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I would like to force all connections that a specific application (transmission) uses over a OpenVPN connection.

So far, my VPN provider pushes a default route.

I know that transmission can set a "bind-address-ipv4" option. I also know that iptables can match network connections to users and e.g. route all of the transmission-user's connections over the openvpn interface.

My problem is that I'm not exactly sure which one is a cleaner approach and how to exactly do that.

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I'm not sure I understand your layout. Do you want VPN clients to route application traffic through the VPN? – SmallClanger Feb 20 '12 at 14:25
I have a homeserver with transmission and a few other applications on it and an openvpn account at a VPN provider. I would like to have ONLY transmission be routed over the OpenVPN connection, all other software can use the regular internet connection – rb2k Feb 20 '12 at 20:34
up vote 1 down vote accepted

Ok, the solution I went for:

  • I used a regular SSH connection and created a socks proxy using "-D $PORT"
  • I used Proxychains to force XBMC through the socks Proxy. That way I can use the Hulu Plugin.
  • I used Deluge instead of Transmission because Deluge supports setting a proxy and doesn't even need proxy chains
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