diff --git a/roles/matrix-nginx-proxy/tasks/self_check_well_known.yml b/roles/matrix-nginx-proxy/tasks/self_check_well_known.yml
index d12e3fd3..2ea110bf 100644
--- a/roles/matrix-nginx-proxy/tasks/self_check_well_known.yml
+++ b/roles/matrix-nginx-proxy/tasks/self_check_well_known.yml
@@ -6,6 +6,7 @@
       - path: /.well-known/matrix/client
         purpose: Client Discovery
         cors: true
+        follow_redirects: false
 
 - block:
     - set_fact:
@@ -13,6 +14,7 @@
           path: /.well-known/matrix/server
           purpose: Server Discovery
           cors: false
+          follow_redirects: true
 
     - name: Determine domains that we require certificates for (mxisd)
       set_fact:
diff --git a/roles/matrix-nginx-proxy/tasks/self_check_well_known_file.yml b/roles/matrix-nginx-proxy/tasks/self_check_well_known_file.yml
index 40161807..40fa95a6 100644
--- a/roles/matrix-nginx-proxy/tasks/self_check_well_known_file.yml
+++ b/roles/matrix-nginx-proxy/tasks/self_check_well_known_file.yml
@@ -35,7 +35,7 @@
 - name: Check .well-known on the identity hostname
   uri:
     url: "{{ well_known_url_identity }}"
-    follow_redirects: false
+    follow_redirects: "{{ well_known_file_check.follow_redirects }}"
     return_content: true
   register: result_well_known_identity
   ignore_errors: true