diff --git a/packages/calypso-e2e/src/index.ts b/packages/calypso-e2e/src/index.ts
index 22cc0562c8ba07..b3750a222277f2 100644
--- a/packages/calypso-e2e/src/index.ts
+++ b/packages/calypso-e2e/src/index.ts
@@ -3,6 +3,7 @@ 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 };
 
diff --git a/packages/calypso-e2e/src/media-helper.ts b/packages/calypso-e2e/src/media-helper.ts
index 52a94d3a75c578..43d6a2d2f0af3f 100644
--- a/packages/calypso-e2e/src/media-helper.ts
+++ b/packages/calypso-e2e/src/media-helper.ts
@@ -1,9 +1,21 @@
+import { constants } from 'fs';
 import fs from 'fs/promises';
 import os from 'os';
 import path from 'path';
 import config from 'config';
 import { getTimestamp } from './data-helper';
 
+/**
+ * Interface for holding various parts of a filepath.
+ */
+export interface TestFile {
+	fullpath: string; // eg. /usr/home/wp-calypso/test/e2e/image-uploads/image.jpg
+	dirname: string; // eg. /usr/home/wp-calypso/test/e2e/image-uploads/
+	basename: string; // eg. image.jpg
+	filename: string; // eg. image
+	extension: string; // eg. .jpg
+}
+
 const artifacts: { [ key: string ]: string } = config.get( 'artifacts' );
 
 /**
@@ -45,61 +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.
- * @returns {Promise<string>} Full path to the generated test file.
+ * @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< string > {
-	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.` );
 	}
 
-	// Reassign the variable with the final name to be used, including the extension.
-	fileName = `${ fileName }.${ sourceFileName.split( '.' ).pop() }`;
-
-	const sourceFileDir = path.join( __dirname, '../../../../../test/e2e/image-uploads/' );
-	const sourceFilePath = path.join( sourceFileDir, sourceFileName );
+	// Obtain the file extension.
+	const extension = path.extname( sourcePath );
+	if ( ! extension ) {
+		throw new Error( `Extension not found on source file ${ sourcePath }` );
+	}
 
-	const tempDir = await fs.mkdtemp( path.join( os.tmpdir(), 'e2e-' ) );
-	const testFilePath = path.join( tempDir, fileName );
+	// 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 }`;
+	}
 
-	await fs.copyFile( sourceFilePath, testFilePath );
+	// Obtain the basename (filename with extension)
+	const basename = `${ filename }${ extension }`;
 
-	return testFilePath;
-}
-
-/**
- * Returns the path to a generated temporary JPEG image file.
- *
- * @returns {Promise<string>} Full path on disk to the generated test file.
- */
-export async function createTestImage(): Promise< string > {
-	return await createTestFile( { sourceFileName: 'image0.jpg' } );
-}
+	const tempDir = await fs.mkdtemp( path.join( os.tmpdir(), 'e2e' ) );
+	const targetPath = path.join( tempDir, basename );
 
-/**
- * Returns the path to a generated temporary MP3 audio file.
- *
- * @returns {string} Full path on disk to the generated test file.
- */
-export async function createTestAudio(): Promise< string > {
-	return await createTestFile( { sourceFileName: 'bees.mp3' } );
-}
+	await fs.copyFile( sourcePath, targetPath, constants.COPYFILE_EXCL );
 
-/**
- * Returns the path to an unsupported file.
- *
- * @returns {string} Full path on disk to the generated test file.
- */
-export async function createInvalidFile(): Promise< string > {
-	return await createTestFile( { sourceFileName: 'unsupported_extension.mkv' } );
+	// Return an object implementing the interface.
+	return {
+		fullpath: targetPath,
+		dirname: tempDir,
+		basename: basename,
+		filename: filename,
+		extension: extension,
+	};
 }
diff --git a/test/e2e/lib/jest/environment.js b/test/e2e/lib/jest/environment.js
index 4a5961fccb9021..37cdc6f2c9f255 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 00000000000000..baca2996de5f94
--- /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 55bb5a82facde6..a2634a637f950a 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,
@@ -15,14 +14,16 @@ import {
 	HeroBlock,
 	ClicktoTweetBlock,
 	LogosBlock,
+	TestFile,
 } from '@automattic/calypso-e2e';
 import { Page } from 'playwright';
+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;
-	let logoImage: string;
+	let logoImage: TestFile;
 
 	// Test data
 	const pricingTableBlockPrice = 888;
@@ -30,12 +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 () {
@@ -78,7 +79,7 @@ describe( DataHelper.createSuiteTitle( 'Blocks: CoBlocks' ), () => {
 	it( `Insert ${ LogosBlock.blockName } block and set image`, async function () {
 		const blockHandle = await gutenbergEditorPage.addBlock( LogosBlock.blockName );
 		const logosBlock = new LogosBlock( blockHandle );
-		await logosBlock.upload( logoImage );
+		await logosBlock.upload( logoImage.fullpath );
 	} );
 
 	it( 'Publish and visit post', async function () {
@@ -104,6 +105,6 @@ describe( DataHelper.createSuiteTitle( 'Blocks: CoBlocks' ), () => {
 	);
 
 	it( `Confirm Logos block is visible in published post`, async () => {
-		await LogosBlock.validatePublishedContent( page, path.parse( logoImage ).name );
+		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 f60cee1d9618ed..f87abf0312f036 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,
@@ -14,13 +13,15 @@ import {
 	ImageBlock,
 	AudioBlock,
 	FileBlock,
+	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: string; image_reserved_name: string; audio: string };
+	let testFiles: { image: TestFile; image_reserved_name: TestFile; audio: TestFile };
 
 	setupHooks( ( args ) => {
 		page = args.page;
@@ -28,12 +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 ),
 		};
 	} );
 
@@ -55,47 +55,49 @@ describe( DataHelper.createSuiteTitle( 'Blocks: Media (Upload)' ), () => {
 	it( `${ ImageBlock.blockName } block: upload image file`, async function () {
 		const blockHandle = await gutenbergEditorPage.addBlock( ImageBlock.blockName );
 		const imageBlock = new ImageBlock( blockHandle );
-		await imageBlock.upload( testFiles.image );
+		await imageBlock.upload( testFiles.image.fullpath );
 	} );
 
 	it( `${ ImageBlock.blockName } block: upload image file with reserved URL characters`, async function () {
 		const blockHandle = await gutenbergEditorPage.addBlock( ImageBlock.blockName );
 		const imageBlock = new ImageBlock( blockHandle );
-		await imageBlock.upload( testFiles.image_reserved_name );
+		await imageBlock.upload( testFiles.image_reserved_name.fullpath );
 	} );
 
 	it( `${ AudioBlock.blockName } block: upload audio file`, async function () {
 		const blockHandle = await gutenbergEditorPage.addBlock( AudioBlock.blockName );
 		const audioBlock = new AudioBlock( blockHandle );
-		await audioBlock.upload( testFiles.audio );
+		await audioBlock.upload( testFiles.audio.fullpath );
 	} );
 
 	it( `${ FileBlock.blockName } block: upload audio file`, async function () {
 		const blockHandle = await gutenbergEditorPage.addBlock( FileBlock.blockName );
 		const fileBlock = new FileBlock( blockHandle );
-		await fileBlock.upload( testFiles.audio );
+		await fileBlock.upload( testFiles.audio.fullpath );
 	} );
 
 	it( 'Publish and visit post', async function () {
-		await gutenbergEditorPage.publish( { visit: true } );
+		// Must save as draft first to bypass issue with post-publish panel being auto-dismissed
+		// after publishing. May be related to the following issue?
+		// See https://github.com/Automattic/wp-calypso/issues/54421.
+		await gutenbergEditorPage.publish( { visit: true, saveDraft: true } );
 	} );
 
-	it( `Confirm Image block is visible in published post`, async () => {
-		await ImageBlock.validatePublishedContent( page, path.parse( testFiles.image ).name );
+	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,
-			path.parse( testFiles.image_reserved_name ).name.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, path.parse( testFiles.audio ).name );
+	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 86%
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 cbbfff2c0ba29f..9247b75630db29 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 );
@@ -51,7 +54,7 @@ describe( DataHelper.createSuiteTitle( 'Media: Edit Media' ), function () {
 		it( 'Upload image', async function () {
 			// Ideally, we'd not want to upload an image (that's a separate test)
 			// but occasionally, the photo gallery is cleaned out leaving no images.
-			const uploadedImageHandle = await mediaPage.upload( testImage );
+			const uploadedImageHandle = await mediaPage.upload( testImage.fullpath );
 			const isVisible = await uploadedImageHandle.isVisible();
 			expect( isVisible ).toBe( true );
 		} );
diff --git a/test/e2e/specs/specs-playwright/wp-media__upload-spec.js b/test/e2e/specs/specs-playwright/wp-media__upload-spec.ts
similarity index 67%
rename from test/e2e/specs/specs-playwright/wp-media__upload-spec.js
rename to test/e2e/specs/specs-playwright/wp-media__upload-spec.ts
index 90b4a40adfea13..d378a0a535c256 100644
--- a/test/e2e/specs/specs-playwright/wp-media__upload-spec.js
+++ b/test/e2e/specs/specs-playwright/wp-media__upload-spec.ts
@@ -10,11 +10,14 @@ import {
 	MediaPage,
 	SidebarComponent,
 	MediaHelper,
+	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;
-	let page;
+	let testFiles: { image: TestFile; audio: TestFile; unsupported: TestFile };
+	let page: Page;
 
 	setupHooks( ( args ) => {
 		page = args.page;
@@ -22,9 +25,9 @@ describe( DataHelper.createSuiteTitle( 'Media: Upload' ), () => {
 
 	beforeAll( async () => {
 		testFiles = {
-			image: await MediaHelper.createTestImage(),
-			audio: await MediaHelper.createTestAudio(),
-			invalid: await MediaHelper.createInvalidFile(),
+			image: await MediaHelper.createTestFile( TEST_IMAGE_PATH ),
+			audio: await MediaHelper.createTestFile( TEST_AUDIO_PATH ),
+			unsupported: await MediaHelper.createTestFile( UNSUPPORTED_FILE_PATH ),
 		};
 	} );
 
@@ -34,7 +37,7 @@ describe( DataHelper.createSuiteTitle( 'Media: Upload' ), () => {
 		${ 'Simple' } | ${ 'defaultUser' }
 		${ 'Atomic' } | ${ 'wooCommerceUser' }
 	`( 'Upload media files ($siteType)', ( { user } ) => {
-		let mediaPage;
+		let mediaPage: MediaPage;
 
 		it( 'Log In', async function () {
 			const loginFlow = new LoginFlow( page, user );
@@ -51,18 +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.invalid );
+				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 e8e24bbf696b68..0ff0821b4906eb 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" ]
 }