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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?

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  • It's unlikely that anyone here will be able to give you any meaningful advice. If you explained the specifics of your connection, in detail, you might get a useful response. I would suggest that you updated your question--you should probably include (at least) the types and configurations of the two VPNs. The more detailed your question, the more help you're likely to receive.
    – Ryan B. Lynch
    Mar 23, 2010 at 16:06

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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.

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  • The problem here is that host at the data center will not have a route back to the home network so responses to packets from the home network will not be returned. I would be tempted to say you can solve this by setting up NAT/MASQ on the VPN interface for the work->datacenter VPN. I am not sure you will be able to do this though on Windows XP it might partly depend on what type of vpn software you are using..
    – Zoredache
    Mar 23, 2010 at 18:21
  • Very true point. The SSH tunnel would be the best fit for this. There could be a better Windows-centric solution that might be easier to setup.
    – Rugmonster
    Mar 23, 2010 at 19:20

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