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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

      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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      • DerelictD
        Derelict LAYER 8 Netgate
        last edited by Derelict

        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

          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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          • DerelictD
            Derelict LAYER 8 Netgate
            last edited by Derelict

            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)

            1 Reply Last reply Reply Quote 0
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