diff --git a/test/smoke/src/areas/preferences/preferences.test.ts b/test/smoke/src/areas/preferences/preferences.test.ts
index f1eb589b118..c7a1ce51475 100644
--- a/test/smoke/src/areas/preferences/preferences.test.ts
+++ b/test/smoke/src/areas/preferences/preferences.test.ts
@@ -34,4 +34,4 @@ export function setup() {
 			await app.workbench.settingsEditor.clearUserSettings();
 		});
 	});
-}
\ No newline at end of file
+}
diff --git a/test/smoke/src/areas/preferences/settings.ts b/test/smoke/src/areas/preferences/settings.ts
index cebd2f51497..de7bd1ffb43 100644
--- a/test/smoke/src/areas/preferences/settings.ts
+++ b/test/smoke/src/areas/preferences/settings.ts
@@ -30,7 +30,7 @@ export class SettingsEditor {
 
 	async clearUserSettings(): Promise<void> {
 		const settingsPath = path.join(this.userDataPath, 'User', 'settings.json');
-		await new Promise((c, e) => fs.writeFile(settingsPath, '{}', 'utf8', err => err ? e(err) : c()));
+		await new Promise((c, e) => fs.writeFile(settingsPath, '{\n}', 'utf8', err => err ? e(err) : c()));
 
 		await this.openSettings();
 		await this.editor.waitForEditorContents('settings.json', c => c === '{}');
@@ -39,4 +39,4 @@ export class SettingsEditor {
 	private async openSettings(): Promise<void> {
 		await this.quickopen.runCommand('Preferences: Open Settings (JSON)');
 	}
-}
\ No newline at end of file
+}
diff --git a/test/smoke/src/main.ts b/test/smoke/src/main.ts
index 935b16fb46c..4972be890f1 100644
--- a/test/smoke/src/main.ts
+++ b/test/smoke/src/main.ts
@@ -141,7 +141,8 @@ if (typeof stablePath === 'string' && !fs.existsSync(stablePath)) {
 	fail(`Can't find Stable Code at ${stablePath}.`);
 }
 
-const userDataDir = path.join(testDataPath, 'd');
+// TODO: Server should be launched from smoke tests
+const userDataDir = opts.web ? path.join(process.env.HOME!, '.vscode-remote/data') : path.join(testDataPath, 'd');
 
 let quality: Quality;
 if (process.env.VSCODE_DEV === '1') {
@@ -245,6 +246,11 @@ describe('Running Code', () => {
 		const app = new Application(this.defaultOptions);
 		await app!.start(opts.web ? false : undefined);
 		this.app = app;
+
+		// TODO: User data dir is not cleared for web yet
+		if (opts.web) {
+			await app.workbench.settingsEditor.clearUserSettings();
+		}
 	});
 
 	after(async function () {
@@ -273,7 +279,8 @@ describe('Running Code', () => {
 	}
 
 	if (opts.web) {
-		console.log('setup term tests only');
+		setupDataExplorerTests();
+		setupDataPreferencesTests();
 		setupTerminalTests();
 		return;
 	}
diff --git a/test/smoke/src/vscode/puppeteer-driver.ts b/test/smoke/src/vscode/puppeteer-driver.ts
index 12b56ebd202..fbe7b26db47 100644
--- a/test/smoke/src/vscode/puppeteer-driver.ts
+++ b/test/smoke/src/vscode/puppeteer-driver.ts
@@ -11,7 +11,13 @@ const height = 800;
 const vscodeToPuppeteerKey = {
 	cmd: 'Meta',
 	ctrl: 'Control',
-	enter: 'Enter'
+	enter: 'Enter',
+	escape: 'Escape',
+	right: 'ArrowRight',
+	up: 'ArrowUp',
+	down: 'ArrowDown',
+	left: 'ArrowLeft',
+	home: 'Home'
 };
 
 function buildDriver(browser: puppeteer.Browser, page: puppeteer.Page): IDriver {
@@ -24,18 +30,26 @@ function buildDriver(browser: puppeteer.Browser, page: puppeteer.Page): IDriver
 		reloadWindow: (windowId) => Promise.resolve(),
 		exitApplication: () => browser.close(),
 		dispatchKeybinding: async (windowId, keybinding) => {
-			const keys = keybinding.split('+');
-			const keysDown: string[] = [];
-			for (let i = 0; i < keys.length; i++) {
-				if (keys[i] in vscodeToPuppeteerKey) {
-					keys[i] = vscodeToPuppeteerKey[keys[i]];
+			const chords = keybinding.split(' ');
+			chords.forEach(async (chord, index) => {
+				if (index > 0) {
+					await timeout(100);
 				}
-				await page.keyboard.down(keys[i]);
-				keysDown.push(keys[i]);
-			}
-			while (keysDown.length > 0) {
-				await page.keyboard.up(keysDown.pop()!);
-			}
+				const keys = chord.split('+');
+				const keysDown: string[] = [];
+				for (let i = 0; i < keys.length; i++) {
+					if (keys[i] in vscodeToPuppeteerKey) {
+						keys[i] = vscodeToPuppeteerKey[keys[i]];
+					}
+					await page.keyboard.down(keys[i]);
+					keysDown.push(keys[i]);
+				}
+				while (keysDown.length > 0) {
+					await page.keyboard.up(keysDown.pop()!);
+				}
+			});
+
+			await timeout(100);
 		},
 		click: async (windowId, selector, xoffset, yoffset) => {
 			const { x, y } = await page.evaluate(`