I have setup a router behind a router for security purposes. All hosts have their own Static DHCP entries and DNS resolution for Statis DHCP hostnames works from any host within the same subnet as the host and router's LAN IP. However, DNS resolution does not work for hosts in another subnet even though you would think it should work (at least to me). For example. I have the first router subnet as 192.168.2/24 and a second router's WAN is member to that subnet, and the second router's LAN subnet is 192.168.3/24. Any client on 192.168.3/24 cannot resolve Statis DCHP entries on 192.168.2/24. Since this didn't work out of the box I added a dnsmasq entry on the 192.168.3/24 router for the 192.168.2/24 hosts. This also did not work. I can ping the hosts fine so routing works. I just can't get the hostnames into DNS. I really thought this would be all automatic since Tomato and just about all routers these days are setup as caching DNS servers.
I this doesn't make sense I will draw a picture.