Quick summery of what im trying to accomplish Im testing a Netgate pfSense router at home and wish to connect it behind my Shibby Tomato router as not to disrupt my normal home network set up. The VPN will be connected to my corporate location. I have configured the tunnel and have it working if the pfSense router is the gateway. The issue I have now is when I put the pfSense router behind my home tomato router, the VPN on both ends shows connected but I cannot ping the corporate network from the workstation at home I have connected to the pfSense router likewise from corporate to the pfSense subnet. Overview of network Motorola DOCSIS 3.0 Modem (192.168.100.1) Router 1 "Gateway" (192.168.0.1) Shibby Tomato Firmware 1.28.0000 MIPSR2-115 K26 USB Big-VPN Static Route to pfSense router Destination Gateway / Next Hop Subnet Mask Metric Interface 10.0.9.0 192.168.0.4 255.255.255.0 0 br0 (LAN) I have also put 192.168.0.4 in a DMZ in hope to open op all ports to the pfSense router NAT is set to ALL > MASQUERADE DHCP for the 192.168.0.0 network and DNS is handled by my Windows server for the devices in my home. Router 2 "pfSense" (LAN 10.0.9.254) WAN IP 192.168.0.4 DHCP scope 10.0.9.10 - 10.0.9.245 1 Workstation connected to the LAN (10.0.9.11) VPN to corporate shows a connection in pfSense on both ends but can not assess or ping either way Corporate is fine as it the other locations currently have a working VPN and I connect fine when the pfSense router is the gateway. Firewall has been opened to allow ANY connection on the WAN So now im suck. I thought the static route would allow packets through to the pfSense router but no luck. Im thinking its a NAT issue but im not sure. Any help would be appreciated. Thanks.