Simon, 

Have you looked at the Mail.App logs on the user's system itself, or attempted 
to turn up the debugging level on Mail.App and have it write a log file?  It is 
(somewhat) Unix-y after all.

https://blogs.oracle.com/chienr/entry/debugging_os_x_mail_app
http://hints.macworld.com/article.php?story=2004101603285984

Those are just from a quick Google search.  They're old (2007 and 2004 
respectively), but the application itself probably has a help file when 
launched via the command line, like most other things Unix-y.  Fire up Terminal 
and go to town... it's likely the client software itself can tell you what the 
problem is (or it's perceived problem is) with your DBMail server.

--
Nate Duehr
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