diff --git a/packages/calypso-e2e/src/media-helper.ts b/packages/calypso-e2e/src/media-helper.ts
index cd15d03ed8b11c..43d6a2d2f0af3f 100644
--- a/packages/calypso-e2e/src/media-helper.ts
+++ b/packages/calypso-e2e/src/media-helper.ts
@@ -77,15 +77,13 @@ export async function createTestFile(
 	try {
 		await fs.access( sourcePath );
 	} catch {
-		console.error( `Source file ${ sourcePath } not found on disk.` );
-		throw new Error();
+		throw new Error( `Source file ${ sourcePath } not found on disk.` );
 	}
 
 	// Obtain the file extension.
 	const extension = path.extname( sourcePath );
 	if ( ! extension ) {
-		console.error( `Extension not found on source file ${ sourcePath }` );
-		throw new Error();
+		throw new Error( `Extension not found on source file ${ sourcePath }` );
 	}
 
 	// Generate a filename using current timestamp and a pseudo-randomly generated integer.
diff --git a/test/e2e/lib/jest/environment.js b/test/e2e/lib/jest/environment.js
index 4a5961fccb9021..ac22d4704b8418 100644
--- a/test/e2e/lib/jest/environment.js
+++ b/test/e2e/lib/jest/environment.js
@@ -19,6 +19,9 @@ class JestEnvironmentE2E extends JestEnvironmentNode {
 				break;
 
 			case 'hook_failure':
+				console.error( event.error );
+				this.testFailed = true;
+				break;
 			case 'test_fn_failure':
 				this.global.__CURRENT_TEST_FAILED__ = true;
 				this.testFailed = true;