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Connect Mac Client to subnet behind pfSense OpenVPN server

Scheduled Pinned Locked Moved OpenVPN
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  • J
    jeffboyce
    last edited by Nov 20, 2018, 7:31 PM

    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.

    Jeff

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    • D
      Derelict LAYER 8 Netgate
      last edited by Derelict Nov 20, 2018, 7:40 PM Nov 20, 2018, 7:40 PM

      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.

      Chattanooga, Tennessee, USA
      A comprehensive network diagram is worth 10,000 words and 15 conference calls.
      DO NOT set a source address/port in a port forward or firewall rule unless you KNOW you need it!
      Do Not Chat For Help! NO_WAN_EGRESS(TM)

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      • J
        jeffboyce
        last edited by Nov 20, 2018, 10:05 PM

        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
        persist-tun
        persist-key
        cipher AES-256-CBC
        auth SHA512
        tls-client
        client
        resolv-retry infinite
        remote xx.yy.zz.aa 1194 udp
        setenv opt block-outside-dns
        lport 0
        push "route 10.8.6.0 255.255.255.255.0"
        verify-x509-name "OpenVPNServerCert" name
        auth-user-pass
        pkcs12 pfgateway-UDP4-1194-MacAir.p12
        tls-auth pfgateway-UDP4-1194-MacAir-tls.key 1
        remote-cert-tls server

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        • D
          Derelict LAYER 8 Netgate
          last edited by Derelict Nov 21, 2018, 1:18 AM Nov 21, 2018, 1:18 AM

          In the OpenVPN Server configuration on pfSense.

          A push route configuration on a client makes little sense.

          Chattanooga, Tennessee, USA
          A comprehensive network diagram is worth 10,000 words and 15 conference calls.
          DO NOT set a source address/port in a port forward or firewall rule unless you KNOW you need it!
          Do Not Chat For Help! NO_WAN_EGRESS(TM)

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