diff --git a/authentik/outposts/controllers/k8s/base.py b/authentik/outposts/controllers/k8s/base.py
index 95abcc8b9..cfc43840d 100644
--- a/authentik/outposts/controllers/k8s/base.py
+++ b/authentik/outposts/controllers/k8s/base.py
@@ -42,7 +42,7 @@ class KubernetesObjectReconciler(Generic[T]):
     def __init__(self, controller: "KubernetesController"):
         self.controller = controller
         self.namespace = controller.outpost.config.kubernetes_namespace
-        self.logger = get_logger()
+        self.logger = get_logger().bind(type=self.__class__.__name__)
 
     @property
     def name(self) -> str:
@@ -79,7 +79,7 @@ class KubernetesObjectReconciler(Generic[T]):
                 self.delete(current)
             else:
                 self.logger.debug("No old found, creating")
-            self.logger.debug("Created")
+            self.logger.debug("Creating")
             self.create(reference)
         except NeedsUpdate:
             self.logger.debug("Updating")
diff --git a/authentik/providers/proxy/controllers/k8s/traefik.py b/authentik/providers/proxy/controllers/k8s/traefik.py
new file mode 100644
index 000000000..2a75c01f7
--- /dev/null
+++ b/authentik/providers/proxy/controllers/k8s/traefik.py
@@ -0,0 +1,160 @@
+"""Kubernetes Traefik Middleware Reconciler"""
+from dataclasses import asdict, dataclass, field
+from typing import TYPE_CHECKING
+
+from dacite import from_dict
+from kubernetes.client import ApiextensionsV1Api, CustomObjectsApi
+
+from authentik.outposts.controllers.base import FIELD_MANAGER
+from authentik.outposts.controllers.k8s.base import (
+    Disabled,
+    KubernetesObjectReconciler,
+    NeedsUpdate,
+)
+from authentik.providers.proxy.models import ProxyProvider
+
+if TYPE_CHECKING:
+    from authentik.outposts.controllers.kubernetes import KubernetesController
+
+
+@dataclass
+class TraefikMiddlewareSpecForwardAuth:
+    """traefik middleware forwardAuth spec"""
+
+    address: str
+    # pylint: disable=invalid-name
+    authResponseHeaders: list[str]
+    # pylint: disable=invalid-name
+    trustForwardHeader: bool
+
+
+@dataclass
+class TraefikMiddlewareSpec:
+    """Traefik middleware spec"""
+
+    # pylint: disable=invalid-name
+    forwardAuth: TraefikMiddlewareSpecForwardAuth
+
+
+@dataclass
+class TraefikMiddlewareMetadata:
+    """Traefik Middleware metadata"""
+
+    name: str
+    namespace: str
+    labels: dict = field(default_factory=dict)
+
+
+@dataclass
+class TraefikMiddleware:
+    """Traefik Middleware"""
+
+    # pylint: disable=invalid-name
+    apiVersion: str
+    kind: str
+    metadata: TraefikMiddlewareMetadata
+    spec: TraefikMiddlewareSpec
+
+
+CRD_NAME = "middlewares.traefik.containo.us"
+CRD_GROUP = "traefik.containo.us"
+CRD_VERSION = "v1alpha1"
+CRD_PLURAL = "middlewares"
+
+
+class TraefikMiddlewareReconciler(KubernetesObjectReconciler[TraefikMiddleware]):
+    """Kubernetes Traefik Middleware Reconciler"""
+
+    def __init__(self, controller: "KubernetesController") -> None:
+        super().__init__(controller)
+        self.api_ex = ApiextensionsV1Api(controller.client)
+        self.api = CustomObjectsApi(controller.client)
+
+    def _crd_exists(self) -> bool:
+        """Check if the traefik middleware exists"""
+        return bool(
+            len(
+                self.api_ex.list_custom_resource_definition(
+                    field_selector=f"metadata.name={CRD_NAME}"
+                ).items
+            )
+        )
+
+    def reconcile(self, current: TraefikMiddleware, reference: TraefikMiddleware):
+        super().reconcile(current, reference)
+        if current.spec.forwardAuth.address != reference.spec.forwardAuth.address:
+            raise NeedsUpdate()
+
+    def get_reference_object(self) -> TraefikMiddleware:
+        """Get deployment object for outpost"""
+        if not ProxyProvider.objects.filter(
+            outpost__in=[self.controller.outpost],
+            forward_auth_mode=True,
+        ).exists():
+            raise Disabled()
+        if not self._crd_exists():
+            raise Disabled()
+        return TraefikMiddleware(
+            apiVersion=f"{CRD_GROUP}/{CRD_VERSION}",
+            kind="Middleware",
+            metadata=TraefikMiddlewareMetadata(
+                name=self.name,
+                namespace=self.namespace,
+                labels=self.get_object_meta().labels,
+            ),
+            spec=TraefikMiddlewareSpec(
+                forwardAuth=TraefikMiddlewareSpecForwardAuth(
+                    address=f"http://{self.name}:4180/akprox/auth?traefik",
+                    authResponseHeaders=[
+                        "Set-Cookie",
+                        "X-Auth-Username",
+                        "X-Forwarded-Email",
+                        "X-Forwarded-Preferred-Username",
+                        "X-Forwarded-User",
+                    ],
+                    trustForwardHeader=True,
+                )
+            ),
+        )
+
+    def create(self, reference: TraefikMiddleware):
+        return self.api.create_namespaced_custom_object(
+            group=CRD_GROUP,
+            version=CRD_VERSION,
+            plural=CRD_PLURAL,
+            namespace=self.namespace,
+            body=asdict(reference),
+            field_manager=FIELD_MANAGER,
+        )
+
+    def delete(self, reference: TraefikMiddleware):
+        return self.api.delete_namespaced_custom_object(
+            group=CRD_GROUP,
+            version=CRD_VERSION,
+            namespace=self.namespace,
+            plural=CRD_PLURAL,
+            name=self.name,
+        )
+
+    def retrieve(self) -> TraefikMiddleware:
+        return from_dict(
+            TraefikMiddleware,
+            self.api.get_namespaced_custom_object(
+                group=CRD_GROUP,
+                version=CRD_VERSION,
+                namespace=self.namespace,
+                plural=CRD_PLURAL,
+                name=self.name,
+            ),
+        )
+
+    def update(self, current: TraefikMiddleware, reference: TraefikMiddleware):
+        return self.api.patch_namespaced_custom_object(
+            group=CRD_GROUP,
+            version=CRD_VERSION,
+            namespace=self.namespace,
+            plural=CRD_PLURAL,
+            name=self.name,
+            body=asdict(reference),
+            field_manager=FIELD_MANAGER,
+        )
diff --git a/authentik/providers/proxy/controllers/kubernetes.py b/authentik/providers/proxy/controllers/kubernetes.py
index 3fcc55919..0d4986a4b 100644
--- a/authentik/providers/proxy/controllers/kubernetes.py
+++ b/authentik/providers/proxy/controllers/kubernetes.py
@@ -3,6 +3,9 @@ from authentik.outposts.controllers.base import DeploymentPort
 from authentik.outposts.controllers.kubernetes import KubernetesController
 from authentik.outposts.models import KubernetesServiceConnection, Outpost
 from authentik.providers.proxy.controllers.k8s.ingress import IngressReconciler
+from authentik.providers.proxy.controllers.k8s.traefik import (
+    TraefikMiddlewareReconciler,
+)
 
 
 class ProxyKubernetesController(KubernetesController):
@@ -15,4 +18,6 @@ class ProxyKubernetesController(KubernetesController):
             DeploymentPort(4443, "https", "tcp"),
         ]
         self.reconcilers["ingress"] = IngressReconciler
+        self.reconcilers["traefik_middleware"] = TraefikMiddlewareReconciler
         self.reconcile_order.append("ingress")
+        self.reconcile_order.append("traefik_middleware")
diff --git a/swagger.yaml b/swagger.yaml
index e20bf0177..aa676bfa8 100755
--- a/swagger.yaml
+++ b/swagger.yaml
@@ -10658,8 +10658,6 @@ paths:
           description: ''
           schema:
             $ref: '#/definitions/RedirectChallenge'
-        '404':
-          description: Token not found
         '400':
           description: Invalid input.
           schema: