Let pfsense route internal connection to different vpns/no vpn

  • First of all my apologies for hurting your eyes with this badly made ms paint image (don't have access to anything else at the moment).

    I have an internal network with two clients: a workstation windows pc and a ubuntu fileserver. I have an openvpn provider that only allows 1 connection at a time. On the windows pc I would sometimes like to be connected through my vpn provider and sometimes not. On the server I run downloads that I would always like to be connected through the vpn provider. I also have a second fileserver in a remote location that I would like the first fileserver to backup to over a site to site vpn connection.

    Is it possible to make pfsense route these different kinds of traffic to different vpn connections? Is there a way to switch in between normal internet and vpn through pfsense from the windows client?

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