diff --git a/test/smoke/src/areas/extensions/extensions.test.ts b/test/smoke/src/areas/extensions/extensions.test.ts
index 9bf6dd79b07..de5b4fa91c6 100644
--- a/test/smoke/src/areas/extensions/extensions.test.ts
+++ b/test/smoke/src/areas/extensions/extensions.test.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { Application, Logger } from '../../../../automation';
-import { installAllHandlers } from '../../utils';
+import { installAllHandlers, retryWithRestart } from '../../utils';
 
 export function setup(logger: Logger) {
 	describe('Extensions', () => {
@@ -13,18 +13,19 @@ export function setup(logger: Logger) {
 		installAllHandlers(logger);
 
 		it('install and enable vscode-smoketest-check extension', async function () {
-			this.retries(3); // https://github.com/microsoft/vscode/issues/146800
+			this.timeout(2 * 60 * 1000); // https://github.com/microsoft/vscode/issues/146800
 
 			const app = this.app as Application;
+			await retryWithRestart(app, async () => {
+				await app.workbench.extensions.openExtensionsViewlet();
+				await app.workbench.extensions.installExtension('ms-vscode.vscode-smoketest-check', true);
 
-			await app.workbench.extensions.openExtensionsViewlet();
-			await app.workbench.extensions.installExtension('ms-vscode.vscode-smoketest-check', true);
+				// Close extension editor because keybindings dispatch is not working when web views are opened and focused
+				// https://github.com/microsoft/vscode/issues/110276
+				await app.workbench.extensions.closeExtension('vscode-smoketest-check');
 
-			// Close extension editor because keybindings dispatch is not working when web views are opened and focused
-			// https://github.com/microsoft/vscode/issues/110276
-			await app.workbench.extensions.closeExtension('vscode-smoketest-check');
-
-			await app.workbench.quickaccess.runCommand('Smoke Test Check');
+				await app.workbench.quickaccess.runCommand('Smoke Test Check');
+			});
 		});
 	});
 }
diff --git a/test/smoke/src/areas/workbench/localization.test.ts b/test/smoke/src/areas/workbench/localization.test.ts
index 61b354a22f3..2b8704b72ff 100644
--- a/test/smoke/src/areas/workbench/localization.test.ts
+++ b/test/smoke/src/areas/workbench/localization.test.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { Logger, Application } from '../../../../automation';
-import { installAllHandlers } from '../../utils';
+import { installAllHandlers, retryWithRestart } from '../../utils';
 
 export function setup(logger: Logger) {
 
@@ -14,27 +14,30 @@ export function setup(logger: Logger) {
 		installAllHandlers(logger);
 
 		it('starts with "DE" locale and verifies title and viewlets text is in German', async function () {
-			this.retries(3); // https://github.com/microsoft/vscode/issues/146800
+			this.timeout(2 * 60 * 1000); // https://github.com/microsoft/vscode/issues/146800
 
 			const app = this.app as Application;
-			await app.workbench.extensions.openExtensionsViewlet();
-			await app.workbench.extensions.installExtension('ms-ceintl.vscode-language-pack-de', false);
-			await app.restart({ extraArgs: ['--locale=DE'] });
 
-			const result = await app.workbench.localization.getLocalizedStrings();
-			const localeInfo = await app.workbench.localization.getLocaleInfo();
+			await retryWithRestart(app, async () => {
+				await app.workbench.extensions.openExtensionsViewlet();
+				await app.workbench.extensions.installExtension('ms-ceintl.vscode-language-pack-de', false);
+				await app.restart({ extraArgs: ['--locale=DE'] });
 
-			if (localeInfo.locale === undefined || localeInfo.locale.toLowerCase() !== 'de') {
-				throw new Error(`The requested locale for VS Code was not German. The received value is: ${localeInfo.locale === undefined ? 'not set' : localeInfo.locale}`);
-			}
+				const result = await app.workbench.localization.getLocalizedStrings();
+				const localeInfo = await app.workbench.localization.getLocaleInfo();
 
-			if (localeInfo.language.toLowerCase() !== 'de') {
-				throw new Error(`The UI language is not German. It is ${localeInfo.language}`);
-			}
+				if (localeInfo.locale === undefined || localeInfo.locale.toLowerCase() !== 'de') {
+					throw new Error(`The requested locale for VS Code was not German. The received value is: ${localeInfo.locale === undefined ? 'not set' : localeInfo.locale}`);
+				}
 
-			if (result.open.toLowerCase() !== 'öffnen' || result.close.toLowerCase() !== 'schließen' || result.find.toLowerCase() !== 'finden') {
-				throw new Error(`Received wrong German localized strings: ${JSON.stringify(result, undefined, 0)}`);
-			}
+				if (localeInfo.language.toLowerCase() !== 'de') {
+					throw new Error(`The UI language is not German. It is ${localeInfo.language}`);
+				}
+
+				if (result.open.toLowerCase() !== 'öffnen' || result.close.toLowerCase() !== 'schließen' || result.find.toLowerCase() !== 'finden') {
+					throw new Error(`Received wrong German localized strings: ${JSON.stringify(result, undefined, 0)}`);
+				}
+			});
 		});
 	});
 }
diff --git a/test/smoke/src/utils.ts b/test/smoke/src/utils.ts
index 1272924181b..bfcbd5f9e18 100644
--- a/test/smoke/src/utils.ts
+++ b/test/smoke/src/utils.ts
@@ -149,6 +149,21 @@ export function timeout(i: number) {
 	});
 }
 
+export async function retryWithRestart(app: Application, testFn: () => Promise<unknown>, retries = 3, timeoutMs = 20000): Promise<unknown> {
+	for (let i = 0; i < retries; i++) {
+		const result = await Promise.race([
+			testFn().then(() => true, error => { throw error; }),
+			timeout(timeoutMs).then(() => false)
+		]);
+
+		if (result) {
+			return;
+		}
+
+		await app.restart();
+	}
+}
+
 export interface ITask<T> {
 	(): T;
 }