diff --git a/authentik/outposts/models.py b/authentik/outposts/models.py
index b84f0e02a6..871de3cff6 100644
--- a/authentik/outposts/models.py
+++ b/authentik/outposts/models.py
@@ -152,7 +152,7 @@ class OutpostServiceConnection(ScheduledModel, models.Model):
 
         state = cache.get(self.state_key, None)
         if not state:
-            outpost_service_connection_monitor.send(self.pk)
+            outpost_service_connection_monitor.send_with_options(args=(self.pk), rel_obj=self)
             return OutpostServiceConnectionState("", False)
         return state
 
@@ -165,9 +165,11 @@ class OutpostServiceConnection(ScheduledModel, models.Model):
 
     @property
     def schedule_specs(self) -> list[ScheduleSpec]:
+        from authentik.outposts.tasks import outpost_service_connection_monitor
+
         return [
             ScheduleSpec(
-                actor_name="authentik.outposts.tasks.outpost_service_connection_monitor",
+                actor_name=outpost_service_connection_monitor.actor_name,
                 uid=self.pk,
                 args=(self.pk,),
                 crontab="3-59/15 * * * *",
@@ -315,9 +317,11 @@ class Outpost(ScheduledModel, SerializerModel, ManagedModel):
 
     @property
     def schedule_specs(self) -> list[ScheduleSpec]:
+        from authentik.outposts.tasks import outpost_controller
+
         return [
             ScheduleSpec(
-                actor_name="authentik.outposts.tasks.outpost_controller",
+                actor_name=outpost_controller.actor_name,
                 uid=self.pk,
                 args=(self.pk,),
                 kwargs={"action": "up", "from_cache": False},
diff --git a/authentik/outposts/signals.py b/authentik/outposts/signals.py
index 37b9fb777b..0a2145e420 100644
--- a/authentik/outposts/signals.py
+++ b/authentik/outposts/signals.py
@@ -39,14 +39,22 @@ def pre_save_outpost(sender, instance: Outpost, **_):
     if bool(dirty):
         LOGGER.info("Outpost needs re-deployment due to changes", instance=instance)
         cache.set(CACHE_KEY_OUTPOST_DOWN % instance.pk.hex, old_instance)
-        outpost_controller.send(instance.pk.hex, action="down", from_cache=True)
+        outpost_controller.send_with_options(
+            args=(instance.pk.hex,),
+            kwargs={"action": "down", "from_cache": True},
+            rel_obj=instance,
+        )
 
 
 @receiver(m2m_changed, sender=Outpost.providers.through)
 def m2m_changed_update(sender, instance: Model, action: str, **_):
     """Update outpost on m2m change, when providers are added or removed"""
     if action in ["post_add", "post_remove", "post_clear"]:
-        outpost_post_save.send(class_to_path(instance.__class__), instance.pk)
+        outpost_post_save.send_with_options(
+            args=(class_to_path(instance.__class__), instance.pk),
+            # TODO: how do we get the outpost here, if it makes sense
+            rel_obj=None,
+        )
 
 
 @receiver(post_save)
@@ -64,7 +72,11 @@ def post_save_update(sender, instance: Model, created: bool, **_):
     if isinstance(instance, Outpost) and created:
         LOGGER.info("New outpost saved, ensuring initial token and user are created")
         _ = instance.token
-    outpost_post_save.send(class_to_path(instance.__class__), instance.pk)
+    outpost_post_save.send_with_options(
+        args=(class_to_path(instance.__class__), instance.pk),
+        # TODO: how do we get the outpost here, if it makes sense
+        rel_obj=None,
+    )
 
 
 @receiver(pre_delete, sender=Outpost)
diff --git a/authentik/outposts/tasks.py b/authentik/outposts/tasks.py
index 6010e90388..3fcbafa305 100644
--- a/authentik/outposts/tasks.py
+++ b/authentik/outposts/tasks.py
@@ -104,7 +104,8 @@ def outpost_service_connection_monitor(connection_pk: Any):
 @actor
 def outpost_controller(outpost_pk: str, action: str = "up", from_cache: bool = False):
     """Create/update/monitor/delete the deployment of an Outpost"""
-    self: Task = CurrentTask.get_task()
+    self = CurrentTask.get_task()
+    self.set_uid(outpost_pk)
     logs = []
     if from_cache:
         outpost: Outpost = cache.get(CACHE_KEY_OUTPOST_DOWN % outpost_pk)
@@ -125,11 +126,11 @@ def outpost_controller(outpost_pk: str, action: str = "up", from_cache: bool = F
             logs = getattr(controller, f"{action}_with_logs")()
             LOGGER.debug("-----------------Outpost Controller logs end-------------------")
     except (ControllerException, ServiceConnectionInvalid) as exc:
-        self.set_error(exc)
+        self.error(exc)
     else:
         if from_cache:
             cache.delete(CACHE_KEY_OUTPOST_DOWN % outpost_pk)
-        self.set_status(TaskStatus.SUCCESSFUL, *logs)
+        self.info(*logs)
 
 
 @actor
@@ -137,15 +138,12 @@ def outpost_token_ensurer():
     """
     Periodically ensure that all Outposts have valid Service Accounts and Tokens
     """
-    self: Task = CurrentTask.get_task()
+    self = CurrentTask.get_task()
     all_outposts = Outpost.objects.all()
     for outpost in all_outposts:
         _ = outpost.token
         outpost.build_user_permissions(outpost.user)
-    self.set_status(
-        TaskStatus.SUCCESSFUL,
-        f"Successfully checked {len(all_outposts)} Outposts.",
-    )
+    self.info(f"Successfully checked {len(all_outposts)} Outposts.")
 
 
 @actor