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One of the recipients missing in message tracking (didn't receive the mail), visible in email history

Posted on 2014-02-17
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Last Modified: 2014-06-24
Environment:
(a single) local Exchange 2010 installation on Windows Server 2008 R2
AV: GFI MailEssentials 2012

Problem:
A user today complained about not having received an email. I've replaced the addresses but you get the picture. The only reason we caught this one is b/c there was a second recipient inside our organization who did receive the mail.
email history
The user is part of the "office" mailing list. I checked the message tracking and indeed, the mailing list is missing and none of the users in that list received the mail. Only the second recipient, a single user, received it and can be found in the tracking:
message tracking
If the recipients would be missing altogether ok, but can someone riddle me how one recipient is visible in the Outlook email history of our user but not in our message tracking?
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Question by:sysadmin84
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Expert Comment

by:Simon Butler (Sembee)
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If the message isn't in tracking, then the message wasn't received by Exchange.
That would point the problem at being outside of Exchange. The sender MTA must have sent two different messages, so Exchange handled the one it got as for just that recipient, the second copy (sent to the distribution list email address) wasn't received or was rejected at point of delivery.

Simon.
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by:sysadmin84
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Maybe I'm misunderstanding your explanation but if there are in fact two messages (one with 2 recipients that never reached our Exchange and one with 1 recipient) then why would the two recipients show up in our email history (see first screen cap in the original post). The time-stamp fits with the tracking.
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Simon Butler (Sembee) earned 500 total points
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Header information is just that, header. It is just text. It means that when the message was generated by the remote MTA, that the sender put both addresses in.
I would go as far as to say that header information cannot be relied upon, it is easily faked and is not a true representation of who may have received the email. You don't see BCC information in the header, nor do you see any forwarding that might go on.

Message Tracking is the only thing that you can relay on, the message doesn't appear there, so it never arrived.

Simon.
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Author Comment

by:sysadmin84
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Unfortunately, this is now not an isolated incident anymore, so the problem seems to lie with a misconfiguration on our end. The same thing happened with a different sender. This time, the tracking again only shows one of the recipients (and that one with a different TLD than in the header, we use both .de and .eu though).

Header shows: john@contoso.eu; office@contoso.eu

and here's the tracking (john@contoso.eu is a distribution list with only the user jsmith@contoso.eu in it):
message trackingAny pointers on where to start with the troubleshooting?
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Author Comment

by:sysadmin84
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Update: So we had another case of this and this time I had the common sense to go into the mailbox and check the header itself. Turns out that the sender had a faulty autocomplete-entry (typically caused by Outlook falsely identifying a mailto: - link). Too bad the senders didn't contact their IT department or us about it since this produces an NDR.
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