Here is the layout of all the pieces and how things should work. I have a site to site vpn. Site B's tunnel enpoint is 160.41.161.60. I can see that the tunnel is up by running show isakmp sa. I have a dedicated interface on the asa (tunnel0) which is hooked up to a 6506 with an ip address of 201.188.59.254. I have a server that has 2 interfaces. One of the interfaces on the server has an ip address of 201.188.59.100. This server will need to be able to ssh into 2 machines at site b which have ip addresses of 160.41.15.103 and 160.41.15.104. My problem lies in the routing at the asa to get traffic to these 2 ip addresses through the tunnel.
By default it tries to go out the outside interface which doesn't know how to get there, and I get Destination host unreachable. I have also tried the following route entries with no success.
route tunnel0 160.41.15.0 255.255.255.0 201.188.59.254
route outside 160.41.15.0 255.255.255.0 201.188.59.254
Can anybody give me some pointers on what exactly is wrong?
