So, here is my system: I have a 2Wire AT&T modem/router which I use for wireless and a Buffalo router flashed with DD-WRT which is physically attached to the 2Wire and set in the DMZ. I set everything up on the DD-WRT to be able to connect to it using ssh and also so that it forwards ssh requests on a different port to one of the servers behind it. Now, when I am physically connected to the DD-WRT all this works great and as I would want it to. I ssh into the two different ports using the WAN IP of my network, and I get where I expect to land. If, however, I am connected using wi-fi to the 2Wire, the same commands do not work. I do not get an error, simply a timeout. I have trouble understanding this, since the DD-WRT is set in the DMZ and everything should pass to it. To further complicate the problem, I tried connecting to the same IP using my phone (wireless disabled, so really from the WAN) and surprise, it works! If I go back on the local network by enabling the wifi, the ssh connection times out. To make this even stranger, my WAN IP address always responds to pings (meaning in all the above situations). What could be going on here?

I know what I should do, completely disable the 2wire as a router and use it strictly as a modem and them use all the routing capabilities of the dd-wrt. It's what I will probably end up doing anyway, but my question remains, because I really want to know what is happening here.