diff --git a/dev/bots/service_worker_test.dart b/dev/bots/service_worker_test.dart
new file mode 100644
index 0000000000..5c5b30a00f
--- /dev/null
+++ b/dev/bots/service_worker_test.dart
@@ -0,0 +1,143 @@
+// Copyright 2014 The Flutter Authors. All rights reserved.
+// Use of this source code is governed by a BSD-style license that can be
+// found in the LICENSE file.
+
+import 'dart:async';
+import 'dart:io';
+
+import 'package:path/path.dart' as path;
+import 'package:flutter_devicelab/framework/browser.dart';
+import 'package:meta/meta.dart';
+import 'package:shelf/shelf.dart';
+import 'package:shelf_static/shelf_static.dart';
+import 'package:shelf/shelf_io.dart' as shelf_io;
+
+final String bat = Platform.isWindows ? '.bat' : '';
+final String flutterRoot = path.dirname(path.dirname(path.dirname(path.fromUri(Platform.script))));
+final String flutter = path.join(flutterRoot, 'bin', 'flutter$bat');
+
+
+// Run a web service worker test. The expectations are currently stored here
+// instead of in the application. This is not run on CI due to the requirement
+// of having a headful chrome instance.
+Future<void> main() async {
+  await _runWebServiceWorkerTest('lib/service_worker_test.dart');
+}
+
+Future<void> _runWebServiceWorkerTest(String target, {
+  List<String> additionalArguments = const<String>[],
+}) async {
+  final String testAppDirectory = path.join(flutterRoot, 'dev', 'integration_tests', 'web');
+  final String appBuildDirectory = path.join(testAppDirectory, 'build', 'web');
+
+  // Build the app.
+  await Process.run(
+    flutter,
+    <String>[ 'clean' ],
+    workingDirectory: testAppDirectory,
+  );
+  await Process.run(
+    flutter,
+    <String>[
+      'build',
+      'web',
+      '--release',
+      ...additionalArguments,
+      '-t',
+      target,
+    ],
+    workingDirectory: testAppDirectory,
+    environment: <String, String>{
+      'FLUTTER_WEB': 'true',
+    },
+  );
+  final List<Uri> requests = <Uri>[];
+  final List<Map<String, String>> headers = <Map<String, String>>[];
+  await runRecordingServer(
+    appUrl: 'http://localhost:8080/',
+    appDirectory: appBuildDirectory,
+    requests: requests,
+    headers: headers,
+    browserDebugPort: null,
+  );
+
+  final List<String> requestedPaths = requests.map((Uri uri) => uri.toString()).toList();
+  final List<String> expectedPaths = <String>[
+    // Initial page load
+    '',
+    'main.dart.js',
+    'assets/FontManifest.json',
+    'flutter_service_worker.js',
+    'manifest.json',
+    'favicon.ico',
+    // Service worker install.
+    'main.dart.js',
+    'index.html',
+    'assets/LICENSE',
+    'assets/AssetManifest.json',
+    'assets/FontManifest.json',
+    '',
+    // Second page load all cached.
+  ];
+  print('requests: $requestedPaths');
+  // The exact order isn't important or deterministic.
+  for (final String path in requestedPaths) {
+    if (!expectedPaths.remove(path)) {
+      print('unexpected service worker request: $path');
+      exit(1);
+    }
+  }
+  if (expectedPaths.isNotEmpty) {
+    print('Missing service worker requests from expected paths: $expectedPaths');
+    exit(1);
+  }
+}
+
+/// This server runs a release web application and verifies that the service worker
+/// caches files correctly, by checking the request resources over HTTP.
+///
+/// When it receives a request for `CLOSE` the server will be torn down.
+///
+/// Expects a path to the `build/web` directory produced from `flutter build web`.
+Future<void> runRecordingServer({
+  @required String appUrl,
+  @required String appDirectory,
+  @required List<Uri> requests,
+  @required List<Map<String, String>> headers,
+  int serverPort = 8080,
+  int browserDebugPort = 8081,
+}) async {
+  Chrome chrome;
+  HttpServer server;
+  final Completer<void> completer = Completer<void>();
+  Directory userDataDirectory;
+  try {
+    server = await HttpServer.bind('localhost', serverPort);
+    final Cascade cascade = Cascade()
+      .add((Request request) async {
+        if (request.url.toString().contains('CLOSE')) {
+          completer.complete();
+          return Response.notFound('');
+        }
+        requests.add(request.url);
+        headers.add(request.headers);
+        return Response.notFound('');
+      })
+      .add(createStaticHandler(appDirectory, defaultDocument: 'index.html'));
+    shelf_io.serveRequests(server, cascade.handler);
+    userDataDirectory = Directory.systemTemp.createTempSync('chrome_user_data_');
+    chrome = await Chrome.launch(ChromeOptions(
+      headless: false,
+      debugPort: browserDebugPort,
+      url: appUrl,
+      userDataDirectory: userDataDirectory.path,
+      windowHeight: 500,
+      windowWidth: 500,
+    ), onError: completer.completeError);
+    await completer.future;
+  } finally {
+    chrome?.stop();
+    await server?.close();
+    userDataDirectory.deleteSync(recursive: true);
+  }
+}
diff --git a/dev/devicelab/lib/framework/browser.dart b/dev/devicelab/lib/framework/browser.dart
index 7e0def9fbb..b62c4d74c8 100644
--- a/dev/devicelab/lib/framework/browser.dart
+++ b/dev/devicelab/lib/framework/browser.dart
@@ -7,6 +7,7 @@ import 'dart:convert' show json, utf8, LineSplitter, JsonEncoder;
 import 'dart:io' as io;
 import 'dart:math' as math;
 
+import 'package:path/path.dart' as path;
 import 'package:meta/meta.dart';
 import 'package:webkit_inspection_protocol/webkit_inspection_protocol.dart';
 
@@ -76,8 +77,12 @@ class Chrome {
   /// process encounters an error. In particular, [onError] is called when the
   /// Chrome process exits prematurely, i.e. before [stop] is called.
   static Future<Chrome> launch(ChromeOptions options, { String workingDirectory, @required ChromeErrorCallback onError }) async {
-    final io.ProcessResult versionResult = io.Process.runSync(_findSystemChromeExecutable(), const <String>['--version']);
-    print('Launching ${versionResult.stdout}');
+    if (!io.Platform.isWindows) {
+      final io.ProcessResult versionResult = io.Process.runSync(_findSystemChromeExecutable(), const <String>['--version']);
+      print('Launching ${versionResult.stdout}');
+    } else {
+      print('Launching Chrome...');
+    }
 
     final bool withDebugging = options.debugPort != null;
     final List<String> args = <String>[
@@ -217,8 +222,23 @@ String _findSystemChromeExecutable() {
     return (which.stdout as String).trim();
   } else if (io.Platform.isMacOS) {
     return '/Applications/Google Chrome.app/Contents/MacOS/Google Chrome';
+  } else if (io.Platform.isWindows) {
+    const String kWindowsExecutable = r'Google\Chrome\Application\chrome.exe';
+    final List<String> kWindowsPrefixes = <String>[
+      io.Platform.environment['LOCALAPPDATA'],
+      io.Platform.environment['PROGRAMFILES'],
+      io.Platform.environment['PROGRAMFILES(X86)'],
+    ];
+    final String windowsPrefix = kWindowsPrefixes.firstWhere((String prefix) {
+      if (prefix == null) {
+        return false;
+      }
+      final String expectedPath = path.join(prefix, kWindowsExecutable);
+      return io.File(expectedPath).existsSync();
+    }, orElse: () => '.');
+    return path.join(windowsPrefix, kWindowsExecutable);
   } else {
-    throw Exception('Web benchmarks cannot run on ${io.Platform.operatingSystem} yet.');
+    throw Exception('Web benchmarks cannot run on ${io.Platform.operatingSystem}.');
   }
 }
 
diff --git a/dev/integration_tests/web/lib/service_worker_test.dart b/dev/integration_tests/web/lib/service_worker_test.dart
new file mode 100644
index 0000000000..d1f90aa4d5
--- /dev/null
+++ b/dev/integration_tests/web/lib/service_worker_test.dart
@@ -0,0 +1,19 @@
+// Copyright 2014 The Flutter Authors. All rights reserved.
+// Use of this source code is governed by a BSD-style license that can be
+// found in the LICENSE file.
+
+import 'dart:html' as html;
+Future<void> main() async {
+  final html.ServiceWorkerRegistration worker = await html.window.navigator.serviceWorker.ready;
+  if (worker.active != null) {
+    await Future.delayed(const Duration(seconds: 5));
+    await html.HttpRequest.getString('CLOSE');
+    return;
+  }
+  worker.addEventListener('statechange', (event) async {
+    if (worker.active != null) {
+      await Future.delayed(const Duration(seconds: 5));
+      await html.HttpRequest.getString('CLOSE');
+    }
+  });
+}
diff --git a/dev/integration_tests/web/pubspec.yaml b/dev/integration_tests/web/pubspec.yaml
index eae11e0821..f7f63a5475 100644
--- a/dev/integration_tests/web/pubspec.yaml
+++ b/dev/integration_tests/web/pubspec.yaml
@@ -5,6 +5,11 @@ environment:
   # The pub client defaults to an <2.0.0 sdk constraint which we need to explicitly overwrite.
   sdk: ">=2.6.0 <3.0.0"
 
+flutter:
+  assets:
+    - lib/a.dart
+    - lib/b.dart
+
 dependencies:
   flutter:
     sdk: flutter
diff --git a/dev/integration_tests/web/web/index.html b/dev/integration_tests/web/web/index.html
index b7944c9e9e..fa7ef71069 100644
--- a/dev/integration_tests/web/web/index.html
+++ b/dev/integration_tests/web/web/index.html
@@ -2,12 +2,25 @@
 <!-- Copyright 2014 The Flutter Authors. All rights reserved.
 Use of this source code is governed by a BSD-style license that can be
 found in the LICENSE file. -->
-<html lang="en">
+<html>
 <head>
   <meta charset="UTF-8">
-  <title>web_integration</title>
-  <script defer src="main.dart.js" type="application/javascript"></script>
+  <meta content="IE=Edge" http-equiv="X-UA-Compatible">
+
+  <title>Web Test</title>
+  <link rel="manifest" href="manifest.json">
 </head>
 <body>
+  <!-- This script installs service_worker.js to provide PWA functionality to
+  application. For more information, see:
+  https://developers.google.com/web/fundamentals/primers/service-workers -->
+  <script>
+    if ('serviceWorker' in navigator) {
+      window.addEventListener('load', function () {
+        navigator.serviceWorker.register('flutter_service_worker.js');
+      });
+    }
+  </script>
+  <script src="main.dart.js" type="application/javascript"></script>
 </body>
 </html>
diff --git a/dev/integration_tests/web/web/manifest.json b/dev/integration_tests/web/web/manifest.json
new file mode 100644
index 0000000000..79c2cea0a9
--- /dev/null
+++ b/dev/integration_tests/web/web/manifest.json
@@ -0,0 +1,12 @@
+{
+    "name": "web_integration_test",
+    "short_name": "web_integration_test",
+    "start_url": ".",
+    "display": "standalone",
+    "background_color": "#0175C2",
+    "theme_color": "#0175C2",
+    "description": "A new Flutter project.",
+    "orientation": "portrait-primary",
+    "prefer_related_applications": false,
+    "icons": []
+}
diff --git a/packages/flutter_tools/lib/src/build_system/targets/web.dart b/packages/flutter_tools/lib/src/build_system/targets/web.dart
index e640ed2b46..be58660935 100644
--- a/packages/flutter_tools/lib/src/build_system/targets/web.dart
+++ b/packages/flutter_tools/lib/src/build_system/targets/web.dart
@@ -378,11 +378,12 @@ class WebServiceWorker extends Target {
       .childFile('flutter_service_worker.js');
     final Depfile depfile = Depfile(contents, <File>[serviceWorkerFile]);
     final String serviceWorker = generateServiceWorker(urlToHash, <String>[
-      'main.dart.js',
       '/',
+      'main.dart.js',
       'index.html',
       'assets/LICENSE',
-      'assets/AssetManifest.json',
+      if (urlToHash.containsKey('assets/AssetManifest.json'))
+        'assets/AssetManifest.json',
       if (urlToHash.containsKey('assets/FontManifest.json'))
         'assets/FontManifest.json',
     ]);
@@ -424,7 +425,8 @@ const CORE = [
 self.addEventListener("install", (event) => {
   return event.waitUntil(
     caches.open(TEMP).then((cache) => {
-      return cache.addAll(CORE);
+      // Provide a no-cache param to ensure the latest version is downloaded.
+      return cache.addAll(CORE.map((value) => new Request(value, {'cache': 'no-cache'})));
     })
   );
 });
@@ -443,6 +445,7 @@ self.addEventListener("activate", function(event) {
       // When there is no prior manifest, clear the entire cache.
       if (!manifest) {
         await caches.delete(CACHE_NAME);
+        contentCache = await caches.open(CACHE_NAME);
         for (var request of await tempCache.keys()) {
           var response = await tempCache.match(request);
           await contentCache.put(request, response);
@@ -492,6 +495,10 @@ self.addEventListener("activate", function(event) {
 self.addEventListener("fetch", (event) => {
   var origin = self.location.origin;
   var key = event.request.url.substring(origin.length + 1);
+  // Redirect URLs to the index.html
+  if (event.request.url == origin || event.request.url.startsWith(origin + '/#')) {
+    key = '/';
+  }
   // If the URL is not the the RESOURCE list, skip the cache.
   if (!RESOURCES[key]) {
     return event.respondWith(fetch(event.request));
@@ -500,8 +507,10 @@ self.addEventListener("fetch", (event) => {
     .then((cache) =>  {
       return cache.match(event.request).then((response) => {
         // Either respond with the cached resource, or perform a fetch and
-        // lazily populate the cache.
-        return response || fetch(event.request).then((response) => {
+        // lazily populate the cache. Ensure the resources are not cached
+        // by the browser for longer than the service worker expects.
+        var modifiedRequest = new Request(event.request, {'cache': 'no-cache'});
+        return response || fetch(modifiedRequest).then((response) => {
           cache.put(event.request, response.clone());
           return response;
         });
@@ -510,5 +519,37 @@ self.addEventListener("fetch", (event) => {
   );
 });
 
+self.addEventListener('message', (event) => {
+  // SkipWaiting can be used to immediately activate a waiting service worker.
+  // This will also require a page refresh triggered by the main worker.
+  if (event.message == 'skipWaiting') {
+    return self.skipWaiting();
+  }
+
+  if (event.message = 'downloadOffline') {
+    downloadOffline();
+  }
+});
+
+// Download offline will check the RESOURCES for all files not in the cache
+// and populate them.
+async function downloadOffline() {
+  var resources = [];
+  var contentCache = await caches.open(CACHE_NAME);
+  var currentContent = {};
+  for (var request of await contentCache.keys()) {
+    var key = request.url.substring(origin.length + 1);
+    if (key == "") {
+      key = "/";
+    }
+    currentContent[key] = true;
+  }
+  for (var resourceKey in Object.keys(RESOURCES)) {
+    if (!currentContent[resourceKey]) {
+      resources.add(resourceKey);
+    }
+  }
+  return Cache.addAll(resources);
+}
 ''';
 }