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 ec97cb875ca..4905198869b 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
@@ -5,6 +5,7 @@
 import 'dart:async';
 
 import 'package:build_daemon/client.dart';
+import 'package:dwds/dwds.dart';
 import 'package:meta/meta.dart';
 import 'package:vm_service/vm_service.dart' as vmservice;
 import 'package:webkit_inspection_protocol/webkit_inspection_protocol.dart' hide StackTrace;
@@ -229,6 +230,10 @@ class ResidentWebRunner extends ResidentRunner {
       throwToolExit('Failed to connect to WebSocket.');
     } on BuildException {
       throwToolExit('Failed to build application for the Web.');
+    } on ChromeDebugException catch (err, stackTrace) {
+      throwToolExit(
+        'Failed to establish connection with Chrome. Try running the application again.\n'
+        'If this problem persists, please file an issue with the details below:\n$err\n$stackTrace');
     } on SocketException catch (err) {
       throwToolExit(err.toString());
     } on StateError catch (err) {
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 5a6075cc4c8..0696195eafe 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
@@ -584,6 +584,25 @@ void main() {
     await expectation;
   }));
 
+  test('Successfully turns ChromeDebugError into ToolExit', () => testbed.run(() async {
+     _setupMocks();
+    final Completer<DebugConnectionInfo> connectionInfoCompleter = Completer<DebugConnectionInfo>();
+    final Completer<void> unhandledErrorCompleter = Completer<void>();
+    when(mockWebFs.connect(any)).thenAnswer((Invocation _) async {
+      unawaited(unhandledErrorCompleter.future.then((void value) {
+        throw ChromeDebugException(<String, dynamic>{});
+      }));
+      return ConnectionResult(mockAppConnection, mockDebugConnection);
+    });
+
+    final Future<void> expectation = expectLater(() => residentWebRunner.run(
+      connectionInfoCompleter: connectionInfoCompleter,
+    ), throwsA(isInstanceOf<ToolExit>()));
+
+    unhandledErrorCompleter.complete();
+    await expectation;
+  }));
+
   test('Successfully turns OptionsSkew error into ToolExit', () => testbed.run(() async {
     _setupMocks();
     final Completer<DebugConnectionInfo> connectionInfoCompleter = Completer<DebugConnectionInfo>();