diff --git a/extensions/vscode-api-tests/src/singlefolder-tests/debug.test.ts b/extensions/vscode-api-tests/src/singlefolder-tests/debug.test.ts
index 0bf0eb23934..be3509a2bfa 100644
--- a/extensions/vscode-api-tests/src/singlefolder-tests/debug.test.ts
+++ b/extensions/vscode-api-tests/src/singlefolder-tests/debug.test.ts
@@ -39,14 +39,23 @@ suite('Debug', function () {
 
 	this.retries(2);
 	test('start debugging', async function () {
-		assert.equal(debug.activeDebugSession, undefined);
 		let stoppedEvents = 0;
 		let variablesReceived: () => void;
 		let initializedReceived: () => void;
 		let configurationDoneReceived: () => void;
+		const toDispose: Disposable[] = [];
+		if (debug.activeDebugSession) {
+			// We are re-running due to flakyness, make sure to clear out state
+			let sessionTerminatedRetry: () => void;
+			toDispose.push(debug.onDidTerminateDebugSession(() => {
+				sessionTerminatedRetry();
+			}));
+			const sessionTerminatedPromise = new Promise<void>(resolve => sessionTerminatedRetry = resolve);
+			await commands.executeCommand('workbench.action.debug.stop');
+			await sessionTerminatedPromise;
+		}
 
 		const firstVariablesRetrieved = new Promise<void>(resolve => variablesReceived = resolve);
-		const toDispose: Disposable[] = [];
 		toDispose.push(debug.registerDebugAdapterTrackerFactory('*', {
 			createDebugAdapterTracker: () => ({
 				onDidSendMessage: m => {