A health care provider I work with has attempted to create the ability for
people like me (who provide medical care for our patients in their
facilities) to correspond with medical care professionals in the company in
a HIPAA-compliant manner. Basically this involved creating IMAP email
accounts for each of us external users that connect to their Exchange 2007
Server using SSL and (I think) custom, non-standard ports). I've followed
their instructions to configure setup on each of my Macs, my iPhone, several
Fusion VM PCs running XP and Windows 7, and one "real" Windows Vista Home
Premium Dell box.

On the iPhone, the IMAP folders populated themselves the first time I
connected to the server, and sending and receiving mail works without a
hitch.

On the Mac, the first time I try to send a message after launching Entourage
(2008 EWS, fully updated), I'm greeted by a dialog that says the message
will be encrypted but not secure (what does that MEAN, by the way), but if I
click the button to send it, it transmits; second and subsequent messages
(as long as I don't quit Entourage) don't prompt this message.

In Windows (Office Outlook 2007), if I create a message and click "send" it
just sits in my outbox forever. However, the IMAP mail folders populate
completely.

So, there must be some glitch regarding my communication with their sendmail
server. I've talked with their IT people about it; I don't think they've
actually tested this from outside their own intranet; it's just their belief
that it SHOULD work -- but it doesn't. I've Googled the problem and checked
to make certain I have the right certificates in the right places in my
keychain, and everything seems to be OK there.

Does this ring bells for anyone here? Any suggestions what I should try
next?

Jim Robertson
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