diff --git a/authentik/root/middleware.py b/authentik/root/middleware.py
index 62a1f4cc7..2e9133181 100644
--- a/authentik/root/middleware.py
+++ b/authentik/root/middleware.py
@@ -1,4 +1,5 @@
 """Dynamically set SameSite depending if the upstream connection is TLS or not"""
+from hashlib import sha512
 from time import time
 from typing import Callable
 
@@ -10,11 +11,14 @@ from django.http.request import HttpRequest
 from django.http.response import HttpResponse
 from django.utils.cache import patch_vary_headers
 from django.utils.http import http_date
+from jwt import PyJWTError, decode, encode
 from structlog.stdlib import get_logger
 
 from authentik.lib.utils.http import get_client_ip
 
 LOGGER = get_logger("authentik.asgi")
+ACR_AUTHENTIK_SESSION = "goauthentik.io/core/default"
+SIGNING_HASH = sha512(settings.SECRET_KEY.encode()).hexdigest()
 
 
 class SessionMiddleware(UpstreamSessionMiddleware):
@@ -35,6 +39,18 @@ class SessionMiddleware(UpstreamSessionMiddleware):
             return True
         return False
 
+    def process_request(self, request):
+        session_jwt = request.COOKIES.get(settings.SESSION_COOKIE_NAME)
+        # We need to support the standard django format of just a session key
+        # for testing setups, where the session is directly set
+        session_key = session_jwt if settings.TEST else None
+        try:
+            session_payload = decode(session_jwt, SIGNING_HASH, algorithms=["HS256"])
+            session_key = session_payload["sid"]
+        except (KeyError, PyJWTError):
+            pass
+        request.session = self.SessionStore(session_key)
+
     def process_response(self, request: HttpRequest, response: HttpResponse) -> HttpResponse:
         """
         If request.session was modified, or if the configuration is to save the
@@ -82,9 +98,21 @@ class SessionMiddleware(UpstreamSessionMiddleware):
                             "request completed. The user may have logged "
                             "out in a concurrent request, for example."
                         )
+                    payload = {
+                        "sid": request.session.session_key,
+                        "iss": "authentik",
+                        "sub": "anonymous",
+                        "authenticated": request.user.is_authenticated,
+                        "acr": ACR_AUTHENTIK_SESSION,
+                    }
+                    if request.user.is_authenticated:
+                        payload["sub"] = request.user.uid
+                    value = encode(payload=payload, key=SIGNING_HASH)
+                    if settings.TEST:
+                        value = request.session.session_key
                     response.set_cookie(
                         settings.SESSION_COOKIE_NAME,
-                        request.session.session_key,
+                        value,
                         max_age=max_age,
                         expires=expires,
                         domain=settings.SESSION_COOKIE_DOMAIN,
diff --git a/authentik/root/settings.py b/authentik/root/settings.py
index 9098ae917..2f75491c2 100644
--- a/authentik/root/settings.py
+++ b/authentik/root/settings.py
@@ -216,7 +216,8 @@ CACHES = {
 DJANGO_REDIS_SCAN_ITERSIZE = 1000
 DJANGO_REDIS_IGNORE_EXCEPTIONS = True
 DJANGO_REDIS_LOG_IGNORED_EXCEPTIONS = True
-SESSION_ENGINE = "django.contrib.sessions.backends.cache"
+SESSION_ENGINE = "django.contrib.sessions.backends.cached_db"
+SESSION_SERIALIZER = "django.contrib.sessions.serializers.PickleSerializer"
 SESSION_CACHE_ALIAS = "default"
 # Configured via custom SessionMiddleware
 # SESSION_COOKIE_SAMESITE = "None"