diff --git a/test/initialization.test.ts b/test/initialization.test.ts
index e28747b926..dc1babd18c 100644
--- a/test/initialization.test.ts
+++ b/test/initialization.test.ts
@@ -13,7 +13,8 @@ function ensureExtensionIsActive(): Promise<any> {
 }
 
 function waitForExtensionToBeActive(resolve): void {
-    if (!vscode.extensions.getExtension('Microsoft.mssql').isActive) {
+    if (typeof(vscode.extensions.getExtension('Microsoft.mssql')) === 'undefined' ||
+        !vscode.extensions.getExtension('Microsoft.mssql').isActive) {
         setTimeout(waitForExtensionToBeActive.bind(this, resolve), 50);
     } else {
         resolve();
@@ -26,10 +27,11 @@ suite('Initialization Tests', () => {
         Telemetry.disable();
     });
 
-    test('Connection manager is initialized properly', (done) => {
-        // Trigger extension activation
-        let uri = vscode.Uri.parse('untitled:test.sql');
-        vscode.workspace.openTextDocument(uri);
+    test('Connection manager is initialized properly', function(done): void { // Note: this can't be an arrow function (=>), otherwise this.timeout() breaks
+        this.timeout(10000); // Service installation usually takes a bit longer than the default 2000ms on a fresh install
+
+        // Force the extension to activate by running one of our commands
+        vscode.commands.executeCommand('extension.connect');
 
         // Wait for the extension to activate
         ensureExtensionIsActive().then(() => {