diff --git a/packages/flutter_tools/lib/src/build_runner/resident_web_runner.dart b/packages/flutter_tools/lib/src/build_runner/resident_web_runner.dart
index af710d68b07..dfa4f78807c 100644
--- a/packages/flutter_tools/lib/src/build_runner/resident_web_runner.dart
+++ b/packages/flutter_tools/lib/src/build_runner/resident_web_runner.dart
@@ -73,6 +73,7 @@ class ResidentWebRunner extends ResidentRunner {
   WebFs _webFs;
   DebugConnection _debugConnection;
   StreamSubscription<vmservice.Event> _stdOutSub;
+  bool _exited = false;
 
   vmservice.VmService get _vmService => _debugConnection.vmService;
 
@@ -101,9 +102,13 @@ class ResidentWebRunner extends ResidentRunner {
   }
 
   Future<void> _cleanup() async {
+    if (_exited) {
+      return;
+    }
     await _debugConnection?.close();
     await _stdOutSub?.cancel();
     await _webFs?.stop();
+    _exited = true;
   }
 
   @override
diff --git a/packages/flutter_tools/lib/src/web/chrome.dart b/packages/flutter_tools/lib/src/web/chrome.dart
index 34e5ecf64b2..f6be2e77369 100644
--- a/packages/flutter_tools/lib/src/web/chrome.dart
+++ b/packages/flutter_tools/lib/src/web/chrome.dart
@@ -155,26 +155,25 @@ class ChromeLauncher {
   static Future<Chrome> get connectedInstance => _currentCompleter.future;
 
   /// Returns the full URL of the Chrome remote debugger for the main page.
-///
-/// This takes the [base] remote debugger URL (which points to a browser-wide
-/// page) and uses its JSON API to find the resolved URL for debugging the host
-/// page.
-Future<Uri> _getRemoteDebuggerUrl(Uri base) async {
-  try {
-    final HttpClient client = HttpClient();
-    final HttpClientRequest request = await client.getUrl(base.resolve('/json/list'));
-    final HttpClientResponse response = await request.close();
-    final List<dynamic> jsonObject = await json.fuse(utf8).decoder.bind(response).single;
-    return base.resolve(jsonObject.first['devtoolsFrontendUrl']);
-  } catch (_) {
-    // If we fail to talk to the remote debugger protocol, give up and return
-    // the raw URL rather than crashing.
-    return base;
+  ///
+  /// This takes the [base] remote debugger URL (which points to a browser-wide
+  /// page) and uses its JSON API to find the resolved URL for debugging the host
+  /// page.
+  Future<Uri> _getRemoteDebuggerUrl(Uri base) async {
+    try {
+      final HttpClient client = HttpClient();
+      final HttpClientRequest request = await client.getUrl(base.resolve('/json/list'));
+      final HttpClientResponse response = await request.close();
+      final List<dynamic> jsonObject = await json.fuse(utf8).decoder.bind(response).single;
+      return base.resolve(jsonObject.first['devtoolsFrontendUrl']);
+    } catch (_) {
+      // If we fail to talk to the remote debugger protocol, give up and return
+      // the raw URL rather than crashing.
+      return base;
+    }
   }
 }
 
-}
-
 /// A class for managing an instance of Chrome.
 class Chrome {
   Chrome._(
diff --git a/packages/flutter_tools/test/general.shard/resident_web_runner_test.dart b/packages/flutter_tools/test/general.shard/resident_web_runner_test.dart
index db867cf10ad..251650dc60e 100644
--- a/packages/flutter_tools/test/general.shard/resident_web_runner_test.dart
+++ b/packages/flutter_tools/test/general.shard/resident_web_runner_test.dart
@@ -338,6 +338,25 @@ void main() {
     verify(mockVmService.callServiceExtension('ext.flutter.profileWidgetBuilds',
         args: <String, Object>{'enabled': true})).called(1);
   }));
+
+  test('cleanup of resources is safe to call multiple times', () => testbed.run(() async {
+    _setupMocks();
+    bool debugClosed = false;
+    when(mockDebugConnection.close()).thenAnswer((Invocation invocation) async {
+      if (debugClosed) {
+        throw StateError('debug connection closed twice');
+      }
+      debugClosed = true;
+    });
+    final Completer<DebugConnectionInfo> connectionInfoCompleter = Completer<DebugConnectionInfo>();
+     unawaited(residentWebRunner.run(
+      connectionInfoCompleter: connectionInfoCompleter,
+    ));
+    await connectionInfoCompleter.future;
+
+    await residentWebRunner.exit();
+    await residentWebRunner.exit();
+  }));
 }