diff --git a/lib/assert.js b/lib/assert.js
index 8ca9b211394ba8..89eebfa793fc39 100644
--- a/lib/assert.js
+++ b/lib/assert.js
@@ -65,6 +65,7 @@ const { isPromise, isRegExp } = require('internal/util/types');
 const { EOL } = require('internal/constants');
 const { NativeModule } = require('internal/bootstrap/loaders');
 const { isError } = require('internal/util');
+const { fileURLToPath } = require('internal/url');
 
 const errorCache = new SafeMap();
 const CallTracker = require('internal/assert/calltracker');
@@ -291,12 +292,18 @@ function getErrMessage(message, fn) {
   overrideStackTrace.set(err, (_, stack) => stack);
   const call = err.stack[0];
 
-  const filename = call.getFileName();
+  let filename = call.getFileName();
   const line = call.getLineNumber() - 1;
   let column = call.getColumnNumber() - 1;
   let identifier;
   let code;
 
+  if (filename && StringPrototypeStartsWith(filename, 'file:')) {
+    try {
+      filename = fileURLToPath(filename);
+    } catch {}
+  }
+
   if (filename) {
     identifier = `${filename}${line}${column}`;
 
diff --git a/lib/internal/modules/cjs/loader.js b/lib/internal/modules/cjs/loader.js
index 0c69d547d40b9a..7921cd237ed875 100644
--- a/lib/internal/modules/cjs/loader.js
+++ b/lib/internal/modules/cjs/loader.js
@@ -76,7 +76,12 @@ const {
   maybeCacheSourceMap,
   rekeySourceMap
 } = require('internal/source_map/source_map_cache');
-const { pathToFileURL, fileURLToPath, isURLInstance } = require('internal/url');
+const {
+  pathToFileURL,
+  fileURLToPath,
+  isURLInstance,
+  URL
+} = require('internal/url');
 const { deprecate } = require('internal/util');
 const vm = require('vm');
 const assert = require('internal/assert');
@@ -1005,12 +1010,18 @@ Module.prototype.require = function(id) {
 // (needed for setting breakpoint when called with --inspect-brk)
 let resolvedArgv;
 let hasPausedEntry = false;
+const absolutePathToUrlConverter = new URL('file://');
 
 function wrapSafe(filename, content, cjsModuleInstance) {
+  let filenameUrl = filename;
+  if (path.isAbsolute(filename)) {
+    absolutePathToUrlConverter.pathname = filename;
+    filenameUrl = absolutePathToUrlConverter.href;
+  }
   if (patched) {
     const wrapper = Module.wrap(content);
     return vm.runInThisContext(wrapper, {
-      filename,
+      filename: filenameUrl,
       lineOffset: 0,
       displayErrors: true,
       importModuleDynamically: async (specifier) => {
@@ -1023,7 +1034,7 @@ function wrapSafe(filename, content, cjsModuleInstance) {
   try {
     compiled = compileFunction(
       content,
-      filename,
+      filenameUrl,
       0,
       0,
       undefined,
diff --git a/lib/internal/source_map/prepare_stack_trace.js b/lib/internal/source_map/prepare_stack_trace.js
index c32f9780c2fb3f..3b16e536682688 100644
--- a/lib/internal/source_map/prepare_stack_trace.js
+++ b/lib/internal/source_map/prepare_stack_trace.js
@@ -85,10 +85,7 @@ const prepareStackTrace = (globalThis, error, trace) => {
           const prefix = (name && name !== t.getFunctionName()) ?
             `\n        -> at ${name}` :
             '\n        ->';
-          const originalSourceNoScheme =
-            StringPrototypeStartsWith(originalSource, 'file://') ?
-              fileURLToPath(originalSource) : originalSource;
-          str += `${prefix} (${originalSourceNoScheme}:${originalLine + 1}:` +
+          str += `${prefix} (${originalSource}:${originalLine + 1}:` +
             `${originalColumn + 1})`;
         }
       }
diff --git a/test/parallel/test-common-must-not-call.js b/test/parallel/test-common-must-not-call.js
index dcea7059dac7f5..936e4601efb824 100644
--- a/test/parallel/test-common-must-not-call.js
+++ b/test/parallel/test-common-must-not-call.js
@@ -4,6 +4,7 @@ const common = require('../common');
 const assert = require('assert');
 const path = require('path');
 const util = require('util');
+const { fileURLToPath } = require('url');
 
 const message = 'message';
 const testFunction1 = common.mustNotCall(message);
@@ -13,10 +14,15 @@ const testFunction2 = common.mustNotCall(message);
 const createValidate = (line, args = []) => common.mustCall((e) => {
   const prefix = `${message} at `;
   assert.ok(e.message.startsWith(prefix));
+  e.message = e.message.substring(prefix.length);
+  if (e.message.startsWith('file:')) {
+    const url = /.*/.exec(e.message)[0];
+    e.message = fileURLToPath(url) + e.message.substring(url.length);
+  }
   if (process.platform === 'win32') {
     e.message = e.message.substring(2); // remove 'C:'
   }
-  const msg = e.message.substring(prefix.length);
+  const msg = e.message;
   const firstColon = msg.indexOf(':');
   const fileName = msg.substring(0, firstColon);
   const rest = msg.substring(firstColon + 1);
@@ -26,14 +32,14 @@ const createValidate = (line, args = []) => common.mustCall((e) => {
   assert.strictEqual(rest, line + argsInfo);
 });
 
-const validate1 = createValidate('9');
+const validate1 = createValidate('10');
 try {
   testFunction1();
 } catch (e) {
   validate1(e);
 }
 
-const validate2 = createValidate('11', ['hello', 42]);
+const validate2 = createValidate('12', ['hello', 42]);
 try {
   testFunction2('hello', 42);
 } catch (e) {
diff --git a/test/parallel/test-domain-set-uncaught-exception-capture-after-load.js b/test/parallel/test-domain-set-uncaught-exception-capture-after-load.js
index 55e2e5368d7d17..0d95ff5fdf0166 100644
--- a/test/parallel/test-domain-set-uncaught-exception-capture-after-load.js
+++ b/test/parallel/test-domain-set-uncaught-exception-capture-after-load.js
@@ -1,6 +1,7 @@
 'use strict';
 const common = require('../common');
 const assert = require('assert');
+const { pathToFileURL } = require('url');
 
 (function foobar() {
   require('domain');
@@ -20,7 +21,7 @@ assert.throws(
     assert(err.stack.includes('-'.repeat(40)),
            `expected ${err.stack} to contain dashes`);
 
-    const location = `at foobar (${__filename}:`;
+    const location = `at foobar (${pathToFileURL(__filename)}:`;
     assert(err.stack.includes(location),
            `expected ${err.stack} to contain ${location}`);
     return true;
diff --git a/test/parallel/test-http-timeout-client-warning.js b/test/parallel/test-http-timeout-client-warning.js
index f11515b95fe340..0e062f0db6633a 100644
--- a/test/parallel/test-http-timeout-client-warning.js
+++ b/test/parallel/test-http-timeout-client-warning.js
@@ -2,12 +2,13 @@
 const common = require('../common');
 const http = require('http');
 const assert = require('assert');
+const { pathToFileURL } = require('url');
 
 // Checks that the setTimeout duration overflow warning is emitted
 // synchronously and therefore contains a meaningful stacktrace.
 
 process.on('warning', common.mustCall((warning) => {
-  assert(warning.stack.includes(__filename));
+  assert(warning.stack.includes(pathToFileURL(__filename)));
 }));
 
 const server = http.createServer((req, resp) => resp.end());
diff --git a/test/sequential/test-cli-syntax-bad.js b/test/sequential/test-cli-syntax-bad.js
index 8298157a57e16e..54bb9b81108b8c 100644
--- a/test/sequential/test-cli-syntax-bad.js
+++ b/test/sequential/test-cli-syntax-bad.js
@@ -3,6 +3,7 @@
 const common = require('../common');
 const assert = require('assert');
 const { exec } = require('child_process');
+const { pathToFileURL } = require('url');
 const fixtures = require('../common/fixtures');
 
 const node = process.execPath;
@@ -42,7 +43,8 @@ const syntaxErrorRE = /^SyntaxError: \b/m;
       assert(syntaxErrorRE.test(stderr), `${syntaxErrorRE} === ${stderr}`);
 
       // stderr should include the filename
-      assert(stderr.startsWith(file), `${stderr} starts with ${file}`);
+      assert(stderr.startsWith(pathToFileURL(file)),
+             `${stderr} starts with ${pathToFileURL(file)}`);
     }));
   });
 });
diff --git a/test/sequential/test-cli-syntax-require.js b/test/sequential/test-cli-syntax-require.js
index c309b1f4556c3f..92a6900db6b086 100644
--- a/test/sequential/test-cli-syntax-require.js
+++ b/test/sequential/test-cli-syntax-require.js
@@ -4,6 +4,7 @@ const common = require('../common');
 const assert = require('assert');
 const { exec } = require('child_process');
 const fixtures = require('../common/fixtures');
+const { pathToFileURL } = require('url');
 
 const node = process.execPath;
 
@@ -29,8 +30,9 @@ const syntaxErrorRE = /^SyntaxError: \b/m;
       // stderr should have a syntax error message
       assert(syntaxErrorRE.test(stderr), `${syntaxErrorRE} === ${stderr}`);
 
-      // stderr should include the filename
-      assert(stderr.startsWith(file), `${stderr} starts with ${file}`);
+      // stderr should include the file URL
+      const fileUrl = pathToFileURL(file);
+      assert(stderr.startsWith(fileUrl), `${stderr} starts with ${file}`);
     }));
   });
 });