Solved

Dulplicate outgoing email from Mac, MS Exchange 2003

Posted on 2012-03-30
7
580 Views
Last Modified: 2012-04-02
I have one employee who uses Mac mail client on his laptop connected to our exchange server 2003.

When he sends an email to a group, 3 recipients(two domains) receive duplicate emails every 10 minutes or similar interval. I checked Queue in Exchange server, the email bounded to the two persons were stuck and shows as 'Active' and '28 times failed'. But the recipients say they already received the same email multiple times.

Right now, I froze the outgoing email in queue so I can take a look at it more. I'm not sure if this is their domain email server problem or our email server or the Mac mail client. There seems some mail exchange communication problem between any of three.

To troubleshoot, what should I look at?
0
Comment
Question by:crcsupport
  • 4
  • 3
7 Comments
 
LVL 10

Assisted Solution

by:pclinuxguru
pclinuxguru earned 500 total points
ID: 37787607
So when he sent the email it keeps resending the same email over and over or do they receive the same email twice?
0
 
LVL 1

Author Comment

by:crcsupport
ID: 37787658
I looked at the email log, the email was recorded as it was sent out once, but the email was still on queue as 'Active' and it shows 28 times failed. And the recipient received more than 20 times. I guess the email reached the recipient email server, but my email server some how it thinks the recipient server didn't receive, some miscommunication between the two servers.
0
 
LVL 1

Author Comment

by:crcsupport
ID: 37787660
I still have the email frozen in queue, need to troubleshoot this. This happened a few times before recently.
0
Maximize Your Threat Intelligence Reporting

Reporting is one of the most important and least talked about aspects of a world-class threat intelligence program. Here’s how to do it right.

 
LVL 1

Author Comment

by:crcsupport
ID: 37787702
The delayed notification sent to the sender.


Reporting-MTA: dns;mail.xxxxxx.com
Received-From-MTA: dns;[10.0.1.4]
Arrival-Date: Thu, 29 Mar 2012 23:42:48 -0400

Final-Recipient: rfc822;ccc@yyyyyyyyy.com
Action: delayed
Status: 4.4.7
Will-Retry-Until: Sat, 31 Mar 2012 23:42:48 -0400

Final-Recipient: rfc822;vvvv@yyyyyyyyyy.com
Action: delayed
Status: 4.4.7
Will-Retry-Until: Sat, 31 Mar 2012 23:42:48 -0400
0
 
LVL 10

Assisted Solution

by:pclinuxguru
pclinuxguru earned 500 total points
ID: 37787705
It's possible it's stuck on his mac and his mac keeps resending the same email.

You can use the message tracking in under tools to confirm it.

Personally i would turn on the logging for smtp, clear the Queu and see if the same email re-appears and then run the message track on it and see it is coming from the mac or exchange.

The NDR is saying it is simply delayed which is normal for delayed email after a certain period of time.
0
 
LVL 10

Accepted Solution

by:
pclinuxguru earned 500 total points
ID: 37787734
I searched through EE and found this:
http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_24461057.html

it is pretty much what I said above.
0
 
LVL 1

Author Closing Comment

by:crcsupport
ID: 37796059
I guess it was the apple email client putting too much header information, the receiving email server could n't handle it properly. I sent the same email using outlook, it goes through without duplicate email
0

Featured Post

Top 6 Sources for Identifying Threat Actor TTPs

Understanding your enemy is essential. These six sources will help you identify the most popular threat actor tactics, techniques, and procedures (TTPs).

Join & Write a Comment

If you don't know how to downgrade, my instructions below should be helpful.
Are you unable to connect or configure Hotmail email account in Microsoft Outlook 2010, 2007? Or Outlook.com emails are not downloading to Outlook? Lets’ see the problem and resolve Outlook Connector error syncing folder hierarchy (0x8004102A).
The video tutorial explains the basics of the Exchange server Database Availability groups. The components of this video include: 1. Automatic Failover 2. Failover Clustering 3. Active Manager
The basic steps you have just learned will be implemented in this video. The basic steps are shown to configure an Exchange DAG in a live working Exchange Server Environment and manage the same (Exchange Server 2010 Software is used in a Windows Ser…

762 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

Need Help in Real-Time?

Connect with top rated Experts

24 Experts available now in Live!

Get 1:1 Help Now