Duplicate messages with Outlook and Exchange 2003

Posted on 2007-10-12
Medium Priority
Last Modified: 2008-07-17
For the past couple months some of my users have been complaining of a somewhat odd e-mail issue. The problem manifests as multiple duplicate e-mails from a single, known sender.

The characteristics of the duplicate messages are as follows:

Same message ID
Identical header information, aside from timestamp on the last hop
Sometimes with attachments, sometimes without
Usually sent to a number of people, generally >5
Messages arrive in ~1 hour intervals

A simple diagram of our network looks as follows:

1) Trusted: Users
2) Trusted: Exchange 2003
3) DMZ: GFI MailSecurity / MailEssentials in SMTP Gateway mode
4) Cisco PIX-525
5) Internet

The timestamp discrepancy occurs between numbers 3 and 4.

If you would like to punish your eyes, you can view the Exchange Message Tracking information for the MessageID in question at this link: http://www.clarionlogic.com/tracking.xml

There doesn't seem to be any real pattern as to when this happens or to whom. We use Symantec AntiVirus on the Exchange server, with all the necessary files/processes excluded from scanning. There doesn't seem to be anything 'stuck' in either the Exchange or GFI server mail queues.

Any help will be greatly appreciated. If you need further information, please ask and I will do my best to provide it.
Question by:CharlesWalton
  • 2
LVL 104

Expert Comment

ID: 20069297
The Cisco device shouldn't be in the headers.
Do you have fixup smtp turned off on the PIX?

It sounds like the duplication is taking place on the last step because the sending server doesn't know the message has been delivered correctly. The PIX with fixup SMTP is notorious for this.


If your question has been answered, please remember to accept the answer and close the question.

Author Comment

ID: 20071124
The PIX isn't in the header, I included it in the list just for reference.
I believe that fixup SMTP is turned on - I'll check and post again.

Author Comment

ID: 20123822
Rebooting seems to have corrected the issue.

Accepted Solution

Computer101 earned 0 total points
ID: 22032286
PAQed with points refunded (500)

EE Admin

Featured Post

Efficient way to get backups off site to Azure

This user guide provides instructions on how to deploy and configure both a StoneFly Scale Out NAS Enterprise Cloud Drive virtual machine and Veeam Cloud Connect in the Microsoft Azure Cloud.

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

How to effectively resolve the number one email related issue received by helpdesks.
Steps to fix “Unable to mount database. (hr=0x80004005, ec=1108)”.
This video discusses moving either the default database or any database to a new volume.
Exchange organizations may use the Journaling Agent of the Transport Service to archive messages going through Exchange. However, if the Transport Service is integrated with some email content management application (such as an antispam), the admini…
Suggested Courses
Course of the Month14 days, 21 hours left to enroll

840 members asked questions and received personalized solutions in the past 7 days.

Join the community of 500,000 technology professionals and ask your questions.

Join & Ask a Question