diff --git a/packages/calypso-e2e/src/index.ts b/packages/calypso-e2e/src/index.ts
index b3a1517aec140..b3750a222277f 100644
--- a/packages/calypso-e2e/src/index.ts
+++ b/packages/calypso-e2e/src/index.ts
@@ -3,12 +3,10 @@ import * as BrowserManager from './browser-manager';
 import * as DataHelper from './data-helper';
 import * as ElementHelper from './element-helper';
 import * as MediaHelper from './media-helper';
+export type { TestFile } from './media-helper';
 
 export { BrowserHelper, BrowserManager, MediaHelper, DataHelper, ElementHelper };
 
 export * from './lib';
 export * from './hooks';
 export * from './email-client';
-export * from './types';
-
-export type { TestFile } from './media-helper';
diff --git a/packages/calypso-e2e/src/media-helper.ts b/packages/calypso-e2e/src/media-helper.ts
index bcbc712a4ad75..43d6a2d2f0af3 100644
--- a/packages/calypso-e2e/src/media-helper.ts
+++ b/packages/calypso-e2e/src/media-helper.ts
@@ -1,3 +1,4 @@
+import { constants } from 'fs';
 import fs from 'fs/promises';
 import os from 'os';
 import path from 'path';
@@ -56,72 +57,56 @@ export function getVideoDir(): string {
 /**
  * Creates a temporary test file by cloning a source file under a new name.
  *
+ * @param {string} sourcePath Full path on disk of the source file.
  * @param {{[key: string]: string}} param0 Parameter object.
- * @param {string} param0.sourceFileName Basename of the source file to be cloned.
- * @param {string} [param0.testFileName] Basename of the test file to be generated.
+ * @param {string} [param0.postfix] Additional suffix to be used for the file.
  * @returns {Promise<TestFile>} Object implementing the TestFile interface.
+ * @throws {Error} If source file was not found, or source file did not contain an extension.
  */
-export async function createTestFile( {
-	sourceFileName,
-	testFileName,
-}: {
-	sourceFileName: string;
-	testFileName?: string;
-} ): Promise< TestFile > {
-	let filename = getTimestamp();
-	// If the output `testFileName` is defined, use that as part of the final filename.
-	if ( testFileName ) {
-		filename += `-${ testFileName }`;
+export async function createTestFile(
+	sourcePath: string,
+	{
+		postfix,
+	}: {
+		postfix?: string;
+	} = {}
+): Promise< TestFile > {
+	// Check whether the source file maps to a file.
+	// Note, if sourcePath is not found use console.error instead of throw:
+	// https://github.com/facebook/jest/issues/8688
+	try {
+		await fs.access( sourcePath );
+	} catch {
+		throw new Error( `Source file ${ sourcePath } not found on disk.` );
 	}
 
-	const extension = sourceFileName.split( '.' ).pop();
+	// Obtain the file extension.
+	const extension = path.extname( sourcePath );
 	if ( ! extension ) {
-		throw new Error( `Extension not found on source file ${ sourceFileName }` );
+		throw new Error( `Extension not found on source file ${ sourcePath }` );
+	}
+
+	// Generate a filename using current timestamp and a pseudo-randomly generated integer.
+	let filename = getTimestamp();
+	// If `postfix` is defined, use that as part of the final filename.
+	if ( postfix ) {
+		filename += `-${ postfix }`;
 	}
-	const basename = `${ filename }.${ sourceFileName.split( '.' ).pop() }`;
-	// Create test files in the same directory as the source file.
-	const dirname = path.join( __dirname, '' );
-	// Full path on disk of the source file, to be copied and renamed.
-	const sourceFilePath = path.join( dirname, sourceFileName );
 
-	const tempDir = await fs.mkdtemp( path.join( os.tmpdir(), 'e2e-' ) );
-	const testFilePath = path.join( tempDir, basename );
+	// Obtain the basename (filename with extension)
+	const basename = `${ filename }${ extension }`;
+
+	const tempDir = await fs.mkdtemp( path.join( os.tmpdir(), 'e2e' ) );
+	const targetPath = path.join( tempDir, basename );
 
-	await fs.copyFile( sourceFilePath, testFilePath );
+	await fs.copyFile( sourcePath, targetPath, constants.COPYFILE_EXCL );
 
 	// Return an object implementing the interface.
 	return {
-		fullpath: testFilePath,
-		dirname: dirname,
+		fullpath: targetPath,
+		dirname: tempDir,
 		basename: basename,
 		filename: filename,
 		extension: extension,
 	};
 }
-
-/**
- * Returns the path to a generated temporary JPEG image file.
- *
- * @returns {Promise<TestFile>} Object implementing the TestFile interface.
- */
-export async function createTestImage(): Promise< TestFile > {
-	return await createTestFile( { sourceFileName: 'image0.jpg' } );
-}
-
-/**
- * Returns the path to a generated temporary MP3 audio file.
- *
- * @returns {Promise<TestFile>} Object implementing the TestFile interface.
- */
-export async function createTestAudio(): Promise< TestFile > {
-	return await createTestFile( { sourceFileName: 'bees.mp3' } );
-}
-
-/**
- * Returns the path to an unsupported file.
- *
- * @returns {Promise<TestFile>} Object implementing the TestFile interface.
- */
-export async function createUnsupportedFile(): Promise< TestFile > {
-	return await createTestFile( { sourceFileName: 'unsupported_extension.mkv' } );
-}
diff --git a/packages/calypso-e2e/src/types.d.ts b/packages/calypso-e2e/src/types.d.ts
index 1c3295385e251..11ce20f1c6526 100644
--- a/packages/calypso-e2e/src/types.d.ts
+++ b/packages/calypso-e2e/src/types.d.ts
@@ -6,5 +6,3 @@ export type viewportSize = {
 	width: number;
 	height: number;
 };
-
-export type { TestFile } from './media-helper';
diff --git a/packages/calypso-e2e/test-files/bees.mp3 b/packages/calypso-e2e/test-files/bees.mp3
deleted file mode 100644
index fa82c60bf8541..0000000000000
Binary files a/packages/calypso-e2e/test-files/bees.mp3 and /dev/null differ
diff --git a/packages/calypso-e2e/test-files/image0.jpg b/packages/calypso-e2e/test-files/image0.jpg
deleted file mode 100644
index a92ae7592944f..0000000000000
Binary files a/packages/calypso-e2e/test-files/image0.jpg and /dev/null differ
diff --git a/packages/calypso-e2e/test-files/image1.jpg b/packages/calypso-e2e/test-files/image1.jpg
deleted file mode 100644
index 9dcc016b5db24..0000000000000
Binary files a/packages/calypso-e2e/test-files/image1.jpg and /dev/null differ
diff --git a/packages/calypso-e2e/test-files/image2.jpg b/packages/calypso-e2e/test-files/image2.jpg
deleted file mode 100644
index 92ef89cecbf17..0000000000000
Binary files a/packages/calypso-e2e/test-files/image2.jpg and /dev/null differ
diff --git a/packages/calypso-e2e/test-files/unsupported_extension.mkv b/packages/calypso-e2e/test-files/unsupported_extension.mkv
deleted file mode 100644
index a92ae7592944f..0000000000000
Binary files a/packages/calypso-e2e/test-files/unsupported_extension.mkv and /dev/null differ
diff --git a/test/e2e/lib/jest/environment.js b/test/e2e/lib/jest/environment.js
index 4a5961fccb902..37cdc6f2c9f25 100644
--- a/test/e2e/lib/jest/environment.js
+++ b/test/e2e/lib/jest/environment.js
@@ -2,6 +2,7 @@ const JestEnvironmentNode = require( 'jest-environment-node' );
 
 class JestEnvironmentE2E extends JestEnvironmentNode {
 	testFailed = false;
+	hookFailed = false;
 
 	async handleTestEvent( event ) {
 		switch ( event.name ) {
@@ -16,9 +17,20 @@ class JestEnvironmentE2E extends JestEnvironmentNode {
 				if ( this.testFailed ) {
 					event.test.mode = 'skip';
 				}
+				// With this flag enabled, all test cases in the describe
+				// block will be marked as failed.
+				// This way all other hooks (screenshot/recording) are run,
+				// and Jest correctly exits after those hooks are run.
+				if ( this.hookFailed ) {
+					event.test.mode = 'fail';
+				}
 				break;
 
 			case 'hook_failure':
+				this.global.__CURRENT_TEST_FAILED__ = true;
+				this.hookFailed = true;
+				break;
+
 			case 'test_fn_failure':
 				this.global.__CURRENT_TEST_FAILED__ = true;
 				this.testFailed = true;
diff --git a/test/e2e/specs/constants.js b/test/e2e/specs/constants.js
new file mode 100644
index 0000000000000..baca2996de5f9
--- /dev/null
+++ b/test/e2e/specs/constants.js
@@ -0,0 +1,11 @@
+import path from 'path';
+
+export const TEST_IMAGE_PATH = path.normalize(
+	path.join( __dirname, '..', 'image-uploads', 'image0.jpg' )
+);
+export const TEST_AUDIO_PATH = path.normalize(
+	path.join( __dirname, '..', 'image-uploads', 'bees.mp3' )
+);
+export const UNSUPPORTED_FILE_PATH = path.normalize(
+	path.join( __dirname, '..', 'image-uploads', 'unsupported_extension.mkv' )
+);
diff --git a/test/e2e/specs/specs-playwright/wp-blocks__coblocks.ts b/test/e2e/specs/specs-playwright/wp-blocks__coblocks.ts
index a20a4a3c583b7..a2634a637f950 100644
--- a/test/e2e/specs/specs-playwright/wp-blocks__coblocks.ts
+++ b/test/e2e/specs/specs-playwright/wp-blocks__coblocks.ts
@@ -2,7 +2,6 @@
  * @group gutenberg
  */
 
-import path from 'path';
 import {
 	setupHooks,
 	DataHelper,
@@ -15,11 +14,12 @@ import {
 	HeroBlock,
 	ClicktoTweetBlock,
 	LogosBlock,
+	TestFile,
 } from '@automattic/calypso-e2e';
 import { Page } from 'playwright';
-import type { TestFile } from '@automattic/calypso-e2e';
+import { TEST_IMAGE_PATH } from '../constants';
 
-describe( DataHelper.createSuiteTitle( 'Blocks: CoBlocks' ), () => {
+describe( DataHelper.createSuiteTitle( 'Blocks: CoBlocks' ), function () {
 	let gutenbergEditorPage: GutenbergEditorPage;
 	let pricingTableBlock: PricingTableBlock;
 	let page: Page;
@@ -31,12 +31,12 @@ describe( DataHelper.createSuiteTitle( 'Blocks: CoBlocks' ), () => {
 	const clicktoTweetBlockTweet =
 		'The foolish man seeks happiness in the distance. The wise grows it under his feet. — James Oppenheim';
 
-	setupHooks( ( args ) => {
+	setupHooks( ( args: { page: Page } ) => {
 		page = args.page;
 	} );
 
 	beforeAll( async () => {
-		logoImage = await MediaHelper.createTestImage();
+		logoImage = await MediaHelper.createTestFile( TEST_IMAGE_PATH );
 	} );
 
 	it( 'Log in', async function () {
@@ -105,6 +105,6 @@ describe( DataHelper.createSuiteTitle( 'Blocks: CoBlocks' ), () => {
 	);
 
 	it( `Confirm Logos block is visible in published post`, async () => {
-		await LogosBlock.validatePublishedContent( page, logoImage.basename );
+		await LogosBlock.validatePublishedContent( page, [ logoImage.filename ] );
 	} );
 } );
diff --git a/test/e2e/specs/specs-playwright/wp-blocks__media-spec.ts b/test/e2e/specs/specs-playwright/wp-blocks__media-spec.ts
index aab274b8d644c..f87abf0312f03 100644
--- a/test/e2e/specs/specs-playwright/wp-blocks__media-spec.ts
+++ b/test/e2e/specs/specs-playwright/wp-blocks__media-spec.ts
@@ -3,7 +3,6 @@
  * @group gutenberg
  */
 
-import path from 'path';
 import {
 	setupHooks,
 	DataHelper,
@@ -17,8 +16,9 @@ import {
 	TestFile,
 } from '@automattic/calypso-e2e';
 import { Page } from 'playwright';
+import { TEST_IMAGE_PATH, TEST_AUDIO_PATH } from '../constants';
 
-describe( DataHelper.createSuiteTitle( 'Blocks: Media (Upload)' ), () => {
+describe( DataHelper.createSuiteTitle( 'Blocks: Media (Upload)' ), function () {
 	let gutenbergEditorPage: GutenbergEditorPage;
 	let page: Page;
 	let testFiles: { image: TestFile; image_reserved_name: TestFile; audio: TestFile };
@@ -29,12 +29,11 @@ describe( DataHelper.createSuiteTitle( 'Blocks: Media (Upload)' ), () => {
 
 	beforeAll( async () => {
 		testFiles = {
-			image: await MediaHelper.createTestImage(),
-			image_reserved_name: await MediaHelper.createTestFile( {
-				sourceFileName: 'image0.jpg',
-				testFileName: 'filewith#?#?reservedurlchars',
+			image: await MediaHelper.createTestFile( TEST_IMAGE_PATH ),
+			image_reserved_name: await MediaHelper.createTestFile( TEST_IMAGE_PATH, {
+				postfix: 'filewith#?#?reservedurlchars',
 			} ),
-			audio: await MediaHelper.createTestAudio(),
+			audio: await MediaHelper.createTestFile( TEST_AUDIO_PATH ),
 		};
 	} );
 
@@ -84,22 +83,21 @@ describe( DataHelper.createSuiteTitle( 'Blocks: Media (Upload)' ), () => {
 		await gutenbergEditorPage.publish( { visit: true, saveDraft: true } );
 	} );
 
-	it( `Confirm Image block is visible in published post`, async () => {
-		await ImageBlock.validatePublishedContent( page, testFiles.image.filename );
+	it( `Confirm Image block is visible in published post`, async function () {
+		await ImageBlock.validatePublishedContent( page, [ testFiles.image.filename ] );
 	} );
 
-	it( `Confirm Image block is visible in published post (reserved name)`, async () => {
-		await ImageBlock.validatePublishedContent(
-			page,
-			testFiles.image_reserved_name.filename.replace( /[^a-zA-Z ]/g, '' )
-		);
+	it( `Confirm Image block is visible in published post (reserved name)`, async function () {
+		await ImageBlock.validatePublishedContent( page, [
+			testFiles.image_reserved_name.filename.replace( /[^a-zA-Z ]/g, '' ),
+		] );
 	} );
 
-	it( `Confirm Audio block is visible in published post`, async () => {
+	it( `Confirm Audio block is visible in published post`, async function () {
 		await AudioBlock.validatePublishedContent( page );
 	} );
 
-	it( `Confirm File block is visible in published post`, async () => {
-		await FileBlock.validatePublishedContent( page, testFiles.audio.filename );
+	it( `Confirm File block is visible in published post`, async function () {
+		await FileBlock.validatePublishedContent( page, [ testFiles.audio.filename ] );
 	} );
 } );
diff --git a/test/e2e/specs/specs-playwright/wp-media__edit-spec.js b/test/e2e/specs/specs-playwright/wp-media__edit-spec.ts
similarity index 87%
rename from test/e2e/specs/specs-playwright/wp-media__edit-spec.js
rename to test/e2e/specs/specs-playwright/wp-media__edit-spec.ts
index 12e1ddc7d478d..9247b75630db2 100644
--- a/test/e2e/specs/specs-playwright/wp-media__edit-spec.js
+++ b/test/e2e/specs/specs-playwright/wp-media__edit-spec.ts
@@ -9,18 +9,21 @@ import {
 	MediaPage,
 	SidebarComponent,
 	setupHooks,
+	TestFile,
 } from '@automattic/calypso-e2e';
+import { Page } from 'playwright';
+import { TEST_IMAGE_PATH } from '../constants';
 
 describe( DataHelper.createSuiteTitle( 'Media: Edit Media' ), function () {
-	let testImage;
-	let page;
+	let testImage: TestFile;
+	let page: Page;
 
 	setupHooks( ( args ) => {
 		page = args.page;
 	} );
 
 	beforeAll( async () => {
-		testImage = await MediaHelper.createTestImage();
+		testImage = await MediaHelper.createTestFile( TEST_IMAGE_PATH );
 	} );
 
 	describe.each`
@@ -28,7 +31,7 @@ describe( DataHelper.createSuiteTitle( 'Media: Edit Media' ), function () {
 		${ 'Simple' } | ${ 'defaultUser' }
 		${ 'Atomic' } | ${ 'wooCommerceUser' }
 	`( 'Edit Image ($siteType)', function ( { user } ) {
-		let mediaPage;
+		let mediaPage: MediaPage;
 
 		it( 'Log In', async function () {
 			const loginFlow = new LoginFlow( page, user );
diff --git a/test/e2e/specs/specs-playwright/wp-media__upload-spec.ts b/test/e2e/specs/specs-playwright/wp-media__upload-spec.ts
index 04934c1374e9c..d378a0a535c25 100644
--- a/test/e2e/specs/specs-playwright/wp-media__upload-spec.ts
+++ b/test/e2e/specs/specs-playwright/wp-media__upload-spec.ts
@@ -13,6 +13,7 @@ import {
 	TestFile,
 } from '@automattic/calypso-e2e';
 import { Page } from 'playwright';
+import { TEST_IMAGE_PATH, TEST_AUDIO_PATH, UNSUPPORTED_FILE_PATH } from '../constants';
 
 describe( DataHelper.createSuiteTitle( 'Media: Upload' ), () => {
 	let testFiles: { image: TestFile; audio: TestFile; unsupported: TestFile };
@@ -24,9 +25,9 @@ describe( DataHelper.createSuiteTitle( 'Media: Upload' ), () => {
 
 	beforeAll( async () => {
 		testFiles = {
-			image: await MediaHelper.createTestImage(),
-			audio: await MediaHelper.createTestAudio(),
-			unsupported: await MediaHelper.createUnsupportedFile(),
+			image: await MediaHelper.createTestFile( TEST_IMAGE_PATH ),
+			audio: await MediaHelper.createTestFile( TEST_AUDIO_PATH ),
+			unsupported: await MediaHelper.createTestFile( UNSUPPORTED_FILE_PATH ),
 		};
 	} );
 
@@ -53,18 +54,18 @@ describe( DataHelper.createSuiteTitle( 'Media: Upload' ), () => {
 		} );
 
 		it( 'Upload image and confirm addition to gallery', async () => {
-			const uploadedItem = await mediaPage.upload( testFiles.image );
+			const uploadedItem = await mediaPage.upload( testFiles.image.fullpath );
 			assert.strictEqual( await uploadedItem.isVisible(), true );
 		} );
 
 		it( 'Upload audio and confirm addition to gallery', async () => {
-			const uploadedItem = await mediaPage.upload( testFiles.audio );
+			const uploadedItem = await mediaPage.upload( testFiles.audio.fullpath );
 			assert.strictEqual( await uploadedItem.isVisible(), true );
 		} );
 
 		it( 'Upload an unsupported file type and see the rejection notice', async function () {
 			try {
-				await mediaPage.upload( testFiles.unsupported );
+				await mediaPage.upload( testFiles.unsupported.fullpath );
 			} catch ( error ) {
 				assert.match( error.message, /could not be uploaded/i );
 			}
diff --git a/test/e2e/tsconfig.json b/test/e2e/tsconfig.json
index e8e24bbf696b6..0ff0821b4906e 100644
--- a/test/e2e/tsconfig.json
+++ b/test/e2e/tsconfig.json
@@ -1,9 +1,9 @@
 {
 	"extends": "@automattic/calypso-build/typescript/ts-package.json",
 	"compilerOptions": {
+		"allowJs": true,
 		"noEmit": true, // just type checking, no output. The output is handled by babel.
 		"types": [ "jest", "node" ] // no mocha - we are only using TypeScript for the new Playwright scripts
 	},
-	// TypeScript is scoped only for the new Playwright scripts
-	"include": [ "specs/specs-playwright", "lib/gutenberg/tracking" ]
+	"include": [ "specs/specs-playwright", "specs/constants.js", "lib/gutenberg/tracking" ]
 }