diff --git a/src/acp/connection.py b/src/acp/connection.py
index 2799354..c054c9f 100644
--- a/src/acp/connection.py
+++ b/src/acp/connection.py
@@ -89,7 +89,11 @@ def __init__(
             self._recv_task = None
 
     async def close(self) -> None:
-        """Stop the receive loop and cancel any in-flight handler tasks."""
+        """Stop receiving and cancel other in-flight tasks.
+
+        A handler or async observer can await close itself. That calling task
+        is allowed to return; no response is guaranteed after transport closure.
+        """
         if self._closed:
             return
         self._closed = True
diff --git a/src/acp/task/supervisor.py b/src/acp/task/supervisor.py
index 2ed7ab4..48765ad 100644
--- a/src/acp/task/supervisor.py
+++ b/src/acp/task/supervisor.py
@@ -70,10 +70,13 @@ async def shutdown(self) -> None:
         self._closed = True
         if not self._tasks:
             return
-        tasks = list(self._tasks)
+        # A handler or async observer may close its own connection. Cancelling
+        # and gathering that caller would create a self-await cancellation cycle.
+        current = asyncio.current_task()
+        tasks = [task for task in self._tasks if task is not current]
         for task in tasks:
             task.cancel()
         # Failures were already routed to the error handlers by ``_on_done``; shutdown only
         # needs to wait for the tasks to finish, so don't let them escape from here.
         await asyncio.gather(*tasks, return_exceptions=True)
-        self._tasks.clear()
+        self._tasks.difference_update(tasks)
diff --git a/tests/test_reentrant_shutdown.py b/tests/test_reentrant_shutdown.py
new file mode 100644
index 0000000..9a50b70
--- /dev/null
+++ b/tests/test_reentrant_shutdown.py
@@ -0,0 +1,120 @@
+"""Closing a connection from its own task must not cancel/gather that task."""
+
+from __future__ import annotations
+
+import os
+import subprocess
+import sys
+from pathlib import Path
+
+import pytest
+
+
+@pytest.mark.parametrize("caller", ["notification", "request", "observer", "supervisor"])
+@pytest.mark.parametrize("siblings", [False, True])
+def test_shutdown_from_owned_task(caller: str, siblings: bool) -> None:
+    # A regression can poison cancellation cleanup with a self-await cycle.
+    # Run the real asyncio loop in a bounded child, not pytest's own loop.
+    source = r"""
+import asyncio
+from acp.connection import Connection
+from acp._transport import memory_transport_pair
+from acp.task import TaskSupervisor
+
+async def main():
+    finished = asyncio.Event()
+    sibling_started = asyncio.Event()
+    sibling_stopped = asyncio.Event()
+    supervisor = TaskSupervisor(source='test')
+    async def sibling():
+        sibling_started.set()
+        try:
+            await asyncio.Event().wait()
+        finally:
+            sibling_stopped.set()
+    if CALLER == 'supervisor':
+        async def owned():
+            if SIBLINGS:
+                supervisor.create(sibling())
+                await sibling_started.wait()
+            await supervisor.shutdown()
+            await asyncio.sleep(0)
+            assert not asyncio.current_task().cancelled()
+            if SIBLINGS:
+                assert sibling_stopped.is_set()
+            finished.set()
+        task = supervisor.create(owned())
+        await asyncio.wait_for(finished.wait(), 2)
+        await task
+        await supervisor.shutdown()
+        assert not supervisor._tasks
+        print('closed cleanly')
+        return
+    local, peer = memory_transport_pair()
+    async def handler(method, params, is_notification):
+        if CALLER == 'observer':
+            return None
+        await close_here()
+    async def observer(event):
+        if CALLER == 'observer':
+            await close_here()
+    connection = Connection(handler, local, observers=[observer] if CALLER == 'observer' else [])
+    async def close_here():
+        if SIBLINGS:
+            connection._tasks.create(sibling())
+            await sibling_started.wait()
+        await connection.close()
+        await asyncio.sleep(0)
+        assert not asyncio.current_task().cancelled()
+        if SIBLINGS:
+            assert sibling_stopped.is_set()
+        finished.set()
+    message = {'jsonrpc': '2.0', 'method': 'stop'}
+    if CALLER == 'request':
+        message['id'] = 1
+    await peer.send(message)
+    await asyncio.wait_for(finished.wait(), 2)
+    await asyncio.sleep(0)
+    await connection.close()
+    await peer.close()
+    assert not connection._tasks._tasks
+    print('closed cleanly')
+asyncio.run(main())
+"""
+    source = source.replace("CALLER", repr(caller)).replace("SIBLINGS", repr(siblings))
+    result = subprocess.run(  # noqa: S603 - bounded, fixed-source asyncio regression probe
+        [sys.executable, "-c", source],
+        capture_output=True,
+        text=True,
+        timeout=8,
+        env={**os.environ, "PYTHONPATH": str(Path(__file__).resolve().parents[1] / "src")},
+    )
+    assert result.returncode == 0, result.stdout + result.stderr
+    assert "closed cleanly" in result.stdout
+    assert "RecursionError" not in result.stderr
+    assert "Task was destroyed" not in result.stderr
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("siblings", [0, 2])
+async def test_external_shutdown_still_awaits_owned_task_cleanup(siblings: int) -> None:
+    import asyncio
+
+    from acp.task import TaskSupervisor
+
+    supervisor = TaskSupervisor(source="external-test")
+    stopped: list[int] = []
+
+    async def owned(index: int) -> None:
+        try:
+            await asyncio.Event().wait()
+        finally:
+            stopped.append(index)
+
+    tasks = [supervisor.create(owned(index)) for index in range(siblings)]
+    await asyncio.sleep(0)
+    await supervisor.shutdown()
+    assert sorted(stopped) == list(range(siblings))
+    assert all(task.cancelled() for task in tasks)
+    assert not supervisor._tasks
+    await supervisor.shutdown()