diff --git a/tests/e2e/cloudinary-delete-sync.spec.js b/tests/e2e/cloudinary-delete-sync.spec.js
new file mode 100644
index 000000000..b11dda99b
--- /dev/null
+++ b/tests/e2e/cloudinary-delete-sync.spec.js
@@ -0,0 +1,207 @@
+/**
+ * External dependencies
+ */
+const fs = require( 'fs' );
+const path = require( 'path' );
+const { test, expect } = require( './fixtures' );
+
+/**
+ * Internal dependencies
+ */
+const { ensureCloudinaryConnected } = require( './utils/connection' );
+const { phpJson } = require( './utils/settings' );
+const { wpCli, wpEvalFile } = require( './utils/wizard' );
+
+const FIXTURE_PATH = path.join( __dirname, 'fixtures', 'test-image.jpg' );
+
+/**
+ * Attachment IDs the spec creates. afterAll deletes the ones a test did
+ * not delete.
+ *
+ * @type {number[]}
+ */
+let attachmentIds = [];
+
+/**
+ * Public IDs of the Cloudinary assets the spec creates. afterAll removes
+ * the ones a test did not remove.
+ *
+ * @type {string[]}
+ */
+let publicIds = [];
+
+/**
+ * Upload the fixture image and sync it to Cloudinary.
+ *
+ * Syncs only this attachment through the push sync, which is what the
+ * auto-sync queue runs, so other media in the test site is not touched.
+ *
+ * @param {Object} requestUtils RequestUtils fixture.
+ * @param {string} label        Part of the filename.
+ * @return {Promise<{ attachmentId: number, publicId: string }>} The synced attachment.
+ */
+async function uploadAndSync( requestUtils, label ) {
+	const media = await requestUtils.rest( {
+		method: 'POST',
+		path: '/wp/v2/media',
+		headers: {
+			'Content-Type': 'image/jpeg',
+			'Content-Disposition': `attachment; filename="delete-${ label }-${ Date.now() }.jpg"`,
+		},
+		data: fs.readFileSync( FIXTURE_PATH ),
+	} );
+	attachmentIds.push( media.id );
+
+	const synced = JSON.parse(
+		wpEvalFile( `
+			$id     = ${ Number( media.id ) };
+			$plugin = get_plugin_instance();
+			$plugin->get_component( 'sync' )->managers['push']->process_assets( $id );
+			$media = $plugin->get_component( 'media' );
+			echo wp_json_encode(
+				array(
+					'publicId' => $media->has_public_id( $id ) ? $media->get_public_id( $id ) : '',
+					'synced'   => $plugin->get_component( 'sync' )->is_synced( $id, true ),
+				)
+			);
+		` )
+	);
+	expect( synced.publicId, 'the image should get a public ID' ).toBeTruthy();
+	publicIds.push( synced.publicId );
+	expect( synced.synced, 'the image should be fully synced' ).toBe( true );
+
+	return { attachmentId: media.id, publicId: synced.publicId };
+}
+
+/**
+ * Check through the Admin API if an image asset exists on Cloudinary.
+ *
+ * @param {string} publicId The public ID.
+ * @return {boolean} True when the asset exists.
+ */
+function remoteAssetExists( publicId ) {
+	// Only a 404 means the asset is gone. Any other API error must fail
+	// the test, or a timeout would look like a successful delete.
+	const result = wpEvalFile( `
+		$details = get_plugin_instance()
+			->get_component( 'connect' )
+			->api
+			->get_asset_details( ${ phpJson( publicId ) }, 'image' );
+		if ( ! is_wp_error( $details ) ) {
+			echo 'exists';
+		} elseif ( 404 === (int) $details->get_error_code() ) {
+			echo 'missing';
+		} else {
+			echo 'error ' . $details->get_error_code() . ': ' . $details->get_error_message();
+		}
+	` );
+	if ( 'exists' !== result && 'missing' !== result ) {
+		throw new Error(
+			`Could not check the Cloudinary asset ${ publicId }: ${ result }`
+		);
+	}
+	return 'exists' === result;
+}
+
+/**
+ * Forget an attachment that a test deleted, so afterAll does not delete it
+ * again.
+ *
+ * @param {number} attachmentId The attachment ID.
+ */
+function forgetAttachment( attachmentId ) {
+	attachmentIds = attachmentIds.filter( ( id ) => id !== attachmentId );
+}
+
+// @serial: needs real credentials in `cloudinary_connect` to sync assets,
+// while every analytics spec overwrites that option with fake ones.
+test.describe( 'Cloudinary delete sync', { tag: '@serial' }, () => {
+	test.beforeAll( () => {
+		ensureCloudinaryConnected();
+	} );
+
+	test.afterAll( () => {
+		const ids = attachmentIds;
+		const assets = publicIds;
+		attachmentIds = [];
+		publicIds = [];
+
+		// Remove the assets directly, so a failed test does not leave
+		// them in the Cloudinary account.
+		if ( assets.length ) {
+			try {
+				wpEvalFile( `
+					$api = get_plugin_instance()->get_component( 'connect' )->api;
+					foreach ( ${ phpJson( assets ) } as $public_id ) {
+						$api->destroy( 'image', array( 'public_id' => $public_id ) );
+					}
+				` );
+			} catch ( e ) {
+				console.warn(
+					'Cleanup of the Cloudinary assets failed:',
+					e.message
+				);
+			}
+		}
+
+		for ( const id of ids ) {
+			try {
+				wpCli( [ 'post', 'delete', String( id ), '--force' ] );
+			} catch ( e ) {
+				console.warn( `Cleanup of post ${ id } failed:`, e.message );
+			}
+		}
+	} );
+
+	test( 'deleting an attachment through REST removes its Cloudinary asset', async ( {
+		requestUtils,
+	} ) => {
+		const { attachmentId, publicId } = await uploadAndSync(
+			requestUtils,
+			'rest'
+		);
+		expect(
+			remoteAssetExists( publicId ),
+			'the asset should exist on Cloudinary before the delete'
+		).toBe( true );
+
+		await requestUtils.deleteMedia( attachmentId );
+		forgetAttachment( attachmentId );
+
+		expect(
+			remoteAssetExists( publicId ),
+			'the asset should be removed from Cloudinary'
+		).toBe( false );
+	} );
+
+	test( '"Delete permanently" in the Media Library removes the Cloudinary asset', async ( {
+		admin,
+		page,
+		requestUtils,
+	} ) => {
+		const { attachmentId, publicId } = await uploadAndSync(
+			requestUtils,
+			'library'
+		);
+		expect( remoteAssetExists( publicId ) ).toBe( true );
+
+		await admin.visitAdminPage( 'upload.php', 'mode=list' );
+		const row = page.locator( `#post-${ attachmentId }` );
+		await row.hover();
+
+		page.once( 'dialog', ( dialog ) => dialog.accept() );
+		await Promise.all( [
+			page.waitForURL( /upload\.php.*deleted=1/ ),
+			row.locator( 'a.submitdelete' ).click(),
+		] );
+		forgetAttachment( attachmentId );
+
+		await expect( page.locator( `#post-${ attachmentId }` ) ).toHaveCount(
+			0
+		);
+		expect(
+			remoteAssetExists( publicId ),
+			'the asset should be removed from Cloudinary'
+		).toBe( false );
+	} );
+} );
diff --git a/tests/e2e/utils/settings.js b/tests/e2e/utils/settings.js
index 3c6720d29..328316e38 100644
--- a/tests/e2e/utils/settings.js
+++ b/tests/e2e/utils/settings.js
@@ -62,6 +62,7 @@ function readSettings( slugs ) {
 }
 
 module.exports = {
+	phpJson,
 	readSettings,
 	saveSettings,
 };