diff --git a/src/auto-reply/inbound-debounce.ts b/src/auto-reply/inbound-debounce.ts
index 438adce5945..c8461639010 100644
--- a/src/auto-reply/inbound-debounce.ts
+++ b/src/auto-reply/inbound-debounce.ts
@@ -37,7 +37,6 @@ type DebounceBuffer<T> = {
   items: T[];
   timeout: ReturnType<typeof setTimeout> | null;
   debounceMs: number;
-  ready: Promise<void>;
   releaseReady: () => void;
   readyReleased: boolean;
   task: Promise<void>;
@@ -86,6 +85,27 @@ export function createInboundDebouncer<T>(params: InboundDebounceCreateParams<T>
     return next;
   };
 
+  const enqueueReservedKeyTask = (key: string, task: () => Promise<void>) => {
+    let readyReleased = false;
+    let releaseReady!: () => void;
+    const ready = new Promise<void>((resolve) => {
+      releaseReady = resolve;
+    });
+    return {
+      task: enqueueKeyTask(key, async () => {
+        await ready;
+        await task();
+      }),
+      release: () => {
+        if (readyReleased) {
+          return;
+        }
+        readyReleased = true;
+        releaseReady();
+      },
+    };
+  };
+
   const releaseBuffer = (buffer: DebounceBuffer<T>) => {
     if (buffer.readyReleased) {
       return;
@@ -132,13 +152,24 @@ export function createInboundDebouncer<T>(params: InboundDebounceCreateParams<T>
     const canDebounce = debounceMs > 0 && (params.shouldDebounce?.(item) ?? true);
 
     if (!canDebounce || !key) {
-      if (key && buffers.has(key)) {
-        await flushKey(key);
-      }
       if (key) {
-        await enqueueKeyTask(key, async () => {
+        if (!buffers.has(key)) {
+          await enqueueKeyTask(key, async () => {
+            await runFlush([item]);
+          });
+          return;
+        }
+        // Reserve the keyed immediate slot before forcing the pending buffer
+        // to flush so fire-and-forget callers cannot be overtaken.
+        const reservedTask = enqueueReservedKeyTask(key, async () => {
           await runFlush([item]);
         });
+        try {
+          await flushKey(key);
+        } finally {
+          reservedTask.release();
+        }
+        await reservedTask.task;
       } else {
         await runFlush([item]);
       }
@@ -153,25 +184,21 @@ export function createInboundDebouncer<T>(params: InboundDebounceCreateParams<T>
       return;
     }
 
-    let releaseReady!: () => void;
-    const buffer: DebounceBuffer<T> = {
-      items: [item],
-      timeout: null,
-      debounceMs,
-      ready: new Promise<void>((resolve) => {
-        releaseReady = resolve;
-      }),
-      releaseReady,
-      readyReleased: false,
-      task: Promise.resolve(),
-    };
-    buffer.task = enqueueKeyTask(key, async () => {
-      await buffer.ready;
+    let buffer!: DebounceBuffer<T>;
+    const reservedTask = enqueueReservedKeyTask(key, async () => {
       if (buffer.items.length === 0) {
         return;
       }
       await runFlush(buffer.items);
     });
+    buffer = {
+      items: [item],
+      timeout: null,
+      debounceMs,
+      releaseReady: reservedTask.release,
+      readyReleased: false,
+      task: reservedTask.task,
+    };
     buffers.set(key, buffer);
     scheduleFlush(key, buffer);
   };
diff --git a/src/auto-reply/inbound.test.ts b/src/auto-reply/inbound.test.ts
index 3f2fb63d188..2200c1c0554 100644
--- a/src/auto-reply/inbound.test.ts
+++ b/src/auto-reply/inbound.test.ts
@@ -401,6 +401,74 @@ describe("createInboundDebouncer", () => {
       setTimeoutSpy.mockRestore();
     }
   });
+
+  it("keeps fire-and-forget keyed work ahead of a later buffered item", async () => {
+    const started: string[] = [];
+    const finished: string[] = [];
+    let releaseFirst!: () => void;
+    const firstGate = new Promise<void>((resolve) => {
+      releaseFirst = resolve;
+    });
+
+    const setTimeoutSpy = vi.spyOn(globalThis, "setTimeout");
+    const debouncer = createInboundDebouncer<{ key: string; id: string; debounce: boolean }>({
+      debounceMs: 50,
+      buildKey: (item) => item.key,
+      shouldDebounce: (item) => item.debounce,
+      onFlush: async (items) => {
+        const ids = items.map((entry) => entry.id).join(",");
+        started.push(ids);
+        if (ids === "1") {
+          await firstGate;
+        }
+        finished.push(ids);
+      },
+    });
+
+    try {
+      await debouncer.enqueue({ key: "a", id: "1", debounce: true });
+
+      const firstTimerIndex = setTimeoutSpy.mock.calls.findLastIndex((call) => call[1] === 50);
+      expect(firstTimerIndex).toBeGreaterThanOrEqual(0);
+      clearTimeout(
+        setTimeoutSpy.mock.results[firstTimerIndex]?.value as ReturnType<typeof setTimeout>,
+      );
+      const firstFlush = (
+        setTimeoutSpy.mock.calls[firstTimerIndex]?.[0] as (() => Promise<void>) | undefined
+      )?.();
+
+      await vi.waitFor(() => {
+        expect(started).toEqual(["1"]);
+      });
+
+      const secondEnqueue = debouncer.enqueue({ key: "a", id: "2", debounce: false });
+      const thirdEnqueue = debouncer.enqueue({ key: "a", id: "3", debounce: true });
+
+      const thirdTimerIndex = setTimeoutSpy.mock.calls.findLastIndex(
+        (call, index) => index > firstTimerIndex && call[1] === 50,
+      );
+      expect(thirdTimerIndex).toBeGreaterThan(firstTimerIndex);
+      clearTimeout(
+        setTimeoutSpy.mock.results[thirdTimerIndex]?.value as ReturnType<typeof setTimeout>,
+      );
+      const thirdFlush = (
+        setTimeoutSpy.mock.calls[thirdTimerIndex]?.[0] as (() => Promise<void>) | undefined
+      )?.();
+
+      await Promise.resolve();
+
+      expect(started).toEqual(["1"]);
+      expect(finished).toEqual([]);
+
+      releaseFirst();
+      await Promise.all([firstFlush, secondEnqueue, thirdFlush, thirdEnqueue]);
+
+      expect(started).toEqual(["1", "2", "3"]);
+      expect(finished).toEqual(["1", "2", "3"]);
+    } finally {
+      setTimeoutSpy.mockRestore();
+    }
+  });
 });
 
 describe("initSessionState BodyStripped", () => {