Still celebrating National IT Professionals Day with 3 months of free Premium Membership. Use Code ITDAY17

x
?
Solved

Dulplicate outgoing email from Mac, MS Exchange 2003

Posted on 2012-03-30
7
Medium Priority
?
594 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
[X]
Welcome to Experts Exchange

Add your voice to the tech community where 5M+ people just like you are talking about what matters.

  • Help others & share knowledge
  • Earn cash & points
  • Learn & ask questions
  • 4
  • 3
7 Comments
 
LVL 10

Assisted Solution

by:pclinuxguru
pclinuxguru earned 2000 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
What is SQL Server and how does it work?

The purpose of this paper is to provide you background on SQL Server. It’s your self-study guide for learning fundamentals. It includes both the history of SQL and its technical basics. Concepts and definitions will form the solid foundation of your future DBA expertise.

 
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 2000 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 2000 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

Free Tool: SSL Checker

Scans your site and returns information about your SSL implementation and certificate. Helpful for debugging and validating your SSL configuration.

One of a set of tools we are providing to everyone as a way of saying thank you for being a part of the community.

Question has a verified solution.

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

How to resolve IMCEAEX NDRs in Exchange or Exchange Online related to invalid X500 addresses.
This article will help to fix the below errors for MS Exchange Server 2013 I. Certificate error "name on the security certificate is invalid or does not match the name of the site" II. Out of Office not working III. Make Internal URLs and Externa…
To show how to generate a certificate request in Exchange 2013. We show this process by using the Exchange Admin Center. Log into Exchange Admin Center.:  First we need to log into the Exchange Admin Center. Navigate to the Servers >> Certificates…
There are cases when e.g. an IT administrator wants to have full access and view into selected mailboxes on Exchange server, directly from his own email account in Outlook or Outlook Web Access. This proves useful when for example administrator want…

721 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