Missing emails when sending to distribution groups

I'm trying to track down a couple missing email issues and I was wondering what is the best way to do this in Exchange 2013.

Please also comment if you've run into either issue before.

Issue #1:  We have a distribution list with all internal members.  If the distribution list is used internally then all members receive the email.  If an external contact like HP or DELL emails the distribution list 1 member never receives it.
It is always the same member and the problem is repeatable.  Has anyone seen this behavior before and how do you recommend I track down the missing email?

Issue #2:  An admin is setting up meetings with the entire sales force.  She uses distribution groups to send the meeting invites, but not all the invited internal employees get added to the meeting or invited.  Thus far the problematic invitees are repeatable.

Environment:
      -Exchange 2013 CU6
      -Outlook 2010
      -Migrated from Exchange 2007
      -Shutdown Exchange 2007 servers 60 days ago
      -Uninstalled Exchange 2007 30 days ago
MwaddamsAsked:
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MwaddamsConnect With a Mentor Author Commented:
Thank you for all the suggestions.

It turns out the problem wasn't with our on-prem exchange or our clients.
We had a bad sync to our mailgate way and all groups for the user in question had been removed.
When an email came in from the outside to the distribution group it didn't see the problematic user as a member of the group and it didn't deliver to him.

Thanks again.
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roycbeneCommented:
The most important question, first and foremost, to ask is: how did you migrate? Was it via local moves or via exports and imports? Put another way, was the migration clean? Did the domain change? If not and the migration was clean, please see below:


Issue #1:

The message is getting to your Exchange server and it is being distributed if everyone but 1 recipient is getting it.

Couple things to check:

1. (The most obvious question) Have you checked this user's SPAM folder?
2. Check the distribution list properties in Exchange (just in case) to ensure you are not requiring that all users are authenticated.
3. Are you running Cached Exchange Mode? If so, disable it (for troubleshooting purposes) and try again. There is a chance the .ost file is corrupted.
4. Are there any rules filing the message from certain contacts somewhere else?

Check these and let me know.

Issue #2:

1. See Number 3 above
2. Are the users' calendars getting populated and they are just not receiving the emails in their inbox??? Or is there simply no trace of them receiving the invite at all?


-Roy
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MwaddamsAuthor Commented:
Roy,

Thank you for responding.

Issue #1:
1.  The emails are not in the user's junkmail and I don't see it in a delivery report in the EAC
2.  Senders inside and outside of my organization is selected in delivery management properties for distribution group
3.  User is in 'Online mode'
4.  No Outlook or Exchange rules

Issue #2:
1.  She was in cached mode, but I've now switched her to online mode
2.  No email is sent out and they're not added to the meeting either in the list of attendees
3.  Migration was done using built in migration tool in EAC.  The migration was clean and the domain did not change.
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roycbeneCommented:
In the 'Mail Flow Settings' tab in the properties of the distribution list, click on 'Message Delivery Restrictions' properties and see if 'Require that all senders are authenticated' is checked. If so, uncheck it. This will cause a problem.

Also, have you tried deleting the auto-complete entry on the sending computer for that distribution list (for the internal users)? To do so, start typing the name of the distribution list. When the name appears in the auto-complete list, hit the delete key and add it manually from the address book. The SID may have taken a hit when you migrated (unfortunately this is a common problem). Try that and see, as well. Keep me posted. :)

-Roy
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MwaddamsAuthor Commented:
I only see 'Mail Flow Settings' and 'Message Delivery Restrictions' for mailboxes, not groups.
In groups there is a tab called 'delivery management'.  In that tab I can select 'Only senders inside my organization' and 'Senders inside and outside of my organization'.  The later is the one selected.

I have not deleted the cached entry and will try that.  Another option I've asked her to try is expand all the groups in the TO field.  Although its not exactly the same problem I thought this article was close.  http://support.microsoft.com/kb/214633
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roycbeneCommented:
You may also want to try to update the offline address book:

https://technet.microsoft.com/en-us/library/aa997684(v=exchg.150).aspx 

Also, there are two types of rules. Server-side and Client-side. If you run outlook with the /cleanrules switch, it will delete all the rules, both client and server-side. You can start from scratch, then.

If these steps don't work, let me know. There are other options we can try.

-Roy
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SEHCCommented:
HI

I have had the same issue in the past it is to do with the email address being cashed in outlook.  they need to delete the cashed one and reselect it from the GAL.  

Try that I bet it will fix your issue.
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roycbeneCommented:
As mentioned in my post above:

"Also, have you tried deleting the auto-complete entry on the sending computer for that distribution list (for the internal users)? To do so, start typing the name of the distribution list. When the name appears in the auto-complete list, hit the delete key and add it manually from the address book. The SID may have taken a hit when you migrated (unfortunately this is a common problem)."

The SID will take a hit sometimes and the auto-complete entry needs to be deleted. Or, as you called it 'the cached one'.
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MwaddamsAuthor Commented:
issue resolve internally
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