diff --git a/authentik/core/api/utils.py b/authentik/core/api/utils.py
index f768bb812..87aa87260 100644
--- a/authentik/core/api/utils.py
+++ b/authentik/core/api/utils.py
@@ -14,7 +14,9 @@ def is_dict(value: Any):
     """Ensure a value is a dictionary, useful for JSONFields"""
     if isinstance(value, dict):
         return
-    raise ValidationError("Value must be a dictionary, and not have any duplicate keys.")
+    raise ValidationError(
+        "Value must be a dictionary, and not have any duplicate keys."
+    )
 
 
 class PassiveSerializer(Serializer):
diff --git a/authentik/outposts/api/outposts.py b/authentik/outposts/api/outposts.py
index 7e6972171..41cb8b0a4 100644
--- a/authentik/outposts/api/outposts.py
+++ b/authentik/outposts/api/outposts.py
@@ -51,7 +51,7 @@ class OutpostSerializer(ModelSerializer):
                 raise ValidationError(
                     (
                         f"Outpost type {self.initial_data['type']} can't be used with "
-                        f"{provider.__class__.__name} providers."
+                        f"{provider.__class__.__name__} providers."
                     )
                 )
         return providers
diff --git a/authentik/outposts/controllers/docker.py b/authentik/outposts/controllers/docker.py
index 53231f823..5f0d71d94 100644
--- a/authentik/outposts/controllers/docker.py
+++ b/authentik/outposts/controllers/docker.py
@@ -36,8 +36,10 @@ class DockerController(BaseController):
 
     def _get_env(self) -> dict[str, str]:
         return {
-            "AUTHENTIK_HOST": self.outpost.config.authentik_host,
-            "AUTHENTIK_INSECURE": str(self.outpost.config.authentik_host_insecure),
+            "AUTHENTIK_HOST": self.outpost.config.authentik_host.lower(),
+            "AUTHENTIK_INSECURE": str(
+                self.outpost.config.authentik_host_insecure
+            ).lower(),
             "AUTHENTIK_TOKEN": self.outpost.token.key,
         }
 
@@ -45,11 +47,10 @@ class DockerController(BaseController):
         """Check if container's env is equal to what we would set. Return true if container needs
         to be rebuilt."""
         should_be = self._get_env()
-        container_env = container.attrs.get("Config", {}).get("Env", {})
+        container_env = container.attrs.get("Config", {}).get("Env", [])
         for key, expected_value in should_be.items():
-            if key not in container_env:
-                continue
-            if container_env[key] != expected_value:
+            entry = f"{key.upper()}={expected_value}"
+            if entry not in container_env:
                 return True
         return False
 
diff --git a/website/docs/releases/v2021.6.md b/website/docs/releases/v2021.6.md
index fae4006ca..fe3b0c89b 100644
--- a/website/docs/releases/v2021.6.md
+++ b/website/docs/releases/v2021.6.md
@@ -143,6 +143,9 @@ slug: "2021.6"
 
 - crypto: show both sha1 and sha256 fingerprints
 - flows: handle old cached flow plans better
+- g: fix static and media caching not working properly
+- outposts: fix container not being started after creation
+- outposts: fix docker controller not checking env correctly
 - outposts/ldap: add support for boolean fields in ldap
 - outposts/proxy: always redirect to session-end interface on sign_out
 - providers/oauth2: add revoked field, create suspicious event when previous token is used