It was an SSL connection with a custom cert chain. So I could easily wrap the HTTP side of things with a SOCKS forwarder which then SOCKS proxied into the VPN

It was an SSL connection with a custom cert chain. So I could easily wrap the HTTP side of things with a SOCKS forwarder which then SOCKS proxied into the VPN and then back out to the other site. There might have been another way to do it, but given that wrapping HTTP in a SOCKS proxy is easy and ssh has a built in SOCKS proxy, this was quick win. ps. It's SOCKS and not Socks - for the subject line of this story.