Routing issue with multiple OpenVPN connections

  • I am having a strange issue… I have my network running off a pfsense box. That same box is also the OpenVPN server for 2 different VPN connections going to different friends of mine. Lets say VPN1 is on for the tunnel network, VPN2 is on I have had the first one up and running fine for a while now, but I just set up the second VPN connection last night. Both are P2P Shared Key, UDP.

    My problem is with the second connection. I haven't tested the first again after this to know if it happens both ways, but when I try to ping a device over VPN2, its random if it works...some devices seem to ping fine, others fail, it was really random. After a bit of testing, we figured out what was happening, but have no idea why. The user at the other end of VPN2 turned on packet capturing and saw my pings coming from, which is the virtual address for the VPN1 gateway...not VPN2. The pings were getting to him through that gateway though. He added a route for that traffic back to me on the correct path, and now pings work fine, however that isnt really a solution, just a work around, and I'm worried it will cause other problems down the road with heavier traffic. Any ideas why traffic for VPN2 is going out over the VPN1 virtual gateway address?

  • Post a network map, your server.conf's, your routing table and firewall rules and lets take a look.

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