diff --git a/test/smoke/src/areas/workbench/data-migration.test.ts b/test/smoke/src/areas/workbench/data-migration.test.ts
index d95a7c3e3a2..d0a158d2207 100644
--- a/test/smoke/src/areas/workbench/data-migration.test.ts
+++ b/test/smoke/src/areas/workbench/data-migration.test.ts
@@ -4,11 +4,10 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { Application, ApplicationOptions, Quality } from '../../../../automation';
-import { join } from 'path';
 import { ParsedArgs } from 'minimist';
-import { afterSuite, startApp } from '../../utils';
+import { afterSuite, getRandomUserDataDir, startApp } from '../../utils';
 
-export function setup(opts: ParsedArgs, testDataPath: string) {
+export function setup(opts: ParsedArgs) {
 
 	describe('Data Migration (insiders -> insiders)', () => {
 
@@ -90,7 +89,7 @@ export function setup(opts: ParsedArgs, testDataPath: string) {
 				this.retries(2);
 			}
 
-			const userDataDir = join(testDataPath, 'd2'); // different data dir from the other tests
+			const userDataDir = getRandomUserDataDir(this.defaultOptions);
 
 			const stableOptions: ApplicationOptions = Object.assign({}, this.defaultOptions);
 			stableOptions.codePath = stableCodePath;
@@ -133,7 +132,7 @@ export function setup(opts: ParsedArgs, testDataPath: string) {
 				this.skip();
 			}
 
-			const userDataDir = join(testDataPath, 'd3'); // different data dir from the other tests
+			const userDataDir = getRandomUserDataDir(this.defaultOptions);
 
 			const stableOptions: ApplicationOptions = Object.assign({}, this.defaultOptions);
 			stableOptions.codePath = stableCodePath;
diff --git a/test/smoke/src/main.ts b/test/smoke/src/main.ts
index fa6989e8b9d..f526eb19bf4 100644
--- a/test/smoke/src/main.ts
+++ b/test/smoke/src/main.ts
@@ -353,7 +353,7 @@ after(async function () {
 });
 
 describe(`VSCode Smoke Tests (${opts.web ? 'Web' : 'Electron'})`, () => {
-	if (!opts.web) { setupDataMigrationTests(opts, testDataPath); }
+	if (!opts.web) { setupDataMigrationTests(opts); }
 	if (!opts.web) { setupPreferencesTests(opts); }
 	setupSearchTests(opts);
 	setupNotebookTests(opts);
diff --git a/test/smoke/src/utils.ts b/test/smoke/src/utils.ts
index d4300a74be5..01f26878f93 100644
--- a/test/smoke/src/utils.ts
+++ b/test/smoke/src/utils.ts
@@ -30,11 +30,11 @@ export async function startApp(args: minimist.ParsedArgs, options: ApplicationOp
 		options = await optionsTransform({ ...options });
 	}
 
-	// https://github.com/microsoft/vscode/issues/34988
-	const userDataPathSuffix = [...Array(8)].map(() => Math.random().toString(36)[3]).join('');
-	const userDataDir = options.userDataDir.concat(`-${userDataPathSuffix}`);
+	const app = new Application({
+		...options,
+		userDataDir: getRandomUserDataDir(options)
+	});
 
-	const app = new Application({ ...options, userDataDir });
 	await app.start();
 
 	if (args.log) {
@@ -45,6 +45,16 @@ export async function startApp(args: minimist.ParsedArgs, options: ApplicationOp
 	return app;
 }
 
+export function getRandomUserDataDir(options: ApplicationOptions): string {
+
+	// Pick a random user data dir suffix that is not
+	// too long to not run into max path length issues
+	// https://github.com/microsoft/vscode/issues/34988
+	const userDataPathSuffix = [...Array(8)].map(() => Math.random().toString(36)[3]).join('');
+
+	return options.userDataDir.concat(`-${userDataPathSuffix}`);
+}
+
 export function afterSuite(opts: minimist.ParsedArgs, appFn?: () => Application | undefined, joinFn?: () => Promise<unknown>) {
 	after(async function () {
 		const app: Application = appFn?.() ?? this.app;