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 6c5506b5021..de14319cf0c 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
@@ -4,14 +4,17 @@
 
 import 'dart:async';
 
+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;
 
 import '../application_package.dart';
+import '../base/async_guard.dart';
 import '../base/common.dart';
 import '../base/file_system.dart';
+import '../base/io.dart';
 import '../base/logger.dart';
 import '../base/net.dart';
 import '../base/terminal.dart';
@@ -61,6 +64,10 @@ class DwdsWebRunnerFactory extends WebRunnerFactory {
   }
 }
 
+const String kExitMessage =  'Failed to establish connection with the application '
+  'instance in Chrome.\nThis can happen if the websocket connection used by the '
+  'web tooling is unable to correctly establish a connection, for example due to a firewall.';
+
 /// A hot-runner which handles browser specific delegation.
 abstract class ResidentWebRunner extends ResidentRunner {
   ResidentWebRunner(
@@ -393,45 +400,59 @@ class _ResidentWebRunner extends ResidentWebRunner {
     final int hostPort = debuggingOptions.port == null
         ? await globals.os.findFreePort()
         : int.tryParse(debuggingOptions.port);
-    device.devFS = WebDevFS(
-      hostname: effectiveHostname,
-      port: hostPort,
-      packagesFilePath: packagesFilePath,
-      urlTunneller: urlTunneller,
-      buildMode: debuggingOptions.buildInfo.mode,
-      enableDwds: _enableDwds,
-      entrypoint: globals.fs.file(target).uri,
-    );
-    final Uri url = await device.devFS.create();
-    if (debuggingOptions.buildInfo.isDebug) {
-      final UpdateFSReport report = await _updateDevFS(fullRestart: true);
-      if (!report.success) {
-        globals.printError('Failed to compile application.');
-        return 1;
-      }
-      device.generator.accept();
-    } else {
-       await buildWeb(
-        flutterProject,
-        target,
-        debuggingOptions.buildInfo,
-        debuggingOptions.initializePlatform,
-        dartDefines,
-        false,
-      );
+
+    try {
+      return await asyncGuard(() async {
+        device.devFS = WebDevFS(
+          hostname: effectiveHostname,
+          port: hostPort,
+          packagesFilePath: packagesFilePath,
+          urlTunneller: urlTunneller,
+          buildMode: debuggingOptions.buildInfo.mode,
+          enableDwds: _enableDwds,
+          entrypoint: globals.fs.file(target).uri,
+        );
+        final Uri url = await device.devFS.create();
+        if (debuggingOptions.buildInfo.isDebug) {
+          final UpdateFSReport report = await _updateDevFS(fullRestart: true);
+          if (!report.success) {
+            globals.printError('Failed to compile application.');
+            return 1;
+          }
+          device.generator.accept();
+        } else {
+          await buildWeb(
+            flutterProject,
+            target,
+            debuggingOptions.buildInfo,
+            debuggingOptions.initializePlatform,
+            dartDefines,
+            false,
+          );
+        }
+        await device.device.startApp(
+          package,
+          mainPath: target,
+          debuggingOptions: debuggingOptions,
+          platformArgs: <String, Object>{
+            'uri': url.toString(),
+          },
+        );
+        return attach(
+          connectionInfoCompleter: connectionInfoCompleter,
+          appStartedCompleter: appStartedCompleter,
+        );
+      });
+    } on WebSocketException {
+      throwToolExit(kExitMessage);
+    } on ChromeDebugException {
+      throwToolExit(kExitMessage);
+    } on AppConnectionException {
+      throwToolExit(kExitMessage);
+    } on SocketException {
+      throwToolExit(kExitMessage);
     }
-    await device.device.startApp(
-      package,
-      mainPath: target,
-      debuggingOptions: debuggingOptions,
-      platformArgs: <String, Object>{
-        'uri': url.toString(),
-      },
-    );
-    return attach(
-      connectionInfoCompleter: connectionInfoCompleter,
-      appStartedCompleter: appStartedCompleter,
-    );
+    return 0;
   }
 
   @override
@@ -479,22 +500,25 @@ class _ResidentWebRunner extends ResidentWebRunner {
       }
     }
 
+    Duration transferMarker;
     try {
       if (!deviceIsDebuggable) {
         globals.printStatus('Recompile complete. Page requires refresh.');
-      } else if (fullRestart || !debuggingOptions.buildInfo.isDebug) {
+      } else if (!debuggingOptions.buildInfo.isDebug) {
         // On non-debug builds, a hard refresh is required to ensure the
         // up to date sources are loaded.
         await _wipConnection?.sendCommand('Page.reload', <String, Object>{
           'ignoreCache': !debuggingOptions.buildInfo.isDebug,
         });
       } else {
-        await _wipConnection?.debugger
-            ?.sendCommand('Runtime.evaluate', params: <String, Object>{
-          'expression': 'window.\$hotReloadHook([$reloadModules])',
-          'awaitPromise': true,
-          'returnByValue': true,
-        });
+        transferMarker = timer.elapsed;
+        await _wipConnection?.debugger?.sendCommand(
+          'Runtime.evaluate', params: <String, Object>{
+            'expression': 'window.\$hotReloadHook([$reloadModules])',
+            'awaitPromise': true,
+            'returnByValue': true,
+          },
+        );
       }
     } on WipError catch (err) {
       globals.printError(err.toString());
@@ -503,8 +527,8 @@ class _ResidentWebRunner extends ResidentWebRunner {
       status.stop();
     }
 
-    final String verb = fullRestart ? 'Restarted' : 'Reloaded';
-    globals.printStatus('$verb application in ${getElapsedAsMilliseconds(timer.elapsed)}.');
+    final String elapsed = getElapsedAsMilliseconds(timer.elapsed);
+    globals.printStatus('Restarted application in $elapsed.');
 
     // Don't track restart times for dart2js builds or web-server devices.
     if (debuggingOptions.buildInfo.isDebug && deviceIsDebuggable) {
@@ -517,6 +541,7 @@ class _ResidentWebRunner extends ResidentWebRunner {
         fullRestart: true,
         reason: reason,
         overallTimeInMs: timer.elapsed.inMilliseconds,
+        transferTimeInMs: timer.elapsed.inMilliseconds - transferMarker.inMilliseconds
       ).send();
     }
     return OperationResult.ok;
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 4fb7fce0bd4..b153a3642d1 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
@@ -7,6 +7,7 @@ import 'dart:convert';
 
 import 'package:dwds/dwds.dart';
 import 'package:flutter_tools/src/base/common.dart';
+import 'package:flutter_tools/src/base/io.dart';
 import 'package:flutter_tools/src/base/logger.dart';
 import 'package:flutter_tools/src/base/terminal.dart';
 import 'package:flutter_tools/src/build_info.dart';
@@ -316,7 +317,7 @@ void main() {
 
     final OperationResult result = await residentWebRunner.restart(fullRestart: false);
 
-    expect(testLogger.statusText, contains('Reloaded application in'));
+    expect(testLogger.statusText, contains('Restarted application in'));
     expect(result.code, 0);
     verify(mockResidentCompiler.accept()).called(2);
 	  // ensure that analytics are sent.
@@ -836,6 +837,112 @@ void main() {
   }, overrides: <Type, Generator>{
     Logger: () => DelegateLogger(MockLogger())
   }));
+
+  test('Successfully turns WebSocketException into ToolExit', () => testbed.run(() async {
+    _setupMocks();
+    final Completer<DebugConnectionInfo> connectionInfoCompleter = Completer<DebugConnectionInfo>();
+    final Completer<void> unhandledErrorCompleter = Completer<void>();
+     when(mockWebDevFS.connect(any)).thenAnswer((Invocation _) async {
+      unawaited(unhandledErrorCompleter.future.then((void value) {
+        throw const WebSocketException();
+      }));
+      return ConnectionResult(mockAppConnection, mockDebugConnection);
+    });
+
+    final Future<void> expectation = expectLater(() => residentWebRunner.run(
+      connectionInfoCompleter: connectionInfoCompleter,
+    ), throwsToolExit());
+
+    unhandledErrorCompleter.complete();
+    await expectation;
+  }));
+
+  test('Successfully turns AppConnectionException into ToolExit', () => testbed.run(() async {
+    _setupMocks();
+    final Completer<DebugConnectionInfo> connectionInfoCompleter = Completer<DebugConnectionInfo>();
+    final Completer<void> unhandledErrorCompleter = Completer<void>();
+    when(mockWebDevFS.connect(any)).thenAnswer((Invocation _) async {
+      unawaited(unhandledErrorCompleter.future.then((void value) {
+        throw AppConnectionException('Could not connect to application with appInstanceId: c0ae0750-ee91-11e9-cea6-35d95a968356');
+      }));
+      return ConnectionResult(mockAppConnection, mockDebugConnection);
+    });
+
+    final Future<void> expectation = expectLater(() => residentWebRunner.run(
+      connectionInfoCompleter: connectionInfoCompleter,
+    ), throwsToolExit());
+
+    unhandledErrorCompleter.complete();
+    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(mockWebDevFS.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,
+    ), throwsToolExit());
+
+    unhandledErrorCompleter.complete();
+    await expectation;
+  }));
+
+  test('Rethrows Exception type', () => testbed.run(() async {
+    _setupMocks();
+    final Completer<DebugConnectionInfo> connectionInfoCompleter = Completer<DebugConnectionInfo>();
+    final Completer<void> unhandledErrorCompleter = Completer<void>();
+     when(mockWebDevFS.connect(any)).thenAnswer((Invocation _) async {
+      unawaited(unhandledErrorCompleter.future.then((void value) {
+        throw Exception('Something went wrong');
+      }));
+      return ConnectionResult(mockAppConnection, mockDebugConnection);
+    });
+
+    final Future<void> expectation = expectLater(() => residentWebRunner.run(
+      connectionInfoCompleter: connectionInfoCompleter,
+    ), throwsException);
+
+    unhandledErrorCompleter.complete();
+    await expectation;
+  }));
+  test('Rethrows unknown exception type from web tooling', () => testbed.run(() async {
+    _setupMocks();
+    final DelegateLogger delegateLogger = globals.logger as DelegateLogger;
+    final MockStatus mockStatus = MockStatus();
+    delegateLogger.status = mockStatus;
+    final Completer<DebugConnectionInfo> connectionInfoCompleter = Completer<DebugConnectionInfo>();
+    final Completer<void> unhandledErrorCompleter = Completer<void>();
+    when(mockWebDevFS.connect(any)).thenAnswer((Invocation _) async {
+      unawaited(unhandledErrorCompleter.future.then((void value) {
+        throw StateError('Something went wrong');
+      }));
+      return ConnectionResult(mockAppConnection, mockDebugConnection);
+    });
+
+    final Future<void> expectation = expectLater(() => residentWebRunner.run(
+      connectionInfoCompleter: connectionInfoCompleter,
+    ), throwsStateError);
+
+    unhandledErrorCompleter.complete();
+    await expectation;
+    verify(mockStatus.stop()).called(1);
+  }, overrides: <Type, Generator>{
+    Logger: () => DelegateLogger(BufferLogger(
+      terminal: AnsiTerminal(
+        stdio: null,
+        platform: const LocalPlatform(),
+      ),
+      outputPreferences: OutputPreferences.test(),
+    ))
+  }));
 }
 
 class MockChromeLauncher extends Mock implements ChromeLauncher {}