diff --git a/tests/e2e/cloudinary-image-delivery.spec.js b/tests/e2e/cloudinary-image-delivery.spec.js
new file mode 100644
index 000000000..45c89dbc4
--- /dev/null
+++ b/tests/e2e/cloudinary-image-delivery.spec.js
@@ -0,0 +1,202 @@
+/**
+ * External dependencies
+ */
+const fs = require( 'fs' );
+const path = require( 'path' );
+const { test, expect } = require( '@wordpress/e2e-test-utils-playwright' );
+
+/**
+ * Internal dependencies
+ */
+const { ensureCloudinaryConnected } = require( './utils/connection' );
+const { wpCli } = require( './utils/wizard' );
+
+const FIXTURE_PATH = path.join( __dirname, 'fixtures', 'test-image.jpg' );
+
+let cloudName;
+
+/**
+ * Per-test scratch space populated by beforeEach.
+ *
+ * @type {{ postId: number, attachmentId: number, postLink: string }|null}
+ */
+let created = null;
+
+/**
+ * Assert that a given image URL is served by Cloudinary under the
+ * expected cloud name. We intentionally do not assert specific
+ * transformations — those are an implementation detail of the plugin
+ * and may change.
+ *
+ * @param {string} rawUrl        The src or srcset candidate.
+ * @param {string} expectedCloud The cloud name parsed from CLOUDINARY_E2E_URL.
+ */
+function expectCloudinaryUrl( rawUrl, expectedCloud ) {
+	let parsed;
+	try {
+		parsed = new URL( rawUrl );
+	} catch ( e ) {
+		throw new Error( `Image URL is not parseable: ${ rawUrl }` );
+	}
+	expect( parsed.host, `host of ${ rawUrl }` ).toBe( 'res.cloudinary.com' );
+	expect(
+		parsed.pathname.startsWith( `/${ expectedCloud }/` ),
+		`pathname of ${ rawUrl } should start with /${ expectedCloud }/`
+	).toBe( true );
+}
+
+test.describe( 'Cloudinary image delivery', () => {
+	test.beforeAll( () => {
+		( { cloudName } = ensureCloudinaryConnected() );
+	} );
+
+	test.beforeEach( async ( { requestUtils } ) => {
+		// Upload the fixture image via REST.
+		const file = fs.readFileSync( FIXTURE_PATH );
+		const media = await requestUtils.rest( {
+			method: 'POST',
+			path: '/wp/v2/media',
+			headers: {
+				'Content-Type': 'image/jpeg',
+				'Content-Disposition': 'attachment; filename="test-image.jpg"',
+			},
+			data: file,
+		} );
+
+		const attachmentId = media.id;
+		const sourceUrl = media.source_url;
+
+		// Create a published post that uses the attachment as both
+		// featured image and an inline image block.
+		const content =
+			`<!-- wp:image {"id":${ attachmentId }} -->\n` +
+			`<figure class="wp-block-image"><img src="${ sourceUrl }" alt="" class="wp-image-${ attachmentId }"/></figure>\n` +
+			`<!-- /wp:image -->`;
+
+		const post = await requestUtils.rest( {
+			method: 'POST',
+			path: '/wp/v2/posts',
+			data: {
+				status: 'publish',
+				title: `Cloudinary e2e ${ Date.now() }`,
+				content,
+				featured_media: attachmentId,
+			},
+		} );
+
+		created = {
+			postId: post.id,
+			attachmentId,
+			postLink: post.link,
+		};
+
+		// The plugin's URL rewriting depends on the asset being synced
+		// to Cloudinary. With auto_sync enabled (wizard default), the
+		// first front-end render queues the sync but renders local
+		// URLs. Driving `wp cloudinary sync` here makes the test
+		// deterministic without relying on the cron-driven queue.
+		wpCli( [ 'cloudinary', 'sync' ] );
+	} );
+
+	test.afterEach( async () => {
+		if ( ! created ) {
+			return;
+		}
+		const { postId, attachmentId } = created;
+		created = null;
+
+		// Best-effort cleanup via WP-CLI. We do not use the REST API
+		// here because the test wp-env runs without pretty permalinks,
+		// which makes appending `force=true` to a `?rest_route=`-style
+		// URL fragile. WP-CLI is unambiguous and we already use it in
+		// other helpers (see utils/wizard.js).
+		try {
+			wpCli( [ 'post', 'delete', String( postId ), '--force' ] );
+		} catch ( e ) {
+			// eslint-disable-next-line no-console
+			console.warn( 'Post cleanup failed:', e.message );
+		}
+		try {
+			wpCli( [ 'post', 'delete', String( attachmentId ), '--force' ] );
+		} catch ( e ) {
+			// eslint-disable-next-line no-console
+			console.warn( 'Media cleanup failed:', e.message );
+		}
+	} );
+
+	test( 'serves featured image and inline image via Cloudinary', async ( {
+		page,
+	} ) => {
+		expect( created, 'post + attachment should be created' ).not.toBeNull();
+
+		await page.goto( created.postLink );
+
+		// Featured image: themes mark it with .wp-post-image.
+		const featured = page.locator( 'img.wp-post-image' ).first();
+		await expect(
+			featured,
+			'featured image should render on the post page'
+		).toBeVisible();
+
+		// Inline image from the_content. Scope to .wp-block-image so
+		// the featured image (also tagged wp-image-<ID> by some themes)
+		// is not double-counted.
+		const inline = page
+			.locator( `.wp-block-image img.wp-image-${ created.attachmentId }` )
+			.first();
+		await expect(
+			inline,
+			'inline image block should render in post content'
+		).toBeVisible();
+
+		// With the wizard's default settings, the plugin lazy-loads
+		// images: the initial server-rendered markup carries a tiny
+		// SVG placeholder in `src` and the real Cloudinary delivery
+		// is encoded in `data-public-id` + `data-transformations` +
+		// `data-version`. The JS then constructs the Cloudinary URL
+		// and swaps it into `src` once the image scrolls into view.
+		//
+		// We assert two things per image:
+		//   1. `data-public-id` is present — proves the plugin marked
+		//      the element for Cloudinary delivery (this is its own
+		//      explicit signal, independent of lazyload / theme markup).
+		//   2. Any HTTP(S) URL attribute present (`src` after the JS
+		//      swap, `srcset` when emitted by the theme) is served
+		//      from `res.cloudinary.com/<cloud_name>/...`.
+		const httpUrls = [];
+		for ( const loc of [ featured, inline ] ) {
+			await loc.scrollIntoViewIfNeeded();
+
+			const publicId = await loc.getAttribute( 'data-public-id' );
+			expect(
+				publicId,
+				'plugin should mark the image with data-public-id'
+			).toBeTruthy();
+
+			const src = await loc.getAttribute( 'src' );
+			if ( src && /^https?:\/\//.test( src ) ) {
+				httpUrls.push( src );
+			}
+
+			const srcset = await loc.getAttribute( 'srcset' );
+			if ( srcset ) {
+				const firstCandidate = srcset
+					.split( ',' )[ 0 ]
+					.trim()
+					.split( /\s+/ )[ 0 ];
+				if ( firstCandidate && /^https?:\/\//.test( firstCandidate ) ) {
+					httpUrls.push( firstCandidate );
+				}
+			}
+		}
+
+		expect(
+			httpUrls.length,
+			'at least one image should expose a Cloudinary URL via src or srcset'
+		).toBeGreaterThan( 0 );
+
+		for ( const url of httpUrls ) {
+			expectCloudinaryUrl( url, cloudName );
+		}
+	} );
+} );
diff --git a/tests/e2e/fixtures/test-image.jpg b/tests/e2e/fixtures/test-image.jpg
new file mode 100644
index 000000000..5cf40b2f0
Binary files /dev/null and b/tests/e2e/fixtures/test-image.jpg differ
diff --git a/tests/e2e/utils/connection.js b/tests/e2e/utils/connection.js
new file mode 100644
index 000000000..66e27f561
--- /dev/null
+++ b/tests/e2e/utils/connection.js
@@ -0,0 +1,65 @@
+/**
+ * Helpers for putting the Cloudinary plugin into a "connected" state
+ * without driving the wizard UI.
+ *
+ * Setting the connection option directly via WP-CLI is faster and
+ * keeps this spec decoupled from the wizard spec, which exercises
+ * the UI path separately.
+ */
+
+const { wpCli, getCloudinaryUrlFromEnv } = require( './wizard' );
+
+/**
+ * Parse the cloud name out of a `cloudinary://key:secret@cloud_name` URL.
+ *
+ * @param {string} cloudinaryUrl
+ * @return {string} The cloud_name segment.
+ * @throws If the URL does not match the expected shape.
+ */
+function parseCloudName( cloudinaryUrl ) {
+	const match = /^cloudinary:\/\/[^:]+:[^@]+@([A-Za-z0-9_-]+)/.exec(
+		cloudinaryUrl
+	);
+	if ( ! match ) {
+		throw new Error(
+			`Could not parse cloud name from CLOUDINARY_E2E_URL: ${ cloudinaryUrl }`
+		);
+	}
+	return match[ 1 ];
+}
+
+/**
+ * Set the plugin's `cloudinary_connect` option directly so the plugin
+ * is "connected" for the duration of the spec.
+ *
+ * Mirrors what the wizard saves on completion. We deliberately do
+ * NOT pre-populate `cloudinary_connection_signature` or
+ * `cloudinary_status`; the plugin will populate those on first need.
+ *
+ * @return {{ cloudName: string }} The cloud name extracted from the URL.
+ */
+function ensureCloudinaryConnected() {
+	const cloudinaryUrl = getCloudinaryUrlFromEnv();
+	const cloudName = parseCloudName( cloudinaryUrl );
+
+	// Build the JSON payload the plugin expects.
+	const payload = JSON.stringify( { cloudinary_url: cloudinaryUrl } );
+
+	// `wp option update --format=json <name> <value>` requires the
+	// value to be a valid JSON literal. Wrap in single quotes for the
+	// docker-exec'd shell.
+	wpCli( [
+		'option',
+		'update',
+		'cloudinary_connect',
+		`'${ payload }'`,
+		'--format=json',
+	] );
+
+	return { cloudName };
+}
+
+module.exports = {
+	parseCloudName,
+	ensureCloudinaryConnected,
+};