diff --git a/e2e/site-navigation.test.ts b/e2e/site-navigation.test.ts
new file mode 100644
index 000000000..1dbeaf233
--- /dev/null
+++ b/e2e/site-navigation.test.ts
@@ -0,0 +1,347 @@
+import { test, expect, Page } from '@playwright/test';
+import fs from 'fs-extra';
+import { E2ESession } from './e2e-helpers';
+import Onboarding from './page-objects/onboarding';
+import SiteContent from './page-objects/site-content';
+import WhatsNewModal from './page-objects/whats-new-modal';
+import { getUrlWithAutoLogin } from './utils';
+
+/**
+ * Closes the WordPress Block Editor welcome guide if it appears.
+ * Attempts to close up to 3 times as the modal can appear multiple times.
+ */
+async function closeWelcomeGuide( page: Page ) {
+	// Try to close the modal up to 3 times
+	for ( let i = 0; i < 2; i++ ) {
+		try {
+			// Wait for the modal frame to appear
+			const modalFrame = page.locator( '.components-modal__frame' );
+			await modalFrame.waitFor( { state: 'visible', timeout: 2000 } );
+
+			// Find and click the close button using specific selector
+			const closeButton = page.locator( '.components-modal__header > button[aria-label="Close"]' );
+			await closeButton.waitFor( { state: 'visible', timeout: 2000 } );
+			await closeButton.click();
+		} catch ( e ) {
+			// Modal not found or already closed, exit the loop
+			break;
+		}
+	}
+}
+
+test.describe( 'Site Navigation', () => {
+	const session = new E2ESession();
+
+	const siteName = 'My WordPress Website'; // Use the default site created during onboarding
+
+	let frontendUrl: string;
+	let wpAdminUrl: string;
+
+	test.beforeAll( async () => {
+		await session.launch();
+
+		// Complete onboarding before tests
+		const onboarding = new Onboarding( session.mainWindow );
+		await expect( onboarding.heading ).toBeVisible();
+		await onboarding.continueButton.click();
+
+		const whatsNewModal = new WhatsNewModal( session.mainWindow );
+		if ( await whatsNewModal.locator.isVisible( { timeout: 5000 } ) ) {
+			await whatsNewModal.closeButton.click();
+		}
+
+		// Wait for default site to be ready and get URLs
+		const siteContent = new SiteContent( session.mainWindow, siteName );
+		await expect( siteContent.siteNameHeading ).toBeVisible( { timeout: 120_000 } );
+
+		// Get site URLs for tests
+		const settingsTab = await siteContent.navigateToTab( 'Settings' );
+		wpAdminUrl = await settingsTab.copyWPAdminUrlToClipboard( session.electronApp );
+		frontendUrl = await settingsTab.copySiteUrlToClipboard( session.electronApp );
+	} );
+
+	test.afterAll( async () => {
+		await session.cleanup();
+	} );
+
+	test( 'opens site at homepage', async ( { page } ) => {
+		// Navigate to the site homepage
+		await page.goto( frontendUrl );
+
+		// Verify the page loaded successfully
+		await expect( page ).toHaveURL( frontendUrl );
+
+		// Check for WordPress indicators (body classes, meta tags, etc.)
+		const bodyClass = await page.locator( 'body' ).getAttribute( 'class' );
+		expect( bodyClass ).toMatch( /wordpress|wp-|home/ );
+
+		// Verify page title exists
+		const title = await page.title();
+		expect( title ).toBeTruthy();
+		expect( title.length ).toBeGreaterThan( 0 );
+	} );
+
+	test( 'opens and automatically logs in to WP Admin', async ( { page } ) => {
+		// Navigate to wp-admin with auto-login
+		await page.goto( getUrlWithAutoLogin( wpAdminUrl ) );
+
+		// Verify we're on the dashboard
+		await expect( page ).toHaveURL( /wp-admin/ );
+
+		// Check for dashboard elements
+		await expect( page.locator( '#wpadminbar' ) ).toBeVisible();
+		await expect( page.locator( '#adminmenuback' ) ).toBeVisible();
+
+		// Verify we're logged in by checking for user menu
+		const userMenu = page.locator( '#wp-admin-bar-my-account' );
+		await expect( userMenu ).toBeVisible();
+	} );
+
+	test( 'creates a post', async ( { page } ) => {
+		// Navigate to new post page
+		const newPostUrl = `${ wpAdminUrl }/post-new.php`;
+		await page.goto( getUrlWithAutoLogin( newPostUrl ) );
+
+		const editorFrame = page.frameLocator( 'iframe[name="editor-canvas"]' );
+
+		// Close welcome guide if it appears (always on main page, not in iframe)
+		await closeWelcomeGuide( page );
+
+		// Wait for title to be available in iframe
+		const titleSelector = 'h1.editor-post-title';
+		await editorFrame.locator( titleSelector ).waitFor( { timeout: 30_000 } );
+		await editorFrame.locator( titleSelector ).fill( 'E2E Test Post' );
+
+		// Click into the content area and type
+		await editorFrame.locator( titleSelector ).press( 'Enter' );
+		const contentBlock = editorFrame.locator( 'p[role="document"]' ).first();
+		await contentBlock.fill( 'This is a test post created by automated E2E tests.' );
+
+		// Publish the post (publish buttons are on main page)
+		const publishButton = page.locator( 'button.editor-post-publish-button__button' ).first();
+		await publishButton.waitFor( { state: 'visible', timeout: 10_000 } );
+		await publishButton.click();
+
+		// Wait for and click the confirm publish button in the panel
+		const confirmPublishButton = page.locator( 'button.editor-post-publish-button__button' ).last();
+		await confirmPublishButton.waitFor( { state: 'visible', timeout: 10_000 } );
+		await confirmPublishButton.click();
+
+		// Wait for success message
+		await expect( page.locator( '.components-snackbar' ) ).toBeVisible( { timeout: 10_000 } );
+
+		// Verify post was created by visiting posts list
+		await page.goto( getUrlWithAutoLogin( `${ wpAdminUrl }/edit.php` ) );
+		await expect( page.locator( 'a.row-title:has-text("E2E Test Post")' ) ).toBeVisible();
+	} );
+
+	test( 'uploads media', async ( { page } ) => {
+		// Navigate to media library
+		const addNewMediaUrl = `${ wpAdminUrl }/media-new.php`;
+		await page.goto( getUrlWithAutoLogin( addNewMediaUrl ) );
+
+		// Create a minimal valid PNG file (1x1 red pixel)
+		const pngBuffer = Buffer.from( [
+			0x89, 0x50, 0x4e, 0x47, 0x0d, 0x0a, 0x1a, 0x0a, 0x00, 0x00, 0x00, 0x0d, 0x49, 0x48, 0x44,
+			0x52, 0x00, 0x00, 0x00, 0x01, 0x00, 0x00, 0x00, 0x01, 0x08, 0x02, 0x00, 0x00, 0x00, 0x90,
+			0x77, 0x53, 0xde, 0x00, 0x00, 0x00, 0x0c, 0x49, 0x44, 0x41, 0x54, 0x08, 0x99, 0x63, 0xf8,
+			0xcf, 0xc0, 0x00, 0x00, 0x03, 0x01, 0x01, 0x00, 0x18, 0xdd, 0x83, 0x75, 0x00, 0x00, 0x00,
+			0x00, 0x49, 0x45, 0x4e, 0x44, 0xae, 0x42, 0x60, 0x82,
+		] );
+
+		const testImagePath = '/tmp/e2e-test-image.png';
+		await fs.writeFile( testImagePath, pngBuffer );
+
+		// Upload the file using the HTML5 plupload file input
+		// The actual file input is hidden, so we need to set files directly on it
+		const fileInputPromise = page.waitForEvent( 'filechooser' );
+		await page.locator( '#plupload-browse-button' ).click();
+		const fileChooser = await fileInputPromise;
+		await fileChooser.setFiles( testImagePath );
+
+		// Wait for upload to complete
+		await expect( page.locator( '.media-item .filename' ) ).toBeVisible( { timeout: 30_000 } );
+
+		// Clean up test file
+		await fs.unlink( testImagePath );
+
+		// Verify media was uploaded by checking the library
+		await page.goto( getUrlWithAutoLogin( `${ wpAdminUrl }/upload.php` ) );
+		const mediaItems = page.locator( '.attachment' );
+		await expect( mediaItems.first() ).toBeVisible();
+	} );
+
+	test( 'activates themes', async ( { page } ) => {
+		// Navigate to themes page
+		const themesUrl = `${ wpAdminUrl }/themes.php`;
+		await page.goto( getUrlWithAutoLogin( themesUrl ) );
+
+		// Find a non-active theme
+		const inactiveTheme = page.locator( '.theme:not(.active)' ).first();
+		await expect( inactiveTheme ).toBeVisible();
+
+		// Get the theme slug before activating
+		const themeSlug = await inactiveTheme.getAttribute( 'data-slug' );
+		expect( themeSlug ).toBeTruthy();
+
+		// Hover and click activate
+		await inactiveTheme.click();
+		const activateButton = page.locator( '.inactive-theme > .button.activate' ).first();
+		await activateButton.click();
+
+		// Wait for page reload
+		await page.waitForLoadState( 'networkidle' );
+
+		// Verify the theme is now active
+		const activeTheme = page.locator( `.theme.active[data-slug="${ themeSlug }"]` );
+		await expect( activeTheme ).toBeVisible();
+	} );
+
+	test( 'adds new themes', async ( { page } ) => {
+		// Navigate to themes page
+		const themeInstallUrl = `${ wpAdminUrl }/theme-install.php`;
+		await page.goto( getUrlWithAutoLogin( themeInstallUrl ) );
+
+		// Search for a theme
+		const searchInput = page.locator( '#wp-filter-search-input' );
+		await searchInput.fill( 'Twenty Twenty-Two' );
+		await searchInput.press( 'Enter' );
+
+		// Wait for search results
+		await page.waitForLoadState( 'networkidle' );
+
+		// Find Twenty Twenty-Two theme
+		const themeResult = page.locator( '.theme[data-slug="twentytwentytwo"]' ).first();
+
+		// Install the theme
+		await themeResult.click();
+		const themeInstallOverlay = page.locator( '.theme-install-overlay' );
+		await expect( themeInstallOverlay ).toBeVisible( { timeout: 5_000 } );
+		const installButton = themeInstallOverlay.locator( 'a.theme-install' );
+		await installButton.click();
+
+		// Wait for installation to complete
+		await expect( themeInstallOverlay.locator( 'a.activate' ) ).toBeVisible( {
+			timeout: 30_000,
+		} );
+	} );
+
+	test( 'activates plugin', async ( { page } ) => {
+		// Navigate to plugins page
+		const pluginsUrl = `${ wpAdminUrl }/plugins.php`;
+		await page.goto( getUrlWithAutoLogin( pluginsUrl ) );
+
+		// Find an inactive plugin (Hello Dolly is usually installed by default)
+		const inactivePlugin = page.locator( 'tr.inactive[data-slug="hello-dolly"]' ).first();
+		await expect( inactivePlugin ).toBeVisible();
+		const pluginSlug = await inactivePlugin.getAttribute( 'data-slug' );
+
+		// Activate the plugin
+		const activateLink = inactivePlugin.locator( 'span.activate a' );
+		await activateLink.click();
+
+		// Wait for plugin to be activated
+		await page.waitForLoadState( 'networkidle' );
+
+		// Verify plugin is now active
+		const activePlugin = page.locator( `tr.active[data-slug="${ pluginSlug }"]` );
+		await expect( activePlugin ).toBeVisible();
+	} );
+
+	test( 'adds new plugin', async ( { page } ) => {
+		// Navigate to plugins page
+		const pluginInstallUrl = `${ wpAdminUrl }/plugin-install.php`;
+		await page.goto( getUrlWithAutoLogin( pluginInstallUrl ) );
+
+		// Search for a plugin
+		const searchInput = page.locator( '#search-plugins' );
+		await searchInput.fill( 'Contact Form 7' );
+		await searchInput.press( 'Enter' );
+
+		// Wait for search results
+		await page.waitForLoadState( 'networkidle' );
+
+		// Find Contact Form 7 plugin
+		const pluginResult = page.locator( '.plugin-card-contact-form-7' ).first();
+		await expect( pluginResult ).toBeVisible();
+
+		// Install the plugin
+		const installButton = pluginResult.locator( 'a.install-now' );
+		await installButton.click();
+
+		// Wait for installation to complete
+		await page.waitForLoadState( 'networkidle' );
+
+		// Verify plugin was installed
+		await expect( pluginResult.locator( 'a.activate-now' ) ).toBeVisible( {
+			timeout: 30_000,
+		} );
+	} );
+
+	test( '"Post name" permalink structure works', async ( { page } ) => {
+		// Navigate to permalink settings
+		const permalinkUrl = `${ wpAdminUrl }/options-permalink.php`;
+		await page.goto( getUrlWithAutoLogin( permalinkUrl ) );
+
+		// Select "Post name" permalink structure
+		const postNameRadio = page.locator( 'input#permalink-input-post-name' );
+		await postNameRadio.check();
+
+		// Save changes
+		const saveButton = page.locator( '#submit' );
+		await saveButton.click();
+
+		// Wait for success message
+		await expect( page.locator( '#setting-error-settings_updated' ) ).toBeVisible();
+
+		// Verify the setting was saved
+		await expect( postNameRadio ).toBeChecked();
+
+		// Create a test post to verify the permalink structure works
+		const newPostUrl = `${ wpAdminUrl }/post-new.php`;
+		await page.goto( getUrlWithAutoLogin( newPostUrl ) );
+
+		const editorFrame = page.frameLocator( 'iframe[name="editor-canvas"]' );
+
+		// Close welcome guide if it appears (always on main page, not in iframe)
+		await closeWelcomeGuide( page );
+
+		// Wait for title to be available in iframe
+		const titleSelector = 'h1.editor-post-title';
+		await editorFrame.locator( titleSelector ).waitFor( { timeout: 30_000 } );
+		await editorFrame.locator( titleSelector ).fill( 'Permalink Test Post' );
+
+		// Click into the content area and type
+		await editorFrame.locator( titleSelector ).press( 'Enter' );
+		const contentBlock = editorFrame.locator( 'p[role="document"]' ).first();
+		await contentBlock.fill( 'Testing permalink structure.' );
+
+		// Publish the post (publish buttons are on main page)
+		const publishButton = page.locator( 'button.editor-post-publish-button__button' ).first();
+		await publishButton.waitFor( { state: 'visible', timeout: 10_000 } );
+		await publishButton.click();
+
+		// Wait for and click the confirm publish button in the panel
+		const confirmPublishButton = page.locator( 'button.editor-post-publish-button__button' ).last();
+		await confirmPublishButton.waitFor( { state: 'visible', timeout: 10_000 } );
+		await confirmPublishButton.click();
+
+		// Wait for publish
+		await expect( page.locator( '.components-snackbar' ) ).toBeVisible( { timeout: 10_000 } );
+
+		// Get the post URL from the editor
+		const viewPostLink = page.locator( 'a:has-text("View Post")' ).first();
+		const postUrl = await viewPostLink.getAttribute( 'href' );
+
+		// Verify the URL follows the post name structure (contains the post slug)
+		expect( postUrl ).toMatch( /\/permalink-test-post\/?$/ );
+
+		// Visit the post and verify it loads
+		await page.goto( postUrl! );
+		await page.waitForLoadState( 'networkidle' );
+		await expect( page.locator( 'h1' ) ).toHaveText( 'Permalink Test Post' );
+		await expect( page.locator( 'div.entry-content' ) ).toHaveText(
+			'Testing permalink structure.'
+		);
+	} );
+} );