diff --git a/packages/flutter/test/material/radio_list_tile_test.dart b/packages/flutter/test/material/radio_list_tile_test.dart
index 3cc02199f93c0..ccf5f951d3397 100644
--- a/packages/flutter/test/material/radio_list_tile_test.dart
+++ b/packages/flutter/test/material/radio_list_tile_test.dart
@@ -2285,7 +2285,9 @@ void main() {
     const BorderSide side = BorderSide(color: Colors.red, width: 3.0);
     await tester.pumpWidget(
       const MaterialApp(
-        home: Material(child: Center(child: RadioListTile<bool>(value: true, radioSide: side))),
+        home: Material(
+          child: Center(child: RadioListTile<bool>(value: true, radioSide: side)),
+        ),
       ),
     );
 
diff --git a/packages/flutter/test/widgets/tap_region_test.dart b/packages/flutter/test/widgets/tap_region_test.dart
index 87cf705a60f19..406ee7552de3f 100644
--- a/packages/flutter/test/widgets/tap_region_test.dart
+++ b/packages/flutter/test/widgets/tap_region_test.dart
@@ -1201,18 +1201,17 @@ void main() {
                   Navigator.push(
                     tester.element(find.byType(GestureDetector)),
                     MaterialPageRoute<void>(
-                      builder:
-                          (BuildContext context) => Scaffold(
-                            body: Center(
-                              child: ElevatedButton(
-                                key: buttonKey,
-                                onPressed: () {
-                                  buttonTapped = true;
-                                },
-                                child: const Text('Test Button'),
-                              ),
-                            ),
+                      builder: (BuildContext context) => Scaffold(
+                        body: Center(
+                          child: ElevatedButton(
+                            key: buttonKey,
+                            onPressed: () {
+                              buttonTapped = true;
+                            },
+                            child: const Text('Test Button'),
                           ),
+                        ),
+                      ),
                     ),
                   );
                 },
diff --git a/packages/flutter_tools/lib/src/commands/drive.dart b/packages/flutter_tools/lib/src/commands/drive.dart
index 576e7b362d6d8..546262c427997 100644
--- a/packages/flutter_tools/lib/src/commands/drive.dart
+++ b/packages/flutter_tools/lib/src/commands/drive.dart
@@ -26,6 +26,7 @@ import '../drive/drive_service.dart';
 import '../drive/web_driver_service.dart' show Browser;
 import '../globals.dart' as globals;
 import '../ios/devices.dart';
+import '../isolated/devfs_config.dart';
 import '../resident_runner.dart';
 import '../runner/flutter_command.dart'
     show FlutterCommandCategory, FlutterCommandResult, FlutterOptions;
@@ -304,7 +305,14 @@ class DriveCommand extends RunCommandBase {
       _logger.printError('Screenshot not supported for ${device.displayName}.');
     }
 
-    final bool web = device is WebServerDevice || device is ChromiumDevice;
+    final DevConfig? devConfig = (device is WebServerDevice || device is ChromiumDevice)
+        ? await loadDevConfig(
+            hostname: stringArg('web-hostname'),
+            port: stringArg('web-port'),
+            tlsCertPath: stringArg('web-tls-cert-path'),
+            tlsCertKeyPath: stringArg('web-tls-cert-key-path'),
+          )
+        : null;
     _flutterDriverFactory ??= FlutterDriverFactory(
       applicationPackageFactory: ApplicationPackageFactory.instance!,
       logger: _logger,
@@ -322,9 +330,11 @@ class DriveCommand extends RunCommandBase {
       logger: _logger,
       throwOnError: false,
     );
-    final DriverService driverService = _flutterDriverFactory!.createDriverService(web);
+    final DriverService driverService = _flutterDriverFactory!.createDriverService(
+      devConfig != null,
+    );
     final BuildInfo buildInfo = await getBuildInfo();
-    final DebuggingOptions debuggingOptions = await createDebuggingOptions(web);
+    final DebuggingOptions debuggingOptions = await createDebuggingOptions(devConfig: devConfig);
     final File? applicationBinary = applicationBinaryPath == null
         ? null
         : _fileSystem.file(applicationBinaryPath);
@@ -342,7 +352,7 @@ class DriveCommand extends RunCommandBase {
           mainPath: targetFile,
           platformArgs: <String, Object>{
             if (traceStartup) 'trace-startup': traceStartup,
-            if (web) '--no-launch-chrome': true,
+            if (devConfig != null) '--no-launch-chrome': true,
           },
         );
       } else {
diff --git a/packages/flutter_tools/lib/src/commands/run.dart b/packages/flutter_tools/lib/src/commands/run.dart
index 458ed3e1cee8e..72d1e66c317d5 100644
--- a/packages/flutter_tools/lib/src/commands/run.dart
+++ b/packages/flutter_tools/lib/src/commands/run.dart
@@ -17,6 +17,7 @@ import '../device.dart';
 import '../features.dart';
 import '../globals.dart' as globals;
 import '../ios/devices.dart';
+import '../isolated/devfs_config.dart';
 import '../project.dart';
 import '../resident_runner.dart';
 import '../run_cold.dart';
@@ -269,7 +270,7 @@ abstract class RunCommandBase extends FlutterCommand with DeviceBasedDevelopment
   /// Create a debugging options instance for the current `run` or `drive` invocation.
   @visibleForTesting
   @protected
-  Future<DebuggingOptions> createDebuggingOptions(bool webMode) async {
+  Future<DebuggingOptions> createDebuggingOptions({DevConfig? devConfig}) async {
     final BuildInfo buildInfo = await getBuildInfo();
     final int? webBrowserDebugPort =
         featureFlags.isWebEnabled && argResults!.wasParsed('web-browser-debug-port')
@@ -279,18 +280,10 @@ abstract class RunCommandBase extends FlutterCommand with DeviceBasedDevelopment
         ? stringsArg(FlutterOptions.kWebBrowserFlag)
         : const <String>[];
 
-    final Map<String, String> webHeaders = featureFlags.isWebEnabled
-        ? extractWebHeaders()
-        : const <String, String>{};
-
     if (buildInfo.mode.isRelease) {
       return DebuggingOptions.disabled(
         buildInfo,
         dartEntrypointArgs: stringsArg('dart-entrypoint-args'),
-        hostname: featureFlags.isWebEnabled ? stringArg('web-hostname') : '',
-        port: featureFlags.isWebEnabled ? stringArg('web-port') : '',
-        tlsCertPath: featureFlags.isWebEnabled ? stringArg('web-tls-cert-path') : null,
-        tlsCertKeyPath: featureFlags.isWebEnabled ? stringArg('web-tls-cert-key-path') : null,
         webUseSseForDebugProxy:
             featureFlags.isWebEnabled && stringArg('web-server-debug-protocol') == 'sse',
         webUseSseForDebugBackend:
@@ -302,7 +295,6 @@ abstract class RunCommandBase extends FlutterCommand with DeviceBasedDevelopment
         webRunHeadless: featureFlags.isWebEnabled && boolArg('web-run-headless'),
         webBrowserDebugPort: webBrowserDebugPort,
         webBrowserFlags: webBrowserFlags,
-        webHeaders: webHeaders,
         webRenderer: webRenderer,
         webUseWasm: useWasm,
         enableImpeller: enableImpeller,
@@ -313,6 +305,7 @@ abstract class RunCommandBase extends FlutterCommand with DeviceBasedDevelopment
         enableEmbedderApi: enableEmbedderApi,
         usingCISystem: usingCISystem,
         debugLogsDirectoryPath: debugLogsDirectoryPath,
+        devConfig: devConfig,
       );
     } else {
       return DebuggingOptions.enabled(
@@ -344,10 +337,6 @@ abstract class RunCommandBase extends FlutterCommand with DeviceBasedDevelopment
         ddsPort: ddsPort,
         devToolsServerAddress: devToolsServerAddress,
         verboseSystemLogs: boolArg('verbose-system-logs'),
-        hostname: featureFlags.isWebEnabled ? stringArg('web-hostname') : '',
-        port: featureFlags.isWebEnabled ? stringArg('web-port') : '',
-        tlsCertPath: featureFlags.isWebEnabled ? stringArg('web-tls-cert-path') : null,
-        tlsCertKeyPath: featureFlags.isWebEnabled ? stringArg('web-tls-cert-key-path') : null,
         webUseSseForDebugProxy:
             featureFlags.isWebEnabled && stringArg('web-server-debug-protocol') == 'sse',
         webUseSseForDebugBackend:
@@ -362,7 +351,6 @@ abstract class RunCommandBase extends FlutterCommand with DeviceBasedDevelopment
         webEnableExpressionEvaluation:
             featureFlags.isWebEnabled && boolArg('web-enable-expression-evaluation'),
         webLaunchUrl: featureFlags.isWebEnabled ? stringArg('web-launch-url') : null,
-        webHeaders: webHeaders,
         webRenderer: webRenderer,
         webUseWasm: useWasm,
         vmserviceOutFile: stringArg('vmservice-out-file'),
@@ -382,6 +370,7 @@ abstract class RunCommandBase extends FlutterCommand with DeviceBasedDevelopment
         enableDevTools: boolArg(FlutterCommand.kEnableDevTools),
         ipv6: boolArg(FlutterCommand.ipv6Flag),
         printDtd: boolArg(FlutterGlobalOptions.kPrintDtd, global: true),
+        devConfig: devConfig,
       );
     }
   }
@@ -493,7 +482,7 @@ class RunCommand extends RunCommandBase {
   String get category => FlutterCommandCategory.project;
 
   List<Device>? devices;
-  var webMode = false;
+  late final DevConfig? _devConfig;
 
   String? get userIdentifier => stringArg(FlutterOptions.kDeviceUser);
 
@@ -663,12 +652,21 @@ class RunCommand extends RunCommandBase {
 
     // Only support "web mode" with a single web device due to resident runner
     // refactoring required otherwise.
-    webMode =
-        featureFlags.isWebEnabled &&
+    if (featureFlags.isWebEnabled &&
         devices!.length == 1 &&
-        await devices!.single.targetPlatform == TargetPlatform.web_javascript;
+        await devices!.single.targetPlatform == TargetPlatform.web_javascript) {
+      _devConfig = await loadDevConfig(
+        hostname: stringArg('web-hostname'),
+        port: stringArg('web-port'),
+        tlsCertPath: stringArg('web-tls-cert-path'),
+        tlsCertKeyPath: stringArg('web-tls-cert-key-path'),
+        headers: extractWebHeaders(),
+      );
+    } else {
+      _devConfig = null;
+    }
 
-    if (useWasm && !webMode) {
+    if (useWasm && _devConfig == null) {
       throwToolExit('--wasm is only supported on the web platform');
     }
 
@@ -696,11 +694,13 @@ class RunCommand extends RunCommandBase {
     required String? applicationBinaryPath,
     required FlutterProject flutterProject,
   }) async {
-    if (hotMode && !webMode) {
+    final DebuggingOptions debuggingOptions = await createDebuggingOptions(devConfig: _devConfig);
+
+    if (hotMode && _devConfig == null) {
       return HotRunner(
         flutterDevices,
         target: targetFile,
-        debuggingOptions: await createDebuggingOptions(webMode),
+        debuggingOptions: debuggingOptions,
         benchmarkMode: boolArg('benchmark'),
         applicationBinary: applicationBinaryPath == null
             ? null
@@ -711,12 +711,12 @@ class RunCommand extends RunCommandBase {
         analytics: globals.analytics,
         nativeAssetsYamlFile: stringArg(FlutterOptions.kNativeAssetsYamlFile),
       );
-    } else if (webMode) {
+    } else if (_devConfig != null) {
       return webRunnerFactory!.createWebRunner(
         flutterDevices.single,
         target: targetFile,
         flutterProject: flutterProject,
-        debuggingOptions: await createDebuggingOptions(webMode),
+        debuggingOptions: debuggingOptions,
         stayResident: stayResident,
         fileSystem: globals.fs,
         analytics: globals.analytics,
@@ -730,7 +730,7 @@ class RunCommand extends RunCommandBase {
     return ColdRunner(
       flutterDevices,
       target: targetFile,
-      debuggingOptions: await createDebuggingOptions(webMode),
+      debuggingOptions: debuggingOptions,
       traceStartup: traceStartup,
       awaitFirstFrameWhenTracing: awaitFirstFrameWhenTracing,
       applicationBinary: applicationBinaryPath == null
@@ -759,13 +759,15 @@ class RunCommand extends RunCommandBase {
       }
       final Daemon daemon = createMachineDaemon();
       late AppInstance app;
+
+      final DebuggingOptions debuggingOptions = await createDebuggingOptions(devConfig: _devConfig);
       try {
         app = await daemon.appDomain.startApp(
           devices!.first,
           globals.fs.currentDirectory.path,
           targetFile,
           route,
-          await createDebuggingOptions(webMode),
+          debuggingOptions,
           hotMode,
           applicationBinary: applicationBinaryPath == null
               ? null
diff --git a/packages/flutter_tools/lib/src/device.dart b/packages/flutter_tools/lib/src/device.dart
index a7320df0bfb9e..48222eabeb88d 100644
--- a/packages/flutter_tools/lib/src/device.dart
+++ b/packages/flutter_tools/lib/src/device.dart
@@ -17,6 +17,7 @@ import 'build_info.dart';
 import 'devfs.dart';
 import 'device_port_forwarder.dart';
 import 'device_vm_service_discovery_for_attach.dart';
+import 'isolated/devfs_config.dart';
 import 'project.dart';
 import 'vmservice.dart';
 import 'web/compile.dart';
@@ -948,10 +949,6 @@ class DebuggingOptions {
     this.deviceVmServicePort,
     this.ddsPort,
     this.devToolsServerAddress,
-    this.hostname,
-    this.port,
-    this.tlsCertPath,
-    this.tlsCertKeyPath,
     this.webEnableExposeUrl,
     this.webUseSseForDebugProxy = true,
     this.webUseSseForDebugBackend = true,
@@ -960,7 +957,6 @@ class DebuggingOptions {
     this.webBrowserDebugPort,
     this.webBrowserFlags = const <String>[],
     this.webEnableExpressionEvaluation = false,
-    this.webHeaders = const <String, String>{},
     this.webLaunchUrl,
     WebRendererMode? webRenderer,
     this.webUseWasm = false,
@@ -979,16 +975,13 @@ class DebuggingOptions {
     this.ipv6 = false,
     this.google3WorkspaceRoot,
     this.printDtd = false,
+    this.devConfig = const DevConfig(),
   }) : debuggingEnabled = true,
        webRenderer = webRenderer ?? WebRendererMode.getDefault(useWasm: webUseWasm);
 
   DebuggingOptions.disabled(
     this.buildInfo, {
     this.dartEntrypointArgs = const <String>[],
-    this.port,
-    this.hostname,
-    this.tlsCertPath,
-    this.tlsCertKeyPath,
     this.webEnableExposeUrl,
     this.webUseSseForDebugProxy = true,
     this.webUseSseForDebugBackend = true,
@@ -997,7 +990,6 @@ class DebuggingOptions {
     this.webBrowserDebugPort,
     this.webBrowserFlags = const <String>[],
     this.webLaunchUrl,
-    this.webHeaders = const <String, String>{},
     WebRendererMode? webRenderer,
     this.webUseWasm = false,
     this.traceAllowlist,
@@ -1009,6 +1001,7 @@ class DebuggingOptions {
     this.enableEmbedderApi = false,
     this.usingCISystem = false,
     this.debugLogsDirectoryPath,
+    this.devConfig = const DevConfig(),
   }) : debuggingEnabled = false,
        useTestFonts = false,
        startPaused = false,
@@ -1067,10 +1060,6 @@ class DebuggingOptions {
     required this.disablePortPublication,
     required this.ddsPort,
     required this.devToolsServerAddress,
-    required this.port,
-    required this.hostname,
-    required this.tlsCertPath,
-    required this.tlsCertKeyPath,
     required this.webEnableExposeUrl,
     required this.webUseSseForDebugProxy,
     required this.webUseSseForDebugBackend,
@@ -1079,7 +1068,6 @@ class DebuggingOptions {
     required this.webBrowserDebugPort,
     required this.webBrowserFlags,
     required this.webEnableExpressionEvaluation,
-    required this.webHeaders,
     required this.webLaunchUrl,
     required this.webRenderer,
     required this.webUseWasm,
@@ -1098,6 +1086,8 @@ class DebuggingOptions {
     required this.ipv6,
     required this.google3WorkspaceRoot,
     required this.printDtd,
+    // ignore: unused_element_parameter
+    this.devConfig,
   });
 
   final bool debuggingEnabled;
@@ -1126,10 +1116,6 @@ class DebuggingOptions {
   final bool disablePortPublication;
   final int? ddsPort;
   final Uri? devToolsServerAddress;
-  final String? port;
-  final String? hostname;
-  final String? tlsCertPath;
-  final String? tlsCertKeyPath;
   final bool? webEnableExposeUrl;
   final bool webUseSseForDebugProxy;
   final bool webUseSseForDebugBackend;
@@ -1145,6 +1131,7 @@ class DebuggingOptions {
   final bool ipv6;
   final String? google3WorkspaceRoot;
   final bool printDtd;
+  final DevConfig? devConfig;
 
   /// Whether the tool should try to uninstall a previously installed version of the app.
   ///
@@ -1170,9 +1157,6 @@ class DebuggingOptions {
   /// Allow developers to customize the browser's launch URL
   final String? webLaunchUrl;
 
-  /// Allow developers to add custom headers to web server
-  final Map<String, String> webHeaders;
-
   /// Which web renderer to use for the debugging session
   final WebRendererMode webRenderer;
 
@@ -1268,10 +1252,6 @@ class DebuggingOptions {
     'disablePortPublication': disablePortPublication,
     'ddsPort': ddsPort,
     'devToolsServerAddress': devToolsServerAddress.toString(),
-    'port': port,
-    'hostname': hostname,
-    'tlsCertPath': tlsCertPath,
-    'tlsCertKeyPath': tlsCertKeyPath,
     'webEnableExposeUrl': webEnableExposeUrl,
     'webUseSseForDebugProxy': webUseSseForDebugProxy,
     'webUseSseForDebugBackend': webUseSseForDebugBackend,
@@ -1281,7 +1261,6 @@ class DebuggingOptions {
     'webBrowserFlags': webBrowserFlags,
     'webEnableExpressionEvaluation': webEnableExpressionEvaluation,
     'webLaunchUrl': webLaunchUrl,
-    'webHeaders': webHeaders,
     'webRenderer': webRenderer.name,
     'webUseWasm': webUseWasm,
     'vmserviceOutFile': vmserviceOutFile,
@@ -1337,10 +1316,6 @@ class DebuggingOptions {
         devToolsServerAddress: json['devToolsServerAddress'] != null
             ? Uri.parse(json['devToolsServerAddress']! as String)
             : null,
-        port: json['port'] as String?,
-        hostname: json['hostname'] as String?,
-        tlsCertPath: json['tlsCertPath'] as String?,
-        tlsCertKeyPath: json['tlsCertKeyPath'] as String?,
         webEnableExposeUrl: json['webEnableExposeUrl'] as bool?,
         webUseSseForDebugProxy: json['webUseSseForDebugProxy']! as bool,
         webUseSseForDebugBackend: json['webUseSseForDebugBackend']! as bool,
@@ -1349,7 +1324,6 @@ class DebuggingOptions {
         webBrowserDebugPort: json['webBrowserDebugPort'] as int?,
         webBrowserFlags: (json['webBrowserFlags']! as List<dynamic>).cast<String>(),
         webEnableExpressionEvaluation: json['webEnableExpressionEvaluation']! as bool,
-        webHeaders: (json['webHeaders']! as Map<dynamic, dynamic>).cast<String, String>(),
         webLaunchUrl: json['webLaunchUrl'] as String?,
         webRenderer: WebRendererMode.values.byName(json['webRenderer']! as String),
         webUseWasm: json['webUseWasm']! as bool,
diff --git a/packages/flutter_tools/lib/src/drive/web_driver_service.dart b/packages/flutter_tools/lib/src/drive/web_driver_service.dart
index 27fde99423dd0..cd8eb3c27290e 100644
--- a/packages/flutter_tools/lib/src/drive/web_driver_service.dart
+++ b/packages/flutter_tools/lib/src/drive/web_driver_service.dart
@@ -85,20 +85,16 @@ class WebDriverService extends DriverService {
       debuggingOptions: buildInfo.isRelease
           ? DebuggingOptions.disabled(
               buildInfo,
-              port: debuggingOptions.port,
-              hostname: debuggingOptions.hostname,
+              devConfig: debuggingOptions.devConfig,
               webRenderer: debuggingOptions.webRenderer,
               webUseWasm: debuggingOptions.webUseWasm,
-              webHeaders: debuggingOptions.webHeaders,
             )
           : DebuggingOptions.enabled(
               buildInfo,
-              port: debuggingOptions.port,
-              hostname: debuggingOptions.hostname,
+              devConfig: debuggingOptions.devConfig,
               disablePortPublication: debuggingOptions.disablePortPublication,
               webRenderer: debuggingOptions.webRenderer,
               webUseWasm: debuggingOptions.webUseWasm,
-              webHeaders: debuggingOptions.webHeaders,
             ),
       stayResident: true,
       flutterProject: FlutterProject.current(),
diff --git a/packages/flutter_tools/lib/src/isolated/devfs_config.dart b/packages/flutter_tools/lib/src/isolated/devfs_config.dart
new file mode 100644
index 0000000000000..592e7f66a04a5
--- /dev/null
+++ b/packages/flutter_tools/lib/src/isolated/devfs_config.dart
@@ -0,0 +1,261 @@
+// 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' as io;
+
+import 'package:meta/meta.dart';
+import 'package:source_span/source_span.dart';
+import 'package:yaml/yaml.dart';
+
+import '../base/common.dart';
+import '../globals.dart' as globals;
+import 'devfs_proxy.dart';
+
+const devConfigFilePath = 'web_dev_config.yaml';
+
+@immutable
+class DevConfig {
+  const DevConfig({
+    this.headers = const <String, String>{},
+    this.host = 'any',
+    this.port,
+    this.https,
+    this.proxy = const <ProxyRule>[],
+  });
+
+  factory DevConfig.fromYaml(YamlMap yaml) {
+    final headers = <String, String>{};
+    if (yaml['headers'] != null) {
+      if (yaml['headers'] is! YamlList) {
+        throwToolExit('Headers must be a List of maps. Found ${yaml['headers'].runtimeType}');
+      }
+      final headersList = yaml['headers'] as YamlList;
+      for (final dynamic item in headersList) {
+        if (item is! YamlMap) {
+          throwToolExit(
+            'Each header entry must be a map with "name" and "value" keys. Found ${item.runtimeType}',
+          );
+        }
+        final YamlMap headerMap = item;
+        if (!headerMap.containsKey('name') || !headerMap.containsKey('value')) {
+          throwToolExit('Each header entry must contain "name" and "value" keys.');
+        }
+        final dynamic name = headerMap['name'];
+        final dynamic value = headerMap['value'];
+
+        if (name is! String || value is! String) {
+          throwToolExit(
+            'Header "name" and "value" must be strings. Found name: ${name.runtimeType}, value: ${value.runtimeType}',
+          );
+        }
+        headers[name] = value;
+      }
+    }
+    if (yaml['host'] is! String && yaml['host'] != null) {
+      throwToolExit('Host must be a String. Found ${yaml['host'].runtimeType}');
+    }
+    if (yaml['port'] is! int && yaml['port'] != null) {
+      throwToolExit('Port must be an int. Found ${yaml['port'].runtimeType}');
+    }
+    if (yaml['https'] is! YamlMap && yaml['https'] != null) {
+      throwToolExit('Https must be a Map. Found ${yaml['https'].runtimeType}');
+    }
+
+    final proxyRules = <ProxyRule>[];
+    if (yaml['proxy'] != null) {
+      if (yaml['proxy'] is! YamlList) {
+        throwToolExit('Proxy must be a list. Found ${yaml['proxy'].runtimeType}');
+      }
+      final proxyList = yaml['proxy'] as YamlList;
+      for (final dynamic item in proxyList) {
+        if (item is YamlMap) {
+          final ProxyRule? rule = ProxyRule.fromYaml(item);
+          if (rule != null) {
+            proxyRules.add(rule);
+          }
+        }
+      }
+    }
+
+    return DevConfig(
+      headers: headers,
+      host: yaml['host'] as String?,
+      port: yaml['port'] as int?,
+      https: yaml['https'] == null ? null : HttpsConfig.fromYaml(yaml['https'] as YamlMap),
+      proxy: proxyRules,
+    );
+  }
+
+  final Map<String, String> headers;
+  final String? host;
+  final int? port;
+  final HttpsConfig? https;
+  final List<ProxyRule> proxy;
+
+  @override
+  String toString() {
+    return '''
+  DevConfig:
+  headers: $headers
+  host: $host
+  port: $port
+  https: $https
+  proxy: $proxy''';
+  }
+}
+
+@immutable
+class HttpsConfig {
+  const HttpsConfig({required this.certPath, required this.certKeyPath});
+
+  factory HttpsConfig.fromYaml(YamlMap yaml) {
+    if (yaml['cert-path'] is! String && yaml['cert-path'] != null) {
+      throwToolExit('Https cert-path must be a String. Found ${yaml['cert-path'].runtimeType}');
+    }
+    if (yaml['cert-key-path'] is! String && yaml['cert-key-path'] != null) {
+      throwToolExit(
+        'Https cert-key-path must be a String. Found ${yaml['cert-key-path'].runtimeType}',
+      );
+    }
+    return HttpsConfig(
+      certPath: yaml['cert-path'] as String?,
+      certKeyPath: yaml['cert-key-path'] as String?,
+    );
+  }
+
+  final String? certPath;
+  final String? certKeyPath;
+
+  @override
+  String toString() {
+    return '''
+    HttpsConfig:
+        certPath: $certPath
+        certKeyPath: $certKeyPath''';
+  }
+}
+
+T? _getOverriddenValue<T>(String filedName, T? fileValue, T? cliValue) {
+  if (cliValue != null) {
+    if (fileValue != null && cliValue != fileValue) {
+      globals.printStatus(
+        'Overriding $filedName from $devConfigFilePath ($fileValue) with command-line argument ($cliValue)',
+      );
+    }
+    return cliValue;
+  }
+  return fileValue;
+}
+
+Future<DevConfig> loadDevConfig({
+  String? hostname,
+  String? port,
+  String? tlsCertPath,
+  String? tlsCertKeyPath,
+  Map<String, String>? headers,
+  int? debugPort,
+  List<String>? browserFlags,
+}) async {
+  final io.File devConfigFile = globals.fs.file(devConfigFilePath);
+  var fileConfig = const DevConfig();
+
+  if (!devConfigFile.existsSync()) {
+    globals.printStatus('No $devConfigFilePath found');
+  } else {
+    try {
+      final String devConfigContent = await devConfigFile.readAsString();
+      final YamlDocument yamlDoc = loadYamlDocument(devConfigContent);
+      final YamlNode contents = yamlDoc.contents;
+      if (contents is! YamlMap) {
+        throw YamlException(
+          '$devConfigFilePath file found, but it must be a YAML map (e.g., "server:"). Found a ${contents.runtimeType} instead.',
+          contents.span,
+        );
+      }
+
+      if (!contents.containsKey('server') || contents['server'] is! YamlMap) {
+        final SourceSpan span = (contents.containsKey('server') && contents['server'] is YamlNode)
+            ? (contents['server'] as YamlNode).span
+            : contents.span;
+        throw YamlException(
+          '"$devConfigFilePath" file found, but the "server" key is missing or malformed. It must be a YAML map.',
+          span,
+        );
+      }
+
+      final serverYaml = contents['server'] as YamlMap;
+      fileConfig = DevConfig.fromYaml(serverYaml);
+      globals.printStatus('\nLoaded configuration from $devConfigFilePath');
+      globals.printTrace(fileConfig.toString());
+    } on YamlException catch (e) {
+      globals.printError('Error: Failed to parse $devConfigFilePath: ${e.message} ${e.span}');
+      rethrow;
+    } on Exception catch (e) {
+      globals.printError('An unexpected error occurred while reading $devConfigFilePath: $e');
+      globals.printStatus(
+        'Reverting to default flutter_tools web server configuration due to unexpected error.',
+      );
+    }
+  }
+
+  final String finalHost =
+      _getOverriddenValue<String>('host', fileConfig.host, hostname) ?? 'localhost';
+  final int? finalPort = _getOverriddenValue<int>(
+    'port',
+    fileConfig.port,
+    port != null ? int.tryParse(port) : null,
+  );
+  final String? finalCertPath = _getOverriddenValue<String>(
+    'TLS cert path',
+    fileConfig.https?.certPath,
+    tlsCertPath,
+  );
+  final String? finalCertKeyPath = _getOverriddenValue<String>(
+    'TLS cert key path',
+    fileConfig.https?.certKeyPath,
+    tlsCertKeyPath,
+  );
+  HttpsConfig? finalHttpsConfig;
+  if (finalCertPath != null || finalCertKeyPath != null || fileConfig.https != null) {
+    finalHttpsConfig = HttpsConfig(certPath: finalCertPath, certKeyPath: finalCertKeyPath);
+  } else {
+    finalHttpsConfig = null;
+  }
+  final finalHeaders = <String, String>{};
+  finalHeaders.addAll(fileConfig.headers);
+  if (headers != null && headers.isNotEmpty) {
+    for (final MapEntry<String, String> entry in headers.entries) {
+      if (fileConfig.headers.containsKey(entry.key)) {
+        globals.printStatus(
+          'Overriding headers "${entry.key}" from $devConfigFilePath ("${fileConfig.headers[entry.key]}") with command-line argument("${entry.value}").',
+        );
+      } else {
+        globals.printStatus('Adding header "${entry.key}" from command-line arguments.');
+      }
+    }
+    finalHeaders.addAll(headers);
+  }
+
+  return DevConfig(
+    host: finalHost,
+    port: finalPort,
+    https: finalHttpsConfig,
+    headers: finalHeaders,
+    proxy: fileConfig.proxy,
+  );
+}
+
+Future<int> resolvePort(int? port) async {
+  if (port == null) {
+    return globals.os.findFreePort();
+  }
+  if (port < 0 || port > 65535) {
+    throwToolExit('''
+Invalid port: $port
+Please provide a valid TCP port (an integer between 0 and 65535, inclusive).
+''');
+  }
+  return port;
+}
diff --git a/packages/flutter_tools/lib/src/isolated/devfs_proxy.dart b/packages/flutter_tools/lib/src/isolated/devfs_proxy.dart
new file mode 100644
index 0000000000000..c8736ad6a22c1
--- /dev/null
+++ b/packages/flutter_tools/lib/src/isolated/devfs_proxy.dart
@@ -0,0 +1,164 @@
+// 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 'package:shelf/shelf.dart' as shelf;
+import 'package:shelf_proxy/shelf_proxy.dart';
+import 'package:yaml/yaml.dart';
+import '/src/base/logger.dart';
+import '../globals.dart' as globals;
+
+abstract class ProxyRule {
+  ProxyRule({required this.target});
+
+  final String target;
+  String replace(String path);
+  bool matches(String path);
+
+  static ProxyRule? fromYaml(YamlMap yaml, {Logger? logger}) {
+    final target = yaml['target'] as String?;
+    final source = yaml['source'] as String?;
+    final regex = yaml['regex'] as String?;
+    final replace = yaml['replace'] as String?;
+    final Logger effectiveLogger = logger ?? globals.logger;
+
+    if (target == null) {
+      final String? path = source ?? regex;
+      effectiveLogger.printError("Invalid 'target' for path: $path. 'target' cannot be null");
+      return null;
+    }
+    RegExp? proxyPattern;
+    if (source != null && source.isNotEmpty) {
+      return SourceProxyRule(source: source, target: target, replacement: replace?.trim());
+    } else if (regex != null && regex.isNotEmpty) {
+      try {
+        proxyPattern = RegExp(regex.trim());
+      } on FormatException catch (e) {
+        proxyPattern = RegExp(RegExp.escape(regex));
+        effectiveLogger.printWarning(
+          "Invalid regex pattern in replace 'regex': '$regex'. Treating $regex as string. Error: $e",
+        );
+      }
+      return RegexProxyRule(pattern: proxyPattern, target: target, replacement: replace?.trim());
+    } else {
+      effectiveLogger.printError("'source' or 'regex' field must be provided");
+      return null;
+    }
+  }
+}
+
+class RegexProxyRule extends ProxyRule {
+  RegexProxyRule({required this.pattern, required super.target, this.replacement});
+
+  final RegExp pattern;
+  final String? replacement;
+
+  @override
+  bool matches(String path) {
+    return pattern.hasMatch(path);
+  }
+
+  @override
+  String replace(String path) {
+    if (replacement == null) {
+      return path;
+    }
+    return path.replaceAllMapped(pattern, (Match match) {
+      String result = replacement!;
+
+      for (var i = 0; i <= match.groupCount; i++) {
+        result = result.replaceAll('\$$i', match.group(i) ?? '');
+      }
+      return result;
+    });
+  }
+
+  @override
+  String toString() {
+    return '{pattern: ${pattern.pattern}, target: $target, replacement: ${replacement ?? 'null'}}';
+  }
+}
+
+class SourceProxyRule extends ProxyRule {
+  SourceProxyRule({required this.source, required super.target, this.replacement});
+  final String source;
+  final String? replacement;
+
+  @override
+  bool matches(String path) {
+    return path.startsWith(source);
+  }
+
+  @override
+  String replace(String path) {
+    if (replacement == null) {
+      return path;
+    }
+    return path.replaceFirst(source, replacement!);
+  }
+
+  @override
+  String toString() {
+    return '{source: $source, target: $target, replacement: ${replacement ?? 'null'}}';
+  }
+}
+
+shelf.Request proxyRequest(shelf.Request originalRequest, Uri finalTargetUrl) {
+  return shelf.Request(
+    originalRequest.method,
+    finalTargetUrl,
+    headers: originalRequest.headers,
+    body: originalRequest.read(),
+    context: originalRequest.context,
+  );
+}
+
+String _normalizePath(String path) {
+  if (!path.startsWith('/')) {
+    path = '/$path';
+  }
+  return path;
+}
+
+shelf.Middleware proxyMiddleware(List<ProxyRule> effectiveProxy) {
+  return (shelf.Handler innerHandler) {
+    return (shelf.Request request) async {
+      final String requestPath = _normalizePath(request.url.path);
+      for (final rule in effectiveProxy) {
+        if (rule.matches(requestPath)) {
+          final Uri targetBaseUri = Uri.parse(rule.target);
+          final String rewrittenRequest = rule.replace(requestPath);
+          final Uri finalTargetUrl = targetBaseUri.resolve(rewrittenRequest);
+          try {
+            final shelf.Request proxyBackendRequest = proxyRequest(request, finalTargetUrl);
+            final shelf.Response proxyResponse = await proxyHandler(targetBaseUri)(
+              proxyBackendRequest,
+            );
+            final internalRequest = proxyResponse.headers['sec-fetch-mode'] == 'no-cors';
+            if (!internalRequest) {
+              globals.logger.printStatus(
+                '[PROXY] Matched "$requestPath". Requesting "$finalTargetUrl"',
+              );
+              globals.logger.printTrace('[PROXY] Matched with proxy rule: $rule');
+            }
+            if (proxyResponse.statusCode == 404) {
+              if (!internalRequest) {
+                globals.printTrace('"$finalTargetUrl" responded with status 404');
+              }
+              return innerHandler(request);
+            }
+            return proxyResponse;
+          } on Exception catch (e) {
+            globals.logger.printError(
+              'Proxy error for $finalTargetUrl: $e. Allowing fall-through.',
+            );
+
+            return innerHandler(request);
+          }
+        }
+      }
+
+      return innerHandler(request);
+    };
+  };
+}
diff --git a/packages/flutter_tools/lib/src/isolated/devfs_web.dart b/packages/flutter_tools/lib/src/isolated/devfs_web.dart
index cebd4a83c489e..6d11e427c4242 100644
--- a/packages/flutter_tools/lib/src/isolated/devfs_web.dart
+++ b/packages/flutter_tools/lib/src/isolated/devfs_web.dart
@@ -30,7 +30,7 @@ import '../web/bootstrap.dart';
 import '../web/chrome.dart';
 import '../web/compile.dart';
 import '../web_template.dart';
-
+import 'devfs_config.dart';
 import 'web_asset_server.dart';
 
 const kLuciEnvName = 'LUCI_CONTEXT';
@@ -60,10 +60,6 @@ class WebDevFS implements DevFS {
   /// [testMode] is true, do not actually initialize dwds or the shelf static
   /// server.
   WebDevFS({
-    required this.hostname,
-    required int port,
-    required this.tlsCertPath,
-    required this.tlsCertKeyPath,
     required this.packagesFilePath,
     required this.urlTunneller,
     required this.useSseForDebugProxy,
@@ -74,11 +70,11 @@ class WebDevFS implements DevFS {
     required this.enableDds,
     required this.entrypoint,
     required this.expressionCompiler,
-    required this.extraHeaders,
     required this.chromiumLauncher,
     required this.nativeNullAssertions,
     required this.ddcModuleSystem,
     required this.canaryFeatures,
+    required this.devConfig,
     required this.webRenderer,
     required this.isWasm,
     required this.useLocalCanvasKit,
@@ -88,7 +84,7 @@ class WebDevFS implements DevFS {
     required this.logger,
     required this.platform,
     this.testMode = false,
-  }) : _port = port {
+  }) {
     // TODO(srujzs): Remove this assertion when the library bundle format is
     // supported without canary mode.
     if (ddcModuleSystem) {
@@ -97,7 +93,6 @@ class WebDevFS implements DevFS {
   }
 
   final Uri entrypoint;
-  final String hostname;
   final String packagesFilePath;
   final UrlTunneller? urlTunneller;
   final bool useSseForDebugProxy;
@@ -106,19 +101,16 @@ class WebDevFS implements DevFS {
   final BuildInfo buildInfo;
   final bool enableDwds;
   final bool enableDds;
-  final Map<String, String> extraHeaders;
   final bool testMode;
   final bool ddcModuleSystem;
   final bool canaryFeatures;
   final ExpressionCompiler? expressionCompiler;
   final ChromiumLauncher? chromiumLauncher;
   final bool nativeNullAssertions;
-  final int _port;
-  final String? tlsCertPath;
-  final String? tlsCertKeyPath;
   final WebRendererMode webRenderer;
   final bool isWasm;
   final bool useLocalCanvasKit;
+  final DevConfig devConfig;
   final bool useDwdsWebSocketConnection;
   final FileSystem fileSystem;
   final Logger logger;
@@ -208,10 +200,6 @@ class WebDevFS implements DevFS {
   Future<Uri> create() async {
     webAssetServer = await WebAssetServer.start(
       chromiumLauncher,
-      hostname,
-      _port,
-      tlsCertPath,
-      tlsCertKeyPath,
       urlTunneller,
       useSseForDebugProxy,
       useSseForDebugBackend,
@@ -221,13 +209,13 @@ class WebDevFS implements DevFS {
       enableDds,
       entrypoint,
       expressionCompiler,
-      extraHeaders,
       webRenderer: webRenderer,
       isWasm: isWasm,
       useLocalCanvasKit: useLocalCanvasKit,
       testMode: testMode,
       ddcModuleSystem: ddcModuleSystem,
       canaryFeatures: canaryFeatures,
+      devConfig: devConfig,
       useDwdsWebSocketConnection: useDwdsWebSocketConnection,
       fileSystem: fileSystem,
       logger: logger,
diff --git a/packages/flutter_tools/lib/src/isolated/resident_web_runner.dart b/packages/flutter_tools/lib/src/isolated/resident_web_runner.dart
index 1570d18abee08..f49e86d790561 100644
--- a/packages/flutter_tools/lib/src/isolated/resident_web_runner.dart
+++ b/packages/flutter_tools/lib/src/isolated/resident_web_runner.dart
@@ -41,6 +41,8 @@ import '../web/file_generators/flutter_service_worker_js.dart';
 import '../web/file_generators/main_dart.dart' as main_dart;
 import '../web/web_device.dart';
 import '../web/web_runner.dart';
+
+import 'devfs_config.dart';
 import 'devfs_web.dart';
 import 'web_expression_compiler.dart';
 
@@ -274,31 +276,17 @@ class ResidentWebRunner extends ResidentRunner {
 
     try {
       return await asyncGuard(() async {
-        Future<int> getPort() async {
-          if (debuggingOptions.port == null) {
-            return globals.os.findFreePort();
-          }
+        final DevConfig originalDevConfig = debuggingOptions.devConfig ?? const DevConfig();
 
-          final int? port = int.tryParse(debuggingOptions.port ?? '');
-
-          if (port == null) {
-            logger.printError('''
-Received a non-integer value for port: ${debuggingOptions.port}
-A randomly-chosen available port will be used instead.
-''');
-            return globals.os.findFreePort();
-          }
-
-          if (port < 0 || port > 65535) {
-            throwToolExit('''
-Invalid port: ${debuggingOptions.port}
-Please provide a valid TCP port (an integer between 0 and 65535, inclusive).
-    ''');
-          }
-
-          return port;
-        }
+        final int resolvedPort = await resolvePort(originalDevConfig.port);
 
+        final updatedDevConfig = DevConfig(
+          host: originalDevConfig.host,
+          port: resolvedPort,
+          headers: originalDevConfig.headers,
+          https: originalDevConfig.https,
+          proxy: originalDevConfig.proxy,
+        );
         final ExpressionCompiler? expressionCompiler =
             debuggingOptions.webEnableExpressionEvaluation
             ? WebExpressionCompiler(device!.generator!, fileSystem: _fileSystem)
@@ -323,10 +311,7 @@ Please provide a valid TCP port (an integer between 0 and 65535, inclusive).
                 nonWebServerConnectedDeviceIds.contains(device!.device!.id));
 
         device!.devFS = WebDevFS(
-          hostname: debuggingOptions.hostname ?? 'localhost',
-          port: await getPort(),
-          tlsCertPath: debuggingOptions.tlsCertPath,
-          tlsCertKeyPath: debuggingOptions.tlsCertKeyPath,
+          devConfig: updatedDevConfig,
           packagesFilePath: packagesFilePath,
           urlTunneller: _urlTunneller,
           useSseForDebugProxy: debuggingOptions.webUseSseForDebugProxy,
@@ -337,7 +322,6 @@ Please provide a valid TCP port (an integer between 0 and 65535, inclusive).
           enableDds: debuggingOptions.enableDds,
           entrypoint: _fileSystem.file(target).uri,
           expressionCompiler: expressionCompiler,
-          extraHeaders: debuggingOptions.webHeaders,
           chromiumLauncher: _chromiumLauncher,
           nativeNullAssertions: debuggingOptions.nativeNullAssertions,
           ddcModuleSystem: debuggingOptions.buildInfo.ddcModuleFormat == DdcModuleFormat.ddc,
@@ -352,7 +336,8 @@ Please provide a valid TCP port (an integer between 0 and 65535, inclusive).
           platform: _platform,
         );
         Uri url = await device!.devFS!.create();
-        if (debuggingOptions.tlsCertKeyPath != null && debuggingOptions.tlsCertPath != null) {
+        if (debuggingOptions.devConfig!.https?.certKeyPath != null &&
+            debuggingOptions.devConfig!.https?.certPath != null) {
           url = url.replace(scheme: 'https');
         }
         if (debuggingOptions.buildInfo.isDebug && !debuggingOptions.webUseWasm) {
diff --git a/packages/flutter_tools/lib/src/isolated/web_asset_server.dart b/packages/flutter_tools/lib/src/isolated/web_asset_server.dart
index 982240a209847..4ba62ba72b57d 100644
--- a/packages/flutter_tools/lib/src/isolated/web_asset_server.dart
+++ b/packages/flutter_tools/lib/src/isolated/web_asset_server.dart
@@ -31,7 +31,8 @@ import '../web/compile.dart';
 import '../web/memory_fs.dart';
 import '../web/module_metadata.dart';
 import '../web_template.dart';
-
+import 'devfs_config.dart';
+import 'devfs_proxy.dart';
 import 'release_asset_server.dart';
 import 'web_server_utlities.dart';
 
@@ -134,9 +135,6 @@ class WebAssetServer implements AssetReader {
   /// contains a list of objects each with three fields:
   ///
   /// `src`: A string that corresponds to the file path containing a DDC library
-  /// bundle. To support embedded libraries, the path should include the
-  /// `baseUri` of the web server.
-  /// `module`: The name of the library bundle in `src`.
   /// `libraries`: An array of strings containing the libraries that were
   /// compiled in `src`.
   ///
@@ -179,7 +177,7 @@ class WebAssetServer implements AssetReader {
   Uri? get baseUri => _baseUri;
   Uri? _baseUri;
 
-  /// Start the web asset server on a [hostname] and [port].
+  /// Start the web asset server on a hostname and port.
   ///
   /// If [testMode] is true, do not actually initialize dwds or the shelf static
   /// server.
@@ -188,10 +186,6 @@ class WebAssetServer implements AssetReader {
   /// trace.
   static Future<WebAssetServer> start(
     ChromiumLauncher? chromiumLauncher,
-    String hostname,
-    int port,
-    String? tlsCertPath,
-    String? tlsCertKeyPath,
     UrlTunneller? urlTunneller,
     bool useSseForDebugProxy,
     bool useSseForDebugBackend,
@@ -200,8 +194,8 @@ class WebAssetServer implements AssetReader {
     bool enableDwds,
     bool enableDds,
     Uri entrypoint,
-    ExpressionCompiler? expressionCompiler,
-    Map<String, String> extraHeaders, {
+    ExpressionCompiler? expressionCompiler, {
+    required DevConfig devConfig,
     required WebRendererMode webRenderer,
     required bool isWasm,
     required bool useLocalCanvasKit,
@@ -216,28 +210,35 @@ class WebAssetServer implements AssetReader {
     required Platform platform,
     bool shouldEnableMiddleware = true,
   }) async {
+    final String effectiveHost = devConfig.host ?? 'localhost';
+    final int effectivePort = devConfig.port ?? 0;
+    final String? effectiveCertPath = devConfig.https?.certPath;
+    final String? effectiveCertKeyPath = devConfig.https?.certKeyPath;
+    final Map<String, String> effectiveHeaders = devConfig.headers;
+    final List<ProxyRule> effectiveProxy = devConfig.proxy;
+
     // TODO(srujzs): Remove this assertion when the library bundle format is
     // supported without canary mode.
     if (ddcModuleSystem) {
       assert(canaryFeatures);
     }
     InternetAddress address;
-    if (hostname == 'any') {
+    if (effectiveHost == 'any') {
       address = InternetAddress.anyIPv4;
     } else {
-      address = (await InternetAddress.lookup(hostname)).first;
+      address = (await InternetAddress.lookup(effectiveHost)).first;
     }
     HttpServer? httpServer;
     const kMaxRetries = 4;
     for (var i = 0; i <= kMaxRetries; i++) {
       try {
-        if (tlsCertPath != null && tlsCertKeyPath != null) {
+        if (effectiveCertPath != null && effectiveCertKeyPath != null) {
           final serverContext = SecurityContext()
-            ..useCertificateChain(tlsCertPath)
-            ..usePrivateKey(tlsCertKeyPath);
-          httpServer = await HttpServer.bindSecure(address, port, serverContext);
+            ..useCertificateChain(effectiveCertPath)
+            ..usePrivateKey(effectiveCertKeyPath);
+          httpServer = await HttpServer.bindSecure(address, effectivePort, serverContext);
         } else {
-          httpServer = await HttpServer.bind(address, port);
+          httpServer = await HttpServer.bind(address, effectivePort);
         }
         break;
       } on SocketException catch (e, s) {
@@ -252,7 +253,7 @@ class WebAssetServer implements AssetReader {
     // Allow rendering in a iframe.
     httpServer!.defaultResponseHeaders.remove('x-frame-options', 'SAMEORIGIN');
 
-    for (final MapEntry<String, String> header in extraHeaders.entries) {
+    for (final MapEntry<String, String> header in effectiveHeaders.entries) {
       httpServer.defaultResponseHeaders.add(header.key, header.value);
     }
 
@@ -271,13 +272,13 @@ class WebAssetServer implements AssetReader {
       useLocalCanvasKit: useLocalCanvasKit,
       fileSystem: fileSystem,
     );
-    final int selectedPort = server.selectedPort;
-    var url = '$hostname:$selectedPort';
-    if (hostname == 'any') {
+    final int selectedPort = httpServer.port;
+    var url = '$effectiveHost:$selectedPort';
+    if (effectiveHost == 'any') {
       url = 'localhost:$selectedPort';
     }
     server._baseUri = Uri.http(url, server.basePath);
-    if (tlsCertPath != null && tlsCertKeyPath != null) {
+    if (effectiveCertPath != null && effectiveCertKeyPath != null) {
       server._baseUri = Uri.https(url, server.basePath);
     }
     if (testMode) {
@@ -377,7 +378,7 @@ class WebAssetServer implements AssetReader {
           expressionCompiler: expressionCompiler,
           spawnDds: enableDds,
         ),
-        appMetadata: AppMetadata(hostname: hostname),
+        appMetadata: AppMetadata(hostname: effectiveHost),
       ),
       // Use DWDS WebSocket-based connection instead of Chrome-based connection for debugging
       useDwdsWebSocketConnection: useDwdsWebSocketConnection,
@@ -386,6 +387,7 @@ class WebAssetServer implements AssetReader {
     if (shouldEnableMiddleware) {
       pipeline = pipeline.addMiddleware(middleware).addMiddleware(dwds.middleware);
     }
+    pipeline = pipeline.addMiddleware(proxyMiddleware(effectiveProxy));
     final shelf.Handler dwdsHandler = pipeline.addHandler(server.handleRequest);
     final shelf.Cascade cascade = shelf.Cascade().add(dwds.handler).add(dwdsHandler);
     runZonedGuarded(
diff --git a/packages/flutter_tools/lib/src/runner/flutter_command.dart b/packages/flutter_tools/lib/src/runner/flutter_command.dart
index 971affad9e63d..2da27e8b9b6a1 100644
--- a/packages/flutter_tools/lib/src/runner/flutter_command.dart
+++ b/packages/flutter_tools/lib/src/runner/flutter_command.dart
@@ -281,7 +281,6 @@ abstract class FlutterCommand extends Command<void> {
     );
     argParser.addOption(
       'web-hostname',
-      defaultsTo: 'localhost',
       help:
           'The hostname that the web server will use to resolve an IP to serve '
           'from. The unresolved hostname is used to launch Chrome when using '
diff --git a/packages/flutter_tools/pubspec.yaml b/packages/flutter_tools/pubspec.yaml
index 97b371ccfa691..99d98798e4df2 100644
--- a/packages/flutter_tools/pubspec.yaml
+++ b/packages/flutter_tools/pubspec.yaml
@@ -12,12 +12,13 @@ dependencies:
   # https://github.com/flutter/flutter/blob/main/docs/infra/Updating-dependencies-in-Flutter.md
   archive: 3.6.1
   args: 2.7.0
+  build_runner: ^2.5.4
   dds: 5.0.4
   dwds: 24.4.0
   code_builder: 4.10.1
   collection: 1.19.1
   completion: 1.0.1
-  coverage: 1.14.1
+  coverage: 1.15.0
   crypto: 3.0.6
   ffi: 2.1.4
   file: 7.0.1
@@ -45,6 +46,8 @@ dependencies:
   stream_channel: 2.1.4
   shelf_web_socket: 2.0.1
   shelf_static: 1.1.3
+  shelf_router: ^1.1.4
+  shelf_test_handler: ^2.0.2
   pub_semver: 2.2.0
   pool: 1.5.1
   path: 1.9.1
@@ -113,6 +116,7 @@ dependencies:
   web: 1.1.1
   web_socket: 1.0.1
   yaml_edit: 2.2.2
+  mockito: ^5.4.6
 
 dev_dependencies:
   file_testing: 3.0.2
@@ -126,4 +130,5 @@ dev_dependencies:
 dartdoc:
   # Exclude this package from the hosted API docs.
   nodoc: true
-# PUBSPEC CHECKSUM: kr614i
+
+# PUBSPEC CHECKSUM: p2iphr
diff --git a/packages/flutter_tools/test/commands.shard/hermetic/drive_test.dart b/packages/flutter_tools/test/commands.shard/hermetic/drive_test.dart
index 48235e6d2255f..26da2cc6294c5 100644
--- a/packages/flutter_tools/test/commands.shard/hermetic/drive_test.dart
+++ b/packages/flutter_tools/test/commands.shard/hermetic/drive_test.dart
@@ -584,7 +584,7 @@ void main() {
         throwsToolExit(),
       );
 
-      final DebuggingOptions options = await command.createDebuggingOptions(false);
+      final DebuggingOptions options = await command.createDebuggingOptions();
 
       expect(options.startPaused, true);
       expect(options.disableServiceAuthCodes, true);
@@ -634,7 +634,7 @@ void main() {
         throwsToolExit(),
       );
 
-      final DebuggingOptions options = await command.createDebuggingOptions(false);
+      final DebuggingOptions options = await command.createDebuggingOptions();
       expect(options.disablePortPublication, false);
     },
     overrides: <Type, Generator>{
@@ -670,7 +670,7 @@ void main() {
         ..connectionInterface = DeviceConnectionInterface.attached;
       fakeDeviceManager.attachedDevices = <Device>[usbDevice];
 
-      final DebuggingOptions options = await command.createDebuggingOptions(false);
+      final DebuggingOptions options = await command.createDebuggingOptions();
       expect(options.disablePortPublication, true);
     },
     overrides: <Type, Generator>{
@@ -706,7 +706,7 @@ void main() {
         throwsToolExit(),
       );
 
-      final DebuggingOptions options = await command.createDebuggingOptions(false);
+      final DebuggingOptions options = await command.createDebuggingOptions();
       expect(options.disablePortPublication, true);
     },
     overrides: <Type, Generator>{
diff --git a/packages/flutter_tools/test/commands.shard/hermetic/run_test.dart b/packages/flutter_tools/test/commands.shard/hermetic/run_test.dart
index 62e47264ddd4c..bbd9a30162c28 100644
--- a/packages/flutter_tools/test/commands.shard/hermetic/run_test.dart
+++ b/packages/flutter_tools/test/commands.shard/hermetic/run_test.dart
@@ -15,18 +15,21 @@ import 'package:flutter_tools/src/base/io.dart';
 import 'package:flutter_tools/src/base/logger.dart';
 import 'package:flutter_tools/src/base/platform.dart';
 import 'package:flutter_tools/src/base/terminal.dart';
+import 'package:flutter_tools/src/base/time.dart';
 import 'package:flutter_tools/src/build_info.dart';
 import 'package:flutter_tools/src/cache.dart';
 import 'package:flutter_tools/src/commands/daemon.dart';
 import 'package:flutter_tools/src/commands/run.dart';
 import 'package:flutter_tools/src/devfs.dart';
 import 'package:flutter_tools/src/device.dart';
+import 'package:flutter_tools/src/features.dart';
 import 'package:flutter_tools/src/globals.dart' as globals;
 import 'package:flutter_tools/src/ios/devices.dart';
 import 'package:flutter_tools/src/project.dart';
 import 'package:flutter_tools/src/resident_runner.dart';
 import 'package:flutter_tools/src/runner/flutter_command.dart';
 import 'package:flutter_tools/src/web/compile.dart';
+import 'package:flutter_tools/src/web/web_runner.dart';
 import 'package:test/fake.dart';
 import 'package:unified_analytics/unified_analytics.dart' as analytics;
 import 'package:vm_service/vm_service.dart';
@@ -396,7 +399,7 @@ void main() {
             isNull,
           );
 
-          final DebuggingOptions options = await command.createDebuggingOptions(false);
+          final DebuggingOptions options = await command.createDebuggingOptions();
           expect(options.uninstallFirst, isTrue);
         },
         overrides: <Type, Generator>{
@@ -931,7 +934,11 @@ void main() {
     });
 
     group('--web-header', () {
+      late FakeWebRunnerFactory fakeWebRunnerFactory;
+
       setUp(() {
+        fakeWebRunnerFactory = FakeWebRunnerFactory();
+
         fileSystem.file('lib/main.dart').createSync(recursive: true);
         fileSystem.file('pubspec.yaml').createSync();
         fileSystem.file('.dart_tool/package_config.json')
@@ -942,7 +949,11 @@ void main() {
   "configVersion": 2
 }
 ''');
-        final device = FakeDevice(isLocalEmulator: true, platformType: PlatformType.android);
+        final device = FakeDevice(
+          isLocalEmulator: true,
+          platformType: PlatformType.web,
+          targetPlatform: TargetPlatform.web_javascript,
+        );
         testDeviceManager.devices = <Device>[device];
       });
 
@@ -957,14 +968,19 @@ void main() {
             throwsToolExit(),
           );
 
-          final DebuggingOptions options = await command.createDebuggingOptions(true);
-          expect(options.webHeaders, <String, String>{'foo': 'bar'});
+          expect(fakeWebRunnerFactory.lastOptions, isNotNull);
+          expect(fakeWebRunnerFactory.lastOptions!.devConfig, isNotNull);
+          expect(fakeWebRunnerFactory.lastOptions!.devConfig!.headers, <String, String>{
+            'foo': 'bar',
+          });
         },
         overrides: <Type, Generator>{
           FileSystem: () => fileSystem,
           ProcessManager: () => FakeProcessManager.any(),
           Logger: () => logger,
           DeviceManager: () => testDeviceManager,
+          FeatureFlags: () => FakeFeatureFlags(),
+          WebRunnerFactory: () => fakeWebRunnerFactory,
         },
       );
 
@@ -975,17 +991,17 @@ void main() {
           await expectLater(
             () => createTestCommandRunner(
               command,
-            ).run(<String>['run', '--no-pub', '--no-hot', '--web-header', 'foo']),
+            ).run(<String>['run', '--no-pub', '--no-hot', '--no-resident', '--web-header', 'foo']),
             throwsToolExit(message: 'Invalid web headers: foo'),
           );
-
-          await expectLater(() => command.createDebuggingOptions(true), throwsToolExit());
         },
         overrides: <Type, Generator>{
           FileSystem: () => fileSystem,
           ProcessManager: () => FakeProcessManager.any(),
           Logger: () => logger,
           DeviceManager: () => testDeviceManager,
+          FeatureFlags: () => FakeFeatureFlags(),
+          WebRunnerFactory: () => fakeWebRunnerFactory,
         },
       );
 
@@ -1002,14 +1018,10 @@ void main() {
               'run',
               '--no-pub',
               '--no-hot',
+              '--no-resident',
               '--web-header',
               'hurray/headers=flutter',
             ]),
-            throwsToolExit(),
-          );
-
-          await expectLater(
-            () => command.createDebuggingOptions(true),
             throwsToolExit(message: 'Invalid web headers: hurray/headers=flutter'),
           );
         },
@@ -1018,15 +1030,20 @@ void main() {
           ProcessManager: () => FakeProcessManager.any(),
           Logger: () => logger,
           DeviceManager: () => testDeviceManager,
+          FeatureFlags: () => FakeFeatureFlags(),
+          WebRunnerFactory: () => fakeWebRunnerFactory,
         },
       );
 
       testUsingContext(
         'throws a ToolExit when using --wasm on a non-web platform',
         () async {
+          testDeviceManager.devices = <Device>[FakeDevice(platformType: PlatformType.android)];
           final command = RunCommand();
           await expectLater(
-            () => createTestCommandRunner(command).run(<String>['run', '--no-pub', '--wasm']),
+            () => createTestCommandRunner(
+              command,
+            ).run(<String>['run', '--no-pub', '--no-resident', '--wasm']),
             throwsToolExit(message: '--wasm is only supported on the web platform'),
           );
         },
@@ -1035,6 +1052,8 @@ void main() {
           ProcessManager: () => FakeProcessManager.any(),
           Logger: () => logger,
           DeviceManager: () => testDeviceManager,
+          FeatureFlags: () => FakeFeatureFlags(),
+          WebRunnerFactory: () => fakeWebRunnerFactory,
         },
       );
 
@@ -1043,9 +1062,12 @@ void main() {
         () async {
           final command = RunCommand();
           await expectLater(
-            () => createTestCommandRunner(
-              command,
-            ).run(<String>['run', '--no-pub', ...WebRendererMode.skwasm.toCliDartDefines]),
+            () => createTestCommandRunner(command).run(<String>[
+              'run',
+              '--no-pub',
+              '--no-resident',
+              ...WebRendererMode.skwasm.toCliDartDefines,
+            ]),
             throwsToolExit(message: 'Skwasm renderer requires --wasm'),
           );
         },
@@ -1054,6 +1076,8 @@ void main() {
           ProcessManager: () => FakeProcessManager.any(),
           Logger: () => logger,
           DeviceManager: () => testDeviceManager,
+          FeatureFlags: () => FakeFeatureFlags(),
+          WebRunnerFactory: () => fakeWebRunnerFactory,
         },
       );
 
@@ -1072,17 +1096,24 @@ void main() {
             throwsToolExit(),
           );
 
-          final DebuggingOptions options = await command.createDebuggingOptions(true);
-          expect(options.webHeaders, <String, String>{'hurray': 'flutter,flutter=hurray'});
+          expect(fakeWebRunnerFactory.lastOptions, isNotNull);
+          expect(fakeWebRunnerFactory.lastOptions!.devConfig, isNotNull);
+          expect(fakeWebRunnerFactory.lastOptions!.devConfig!.headers, <String, String>{
+            'hurray': 'flutter,flutter=hurray',
+          });
         },
         overrides: <Type, Generator>{
           FileSystem: () => fileSystem,
           ProcessManager: () => FakeProcessManager.any(),
           Logger: () => logger,
           DeviceManager: () => testDeviceManager,
+          FeatureFlags: () => FakeFeatureFlags(),
+          WebRunnerFactory: () => fakeWebRunnerFactory,
         },
       );
     });
+
+    // ... (rest of the file)
   });
 
   group('terminal', () {
@@ -1241,7 +1272,7 @@ void main() {
         throwsToolExit(),
       );
 
-      final DebuggingOptions options = await command.createDebuggingOptions(true);
+      final DebuggingOptions options = await command.createDebuggingOptions();
 
       expect(options.webUseSseForDebugBackend, false);
       expect(options.webUseSseForDebugProxy, false);
@@ -1283,7 +1314,7 @@ void main() {
         throwsToolExit(),
       );
 
-      final DebuggingOptions options = await command.createDebuggingOptions(false);
+      final DebuggingOptions options = await command.createDebuggingOptions();
 
       expect(options.startPaused, true);
       expect(options.disableServiceAuthCodes, true);
@@ -1319,7 +1350,7 @@ void main() {
         throwsToolExit(),
       );
 
-      final DebuggingOptions options = await command.createDebuggingOptions(false);
+      final DebuggingOptions options = await command.createDebuggingOptions();
 
       expect(options.usingCISystem, true);
     },
@@ -1340,7 +1371,7 @@ void main() {
         throwsToolExit(),
       );
 
-      final DebuggingOptions options = await command.createDebuggingOptions(false);
+      final DebuggingOptions options = await command.createDebuggingOptions();
 
       expect(options.webUseWasm, true);
       expect(options.webRenderer, WebRendererMode.skwasm);
@@ -1369,7 +1400,7 @@ void main() {
         ),
       );
 
-      final DebuggingOptions options = await command.createDebuggingOptions(true);
+      final DebuggingOptions options = await command.createDebuggingOptions();
       expect(options.webLaunchUrl, 'http://flutter.dev');
 
       final pattern = RegExp(r'^((http)?:\/\/)[^\s]+');
@@ -1482,6 +1513,7 @@ class FakeDevice extends Fake implements Device {
   @override
   String get displayName => name;
 
+  // THIS IS A KEY FIX
   @override
   Future<TargetPlatform> get targetPlatform async => _targetPlatform;
 
@@ -1693,3 +1725,38 @@ class FakeAnsiTerminal extends Fake implements AnsiTerminal {
   @override
   bool get singleCharMode => setSingleCharModeHistory.last;
 }
+
+/// A Fake that implements FeatureFlags and enables web.
+class FakeFeatureFlags extends Fake implements FeatureFlags {
+  @override
+  bool get isWebEnabled => true;
+
+  @override
+  bool isEnabled(Feature feature) => feature.master.enabledByDefault;
+}
+
+/// A Fake WebRunnerFactory that CAPTURES the debugging options passed to it.
+class FakeWebRunnerFactory extends Fake implements WebRunnerFactory {
+  DebuggingOptions? lastOptions;
+
+  @override
+  ResidentRunner createWebRunner(
+    FlutterDevice device, {
+    String? target,
+    required bool stayResident,
+    required DebuggingOptions debuggingOptions,
+    required analytics.Analytics analytics,
+    required FileSystem fileSystem,
+    required FlutterProject flutterProject,
+    required Logger logger,
+    required OutputPreferences outputPreferences,
+    required Platform platform,
+    required SystemClock systemClock,
+    required Terminal terminal,
+    bool machine = false,
+    Future<String> Function(String)? urlTunneller,
+  }) {
+    lastOptions = debuggingOptions;
+    return FakeResidentRunner();
+  }
+}
diff --git a/packages/flutter_tools/test/general.shard/drive/web_driver_service_test.dart b/packages/flutter_tools/test/general.shard/drive/web_driver_service_test.dart
index 9c5b83b8f3146..1f04254e40ce7 100644
--- a/packages/flutter_tools/test/general.shard/drive/web_driver_service_test.dart
+++ b/packages/flutter_tools/test/general.shard/drive/web_driver_service_test.dart
@@ -14,6 +14,7 @@ import 'package:flutter_tools/src/base/time.dart';
 import 'package:flutter_tools/src/build_info.dart';
 import 'package:flutter_tools/src/device.dart';
 import 'package:flutter_tools/src/drive/web_driver_service.dart';
+import 'package:flutter_tools/src/isolated/devfs_config.dart';
 import 'package:flutter_tools/src/project.dart';
 import 'package:flutter_tools/src/reporting/reporting.dart';
 import 'package:flutter_tools/src/resident_runner.dart';
@@ -277,13 +278,14 @@ void main() {
       final WebDriverService service = setUpDriverService();
       final device = FakeDevice();
       final webHeaders = <String, String>{'test-header': 'test-value'};
+      final devConfig = DevConfig(headers: webHeaders);
       await service.start(
         BuildInfo.profile,
         device,
-        DebuggingOptions.enabled(BuildInfo.profile, webHeaders: webHeaders, ipv6: true),
+        DebuggingOptions.enabled(BuildInfo.profile, devConfig: devConfig, ipv6: true),
       );
       await service.stop();
-      expect(FakeResidentRunner.instance.debuggingOptions.webHeaders, equals(webHeaders));
+      expect(FakeResidentRunner.instance.debuggingOptions.devConfig?.headers, equals(webHeaders));
     },
     overrides: <Type, Generator>{WebRunnerFactory: () => FakeWebRunnerFactory()},
   );
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 10771e2d9ffdc..730c0557ce4b2 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
@@ -24,6 +24,7 @@ import 'package:flutter_tools/src/dart/pub.dart';
 import 'package:flutter_tools/src/devfs.dart';
 import 'package:flutter_tools/src/device.dart';
 import 'package:flutter_tools/src/globals.dart' as globals;
+import 'package:flutter_tools/src/isolated/devfs_config.dart';
 import 'package:flutter_tools/src/isolated/devfs_web.dart';
 import 'package:flutter_tools/src/isolated/resident_web_runner.dart';
 import 'package:flutter_tools/src/project.dart';
@@ -1867,8 +1868,10 @@ flutter:
     'throws when port is an integer outside the valid TCP range',
     () async {
       final logger = BufferLogger.test();
+      const devConfig = DevConfig(port: 65536);
+      const devConfig2 = DevConfig(port: -1);
 
-      var debuggingOptions = DebuggingOptions.enabled(BuildInfo.debug, port: '65536');
+      var debuggingOptions = DebuggingOptions.enabled(BuildInfo.debug, devConfig: devConfig);
       ResidentRunner residentWebRunner = setUpResidentRunner(
         flutterDevice,
         logger: logger,
@@ -1876,7 +1879,7 @@ flutter:
       );
       await expectToolExitLater(residentWebRunner.run(), matches('Invalid port: 65536.*'));
 
-      debuggingOptions = DebuggingOptions.enabled(BuildInfo.debug, port: '-1');
+      debuggingOptions = DebuggingOptions.enabled(BuildInfo.debug, devConfig: devConfig2);
       residentWebRunner = setUpResidentRunner(
         flutterDevice,
         logger: logger,
diff --git a/packages/flutter_tools/test/general.shard/web/devfs_web_ddc_modules_test.dart b/packages/flutter_tools/test/general.shard/web/devfs_web_ddc_modules_test.dart
index f126800ab13cb..750e5d934d568 100644
--- a/packages/flutter_tools/test/general.shard/web/devfs_web_ddc_modules_test.dart
+++ b/packages/flutter_tools/test/general.shard/web/devfs_web_ddc_modules_test.dart
@@ -17,6 +17,7 @@ import 'package:flutter_tools/src/compile.dart';
 import 'package:flutter_tools/src/convert.dart';
 import 'package:flutter_tools/src/devfs.dart';
 import 'package:flutter_tools/src/globals.dart' as globals;
+import 'package:flutter_tools/src/isolated/devfs_config.dart';
 import 'package:flutter_tools/src/isolated/devfs_web.dart';
 import 'package:flutter_tools/src/isolated/release_asset_server.dart';
 import 'package:flutter_tools/src/isolated/web_asset_server.dart';
@@ -783,11 +784,8 @@ void main() {
       final ResidentCompiler residentCompiler = FakeResidentCompiler()
         ..output = const CompilerOutput('a', 0, <Uri>[]);
 
+      const devConfig = DevConfig();
       final webDevFS = WebDevFS(
-        hostname: 'localhost',
-        port: 0,
-        tlsCertPath: null,
-        tlsCertKeyPath: null,
         packagesFilePath: '.dart_tool/package_config.json',
         urlTunneller: null,
         useSseForDebugProxy: true,
@@ -805,7 +803,6 @@ void main() {
         entrypoint: Uri.base,
         testMode: true,
         expressionCompiler: null,
-        extraHeaders: const <String, String>{},
         chromiumLauncher: null,
         ddcModuleSystem: usesDdcModuleSystem,
         canaryFeatures: canaryFeatures,
@@ -813,6 +810,7 @@ void main() {
         isWasm: false,
         useLocalCanvasKit: false,
         rootDirectory: globals.fs.currentDirectory,
+        devConfig: devConfig,
         fileSystem: globals.fs,
         logger: globals.logger,
         platform: globals.platform,
@@ -892,12 +890,8 @@ void main() {
         outputFile.parent.childFile('a.map').writeAsStringSync('{}');
         outputFile.parent.childFile('a.metadata').writeAsStringSync('{}');
 
+        const devConfig = DevConfig();
         final webDevFS = WebDevFS(
-          // if this is any other value, we will do a real ip lookup
-          hostname: 'any',
-          port: 0,
-          tlsCertPath: null,
-          tlsCertKeyPath: null,
           packagesFilePath: '.dart_tool/package_config.json',
           urlTunneller: null,
           useSseForDebugProxy: true,
@@ -915,7 +909,6 @@ void main() {
           entrypoint: Uri.base,
           testMode: true,
           expressionCompiler: null,
-          extraHeaders: const <String, String>{},
           chromiumLauncher: null,
           ddcModuleSystem: usesDdcModuleSystem,
           canaryFeatures: canaryFeatures,
@@ -923,6 +916,7 @@ void main() {
           isWasm: false,
           useLocalCanvasKit: false,
           rootDirectory: globals.fs.currentDirectory,
+          devConfig: devConfig,
           fileSystem: globals.fs,
           logger: globals.logger,
           platform: globals.platform,
@@ -974,11 +968,8 @@ void main() {
     outputFile.parent.childFile('a.json').writeAsStringSync('{}');
     outputFile.parent.childFile('a.map').writeAsStringSync('{}');
 
+    const devConfig = DevConfig();
     final webDevFS = WebDevFS(
-      hostname: 'any',
-      port: 0,
-      tlsCertPath: null,
-      tlsCertKeyPath: null,
       packagesFilePath: '.dart_tool/package_config.json',
       urlTunneller: null,
       useSseForDebugProxy: true,
@@ -990,7 +981,6 @@ void main() {
       entrypoint: Uri.base,
       testMode: true,
       expressionCompiler: null,
-      extraHeaders: const <String, String>{},
       chromiumLauncher: null,
       nativeNullAssertions: true,
       ddcModuleSystem: usesDdcModuleSystem,
@@ -999,6 +989,7 @@ void main() {
       isWasm: false,
       useLocalCanvasKit: false,
       rootDirectory: globals.fs.currentDirectory,
+      devConfig: devConfig,
       fileSystem: globals.fs,
       logger: globals.logger,
       platform: globals.platform,
@@ -1019,11 +1010,8 @@ void main() {
     outputFile.parent.childFile('a.json').writeAsStringSync('{}');
     outputFile.parent.childFile('a.map').writeAsStringSync('{}');
 
+    const devConfig = DevConfig();
     final webDevFS = WebDevFS(
-      hostname: 'localhost',
-      port: 0,
-      tlsCertPath: null,
-      tlsCertKeyPath: null,
       packagesFilePath: '.dart_tool/package_config.json',
       urlTunneller: null,
       useSseForDebugProxy: true,
@@ -1042,7 +1030,6 @@ void main() {
       entrypoint: Uri.base,
       testMode: true,
       expressionCompiler: null,
-      extraHeaders: const <String, String>{},
       chromiumLauncher: null,
       ddcModuleSystem: usesDdcModuleSystem,
       canaryFeatures: canaryFeatures,
@@ -1050,6 +1037,7 @@ void main() {
       isWasm: false,
       useLocalCanvasKit: false,
       rootDirectory: globals.fs.currentDirectory,
+      devConfig: devConfig,
       fileSystem: globals.fs,
       logger: globals.logger,
       platform: globals.platform,
@@ -1077,11 +1065,8 @@ void main() {
     final String dummyCertPath = globals.fs.path.join(dataPath, 'tls_cert', 'dummy-cert.pem');
     final String dummyCertKeyPath = globals.fs.path.join(dataPath, 'tls_cert', 'dummy-key.pem');
 
+    final devConfig = DevConfig(https: HttpsConfig(certPath: dummyCertPath, certKeyPath: dummyCertKeyPath));
     final webDevFS = WebDevFS(
-      hostname: 'localhost',
-      port: 0,
-      tlsCertPath: dummyCertPath,
-      tlsCertKeyPath: dummyCertKeyPath,
       packagesFilePath: '.dart_tool/package_config.json',
       urlTunneller: null,
       useSseForDebugProxy: true,
@@ -1094,7 +1079,6 @@ void main() {
       entrypoint: Uri.base,
       testMode: true,
       expressionCompiler: null,
-      extraHeaders: const <String, String>{},
       chromiumLauncher: null,
       ddcModuleSystem: usesDdcModuleSystem,
       canaryFeatures: canaryFeatures,
@@ -1102,6 +1086,7 @@ void main() {
       isWasm: false,
       useLocalCanvasKit: false,
       rootDirectory: globals.fs.currentDirectory,
+      devConfig: devConfig,
       fileSystem: globals.fs,
       logger: globals.logger,
       platform: globals.platform,
@@ -1120,11 +1105,8 @@ void main() {
   test(
     'allows frame embedding',
     () => testbed.run(() async {
+      const devConfig = DevConfig();
       final WebAssetServer webAssetServer = await WebAssetServer.start(
-        null,
-        'localhost',
-        0,
-        null,
         null,
         null,
         true,
@@ -1140,11 +1122,11 @@ void main() {
         false,
         Uri.base,
         null,
-        const <String, String>{},
         webRenderer: WebRendererMode.canvaskit,
         isWasm: false,
         useLocalCanvasKit: false,
         testMode: true,
+        devConfig: devConfig,
         fileSystem: globals.fs,
         logger: globals.logger,
         platform: globals.platform,
@@ -1160,11 +1142,8 @@ void main() {
     () => testbed.run(() async {
       const extraHeaderKey = 'hurray';
       const extraHeaderValue = 'flutter';
+      const devConfig = DevConfig(headers: <String,String>{extraHeaderKey: extraHeaderValue});
       final WebAssetServer webAssetServer = await WebAssetServer.start(
-        null,
-        'localhost',
-        0,
-        null,
         null,
         null,
         true,
@@ -1180,11 +1159,11 @@ void main() {
         false,
         Uri.base,
         null,
-        const <String, String>{extraHeaderKey: extraHeaderValue},
         webRenderer: WebRendererMode.canvaskit,
         isWasm: false,
         useLocalCanvasKit: false,
         testMode: true,
+        devConfig: devConfig,
         fileSystem: globals.fs,
         logger: globals.logger,
         platform: globals.platform,
@@ -1250,11 +1229,8 @@ void main() {
       outputFile.parent.childFile('a.map').writeAsStringSync('{}');
       outputFile.parent.childFile('a.metadata').writeAsStringSync('{}');
 
+      const devConfig = DevConfig();
       final webDevFS = WebDevFS(
-        hostname: 'localhost',
-        port: 0,
-        tlsCertPath: null,
-        tlsCertKeyPath: null,
         packagesFilePath: '.dart_tool/package_config.json',
         urlTunneller: null,
         useSseForDebugProxy: true,
@@ -1267,7 +1243,6 @@ void main() {
         entrypoint: Uri.base,
         testMode: true,
         expressionCompiler: null,
-        extraHeaders: const <String, String>{},
         chromiumLauncher: null,
         ddcModuleSystem: usesDdcModuleSystem,
         canaryFeatures: canaryFeatures,
@@ -1275,6 +1250,7 @@ void main() {
         isWasm: false,
         useLocalCanvasKit: false,
         rootDirectory: globals.fs.currentDirectory,
+        devConfig: devConfig,
         fileSystem: globals.fs,
         logger: globals.logger,
         platform: globals.platform,
diff --git a/packages/flutter_tools/test/general.shard/web/devfs_web_test.dart b/packages/flutter_tools/test/general.shard/web/devfs_web_test.dart
index 4293af6213334..e0b9d9091eb4a 100644
--- a/packages/flutter_tools/test/general.shard/web/devfs_web_test.dart
+++ b/packages/flutter_tools/test/general.shard/web/devfs_web_test.dart
@@ -17,6 +17,7 @@ import 'package:flutter_tools/src/compile.dart';
 import 'package:flutter_tools/src/convert.dart';
 import 'package:flutter_tools/src/devfs.dart';
 import 'package:flutter_tools/src/globals.dart' as globals;
+import 'package:flutter_tools/src/isolated/devfs_config.dart';
 import 'package:flutter_tools/src/isolated/devfs_web.dart';
 import 'package:flutter_tools/src/isolated/release_asset_server.dart';
 import 'package:flutter_tools/src/isolated/web_asset_server.dart';
@@ -908,11 +909,8 @@ void main() {
       final ResidentCompiler residentCompiler = FakeResidentCompiler()
         ..output = const CompilerOutput('a', 0, <Uri>[]);
 
+      const devConfig = DevConfig();
       final webDevFS = WebDevFS(
-        hostname: 'localhost',
-        port: 0,
-        tlsCertPath: null,
-        tlsCertKeyPath: null,
         packagesFilePath: '.dart_tool/package_config.json',
         urlTunneller: null,
         useSseForDebugProxy: true,
@@ -930,7 +928,6 @@ void main() {
         entrypoint: Uri.base,
         testMode: true,
         expressionCompiler: null,
-        extraHeaders: const <String, String>{},
         chromiumLauncher: null,
         ddcModuleSystem: usesDdcModuleSystem,
         canaryFeatures: canaryFeatures,
@@ -938,6 +935,7 @@ void main() {
         isWasm: false,
         useLocalCanvasKit: false,
         rootDirectory: globals.fs.currentDirectory,
+        devConfig: devConfig,
         fileSystem: globals.fs,
         logger: globals.logger,
         platform: globals.platform,
@@ -1018,11 +1016,8 @@ void main() {
       final ResidentCompiler residentCompiler = FakeResidentCompiler()
         ..output = const CompilerOutput('a', 0, <Uri>[]);
 
+      const devConfig = DevConfig();
       final webDevFS = WebDevFS(
-        hostname: 'localhost',
-        port: 0,
-        tlsCertPath: null,
-        tlsCertKeyPath: null,
         packagesFilePath: '.dart_tool/package_config.json',
         urlTunneller: null,
         useSseForDebugProxy: true,
@@ -1040,7 +1035,6 @@ void main() {
         entrypoint: Uri.base,
         testMode: true,
         expressionCompiler: null,
-        extraHeaders: const <String, String>{},
         chromiumLauncher: null,
         ddcModuleSystem: usesDdcModuleSystem,
         canaryFeatures: canaryFeatures,
@@ -1048,6 +1042,7 @@ void main() {
         isWasm: false,
         useLocalCanvasKit: false,
         rootDirectory: globals.fs.currentDirectory,
+        devConfig: devConfig,
         fileSystem: globals.fs,
         logger: globals.logger,
         platform: globals.platform,
@@ -1132,13 +1127,9 @@ void main() {
         outputFile.parent.childFile('a.json').writeAsStringSync('{}');
         outputFile.parent.childFile('a.map').writeAsStringSync('{}');
         outputFile.parent.childFile('a.metadata').writeAsStringSync('{}');
-
+        const devConfig = DevConfig();
         final webDevFS = WebDevFS(
           // if this is any other value, we will do a real ip lookup
-          hostname: 'any',
-          port: 0,
-          tlsCertPath: null,
-          tlsCertKeyPath: null,
           packagesFilePath: '.dart_tool/package_config.json',
           urlTunneller: null,
           useSseForDebugProxy: true,
@@ -1156,7 +1147,6 @@ void main() {
           entrypoint: Uri.base,
           testMode: true,
           expressionCompiler: null,
-          extraHeaders: const <String, String>{},
           chromiumLauncher: null,
           ddcModuleSystem: usesDdcModuleSystem,
           canaryFeatures: canaryFeatures,
@@ -1164,6 +1154,7 @@ void main() {
           isWasm: false,
           useLocalCanvasKit: false,
           rootDirectory: globals.fs.currentDirectory,
+          devConfig: devConfig,
           fileSystem: globals.fs,
           logger: globals.logger,
           platform: globals.platform,
@@ -1217,12 +1208,8 @@ void main() {
       outputFile.parent.childFile('a.sources').writeAsStringSync('');
       outputFile.parent.childFile('a.json').writeAsStringSync('{}');
       outputFile.parent.childFile('a.map').writeAsStringSync('{}');
-
+      const devConfig = DevConfig();
       final webDevFS = WebDevFS(
-        hostname: 'any',
-        port: 0,
-        tlsCertPath: null,
-        tlsCertKeyPath: null,
         packagesFilePath: '.dart_tool/package_config.json',
         urlTunneller: null,
         useSseForDebugProxy: true,
@@ -1234,7 +1221,6 @@ void main() {
         entrypoint: Uri.base,
         testMode: true,
         expressionCompiler: null,
-        extraHeaders: const <String, String>{},
         chromiumLauncher: null,
         nativeNullAssertions: true,
         ddcModuleSystem: usesDdcModuleSystem,
@@ -1243,15 +1229,14 @@ void main() {
         isWasm: false,
         useLocalCanvasKit: false,
         rootDirectory: globals.fs.currentDirectory,
+        devConfig: devConfig,
         fileSystem: globals.fs,
         logger: globals.logger,
         platform: globals.platform,
       );
       webDevFS.requireJS.createSync(recursive: true);
-      webDevFS.stackTraceMapper.createSync(recursive: true);
 
       final Uri uri = await webDevFS.create();
-
       expect(uri.host, 'localhost');
       await webDevFS.destroy();
     }),
@@ -1265,12 +1250,8 @@ void main() {
       outputFile.parent.childFile('a.sources').writeAsStringSync('');
       outputFile.parent.childFile('a.json').writeAsStringSync('{}');
       outputFile.parent.childFile('a.map').writeAsStringSync('{}');
-
+      const devConfig = DevConfig();
       final webDevFS = WebDevFS(
-        hostname: 'localhost',
-        port: 0,
-        tlsCertPath: null,
-        tlsCertKeyPath: null,
         packagesFilePath: '.dart_tool/package_config.json',
         urlTunneller: null,
         useSseForDebugProxy: true,
@@ -1289,7 +1270,6 @@ void main() {
         entrypoint: Uri.base,
         testMode: true,
         expressionCompiler: null,
-        extraHeaders: const <String, String>{},
         chromiumLauncher: null,
         ddcModuleSystem: usesDdcModuleSystem,
         canaryFeatures: canaryFeatures,
@@ -1297,6 +1277,7 @@ void main() {
         isWasm: false,
         useLocalCanvasKit: false,
         rootDirectory: globals.fs.currentDirectory,
+        devConfig: devConfig,
         fileSystem: globals.fs,
         logger: globals.logger,
         platform: globals.platform,
@@ -1326,12 +1307,10 @@ void main() {
 
       final String dummyCertPath = globals.fs.path.join(dataPath, 'tls_cert', 'dummy-cert.pem');
       final String dummyCertKeyPath = globals.fs.path.join(dataPath, 'tls_cert', 'dummy-key.pem');
-
+      final devConfig = DevConfig(
+        https: HttpsConfig(certPath: dummyCertPath, certKeyPath: dummyCertKeyPath),
+      );
       final webDevFS = WebDevFS(
-        hostname: 'localhost',
-        port: 0,
-        tlsCertPath: dummyCertPath,
-        tlsCertKeyPath: dummyCertKeyPath,
         packagesFilePath: '.dart_tool/package_config.json',
         urlTunneller: null,
         useSseForDebugProxy: true,
@@ -1344,7 +1323,6 @@ void main() {
         entrypoint: Uri.base,
         testMode: true,
         expressionCompiler: null,
-        extraHeaders: const <String, String>{},
         chromiumLauncher: null,
         ddcModuleSystem: usesDdcModuleSystem,
         canaryFeatures: canaryFeatures,
@@ -1352,13 +1330,13 @@ void main() {
         isWasm: false,
         useLocalCanvasKit: false,
         rootDirectory: globals.fs.currentDirectory,
+        devConfig: devConfig,
         fileSystem: globals.fs,
         logger: globals.logger,
         platform: globals.platform,
       );
       webDevFS.requireJS.createSync(recursive: true);
       webDevFS.stackTraceMapper.createSync(recursive: true);
-
       final Uri uri = await webDevFS.create();
 
       // Ensure the connection established is secure
@@ -1371,11 +1349,10 @@ void main() {
   test(
     'allows frame embedding',
     () => testbed.run(() async {
+      // Wrap the original async block in testbed.run()
+      const devConfig = DevConfig();
+
       final WebAssetServer webAssetServer = await WebAssetServer.start(
-        null,
-        'localhost',
-        0,
-        null,
         null,
         null,
         true,
@@ -1391,11 +1368,11 @@ void main() {
         false,
         Uri.base,
         null,
-        const <String, String>{},
         webRenderer: WebRendererMode.canvaskit,
         isWasm: false,
         useLocalCanvasKit: false,
         testMode: true,
+        devConfig: devConfig,
         fileSystem: globals.fs,
         logger: globals.logger,
         platform: globals.platform,
@@ -1405,17 +1382,14 @@ void main() {
       await webAssetServer.dispose();
     }, overrides: <Type, Generator>{Artifacts: () => Artifacts.test()}),
   );
-
   test(
     'passes on extra headers',
     () => testbed.run(() async {
       const extraHeaderKey = 'hurray';
       const extraHeaderValue = 'flutter';
+      const devConfig = DevConfig(headers: <String, String>{extraHeaderKey: extraHeaderValue});
+
       final WebAssetServer webAssetServer = await WebAssetServer.start(
-        null,
-        'localhost',
-        0,
-        null,
         null,
         null,
         true,
@@ -1431,11 +1405,11 @@ void main() {
         false,
         Uri.base,
         null,
-        const <String, String>{extraHeaderKey: extraHeaderValue},
         webRenderer: WebRendererMode.canvaskit,
         isWasm: false,
         useLocalCanvasKit: false,
         testMode: true,
+        devConfig: devConfig,
         fileSystem: globals.fs,
         logger: globals.logger,
         platform: globals.platform,
@@ -1446,7 +1420,6 @@ void main() {
       await webAssetServer.dispose();
     }, overrides: <Type, Generator>{Artifacts: () => Artifacts.test()}),
   );
-
   test(
     'WebAssetServer responds to POST requests with 404 not found',
     () => testbed.run(() async {
@@ -1509,12 +1482,8 @@ void main() {
       outputFile.parent.childFile('a.json').writeAsStringSync('{}');
       outputFile.parent.childFile('a.map').writeAsStringSync('{}');
       outputFile.parent.childFile('a.metadata').writeAsStringSync('{}');
-
+      const devConfig = DevConfig();
       final webDevFS = WebDevFS(
-        hostname: 'localhost',
-        port: 0,
-        tlsCertPath: null,
-        tlsCertKeyPath: null,
         packagesFilePath: '.dart_tool/package_config.json',
         urlTunneller: null,
         useSseForDebugProxy: true,
@@ -1527,7 +1496,6 @@ void main() {
         entrypoint: Uri.base,
         testMode: true,
         expressionCompiler: null,
-        extraHeaders: const <String, String>{},
         chromiumLauncher: null,
         ddcModuleSystem: usesDdcModuleSystem,
         canaryFeatures: canaryFeatures,
@@ -1535,6 +1503,7 @@ void main() {
         isWasm: false,
         useLocalCanvasKit: false,
         rootDirectory: globals.fs.currentDirectory,
+        devConfig: devConfig,
         fileSystem: globals.fs,
         logger: globals.logger,
         platform: globals.platform,
diff --git a/packages/flutter_tools/test/general.shard/web/proxy_test.dart b/packages/flutter_tools/test/general.shard/web/proxy_test.dart
new file mode 100644
index 0000000000000..38fe552332fb7
--- /dev/null
+++ b/packages/flutter_tools/test/general.shard/web/proxy_test.dart
@@ -0,0 +1,448 @@
+// 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 'package:flutter_tools/src/globals.dart' as globals;
+import 'package:flutter_tools/src/isolated/devfs_proxy.dart';
+import 'package:shelf/shelf.dart';
+import 'package:test/test.dart';
+import 'package:yaml/yaml.dart';
+
+import '../../src/testbed.dart';
+
+void main() {
+  late TestBed testbed;
+  setUp(() {
+    testbed = TestBed();
+  });
+
+  group('ProxyRule.fromYaml', () {
+    test(
+      'should create SourceProxyRule with source and no replacement',
+      () => testbed.run(() {
+        final yaml =
+            loadYaml('''
+          target: http://localhost:8080
+          source: /api
+        ''')
+                as YamlMap;
+        final ProxyRule? rule = ProxyRule.fromYaml(yaml);
+
+        expect(rule, isA<SourceProxyRule>());
+        expect((rule! as SourceProxyRule).source, '/api');
+        expect(rule.target, 'http://localhost:8080');
+      }),
+    );
+
+    test(
+      'should create SourceProxyRule with source and replacement',
+      () => testbed.run(() {
+        final yaml =
+            loadYaml('''
+          target: http://localhost:8080
+          source: /api
+          replace: /new_api
+        ''')
+                as YamlMap;
+        final ProxyRule? rule = ProxyRule.fromYaml(yaml);
+
+        expect(rule, isA<SourceProxyRule>());
+        expect((rule! as SourceProxyRule).source, '/api');
+        expect(rule.target, 'http://localhost:8080');
+        expect(rule.replace('/api/users'), '/new_api/users');
+        expect(rule.replace('/api/'), '/new_api/');
+        expect(rule.replace('/other'), '/other');
+      }),
+    );
+
+    test(
+      'should create RegexProxyRule with regex and no replacement',
+      () => testbed.run(() {
+        final yaml =
+            loadYaml(r'''
+          target: http://localhost:8081
+          regex: ^/users/(\d+)
+        ''')
+                as YamlMap;
+        final ProxyRule? rule = ProxyRule.fromYaml(yaml);
+
+        expect(rule, isA<RegexProxyRule>());
+        expect((rule! as RegexProxyRule).pattern.pattern, r'^/users/(\d+)');
+        expect(rule.target, 'http://localhost:8081');
+      }),
+    );
+
+    test(
+      'should create RegexProxyRule with regex and replacement using capturing groups',
+      () => testbed.run(() {
+        final yaml =
+            loadYaml(r'''
+          target: http://localhost:8081/user-service
+          regex: ^/users/(\d+)/profile(.*)
+          replace: /user-info/$1/details$2
+        ''')
+                as YamlMap;
+        final ProxyRule? rule = ProxyRule.fromYaml(yaml);
+        expect(rule, isA<RegexProxyRule>());
+        expect(rule!.replace('/users/456/profile/summary'), '/user-info/456/details/summary');
+        expect(rule.replace('/users/789/profile'), '/user-info/789/details');
+        expect(rule.replace('/other/path'), '/other/path');
+      }),
+    );
+
+    test(
+      'should create RegexProxyRule with regex and empty replacement',
+      () => testbed.run(() {
+        final yaml =
+            loadYaml(r'''
+          target: http://localhost:8081/user-service
+          regex: ^/users/\d+/profile
+          replace: ''
+        ''')
+                as YamlMap;
+        final ProxyRule? rule = ProxyRule.fromYaml(yaml);
+        expect(rule, isA<RegexProxyRule>());
+        expect(rule!.replace('/users/456/profile'), '');
+        expect(rule.replace('/users/789/profile/summary'), '/summary');
+      }),
+    );
+
+    test(
+      'should handle invalid regex key gracefully and fall back to RegexProxyRule using escaped string',
+      () => testbed.run(() {
+        final yaml =
+            loadYaml('''
+          target: http://localhost:8082
+          regex: ^/invalid(
+        ''')
+                as YamlMap;
+        final ProxyRule? rule = ProxyRule.fromYaml(yaml, logger: globals.logger);
+
+        expect(rule, isA<RegexProxyRule>());
+        expect((rule! as RegexProxyRule).pattern.pattern, r'\^/invalid\(');
+        expect(rule.target, 'http://localhost:8082');
+      }),
+    );
+
+    test(
+      'should return null if target is missing',
+      () => testbed.run(() {
+        final yaml =
+            loadYaml('''
+          source: /api
+        ''')
+                as YamlMap;
+        final ProxyRule? rule = ProxyRule.fromYaml(yaml, logger: globals.logger);
+
+        expect(rule, isNull);
+      }),
+    );
+
+    test(
+      'should return null if neither source nor regex is provided',
+      () => testbed.run(() {
+        final yaml =
+            loadYaml('''
+          target: http://localhost:8080
+        ''')
+                as YamlMap;
+        final ProxyRule? rule = ProxyRule.fromYaml(yaml, logger: globals.logger);
+
+        expect(rule, isNull);
+      }),
+    );
+  });
+
+  group('RegexProxyRule', () {
+    final ruleNoReplacement = RegexProxyRule(
+      pattern: RegExp(r'^/users/(\d+)'),
+      target: 'http://example.com',
+    );
+
+    final ruleWithCapturingGroupReplacement = RegexProxyRule(
+      pattern: RegExp(r'^/api/v1/users/(\d+)(.*)'),
+      target: 'http://backend.com',
+      replacement: r'/$1/profile$2',
+    );
+
+    final rulePrefixRemovalReplacement = RegexProxyRule(
+      pattern: RegExp(r'^/old_path'),
+      target: 'http://legacy.com',
+      replacement: '/new_path',
+    );
+    final ruleMiddlePattern = RegexProxyRule(
+      pattern: RegExp(r'/test_static'),
+      target: 'http://static.com',
+      replacement: '/assets',
+    );
+
+    final ruleExactMatch = RegexProxyRule(
+      pattern: RegExp(r'^/exact_match_only$'),
+      target: 'http://exact.com',
+      replacement: '/found',
+    );
+    final ruleZeroGroup = RegexProxyRule(
+      pattern: RegExp(r'^/prefix/(.*)'),
+      target: 'http://test.com',
+      replacement: r'/all$0',
+    );
+
+    test('matches should return true for matching regex', () {
+      expect(ruleNoReplacement.matches('/users/123'), isTrue);
+      expect(
+        ruleWithCapturingGroupReplacement.matches('/api/v1/users/456/profile/details'),
+        isTrue,
+      );
+      expect(rulePrefixRemovalReplacement.matches('/old_path/resource'), isTrue);
+      expect(ruleMiddlePattern.matches('hello/test_static/image.png'), isTrue);
+      expect(ruleExactMatch.matches('/exact_match_only'), isTrue);
+      expect(ruleZeroGroup.matches('/prefix/prefix'), isTrue);
+    });
+
+    test('matches should return false for non-matching regex', () {
+      expect(ruleWithCapturingGroupReplacement.matches('/api/v2/users/123'), isFalse);
+      expect(rulePrefixRemovalReplacement.matches('/hello/old_path/resource'), isFalse);
+      expect(ruleExactMatch.matches('/exact_match_only/suffix'), isFalse);
+    });
+
+    test('replace should return original path if no replacement string', () {
+      expect(ruleNoReplacement.replace('/users/123/data'), '/users/123/data');
+    });
+
+    test('replace should apply replacement with capturing groups correctly', () {
+      expect(
+        ruleWithCapturingGroupReplacement.replace('/api/v1/users/789/profile/summary'),
+        '/789/profile/profile/summary',
+      );
+      expect(ruleWithCapturingGroupReplacement.replace('/api/v1/users/100'), '/100/profile');
+    });
+
+    test('replace should apply prefix removal replacement', () {
+      expect(
+        rulePrefixRemovalReplacement.replace('/old_path/resource/data'),
+        '/new_path/resource/data',
+      );
+      expect(rulePrefixRemovalReplacement.replace('/old_path'), '/new_path');
+    });
+
+    test('replace should match exactly', () {
+      final rule = RegexProxyRule(
+        pattern: RegExp(r'/temp1'),
+        target: 'http://legacy.com',
+        replacement: '/temp2/',
+      );
+      expect(rule.replace('/temp1/careful/double/slashes'), '/temp2//careful/double/slashes');
+      expect(
+        rulePrefixRemovalReplacement.replace('/old_pathname/resource/data'),
+        '/new_pathname/resource/data',
+      );
+    });
+
+    test('replace should replace all occurences', () {
+      expect(ruleMiddlePattern.replace('/test_static/test_static/data'), '/assets/assets/data');
+    });
+
+    test('replace should handle regex with no capturing groups in pattern', () {
+      expect(
+        ruleMiddlePattern.replace('hello/test_static/document.pdf'),
+        'hello/assets/document.pdf',
+      );
+    });
+
+    test(r'replace should handle $0 (entire match)', () {
+      expect(ruleZeroGroup.replace('/prefix/something/else'), '/all/prefix/something/else');
+    });
+
+    test('replace should handle non-matching path gracefully', () {
+      expect(ruleWithCapturingGroupReplacement.replace('/non/matching/path'), '/non/matching/path');
+    });
+
+    test('toString provides useful debug information', () {
+      expect(
+        ruleNoReplacement.toString(),
+        r'{pattern: ^/users/(\d+), target: http://example.com, replacement: null}',
+      );
+      expect(
+        rulePrefixRemovalReplacement.toString(),
+        '{pattern: ^/old_path, target: http://legacy.com, replacement: /new_path}',
+      );
+    });
+  });
+
+  group('SourceProxyRule', () {
+    final ruleNoReplacement = SourceProxyRule(source: '/assets/', target: 'http://cdn.example.com');
+
+    final ruleWithReplacement = SourceProxyRule(
+      source: '/old-assets/',
+      target: 'http://cdn.example.com',
+      replacement: '/new-assets/',
+    );
+
+    final ruleEmptyReplacement = SourceProxyRule(
+      source: '/remove-me/',
+      target: 'http://cdn.example.com',
+      replacement: '',
+    );
+    final ruleSlashReplacement = SourceProxyRule(
+      source: '/remove-me-too',
+      target: 'http://cdn.example.com',
+      replacement: '/',
+    );
+
+    test('matches should return true for matching source', () {
+      expect(ruleNoReplacement.matches('/assets/image.png'), isTrue);
+      expect(ruleWithReplacement.matches('/old-assets/script.js'), isTrue);
+      expect(ruleEmptyReplacement.matches('/remove-me/now'), isTrue);
+      expect(ruleSlashReplacement.matches('/remove-me-too-please'), isTrue);
+      expect(ruleSlashReplacement.matches('/remove-me-too/please'), isTrue);
+    });
+
+    test('matches should return false for non-matching source', () {
+      expect(ruleNoReplacement.matches('/data/assets/image.png'), isFalse);
+      expect(ruleWithReplacement.matches('/old/assets/script.js'), isFalse);
+      expect(ruleWithReplacement.matches('/old-assets-prefix/script.js'), isFalse);
+      expect(ruleSlashReplacement.matches('remove-me-too/please'), isFalse);
+    });
+
+    test('replace should return original path if no replacement string', () {
+      expect(ruleNoReplacement.replace('/assets/document.pdf'), '/assets/document.pdf');
+    });
+
+    test('replace should apply replacement for matching source', () {
+      expect(ruleWithReplacement.replace('/old-assets/style.css'), '/new-assets/style.css');
+      expect(ruleWithReplacement.replace('/old-assets/'), '/new-assets/');
+    });
+
+    test('replace should handle empty replacement string', () {
+      expect(ruleEmptyReplacement.replace('/remove-me/file.txt'), 'file.txt');
+      expect(ruleEmptyReplacement.replace('/remove-me/'), '');
+    });
+
+    test('replace should handle slash replacement string', () {
+      expect(ruleSlashReplacement.replace('/remove-me-too'), '/');
+    });
+
+    test('replace should only replace first occurence', () {
+      expect(
+        ruleWithReplacement.replace('/old-assets/old-assets/style.css'),
+        '/new-assets/old-assets/style.css',
+      );
+      expect(ruleSlashReplacement.replace('/remove-me-too/remove-me-too/'), '//remove-me-too/');
+    });
+
+    test('replace should return original path for non-matching source', () {
+      expect(ruleWithReplacement.replace('/other-path/file.txt'), '/other-path/file.txt');
+    });
+    test('toString provides useful debug information', () {
+      expect(
+        ruleNoReplacement.toString(),
+        '{source: /assets/, target: http://cdn.example.com, replacement: null}',
+      );
+      expect(
+        ruleWithReplacement.toString(),
+        '{source: /old-assets/, target: http://cdn.example.com, replacement: /new-assets/}',
+      );
+    });
+  });
+
+  group('proxyRequest', () {
+    test('should correctly proxy all request elements', () async {
+      final Uri originalUrl = Uri.parse('http://original.example.com/path');
+      final Uri finalTargetUrl = Uri.parse('http://target.example.com/newpath');
+      const originalBody = 'Hello, Shelf Proxy!';
+      final originalHeaders = <String, String>{
+        'Content-Type': 'text/plain',
+        'X-Custom-Header': 'value',
+        'content-length': 'ignored',
+      };
+      final originalContext = <String, Object>{'user': 'testuser', 'auth': true};
+
+      final originalRequest = Request(
+        'POST',
+        originalUrl,
+        headers: originalHeaders,
+        body: originalBody,
+        context: originalContext,
+      );
+      final Request proxiedRequest = proxyRequest(originalRequest, finalTargetUrl);
+
+      final expectedHeadersFiltered = Map<String, String>.fromEntries(
+        originalHeaders.entries.where(
+          (MapEntry<String, String> entry) => entry.key.toLowerCase() != 'content-length',
+        ),
+      );
+
+      for (final MapEntry<String, String> entry in expectedHeadersFiltered.entries) {
+        expect(proxiedRequest.headers, containsPair(entry.key, entry.value));
+      }
+
+      expect(proxiedRequest.method, 'POST');
+      expect(proxiedRequest.url.toString(), 'newpath');
+      expect(proxiedRequest.context, originalContext);
+
+      final String proxiedBody = await proxiedRequest.readAsString();
+      expect(proxiedBody, originalBody);
+    });
+
+    test('should handle an empty request body', () async {
+      final Uri originalUrl = Uri.parse('http://original.example.com/empty');
+      final Uri finalTargetUrl = Uri.parse('http://target.example.com/empty-new');
+
+      final originalRequest = Request('GET', originalUrl);
+
+      final Request proxiedRequest = proxyRequest(originalRequest, finalTargetUrl);
+
+      expect(proxiedRequest.method, 'GET');
+      expect(proxiedRequest.url.toString(), 'empty-new');
+      expect(await proxiedRequest.readAsString(), '');
+    });
+
+    test('should handle different HTTP methods', () async {
+      final Uri originalUrl = Uri.parse('http://original.example.com/data');
+      final Uri finalTargetUrl = Uri.parse('http://target.example.com/api/data');
+      final methods = <String>['PUT', 'DELETE', 'PATCH', 'GET'];
+
+      for (final method in methods) {
+        final originalRequest = Request(
+          method,
+          originalUrl,
+          body: method == 'PUT' || method == 'PATCH' ? '{"key": "value"}' : null,
+        );
+
+        final Request proxiedRequest = proxyRequest(originalRequest, finalTargetUrl);
+        expect(proxiedRequest.method, method, reason: 'Method "$method" should be preserved');
+
+        if (method == 'PUT' || method == 'PATCH') {
+          expect(await proxiedRequest.readAsString(), '{"key": "value"}');
+        } else {
+          expect(await proxiedRequest.readAsString(), '');
+        }
+      }
+    });
+  });
+
+  group('proxyMiddleware', () {
+    test('should call inner handler if no rule matches', () async {
+      final rules = <ProxyRule>[
+        RegexProxyRule(pattern: RegExp(r'^/other_api'), target: 'http://mock-backend.com'),
+      ];
+
+      final Middleware middleware = proxyMiddleware(rules);
+
+      var innerHandlerCalled = false;
+      FutureOr<Response> innerHandler(Request request) {
+        innerHandlerCalled = true;
+        return Response.ok('Inner Handler Response');
+      }
+
+      final request = Request('GET', Uri.parse('http://localhost:8080/non_matching_path'));
+      final Response response = await middleware(innerHandler)(request);
+
+      expect(innerHandlerCalled, isTrue);
+      expect(response.statusCode, 200);
+      expect(await response.readAsString(), 'Inner Handler Response');
+    });
+  });
+}
diff --git a/packages/flutter_tools/test/widget_preview_scaffold.shard/widget_preview_scaffold/pubspec.yaml b/packages/flutter_tools/test/widget_preview_scaffold.shard/widget_preview_scaffold/pubspec.yaml
index af24074046f52..c145867524421 100644
--- a/packages/flutter_tools/test/widget_preview_scaffold.shard/widget_preview_scaffold/pubspec.yaml
+++ b/packages/flutter_tools/test/widget_preview_scaffold.shard/widget_preview_scaffold/pubspec.yaml
@@ -16,7 +16,7 @@ dependencies:
   flutter_lints: 6.0.0
   google_fonts: 6.2.1
   stack_trace: 1.12.1
-  url_launcher: 6.3.1
+  url_launcher: 6.3.2
 
   async: 2.13.0
   boolean_selector: 2.1.2
@@ -62,4 +62,4 @@ dependencies:
 flutter:
   uses-material-design: true
 
-# PUBSPEC CHECKSUM: mlb1k3
+# PUBSPEC CHECKSUM: jug770
diff --git a/pubspec.lock b/pubspec.lock
index 98041bf013cb1..bf3ed0f3bbcc2 100644
--- a/pubspec.lock
+++ b/pubspec.lock
@@ -150,10 +150,10 @@ packages:
     dependency: "direct main"
     description:
       name: coverage
-      sha256: aa07dbe5f2294c827b7edb9a87bba44a9c15a3cc81bc8da2ca19b37322d30080
+      sha256: "5da775aa218eaf2151c721b16c01c7676fbfdd99cebba2bf64e8b807a28ff94d"
       url: "https://pub.dev"
     source: hosted
-    version: "1.14.1"
+    version: "1.15.0"
   crypto:
     dependency: "direct main"
     description:
@@ -510,10 +510,10 @@ packages:
     dependency: "direct main"
     description:
       name: native_toolchain_c
-      sha256: "99a7feeac19069bbaf3cf9a4d54f47fa54f3ea6da681f669a8761c80540a0838"
+      sha256: "74a0c80d877c519bc6bde2c4e27b6b01c1f93c9b480f65ceae8bedd3aba3c086"
       url: "https://pub.dev"
     source: hosted
-    version: "0.16.6"
+    version: "0.16.8"
   nested:
     dependency: "direct main"
     description:
@@ -859,10 +859,10 @@ packages:
     dependency: "direct main"
     description:
       name: url_launcher
-      sha256: "9d06212b1362abc2f0f0d78e6f09f726608c74e3b9462e8368bb03314aa8d603"
+      sha256: f6a7e5c4835bb4e3026a04793a4199ca2d14c739ec378fdfe23fc8075d0439f8
       url: "https://pub.dev"
     source: hosted
-    version: "6.3.1"
+    version: "6.3.2"
   url_launcher_android:
     dependency: "direct main"
     description:
@@ -947,10 +947,10 @@ packages:
     dependency: "direct main"
     description:
       name: video_player_avfoundation
-      sha256: "0d47db6cbf72db61d86369219efd35c7f9d93515e1319da941ece81b1f21c49c"
+      sha256: "9fedd55023249f3a02738c195c906b4e530956191febf0838e37d0dac912f953"
       url: "https://pub.dev"
     source: hosted
-    version: "2.7.2"
+    version: "2.8.0"
   video_player_platform_interface:
     dependency: "direct main"
     description:
@@ -963,10 +963,10 @@ packages:
     dependency: "direct main"
     description:
       name: video_player_web
-      sha256: e8bba2e5d1e159d5048c9a491bb2a7b29c535c612bb7d10c1e21107f5bd365ba
+      sha256: "9f3c00be2ef9b76a95d94ac5119fb843dca6f2c69e6c9968f6f2b6c9e7afbdeb"
       url: "https://pub.dev"
     source: hosted
-    version: "2.3.5"
+    version: "2.4.0"
   vm_service:
     dependency: "direct main"
     description:
diff --git a/pubspec.yaml b/pubspec.yaml
index 55ef516d52b16..4ed6b531b59e5 100644
--- a/pubspec.yaml
+++ b/pubspec.yaml
@@ -94,7 +94,7 @@ dependencies:
   code_assets: 0.19.4
   collection: 1.19.1
   convert: 3.1.2
-  coverage: 1.14.1
+  coverage: 1.15.0
   crypto: 3.0.6
   csslib: 1.0.2
   cupertino_icons: 1.0.8
@@ -134,7 +134,7 @@ dependencies:
   meta: 1.16.0
   metrics_center: 1.0.13
   mime: 2.0.0
-  native_toolchain_c: 0.16.6
+  native_toolchain_c: 0.16.8
   nested: 1.0.0
   node_preamble: 2.0.2
   package_config: 2.2.0
@@ -175,7 +175,7 @@ dependencies:
   test_api: 0.7.6
   test_core: 0.6.11
   typed_data: 1.4.0
-  url_launcher: 6.3.1
+  url_launcher: 6.3.2
   url_launcher_android: 6.3.16
   url_launcher_ios: 6.3.3
   url_launcher_linux: 3.2.1
@@ -186,9 +186,9 @@ dependencies:
   vector_math: 2.2.0
   video_player: 2.10.0
   video_player_android: 2.8.7
-  video_player_avfoundation: 2.7.2
+  video_player_avfoundation: 2.8.0
   video_player_platform_interface: 6.4.0
-  video_player_web: 2.3.5
+  video_player_web: 2.4.0
   vm_service: 15.0.2
   vm_snapshot_analysis: 0.7.6
   watcher: 1.1.2
@@ -213,4 +213,4 @@ dependencies:
   pedantic: 1.11.1
   quiver: 3.2.2
   yaml_edit: 2.2.2
-# PUBSPEC CHECKSUM: j61vfe
+# PUBSPEC CHECKSUM: leubun

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