diff --git a/lib/internal/modules/cjs/loader.js b/lib/internal/modules/cjs/loader.js
index 22e77d8bff70c0..418f672e34c24e 100644
--- a/lib/internal/modules/cjs/loader.js
+++ b/lib/internal/modules/cjs/loader.js
@@ -1308,9 +1308,9 @@ function wrapSafe(filename, content, cjsModuleInstance, codeCache) {
     );
 
     // Cache the source map for the module if present.
-    const { sourceMapURL } = script;
+    const { sourceMapURL, sourceURL } = script;
     if (sourceMapURL) {
-      maybeCacheSourceMap(filename, content, this, false, undefined, sourceMapURL);
+      maybeCacheSourceMap(filename, content, this, false, sourceURL, sourceMapURL);
     }
 
     return {
@@ -1332,7 +1332,7 @@ function wrapSafe(filename, content, cjsModuleInstance, codeCache) {
 
     // Cache the source map for the module if present.
     if (result.sourceMapURL) {
-      maybeCacheSourceMap(filename, content, this, false, undefined, result.sourceMapURL);
+      maybeCacheSourceMap(filename, content, this, false, result.sourceURL, result.sourceMapURL);
     }
 
     return result;
diff --git a/lib/internal/modules/esm/loader.js b/lib/internal/modules/esm/loader.js
index 85c4960c8e3b11..a5fa374936353c 100644
--- a/lib/internal/modules/esm/loader.js
+++ b/lib/internal/modules/esm/loader.js
@@ -280,7 +280,7 @@ class ModuleLoader {
     const wrap = new ModuleWrap(url, undefined, source, 0, 0);
     // Cache the source map for the module if present.
     if (wrap.sourceMapURL) {
-      maybeCacheSourceMap(url, source, null, false, undefined, wrap.sourceMapURL);
+      maybeCacheSourceMap(url, source, null, false, wrap.sourceURL, wrap.sourceMapURL);
     }
     const { registerModule } = require('internal/modules/esm/utils');
     // TODO(joyeecheung): refactor so that the default options are shared across
diff --git a/lib/internal/modules/esm/translators.js b/lib/internal/modules/esm/translators.js
index 7312bd0b09f41a..1552d1ef6f841d 100644
--- a/lib/internal/modules/esm/translators.js
+++ b/lib/internal/modules/esm/translators.js
@@ -177,7 +177,7 @@ translators.set('module', function moduleStrategy(url, source, isMain) {
   const module = new ModuleWrap(url, undefined, source, 0, 0);
   // Cache the source map for the module if present.
   if (module.sourceMapURL) {
-    maybeCacheSourceMap(url, source, null, false, undefined, module.sourceMapURL);
+    maybeCacheSourceMap(url, source, null, false, module.sourceURL, module.sourceMapURL);
   }
   const { registerModule } = require('internal/modules/esm/utils');
   registerModule(module, {
@@ -227,7 +227,7 @@ function loadCJSModule(module, source, url, filename) {
   }
   // Cache the source map for the cjs module if present.
   if (compileResult.sourceMapURL) {
-    maybeCacheSourceMap(url, source, null, false, undefined, compileResult.sourceMapURL);
+    maybeCacheSourceMap(url, source, null, false, compileResult.sourceURL, compileResult.sourceMapURL);
   }
 
   const compiledWrapper = compileResult.function;
diff --git a/lib/internal/source_map/source_map_cache.js b/lib/internal/source_map/source_map_cache.js
index 53c3374fc09176..25fe56e6c38926 100644
--- a/lib/internal/source_map/source_map_cache.js
+++ b/lib/internal/source_map/source_map_cache.js
@@ -123,10 +123,10 @@ function maybeCacheSourceMap(filename, content, cjsModuleInstance, isGeneratedSo
     return;
   }
 
-  // FIXME: callers should obtain sourceURL from v8 and pass it
-  // rather than leaving it undefined and extract by regex.
-  if (sourceURL === undefined) {
-    sourceURL = extractSourceURLMagicComment(content);
+  if (sourceURL !== undefined) {
+    // SourceURL magic comment content might be a file path or URL.
+    // Normalize the sourceURL to be a file URL if it is a file path.
+    sourceURL = normalizeReferrerURL(sourceURL);
   }
 
   const data = dataFromUrl(filename, sourceMapURL);
@@ -149,9 +149,6 @@ function maybeCacheSourceMap(filename, content, cjsModuleInstance, isGeneratedSo
       sourceURL,
     };
     generatedSourceMapCache.set(filename, entry);
-    if (sourceURL) {
-      generatedSourceMapCache.set(sourceURL, entry);
-    }
   } else {
     // If there is no cjsModuleInstance and is not generated source assume we are in a
     // "modules/esm" context.
@@ -178,7 +175,7 @@ function maybeCacheGeneratedSourceMap(content) {
     return;
   }
   try {
-    maybeCacheSourceMap(sourceURL, content, null, true, sourceURL);
+    maybeCacheSourceMap(sourceURL, content, null, true);
   } catch (err) {
     // This can happen if the filename is not a valid URL.
     // If we fail to cache the source map, we should not fail the whole process.
diff --git a/lib/internal/vm.js b/lib/internal/vm.js
index 0b9865ea9a0cf6..cc0cdd54ed7414 100644
--- a/lib/internal/vm.js
+++ b/lib/internal/vm.js
@@ -25,6 +25,7 @@ const {
 const {
   getOptionValue,
 } = require('internal/options');
+const { maybeCacheSourceMap } = require('internal/source_map/source_map_cache');
 const {
   privateSymbols: {
     contextify_context_private_symbol,
@@ -151,6 +152,7 @@ function internalCompileFunction(
   }
 
   registerImportModuleDynamically(result.function, importModuleDynamically);
+  maybeCacheSourceMap(filename, code, result.function, false, result.sourceURL, result.sourceMapURL);
 
   return result;
 }
diff --git a/lib/internal/vm/module.js b/lib/internal/vm/module.js
index cd4f3a65f8466c..b8ae4e10bda33a 100644
--- a/lib/internal/vm/module.js
+++ b/lib/internal/vm/module.js
@@ -77,6 +77,7 @@ const kPerContextModuleId = Symbol('kPerContextModuleId');
 const kLink = Symbol('kLink');
 
 const { isContext } = require('internal/vm');
+const { maybeCacheSourceMap } = require('internal/source_map/source_map_cache');
 
 function isModule(object) {
   if (typeof object !== 'object' || object === null || !ObjectPrototypeHasOwnProperty(object, kWrap)) {
@@ -141,6 +142,7 @@ class Module {
           importModuleDynamicallyWrap(options.importModuleDynamically) :
           undefined,
       };
+      maybeCacheSourceMap(identifier, sourceText, this, false, this[kWrap].sourceURL, this[kWrap].sourceMapURL);
     } else {
       assert(syntheticEvaluationSteps);
       this[kWrap] = new ModuleWrap(identifier, context,
diff --git a/lib/vm.js b/lib/vm.js
index 34814c430d3253..138b2118eaa359 100644
--- a/lib/vm.js
+++ b/lib/vm.js
@@ -63,6 +63,7 @@ const {
   isContext: _isContext,
   registerImportModuleDynamically,
 } = require('internal/vm');
+const { maybeCacheSourceMap } = require('internal/source_map/source_map_cache');
 const {
   vm_dynamic_import_main_context_default,
 } = internalBinding('symbols');
@@ -126,6 +127,7 @@ class Script extends ContextifyScript {
     }
 
     registerImportModuleDynamically(this, importModuleDynamically);
+    maybeCacheSourceMap(filename, code, this, false, this.sourceURL, this.sourceMapURL);
   }
 
   runInThisContext(options) {
diff --git a/src/env_properties.h b/src/env_properties.h
index 05d8fcf576c51a..287e669012e2d8 100644
--- a/src/env_properties.h
+++ b/src/env_properties.h
@@ -300,6 +300,7 @@
   V(sni_context_string, "sni_context")                                         \
   V(source_string, "source")                                                   \
   V(source_map_url_string, "sourceMapURL")                                     \
+  V(source_url_string, "sourceURL")                                            \
   V(stack_string, "stack")                                                     \
   V(standard_name_string, "standardName")                                      \
   V(start_time_string, "startTime")                                            \
diff --git a/src/module_wrap.cc b/src/module_wrap.cc
index 92b34f5a8b99c2..b5f05a6b62dfc4 100644
--- a/src/module_wrap.cc
+++ b/src/module_wrap.cc
@@ -265,6 +265,13 @@ void ModuleWrap::New(const FunctionCallbackInfo<Value>& args) {
         return;
       }
 
+      if (that->Set(context,
+                    realm->env()->source_url_string(),
+                    module->GetUnboundModuleScript()->GetSourceURL())
+              .IsNothing()) {
+        return;
+      }
+
       if (that->Set(context,
                     realm->env()->source_map_url_string(),
                     module->GetUnboundModuleScript()->GetSourceMappingURL())
diff --git a/src/node_contextify.cc b/src/node_contextify.cc
index 0f94ea501cea64..f317b1301dd2fb 100644
--- a/src/node_contextify.cc
+++ b/src/node_contextify.cc
@@ -905,6 +905,13 @@ void ContextifyScript::New(const FunctionCallbackInfo<Value>& args) {
     return;
   }
 
+  if (args.This()
+          ->Set(env->context(),
+                env->source_url_string(),
+                v8_script->GetSourceURL())
+          .IsNothing())
+    return;
+
   if (args.This()
           ->Set(env->context(),
                 env->source_map_url_string(),
@@ -1373,6 +1380,15 @@ Local<Object> ContextifyContext::CompileFunctionAndCacheResult(
   Local<Object> result = Object::New(isolate);
   if (result->Set(parsing_context, env->function_string(), fn).IsNothing())
     return Object::New(env->isolate());
+
+  // ScriptOrigin::ResourceName() returns SourceURL magic comment content if
+  // present.
+  if (result
+          ->Set(parsing_context,
+                env->source_url_string(),
+                fn->GetScriptOrigin().ResourceName())
+          .IsNothing())
+    return Object::New(env->isolate());
   if (result
           ->Set(parsing_context,
                 env->source_map_url_string(),
@@ -1650,11 +1666,15 @@ static void CompileFunctionForCJSLoader(
   std::vector<Local<Name>> names = {
       env->cached_data_rejected_string(),
       env->source_map_url_string(),
+      env->source_url_string(),
       env->function_string(),
   };
   std::vector<Local<Value>> values = {
       Boolean::New(isolate, cache_rejected),
       fn->GetScriptOrigin().SourceMapUrl(),
+      // ScriptOrigin::ResourceName() returns SourceURL magic comment content if
+      // present.
+      fn->GetScriptOrigin().ResourceName(),
       fn,
   };
   Local<Object> result = Object::New(
diff --git a/src/node_errors.cc b/src/node_errors.cc
index ff091fd20d915b..4b560b8b4feffc 100644
--- a/src/node_errors.cc
+++ b/src/node_errors.cc
@@ -57,7 +57,20 @@ static std::string GetSourceMapErrorSource(Isolate* isolate,
                                            bool* added_exception_line) {
   v8::TryCatch try_catch(isolate);
   HandleScope handle_scope(isolate);
-  Environment* env = Environment::GetCurrent(context);
+  Realm* realm = Realm::GetCurrent(context);
+
+  Local<Function> get_source;
+  if (realm != nullptr) {
+    // If we are in a Realm, call the realm specific getSourceMapErrorSource
+    // callback to avoid passing the JS objects (the exception and trace) across
+    // the realm boundary.
+    get_source = realm->get_source_map_error_source();
+  } else {
+    Environment* env = Environment::GetCurrent(context);
+    // The context is created with ContextifyContext, call the principal
+    // realm's getSourceMapErrorSource callback.
+    get_source = env->principal_realm()->get_source_map_error_source();
+  }
 
   // The ScriptResourceName of the message may be different from the one we use
   // to compile the script. V8 replaces it when it detects magic comments in
@@ -69,8 +82,8 @@ static std::string GetSourceMapErrorSource(Isolate* isolate,
   Local<Value> argv[] = {script_resource_name,
                          v8::Int32::New(isolate, linenum),
                          v8::Int32::New(isolate, columnum)};
-  MaybeLocal<Value> maybe_ret = env->get_source_map_error_source()->Call(
-      context, Undefined(isolate), arraysize(argv), argv);
+  MaybeLocal<Value> maybe_ret =
+      get_source->Call(context, Undefined(isolate), arraysize(argv), argv);
   Local<Value> ret;
   if (!maybe_ret.ToLocal(&ret)) {
     // Ignore the caught exceptions.
diff --git a/test/common/assertSnapshot.js b/test/common/assertSnapshot.js
index 88f40281e069b7..cb3b9fd332b24b 100644
--- a/test/common/assertSnapshot.js
+++ b/test/common/assertSnapshot.js
@@ -8,6 +8,11 @@ const assert = require('node:assert/strict');
 const stackFramesRegexp = /(?<=\n)(\s+)((.+?)\s+\()?(?:\(?(.+?):(\d+)(?::(\d+))?)\)?(\s+\{)?(\[\d+m)?(\n|$)/g;
 const windowNewlineRegexp = /\r/g;
 
+function replaceExperimentalWarning(str) {
+  return str.replace(/\(node:\d+\) ExperimentalWarning: (.*)\n/g, '')
+    .replace('(Use `node --trace-warnings ...` to show where the warning was created)\n', '');
+}
+
 function replaceNodeVersion(str) {
   return str.replaceAll(process.version, '*');
 }
@@ -16,6 +21,10 @@ function replaceStackTrace(str, replacement = '$1*$7$8\n') {
   return str.replace(stackFramesRegexp, replacement);
 }
 
+function replaceInternalStackTrace(str) {
+  return str.replaceAll(/(\W+).*node:internal.*/g, '$1*');
+}
+
 function replaceWindowsLineEndings(str) {
   return str.replace(windowNewlineRegexp, '');
 }
@@ -24,8 +33,20 @@ function replaceWindowsPaths(str) {
   return common.isWindows ? str.replaceAll(path.win32.sep, path.posix.sep) : str;
 }
 
-function replaceFullPaths(str) {
-  return str.replaceAll(process.cwd(), '');
+function replaceWindowsDriveLetter(str) {
+  if (!common.isWindows) {
+    return str;
+  }
+  const currentDriveLetter = path.parse(process.cwd()).root.substring(0, 1).toLowerCase();
+  const regex = new RegExp(`${currentDriveLetter}:`, 'gi');
+  return str.replaceAll(regex, '');
+}
+
+function transformCwd(replacement = '') {
+  const cwd = process.cwd();
+  return (str) => {
+    return str.replaceAll(cwd, replacement);
+  };
 }
 
 function transform(...args) {
@@ -87,11 +108,14 @@ async function spawnAndAssert(filename, transform = (x) => x, { tty = false, ...
 module.exports = {
   assertSnapshot,
   getSnapshotPath,
-  replaceFullPaths,
+  replaceExperimentalWarning,
   replaceNodeVersion,
   replaceStackTrace,
+  replaceInternalStackTrace,
   replaceWindowsLineEndings,
   replaceWindowsPaths,
+  replaceWindowsDriveLetter,
   spawnAndAssert,
   transform,
+  transformCwd,
 };
diff --git a/test/fixtures/source-map/output/source_map_disabled_by_api.snapshot b/test/fixtures/source-map/output/source_map_disabled_by_api.snapshot
index 655cd6695e1116..f538904873393e 100644
--- a/test/fixtures/source-map/output/source_map_disabled_by_api.snapshot
+++ b/test/fixtures/source-map/output/source_map_disabled_by_api.snapshot
@@ -1,12 +1,12 @@
 Error: an error!
-    at functionD (*enclosing-call-site-min.js:1:156)
-    at functionC (*enclosing-call-site-min.js:1:97)
-    at functionB (*enclosing-call-site-min.js:1:60)
-    at functionA (*enclosing-call-site-min.js:1:26)
-    at Object.<anonymous> (*enclosing-call-site-min.js:1:199)
+    at functionD (*/test/fixtures/source-map/enclosing-call-site-min.js:1:156)
+    at functionC (*/test/fixtures/source-map/enclosing-call-site-min.js:1:97)
+    at functionB (*/test/fixtures/source-map/enclosing-call-site-min.js:1:60)
+    at functionA (*/test/fixtures/source-map/enclosing-call-site-min.js:1:26)
+    at Object.<anonymous> (*/test/fixtures/source-map/enclosing-call-site-min.js:1:199)
 Error: an error!
-    at functionD (*enclosing-call-site.js:16:17)
-    at functionC (*enclosing-call-site.js:10:3)
-    at functionB (*enclosing-call-site.js:6:3)
-    at functionA (*enclosing-call-site.js:2:3)
-    at Object.<anonymous> (*enclosing-call-site.js:24:3)
+    at functionD (*/test/fixtures/source-map/enclosing-call-site.js:16:17)
+    at functionC (*/test/fixtures/source-map/enclosing-call-site.js:10:3)
+    at functionB (*/test/fixtures/source-map/enclosing-call-site.js:6:3)
+    at functionA (*/test/fixtures/source-map/enclosing-call-site.js:2:3)
+    at Object.<anonymous> (*/test/fixtures/source-map/enclosing-call-site.js:24:3)
diff --git a/test/fixtures/source-map/output/source_map_enabled_by_api.snapshot b/test/fixtures/source-map/output/source_map_enabled_by_api.snapshot
index 082b3f310ed4f9..9fe43a29865b35 100644
--- a/test/fixtures/source-map/output/source_map_enabled_by_api.snapshot
+++ b/test/fixtures/source-map/output/source_map_enabled_by_api.snapshot
@@ -1,12 +1,12 @@
 Error: an error!
-    at functionD (*enclosing-call-site.js:16:17)
-    at functionC (*enclosing-call-site.js:10:3)
-    at functionB (*enclosing-call-site.js:6:3)
-    at functionA (*enclosing-call-site.js:2:3)
-    at Object.<anonymous> (*enclosing-call-site.js:24:3)
+    at functionD (*/test/fixtures/source-map/enclosing-call-site.js:16:17)
+    at functionC (*/test/fixtures/source-map/enclosing-call-site.js:10:3)
+    at functionB (*/test/fixtures/source-map/enclosing-call-site.js:6:3)
+    at functionA (*/test/fixtures/source-map/enclosing-call-site.js:2:3)
+    at Object.<anonymous> (*/test/fixtures/source-map/enclosing-call-site.js:24:3)
 Error: an error!
-    at functionD (*enclosing-call-site-min.js:1:156)
-    at functionC (*enclosing-call-site-min.js:1:97)
-    at functionB (*enclosing-call-site-min.js:1:60)
-    at functionA (*enclosing-call-site-min.js:1:26)
-    at Object.<anonymous> (*enclosing-call-site-min.js:1:199)
+    at functionD (*/test/fixtures/source-map/enclosing-call-site-min.js:1:156)
+    at functionC (*/test/fixtures/source-map/enclosing-call-site-min.js:1:97)
+    at functionB (*/test/fixtures/source-map/enclosing-call-site-min.js:1:60)
+    at functionA (*/test/fixtures/source-map/enclosing-call-site-min.js:1:26)
+    at Object.<anonymous> (*/test/fixtures/source-map/enclosing-call-site-min.js:1:199)
diff --git a/test/fixtures/source-map/output/source_map_enclosing_function.snapshot b/test/fixtures/source-map/output/source_map_enclosing_function.snapshot
index 976cd4fdbbc6e9..b60f988be3214e 100644
--- a/test/fixtures/source-map/output/source_map_enclosing_function.snapshot
+++ b/test/fixtures/source-map/output/source_map_enclosing_function.snapshot
@@ -1,13 +1,13 @@
-*enclosing-call-site.js:26
+*/test/fixtures/source-map/enclosing-call-site.js:26
   throw err
   ^
 
 
 Error: an error!
-    at functionD (*enclosing-call-site.js:16:17)
-    at functionC (*enclosing-call-site.js:10:3)
-    at functionB (*enclosing-call-site.js:6:3)
-    at functionA (*enclosing-call-site.js:2:3)
-    at Object.<anonymous> (*enclosing-call-site.js:24:3)
+    at functionD (*/test/fixtures/source-map/enclosing-call-site.js:16:17)
+    at functionC (*/test/fixtures/source-map/enclosing-call-site.js:10:3)
+    at functionB (*/test/fixtures/source-map/enclosing-call-site.js:6:3)
+    at functionA (*/test/fixtures/source-map/enclosing-call-site.js:2:3)
+    at Object.<anonymous> (*/test/fixtures/source-map/enclosing-call-site.js:24:3)
 
 Node.js *
diff --git a/test/fixtures/source-map/output/source_map_eval.js b/test/fixtures/source-map/output/source_map_eval.js
index 5492c179248180..5270de68826103 100644
--- a/test/fixtures/source-map/output/source_map_eval.js
+++ b/test/fixtures/source-map/output/source_map_eval.js
@@ -7,4 +7,5 @@ Error.stackTraceLimit = 3;
 const fs = require('fs');
 
 const content = fs.readFileSync(require.resolve('../tabs.js'), 'utf8');
+// SourceURL magic comment is hardcoded in the source content.
 eval(content);
diff --git a/test/fixtures/source-map/output/source_map_eval.snapshot b/test/fixtures/source-map/output/source_map_eval.snapshot
index a4fcdb25282dfa..87afb545b56636 100644
--- a/test/fixtures/source-map/output/source_map_eval.snapshot
+++ b/test/fixtures/source-map/output/source_map_eval.snapshot
@@ -1,11 +1,11 @@
-*tabs.coffee:26
+/synthethized/workspace/tabs.coffee:26
 	alert "I knew it!"
 	^
 
 
 ReferenceError: alert is not defined
-    at Object.eval (*tabs.coffee:26:2)
-    at eval (*tabs.coffee:1:14)
-    at Object.<anonymous> (*output*source_map_eval.js:10:1)
+    at Object.eval (/synthethized/workspace/tabs.coffee:26:2)
+    at eval (/synthethized/workspace/tabs.coffee:1:14)
+    at Object.<anonymous> (*/test/fixtures/source-map/output/source_map_eval.js:11:1)
 
 Node.js *
diff --git a/test/fixtures/source-map/output/source_map_no_source_file.snapshot b/test/fixtures/source-map/output/source_map_no_source_file.snapshot
index cf9329747ba692..6d0e0cf6db727e 100644
--- a/test/fixtures/source-map/output/source_map_no_source_file.snapshot
+++ b/test/fixtures/source-map/output/source_map_no_source_file.snapshot
@@ -1,9 +1,9 @@
-*no-source.js:2
+*/test/fixtures/source-map/no-source.js:2
     throw new Error('foo');
     ^
 
 Error: foo
-    at Throw (*file-not-exists.ts:2:9)
-    at Object.<anonymous> (*file-not-exists.ts:5:1)
+    at Throw (*/test/fixtures/source-map/file-not-exists.ts:2:9)
+    at Object.<anonymous> (*/test/fixtures/source-map/file-not-exists.ts:5:1)
 
 Node.js *
diff --git a/test/fixtures/source-map/output/source_map_prepare_stack_trace.snapshot b/test/fixtures/source-map/output/source_map_prepare_stack_trace.snapshot
index 9e9740a26fc34e..57bac36a2e5214 100644
--- a/test/fixtures/source-map/output/source_map_prepare_stack_trace.snapshot
+++ b/test/fixtures/source-map/output/source_map_prepare_stack_trace.snapshot
@@ -1,10 +1,10 @@
 Error: an error!
-    at functionD (*enclosing-call-site.js:16:17)
-    at functionB (*enclosing-call-site.js:6:3)
-    at functionA (*enclosing-call-site.js:2:3)
-    at Object.<anonymous> (*enclosing-call-site.js:24:3)
+    at functionD (*/test/fixtures/source-map/enclosing-call-site.js:16:17)
+    at functionB (*/test/fixtures/source-map/enclosing-call-site.js:6:3)
+    at functionA (*/test/fixtures/source-map/enclosing-call-site.js:2:3)
+    at Object.<anonymous> (*/test/fixtures/source-map/enclosing-call-site.js:24:3)
 Error: an error!
-    at functionD (*enclosing-call-site-min.js:1:156)
-    at functionB (*enclosing-call-site-min.js:1:60)
-    at functionA (*enclosing-call-site-min.js:1:26)
-    at Object.<anonymous> (*enclosing-call-site-min.js:1:199)
+    at functionD (*/test/fixtures/source-map/enclosing-call-site-min.js:1:156)
+    at functionB (*/test/fixtures/source-map/enclosing-call-site-min.js:1:60)
+    at functionA (*/test/fixtures/source-map/enclosing-call-site-min.js:1:26)
+    at Object.<anonymous> (*/test/fixtures/source-map/enclosing-call-site-min.js:1:199)
diff --git a/test/fixtures/source-map/output/source_map_reference_error_tabs.snapshot b/test/fixtures/source-map/output/source_map_reference_error_tabs.snapshot
index 97d02f176c0cb7..2043bd0a88e897 100644
--- a/test/fixtures/source-map/output/source_map_reference_error_tabs.snapshot
+++ b/test/fixtures/source-map/output/source_map_reference_error_tabs.snapshot
@@ -1,10 +1,10 @@
-*tabs.coffee:26
+*/test/fixtures/source-map/tabs.coffee:26
 	alert "I knew it!"
 	^
 
 
 ReferenceError: alert is not defined
-    at Object.<anonymous> (*tabs.coffee:26:2)
-    at Object.<anonymous> (*tabs.coffee:1:14)
+    at Object.<anonymous> (*/test/fixtures/source-map/tabs.coffee:26:2)
+    at Object.<anonymous> (*/test/fixtures/source-map/tabs.coffee:1:14)
 
 Node.js *
diff --git a/test/fixtures/source-map/output/source_map_sourcemapping_url_string.snapshot b/test/fixtures/source-map/output/source_map_sourcemapping_url_string.snapshot
index 6a109c904e1155..52d4e6a28ee5ce 100644
--- a/test/fixtures/source-map/output/source_map_sourcemapping_url_string.snapshot
+++ b/test/fixtures/source-map/output/source_map_sourcemapping_url_string.snapshot
@@ -1,3 +1,3 @@
 Error: an exception.
-    at Object.<anonymous> (*typescript-sourcemapping_url_string.ts:3:7)
+    at Object.<anonymous> (*/test/fixtures/source-map/typescript-sourcemapping_url_string.ts:3:7)
     *
diff --git a/test/fixtures/source-map/output/source_map_throw_catch.snapshot b/test/fixtures/source-map/output/source_map_throw_catch.snapshot
index 5eaffbfbf7874f..6e80e500c8cf17 100644
--- a/test/fixtures/source-map/output/source_map_throw_catch.snapshot
+++ b/test/fixtures/source-map/output/source_map_throw_catch.snapshot
@@ -1,4 +1,4 @@
 reachable
 Error: an exception
-    at branch (*typescript-throw.ts:18:11)
-    at Object.<anonymous> (*typescript-throw.ts:24:1)
+    at branch (*/test/fixtures/source-map/typescript-throw.ts:18:11)
+    at Object.<anonymous> (*/test/fixtures/source-map/typescript-throw.ts:24:1)
diff --git a/test/fixtures/source-map/output/source_map_throw_first_tick.snapshot b/test/fixtures/source-map/output/source_map_throw_first_tick.snapshot
index fba8c95cc1103f..e129d73ef1581c 100644
--- a/test/fixtures/source-map/output/source_map_throw_first_tick.snapshot
+++ b/test/fixtures/source-map/output/source_map_throw_first_tick.snapshot
@@ -1,11 +1,11 @@
 reachable
-*typescript-throw.ts:18
+*/test/fixtures/source-map/typescript-throw.ts:18
     throw Error('an exception');
     ^
 
 
 Error: an exception
-    at branch (*typescript-throw.ts:18:11)
-    at Object.<anonymous> (*typescript-throw.ts:24:1)
+    at branch (*/test/fixtures/source-map/typescript-throw.ts:18:11)
+    at Object.<anonymous> (*/test/fixtures/source-map/typescript-throw.ts:24:1)
 
 Node.js *
diff --git a/test/fixtures/source-map/output/source_map_throw_icu.snapshot b/test/fixtures/source-map/output/source_map_throw_icu.snapshot
index 425495062e6423..4b2853479b9576 100644
--- a/test/fixtures/source-map/output/source_map_throw_icu.snapshot
+++ b/test/fixtures/source-map/output/source_map_throw_icu.snapshot
@@ -1,10 +1,10 @@
-*icu.jsx:3
+*/test/fixtures/source-map/icu.jsx:3
     ("あ 🐕 🐕", throw Error("an error"));
      ^
 
 
 Error: an error
-    at Object.createElement (*icu.jsx:3:23)
-    at Object.<anonymous> (*icu.jsx:9:5)
+    at Object.createElement (*/test/fixtures/source-map/icu.jsx:3:23)
+    at Object.<anonymous> (*/test/fixtures/source-map/icu.jsx:9:5)
 
 Node.js *
diff --git a/test/fixtures/source-map/output/source_map_throw_set_immediate.snapshot b/test/fixtures/source-map/output/source_map_throw_set_immediate.snapshot
index e5054d01b8f91b..4cf4d52a16ea93 100644
--- a/test/fixtures/source-map/output/source_map_throw_set_immediate.snapshot
+++ b/test/fixtures/source-map/output/source_map_throw_set_immediate.snapshot
@@ -1,11 +1,11 @@
-*uglify-throw-original.js:5
+*/test/fixtures/source-map/uglify-throw-original.js:5
   throw Error('goodbye');
   ^
 
 
 Error: goodbye
-    at Hello (*uglify-throw-original.js:5:9)
-    at Immediate.<anonymous> (*uglify-throw-original.js:9:3)
-    at process.processImmediate (node:internal*timers:478:21)
+    at Hello (*/test/fixtures/source-map/uglify-throw-original.js:5:9)
+    at Immediate.<anonymous> (*/test/fixtures/source-map/uglify-throw-original.js:9:3)
+    *
 
 Node.js *
diff --git a/test/fixtures/source-map/output/source_map_vm_function.js b/test/fixtures/source-map/output/source_map_vm_function.js
new file mode 100644
index 00000000000000..01fe273f0b34dd
--- /dev/null
+++ b/test/fixtures/source-map/output/source_map_vm_function.js
@@ -0,0 +1,18 @@
+// Flags:  --enable-source-maps
+
+'use strict';
+require('../../../common');
+const vm = require('vm');
+
+const fs = require('fs');
+const filename = require.resolve('../tabs.js');
+const content = fs.readFileSync(filename, 'utf8');
+
+const context = vm.createContext({});
+vm.runInContext('Error.stackTraceLimit = 3', context);
+
+const fn = vm.compileFunction(content, [], {
+  filename,
+  parsingContext: context,
+})
+fn();
diff --git a/test/fixtures/source-map/output/source_map_vm_function.snapshot b/test/fixtures/source-map/output/source_map_vm_function.snapshot
new file mode 100644
index 00000000000000..6a5d3bb7d64b2a
--- /dev/null
+++ b/test/fixtures/source-map/output/source_map_vm_function.snapshot
@@ -0,0 +1,11 @@
+*/test/fixtures/source-map/tabs.coffee:26
+	alert "I knew it!"
+	^
+
+
+ReferenceError: alert is not defined
+    at <anonymous> (*/test/fixtures/source-map/tabs.coffee:26:2)
+    at <anonymous> (*/test/fixtures/source-map/tabs.coffee:1:14)
+    at Object.<anonymous> (*/test/fixtures/source-map/output/source_map_vm_function.js:18:1)
+
+Node.js *
diff --git a/test/fixtures/source-map/output/source_map_vm_module.js b/test/fixtures/source-map/output/source_map_vm_module.js
new file mode 100644
index 00000000000000..117e31bd03b856
--- /dev/null
+++ b/test/fixtures/source-map/output/source_map_vm_module.js
@@ -0,0 +1,22 @@
+// Flags:  --enable-source-maps --experimental-vm-modules
+
+'use strict';
+const common = require('../../../common');
+const vm = require('vm');
+Error.stackTraceLimit = 3;
+
+const fs = require('fs');
+const filename = require.resolve('../tabs.js');
+const content = fs.readFileSync(filename, 'utf8');
+
+const context = vm.createContext({});
+vm.runInContext('Error.stackTraceLimit = 3', context);
+
+(async () => {
+  const mod = new vm.SourceTextModule(content, {
+    context,
+    identifier: filename,
+  });
+  await mod.link(common.mustNotCall());
+  await mod.evaluate();
+})();
diff --git a/test/fixtures/source-map/output/source_map_vm_module.snapshot b/test/fixtures/source-map/output/source_map_vm_module.snapshot
new file mode 100644
index 00000000000000..76c8a437116fba
--- /dev/null
+++ b/test/fixtures/source-map/output/source_map_vm_module.snapshot
@@ -0,0 +1,11 @@
+*/test/fixtures/source-map/tabs.coffee:26
+	alert "I knew it!"
+	^
+
+
+ReferenceError: alert is not defined
+    at <anonymous> (*/test/fixtures/source-map/tabs.coffee:26:2)
+    at <anonymous> (*/test/fixtures/source-map/tabs.coffee:1:14)
+    *
+
+Node.js *
diff --git a/test/fixtures/source-map/output/source_map_vm_script.js b/test/fixtures/source-map/output/source_map_vm_script.js
new file mode 100644
index 00000000000000..f6eff3282c0294
--- /dev/null
+++ b/test/fixtures/source-map/output/source_map_vm_script.js
@@ -0,0 +1,28 @@
+// Flags:  --enable-source-maps
+
+'use strict';
+require('../../../common');
+const vm = require('vm');
+Error.stackTraceLimit = 3;
+
+const fs = require('fs');
+const filename = require.resolve('../tabs.js');
+const content = fs.readFileSync(filename, 'utf8');
+
+const context = vm.createContext({});
+vm.runInContext('Error.stackTraceLimit = 3', context);
+
+// Scripts created implicitly with `vm.runInContext`.
+try {
+  vm.runInContext(content, context, {
+    filename,
+  });
+} catch (e) {
+  console.error(e);
+}
+
+// Scripts created explicitly with `vm.Script`.
+const script = new vm.Script(content, {
+  filename,
+});
+script.runInContext(context);
diff --git a/test/fixtures/source-map/output/source_map_vm_script.snapshot b/test/fixtures/source-map/output/source_map_vm_script.snapshot
new file mode 100644
index 00000000000000..dfce0837dfb7ea
--- /dev/null
+++ b/test/fixtures/source-map/output/source_map_vm_script.snapshot
@@ -0,0 +1,20 @@
+*/test/fixtures/source-map/tabs.coffee:26
+	alert "I knew it!"
+	^
+
+
+ReferenceError: alert is not defined
+    at <anonymous> (*/test/fixtures/source-map/tabs.coffee:26:2)
+    at <anonymous> (*/test/fixtures/source-map/tabs.coffee:1:14)
+    at Script.runInContext (node:vm:150:12)
+*/test/fixtures/source-map/tabs.coffee:26
+	alert "I knew it!"
+	^
+
+
+ReferenceError: alert is not defined
+    at <anonymous> (*/test/fixtures/source-map/tabs.coffee:26:2)
+    at <anonymous> (*/test/fixtures/source-map/tabs.coffee:1:14)
+    at Script.runInContext (node:vm:150:12)
+
+Node.js *
diff --git a/test/fixtures/source-map/tabs.coffee b/test/fixtures/source-map/tabs.coffee
index abc5baab636e8a..dd03beeedf4ee8 100644
--- a/test/fixtures/source-map/tabs.coffee
+++ b/test/fixtures/source-map/tabs.coffee
@@ -27,3 +27,8 @@ if true
 
 # Array comprehensions:
 cubes = (math.cube num for num in list)
+
+# To reproduce:
+# cd test/fixtures/source-map
+# npx --package=coffeescript@2.5.1 -- coffee -M --compile tabs.coffee
+# sed -i -e "s/$(pwd | sed -e "s/\//\\\\\//g")/\\/synthethized\\/workspace/g" tabs.js
diff --git a/test/fixtures/source-map/tabs.js b/test/fixtures/source-map/tabs.js
index 4e8ebf149dfd16..c13ea80a74922f 100644
--- a/test/fixtures/source-map/tabs.js
+++ b/test/fixtures/source-map/tabs.js
@@ -50,7 +50,12 @@
     return results;
   })();
 
+  // To reproduce:
+// cd test/fixtures/source-map
+// npx --package=coffeescript@2.5.1 -- coffee -M --compile tabs.coffee
+// sed -i -e "s/$(pwd | sed -e "s/\//\\\\\//g")/\\/synthethized\\/workspace/g" tabs.js
+
 }).call(this);
 
-//# sourceMappingURL=data:application/json;base64,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
-//# sourceURL=/Users/bencoe/oss/coffee-script-test/tabs.coffee
+//# sourceMappingURL=data:application/json;base64,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
+//# sourceURL=/synthethized/workspace/tabs.coffee
\ No newline at end of file
diff --git a/test/parallel/test-node-output-sourcemaps.mjs b/test/parallel/test-node-output-sourcemaps.mjs
index d82f4a249cd1d9..64a33f71795232 100644
--- a/test/parallel/test-node-output-sourcemaps.mjs
+++ b/test/parallel/test-node-output-sourcemaps.mjs
@@ -1,29 +1,20 @@
-import * as common from '../common/index.mjs';
+import '../common/index.mjs';
 import * as fixtures from '../common/fixtures.mjs';
 import * as snapshot from '../common/assertSnapshot.js';
-import * as path from 'node:path';
 import { describe, it } from 'node:test';
 
 describe('sourcemaps output', { concurrency: !process.env.TEST_PARALLEL }, () => {
-  function normalize(str) {
-    const result = str
-    .replaceAll(snapshot.replaceWindowsPaths(process.cwd()), '')
-    .replaceAll('//', '*')
-    .replaceAll('/Users/bencoe/oss/coffee-script-test', '')
-    .replaceAll(/\/(\w)/g, '*$1')
-    .replaceAll('*test*', '*')
-    .replaceAll('*fixtures*source-map*', '*')
-    .replaceAll(/(\W+).*node:internal\*modules.*/g, '$1*');
-    if (common.isWindows) {
-      const currentDeviceLetter = path.parse(process.cwd()).root.substring(0, 1).toLowerCase();
-      const regex = new RegExp(`${currentDeviceLetter}:/?`, 'gi');
-      return result.replaceAll(regex, '');
-    }
-    return result;
-  }
   const defaultTransform = snapshot
-    .transform(snapshot.replaceWindowsLineEndings, snapshot.replaceWindowsPaths,
-               normalize, snapshot.replaceNodeVersion);
+    .transform(
+      snapshot.replaceWindowsLineEndings,
+      snapshot.transformCwd('*'),
+      snapshot.replaceWindowsPaths,
+      // Remove drive letters from synthethized paths (i.e. not cwd).
+      snapshot.replaceWindowsDriveLetter,
+      snapshot.replaceInternalStackTrace,
+      snapshot.replaceExperimentalWarning,
+      snapshot.replaceNodeVersion
+    );
 
   const tests = [
     { name: 'source-map/output/source_map_disabled_by_api.js' },
@@ -38,6 +29,9 @@ describe('sourcemaps output', { concurrency: !process.env.TEST_PARALLEL }, () =>
     { name: 'source-map/output/source_map_throw_first_tick.js' },
     { name: 'source-map/output/source_map_throw_icu.js' },
     { name: 'source-map/output/source_map_throw_set_immediate.js' },
+    { name: 'source-map/output/source_map_vm_function.js' },
+    { name: 'source-map/output/source_map_vm_module.js' },
+    { name: 'source-map/output/source_map_vm_script.js' },
   ];
   for (const { name, transform } of tests) {
     it(name, async () => {
diff --git a/test/parallel/test-runner-output.mjs b/test/parallel/test-runner-output.mjs
index abc3d7c97b4879..1d371264e64deb 100644
--- a/test/parallel/test-runner-output.mjs
+++ b/test/parallel/test-runner-output.mjs
@@ -61,7 +61,7 @@ const defaultTransform = snapshot.transform(
   snapshot.replaceWindowsLineEndings,
   snapshot.replaceStackTrace,
   removeWindowsPathEscaping,
-  snapshot.replaceFullPaths,
+  snapshot.transformCwd(),
   snapshot.replaceWindowsPaths,
   replaceTestDuration,
   replaceTestLocationLine,
@@ -79,7 +79,7 @@ const junitTransform = snapshot.transform(
 const lcovTransform = snapshot.transform(
   snapshot.replaceWindowsLineEndings,
   snapshot.replaceStackTrace,
-  snapshot.replaceFullPaths,
+  snapshot.transformCwd(),
   snapshot.replaceWindowsPaths,
   pickTestFileFromLcov
 );