diff --git a/lib/internal/modules/cjs/loader.js b/lib/internal/modules/cjs/loader.js
index 827655bedb65bf..b8e0f98aea9e60 100644
--- a/lib/internal/modules/cjs/loader.js
+++ b/lib/internal/modules/cjs/loader.js
@@ -1872,9 +1872,20 @@ function loadSource(mod, filename, formatFromNode) {
 }
 
 function reconstructErrorStack(err, parentPath, parentSource) {
-  const errLine = StringPrototypeSplit(
-    StringPrototypeSlice(err.stack, StringPrototypeIndexOf(
-      err.stack, '    at ')), '\n', 1)[0];
+  // Find the stack frame that matches the parent module path.
+  // We cannot simply use the first frame because internal wrappers
+  // like TracingChannel.traceSync may appear before the user's frame.
+  const stackLines = StringPrototypeSplit(err.stack, '\n');
+  let errLine;
+  for (let i = 0; i < stackLines.length; i++) {
+    if (StringPrototypeIndexOf(stackLines[i], parentPath) !== -1) {
+      errLine = stackLines[i];
+      break;
+    }
+  }
+  if (errLine === undefined) {
+    return;
+  }
   const { 1: line, 2: col } =
     RegExpPrototypeExec(/(\d+):(\d+)\)/, errLine) || [];
   if (line && col) {
@@ -1910,7 +1921,6 @@ function getRequireESMError(mod, pkg, content, filename) {
       // Continue regardless of error.
     }
     if (parentSource) {
-      // TODO(joyeecheung): trim off internal frames from the stack.
       reconstructErrorStack(err, parentPath, parentSource);
     }
   }
diff --git a/test/es-module/test-cjs-esm-error-annotation.js b/test/es-module/test-cjs-esm-error-annotation.js
new file mode 100644
index 00000000000000..1fb6dfaae867ea
--- /dev/null
+++ b/test/es-module/test-cjs-esm-error-annotation.js
@@ -0,0 +1,50 @@
+'use strict';
+
+// This test verifies that when a CommonJS module requires an ES module,
+// the error annotation (arrow message) points to the user's require()
+// call in their source file, not to an internal frame such as
+// TracingChannel.traceSync in node:diagnostics_channel.
+// Regression test for https://github.com/nodejs/node/issues/55350.
+
+const { spawnPromisified } = require('../common');
+const fixtures = require('../common/fixtures.js');
+const assert = require('node:assert');
+const path = require('node:path');
+const { execPath } = require('node:process');
+const { describe, it } = require('node:test');
+
+const requiringEsm = path.resolve(
+  fixtures.path('/es-modules/cjs-esm-esm.js')
+);
+
+describe('ERR_REQUIRE_ESM error annotation', { concurrency: !process.env.TEST_PARALLEL }, () => {
+  it('should point to the user require() call, not internal frames', async () => {
+    const { code, stderr } = await spawnPromisified(execPath, [
+      '--no-experimental-require-module', requiringEsm,
+    ]);
+
+    assert.strictEqual(code, 1);
+
+    const stderrStr = stderr.replaceAll('\r', '');
+
+    // The error annotation should reference the user's file, not
+    // node:diagnostics_channel or any other internal module.
+    assert.ok(
+      stderrStr.includes(requiringEsm),
+      `Expected error output to reference ${requiringEsm}, got:\n${stderrStr}`
+    );
+
+    // The first line of the error output (before "Error [ERR_REQUIRE_ESM]")
+    // should contain the path to the requiring file, not "undefined".
+    const lines = stderrStr.split('\n');
+    const fileAnnotationLine = lines[0];
+    assert.ok(
+      fileAnnotationLine.includes(requiringEsm),
+      `First line should reference the requiring file, got: "${fileAnnotationLine}"`
+    );
+    assert.ok(
+      !fileAnnotationLine.includes('diagnostics_channel'),
+      `First line should not reference diagnostics_channel, got: "${fileAnnotationLine}"`
+    );
+  });
+});