UFW blocks OpenVPN
I have a server on my home network that has UFW enabled to allow internal clients and force all traffic over vpn. When I try to connect from a VPN client it gets blocked even though I have allowed 10.0.8.0/24 in UFW.
So I take it 10.0.8 is your tunnel network.
But you say you force this machine out some vpn (on it) to go to remote networks, which 10.0.8 would be..
Just create a route so that it knows 10.0.8 is local and to not go out its vpn to get to it.. Ie point a route on it to your pfsense IP on its network.
Or you could source nat the traffic on pfsense so this box thinks the traffic from your vpn is on its local network.