Tunneling traffic through two VPN hops/tunnels

tunnelingvpn

I am a web developer, and I find myself often working from home.

But when I do, I am forced to Remote Desktop to the Office desktop computer and work from there. The reason is because the application I am working on needs to connect to servers at a Data Center via a VPN from the Office Desktop.

HomeDesktop (Win7) —> PVN —>
OfficeDesktop(WinXP) —> VPN —>
Data Center

What I would really like to do is, I would like to find a way to be using my Home desktop developing on that, and whenever my computer tries to access servers on the Data Center, I would like to tunnel that traffic through the two VPN tunnels which are currently separating me and the Data Center.

I have admin privileges on both Office Desktop and Home Desktop, but I do not have any admin privileges in the Data Center. So what kind of tunneling solution could I use here? Is it even possible?

Best Answer

This is kind of jankety, but you could setup openvpn on your desktop at work. You would then connect the original home->work VPN and connect OpenVPN through it. You would then push a route from the work desktop to the home system so it could then route traffic appropriately directly to the server in the DC.

In the openvpn config, the route could be pushed to the home system like so:

push "route 12.34.56.78 255.255.255.255"

12.34.56.78 being the IP of the server in the DC

Alternatively, you could run an SSHD via cygwin or something on the work system and use that to tunnel the RDP connection through.