Proxy requests through VPN connection

Sound like it would work but for me is not a possibility because the issuer wont reissue it. Is there a way to mask the IP or perhaps is something to do with routing configs.

How can i possibly achieve this without reissuing the certificate? Also it there a way to debug the connection , because i feel there must be more information i can check apart from the dashboard log error i posted.

Would this work ro be related to this challenge