Does OpenVPN / pfSense require hosts to use ITSELF as gateway for OVPN to work?

  • Here is the scenario. Client has two gateways (separate pfSense boxes) and the client manually assigns the different gateways according to who should access what connection (one fast but capped the other slow but unlimited). I have VPN running on both, but I have found that if I enter on gateway1 via OpenVPN I cannot ping any device not using Gateway1 as it's default gateway.

    For instance, Server1 uses Gateway1, while Server2 uses Gateway2 for their default gateways. I can ping server 1 only if I come in through Gateway1, but I cannot ping Server2 unless I set Server2 to use Gateway1 outbound. Yet, all are on the subnet.

    I am really just hoping for validation that I am not crazy, and perhaps a simple explanation why this is the case, which I probably really simple and I will slap myself on the forehead when I hear it. I imagine it would be necessary to add a static route, but this page indicates it will be a problem if I add it since the subnet is the same on both gateways. In the end, I would really like to be able to access the entire lan via OpenVPN from either gateway regardless of the local default gateway. I have not set any specific settings on the OpenVPN other than defaults from the wizard, though if you want I can post a copy of the config files.

    Any suggestions? I have not had opportunity to setup multiple WANs yet, I would like to and if you can point me in the direction of a simple starter howto on setting that up I will start testing.

  • What about bridge: server1+server2+lan?