod npm {
       .arg("--allow-env")
       .arg("npm/reload/main.ts")
       .env("NO_COLOR", "1")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -454,7 +456,7 @@ mod npm {
       .arg("--reload")
       .arg("npm/reload/main.ts")
       .env("NO_COLOR", "1")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -474,7 +476,7 @@ mod npm {
       .arg("--reload=npm:")
       .arg("npm/reload/main.ts")
       .env("NO_COLOR", "1")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -494,7 +496,7 @@ mod npm {
       .arg("--reload=npm:chalk")
       .arg("npm/reload/main.ts")
       .env("NO_COLOR", "1")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -514,7 +516,7 @@ mod npm {
       .arg("--reload=npm:foobar")
       .arg("npm/reload/main.ts")
       .env("NO_COLOR", "1")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -541,7 +543,7 @@ mod npm {
       .arg("--no-npm")
       .arg("npm/no_npm_after_first_run/main1.ts")
       .env("NO_COLOR", "1")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -563,7 +565,7 @@ mod npm {
       .arg("--allow-env")
       .arg("npm/no_npm_after_first_run/main1.ts")
       .env("NO_COLOR", "1")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -583,7 +585,7 @@ mod npm {
       .arg("--no-npm")
       .arg("npm/no_npm_after_first_run/main1.ts")
       .env("NO_COLOR", "1")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -614,7 +616,7 @@ mod npm {
       .arg("npm:mkdirp@1.0.4")
       .arg("test_dir")
       .env("NO_COLOR", "1")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .spawn()
       .unwrap();
     let output = deno.wait_with_output().unwrap();
@@ -626,49 +628,49 @@ mod npm {
   itest!(deno_run_cowsay {
     args: "run -A --quiet npm:cowsay@1.5.0 Hello",
     output: "npm/deno_run_cowsay.out",
-    envs: env_vars_no_sync_download(),
+    envs: env_vars_for_npm_tests_no_sync_download(),
     http_server: true,
   });
 
   itest!(deno_run_cowsay_explicit {
     args: "run -A --quiet npm:cowsay@1.5.0/cowsay Hello",
     output: "npm/deno_run_cowsay.out",
-    envs: env_vars_no_sync_download(),
+    envs: env_vars_for_npm_tests_no_sync_download(),
     http_server: true,
   });
 
   itest!(deno_run_cowthink {
     args: "run -A --quiet npm:cowsay@1.5.0/cowthink Hello",
     output: "npm/deno_run_cowthink.out",
-    envs: env_vars_no_sync_download(),
+    envs: env_vars_for_npm_tests_no_sync_download(),
     http_server: true,
   });
 
   itest!(deno_run_bin_esm {
     args: "run -A --quiet npm:@denotest/bin/cli-esm this is a test",
     output: "npm/deno_run_esm.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(deno_run_bin_no_ext {
     args: "run -A --quiet npm:@denotest/bin/cli-no-ext this is a test",
     output: "npm/deno_run_no_ext.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(deno_run_bin_cjs {
     args: "run -A --quiet npm:@denotest/bin/cli-cjs this is a test",
     output: "npm/deno_run_cjs.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
   itest!(deno_run_non_existent {
     args: "run npm:mkdirp@0.5.125",
     output: "npm/deno_run_non_existent.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
     exit_code: 1,
   });
@@ -676,7 +678,7 @@ mod npm {
   itest!(builtin_module_module {
     args: "run --allow-read --quiet npm/builtin_module_module/main.js",
     output: "npm/builtin_module_module/main.out",
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
@@ -684,7 +686,7 @@ mod npm {
   args:
     "run --node-modules-dir -A --quiet $TESTDATA/npm/require_added_nm_folder/main.js",
   output: "npm/require_added_nm_folder/main.out",
-  envs: env_vars(),
+  envs: env_vars_for_npm_tests(),
   http_server: true,
   exit_code: 0,
   temp_cwd: true,
@@ -693,7 +695,7 @@ mod npm {
   itest!(node_modules_dir_with_deps {
   args: "run --allow-read --allow-env --node-modules-dir $TESTDATA/npm/cjs_with_deps/main.js",
   output: "npm/cjs_with_deps/main.out",
-  envs: env_vars(),
+  envs: env_vars_for_npm_tests(),
   http_server: true,
   temp_cwd: true,
 });
@@ -701,7 +703,7 @@ mod npm {
   itest!(node_modules_dir_yargs {
   args: "run --allow-read --allow-env --node-modules-dir $TESTDATA/npm/cjs_yargs/main.js",
   output: "npm/cjs_yargs/main.out",
-  envs: env_vars(),
+  envs: env_vars_for_npm_tests(),
   http_server: true,
   temp_cwd: true,
 });
@@ -718,7 +720,7 @@ mod npm {
       .arg("--node-modules-dir")
       .arg("--quiet")
       .arg(util::testdata_path().join("npm/dual_cjs_esm/main.ts"))
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .spawn()
       .unwrap();
     let output = deno.wait_with_output().unwrap();
@@ -754,7 +756,7 @@ mod npm {
       .arg("--quiet")
       .arg("-A")
       .arg(util::testdata_path().join("npm/dual_cjs_esm/main.ts"))
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .spawn()
       .unwrap();
     let output = deno.wait_with_output().unwrap();
@@ -792,7 +794,7 @@ mod npm {
   args: "compile -A --quiet npm/cached_only/main.ts",
   output_str: Some("error: npm specifiers have not yet been implemented for this sub command (https://github.com/denoland/deno/issues/15960). Found: npm:chalk@5\n"),
   exit_code: 1,
-  envs: env_vars(),
+  envs: env_vars_for_npm_tests(),
   http_server: true,
 });
 
@@ -800,7 +802,7 @@ mod npm {
   args: "bundle --quiet npm/esm/main.js",
   output_str: Some("error: npm specifiers have not yet been implemented for this sub command (https://github.com/denoland/deno/issues/15960). Found: npm:chalk@5\n"),
   exit_code: 1,
-  envs: env_vars(),
+  envs: env_vars_for_npm_tests(),
   http_server: true,
 });
 
@@ -808,7 +810,7 @@ mod npm {
     args: "info --quiet npm/cjs_with_deps/main.js",
     output: "npm/cjs_with_deps/main_info.out",
     exit_code: 0,
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
@@ -816,7 +818,7 @@ mod npm {
     args: "info --quiet --node-modules-dir $TESTDATA/npm/cjs_with_deps/main.js",
     output: "npm/cjs_with_deps/main_info.out",
     exit_code: 0,
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
     temp_cwd: true,
   });
@@ -825,7 +827,7 @@ mod npm {
     args: "info --quiet --json npm/cjs_with_deps/main.js",
     output: "npm/cjs_with_deps/main_info_json.out",
     exit_code: 0,
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
@@ -834,7 +836,7 @@ mod npm {
     "info --quiet --node-modules-dir --json $TESTDATA/npm/cjs_with_deps/main.js",
   output: "npm/cjs_with_deps/main_info_json.out",
   exit_code: 0,
-  envs: env_vars(),
+  envs: env_vars_for_npm_tests(),
   http_server: true,
   temp_cwd: true,
 });
@@ -843,7 +845,7 @@ mod npm {
     args: "info --quiet npm:chalk@4",
     output: "npm/info/chalk.out",
     exit_code: 0,
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
@@ -851,7 +853,7 @@ mod npm {
     args: "info --quiet --json npm:chalk@4",
     output: "npm/info/chalk_json.out",
     exit_code: 0,
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
@@ -1054,7 +1056,7 @@ mod npm {
       .arg("deno.lock")
       .arg("-A")
       .arg("main.ts")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -1270,7 +1272,7 @@ mod npm {
       .arg("--lock-write")
       .arg("--quiet")
       .arg("npm:cowsay@1.5.0")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -1322,7 +1324,7 @@ mod npm {
       .arg("-A")
       .arg("npm:@denotest/bin/cli-esm")
       .arg("test")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -1358,7 +1360,7 @@ mod npm {
       .arg("run")
       .arg("-A")
       .arg("main.ts")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -1389,7 +1391,7 @@ mod npm {
       .arg("run")
       .arg("-A")
       .arg("main.ts")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -1404,7 +1406,7 @@ mod npm {
       .arg("--reload")
       .arg("-A")
       .arg("main.ts")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -1420,7 +1422,7 @@ mod npm {
       .arg("--node-modules-dir")
       .arg("-A")
       .arg("main.ts")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -1444,7 +1446,7 @@ mod npm {
       .arg("--node-modules-dir")
       .arg("-A")
       .arg("main.ts")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -1461,7 +1463,7 @@ mod npm {
       .arg("--reload")
       .arg("-A")
       .arg("main.ts")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -1479,7 +1481,7 @@ mod npm {
       .arg("--reload")
       .arg("-A")
       .arg("main.ts")
-      .envs(env_vars())
+      .envs(env_vars_for_npm_tests())
       .stdout(Stdio::piped())
       .stderr(Stdio::piped())
       .spawn()
@@ -1493,7 +1495,7 @@ mod npm {
     args: "info --quiet npm/peer_deps_with_copied_folders/main.ts",
     output: "npm/peer_deps_with_copied_folders/main_info.out",
     exit_code: 0,
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
@@ -1501,7 +1503,7 @@ mod npm {
     args: "info --quiet --json npm/peer_deps_with_copied_folders/main.ts",
     output: "npm/peer_deps_with_copied_folders/main_info_json.out",
     exit_code: 0,
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
 
@@ -1509,25 +1511,7 @@ mod npm {
     args: "run --reload npm/create_require/main.ts",
     output: "npm/create_require/main.out",
     exit_code: 0,
-    envs: env_vars(),
+    envs: env_vars_for_npm_tests(),
     http_server: true,
   });
-
-  fn env_vars_no_sync_download() -> Vec<(String, String)> {
-    vec![
-      ("DENO_NODE_COMPAT_URL".to_string(), util::std_file_url()),
-      ("DENO_NPM_REGISTRY".to_string(), util::npm_registry_url()),
-      ("NO_COLOR".to_string(), "1".to_string()),
-    ]
-  }
-
-  fn env_vars() -> Vec<(String, String)> {
-    let mut env_vars = env_vars_no_sync_download();
-    env_vars.push((
-      // make downloads determinstic
-      "DENO_UNSTABLE_NPM_SYNC_DOWNLOAD".to_string(),
-      "1".to_string(),
-    ));
-    env_vars
-  }
 }
diff --git a/cli/worker.rs b/cli/worker.rs
index fb021b614c..ad7b4e8ed2 100644
--- a/cli/worker.rs
+++ b/cli/worker.rs
@@ -70,6 +70,7 @@ impl CliMainWorker {
         &mut self.worker.js_runtime,
         &self.main_module.to_file_path().unwrap().to_string_lossy(),
         true,
+        self.ps.options.inspect_brk().is_some(),
       )?;
     } else {
       self.execute_main_module_possibly_with_npm().await?;
diff --git a/ext/node/02_require.js b/ext/node/02_require.js
index 372cc84719..db43299117 100644
--- a/ext/node/02_require.js
+++ b/ext/node/02_require.js
@@ -69,6 +69,8 @@
   let statCache = null;
   let isPreloading = false;
   let mainModule = null;
+  let hasBrokenOnInspectBrk = false;
+  let hasInspectBrk = false;
 
   function stat(filename) {
     // TODO: required only on windows
@@ -723,6 +725,12 @@
     if (requireDepth === 0) {
       statCache = new SafeMap();
     }
+
+    if (hasInspectBrk && !hasBrokenOnInspectBrk) {
+      hasBrokenOnInspectBrk = true;
+      core.ops.op_require_break_on_next_statement();
+    }
+
     const result = compiledWrapper.call(
       thisValue,
       exports,
@@ -896,6 +904,9 @@
   window.__bootstrap.internals = {
     ...window.__bootstrap.internals ?? {},
     require: {
+      setInspectBrk() {
+        hasInspectBrk = true;
+      },
       Module,
       wrapSafe,
       toRealPath,
diff --git a/ext/node/lib.rs b/ext/node/lib.rs
index d69d3b6fe5..0e84cea7bb 100644
--- a/ext/node/lib.rs
+++ b/ext/node/lib.rs
@@ -7,6 +7,7 @@ use deno_core::normalize_path;
 use deno_core::op;
 use deno_core::url::Url;
 use deno_core::Extension;
+use deno_core::JsRuntimeInspector;
 use deno_core::OpState;
 use once_cell::sync::Lazy;
 use std::collections::HashSet;
@@ -31,6 +32,7 @@ pub use resolution::path_to_declaration_path;
 pub use resolution::NodeModuleKind;
 pub use resolution::DEFAULT_CONDITIONS;
 pub use resolution::TYPES_CONDITIONS;
+use std::cell::RefCell;
 
 pub trait NodePermissions {
   fn check_read(&mut self, path: &Path) -> Result<(), AnyError>;
@@ -106,6 +108,7 @@ pub fn init<P: NodePermissions + 'static>(
       op_require_read_closest_package_json::decl::<P>(),
       op_require_read_package_scope::decl(),
       op_require_package_imports_resolve::decl::<P>(),
+      op_require_break_on_next_statement::decl(),
     ])
     .state(move |state| {
       if let Some(npm_resolver) = maybe_npm_resolver.clone() {
@@ -630,3 +633,11 @@ where
     Ok(None)
   }
 }
+
+#[op]
+fn op_require_break_on_next_statement(state: &mut OpState) {
+  let inspector = state.borrow::<Rc<RefCell<JsRuntimeInspector>>>();
+  inspector
+    .borrow_mut()
+    .wait_for_session_and_break_on_next_statement()
+}
diff --git a/runtime/web_worker.rs b/runtime/web_worker.rs
index 89f0bd6c22..ee47d0d990 100644
--- a/runtime/web_worker.rs
+++ b/runtime/web_worker.rs
@@ -473,6 +473,12 @@ impl WebWorker {
         &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 967d53ea82..01498e1f62 100644
--- a/runtime/worker.rs
+++ b/runtime/worker.rs
@@ -250,6 +250,12 @@ impl MainWorker {
         &mut js_runtime,
         options.should_break_on_first_statement,
       );
+
+      // 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);
     }
 
     Self {
diff --git a/test_util/src/lib.rs b/test_util/src/lib.rs
index 3b23af7364..b1b14c0040 100644
--- a/test_util/src/lib.rs
+++ b/test_util/src/lib.rs
@@ -94,6 +94,24 @@ lazy_static! {
   static ref GUARD: Mutex<HttpServerCount> = Mutex::new(HttpServerCount::default());
 }
 
+pub fn env_vars_for_npm_tests_no_sync_download() -> Vec<(String, String)> {
+  vec![
+    ("DENO_NODE_COMPAT_URL".to_string(), std_file_url()),
+    ("DENO_NPM_REGISTRY".to_string(), npm_registry_url()),
+    ("NO_COLOR".to_string(), "1".to_string()),
+  ]
+}
+
+pub fn env_vars_for_npm_tests() -> Vec<(String, String)> {
+  let mut env_vars = env_vars_for_npm_tests_no_sync_download();
+  env_vars.push((
+    // make downloads determinstic
+    "DENO_UNSTABLE_NPM_SYNC_DOWNLOAD".to_string(),
+    "1".to_string(),
+  ));
+  env_vars
+}
+
 pub fn root_path() -> PathBuf {
   PathBuf::from(concat!(env!("CARGO_MANIFEST_DIR")))
     .parent()