Two OpenVPN clients - one for specific IP and one for remainder of traffic

  • Hi all, new guy here. pfSense is an awesome piece of software and I've figured most everything I need it to do, except for this. Any help is appreciated.

    I have a FreeNAS box behind my pfSense router running Plex and Transmission, among other things. The goals I want to accomplish are very simple:

    1. Have all devices behind the pfSense router going through a VPN tunnel (Private Internet Access). I followed this tutorial and got it working no problem. Check!

    2. Forward port 32400 so Plex can be reached outside my network. This involved setting up a firewall LAN rule to route the Plex IP through the WAN gateway (instead of the VPN gateway). Plex says the port is successfully mapped so… check! (Side question though - why would "curl" within the Plex jail still show the VPN IP address if I set Plex to route through the WAN? Shouldn't it show the WAN address?)

    3. Route the IP address of the Transmission jail through a different PIA server from the one from step 1 (one that allows remote port forwarding). This is where I'm stuck. How can I have all devices tunneling through one OpenVPN client, except for a single IP, which should be tunneled through another client? I tried adding another VPN interface, setting up a LAN rule, and hoped for the best, but not only does it not work, all the devices are now showing the IP address of that VPN client that is only supposed to be assigned to Transmission. Why would that be happening? Can two OpenVPN clients run simultaneously?

    Thanks so much for any advice  :)

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