diff --git a/plextraktsync/cli.py b/plextraktsync/cli.py
index 36bc630654..8d6a75d275 100644
--- a/plextraktsync/cli.py
+++ b/plextraktsync/cli.py
@@ -33,6 +33,7 @@ def wrap(*args, **kwargs):
 
                 logger = logging.getLogger(__name__)
                 logger.fatal(f"Error running {name} command: {str(e)}")
+                raise
             except Exception as e:
                 from plextraktsync.factory import logging
 
diff --git a/plextraktsync/commands/watch.py b/plextraktsync/commands/watch.py
index d7d5309221..f35471ac0c 100644
--- a/plextraktsync/commands/watch.py
+++ b/plextraktsync/commands/watch.py
@@ -1,5 +1,8 @@
 from __future__ import annotations
 
+from click import ClickException
+from trakt.errors import OAuthRefreshException
+
 from plextraktsync.factory import factory
 from plextraktsync.watch.events import (
     ActivityNotification,
@@ -11,26 +14,30 @@
 
 
 def watch(server: str):
-    factory.run_config.update(
-        server=server,
-    )
-    ws = factory.web_socket_listener
-    updater = factory.watch_state_updater
+    try:
+        factory.watch_fatal_error.clear()
+        factory.run_config.update(
+            server=server,
+        )
+        ws = factory.web_socket_listener
+        updater = factory.watch_state_updater
 
-    ws.on(ServerStarted, updater.on_start)
-    ws.on(
-        PlaySessionStateNotification,
-        updater.on_play,
-        state=["playing", "stopped", "paused"],
-    )
-    ws.on(
-        ActivityNotification,
-        updater.on_activity,
-        type="library.refresh.items",
-        event="ended",
-        progress=100,
-    )
-    ws.on(TimelineEntry, updater.on_delete, state=9, metadata_state="deleted")
-    ws.on(Error, updater.on_error)
+        ws.on(ServerStarted, updater.on_start)
+        ws.on(
+            PlaySessionStateNotification,
+            updater.on_play,
+            state=["playing", "stopped", "paused"],
+        )
+        ws.on(
+            ActivityNotification,
+            updater.on_activity,
+            type="library.refresh.items",
+            event="ended",
+            progress=100,
+        )
+        ws.on(TimelineEntry, updater.on_delete, state=9, metadata_state="deleted")
+        ws.on(Error, updater.on_error)
 
-    ws.listen()
+        ws.listen()
+    except OAuthRefreshException as e:
+        raise ClickException(f"Trakt error: Unable to refresh token: {e}") from e
diff --git a/plextraktsync/factory/Factory.py b/plextraktsync/factory/Factory.py
index 10bd6e8df5..e81c6d769b 100644
--- a/plextraktsync/factory/Factory.py
+++ b/plextraktsync/factory/Factory.py
@@ -211,7 +211,7 @@ def enable_self_update(self):
     def web_socket_listener(self):
         from plextraktsync.watch.WebSocketListener import WebSocketListener
 
-        return WebSocketListener(plex=self.plex_server)
+        return WebSocketListener(plex=self.plex_server, fatal_error=self.watch_fatal_error)
 
     @cached_property
     def watch_state_updater(self):
@@ -224,6 +224,12 @@ def watch_state_updater(self):
             config=self.config,
         )
 
+    @cached_property
+    def watch_fatal_error(self):
+        from plextraktsync.watch.FatalErrorState import FatalErrorState
+
+        return FatalErrorState()
+
     @cached_property
     def logging(self):
         import logging
@@ -324,7 +330,7 @@ def queue(self):
             TraktMarkWatchedWorker(),
             TraktScrobbleWorker(),
         ]
-        task = BackgroundTask(self.batch_delay_timer, *workers)
+        task = BackgroundTask(self.batch_delay_timer, *workers, fatal_error=self.watch_fatal_error)
         queue = Queue(task)
 
         return queue
diff --git a/plextraktsync/media/MediaFactory.py b/plextraktsync/media/MediaFactory.py
index 38ca9d3b96..d0c32a2560 100644
--- a/plextraktsync/media/MediaFactory.py
+++ b/plextraktsync/media/MediaFactory.py
@@ -4,7 +4,7 @@
 
 from plexapi.exceptions import PlexApiException
 from requests import RequestException
-from trakt.errors import TraktException
+from trakt.errors import OAuthRefreshException, TraktException
 
 from plextraktsync.factory import logging
 from plextraktsync.media.Media import Media
@@ -66,6 +66,8 @@ def resolve_guid(self, guid: PlexGuid, show: Media = None):
                 tm = self.trakt.find_episode_guid(guid, show.seasons)
             else:
                 tm = self.trakt.find_by_guid(guid)
+        except OAuthRefreshException:
+            raise
         except (TraktException, RequestException) as e:
             self.logger.warning(
                 f"{guid.title_link}: Skipping {guid}: Trakt errors: {e}",
diff --git a/plextraktsync/queue/BackgroundTask.py b/plextraktsync/queue/BackgroundTask.py
index b7f6455a74..9558217ceb 100644
--- a/plextraktsync/queue/BackgroundTask.py
+++ b/plextraktsync/queue/BackgroundTask.py
@@ -4,6 +4,8 @@
 from queue import Empty
 from typing import TYPE_CHECKING
 
+from trakt.errors import OAuthRefreshException
+
 from plextraktsync.factory import logging
 
 if TYPE_CHECKING:
@@ -20,10 +22,11 @@ class BackgroundTask:
 
     logger = logging.getLogger(__name__)
 
-    def __init__(self, timer: Timer = None, *tasks):
+    def __init__(self, timer: Timer = None, *tasks, fatal_error=None):
         self.queues = defaultdict(list)
         self.timer = timer
         self.tasks = tasks
+        self.fatal_error = fatal_error
 
     def check_timer(self):
         if not self.timer:
@@ -40,6 +43,11 @@ def timed_events(self):
         for task in self.tasks:
             try:
                 task(self.queues)
+            except OAuthRefreshException as e:
+                if self.fatal_error is not None:
+                    self.fatal_error.set(e)
+                    return
+                raise
             except Exception as e:
                 self.logger.error(f"Got exception while working on {task}: {e}")
 
@@ -60,6 +68,9 @@ def __call__(self, queue: SimpleQueue):
         """
 
         while True:
+            if self.fatal_error is not None:
+                self.fatal_error.raise_if_set()
+
             try:
                 message = queue.get(timeout=1)
             except Empty:
@@ -67,7 +78,12 @@ def __call__(self, queue: SimpleQueue):
             else:
                 if message is None:
                     self.shutdown()
+                    if self.fatal_error is not None:
+                        self.fatal_error.raise_if_set()
                     break
                 self.process_message(message)
 
             self.check_timer()
+
+            if self.fatal_error is not None:
+                self.fatal_error.raise_if_set()
diff --git a/plextraktsync/watch/EventDispatcher.py b/plextraktsync/watch/EventDispatcher.py
index 315a38037d..59a09fe5ff 100644
--- a/plextraktsync/watch/EventDispatcher.py
+++ b/plextraktsync/watch/EventDispatcher.py
@@ -1,5 +1,7 @@
 from __future__ import annotations
 
+from trakt.errors import OAuthRefreshException
+
 from plextraktsync.factory import logging
 from plextraktsync.watch.EventFactory import EventFactory
 from plextraktsync.watch.events import Error, ServerStarted
@@ -38,6 +40,8 @@ def dispatch(self, event):
 
             try:
                 listener["listener"](event)
+            except OAuthRefreshException:
+                raise
             except Exception as e:
                 self.logger.error(f"{type(e).__name__} was raised: {e}")
 
diff --git a/plextraktsync/watch/FatalErrorState.py b/plextraktsync/watch/FatalErrorState.py
new file mode 100644
index 0000000000..755044e416
--- /dev/null
+++ b/plextraktsync/watch/FatalErrorState.py
@@ -0,0 +1,25 @@
+from __future__ import annotations
+
+from threading import Lock
+
+
+class FatalErrorState:
+    def __init__(self):
+        self._error = None
+        self._lock = Lock()
+
+    def clear(self):
+        with self._lock:
+            self._error = None
+
+    def set(self, error: Exception):
+        with self._lock:
+            if self._error is None:
+                self._error = error
+
+    def raise_if_set(self):
+        with self._lock:
+            error = self._error
+
+        if error is not None:
+            raise error
diff --git a/plextraktsync/watch/WebSocketListener.py b/plextraktsync/watch/WebSocketListener.py
index fe6a274e2b..fe0df7c9d4 100644
--- a/plextraktsync/watch/WebSocketListener.py
+++ b/plextraktsync/watch/WebSocketListener.py
@@ -3,6 +3,8 @@
 from time import sleep
 from typing import TYPE_CHECKING
 
+from trakt.errors import OAuthRefreshException
+
 from plextraktsync.factory import logging
 from plextraktsync.watch.EventDispatcher import EventDispatcher
 from plextraktsync.watch.events import Error, ServerStarted
@@ -14,24 +16,38 @@
 class WebSocketListener:
     logger = logging.getLogger(__name__)
 
-    def __init__(self, plex: PlexServer, poll_interval=5, restart_interval=15):
+    def __init__(self, plex: PlexServer, poll_interval=5, restart_interval=15, fatal_error=None):
         self.plex = plex
         self.poll_interval = poll_interval
         self.restart_interval = restart_interval
+        self.fatal_error = fatal_error
         self.dispatcher = EventDispatcher()
 
     def on(self, event_type, listener, **kwargs):
         self.dispatcher.on(event_type, listener, **kwargs)
 
+    def event_handler(self, data):
+        try:
+            return self.dispatcher.event_handler(data)
+        except OAuthRefreshException as e:
+            if self.fatal_error is not None:
+                self.fatal_error.set(e)
+            raise
+
     def listen(self):
         self.logger.info("Listening for events!")
         while True:
-            notifier = self.plex.startAlertListener(callback=self.dispatcher.event_handler)
-            self.dispatcher.event_handler(ServerStarted(notifier=notifier))
+            if self.fatal_error is not None:
+                self.fatal_error.raise_if_set()
+
+            notifier = self.plex.startAlertListener(callback=self.event_handler)
+            self.event_handler(ServerStarted(notifier=notifier))
 
             while notifier.is_alive():
                 sleep(self.poll_interval)
+                if self.fatal_error is not None:
+                    self.fatal_error.raise_if_set()
 
-            self.dispatcher.event_handler(Error(msg="Server closed connection"))
+            self.event_handler(Error(msg="Server closed connection"))
             self.logger.error(f"Listener finished. Restarting in {self.restart_interval} seconds")
             sleep(self.restart_interval)
diff --git a/tests/conftest.py b/tests/conftest.py
index 6179cef285..17aa275e7b 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -6,6 +6,7 @@
 from os.path import dirname
 from os.path import join as join_path
 
+from trakt.errors import OAuthRefreshException
 from trakt.tv import TVShow
 
 from plextraktsync.factory import Factory
@@ -35,3 +36,17 @@ def make(cls=None, **kwargs) -> TVShow:
     cls = cls if cls is not None else "object"
     # https://stackoverflow.com/a/2827726/2314626
     return type(cls, (object,), kwargs)
+
+
+def make_oauth_refresh_exception(
+    error: str = "invalid_grant",
+    error_description: str = "The provided authorization grant is invalid.",
+) -> OAuthRefreshException:
+    response = make(
+        cls="Response",
+        json=lambda self: {
+            "error": error,
+            "error_description": error_description,
+        },
+    )()
+    return OAuthRefreshException(response)
diff --git a/tests/test_events.py b/tests/test_events.py
index 4a2c6aef73..37ff037b7a 100755
--- a/tests/test_events.py
+++ b/tests/test_events.py
@@ -1,10 +1,13 @@
 #!/usr/bin/env python3 -m pytest
 from __future__ import annotations
 
+import pytest
+from trakt.errors import OAuthRefreshException
+
 from plextraktsync.watch.EventDispatcher import EventDispatcher
 from plextraktsync.watch.EventFactory import EventFactory
 from plextraktsync.watch.events import ActivityNotification
-from tests.conftest import load_mock
+from tests.conftest import load_mock, make_oauth_refresh_exception
 
 
 def test_events():
@@ -73,3 +76,23 @@ def test_event_dispatcher():
     dispatcher = EventDispatcher().on(ActivityNotification, lambda x: events.append(x), event=["ended"], progress=99)
     dispatcher.event_handler(raw_events[4])
     assert len(events) == 0, "No match for event=ended and progress=99"
+
+
+def test_event_dispatcher_reraises_oauth_refresh_exception():
+    dispatcher = EventDispatcher().on(
+        ActivityNotification,
+        lambda _: (_ for _ in ()).throw(make_oauth_refresh_exception()),
+    )
+
+    with pytest.raises(OAuthRefreshException):
+        dispatcher.dispatch(
+            ActivityNotification(
+                Activity={
+                    "event": "ended",
+                    "type": "library.refresh.items",
+                    "progress": 100,
+                    "Context": {"key": "/library/metadata/1"},
+                },
+                event="ended",
+            )
+        )
diff --git a/tests/test_watch_fatal_error.py b/tests/test_watch_fatal_error.py
new file mode 100644
index 0000000000..4febd27325
--- /dev/null
+++ b/tests/test_watch_fatal_error.py
@@ -0,0 +1,73 @@
+#!/usr/bin/env python3 -m pytest
+from __future__ import annotations
+
+import pytest
+from trakt.errors import OAuthRefreshException
+
+from plextraktsync.queue.BackgroundTask import BackgroundTask
+from plextraktsync.watch.FatalErrorState import FatalErrorState
+from plextraktsync.watch.WebSocketListener import WebSocketListener
+from tests.conftest import make_oauth_refresh_exception
+
+
+def test_background_task_records_oauth_refresh_exception():
+    fatal_error = FatalErrorState()
+
+    def task(_queues):
+        raise make_oauth_refresh_exception()
+
+    background_task = BackgroundTask(None, task, fatal_error=fatal_error)
+    background_task.timed_events()
+
+    with pytest.raises(OAuthRefreshException):
+        fatal_error.raise_if_set()
+
+
+def test_background_task_continues_without_fatal_error():
+    fatal_error = FatalErrorState()
+    calls = []
+
+    class Queue:
+        def __init__(self):
+            self.messages = iter([
+                ("test", 1),
+                None,
+            ])
+
+        def get(self, timeout):
+            return next(self.messages)
+
+    def task(queues):
+        calls.append(list(queues["test"]))
+
+    background_task = BackgroundTask(None, task, fatal_error=fatal_error)
+    background_task(Queue())
+
+    assert calls == [[1]]
+
+
+def test_websocket_listener_raises_recorded_oauth_refresh_exception(monkeypatch):
+    fatal_error = FatalErrorState()
+
+    class Notifier:
+        def __init__(self):
+            self.calls = 0
+
+        def is_alive(self):
+            self.calls += 1
+            return self.calls == 1
+
+    class Plex:
+        def startAlertListener(self, callback):
+            self.callback = callback
+            return Notifier()
+
+    def fail_sleep(_interval):
+        fatal_error.set(make_oauth_refresh_exception())
+
+    monkeypatch.setattr("plextraktsync.watch.WebSocketListener.sleep", fail_sleep)
+
+    listener = WebSocketListener(Plex(), poll_interval=0, fatal_error=fatal_error)
+
+    with pytest.raises(OAuthRefreshException):
+        listener.listen()
\ No newline at end of file