diff --git a/src/dumdum/client/app.py b/src/dumdum/client/app.py
index 55fc9f4..6f10d70 100644
--- a/src/dumdum/client/app.py
+++ b/src/dumdum/client/app.py
@@ -67,18 +67,13 @@ def submit(self, coro: Awaitable[Any]) -> concurrent.futures.Future:
         fut.add_done_callback(log_fut_exception)
         return fut
 
-    async def attempt_connection(self, host: str, port: int, nick: str) -> bool:
+    async def attempt_connection(self, host: str, port: int, nick: str) -> None:
         self.client = AsyncClient(nick, event_callback=self._handle_event_threadsafe)
 
         coro = self._run_connection(host, port)
         self._connection_task = asyncio.create_task(coro)
 
-        async with asyncio.TaskGroup() as tg:
-            auth_task = tg.create_task(self.client._wait_for_authentication())
-            tasks = [self._connection_task, auth_task]
-            await asyncio.wait(tasks, return_when=asyncio.FIRST_COMPLETED)
-
-        return await auth_task
+        await self.client._wait_for_authentication()
 
     def _connect_lifetime_with_event_thread(self, event_thread: EventThread) -> None:
         # In our application we'll be running an asyncio event loop in
diff --git a/src/dumdum/client/async_client.py b/src/dumdum/client/async_client.py
index 50c5bfa..8ce135a 100644
--- a/src/dumdum/client/async_client.py
+++ b/src/dumdum/client/async_client.py
@@ -12,12 +12,18 @@
 from .errors import AuthenticationFailedError
 
 
+def maybe_create_fut(last: asyncio.Future | None) -> asyncio.Future:
+    if last is None:
+        return asyncio.get_running_loop().create_future()
+    return last
+
+
 class AsyncClient:
     _reader: asyncio.StreamReader | None
     _writer: asyncio.StreamWriter | None
     _read_task: asyncio.Task | None
     _addr: str | None
-    _auth_fut: asyncio.Future[bool] | None
+    _auth_fut: asyncio.Future[bool | None] | None
 
     def __init__(
         self,
@@ -45,10 +51,18 @@ def addr(self) -> str:
     @contextlib.asynccontextmanager
     async def connect(self, host: str, port: int) -> AsyncIterator[Self]:
         self._addr = f"{host}:{port}"  # FIXME: must be canonicalized
-        self._reader, self._writer = await asyncio.open_connection(host, port)
+        self._auth_fut = maybe_create_fut(self._auth_fut)
+        try:
+            connector = asyncio.open_connection(host, port)
+            self._reader, self._writer = await connector
+        except BaseException:
+            self._set_authentication(None)
+            raise
+
         async with asyncio.TaskGroup() as tg:
             _read_coro = self._read_loop(self._reader, self._writer)
             self._read_task = tg.create_task(_read_coro)
+            self._read_task.add_done_callback(self._on_read_task_done)
 
             try:
                 success = await self._handshake()
@@ -101,16 +115,18 @@ async def _read_loop(
             self._handle_events(events)
             await writer.drain()  # exert backpressure
 
-    async def _handshake(self) -> bool:
+    def _on_read_task_done(self, task: asyncio.Task) -> None:
+        self._set_authentication(None)
+
+    async def _handshake(self) -> bool | None:
         assert self._writer is not None
         data = self._protocol.authenticate()
         self._writer.write(data)
         return await self._wait_for_authentication()
 
-    async def _wait_for_authentication(self) -> bool:
-        if self._auth_fut is None:
-            self._auth_fut = asyncio.get_running_loop().create_future()
-        return await self._auth_fut
+    async def _wait_for_authentication(self) -> bool | None:
+        self._auth_fut = maybe_create_fut(self._auth_fut)
+        return await asyncio.shield(self._auth_fut)
 
     def _handle_events(self, events: list[ClientEvent]) -> None:
         for event in events:
@@ -124,9 +140,10 @@ def _handle_event(self, event: ClientEvent) -> None:
             self._set_authentication(event.success)
         self._dispatch_event(event)
 
-    def _set_authentication(self, success: bool) -> None:
+    def _set_authentication(self, result: bool | None) -> None:
         assert self._auth_fut is not None
-        self._auth_fut.set_result(success)
+        if not self._auth_fut.done():
+            self._auth_fut.set_result(result)
 
     def _dispatch_event(self, event: ClientEvent) -> None:
         self.event_callback(event)