A while ago I bought multiple static IP addresses from my ISP. I configured the IPs as Virtual IP addresses through Firewall / Virtual IPs. Everything was dandy.. until I tried to assign OpenVPN to listen on one of my new IP addresses. No matter what I tried I could only get it to work if it listened on my gateway IP.. none of my other static IP addresses would work. The GUI would let me save the configuration, but if I headed over to Status / Openvpn I would see the following:
[error] Unable to contact daemon Service not running?
Digging further in the logs by going to Status / System Logs and then selecting the OpenVPN tab revealed the following snippet:
|May 15 19:42:00||openvpn||73195||Exiting due to fatal error|
|May 15 19:42:00||openvpn||73195||TCP/UDP: Socket bind failed on local address [AF_INET]<redacted>:443: Can’t assign requested address|
After 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. That did the trick!