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Exchange 2010 - Delivery is delayed to these recipients or groups

solvers
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Last Modified: 2013-04-03
Hi folks,

I've got a 2 month old SBS 2011 box, and I've got a small, infrequent problem with Exchange. I've got a user account, lets say user1@domain.com, that forwards on to user1's external e-mail account via a mail enabled contact. When user2@domain.com sends user1@domain.com an e-mail, the e-mail arrives at user1's external e-mail address OK. However, the sender (user2) sometimes receives the following notification after a few hours:


Delivery is delayed to these recipients or groups:

user1@domain.com
 
Subject: Test ....
 
This message hasn't been delivered yet. Delivery will continue to be attempted.


If I log into user2's OWA and look at the delivery report for that e-mail, I can see the following:


Delivery Report for user1 ¿(user1@domain.com)¿
Submitted
02/11/2011 16:45
The message was submitted.
Pending
02/11/2011 16:45
This message was redirected to another email address.

03/11/2011 18:31
Message delivery is taking longer than expected. There may be system delays. For more information, contact your helpdesk.


If I poke through the logs I can see the e-mail was delivered to the destination pretty much immediately! If I look at the queues there isn't anything pending. What I'd expect to see instead of the above would be something along the lines of "the e-mail has left this e-mail system and can't be tracked anymore". Does anyone have any suggestions as to how I can resolve this issue? Why is Exchange telling me delivery is pending when the email has already got there!

Any help would be greatly appreciated.

Cheers,

Solvers
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Commented:
could it be that user1's external e-mail account mail system is using tar-pitting or grey-listing, therefore causing mail delays/retries from time to time.
there are plenty of information about this technologies http://en.wikipedia.org/wiki/Tarpit_(networking)
http://en.wikipedia.org/wiki/Greylisting
.
Commented:
Can you post the SMTP log for one of the messages in question, enable verbose on the send connector and under trnsport roles you will find the log directory. Also get the user to give you the message headers for a message that he has received and post this if that's ok.