OpenVPN Multi Site2Site - 1 Connection missing routing table entry for local net



  • Well,  I've setup a multi-site to site OpenVPN server that works fine with Tomato clients.  But, I'm looking to change out one of the clients to a pfsense router and after trying a slew of different options I still am unable to route to the remote clients local net.

    A rough network layout

    Comstar (PFSense OpenVPN Server) [Local Net - 192.168.10.1/24 - VPN Net - 172.29.160.1/19]

    • Kenai (Tomato OpenVPN Client) [Local Net - 192.168.13.1/24 - VPN Net - 172.29.160.4/19]
    • Banana (Tomato OpenVPN Client) [Local Net - 192.168.11.1/24 - VPN Net - 172.29.160.2/19]
    • Cavendish (PFSense OpenVPN Client) [Local Net - 192.168.14.1/24 - VPN Net - 172.29.160.3/19]  << Unable to route to this subnet

    Peer to Peer (SLS/TLS)

    Currently all of the tomato clients work fine.  I can ping and connect to all of the following subnets (192.168.10.0/24, 192.168.11.0/24, 192.168.13.0/24)

    But the new PFSense client on the 192.168.14.0/24 subnet does successfully connect to the OpenVPN server.
    But I am unable to route traffic over to the 192.168.14.0/24 subnet.

    I think it has something to do with a missing entry in the routing table.
    I can see that connection for Cavendish on 172.29.160.3 but, it does not appear to have a matching entry for the remote subnet 192.168.14.0/24

    Not sure what might be causing this.  Especially since, all of the other clients (Tomato) based seem to be working fine.  I've attached the output of my routing table output.

    Anybody have an idea of what I'm missing?

    Thanks,
    dc