VPN/Tunneling (SSH or otherwise) on Windows via HTTP proxy

Question

Situation.

                                      ...            +-- Computers
(to the internet)                     |              |
- [ router / firewall ] -- [ switch ] +- [ switch ] -+-- Computers
                               |                     | 
                           [ proxy HTTP ]            +-- Computers

We allowed:

• HTTP & HTTPS traffic through proxy to the internet
• Access between computers in the intranet

We otherwised disallowed all other port/communication.

Is there a way for windows host machines to connect outside to e.g. terminal services server (windows 7 machines) through some VPN/tunneling means short of changing the current firewall ruleset?

Please suggest user-space (i.e. no administrative right required) applications preferably user-friendly ones that allow such access. Thanks

Solution 1

SSL VPN solutions mentioned here are somehow misleading. I would, as last resort, setup OpenVPN deamon on external box (home?) and use OpenVPN client to connect, right click on tray icon of OpenVPN client and pick 'Proxy Settings' where you clearly see "HTTP Proxy" and "Socks Proxy" also auto-detect mode as default.

SSH tunnel over HTTP(S) proxy (Reverse RDP)

This is something I work on atm so anyone reading this can check it out aswell.

Solution 2

OpenVPN would probably be a very good solution for you. The web page at http://openvpn.net/index.php/open-source/335-why-openvpn.html confirms that OpenVPN is a user-space daemon:

  "...OpenVPN is written as a user-space daemon rather than a kernel module..."

It's free, open source, secure, and highly configurable. As far as "user-friendly" is concerned, the administrator helps the user get their configuration files in place after installing OpenVPN, and then it can just connect automatically for the user whenever they're online (by setting the "OpenVPN Service" service to start automatically).

Tip: I normally rename the Network Adapter from "Network Connection 2" (or whatever name/number Windows assigns to it by default) to "OpenVPN" because this makes it easier to support later.

Comments

[Hans Kilian]

I am not quite sure how I could configure OpenVPN to run through the HTTP proxy...