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Undeliverable internal e-mails unless check names is used

We have a 2010 Exchange server with Outlook 2010.  When one specific user sends mail to other internal users they get an undeliverable response. The only way around it is to hit Check Names. Cache has been cleared. This does not happen to other users, does not happen when sending externally. Any thougts?

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lineonecorp
Asked:
lineonecorp
5 Solutions
 
Shabarinath RamadasanInfrastructure ArchitectCommented:
see if this sender is having any entry in Outlook contact for the specific recipient. In contact, the email may be pointing to a wrong address.  Its mostly an Outlook issue.
Shaba
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TheSonicGodCommented:
In outlook, under addressing - what address books list in the box that show the address books to check names against. you may want to change the order of these listings if one of these address books is corrupt

Also, do you have enable "check names" in File - Options - under Mail settings - Send Messages tab -

And have you checked or unchecked  the "Automatic name checking" box

May want to delete and recreate the outlook profile for that user and rename to rebuild the OST file on the system
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kieran_bCommented:
If you create a new outlook profile, does the problem still exist?

If you create a new user profile, does the problem still exist?

If you move this user to a new computer, does the problem still exist?
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PostmasterCommented:
Is the address auto-filling?
If so, when it appears - just use cursor key to highlight and DELETE it.

If the recipient mailbox has been re-created for some reason, the old references to that mailbox will fail.
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lineonecorpAuthor Commented:
Thanks for all the responses. Let me try these techniques.
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MrPaulTCommented:
would you mind posting the NDR on here? This will help.
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lineonecorpAuthor Commented:
Thanks for all the help. We figured it out .  There had been an upgrade done to Exchange and in the process the old 'nicknames' file did not move over smoothly to the 'suggested contacts' file. As well, the problem only occurred when people were responding to e-mails that went back over a month.  Resolution was to clean the 'suggested contacts' of all old 'nicknames.'
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lineonecorpAuthor Commented:
Experts answer were not specifically the solution but helped us nail down the solution by isolation/elimination.
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