diff --git a/authentik/core/models.py b/authentik/core/models.py
index 677627d64..fc88d10e8 100644
--- a/authentik/core/models.py
+++ b/authentik/core/models.py
@@ -494,8 +494,12 @@ class AuthenticatedSession(ExpiringModel):
     last_used = models.DateTimeField(auto_now=True)
 
     @staticmethod
-    def from_request(request: HttpRequest, user: User) -> "AuthenticatedSession":
+    def from_request(
+        request: HttpRequest, user: User
+    ) -> Optional["AuthenticatedSession"]:
         """Create a new session from a http request"""
+        if not hasattr(request, "session") or not request.session.session_key:
+            return None
         return AuthenticatedSession(
             session_key=request.session.session_key,
             user=user,
diff --git a/authentik/core/signals.py b/authentik/core/signals.py
index daca16ce1..497fbdc8b 100644
--- a/authentik/core/signals.py
+++ b/authentik/core/signals.py
@@ -49,7 +49,9 @@ def user_logged_in_session(sender, request: HttpRequest, user: "User", **_):
     """Create an AuthenticatedSession from request"""
     from authentik.core.models import AuthenticatedSession
 
-    AuthenticatedSession.from_request(request, user).save()
+    session = AuthenticatedSession.from_request(request, user)
+    if session:
+        session.save()
 
 
 @receiver(user_logged_out)