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Email Delivery to a Distribution Group and message tracking that email

Posted on 2014-04-23
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Last Modified: 2015-06-25
This is a very odd situation and it involves two somewhat related issues.  

1. We are using Proofpoint for a SPAM filter and have had no major issues until I recently created 4 mail enabled security groups. I was informed that external emails were not being delivered to these groups.  I performed a search on our Proofpoint site, found the emails in question, which had a Status of sent.  The MTA log shows me that it has indeed been delivered to our CAS server (Hub Transport).   As far as I can tell,  this is only occurring with groups which have been created since we started using Proofpoint.   All pre-existing groups are functioning correctly.   But Proofpoint points to the fact that message is being sent and is telling me it's not their problem and I need to track the message internally.  

2. Whether I run a powershell command (get-messagetrackinglog etc. ) or run the exchange troubleshooting assistant, using the SPECIFIC Internal message ID number. I always get back no results found, which is impossible.  
ANy thoughts would be appreciated.
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Question by:dpvone
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LVL 9
ID: 40048085
If you can see the messages in the spam filter, can you redirect the message to yourself to see if changing the mailflow allows the message to land?  It sounds like the email messages are being mishandled when they get to the hub transport.  Perhaps having the message forwarded from the console at the spam filter to another user (if possible) will get you started down the right path.

Have you tried the exchange connectivity analyzer http://testconnectivity.microsoft.com for inbound smtp email using one of these groups as the target?
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dpvone earned 0 total points
ID: 40059592
Thanks,  I found the issue and it actually makes the behavior described above make sense.   In Exchange 2010 (don't know about 2007)  when a distribution group is created, Exchange by default turns on a parameter to only allow email from authenticated users:  Properties > Mail Flow Settings > Mail Delivery Restrictions > Checkbox is turned on "Require that all senders are authenticated" .  I unchecked this box and the group could then receive external email.

SO anyone who doesn't authenticate on the domain, in other words ALL external email,  cannot send email to the group and there is no bounce back or message.  The spam filter delivers it because the group is defined there but Exchange never has any record of the message.  While I can understand somewhat the need to limit external access to a distribution list this should not be turned on by default.   Many companies I've worked for use lists for a wide variety of reasons, many of which are to manage email from external addresses.  We for example use them for contest responses, surveys, and to interact with business partners.  We also use lists when registering for products, support, or forums ( such as this site) so that responses and information are disseminated to the entire group.
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by:Seth Simmons
ID: 40850264
This question has been classified as abandoned and is closed as part of the Cleanup Program. See the recommendation for more details.
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