Having a bit of time, and remembering that OpenVPN had an option for SOCKS proxies, I decided to take a stab at getting OpenVPN to work through a SOCKS proxy.
It was far easier than expected.I’m on a Windows 7 system, so I had to set PuTTY up to create a tunnel – under Connection > SSH > Tunnels, I added
31337 as a source port, and set it to ‘
After that, I just added the line
socks-proxy localhost 31337 to the OpenVPN config file – again, the TCP-based one, not the UDP-based one.
And that was pretty much it – hit connect in OpenVPN, and it worked.
I was pleased.