That is, I have set my openvpn client configuration to be "remote localhost port" where port is the port my stunnel client is listening on the same box as my openvpn client.

This seems to work - I get connected to OpenVPN server fine, however, I don't seem to be able to ping the openvpn server by either of it's public or private ip addresses. In fact, it seems like when I do a tcpdump on the stunnel server, I don't see any incoming traffic on port 443. How is it possible that I am getting the VPN connection, but then the rest of the traffic just sort of stops going through stunnel?

My stunnel client service looks like the following:

[openvpn]
accept = 127.0.0.1:5150
connect = stunnelserver:443