diff --git a/authentik/lib/tests/test_http.py b/authentik/lib/tests/test_http.py
new file mode 100644
index 000000000..0c6399950
--- /dev/null
+++ b/authentik/lib/tests/test_http.py
@@ -0,0 +1,67 @@
+"""Test HTTP Helpers"""
+from django.test import RequestFactory, TestCase
+
+from authentik.core.models import (
+    USER_ATTRIBUTE_CAN_OVERRIDE_IP,
+    Token,
+    TokenIntents,
+    User,
+)
+from authentik.lib.utils.http import (
+    OUTPOST_REMOTE_IP_HEADER,
+    OUTPOST_TOKEN_HEADER,
+    get_client_ip,
+)
+
+
+class TestHTTP(TestCase):
+    """Test HTTP Helpers"""
+
+    def setUp(self) -> None:
+        self.user = User.objects.get(username="akadmin")
+        self.factory = RequestFactory()
+
+    def test_normal(self):
+        """Test normal request"""
+        request = self.factory.get("/")
+        self.assertEqual(get_client_ip(request), "127.0.0.1")
+
+    def test_forward_for(self):
+        """Test x-forwarded-for request"""
+        request = self.factory.get("/", HTTP_X_FORWARDED_FOR="127.0.0.2")
+        self.assertEqual(get_client_ip(request), "127.0.0.2")
+
+    def test_fake_outpost(self):
+        """Test faked IP which is overridden by an outpost"""
+        token = Token.objects.create(
+            identifier="test", user=self.user, intent=TokenIntents.INTENT_API
+        )
+        # Invalid, non-existant token
+        request = self.factory.get(
+            "/",
+            **{
+                OUTPOST_REMOTE_IP_HEADER: "1.2.3.4",
+                OUTPOST_TOKEN_HEADER: "abc",
+            },
+        )
+        self.assertEqual(get_client_ip(request), "127.0.0.1")
+        # Invalid, user doesn't have permisions
+        request = self.factory.get(
+            "/",
+            **{
+                OUTPOST_REMOTE_IP_HEADER: "1.2.3.4",
+                OUTPOST_TOKEN_HEADER: token.key,
+            },
+        )
+        self.assertEqual(get_client_ip(request), "127.0.0.1")
+        # Valid
+        self.user.attributes[USER_ATTRIBUTE_CAN_OVERRIDE_IP] = True
+        self.user.save()
+        request = self.factory.get(
+            "/",
+            **{
+                OUTPOST_REMOTE_IP_HEADER: "1.2.3.4",
+                OUTPOST_TOKEN_HEADER: token.key,
+            },
+        )
+        self.assertEqual(get_client_ip(request), "1.2.3.4")
diff --git a/authentik/lib/utils/http.py b/authentik/lib/utils/http.py
index 779b3626c..ac4b9b5dd 100644
--- a/authentik/lib/utils/http.py
+++ b/authentik/lib/utils/http.py
@@ -40,24 +40,30 @@ def _get_outpost_override_ip(request: HttpRequest) -> Optional[str]:
         or OUTPOST_TOKEN_HEADER not in request.META
     ):
         return None
+    fake_ip = request.META[OUTPOST_REMOTE_IP_HEADER]
     tokens = Token.filter_not_expired(
         key=request.META.get(OUTPOST_TOKEN_HEADER), intent=TokenIntents.INTENT_API
     )
     if not tokens.exists():
-        LOGGER.warning("Attempted remote-ip override without token")
+        LOGGER.warning("Attempted remote-ip override without token", fake_ip=fake_ip)
         return None
     user = tokens.first().user
-    if user.group_attributes().get(USER_ATTRIBUTE_CAN_OVERRIDE_IP, False):
+    if not user.group_attributes().get(USER_ATTRIBUTE_CAN_OVERRIDE_IP, False):
+        LOGGER.warning(
+            "Remote-IP override: user doesn't have permission",
+            user=user,
+            fake_ip=fake_ip,
+        )
         return None
-    return request.META[OUTPOST_REMOTE_IP_HEADER]
+    return fake_ip
 
 
 def get_client_ip(request: Optional[HttpRequest]) -> str:
     """Attempt to get the client's IP by checking common HTTP Headers.
     Returns none if no IP Could be found"""
-    if request:
-        override = _get_outpost_override_ip(request)
-        if override:
-            return override
-        return _get_client_ip_from_meta(request.META)
-    return DEFAULT_IP
+    if not request:
+        return DEFAULT_IP
+    override = _get_outpost_override_ip(request)
+    if override:
+        return override
+    return _get_client_ip_from_meta(request.META)