So I tried it with Tor running on a separate machine and listening for Socks connections on its public IP. I confirmed that the SocksPort was working by pointing my web browser and it and getting an exit node on the other end. However, when I pointed OpenVPN at it, I got this error: socks_handshake: server asked for username/login auth but we were not provided any credentials It thinks that Tor is asking for a user/pass. Still investigating.