diff --git a/authentik/api/apps.py b/authentik/api/apps.py
index 86e817eea..664fcf9fa 100644
--- a/authentik/api/apps.py
+++ b/authentik/api/apps.py
@@ -18,7 +18,6 @@ class AuthentikAPIConfig(AppConfig):
 
         # Class is defined here as it needs to be created early enough that drf-spectacular will
         # find it, but also won't cause any import issues
-
         # pylint: disable=unused-variable
         class TokenSchema(OpenApiAuthenticationExtension):
             """Auth schema"""
diff --git a/authentik/outposts/models.py b/authentik/outposts/models.py
index 47486bc2f..0e2d54b12 100644
--- a/authentik/outposts/models.py
+++ b/authentik/outposts/models.py
@@ -8,7 +8,7 @@ from uuid import uuid4
 from dacite import from_dict
 from django.contrib.auth.models import Permission
 from django.core.cache import cache
-from django.db import models, transaction
+from django.db import IntegrityError, models, transaction
 from django.db.models.base import Model
 from django.utils.translation import gettext_lazy as _
 from docker.client import DockerClient
@@ -380,21 +380,24 @@ class Outpost(models.Model):
         tokens = Token.filter_not_expired(
             identifier=self.token_identifier,
             intent=TokenIntents.INTENT_API,
-        )
-        if tokens.exists():
-            token = tokens.first()
-            if not token.managed:
-                token.managed = managed
-                token.save()
-            return token
-        return Token.objects.create(
-            user=self.user,
-            identifier=self.token_identifier,
-            intent=TokenIntents.INTENT_API,
-            description=f"Autogenerated by authentik for Outpost {self.name}",
-            expiring=False,
             managed=managed,
         )
+        if tokens.exists():
+            return tokens.first()
+        try:
+            return Token.objects.create(
+                user=self.user,
+                identifier=self.token_identifier,
+                intent=TokenIntents.INTENT_API,
+                description=f"Autogenerated by authentik for Outpost {self.name}",
+                expiring=False,
+                managed=managed,
+            )
+        except IntegrityError:
+            # Integrity error happens mostly when managed is re-used
+            Token.objects.filter(managed=managed).delete()
+            Token.objects.filter(identifier=self.token_identifier).delete()
+            return self.token
 
     def get_required_objects(self) -> Iterable[Union[models.Model, str]]:
         """Get an iterator of all objects the user needs read access to"""