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Old 10-27-2007, 12:16 AM   #1
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Registered: Oct 2007
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Angry 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 . I need to have incoming connections to 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.
Old 05-04-2010, 04:17 AM   #2
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Registered: May 2010
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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?



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