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Internal NDR after Exchange migration to Office 365

Posted on 2013-01-14
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Last Modified: 2013-03-13
Hi, I just migrated our old Exchange 2003 server to Office 365.  Everything is running well, except we are getting NDR's when sending internal email.  Does this have something to do with how the old Exchange server sent internal mail?
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Question by:IgniteITNS
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Author Comment

by:IgniteITNS
ID: 38777162
So it looks like this is an Active Directory issue.  When a user selects a coworker from the Contacts list, the email will go through and autocomplete will fix the email address.  But you have to send them an initial email first.
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Expert Comment

by:ArneLovius
ID: 38779740
to expand on IgniteITNS

if people are using saved autocomplete entries, these will fail as although the display name will remain the same, the back end data has changed.
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Expert Comment

by:Maen Abu-Tabanjeh
ID: 38780160
what the NDR code?
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Accepted Solution

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BlueCompute earned 500 total points
ID: 38780856
So it looks like this is an Active Directory issue.  When a user selects a coworker from the Contacts list, the email will go through and autocomplete will fix the email address.  But you have to send them an initial email first.

Close.  For internal users outlook uses the LegacyExchangeDN address (also known as the x500 address).  The cached autocomplete entries reference the x500 address, which the new external exchange server can't resolve to a mailbox.  If the user sends an email to the smtp address (someone@somewhere.com) then that entry will be added to the *.NK2 file, so future emails will be sent correctly.

There are two ways of resolving this, one more elegant than the other:
1) Train the users to type the address in once for each contact (the first time they send to them), or edit the autocomplete entry using something like Nirsofts NK2edit.

2) Determine/extract the x500 attribute from your AD using ADSIedit or similar and have these LegacyExchangeDNs added as additional addresses to the mailboxes on O365.  This blog documents the process: http://joystickjunkie.blogspot.co.uk/2012/07/office365-migrations-and.html

There seems to be a lot more good gen out there if you google 'office 365 legacyexchangedn' so hopefully that'll see you right.
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Expert Comment

by:ArneLovius
ID: 38781182
@BlueCompute beautifully written
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Expert Comment

by:BlueCompute
ID: 38782978
Thanks ArneLovius - I'm thinking of turning some of my answers here into blog posts or a pewrsonal KB so I'm trying to make them as complete and clear as possible without going overboard.
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Author Comment

by:IgniteITNS
ID: 38980237
I've requested that this question be deleted for the following reason:

was typed in by ex employee,
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Expert Comment

by:ArneLovius
ID: 38980238
You seem to be saying that multiple users have access to a single account.

http://www.experts-exchange.com/terms.jsp

If you register for Services, these Services are for the registered user ONLY and may not be shared or features transferred to others
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Author Comment

by:IgniteITNS
ID: 38981902
No what I'm saying is that the IT guy I paid who was using this account was let go. I am now doing his job.   Only one user guys....
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Expert Comment

by:ArneLovius
ID: 38982142
I am 100% sure that the answer provided by myself and exceptionally well described by BlueCompute is correct.

I would split the points 50/50 across posts 38779740 and 38780856


The issue of an account being " transferred to others" ...
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