diff --git a/pkgs/watcher/test/directory_watcher/shared.dart b/pkgs/watcher/test/directory_watcher/file_tests.dart
similarity index 99%
rename from pkgs/watcher/test/directory_watcher/shared.dart
rename to pkgs/watcher/test/directory_watcher/file_tests.dart
index 9a26a47a1..9b3fcd6c2 100644
--- a/pkgs/watcher/test/directory_watcher/shared.dart
+++ b/pkgs/watcher/test/directory_watcher/file_tests.dart
@@ -1,6 +1,7 @@
 // Copyright (c) 2012, the Dart project authors.  Please see the AUTHORS file
 // for details. All rights reserved. Use of this source code is governed by a
 // BSD-style license that can be found in the LICENSE file.
+
 import 'dart:io' as io;
 import 'dart:isolate';
 
@@ -10,7 +11,7 @@ import 'package:watcher/src/utils.dart';
 
 import '../utils.dart';
 
-void sharedTests() {
+void fileTests() {
   test('does not notify for files that already exist when started', () async {
     // Make some pre-existing files.
     writeFile('a.txt');
diff --git a/pkgs/watcher/test/directory_watcher/link_tests.dart b/pkgs/watcher/test/directory_watcher/link_tests.dart
new file mode 100644
index 000000000..f4919d1fb
--- /dev/null
+++ b/pkgs/watcher/test/directory_watcher/link_tests.dart
@@ -0,0 +1,268 @@
+// Copyright (c) 2025, the Dart project authors.  Please see the AUTHORS file
+// for details. All rights reserved. Use of this source code is governed by a
+// BSD-style license that can be found in the LICENSE file.
+
+import 'dart:io';
+
+import 'package:test/test.dart';
+
+import '../utils.dart';
+
+void linkTests({required bool isNative}) {
+  test('notifies when a link is added', () async {
+    createDir('targets');
+    createDir('links');
+    writeFile('targets/a.target');
+    await startWatcher(path: 'links');
+
+    writeLink(link: 'links/a.link', target: 'targets/a.target');
+
+    await expectAddEvent('links/a.link');
+  });
+
+  test(
+      'notifies when a link is replaced with a link to a different target '
+      'with the same contents', () async {
+    createDir('targets');
+    createDir('links');
+    writeFile('targets/a.target');
+    writeFile('targets/b.target');
+    writeLink(link: 'links/a.link', target: 'targets/a.target');
+    await startWatcher(path: 'links');
+
+    deleteLink('links/a.link');
+    writeLink(link: 'links/a.link', target: 'targets/b.target');
+
+    await expectModifyEvent('links/a.link');
+  });
+
+  test(
+      'notifies when a link is replaced with a link to a different target '
+      'with different contents', () async {
+    writeFile('targets/a.target', contents: 'a');
+    writeFile('targets/b.target', contents: 'b');
+    writeLink(link: 'links/a.link', target: 'targets/a.target');
+    await startWatcher(path: 'links');
+
+    deleteLink('links/a.link');
+    writeLink(link: 'links/a.link', target: 'targets/b.target');
+
+    await expectModifyEvent('links/a.link');
+  });
+
+  test('does not notify when a link target is modified', () async {
+    createDir('targets');
+    createDir('links');
+    writeFile('targets/a.target');
+    writeLink(link: 'links/a.link', target: 'targets/a.target');
+    await startWatcher(path: 'links');
+    writeFile('targets/a.target', contents: 'modified');
+
+    // TODO(davidmorgan): reconcile differences.
+    if (isNative) {
+      await expectNoEvents();
+    } else {
+      await expectModifyEvent('links/a.link');
+    }
+  });
+
+  test('does not notify when a link target is removed', () async {
+    createDir('targets');
+    createDir('links');
+    writeFile('targets/a.target');
+    writeLink(link: 'links/a.link', target: 'targets/a.target');
+    await startWatcher(path: 'links');
+
+    deleteFile('targets/a.target');
+
+    // TODO(davidmorgan): reconcile differences.
+    if (isNative) {
+      await expectNoEvents();
+    } else {
+      await expectRemoveEvent('links/a.link');
+    }
+  });
+
+  test('notifies when a link is moved within the watched directory', () async {
+    createDir('targets');
+    createDir('links');
+    writeFile('targets/a.target');
+    writeLink(link: 'links/a.link', target: 'targets/a.target');
+    await startWatcher(path: 'links');
+
+    renameLink('links/a.link', 'links/b.link');
+
+    await inAnyOrder(
+        [isAddEvent('links/b.link'), isRemoveEvent('links/a.link')]);
+  });
+
+  test('notifies when a link to an empty directory is added', () async {
+    createDir('targets');
+    createDir('links');
+    createDir('targets/a.targetdir');
+    await startWatcher(path: 'links');
+
+    writeLink(link: 'links/a.link', target: 'targets/a.targetdir');
+
+    // TODO(davidmorgan): reconcile differences.
+    if (isNative) {
+      await expectAddEvent('links/a.link');
+    } else {
+      await expectNoEvents();
+    }
+  });
+
+  test(
+      'does not notify about directory contents '
+      'when a link to a directory is added', () async {
+    createDir('targets');
+    createDir('links');
+    createDir('targets/a.targetdir');
+    writeFile('targets/a.targetdir/a.target');
+    await startWatcher(path: 'links');
+
+    writeLink(link: 'links/a.link', target: 'targets/a.targetdir');
+
+    // TODO(davidmorgan): reconcile differences.
+    if (isNative) {
+      await expectAddEvent('links/a.link');
+    } else {
+      await expectAddEvent('links/a.link/a.target');
+    }
+  });
+
+  test('notifies when a file is added to a linked directory', () async {
+    createDir('targets');
+    createDir('links');
+    createDir('targets/a.targetdir');
+    writeLink(link: 'links/a.link', target: 'targets/a.targetdir');
+    await startWatcher(path: 'links');
+
+    writeFile('targets/a.targetdir/a.txt');
+
+    // TODO(davidmorgan): reconcile differences.
+    if (!isNative || Platform.isLinux) {
+      await expectAddEvent('links/a.link/a.txt');
+    } else {
+      await expectNoEvents();
+    }
+  });
+
+  test(
+      'notifies about linked directory contents when a directory with a linked '
+      'subdirectory is moved in', () async {
+    createDir('targets');
+    createDir('links');
+    createDir('targets/a.targetdir');
+    createDir('watched');
+    writeFile('targets/a.targetdir/a.txt');
+    writeLink(link: 'links/a.link', target: 'targets/a.targetdir');
+    await startWatcher(path: 'watched');
+
+    renameDir('links', 'watched/links');
+
+    await expectAddEvent('watched/links/a.link/a.txt');
+  });
+
+  test(
+      'notifies about linked directory contents when a directory with a linked '
+      'subdirectory containing a link loop is moved in', () async {
+    createDir('targets');
+    createDir('links');
+    createDir('targets/a.targetdir');
+    createDir('watched');
+    writeFile('targets/a.targetdir/a.txt');
+    writeLink(link: 'links/a.link', target: 'targets/a.targetdir');
+    writeLink(
+        link: 'targets/a.targetdir/cycle.link', target: 'targets/a.targetdir');
+    await startWatcher(path: 'watched');
+
+    renameDir('links', 'watched/links');
+
+    // TODO(davidmorgan): reconcile differences.
+    if (isNative && (Platform.isLinux || Platform.isMacOS)) {
+      await inAnyOrder([
+        isAddEvent('watched/links/a.link/a.txt'),
+        isAddEvent('watched/links/a.link/cycle.link/a.txt'),
+        isAddEvent('watched/links/a.link/cycle.link/cycle.link'),
+      ]);
+      await expectNoEvents();
+    } else if (isNative && Platform.isWindows) {
+      await inAnyOrder([
+        isAddEvent('watched/links/a.link/a.txt'),
+        isAddEvent('watched/links/a.link/cycle.link'),
+      ]);
+      await expectNoEvents();
+    } else if (!isNative && Platform.isWindows) {
+      await inAnyOrder([
+        isAddEvent('watched/links/a.link/a.txt'),
+      ]);
+      await expectNoEvents();
+    } else {
+      assert(!isNative);
+      await inAnyOrder([
+        isAddEvent('watched/links/a.link/a.txt'),
+        isAddEvent('watched/links/a.link/cycle.link/a.txt'),
+      ]);
+      await expectNoEvents();
+    }
+  });
+
+  test(
+      'notifies about linked directory contents when a directory with a linked '
+      'subdirectory containing two link loops is moved in', () async {
+    createDir('targets');
+    createDir('links');
+    createDir('targets/a.targetdir');
+    createDir('watched');
+    writeFile('targets/a.targetdir/a.txt');
+    writeLink(link: 'links/a.link', target: 'targets/a.targetdir');
+    writeLink(
+        link: 'targets/a.targetdir/cycle1.link', target: 'targets/a.targetdir');
+    writeLink(
+        link: 'targets/a.targetdir/cycle2.link', target: 'targets/a.targetdir');
+    await startWatcher(path: 'watched');
+
+    renameDir('links', 'watched/links');
+
+    // TODO(davidmorgan): reconcile differences.
+    if (isNative && (Platform.isLinux || Platform.isMacOS)) {
+      await inAnyOrder([
+        isAddEvent('watched/links/a.link/a.txt'),
+        isAddEvent('watched/links/a.link/cycle1.link/a.txt'),
+        isAddEvent('watched/links/a.link/cycle1.link/cycle1.link'),
+        isAddEvent('watched/links/a.link/cycle1.link/cycle2.link/a.txt'),
+        isAddEvent('watched/links/a.link/cycle1.link/cycle2.link/cycle1.link'),
+        isAddEvent('watched/links/a.link/cycle1.link/cycle2.link/cycle2.link'),
+        isAddEvent('watched/links/a.link/cycle2.link/a.txt'),
+        isAddEvent('watched/links/a.link/cycle2.link/cycle1.link/a.txt'),
+        isAddEvent('watched/links/a.link/cycle2.link/cycle1.link/cycle1.link'),
+        isAddEvent('watched/links/a.link/cycle2.link/cycle1.link/cycle2.link'),
+        isAddEvent('watched/links/a.link/cycle2.link/cycle2.link'),
+      ]);
+      await expectNoEvents();
+    } else if (isNative && Platform.isWindows) {
+      await inAnyOrder([
+        isAddEvent('watched/links/a.link/a.txt'),
+        isAddEvent('watched/links/a.link/cycle1.link'),
+        isAddEvent('watched/links/a.link/cycle2.link'),
+      ]);
+      await expectNoEvents();
+    } else if (!isNative && Platform.isWindows) {
+      await inAnyOrder([
+        isAddEvent('watched/links/a.link/a.txt'),
+      ]);
+      await expectNoEvents();
+    } else {
+      assert(!isNative);
+      await inAnyOrder([
+        isAddEvent('watched/links/a.link/a.txt'),
+        isAddEvent('watched/links/a.link/cycle1.link/a.txt'),
+        isAddEvent('watched/links/a.link/cycle1.link/cycle2.link/a.txt'),
+        isAddEvent('watched/links/a.link/cycle2.link/a.txt'),
+        isAddEvent('watched/links/a.link/cycle2.link/cycle1.link/a.txt'),
+      ]);
+      await expectNoEvents();
+    }
+  });
+}
diff --git a/pkgs/watcher/test/directory_watcher/linux_test.dart b/pkgs/watcher/test/directory_watcher/linux_test.dart
index a10a72c33..a47779466 100644
--- a/pkgs/watcher/test/directory_watcher/linux_test.dart
+++ b/pkgs/watcher/test/directory_watcher/linux_test.dart
@@ -10,12 +10,14 @@ import 'package:watcher/src/directory_watcher/linux.dart';
 import 'package:watcher/watcher.dart';
 
 import '../utils.dart';
-import 'shared.dart';
+import 'file_tests.dart';
+import 'link_tests.dart';
 
 void main() {
   watcherFactory = LinuxDirectoryWatcher.new;
 
-  sharedTests();
+  fileTests();
+  linkTests(isNative: true);
 
   test('DirectoryWatcher creates a LinuxDirectoryWatcher on Linux', () {
     expect(DirectoryWatcher('.'), const TypeMatcher<LinuxDirectoryWatcher>());
diff --git a/pkgs/watcher/test/directory_watcher/mac_os_test.dart b/pkgs/watcher/test/directory_watcher/mac_os_test.dart
index 337662646..ba52d1958 100644
--- a/pkgs/watcher/test/directory_watcher/mac_os_test.dart
+++ b/pkgs/watcher/test/directory_watcher/mac_os_test.dart
@@ -10,12 +10,14 @@ import 'package:watcher/src/directory_watcher/mac_os.dart';
 import 'package:watcher/watcher.dart';
 
 import '../utils.dart';
-import 'shared.dart';
+import 'file_tests.dart';
+import 'link_tests.dart';
 
 void main() {
   watcherFactory = MacOSDirectoryWatcher.new;
 
-  sharedTests();
+  fileTests();
+  linkTests(isNative: true);
 
   test('DirectoryWatcher creates a MacOSDirectoryWatcher on Mac OS', () {
     expect(DirectoryWatcher('.'), const TypeMatcher<MacOSDirectoryWatcher>());
diff --git a/pkgs/watcher/test/directory_watcher/polling_test.dart b/pkgs/watcher/test/directory_watcher/polling_test.dart
index 5b16c13d7..9fd2a0afd 100644
--- a/pkgs/watcher/test/directory_watcher/polling_test.dart
+++ b/pkgs/watcher/test/directory_watcher/polling_test.dart
@@ -9,7 +9,8 @@ import 'package:test/test.dart';
 import 'package:watcher/watcher.dart';
 
 import '../utils.dart';
-import 'shared.dart';
+import 'file_tests.dart';
+import 'link_tests.dart';
 
 void main() {
   // Use a short delay to make the tests run quickly.
@@ -20,7 +21,8 @@ void main() {
   group('with mock mtime', () {
     setUp(enableMockModificationTimes);
 
-    sharedTests();
+    fileTests();
+    linkTests(isNative: false);
 
     test('does not notify if the modification time did not change', () async {
       writeFile('a.txt', contents: 'before');
@@ -36,6 +38,7 @@ void main() {
   group('with real mtime', () {
     setUp(enableWaitingForDifferentModificationTimes);
 
-    sharedTests();
+    fileTests();
+    linkTests(isNative: false);
   });
 }
diff --git a/pkgs/watcher/test/directory_watcher/windows_test.dart b/pkgs/watcher/test/directory_watcher/windows_test.dart
index 709bcb59b..406a0755e 100644
--- a/pkgs/watcher/test/directory_watcher/windows_test.dart
+++ b/pkgs/watcher/test/directory_watcher/windows_test.dart
@@ -15,12 +15,14 @@ import 'package:watcher/src/directory_watcher/windows.dart';
 import 'package:watcher/watcher.dart';
 
 import '../utils.dart';
-import 'shared.dart';
+import 'file_tests.dart';
+import 'link_tests.dart';
 
 void main() {
   watcherFactory = WindowsDirectoryWatcher.new;
 
-  group('Shared Tests:', sharedTests);
+  fileTests();
+  linkTests(isNative: true);
 
   test('DirectoryWatcher creates a WindowsDirectoryWatcher on Windows', () {
     expect(DirectoryWatcher('.'), const TypeMatcher<WindowsDirectoryWatcher>());
diff --git a/pkgs/watcher/test/file_watcher/link_tests.dart b/pkgs/watcher/test/file_watcher/link_tests.dart
index a9de2cf0a..8cb5e102d 100644
--- a/pkgs/watcher/test/file_watcher/link_tests.dart
+++ b/pkgs/watcher/test/file_watcher/link_tests.dart
@@ -60,7 +60,7 @@ void linkTests({required bool isNative}) {
 
   test('notifies when a link is removed', () async {
     await startWatcher(path: 'link.txt');
-    deleteFile('link.txt');
+    deleteLink('link.txt');
 
     // TODO(davidmorgan): reconcile differences.
     if (isNative) {
diff --git a/pkgs/watcher/test/utils.dart b/pkgs/watcher/test/utils.dart
index db16e3f8c..bcc905232 100644
--- a/pkgs/watcher/test/utils.dart
+++ b/pkgs/watcher/test/utils.dart
@@ -107,6 +107,11 @@ void enableMockModificationTimes() {
     if (link.existsSync()) {
       path = link.resolveSymbolicLinksSync();
     }
+    // Also resolve symbolic links in the enclosing directory.
+    final file = File(path);
+    if (file.existsSync()) {
+      path = file.resolveSymbolicLinksSync();
+    }
 
     var normalized = p.normalize(p.relative(path, from: d.sandbox));
 
@@ -324,6 +329,8 @@ void writeFile(String path, {String? contents, bool? updateModified}) {
 
 /// Writes a file in the sandbox at [link] pointing to [target].
 ///
+/// [target] is relative to the sandbox, not to [link].
+///
 /// If [updateModified] is `false` and mock modification times are in use, the
 /// mock file modification time is not changed.
 void writeLink({
@@ -343,13 +350,12 @@ void writeLink({
     dir.createSync(recursive: true);
   }
 
-  Link(fullPath).createSync(target);
+  Link(fullPath).createSync(p.join(d.sandbox, target));
 
   if (updateModified) {
     link = p.normalize(link);
 
     final mockFileModificationTimes = _mockFileModificationTimes;
-
     if (mockFileModificationTimes != null) {
       mockFileModificationTimes[link] = _nextTimestamp++;
     }
@@ -358,7 +364,23 @@ void writeLink({
 
 /// Deletes a file in the sandbox at [path].
 void deleteFile(String path) {
-  File(p.join(d.sandbox, path)).deleteSync();
+  final fullPath = p.join(d.sandbox, path);
+  expect(FileSystemEntity.typeSync(fullPath, followLinks: false),
+      FileSystemEntityType.file);
+  File(fullPath).deleteSync();
+
+  final mockFileModificationTimes = _mockFileModificationTimes;
+  if (mockFileModificationTimes != null) {
+    mockFileModificationTimes.remove(path);
+  }
+}
+
+/// Deletes a link in the sandbox at [path].
+void deleteLink(String path) {
+  final fullPath = p.join(d.sandbox, path);
+  expect(FileSystemEntity.typeSync(fullPath, followLinks: false),
+      FileSystemEntityType.link);
+  Link(fullPath).deleteSync();
 
   final mockFileModificationTimes = _mockFileModificationTimes;
   if (mockFileModificationTimes != null) {
@@ -433,7 +455,10 @@ void renameDir(String from, String to) {
 
 /// Deletes a directory in the sandbox at [path].
 void deleteDir(String path) {
-  Directory(p.join(d.sandbox, path)).deleteSync(recursive: true);
+  final fullPath = p.join(d.sandbox, path);
+  expect(FileSystemEntity.typeSync(fullPath, followLinks: false),
+      FileSystemEntityType.directory);
+  Directory(fullPath).deleteSync(recursive: true);
 }
 
 /// Runs [callback] with every permutation of non-negative numbers for each