diff --git a/e2e/helpers/connect.ts b/e2e/helpers/connect.ts
index 6006dc8c67004..e399634db7fc8 100644
--- a/e2e/helpers/connect.ts
+++ b/e2e/helpers/connect.ts
@@ -39,7 +39,7 @@ export async function launchApp(homeDir: string) {
   );
   const executablePath = requireFromApp('electron');
 
-  const app = await electron.launch({
+  const electronApp = await electron.launch({
     executablePath,
     args: [connectAppDir, '--insecure'],
     env: {
@@ -51,12 +51,16 @@ export async function launchApp(homeDir: string) {
   });
 
   try {
-    const page = await app.firstWindow();
+    const page = await electronApp.firstWindow();
     await page.waitForLoadState('domcontentloaded');
 
-    return { app, page, [Symbol.asyncDispose]: async () => app.close() };
+    return {
+      electronApp,
+      page,
+      [Symbol.asyncDispose]: async () => electronApp.close(),
+    };
   } catch (err) {
-    await app.close();
+    await electronApp.close();
     throw err;
   }
 }
@@ -104,7 +108,7 @@ export const test = base.extend<{
       await login(launchedApp.page);
     }
     await use({
-      electronApp: launchedApp.app,
+      electronApp: launchedApp.electronApp,
       page: launchedApp.page,
       appConfigPath,
     });
diff --git a/e2e/scripts/open-connect.ts b/e2e/scripts/open-connect.ts
index ef6a975005755..b13e170c2079d 100644
--- a/e2e/scripts/open-connect.ts
+++ b/e2e/scripts/open-connect.ts
@@ -45,5 +45,5 @@ await login(launched.page);
 info('Teleport Connect opened and authenticated');
 info('close the app window or press Ctrl+C to exit');
 
-await new Promise<void>(resolve => launched.app.once('close', resolve));
+await new Promise<void>(resolve => launched.electronApp.once('close', resolve));
 info('Teleport Connect closed');
diff --git a/e2e/tests/connect/firstLaunch.spec.ts b/e2e/tests/connect/firstLaunch.spec.ts
new file mode 100644
index 0000000000000..c4a4d7e0a4c77
--- /dev/null
+++ b/e2e/tests/connect/firstLaunch.spec.ts
@@ -0,0 +1,55 @@
+/**
+ * Teleport
+ * Copyright (C) 2026 Gravitational, Inc.
+ *
+ * This program is free software: you can redistribute it and/or modify
+ * it under the terms of the GNU Affero General Public License as published by
+ * the Free Software Foundation, either version 3 of the License, or
+ * (at your option) any later version.
+ *
+ * This program is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ * GNU Affero General Public License for more details.
+ *
+ * You should have received a copy of the GNU Affero General Public License
+ * along with this program.  If not, see <http://www.gnu.org/licenses/>.
+ */
+
+import fs from 'node:fs/promises';
+import os from 'node:os';
+import path from 'node:path';
+
+import {
+  expect,
+  initializeDataDir,
+  launchApp,
+  test,
+  withDefaultAppConfig,
+} from '@gravitational/e2e/helpers/connect';
+
+test('first launch shows usage data dialog', async () => {
+  await using temp = await fs.mkdtempDisposable(
+    path.join(os.tmpdir(), 'connect-e2e-first-launch-')
+  );
+  // Set usageReporting.enabled to undefined so it's not stored in the config, which causes the
+  // usage data dialog to appear on launch.
+  await initializeDataDir(
+    temp.path,
+    withDefaultAppConfig({ 'usageReporting.enabled': undefined })
+  );
+
+  await using app = await launchApp(temp.path);
+  const { page } = app;
+
+  const usageDataDialog = page.getByText('Anonymous usage data');
+  await expect(usageDataDialog).toBeVisible();
+  await page.getByRole('button', { name: 'Decline', exact: true }).click();
+
+  // Assert the dialog is dismissed – without this, the "Connect a Cluster" check below would pass
+  // even if clicking Decline failed, since that screen is already rendered under the modal.
+  await expect(usageDataDialog).not.toBeVisible();
+
+  // After dismissing the dialog, the app should show the default "Connect a Cluster" screen.
+  await expect(page.getByText('Connect a Cluster')).toBeVisible();
+});
diff --git a/e2e/tests/connect/stateRestoration.spec.ts b/e2e/tests/connect/stateRestoration.spec.ts
new file mode 100644
index 0000000000000..98aa21169ce98
--- /dev/null
+++ b/e2e/tests/connect/stateRestoration.spec.ts
@@ -0,0 +1,258 @@
+/**
+ * Teleport
+ * Copyright (C) 2026 Gravitational, Inc.
+ *
+ * This program is free software: you can redistribute it and/or modify
+ * it under the terms of the GNU Affero General Public License as published by
+ * the Free Software Foundation, either version 3 of the License, or
+ * (at your option) any later version.
+ *
+ * This program is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ * GNU Affero General Public License for more details.
+ *
+ * You should have received a copy of the GNU Affero General Public License
+ * along with this program.  If not, see <http://www.gnu.org/licenses/>.
+ */
+
+import fs from 'node:fs/promises';
+import os from 'node:os';
+import path from 'node:path';
+
+import {
+  expect,
+  initializeDataDir,
+  launchApp,
+  login,
+  test,
+  withDefaultAppConfig,
+} from '@gravitational/e2e/helpers/connect';
+
+// These tests manage the app lifecycle manually (multiple launches/closes), so they do not use the
+// `app` fixture.
+test.describe('state restoration from disk', () => {
+  let tempPath: string;
+
+  test.beforeEach(async () => {
+    tempPath = await fs.mkdtemp(path.join(os.tmpdir(), 'connect-e2e-state-'));
+    await initializeDataDir(tempPath, withDefaultAppConfig({}));
+  });
+
+  test.afterEach(async () => {
+    await fs.rm(tempPath, { recursive: true, force: true });
+  });
+
+  test('relaunch restores tabs', async () => {
+    // Login and create extra tabs.
+    {
+      await using app = await launchApp(tempPath);
+      const { page } = app;
+      await login(page);
+
+      // Open a terminal tab so there are 2 tabs (cluster + terminal).
+      await page.getByTitle('Additional Actions').click();
+      await page.getByText('Open new terminal').click();
+      await expect(
+        page.getByRole('textbox', { name: 'Terminal input' })
+      ).toBeVisible();
+    }
+
+    // Relaunch – the app should offer to restore the terminal tab.
+    {
+      await using app = await launchApp(tempPath);
+      const { page } = app;
+      await expect(page.getByText('Reopen previous session')).toBeVisible();
+      await page.getByRole('button', { name: 'Reopen' }).click();
+      await expect(page.getByText('Reopen previous session')).not.toBeVisible();
+
+      // Both tabs should be restored.
+      await expect(
+        page.locator('[role="tab"][data-doc-kind="doc.cluster"]')
+      ).toBeVisible();
+      await expect(
+        page.locator('[role="tab"][data-doc-kind="doc.terminal_shell"]')
+      ).toBeVisible();
+    }
+  });
+
+  test('missing app_state.json does not crash the app', async () => {
+    // Login to create state files on disk.
+    {
+      await using app = await launchApp(tempPath);
+      await login(app.page);
+    }
+
+    // Remove app_state.json (keep tsh dir) – the app should not crash.
+    const appStatePath = path.join(tempPath, 'userData', 'app_state.json');
+    await fs.rm(appStatePath);
+
+    {
+      await using app = await launchApp(tempPath);
+
+      // Without app_state.json, the app has no saved rootClusterUri, so no workspace is activated
+      // and the cluster connect panel prompts the user to pick one.
+      await expect(
+        app.page.getByText('Log in to a cluster to use Teleport Connect.')
+      ).toBeVisible();
+    }
+  });
+
+  test('missing tsh home directory does not crash the app', async () => {
+    // Login to create state files on disk.
+    {
+      await using app = await launchApp(tempPath);
+      await login(app.page);
+    }
+
+    // Remove the tsh home directory (keep app_state.json) – the app should not crash.
+    const tshHomePath = path.join(tempPath, 'home', '.tsh');
+    await fs.rm(tshHomePath, { recursive: true });
+
+    {
+      await using app = await launchApp(tempPath);
+      const { page } = app;
+
+      // With no tsh dir, no cluster can be connected.
+      await expect(page.getByText('Connect a Cluster')).toBeVisible();
+      // app_state.json still references the old cluster, so setActiveWorkspace should show an error.
+      await expect(
+        page.getByText('Could not set cluster as active')
+      ).toBeVisible();
+    }
+  });
+
+  test('logout clears previous tabs', async () => {
+    await using app = await launchApp(tempPath);
+    const { page } = app;
+    await login(page);
+
+    // Open a terminal tab.
+    await page.getByTitle('Additional Actions').click();
+    await page.getByText('Open new terminal').click();
+    await expect(
+      page.getByRole('textbox', { name: 'Terminal input' })
+    ).toBeVisible();
+
+    // Logout.
+    await page.getByTitle(/Open Profiles/).click();
+    await page.getByTitle(/Log out/).click();
+    await expect(
+      page.getByText('Are you sure you want to log out?')
+    ).toBeVisible();
+    await page.getByRole('button', { name: 'Log Out', exact: true }).click();
+    await expect(page.getByText('Connect a Cluster')).toBeVisible();
+
+    // Login to the same cluster again.
+    await login(page);
+
+    // No restore dialog should appear – logout clears previous tabs.
+    // Only the default cluster tab should be open.
+    const clusterTab = page.locator(
+      '[role="tab"][data-doc-kind="doc.cluster"]'
+    );
+    await expect(clusterTab).toHaveCount(1);
+    await expect(
+      page.locator('[role="tab"][data-doc-kind="doc.terminal_shell"]')
+    ).toHaveCount(0);
+    await expect(page.getByText('Reopen previous session')).not.toBeVisible();
+  });
+
+  test('identical workspace shape does not trigger restore dialog', async () => {
+    // Login, then replace the default cluster tab with a new one (same shape).
+    {
+      await using app = await launchApp(tempPath);
+      const { page } = app;
+      await login(page);
+
+      const clusterTab = page.locator(
+        '[role="tab"][data-doc-kind="doc.cluster"]'
+      );
+      await expect(clusterTab).toBeVisible();
+
+      // Close the existing cluster tab.
+      await clusterTab.locator('.close').click();
+      // Open a new cluster tab via the "+" button.
+      await page.getByTitle(/New Tab/).click();
+      await expect(clusterTab).toBeVisible();
+    }
+
+    // Relaunch – no restore dialog since the workspace has the same shape.
+    {
+      await using app = await launchApp(tempPath);
+      const { page } = app;
+
+      const clusterTab = page.locator(
+        '[role="tab"][data-doc-kind="doc.cluster"]'
+      );
+      await expect(clusterTab).toHaveCount(1);
+      await expect(page.getByText('Reopen previous session')).not.toBeVisible();
+    }
+  });
+
+  test('window remembers size and position after restart', async () => {
+    // Launch the app and resize the window.
+    let targetBounds: { x: number; y: number; width: number; height: number };
+    {
+      await using app = await launchApp(tempPath);
+      const { page } = app;
+      await expect(page.getByText('Connect a Cluster')).toBeVisible();
+
+      // Pick bounds relative to the primary display's work area so the test works on any screen
+      // size and on multi-monitor setups where the primary display may be offset from (0, 0).
+      // WindowsManager.getWindowState restores saved bounds only when they fit entirely within
+      // a display.
+      const requestedBounds = await app.electronApp.evaluate(({ screen }) => {
+        const wa = screen.getPrimaryDisplay().workArea;
+        return {
+          x: wa.x + Math.floor(wa.width * 0.1),
+          y: wa.y + Math.floor(wa.height * 0.1),
+          width: Math.floor(wa.width * 0.6),
+          height: Math.floor(wa.height * 0.6),
+        };
+      });
+
+      // Capture the initial bounds before resizing so we can verify setBounds() had an effect.
+      const initialBounds = await app.electronApp.evaluate(
+        ({ BrowserWindow }) => {
+          const win = BrowserWindow.getAllWindows()[0];
+          return win.getNormalBounds();
+        }
+      );
+
+      await app.electronApp.evaluate(({ BrowserWindow }, bounds) => {
+        const win = BrowserWindow.getAllWindows()[0];
+        win.setBounds(bounds);
+      }, requestedBounds);
+
+      // Read back the accepted bounds after the window manager has applied them. The WM may adjust
+      // the requested rectangle (e.g. on Wayland or tiling layouts), and the app persists
+      // getNormalBounds(), not the requested values.
+      targetBounds = await app.electronApp.evaluate(({ BrowserWindow }) => {
+        const win = BrowserWindow.getAllWindows()[0];
+        return win.getNormalBounds();
+      });
+
+      // Verify the window actually moved. On environments where setBounds() is a no-op (e.g.
+      // Wayland, tiling WMs), the relaunch assertion would pass trivially without this guard.
+      expect(targetBounds).not.toEqual(initialBounds);
+    }
+
+    // Relaunch – the window should restore to the same size & position.
+    {
+      await using app = await launchApp(tempPath);
+
+      // Wait for the app to fully initialize before reading bounds and closing, otherwise the
+      // app may close before the renderer acks the initial cluster store message, causing a
+      // "Failed to receive message acknowledgement from the renderer" error dialog.
+      await expect(app.page.getByText('Connect a Cluster')).toBeVisible();
+
+      const bounds = await app.electronApp.evaluate(({ BrowserWindow }) => {
+        const win = BrowserWindow.getAllWindows()[0];
+        return win.getNormalBounds();
+      });
+
+      expect(bounds).toEqual(targetBounds);
+    }
+  });
+});
diff --git a/web/packages/teleterm/src/ui/services/workspacesService/workspacesService.test.ts b/web/packages/teleterm/src/ui/services/workspacesService/workspacesService.test.ts
index 3f80718dd3a7f..adde6e1ac4e35 100644
--- a/web/packages/teleterm/src/ui/services/workspacesService/workspacesService.test.ts
+++ b/web/packages/teleterm/src/ui/services/workspacesService/workspacesService.test.ts
@@ -531,6 +531,58 @@ describe('setActiveWorkspace', () => {
 
     expect(workspacesService.getRootClusterUri()).toStrictEqual(clusterBar.uri);
   });
+
+  it('opens the documents-reopen dialog in the same tick as setting rootClusterUri', async () => {
+    const cluster = makeRootCluster();
+    const testWorkspace: PersistedWorkspace = {
+      localClusterUri: cluster.uri,
+      documents: [
+        {
+          kind: 'doc.terminal_shell',
+          uri: '/docs/terminal_shell_uri',
+          title: '/Users/alice/Documents',
+        },
+      ],
+      location: '/docs/terminal_shell_uri',
+    };
+
+    const { workspacesService, modalsService } = getTestSetup({
+      cluster,
+      persistedWorkspaces: { [cluster.uri]: testWorkspace },
+    });
+
+    workspacesService.restorePersistedState();
+
+    // Queue a microtask before starting activation. If an await is ever introduced between setting
+    // rootClusterUri and opening the dialog, this microtask will execute before the dialog opens,
+    // causing the assertion below to fail. This invariant matters because e2e tests rely on React
+    // rendering rootClusterUri and the dialog in the same batch.
+    let microtaskRan = false;
+    queueMicrotask(() => {
+      microtaskRan = true;
+    });
+
+    jest
+      .spyOn(modalsService, 'openRegularDialog')
+      .mockImplementation(dialog => {
+        expect(dialog.kind).toEqual('documents-reopen');
+        expect(microtaskRan).toBe(false);
+        expect(workspacesService.getRootClusterUri()).toBe(cluster.uri);
+        if (dialog.kind === 'documents-reopen') {
+          dialog.onDiscard();
+        }
+
+        return {
+          closeDialog: () => {},
+        };
+      });
+
+    await workspacesService.setActiveWorkspace(cluster.uri);
+    expect(modalsService.openRegularDialog).toHaveBeenCalledWith(
+      expect.objectContaining({ kind: 'documents-reopen' }),
+      expect.any(AbortSignal)
+    );
+  });
 });
 
 function getTestSetup(options: {