@jared_ said in Need help routing OpenVPN to another gateway on the LAN:
I have pfSense sitting on a network, the WAN interface is disabled and the LAN (192.168.1.0/24) has OpenVPN (172.16.100.0/24) server listening.
That's not the proper way to connect a VPN server. Youf LAN devices will send response packets to requests from VPN clients to the default gateway instead back to pfSense, since they don't have a proper route for these IPs.
If you want to run the VPN server behind a NAT router either
remove it from LAN and put it into transit network, connected to the router and add a static route for the VPN tunnel network to the router pointing to the VPN server and add static route for the LAN to the VPN server pointing to the router add a static route for the VPN tunnel network pointing to pfSense to each LAN device you want to have access do masquerading on pfSense Lan interface.