diff --git a/tiled/server/app.py b/tiled/server/app.py
index fa870cbf6..0c3ac7a71 100644
--- a/tiled/server/app.py
+++ b/tiled/server/app.py
@@ -409,8 +409,8 @@ def override_get_settings():
         ]:
             if authentication.get(item) is not None:
                 setattr(settings, item, authentication[item])
-            if authentication.get("single_user_api_key") is not None:
-                settings.single_user_api_key_generated = False
+        if authentication.get("single_user_api_key") is not None:
+            settings.single_user_api_key_generated = False
         for item in [
             "allow_origins",
             "response_bytesize_limit",