diff --git a/runtime/bin/directory_win.cc b/runtime/bin/directory_win.cc
index 3e1992397b4..41d58e83513 100644
--- a/runtime/bin/directory_win.cc
+++ b/runtime/bin/directory_win.cc
@@ -508,6 +508,7 @@ bool Directory::Rename(Namespace* namespc,
   Utf8ToWideScope system_path(prefixed_dir);
   ExistsResult exists = ExistsHelper(system_path.wide());
   if (exists != EXISTS) {
+    SetLastError(ERROR_FILE_NOT_FOUND);
     return false;
   }
   const char* prefixed_new_dir = PrefixLongDirectoryPath(new_path);
diff --git a/tests/standalone/io/directory_rename_test.dart b/tests/standalone/io/directory_rename_test.dart
index de14cea0b8a..277b5ba697e 100644
--- a/tests/standalone/io/directory_rename_test.dart
+++ b/tests/standalone/io/directory_rename_test.dart
@@ -141,7 +141,10 @@ testRenameButActuallyFile() async {
     } on FileSystemException catch (e) {
       Expect.isTrue(
           e.message.contains('Rename failed'), 'Unexpected error: $e');
-      if (Platform.isLinux || Platform.isMacOS) {
+      if (Platform.isWindows) {
+        Expect.isTrue(e.osError!.message.contains('cannot find the file'),
+            'Unexpected error: $e');
+      } else if (Platform.isLinux || Platform.isMacOS) {
         Expect.isTrue(e.osError!.message.contains('Not a directory'),
             'Unexpected error: $e');
       }
diff --git a/tests/standalone_2/io/directory_rename_test.dart b/tests/standalone_2/io/directory_rename_test.dart
index 5f47913813c..18cbba31d20 100644
--- a/tests/standalone_2/io/directory_rename_test.dart
+++ b/tests/standalone_2/io/directory_rename_test.dart
@@ -143,7 +143,10 @@ testRenameButActuallyFile() async {
     } on FileSystemException catch (e) {
       Expect.isTrue(
           e.message.contains('Rename failed'), 'Unexpected error: $e');
-      if (Platform.isLinux || Platform.isMacOS) {
+      if (Platform.isWindows) {
+        Expect.isTrue(e.osError.message.contains('cannot find the file'),
+            'Unexpected error: $e');
+      } else if (Platform.isLinux || Platform.isMacOS) {
         Expect.isTrue(e.osError.message.contains('Not a directory'),
             'Unexpected error: $e');
       }