@wakson005 Ok turns out the issue is using alias in my openvpn server settings. Though the alias is correct it seem to not load properly when performing HA or rebooting of PFSense. Do anyone else encounter this problem?
If Server instance has this setting OpenVPN still work but encounter the issue I stated above where I have to restart the tunnel network even though it show it is connected to get the traffic and ping working again. This is after a HA failover or a reboot of pfsense.
PFSense 2.7.0 & 2.7.1
Alias:
61e514fc-8637-490e-9900-516322d46417-image.png
Setting that will fail:
1a783268-3601-4f1a-ac54-9841c2f9bc83-image.png
Setting that will work:
ef5187d5-b71c-403b-8b31-4bb23d383f42-image.png
Obvious for this case it is pointless for an alias but for 10+ subnet the alias is just more convenient. I just like to set things up for expandability when possible. Especially in a STAR OpenVPN setup