> Just needed a rant, been ages since i last had one!
I know the feeling.

And I understand the purpose of your post, but since I find it to be interesting I'm still replying
What is required from the user interface for beginners to understand it quickly? I can't really merge the entire documentation into the user interface - and even if I did, the people who ignore the docs today would probably ignore the hints there as well.
One idea I had was to create more "step-by-step" documentation. "Setting up hMailServer to do spam protection in front of Exchange", "Setting up hMailServer in two separate offices" and so on. At least then we could point the users to this documentation.
I've also thought about adding some self-tests to hMailServer, to the status section. You would select the domain you were having problems with and then hMailServer would check the MX records for this domain. hMailServer could connect to mail.hmailserver.com:25 to confirm that this is possible. Also, it could connect to a PHP script on hMailServer.com, which would connect
back to the hMailServer instance. This way hMailServer could confirm that both incoming and outgoing ports were open.
Another thing is an "Test"-button next to every place where you enter a hostname:port setting. This would allow the user to confirm that it's at least possible to connect to the host without sending an email message. In the external account settings the "Test" button could confirm that it was possible to log on using the entered credentials.
In your opinion, which is the most frequent user problem?