Why can't I connect to a computer over an OpenVPN connection?

Question

A network topology diagram is here:

I am able to establish a tunneling connection over OpenVPN from the PC to the OpenVPN server (icon is green). When I try to ping the Server, however, I get no response. I'm not a network guy, but my suspicion is that Server's responses are being routed out to the modem.

I have tried leaving the router un-modified and that doesn't work (as expected). I have tried adding variations of the static routing table entry shown in the diagram. I've tried it with Hops set to: 1, 3, and 4 and I've tried it with Gateway set as shown as well as 192.168.1.1. Why can't I ping Server?

EDIT: First, a correction. The connection is not using the tunneling interface like I thought. It's using the TAP interface.

I did tracert's from both ends and the results are interesting. On PC, tracert 192.168.1.100 gets nothing at all. On Server, tracert 192.168.2.104 gets nothing, but tracert 10.8.0.6 (IP assigned by OpenVPN) goes into a loop between 192.168.1.102 and 192.168.1.1.

EDIT: So, this nice guide seems to say that I should be using bridging instead of routing. I think I will investigate using this setup. I am curious though, I didn't configure a static route on each machine, but I configured a static route on the gateway (the wired router) to send VPN packets (subnet 10.8.0.x) to the VPN server. Why didn't that work?

Answer 1

Check out this link that provides debugging for what appears to be the same issue.

http://openvpn.net/index.php/open-source/faq/77-server/285-everything-seems-to-be-configured-correctly-but-i-cant-ping-across-the-tunnel.html