diff --git a/test/cli/dart/watch_test.dart b/test/cli/dart/watch_test.dart
index 3e6fd7ea..b50568d4 100644
--- a/test/cli/dart/watch_test.dart
+++ b/test/cli/dart/watch_test.dart
@@ -5,6 +5,10 @@
 // OS X's modification time reporting is flaky, so we skip these tests on it.
 @TestOn('vm && !mac-os')
 
+// File watching is inherently flaky at the OS level. To mitigate this, we do a
+// few retries when the tests fail.
+@Retry(3)
+
 import 'package:test/test.dart';
 
 import '../dart_test.dart';
diff --git a/test/cli/node/watch_test.dart b/test/cli/node/watch_test.dart
index f1bffdaa..780b649d 100644
--- a/test/cli/node/watch_test.dart
+++ b/test/cli/node/watch_test.dart
@@ -6,6 +6,10 @@
 @TestOn('vm && !mac-os')
 @Tags(['node'])
 
+// File watching is inherently flaky at the OS level. To mitigate this, we do a
+// few retries when the tests fail.
+@Retry(3)
+
 import 'package:test/test.dart';
 
 import '../../ensure_npm_package.dart';