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So, in case you're connected to a VPN, how do you make a particular process (say, a browser or an instant messanger) "proxy" through the VPN instead of going directly through the default network adapter on Windows?

Hope this was clear enough; thanks.

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migrated from Nov 22 '11 at 22:17

This question came from our site for system and network administrators.

up vote 2 down vote accepted

I think is not possible due the routing policies doesnt permit use apps or ports.

You have two options:

  1. Tell the applications that use a proxy, and create a proxy who use that VPN.
  2. If you know to which ip address is communication your software (you can discover that using the command netstat -ano and discover if that addresses are static, if they are you can) you can modify the rounting table using the command route add -p to tell the PC that every traffic send to that IP goes to the VPN gateway.
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#2 here is more or less your best bet n2liquid, Ricardo hit what I was going to say on the nail. – TrueDuality Oct 17 '11 at 19:13

You can't. You can only route via the VPN, and the routing table won't have any regard for what protocol or program is sending the packet. The routing policy is usually dictated by the VPN endpoint. If you have a proxy of some sort at the remote end of the VPN you can point your browser or instant messenger at, then you're in business - all you have to do is route the address of the proxy via the VPN.

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I'm not aware of any vpn clients (windows 7 included) that allow you to set this on a per process basis. It's usually all or nothing.

In the case of Windows VPN, you can only tell it whether to "use default gateway on remote network" or not.

Additionally, you're at the mercy of your VPN administrator on whether or not traffic is proxied through the VPN, if you use a client.

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The closest way I can think of to achieve the result is to install an HTTP Proxy or SOCKS on the OpenVPN server (or any other host reachable over it) and configure each single application to use it (not using system-wide proxy settings).

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In know you can achieve this with SOCKS using proxifier

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