If you haven’t already, generate a certificate authority and server certificate. I used the following settings to get things working between these two devices: OpenVPN Server (pfSense) Firewalls need to be configured to allow traffic to/from each network through the VPN tunnel.Routes for each network need to be established on both devices.VPN IP addresses need to be assigned to both the server and the client.Protocol, port, device type, encryption cipher, hash algorithm, TLS authentication, and certificate settings all need to match.In order to get this to work you need to keep these things in consideration: It was quite the undertaking for me to get these two systems talking. No longer! I’ve finally gotten a site to site VPN working between my pfSense router and my parents’ Netgear Nighthawk R8000 running DD-WRT v3. Each time I try I become frustrated and eventually give up. I’ve been trying to establish a site-to-site VPN connection between my house and my parents’ for a couple years now. That did the trick! openvpn pfSense SSL VPN VIP TCP/UDP: Socket bind failed on local address :443: Can’t assign requested addressĪfter much digging I finally stumbled upon this post in the pfsense threads. In it they mention that in the Firewall / Virtual IPs screen not to bind (in the interface option) your IP addresses to the WAN interface, but rather to bind them to localhost. The GUI would let me save the configuration, but if I headed over to Status / Openvpn I would see the following: Unable to contact daemon Service not running?ĭigging further in the logs by going to Status / System Logs and then selecting the OpenVPN tab revealed the following snippet: Time none of my other static IP addresses would work. No matter what I tried I could only get it to work if it listened on my gateway IP. until I tried to assign OpenVPN to listen on one of my new IP addresses. I configured the IPs as Virtual IP addresses through Firewall / Virtual IPs. A while ago I bought multiple static IP addresses from my ISP.