Gateway Down OpenVPN Connection

I have an OpenVPN connection with a friend. Both of us have pfsense. The OpenVPN connection works fine on my phone and Mac.

I’ve configured the connection on my pfsense box. I get a local IP underneath interfaces and the openvpn connection says it’s up at my friends IP address along with the local openvpn IP address. On the remote end, I show as connected as well. However, the gateway shows as down on my end.

How do I troubleshoot?

The gateway is determined up or down based on ping. Make sure the rules allow for ping and access. Start by putting in an allow all rule, if that works back it down to the restriction level needed.

I found the problem, but don’t know how to resolve it. I have OpenVPN connections to two friends houses, both with different OpenVPN IP ranges:

Friend 1 - 192.168.33.1
Friend 2 - 192.168.110.1

When both are connected, both gateways resolve to Friend 1’s router when I type the gateway IPs in the browser and Friend 2’s gateway show as down.

When I remove Friend 1’s OpenVPN connection, I can hit friend 2’s router and the Gateway shows as up.

I hope this makes sense, but there seems to be some type of conflict, however, I don’t know where as both have separate IP ranges and certificates.

Not only the OpenVPN networks should not overlap, but neither should any internal networks from each site.

That’s it. Confirmed that friend 1 is using a vlan on the 110.0/24 range. Thank you.