Hello Nikola, Port 3389 would be irrelevant for the Windows Proxy, only port 445 needs to be open. Per
KB 209957 you also need to make sure that SMB2 communication is allowed by the target server. You may need to check Windows event logs on the target server for other errors while the Windows Proxy is trying to verify or update the target account. If you are using a service account for the update, make sure that account has the required privileges on the target server.