diff --git a/extensions/bluebubbles/src/monitor.test.ts b/extensions/bluebubbles/src/monitor.test.ts
index 0dcccbef8..96e85e84b 100644
--- a/extensions/bluebubbles/src/monitor.test.ts
+++ b/extensions/bluebubbles/src/monitor.test.ts
@@ -220,6 +220,12 @@ function createMockResponse(): ServerResponse & { body: string; statusCode: numb
   return res;
 }
 
+const flushAsync = async () => {
+  for (let i = 0; i < 2; i += 1) {
+    await new Promise<void>((resolve) => setImmediate(resolve));
+  }
+};
+
 describe("BlueBubbles webhook monitor", () => {
   let unregister: () => void;
 
@@ -506,7 +512,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(resolveChatGuidForTarget).toHaveBeenCalledWith(
         expect.objectContaining({
@@ -554,7 +560,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(resolveChatGuidForTarget).not.toHaveBeenCalled();
       expect(sendMessageBlueBubbles).toHaveBeenCalledWith(
@@ -601,7 +607,7 @@ describe("BlueBubbles webhook monitor", () => {
       await handleBlueBubblesWebhookRequest(req, res);
 
       // Wait for async processing
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(res.statusCode).toBe(200);
       expect(mockDispatchReplyWithBufferedBlockDispatcher).toHaveBeenCalled();
@@ -640,7 +646,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(res.statusCode).toBe(200);
       expect(mockDispatchReplyWithBufferedBlockDispatcher).not.toHaveBeenCalled();
@@ -681,7 +687,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockUpsertPairingRequest).toHaveBeenCalled();
       expect(mockDispatchReplyWithBufferedBlockDispatcher).not.toHaveBeenCalled();
@@ -724,7 +730,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockUpsertPairingRequest).toHaveBeenCalled();
       // Should not send pairing reply since created=false
@@ -765,7 +771,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockDispatchReplyWithBufferedBlockDispatcher).toHaveBeenCalled();
     });
@@ -802,7 +808,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockDispatchReplyWithBufferedBlockDispatcher).not.toHaveBeenCalled();
     });
@@ -842,7 +848,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockDispatchReplyWithBufferedBlockDispatcher).toHaveBeenCalled();
     });
@@ -880,7 +886,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockDispatchReplyWithBufferedBlockDispatcher).not.toHaveBeenCalled();
     });
@@ -919,7 +925,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockDispatchReplyWithBufferedBlockDispatcher).not.toHaveBeenCalled();
     });
@@ -958,7 +964,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockDispatchReplyWithBufferedBlockDispatcher).toHaveBeenCalled();
     });
@@ -999,7 +1005,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockDispatchReplyWithBufferedBlockDispatcher).toHaveBeenCalled();
       const callArgs = mockDispatchReplyWithBufferedBlockDispatcher.mock.calls[0][0];
@@ -1040,7 +1046,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockDispatchReplyWithBufferedBlockDispatcher).not.toHaveBeenCalled();
     });
@@ -1078,7 +1084,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockDispatchReplyWithBufferedBlockDispatcher).toHaveBeenCalled();
     });
@@ -1121,7 +1127,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockDispatchReplyWithBufferedBlockDispatcher).toHaveBeenCalled();
       const callArgs = mockDispatchReplyWithBufferedBlockDispatcher.mock.calls[0][0];
@@ -1167,7 +1173,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockDispatchReplyWithBufferedBlockDispatcher).toHaveBeenCalled();
       const callArgs = mockDispatchReplyWithBufferedBlockDispatcher.mock.calls[0][0];
@@ -1213,7 +1219,7 @@ describe("BlueBubbles webhook monitor", () => {
       const originalRes = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(originalReq, originalRes);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       // Only assert the reply message behavior below.
       mockDispatchReplyWithBufferedBlockDispatcher.mockClear();
@@ -1237,7 +1243,7 @@ describe("BlueBubbles webhook monitor", () => {
       const replyRes = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(replyReq, replyRes);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockDispatchReplyWithBufferedBlockDispatcher).toHaveBeenCalled();
       const callArgs = mockDispatchReplyWithBufferedBlockDispatcher.mock.calls[0][0];
@@ -1283,7 +1289,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockDispatchReplyWithBufferedBlockDispatcher).toHaveBeenCalled();
       const callArgs = mockDispatchReplyWithBufferedBlockDispatcher.mock.calls[0][0];
@@ -1331,7 +1337,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(sendBlueBubblesReaction).toHaveBeenCalledWith(
         expect.objectContaining({
@@ -1384,7 +1390,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       // Should process even without mention because it's an authorized control command
       expect(mockDispatchReplyWithBufferedBlockDispatcher).toHaveBeenCalled();
@@ -1427,7 +1433,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockDispatchReplyWithBufferedBlockDispatcher).not.toHaveBeenCalled();
     });
@@ -1470,7 +1476,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(markBlueBubblesChatRead).toHaveBeenCalled();
     });
@@ -1511,7 +1517,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(markBlueBubblesChatRead).not.toHaveBeenCalled();
     });
@@ -1554,7 +1560,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       // Should call typing start when reply flow triggers it.
       expect(sendBlueBubblesTyping).toHaveBeenCalledWith(
@@ -1604,7 +1610,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(sendBlueBubblesTyping).toHaveBeenCalledWith(
         expect.any(String),
@@ -1649,7 +1655,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(sendBlueBubblesTyping).toHaveBeenCalledWith(
         expect.any(String),
@@ -1697,7 +1703,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       // Outbound message ID uses short ID "2" (inbound msg-1 is "1", outbound msg-123 is "2")
       expect(mockEnqueueSystemEvent).toHaveBeenCalledWith(
@@ -1742,7 +1748,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockEnqueueSystemEvent).toHaveBeenCalledWith(
         expect.stringContaining("reaction added"),
@@ -1782,7 +1788,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockEnqueueSystemEvent).toHaveBeenCalledWith(
         expect.stringContaining("reaction removed"),
@@ -1822,7 +1828,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockEnqueueSystemEvent).not.toHaveBeenCalled();
     });
@@ -1860,7 +1866,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockEnqueueSystemEvent).toHaveBeenCalledWith(
         expect.stringContaining("👍"),
@@ -1901,7 +1907,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockDispatchReplyWithBufferedBlockDispatcher).toHaveBeenCalled();
       const callArgs = mockDispatchReplyWithBufferedBlockDispatcher.mock.calls[0][0];
@@ -1941,7 +1947,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       // The short ID "1" should resolve back to the full UUID
       expect(resolveBlueBubblesMessageId("1")).toBe("msg-uuid-12345");
@@ -1993,7 +1999,7 @@ describe("BlueBubbles webhook monitor", () => {
       const res = createMockResponse();
 
       await handleBlueBubblesWebhookRequest(req, res);
-      await new Promise((resolve) => setTimeout(resolve, 50));
+      await flushAsync();
 
       expect(mockDispatchReplyWithBufferedBlockDispatcher).not.toHaveBeenCalled();
     });
diff --git a/src/media/server.test.ts b/src/media/server.test.ts
index 875088cbf..693ba5940 100644
--- a/src/media/server.test.ts
+++ b/src/media/server.test.ts
@@ -14,6 +14,19 @@ vi.mock("./store.js", () => ({
 
 const { startMediaServer } = await import("./server.js");
 
+const waitForFileRemoval = async (file: string, timeoutMs = 200) => {
+  const start = Date.now();
+  while (Date.now() - start < timeoutMs) {
+    try {
+      await fs.stat(file);
+    } catch {
+      return;
+    }
+    await new Promise((resolve) => setTimeout(resolve, 5));
+  }
+  throw new Error(`timed out waiting for ${file} removal`);
+};
+
 describe("media server", () => {
   beforeAll(async () => {
     await fs.rm(MEDIA_DIR, { recursive: true, force: true });
@@ -32,8 +45,7 @@ describe("media server", () => {
     const res = await fetch(`http://localhost:${port}/media/file1`);
     expect(res.status).toBe(200);
     expect(await res.text()).toBe("hello");
-    await new Promise((r) => setTimeout(r, 600));
-    await expect(fs.stat(file)).rejects.toThrow();
+    await waitForFileRemoval(file);
     await new Promise((r) => server.close(r));
   });