Outgoing e-mail delayed until Exchange re-boot

[ITJam]

Hi all,
We have been made aware of outgoing e-mail messages being delayed, but with no warning or indication on the ES. We had to re-boot our 2003 Exchange Server twice within 1 week of each other for unrelated reasons. After each re-boot 2 then 3 then 4 users informed us that certain e-mail in which they had sent out 1-2 weeks prior had just been received by the recipient. This was all outgoing SMTP mail. I just received an e-mail which was forwarded by upper management regarding the delay. "...it is noticed that there is always a time lag between our correspondences. Your email below was dated August 15 which I received until August 25. Could you have your IT check on this?"...we have looked at all logs,queues, etc., that we know of and cannot find anyting that stands out as a problem. Should we turn a specific Diagnostic logging service on? Other troubleshooting ideas?
(ES3K, WS3K)

 

[ITJam]

This continues even though we have not re-started the ES...

turned on logging for MSExchange Transport SMTP protocol to Medium...waiting for logs to generate...would it help if we get all the latest updates for Winserv3K and ES3K right now? Haven't updated since 4-25-08..... thanks for any help!

 

[Xemus]

The updates are a good place to start.
Have you enabled the Message Tracking Center?

http://www.msexchange.org/tutorials..._Center_or_How_to_Save_Your_A_in_a_Pinch.html

Once that's enabled, you can search for the emails by sender and see the steps that it's taken (when it arrives at the server, how it's processed, when it leaves, or errors).

http://www.closedsocket.com

 

[ITJam]

Xemus,
Thank you...we have never used the MTC...but I'll give it a try....after the updates, of course...

 

[Topkapi]

Have a look at this article

http://searchexchange.techtarget.com/tip/0,289483,sid43_gci1269925,00.html

I think this explains your problem and gives some options to resolve it

Hope that helps

 

[ITJam]

Thanks Topkapi,
Now we have a point to further our troubleshooting...
things we have done to date are:
Turned on diagnostic logging to medium for MSExchangeTransport Queueing Engine, SMTP Protocol, NDR, Authentication.
Enabled Message Tracking Center
By turning on MTC we were able to track certain messages with the help of the SMTP log which is what identified the Greylisted issue....
And after reading the article you posted (SMTP greylisting problem on Exchange Server 2003 SP2), we tried the first and simplest workaround stopping and starting the SMTP service...when that happened we got several NDR's received by users "could not deliver the message in the time limit specified. Please retry or contact your administrator. <EMAILSERVER.DOMAIN #4.4.7> These NDRs were from e-mail sent a few days ago.
Oh, I think I JUST found the hidden treasure!
MS Exchange 2003 Server SP@ bug related to greylisting...

htp://support.microsoft.com/kb/934709/en-us

So we're not the only ones...

I hope this is it...and hope it helps someone else..
Thanks again for the leads!!!

 

[ITJam]

The previous "find" lead me to this one...THIS is it...

"E-mail senders do not receive an indication that some messages have been held by Exchange Server 2003 until the SMTP service, the Microsoft Exchange Information Store service, or the Exchange server is restarted..."

http://support.microsoft.com/kb/950757/en-us