Loopback is generally refered to when you access an IP/port on the same machine you are working on. The loopback address is 127.0.0.1 aka localhost on most machines.
If you are accessing your server with an external IP then the default route will take you out past your gateway to at least one more router and back to your firewall ( unless your gateway has an interface with an IP in the same subnet as your servers external IP).
If you have the server NAT'd behind m0n0wall, you will need to use Proxy ARP and open the firewall to let the correct IP/ports through.
Cheers, Dan
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