Openvpn – How to set WINS server for OpenVPN running on pfSense

VPN-connected clients don't register their hostnames. Would have to statically assign them via client overrides and manually add to DNS forwarder for them to resolve.

I would use static routes rather than push routes in a s2s situation. Or depending on how complex the network is use OSPF to exchange routes. But to be honest I've never tried to push routes in a s2s situation. It may work just fine for simple setups.

For setting up s2s with openvpn on pfsense you need to do 2 things once you've configured the openvpn server/client.

1. You need to add s2s tunnel as an interface in Interfaces->Assign on each router.
2. By default the firewall is going to block all traffic on these interfaces so you'll need to add some allow all rules to those interfaces. You can apply rules as necessary once you have things working