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Exchange contact not receiving mail when part of a distribution group

I administer an exchange 2003 email distribution group.  The distribution groups are a mixture of users and AD contacts.  All the contacts are setup the same and everyone has been using the distribution group without a hitch ... until now.

One of the 'contacts' is not receiving the email.  Through testing we have established they can receive mail when addressed individually, but when we send out a mail to the entire distribution group, every get the email apart from this one contact.

We do not get a bounce back error message and there does not appear to be any hold-up in the system manager queue. I had concluded the problem was not at our end, but it's an important distribution list and I need to work out why this isn't working regardless.

I've had a search around here but none of the suggestions have helped me: -

I've tried updating the recipient service - didn't help.
I've tried exchange tasks on the contact to mail-enable the contact but all I get is 'Delete E-mail addresses' or 'Remove Exchange Attributes'.

I've joined specifically to try and solve this one, I would be very appreciative of any help :)



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ComCorpAU
Asked:
ComCorpAU
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2 Solutions
 
FearNoMoreCommented:
So this DL used to work fine previously...I mean...this contact received emails sent to this DL without any problems?
Also there are other external contacts in this DL that are receiving emails fine?
Have you tried creating a new test DL and adding the users and checking what happens?
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ComCorpAUAuthor Commented:
Hmmm... the DL has and still does work fine with the exception of this one contact ... to be honest I doubt this particular contact ever received email sent to the DL (hence why there has been a bit of a fuss about it this week :(  ).

Yes, there are plenty of other contacts in the DL and they work fine. I made some random calls to recipients and tested using a contact to my hotmail.

And Yes again, I created a test DL with my own hotmail and the problem contact and alas I received my mail in hotmail, but the problem contact didn't.

I also established that if the list was expanded (into individual emial addresses) then this would work.  However, my bosses don't want to reveal all the people in the list and also don't want the senders to have to remember an extra step in the sending process.

I also got the (problem contact) recipients IT dept to add our domain to their spam white-list just in case. Any ideas? or tests to identify the problem? and/or prove it's not our problem?

Thanks again



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FearNoMoreCommented:
Do message tracking and find out what happens to the email to this contact?
Go through the below article...It has helped to resolve many issues with DL's
http://support.microsoft.com/default.aspx?scid=kb;EN-US;839949
 
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FearNoMoreCommented:
I think that the problem is with the Expansion Server....is it set to "Any server in the Organization" ?
In the link I provided above check the title:
How the Exchange message categorizer expands a distribution list When a message is sent to a distribution group,
Can we change the Expansion Server to a specific server and not keep it to just "Any"
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ComCorpAUAuthor Commented:
I've read the support docs and can now see the role the expansion server and categorizer play.

I changed the Expansion Server on the properties of the distribution group from "Any" to our only Exchange server.  Unfortunately, after making these changes, the problem contact is still not receiving any mail to the distributuion group.

From the text logs and tracking center I would say that the categorizer is splitting the messages as I can see the problem contact email address within the logs. The message is then transferred to MessageLabs for scanning/delivery through SMTP.

Could there be anything in the outgoing message from a distribution group that an ISP or somesort of spam defence (further downstream) would not like?
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ComCorpAUAuthor Commented:
NEW Info: After writing the above post I remembered I could track and trace messages using the MessageLabs console.  From this I can determine that the messages to our problem contact do leave our exchange server to the correct email address of the contact.

Sender me@mydomain.com
Recipient problem_contact@hisdomain.com
Subject TEST 10 - Please Reply
Message Size 11 KB
Message ID CDB19284A77C1F48AC9C00E988ED1FA301365033@ourserver.comcorp.local
Message Reference 124096731200000369965420001201003
Date/time Received 29-Apr-2009 01:08
Received Result Accepted
Date/time Scanned 29-Apr-2009 01:08
Scan Result Passed
First Delivery Attempt 29-Apr-2009 01:08
Final Delivery Attempt 29-Apr-2009 01:08
Delivery Result Delivered

So I'm now more convinced the message is vanishing further downstream?

(BTW, I don't want to lead anyone in the wrong direction)

Thanks again
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FearNoMoreCommented:
Well yes...you are absolutely correct...
The email has indeed left your Organization....and also passed message labs
Did you confirm with the problematic contact that the emails are not getting redirected to Junk folder or any other folder?
Ask this user to check his OWA also
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ComCorpAUAuthor Commented:
Yes, I had the problematic contact checking their email junk ... and adding our domain to a spam white list.

As we could show the emails had left our organisation (and everyone else on the list was OK) we concluded the problem was not at our end.  I would still love to hear any suggestions about what this could have been, but have concluded this call here. If I find out more I will post it.
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