Delivery Failure to FederatedEmail.4c1f4..... and DiscoverySearchMailbox

Users are getting a delivery failure message to these 2 system mailboxes (Exchange 2010) when they email a large distribution group. As far as I can tell these do not seem to be part of the said distribution group

 - FederatedEmail.4c1f4d8b-8179-4148-93bf-00a95fa1e042@.......
 - DiscoverySearchMailbox{D919BA05-46A6-415f-80AD-7E09334BB852}@.....
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Jon BrelieSystem ArchitectCommented:
Is this distribution group query based?  Was it possibly created under an earlier version of Exchange?

Try removing the group and recreating it.
sydlegAuthor Commented:
As I said they are not part of any group.
Jon BrelieSystem ArchitectCommented:
Right.  I'm talking about the distribution group that you specifically mentioned in your original question.  

Sending email to that group is what triggers the delivery failures to the other mailboxes, is it not?

Is that group query based, or possibly created on an earlier version of exchange?  Have you tried removing and recreating the distribution group?
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sydlegAuthor Commented:
One of the groups is Dynamic but I did run the upgrade scripts for all the groups, contacts etc...they seem ok
Jon BrelieSystem ArchitectCommented:
Delete and recreate the group using the 2010 tools and see if the problem persists.

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Jon BrelieSystem ArchitectCommented:
Wait, so do you get this error when you send email to a specific large distribution group, or when you use any large distribution group?

sydlegAuthor Commented:
Part of the issue was that when you create a Dynamic distribution group it automatically adds the omissions for these system mailboxes in the filter. When I converted these groups from Exchange 2003 server, the omissions were not added automatically as part of the conversion process
Jon BrelieSystem ArchitectCommented:
So what did you ultimately do to fix the issue?
sydlegAuthor Commented:
Your suggestion was a solution to the matter.

However, the point of my comment was to supply extra information for the cause of the issue, therefore providing others with another possible solution, which would be to alter the filter and not do a wholesale delete and recreate.
Jon BrelieSystem ArchitectCommented:
Gotcha.  Just curious.  Thank you for the clarification.
sydlegAuthor Commented:
No problemo matey :)
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