Mail Going missing after SMTP Queue - Exchange 2003

A client just called and is complaining that mail from a single sender is no longer being delivered.

I go into the SMTP logs, and see the (woefully inadequate) 4 lines showing me the inbound email came in from our outside filtering company.

If I go to message tracking, there's no record of the message every arriving.

Any ideas?
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Simon Butler (Sembee)ConsultantCommented:
If the email isn't in Message Tracking, then it didn't hit Exchange.
Primary cause of this, particularly if they are in the SMTP logs is AV software scanning something it shouldn't be.
The SMTP logs don't show much, as there isn't much to log - connect, transfer, disconnect - that is about it.

Sadly I find the log file somewhat lacking in detail. For these situations, I turn on Wireshark, send/recieve the email and read the full conversation. It will provide you with all the answers you need.
jephensAuthor Commented:
If the email isn't in Message Tracking, then it didn't hit Exchange.

So when does the SMTP server hand it off to Exchange?  I thought the SMTP server was a part of Exchange?  Not in 2003, maybe?  (It's been a while...)
Simon Butler (Sembee)ConsultantCommented:
Exchange 2003 SMTP is provided by the IIS service. Exchange kind of takes over, but the core code is IIS. Therefore there are two steps to the traffic and it is perfectly possible for the email to get blocked at the first step if AV isn't configured correctly for example.

Often I find that restarting the server will allow some of the missing email to come back because the hold the AV software has on it is released.


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jephensAuthor Commented:
This client had a spam filter I wasn't aware about running.  The mail was getting killed from there.
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