Connect Mac Client to subnet behind pfSense OpenVPN server

  • I am struggling with a different OpenVPN setup than I am normally used to. I have a Mac client using Tunnelblick connecting to the OpenVPN server on my pfSense box (my network gateway and router). The Mac connects to the VPN fine, but I am still trying to figure out how to connect to a Win10 box on the network behind the pfSense box. I have done this numerous times on my OpenVPN server at work, but it is on a separate Linux server that is not on the gateway. And my work clients are all Windows boxes. I don't regularly use Macs, so working on one is relatively foreign to me. I have no idea where the Mac stored the config file. Also I am not that familiar yet with where pfSense stores the OpenVPN config file, since I set it up through the GUI. So I don't have the server and client configs handy to post, or review. I am assuming that I need to add a push route to the client config, or an iroute to the server config, but am not sure. Can someone give me some basics on where I should be looking, and what config parameter I need to read the man page on. Thanks.


  • LAYER 8 Netgate

    Put the local network in Local Networks. That will add the appropriate push route configuration.

    If you still cannot connect to a host on that local network I would check the "software" firewall on the target host.

  • Ok, I am lost on your first sentence. Is "Local Networks" something on the Mac or the pfSense config? I looked around a bit on the Mac, but like I said the Mac is very foreign to me. I was able to finally get the client config from the Mac. The only line I sanitized below is the remote line. I will check the check the firewall on the Win10 box tonight. Thanks.

    dev tun
    cipher AES-256-CBC
    auth SHA512
    resolv-retry infinite
    remote xx.yy.zz.aa 1194 udp
    setenv opt block-outside-dns
    lport 0
    push "route"
    verify-x509-name "OpenVPNServerCert" name
    pkcs12 pfgateway-UDP4-1194-MacAir.p12
    tls-auth pfgateway-UDP4-1194-MacAir-tls.key 1
    remote-cert-tls server

  • LAYER 8 Netgate

    In the OpenVPN Server configuration on pfSense.

    A push route configuration on a client makes little sense.

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