diff --git a/plugins/woocommerce/.wp-env.json b/plugins/woocommerce/.wp-env.json
index 4c11d22dc4a..facd8d58499 100644
--- a/plugins/woocommerce/.wp-env.json
+++ b/plugins/woocommerce/.wp-env.json
@@ -1,6 +1,8 @@
 {
 	"phpVersion": "7.4",
-	"plugins": [ "." ],
+	"plugins": [
+		"."
+	],
 	"config": {
 		"JETPACK_AUTOLOAD_DEV": true,
 		"WP_DEBUG_LOG": true,
@@ -11,7 +13,8 @@
 		"wp-cli.yml": "./tests/wp-cli.yml",
 		"wp-content/plugins/filter-setter.php": "./tests/e2e-pw/bin/filter-setter.php",
 		"wp-content/plugins/process-waiting-actions.php": "./tests/e2e-pw/bin/process-waiting-actions.php",
-		"wp-content/plugins/test-helper-apis.php": "./tests/e2e-pw/bin/test-helper-apis.php"
+		"wp-content/plugins/test-helper-apis.php": "./tests/e2e-pw/bin/test-helper-apis.php",
+		"test-data/images/": "./tests/e2e-pw/test-data/images/"
 	},
 	"lifecycleScripts": {
 		"afterStart": "./tests/e2e-pw/bin/test-env-setup.sh",
diff --git a/plugins/woocommerce/changelog/e2e-product-images-tests b/plugins/woocommerce/changelog/e2e-product-images-tests
new file mode 100644
index 00000000000..d33df9ca10e
--- /dev/null
+++ b/plugins/woocommerce/changelog/e2e-product-images-tests
@@ -0,0 +1,4 @@
+Significance: patch
+Type: dev
+
+E2E tests: Add checks for product images
diff --git a/plugins/woocommerce/tests/e2e-pw/bin/test-env-setup.sh b/plugins/woocommerce/tests/e2e-pw/bin/test-env-setup.sh
index 864b2dd24f0..a6bca1b4820 100755
--- a/plugins/woocommerce/tests/e2e-pw/bin/test-env-setup.sh
+++ b/plugins/woocommerce/tests/e2e-pw/bin/test-env-setup.sh
@@ -37,3 +37,7 @@ if [ $ENABLE_TRACKING == 1 ]; then
 	echo -e 'Enable tracking\n'
 	wp-env run tests-cli wp option update woocommerce_allow_tracking 'yes'
 fi
+
+echo -e 'Upload test images \n'
+wp-env run tests-cli wp media import './test-data/images/image-01.png' './test-data/images/image-02.png' './test-data/images/image-03.png'
+
diff --git a/plugins/woocommerce/tests/e2e-pw/playwright.config.js b/plugins/woocommerce/tests/e2e-pw/playwright.config.js
index 777d117f759..35b09fc1de5 100644
--- a/plugins/woocommerce/tests/e2e-pw/playwright.config.js
+++ b/plugins/woocommerce/tests/e2e-pw/playwright.config.js
@@ -8,6 +8,7 @@ const {
 	DEFAULT_TIMEOUT_OVERRIDE,
 	E2E_MAX_FAILURES,
 	PLAYWRIGHT_HTML_REPORT,
+	REPEAT_EACH,
 } = process.env;
 
 const config = {
@@ -20,6 +21,7 @@ const config = {
 	globalTeardown: require.resolve( './global-teardown' ),
 	testDir: 'tests',
 	retries: 2,
+	repeatEach: REPEAT_EACH ? Number( REPEAT_EACH ) : 1,
 	workers: CI ? 1 : 4,
 	reporter: [
 		[ 'list' ],
diff --git a/plugins/woocommerce/tests/e2e-pw/test-data/images/image-01.png b/plugins/woocommerce/tests/e2e-pw/test-data/images/image-01.png
new file mode 100644
index 00000000000..739672bdbf0
Binary files /dev/null and b/plugins/woocommerce/tests/e2e-pw/test-data/images/image-01.png differ
diff --git a/plugins/woocommerce/tests/e2e-pw/test-data/images/image-02.png b/plugins/woocommerce/tests/e2e-pw/test-data/images/image-02.png
new file mode 100644
index 00000000000..935a794ae8e
Binary files /dev/null and b/plugins/woocommerce/tests/e2e-pw/test-data/images/image-02.png differ
diff --git a/plugins/woocommerce/tests/e2e-pw/test-data/images/image-03.png b/plugins/woocommerce/tests/e2e-pw/test-data/images/image-03.png
new file mode 100644
index 00000000000..bdb9cb39c84
Binary files /dev/null and b/plugins/woocommerce/tests/e2e-pw/test-data/images/image-03.png differ
diff --git a/plugins/woocommerce/tests/e2e-pw/tests/merchant/product-delete.spec.js b/plugins/woocommerce/tests/e2e-pw/tests/merchant/product-delete.spec.js
index bd237c87446..6dc18334b83 100644
--- a/plugins/woocommerce/tests/e2e-pw/tests/merchant/product-delete.spec.js
+++ b/plugins/woocommerce/tests/e2e-pw/tests/merchant/product-delete.spec.js
@@ -4,7 +4,7 @@ const wcApi = require('@woocommerce/woocommerce-rest-api').default;
 baseTest.describe('Products > Delete Product', () => {
 	baseTest.use({storageState: process.env.ADMINSTATE});
 
-	const apiFixture = baseTest.extend({
+	const test = baseTest.extend({
 		api: async ({baseURL}, use) => {
 			const api = new wcApi({
 				url: baseURL,
@@ -21,9 +21,7 @@ baseTest.describe('Products > Delete Product', () => {
 
 			await use(api);
 		},
-	});
 
-	const test = apiFixture.extend({
 		product: async ({api}, use) => {
 			const product = {
 				id: 0,
diff --git a/plugins/woocommerce/tests/e2e-pw/tests/merchant/product-images.spec.js b/plugins/woocommerce/tests/e2e-pw/tests/merchant/product-images.spec.js
new file mode 100644
index 00000000000..9310f02c565
--- /dev/null
+++ b/plugins/woocommerce/tests/e2e-pw/tests/merchant/product-images.spec.js
@@ -0,0 +1,285 @@
+const { test: baseTest, expect } = require( '@playwright/test' );
+const wcApi = require( '@woocommerce/woocommerce-rest-api' ).default;
+
+async function addImageFromLibrary( page, imageName, actionButtonName ) {
+	await page.getByRole( 'tab', { name: 'Media Library' } ).click();
+	await page.getByRole( 'searchbox', { name: 'Search' } ).fill( imageName );
+	const imageLocator = page.getByLabel( imageName ).nth( 0 );
+	await imageLocator.click();
+	const dataId = await imageLocator.getAttribute( 'data-id' );
+	await expect( imageLocator ).toBeChecked();
+	await page.getByRole( 'button', { name: actionButtonName } ).click();
+	return dataId;
+}
+
+baseTest.describe( 'Products > Product Images', () => {
+	baseTest.use( { storageState: process.env.ADMINSTATE } );
+
+	const test = baseTest.extend( {
+		api: async ( { baseURL }, use ) => {
+			const api = new wcApi( {
+				url: baseURL,
+				consumerKey: process.env.CONSUMER_KEY,
+				consumerSecret: process.env.CONSUMER_SECRET,
+				version: 'wc/v3',
+			} );
+
+			await use( api );
+		},
+		product: async ( { api }, use ) => {
+			let product = {
+				id: 0,
+				name: `Product ${ Date.now() }`,
+				type: 'simple',
+				regular_price: '12.99',
+				sale_price: '11.59',
+			};
+
+			await api.post( 'products', product ).then( ( response ) => {
+				product = response.data;
+			} );
+
+			await use( product );
+
+			// Cleanup
+			await api.delete( `products/${ product.id }`, { force: true } );
+		},
+		productWithImage: async ( { api, product }, use ) => {
+			let productWithImage;
+			await api
+				.put( `products/${ product.id }`, {
+					images: [
+						{
+							src: 'http://demo.woothemes.com/woocommerce/wp-content/uploads/sites/56/2013/06/T_2_front.jpg',
+						},
+					],
+				} )
+				.then( ( response ) => {
+					productWithImage = response.data;
+				} );
+
+			await use( productWithImage );
+		},
+		productWithGallery: async ( { api, product }, use ) => {
+			let productWithGallery;
+			await api
+				.put( `products/${ product.id }`, {
+					images: [
+						{
+							src: 'http://demo.woothemes.com/woocommerce/wp-content/uploads/sites/56/2013/06/T_2_front.jpg',
+						},
+						{
+							src: 'http://demo.woothemes.com/woocommerce/wp-content/uploads/sites/56/2013/06/T_2_back.jpg',
+						},
+						{
+							src: 'http://demo.woothemes.com/woocommerce/wp-content/uploads/sites/56/2013/06/T_3_front.jpg',
+						},
+					],
+				} )
+				.then( ( response ) => {
+					productWithGallery = response.data;
+				} );
+
+			await use( productWithGallery );
+		},
+	} );
+
+	test( 'can set product image', async ( { page, product } ) => {
+		await test.step( 'Navigate to product edit page', async () => {
+			await page.goto(
+				`wp-admin/post.php?post=${ product.id }&action=edit`
+			);
+		} );
+
+		await test.step( 'Set product image', async () => {
+			await page
+				.getByRole( 'link', { name: 'Set product image' } )
+				.click();
+			await addImageFromLibrary( page, 'image-01', 'Set product image' );
+
+			// Wait for the product image thumbnail to be updated.
+			// Clicking the "Update" button before this happens will not update the image.
+			// Use src* (contains) instead of src$ (ends with) to match duplicated images, like image-01-1.png
+			await expect(
+				page.locator( '#set-post-thumbnail img[src*="image-01"]' )
+			).toBeVisible();
+
+			await page.getByRole( 'button', { name: 'Update' } ).click();
+		} );
+
+		await test.step( 'Verify product image was set', async () => {
+			// Verify product was updated
+			await expect( page.getByText( 'Product updated.' ) ).toBeVisible();
+
+			// Verify image in store frontend
+			await page.goto( product.permalink );
+			await expect( page.getByTitle( `image-01` ) ).toBeVisible();
+		} );
+	} );
+
+	test( 'can update the product image', async ( {
+		page,
+		productWithImage,
+	} ) => {
+		await test.step( 'Navigate to product edit page', async () => {
+			await page.goto(
+				`wp-admin/post.php?post=${ productWithImage.id }&action=edit`
+			);
+		} );
+
+		await test.step( 'Update product image', async () => {
+			await page.locator( '#set-post-thumbnail' ).click();
+			await addImageFromLibrary( page, 'image-02', 'Set product image' );
+
+			// Wait for the product image thumbnail to be updated.
+			// Clicking the "Update" button before this happens will not update the image.
+			// Use src* (contains) instead of src$ (ends with) to match duplicated images, like image-01-1.png
+			await expect(
+				page.locator( '#set-post-thumbnail img[src*="image-02"]' )
+			).toBeVisible();
+
+			await page.getByRole( 'button', { name: 'Update' } ).click();
+		} );
+
+		await test.step( 'Verify product image was set', async () => {
+			// Verify product was updated
+			await expect( page.getByText( 'Product updated.' ) ).toBeVisible();
+
+			// Verify image in store frontend
+			await page.goto( productWithImage.permalink );
+			await expect( page.getByTitle( `image-02` ) ).toBeVisible();
+		} );
+	} );
+
+	test( 'can delete the product image', async ( {
+		page,
+		productWithImage,
+	} ) => {
+		await test.step( 'Navigate to product edit page', async () => {
+			await page.goto(
+				`wp-admin/post.php?post=${ productWithImage.id }&action=edit`
+			);
+		} );
+
+		await test.step( 'Remove product image', async () => {
+			await page
+				.getByRole( 'link', { name: 'Remove product image' } )
+				.click();
+			await expect(
+				page.getByRole( 'link', { name: 'Set product image' } )
+			).toBeVisible();
+
+			await page.getByRole( 'button', { name: 'Update' } ).click();
+		} );
+
+		await test.step( 'Verify product image was removed', async () => {
+			// Verify product was updated
+			await expect( page.getByText( 'Product updated.' ) ).toBeVisible();
+
+			// Verify image in store frontend
+			await page.goto( productWithImage.permalink );
+			await expect(
+				page.getByAltText( 'Awaiting product image' )
+			).toBeVisible();
+		} );
+	} );
+
+	test( 'can create a product gallery', async ( {
+		page,
+		productWithImage,
+	} ) => {
+		const images = [ 'image-02', 'image-03' ];
+
+		await test.step( 'Navigate to product edit page', async () => {
+			await page.goto(
+				`wp-admin/post.php?post=${ productWithImage.id }&action=edit`
+			);
+		} );
+
+		await test.step( 'Add product gallery images', async () => {
+			const imageSelector = '#product_images_container img';
+			let initialImagesCount = await page
+				.locator( imageSelector )
+				.count();
+
+			for ( const image of images ) {
+				await page
+					.getByRole( 'link', { name: 'Add product gallery images' } )
+					.click();
+				const dataId = await addImageFromLibrary(
+					page,
+					image,
+					'Add to gallery'
+				);
+
+				await expect(
+					page.locator( `li[data-attachment_id="${ dataId }"]` ),
+					'thumbnail should be visible'
+				).toBeVisible();
+				const currentImagesCount = await page
+					.locator( imageSelector )
+					.count();
+				await expect(
+					currentImagesCount,
+					'number of images should increase'
+				).toEqual( initialImagesCount + 1 );
+				initialImagesCount = currentImagesCount;
+			}
+
+			await page.getByRole( 'button', { name: 'Update' } ).click();
+		} );
+
+		await test.step( 'Verify product gallery', async () => {
+			// Verify gallery in store frontend
+			await page.goto( productWithImage.permalink );
+			await expect(
+				page
+					.locator( `#product-${ productWithImage.id } ol img` )
+					.nth( images.length ),
+				'all gallery images should be visible'
+			).toBeVisible(); // +1 for the featured image
+		} );
+	} );
+
+	test( 'can update a product gallery', async ( {
+		page,
+		productWithGallery,
+	} ) => {
+		let imagesCount;
+
+		await test.step( 'Navigate to product edit page', async () => {
+			await page.goto(
+				`wp-admin/post.php?post=${ productWithGallery.id }&action=edit`
+			);
+		} );
+
+		await test.step( 'Remove images from product gallery', async () => {
+			const imageSelector = '#product_images_container img';
+			imagesCount = await page.locator( imageSelector ).count();
+
+			await page.locator( imageSelector ).first().hover();
+			await page.getByRole( 'link', { name: ' Delete' } ).click();
+
+			await expect(
+				await page.locator( imageSelector ).count(),
+				'number of images should decrease'
+			).toEqual( imagesCount - 1 );
+
+			await page.getByRole( 'button', { name: 'Update' } ).click();
+		} );
+
+		await test.step( 'Verify product gallery', async () => {
+			// Verify gallery in store frontend
+			await page.goto( productWithGallery.permalink );
+			const selector = `#product-${ productWithGallery.id } ol img`;
+			await expect(
+				page.locator( selector ).nth( imagesCount - 1 ),
+				'gallery images should be visible'
+			).toBeVisible();
+			await expect(
+				page.locator( selector ).nth( imagesCount ),
+				'one gallery image should not be visible'
+			).toBeHidden();
+		} );
+	} );
+} );