Setting up a SOCKS 5 proxy server to talk to VPN
 

My networking situation is somewhat complex.

User is on a windows box, where traffic from some applications needs to go through a VPN, but other traffic needs to go through a direct connect. Unfortunately, I've been having a hard time come up with any solution that will allow this.

So far, the closest I've gotten to have a local Ubuntu box connect to the vpn-- that's successful, and the Ubuntu box seems to be able to communicate through the VPN successfully.

I set up squid to serve as an http proxy, and that works okay, but some applications require a socks proxy instead of an http proxy.

So I installed OpenSSH on Ubuntu and Putty on the windows, thus creating a tunnel. Unfortunately, the applications that go through this route don't seem to be able to accept incoming connections.

Basically, assume the IP address given to the Ubuntu box is 11.22.33.44 . I need to have incoming connections to 11.22.33.44:8141 successfully make their way to the WINDOWS host, which is using Putty as a Socks5 proxy.

I'm not really sure what's going wrong. The windows machine is able to make outgoing connections, but can't receiving incoming connection. How do I find where in this tangled web the trouble is?

I'm not completely sure where the problem is. Right now what i'm doing is really complex:
vpn <-> ppp <-> ubuntu <-> sshtunnel <-> windows

How do I find where the problem is? How do I make sure that incoming connections received over the VPN by the ubuntu box are successfully sent through the tunnel?

--

And is there some an easier way to accomplish this goal?


I'm a relatively new linux user. I really want to start migrating to linux, but I have to confess, I'm tempted to just buy theuser a completely separate windows box, so that one can always be connected to the vpn, one can always be connected to the direct connect, and be down with it. I know that's insane-- there's gotta be some way to set this up.

Can anyone Is there any way i could do windows sending some traffic to vpn and other to direct connect?

vpn <-> windows:8141 and simulatenously:
directconnect <-> windows:http

please, please help, lest I start hurling servers across the room. :)

Solutions?
 

Hi All!

I know this post is quite old, but I have almost the same problem.

I want to route Internet traffic for Some applications through VPN and for others through default gateway.

As I understood, best solution is to use proxy (as soon as I want to differentiate routing on Application level).

Could anyone advise proxy-servers for windows/linux suatable for this problem?

Thanks!