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CecilAdminFlag for United States of America

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E-mail Delayed, Delayed, Failed... Status: 4.4.7

To make a very long story short, I have a Windows Server 2003 with Exchange 2003 SP2.  

We use Exchange internally and use also use OWA.  Also, some users have laptops for use externally with SMTP configured in Outlook.  Some E-mails sent from the SMTP configured Outlook, for example, to Yahoo! Groups get delayed, delayed, ..., and eventually fail.

However, the same user can log into OWA or have Outlook configured directly to the Exchange server on the internal network, and can send the same message to the same e-mail address, yet the message gets delivered successfully.

Has anyone seen this or know of a way to fix this?

Below are some of the delayed and failure delivery notices:

-----Original Message:  DELAY-----

From: postmaster@domain.edu [mailto:postmaster@domain.edu]
Sent: Tuesday, June 05, 2007 11:14 PM
To: user@domain.edu

Subject: Delivery Status Notification (Delay)

This is an automatically generated Delivery Status Notification.

THIS IS A WARNING MESSAGE ONLY.

YOU DO NOT NEED TO RESEND YOUR MESSAGE.

Delivery to the following recipients has been delayed.

       group@yahoogroups.com
------------------------ANOTHER DELAY----------------------------
Reporting-MTA: dns; mailserver.domain.edu
Received-From-MTA: dns;DFJ0MY11
Arrival-Date: Tue, 5 Jun 2007 11:07:40 -0400
Final-Recipient: rfc822;group@yahoogroups.com
Action: delayed
Status: 4.4.7
Will-Retry-Until: Thu, 7 Jun 2007 11:07:40 -0400
-------------------- FAILURE --------------------------------
Reporting-MTA: dns; mailserver.domain.edu
Final-Recipient: RFC822; group@yahoogroups.com
Action: failed
Status: 4.4.7

X-Supplementary-Info: <mailserver.domain.edu #4.4.7>
X-Display-Name: group@yahoogroups.com
ASKER CERTIFIED SOLUTION
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gerardo_salvador

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I worked on this problem for nearly a week non-stop.  I searched hundreds of online articles and tens of certified knowledge bases trying everything from firewall settings (MTU, SMTP filtering, etc&), to client settings (disabling local AV, reconfiguring SMTP clients), to Exchange connectors (smart hosts, use certain virtual servers), to disabling EDNS-0to name a few.  None worked.

Through a tedious process of elimination, it turns out that it was GroupShield 6.0 for Exchange causing the problem.  Our organization had a GroupShield Anti-Virus and Content Gateway Policy adding a Declaimer Text as a signature to outbound mail.  When sending e-mail via SMTP, apparently the e-mail header or something was getting changed causing certain hosts to reject these e-mails.  Then the messages would be returned to the Exchange Queue where they would retry, delay, and eventually fail.
I've been having the very same issues. I've read Ceciladmin's comments about McAfee GroupShield and was able to fix the issue.
Hello all, my problem is similar, however slightly more complicated. Emails go in and out just fine and meeting requests are good too. The problem arises only when i have to update or delete a meeting invitation already set up in Outlook calendar. Has anyone had this problem before? i get the same notification >

Could not deliver the message in the time limit specified.  Please retry or contact your administrator.
            <server.company.com #4.4.7>

This problem is only present for certain emails, the regular, Live, Gmail, Yahoo, Aol, and most other company addresses work great, only a select few bounce back like this. Any suggestions?

We're running :
Intel Xeon CPU 2.00 GHz
4 GB RAM
Windows Server 2003 Standard SP2
Kaspersky Antivirus 6.0.3.837
Uses Microsoft Exchange 2003
Kaspersky Antivirus 6.0.3.837

Each local machine is running Outlook 2003 (office 2003 suite) and is also protected by Kaspersky .
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SOCO123

mbudman - I'm having the same issue as well with it happening on changed appointments.  We are running AVG Enterprise instead of Kaspersky though.  Have you found the cause?  
SOCO

I have found this happens when there is Exchange Server on one side and Lotus notes on the other. Apparently the two systems don't like each other.

Mark