diff --git a/eslint.config.js b/eslint.config.js
index ec5efb7c5fc..a50a725a60f 100644
--- a/eslint.config.js
+++ b/eslint.config.js
@@ -1973,6 +1973,38 @@ export default tseslint.config(
 						'vs/sessions/sessions.common.main.js'
 					]
 				},
+				{
+					'target': 'src/vs/sessions/sessions.web.main.internal.ts',
+					'layer': 'browser',
+					'restrictions': [
+						'vs/base/~',
+						'vs/base/parts/*/~',
+						'vs/platform/*/~',
+						'vs/sessions/~',
+						'vs/sessions/contrib/*/~',
+						'vs/workbench/~',
+						'vs/workbench/browser/**',
+						'vs/workbench/services/*/~',
+						'vs/workbench/contrib/*/~',
+						'vs/sessions/sessions.web.main.js'
+					]
+				},
+				{
+					'target': 'src/vs/sessions/sessions.web.test.internal.ts',
+					'layer': 'browser',
+					'restrictions': [
+						'vs/base/~',
+						'vs/base/parts/*/~',
+						'vs/platform/*/~',
+						'vs/sessions/~',
+						'vs/sessions/contrib/*/~',
+						'vs/workbench/~',
+						'vs/workbench/browser/**',
+						'vs/workbench/services/*/~',
+						'vs/workbench/contrib/*/~',
+						'vs/sessions/sessions.web.main.js'
+					]
+				},
 				{
 					'target': 'src/vs/sessions/~',
 					'restrictions': [
diff --git a/scripts/code-sessions-web.js b/scripts/code-sessions-web.js
index 8cd5ea8283a..ba847b3d066 100644
--- a/scripts/code-sessions-web.js
+++ b/scripts/code-sessions-web.js
@@ -137,7 +137,7 @@ ${importMapJson}
 </head>
 <body aria-label="">
 	<script type="module">
-		import { create, URI } from '${fileRoot}/vs/sessions/sessions.web.main.internal.js';
+		import { create, URI } from '${fileRoot}/vs/sessions/${useMock ? 'sessions.web.test.internal' : 'sessions.web.main.internal'}.js';
 		create(document.body, {
 			productConfiguration: {
 				nameShort: 'Sessions (Web)',
diff --git a/src/vs/sessions/browser/web.test.factory.ts b/src/vs/sessions/browser/web.test.factory.ts
new file mode 100644
index 00000000000..1889be32753
--- /dev/null
+++ b/src/vs/sessions/browser/web.test.factory.ts
@@ -0,0 +1,34 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { IWorkbench, IWorkbenchConstructionOptions } from '../../workbench/browser/web.api.js';
+import { TestSessionsBrowserMain } from './web.test.js';
+import { IDisposable, toDisposable } from '../../base/common/lifecycle.js';
+import { mark } from '../../base/common/performance.js';
+import { DeferredPromise } from '../../base/common/async.js';
+
+const workbenchPromise = new DeferredPromise<IWorkbench>();
+
+/**
+ * Creates the Sessions workbench with mock services for E2E testing.
+ */
+export function create(domElement: HTMLElement, options: IWorkbenchConstructionOptions): IDisposable {
+
+	mark('code/didLoadWorkbenchMain');
+
+	let instantiatedWorkbench: IWorkbench | undefined = undefined;
+	new TestSessionsBrowserMain(domElement, options).open().then(workbench => {
+		instantiatedWorkbench = workbench;
+		workbenchPromise.complete(workbench);
+	});
+
+	return toDisposable(() => {
+		if (instantiatedWorkbench) {
+			instantiatedWorkbench.shutdown();
+		} else {
+			workbenchPromise.p.then(w => w.shutdown());
+		}
+	});
+}
diff --git a/src/vs/sessions/browser/web.test.ts b/src/vs/sessions/browser/web.test.ts
new file mode 100644
index 00000000000..3037ef8e57d
--- /dev/null
+++ b/src/vs/sessions/browser/web.test.ts
@@ -0,0 +1,66 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { ServiceCollection } from '../../platform/instantiation/common/serviceCollection.js';
+import { ILogService } from '../../platform/log/common/log.js';
+import { IBrowserMainWorkbench } from '../../workbench/browser/web.main.js';
+import { Workbench as SessionsWorkbench } from './workbench.js';
+import { SessionsBrowserMain } from './web.main.js';
+import { Emitter, Event } from '../../base/common/event.js';
+import { CancellationToken } from '../../base/common/cancellation.js';
+import { IObservable, observableValue } from '../../base/common/observable.js';
+import { ChatEntitlement, IChatEntitlementService, IChatSentiment } from '../../workbench/services/chat/common/chatEntitlementService.js';
+
+/**
+ * Mock implementation of IChatEntitlementService that makes the Sessions
+ * window think the user is signed in with a Free Copilot plan.
+ */
+class MockChatEntitlementService implements IChatEntitlementService {
+
+	declare readonly _serviceBrand: undefined;
+
+	readonly onDidChangeEntitlement = Event.None;
+	readonly onDidChangeQuotaExceeded = Event.None;
+	readonly onDidChangeQuotaRemaining = Event.None;
+	readonly onDidChangeSentiment = Event.None;
+	readonly onDidChangeAnonymous = Event.None;
+
+	readonly entitlement = ChatEntitlement.Free;
+	readonly entitlementObs: IObservable<ChatEntitlement> = observableValue('entitlement', ChatEntitlement.Free);
+
+	readonly previewFeaturesDisabled = false;
+	readonly organisations: string[] | undefined = undefined;
+	readonly isInternal = false;
+	readonly sku = 'free';
+	readonly copilotTrackingId = 'mock-tracking-id';
+
+	readonly quotas = {};
+
+	readonly sentiment: IChatSentiment = { installed: true, registered: true };
+	readonly sentimentObs: IObservable<IChatSentiment> = observableValue('sentiment', { installed: true, registered: true });
+
+	readonly anonymous = false;
+	readonly anonymousObs: IObservable<boolean> = observableValue('anonymous', false);
+
+	markAnonymousRateLimited(): void { }
+	async update(_token: CancellationToken): Promise<void> { }
+}
+
+/**
+ * Test variant of SessionsBrowserMain that injects mock services
+ * for E2E testing (auth, entitlements).
+ */
+export class TestSessionsBrowserMain extends SessionsBrowserMain {
+
+	protected override createWorkbench(domElement: HTMLElement, serviceCollection: ServiceCollection, logService: ILogService): IBrowserMainWorkbench {
+		console.log('[Sessions Web Test] Injecting mock services');
+
+		// Override entitlement service so Sessions thinks user is signed in
+		serviceCollection.set(IChatEntitlementService, new MockChatEntitlementService());
+
+		console.log('[Sessions Web Test] Creating Sessions workbench with mocks');
+		return new SessionsWorkbench(domElement, undefined, serviceCollection, logService);
+	}
+}
diff --git a/src/vs/sessions/sessions.web.test.internal.ts b/src/vs/sessions/sessions.web.test.internal.ts
new file mode 100644
index 00000000000..b08a01443f4
--- /dev/null
+++ b/src/vs/sessions/sessions.web.test.internal.ts
@@ -0,0 +1,23 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+// Test entry point for the Sessions workbench with mock services.
+// Mirrors sessions.web.main.internal.ts but uses TestSessionsBrowserMain.
+
+import './sessions.web.main.js';
+import { create } from './browser/web.test.factory.js';
+import { URI } from '../base/common/uri.js';
+import { Event, Emitter } from '../base/common/event.js';
+import { Disposable } from '../base/common/lifecycle.js';
+import { LogLevel } from '../platform/log/common/log.js';
+
+export {
+	create,
+	URI,
+	Event,
+	Emitter,
+	Disposable,
+	LogLevel,
+};
