diff --git a/vscode/src/test/suite/helpers.ts b/vscode/src/test/suite/helpers.ts
index 6c48a8bfb3..1d3cfd1fff 100644
--- a/vscode/src/test/suite/helpers.ts
+++ b/vscode/src/test/suite/helpers.ts
@@ -70,3 +70,21 @@ export function createContext() {
     },
   } as unknown as FakeContext;
 }
+
+// Retries the given assertion function until it passes or the timeout (in ms) is exceeded.
+// Polls every 500ms. If the assertion never passes, the last assertion error is thrown.
+export async function retryForDuration(timeoutMs: number, fn: () => void) {
+  const deadline = Date.now() + timeoutMs;
+
+  while (Date.now() < deadline) {
+    try {
+      fn();
+      return;
+    } catch (_error) {
+      await new Promise((resolve) => setTimeout(resolve, 500));
+    }
+  }
+
+  // Final attempt — let it throw
+  fn();
+}
diff --git a/vscode/src/test/suite/testController.test.ts b/vscode/src/test/suite/testController.test.ts
index be904e49a1..cc80dcf2ea 100644
--- a/vscode/src/test/suite/testController.test.ts
+++ b/vscode/src/test/suite/testController.test.ts
@@ -749,7 +749,7 @@ suite("TestController", () => {
     assert.ok(runStub.started.calledWith(testItem));
     assert.ok(runStub.passed.calledWith(testItem));
     assert.ok(runStub.end.calledWithExactly());
-  }).timeout(10000);
+  }).timeout(30000);
 
   test("refresh handler clears all items and starts from scratch", async () => {
     await controller.testController.resolveHandler!(undefined);
diff --git a/vscode/src/test/suite/workspace.test.ts b/vscode/src/test/suite/workspace.test.ts
index ab8fb9aa88..fe5a20d35a 100644
--- a/vscode/src/test/suite/workspace.test.ts
+++ b/vscode/src/test/suite/workspace.test.ts
@@ -10,7 +10,7 @@ import { beforeEach, afterEach } from "mocha";
 import { Workspace } from "../../workspace";
 
 import { FAKE_TELEMETRY } from "./fakeTelemetry";
-import { createContext, FakeContext } from "./helpers";
+import { createContext, FakeContext, retryForDuration } from "./helpers";
 
 suite("Workspace", () => {
   let workspacePath: string;
@@ -56,13 +56,13 @@ suite("Workspace", () => {
       fs.rmSync(path.join(gitDir, "rebase-apply"));
     }
 
-    // Give enough time for all watchers to fire and all debounces to run off
-    await new Promise((resolve) => setTimeout(resolve, 10000));
-
-    // The start call only happens once because of the inhibitRestart flag
-    assert.strictEqual(startStub.callCount, 1);
-    // The restart call only happens once because of the debounce
-    assert.strictEqual(restartSpy.callCount, 1);
+    // Retry assertions for up to 30 seconds to allow watchers and debounces to fire
+    await retryForDuration(30000, () => {
+      // The start call only happens once because of the inhibitRestart flag
+      assert.strictEqual(startStub.callCount, 1);
+      // The restart call only happens once because of the debounce
+      assert.strictEqual(restartSpy.callCount, 1);
+    });
   }).timeout(60000);
 
   test("does not restart when watched files are touched without modifying contents", async () => {