diff --git a/lib/fs.js b/lib/fs.js
index 81c4d2b9c884..8df941d1731e 100644
--- a/lib/fs.js
+++ b/lib/fs.js
@@ -3178,13 +3178,22 @@ function unwatchFile(filename, listener) {
 
 
 let splitRoot;
+let getRealpathRootLstatPath;
 if (isWindows) {
   // Regex to find the device root on Windows (e.g. 'c:\\'), including trailing
   // slash.
   const splitRootRe = /^(?:[a-zA-Z]:|[\\/]{2}[^\\/]+[\\/][^\\/]+)?[\\/]*/;
+  const namespacedDriveRootRe = /^\\\\\?\\([a-zA-Z]:\\)$/;
   splitRoot = function splitRoot(str) {
     return SideEffectFreeRegExpPrototypeExec(splitRootRe, str)[0];
   };
+
+  // The root probe is the only use of this path. Passing a namespaced drive
+  // root to the binding would lose its trailing separator during resolution.
+  getRealpathRootLstatPath = function getRealpathRootLstatPath(path) {
+    const match = SideEffectFreeRegExpPrototypeExec(namespacedDriveRootRe, path);
+    return match === null ? path : match[1];
+  };
 } else {
   splitRoot = function splitRoot(str) {
     for (let i = 0; i < str.length; ++i) {
@@ -3193,6 +3202,7 @@ if (isWindows) {
     }
     return str;
   };
+
 }
 
 function encodeRealpathResult(result, options) {
@@ -3274,7 +3284,8 @@ function realpathSync(p, options) {
 
   // On windows, check that the root exists. On unix there is no need.
   if (isWindows) {
-    const out = binding.lstat(base, false, undefined, true /* throwIfNoEntry */);
+    const out = binding.lstat(
+      getRealpathRootLstatPath(base), false, undefined, true /* throwIfNoEntry */);
     if (out === undefined) {
       return;
     }
@@ -3359,7 +3370,8 @@ function realpathSync(p, options) {
 
     // On windows, check that the root exists. On unix there is no need.
     if (isWindows && !knownHard.has(base)) {
-      const out = binding.lstat(base, false, undefined, true /* throwIfNoEntry */);
+      const out = binding.lstat(
+        getRealpathRootLstatPath(base), false, undefined, true /* throwIfNoEntry */);
       if (out === undefined) {
         return;
       }
@@ -3443,7 +3455,7 @@ function realpath(p, options, callback) {
 
   // On windows, check that the root exists. On unix there is no need.
   if (isWindows && !knownHard.has(base)) {
-    fs.lstat(base, (err) => {
+    fs.lstat(getRealpathRootLstatPath(base), (err) => {
       if (err) return callback(err);
       knownHard.add(base);
       LOOP();
@@ -3532,7 +3544,7 @@ function realpath(p, options, callback) {
 
     // On windows, check that the root exists. On unix there is no need.
     if (isWindows && !knownHard.has(base)) {
-      fs.lstat(base, (err) => {
+      fs.lstat(getRealpathRootLstatPath(base), (err) => {
         if (err) return callback(err);
         knownHard.add(base);
         LOOP();
diff --git a/test/es-module/test-esm-long-path-win.js b/test/es-module/test-esm-long-path-win.js
index d125d341f092..d8aaabcca857 100644
--- a/test/es-module/test-esm-long-path-win.js
+++ b/test/es-module/test-esm-long-path-win.js
@@ -47,6 +47,24 @@ describe('long path on Windows', () => {
     tmpdir.refresh();
   });
 
+  it('runs an extended-length path as the entry point', async () => {
+    // The module loader resolves argv[1] through the JavaScript realpath
+    // implementation before executing it.
+    tmpdir.refresh();
+    const entry = tmpdir.resolve('extended-entry.js');
+    fs.writeFileSync(entry, 'console.log("hello world");');
+
+    const { code, signal, stderr, stdout } = await spawnPromisified(
+      execPath,
+      [path.toNamespacedPath(entry)],
+    );
+
+    assert.strictEqual(stderr, '');
+    assert.strictEqual(stdout.trim(), 'hello world');
+    assert.strictEqual(code, 0);
+    assert.strictEqual(signal, null);
+  });
+
   it('check long path in LegacyMainResolve - 1', () => {
     // Module layout will be the following:
     //  package.json
diff --git a/test/parallel/test-fs-realpath-namespaced-drive-win.js b/test/parallel/test-fs-realpath-namespaced-drive-win.js
new file mode 100644
index 000000000000..eac72eb8dfa2
--- /dev/null
+++ b/test/parallel/test-fs-realpath-namespaced-drive-win.js
@@ -0,0 +1,63 @@
+'use strict';
+
+const common = require('../common');
+if (!common.isWindows) {
+  common.skip('This test is Windows-specific.');
+}
+
+// Verify that the JavaScript realpath implementation accepts namespaced drive
+// paths, including when a junction switches the walk back to a regular drive
+// path, and reports a missing entry instead of treating the drive as a file.
+
+const assert = require('node:assert');
+const fs = require('node:fs');
+const path = require('node:path');
+const { test } = require('node:test');
+const tmpdir = require('../common/tmpdir');
+
+tmpdir.refresh();
+
+const entry = tmpdir.resolve('entry.js');
+const namespacedEntry = path.toNamespacedPath(entry);
+const namespacedMissing = path.toNamespacedPath(tmpdir.resolve('missing.js'));
+const targetDir = tmpdir.resolve('target');
+const targetEntry = path.join(targetDir, 'entry.js');
+const junctionDir = tmpdir.resolve('junction');
+const namespacedJunctionEntry = path.toNamespacedPath(
+  path.join(junctionDir, 'entry.js'),
+);
+
+fs.writeFileSync(entry, '');
+fs.mkdirSync(targetDir);
+fs.writeFileSync(targetEntry, '');
+fs.symlinkSync(targetDir, junctionDir, 'junction');
+
+function assertNamespacedRealpath(result) {
+  assert.strictEqual(path.toNamespacedPath(result), namespacedEntry);
+}
+
+test('fs.realpathSync resolves a namespaced drive path', () => {
+  assertNamespacedRealpath(fs.realpathSync(namespacedEntry));
+});
+
+test('fs.realpathSync reports ENOENT for a missing namespaced drive path', () => {
+  assert.throws(() => fs.realpathSync(namespacedMissing), { code: 'ENOENT' });
+});
+
+test('fs.realpathSync resolves a namespaced path through a junction', () => {
+  assert.strictEqual(fs.realpathSync(namespacedJunctionEntry), targetEntry);
+});
+
+test('fs.realpath resolves a namespaced drive path', (t, done) => {
+  fs.realpath(namespacedEntry, common.mustSucceed((result) => {
+    assertNamespacedRealpath(result);
+    done();
+  }));
+});
+
+test('fs.realpath resolves a namespaced path through a junction', (t, done) => {
+  fs.realpath(namespacedJunctionEntry, common.mustSucceed((result) => {
+    assert.strictEqual(result, targetEntry);
+    done();
+  }));
+});