diff --git a/authentik/core/models.py b/authentik/core/models.py
index efd7ec686..501b556c7 100644
--- a/authentik/core/models.py
+++ b/authentik/core/models.py
@@ -322,6 +322,8 @@ class ExpiringModel(models.Model):
     @property
     def is_expired(self) -> bool:
         """Check if token is expired yet."""
+        if not self.expiring:
+            return False
         return now() > self.expires
 
     class Meta:
diff --git a/authentik/core/tests/test_models.py b/authentik/core/tests/test_models.py
new file mode 100644
index 000000000..cb0444632
--- /dev/null
+++ b/authentik/core/tests/test_models.py
@@ -0,0 +1,26 @@
+"""authentik core models tests"""
+from time import sleep
+
+from django.test import TestCase
+from django.utils.timezone import now
+from guardian.shortcuts import get_anonymous_user
+
+from authentik.core.models import Token
+
+
+class TestModels(TestCase):
+    """Test Models"""
+
+    def test_token_expire(self):
+        """Test token expiring"""
+        token = Token.objects.create(expires=now(), user=get_anonymous_user())
+        sleep(0.5)
+        self.assertTrue(token.is_expired)
+
+    def test_token_expire_no_expire(self):
+        """Test token expiring with "expiring" set """
+        token = Token.objects.create(
+            expires=now(), user=get_anonymous_user(), expiring=False
+        )
+        sleep(0.5)
+        self.assertFalse(token.is_expired)
diff --git a/authentik/lib/sentry.py b/authentik/lib/sentry.py
index 189f0d264..0decc5f6c 100644
--- a/authentik/lib/sentry.py
+++ b/authentik/lib/sentry.py
@@ -1,4 +1,6 @@
 """authentik sentry integration"""
+from typing import Optional
+
 from aioredis.errors import ConnectionClosedError, ReplyError
 from billiard.exceptions import WorkerLostError
 from botocore.client import ClientError
@@ -22,7 +24,7 @@ class SentryIgnoredException(Exception):
     """Base Class for all errors that are suppressed, and not sent to sentry."""
 
 
-def before_send(event: dict, hint: dict) -> dict:
+def before_send(event: dict, hint: dict) -> Optional[dict]:
     """Check if error is database error, and ignore if so"""
     ignored_classes = (
         # Inbuilt types
diff --git a/authentik/lib/tests/test_sentry.py b/authentik/lib/tests/test_sentry.py
index 023c82ba1..ba899dabb 100644
--- a/authentik/lib/tests/test_sentry.py
+++ b/authentik/lib/tests/test_sentry.py
@@ -10,9 +10,9 @@ class TestSentry(TestCase):
     def test_error_not_sent(self):
         """Test SentryIgnoredError not sent"""
         self.assertIsNone(
-            before_send(None, {"exc_info": (0, SentryIgnoredException(), 0)})
+            before_send({}, {"exc_info": (0, SentryIgnoredException(), 0)})
         )
 
     def test_error_sent(self):
         """Test error sent"""
-        self.assertIsNone(before_send(None, {"exc_info": (0, ValueError(), 0)}))
+        self.assertEqual({}, before_send({}, {"exc_info": (0, ValueError(), 0)}))