Hi Dev Sev!
The answer to your last question is: you have to configure your firewall (the one that do the NAT behind that you are...) to do that correctly.
It's not an IIS or a ST issue, it's your firewall that need to be configured in the right way.
And of course it depends on the make and model of firewall, so you need to ask support for that specific firewall
Gabriele Maoret - Head of SysAdmins at SERSIS
Currently manages 6 SmarterMail installations (1 in the cloud for SERSIS which provides services to a few hundred third-party email domains + 5 on-premise for customers who prefer to have their mail server in-house)