diff --git a/src/webhook_manager.py b/src/webhook_manager.py
index 267ceaa38..af28fe2a7 100644
--- a/src/webhook_manager.py
+++ b/src/webhook_manager.py
@@ -202,6 +202,18 @@ class WebhookManager:
         self._client = httpx.AsyncClient(timeout=10, follow_redirects=False)
         self._loop: Optional[asyncio.AbstractEventLoop] = None
         self._api_key_manager = api_key_manager
+        # Strong references to in-flight fire-and-forget tasks. asyncio only
+        # keeps weak references to tasks, so without this the GC can collect a
+        # delivery task mid-flight and the webhook is silently never sent.
+        self._bg_tasks: set = set()
+
+    def _spawn_tracked(self, coro):
+        """Schedule a background task and hold a strong reference until it
+        finishes, so it can't be garbage-collected before delivery completes."""
+        task = asyncio.ensure_future(coro)
+        self._bg_tasks.add(task)
+        task.add_done_callback(self._bg_tasks.discard)
+        return task
 
     def set_loop(self, loop: asyncio.AbstractEventLoop):
         self._loop = loop
@@ -223,8 +235,8 @@ class WebhookManager:
         if event not in ALLOWED_EVENTS:
             return
         try:
-            loop = asyncio.get_running_loop()
-            loop.create_task(self.fire(event, payload))
+            asyncio.get_running_loop()
+            self._spawn_tracked(self.fire(event, payload))
         except RuntimeError:
             # Called from a sync thread (e.g. sync FastAPI route in threadpool)
             if self._loop and self._loop.is_running():
@@ -243,7 +255,7 @@ class WebhookManager:
 
         for wh in matching:
             decrypted_secret = self._decrypt_secret(wh.secret)
-            asyncio.create_task(self._deliver(wh.id, wh.url, decrypted_secret, event, payload))
+            self._spawn_tracked(self._deliver(wh.id, wh.url, decrypted_secret, event, payload))
 
     async def deliver_test(self, webhook_id: str, url: str, encrypted_secret: Optional[str]):
         """Public method for the test-webhook route."""
diff --git a/tests/test_webhook_task_refs.py b/tests/test_webhook_task_refs.py
new file mode 100644
index 000000000..7b2c63697
--- /dev/null
+++ b/tests/test_webhook_task_refs.py
@@ -0,0 +1,55 @@
+"""Fire-and-forget webhook tasks must be referenced until they finish.
+
+asyncio keeps only a weak reference to a bare create_task() result, so a
+delivery task could be garbage-collected before it ran and the webhook silently
+dropped. WebhookManager now holds a strong reference for the task's lifetime and
+releases it on completion.
+"""
+import asyncio
+import sys
+
+# webhook_manager does `from src.database import SessionLocal, Webhook` at import
+# time. The shared test harness stubs src.database without Webhook, so ensure the
+# attribute exists before importing the manager. These tests never touch the DB
+# (the manager is built via __new__), so a placeholder class is sufficient.
+_db = sys.modules.get("src.database")
+if _db is not None and not hasattr(_db, "Webhook"):
+    _db.Webhook = type("Webhook", (), {})
+
+from src.webhook_manager import WebhookManager  # noqa: E402
+
+
+def test_spawn_tracked_holds_then_releases_reference():
+    async def run():
+        wm = WebhookManager.__new__(WebhookManager)
+        wm._bg_tasks = set()
+
+        gate = asyncio.Event()
+
+        async def work():
+            await gate.wait()
+
+        task = wm._spawn_tracked(work())
+        # Referenced while in flight (this is what stops GC from collecting it).
+        assert task in wm._bg_tasks
+        gate.set()
+        await task
+        # Reference released once done, so the set does not grow unbounded.
+        assert task not in wm._bg_tasks
+
+    asyncio.run(run())
+
+
+def test_spawn_tracked_runs_the_coroutine():
+    async def run():
+        wm = WebhookManager.__new__(WebhookManager)
+        wm._bg_tasks = set()
+        ran = []
+
+        async def work():
+            ran.append(True)
+
+        await wm._spawn_tracked(work())
+        assert ran == [True]
+
+    asyncio.run(run())