Exchange 2007 multiple SMTP domain issue

20 pts.
Tags:
Active Directory
Exchange 2007
SMTP
I have an Exchange 2007 organization that contains multiple SMTP domains. AD is configured so that each user has multiple e-mail addresses, one from each SMTP domain. Most of the time, all is well. However, sometimes, (more often than I'd like) if an internal user tries to send a message to another internal user using the alternate address, we get an NDR that says the user does not exist. Even more interesting is the hash it generates in the NDR of the recipient it is trying to find. It tries to query a user like so: user.namesecond_domain@first_domain.local. Of course the lookup will fail this way, but where does it get that address, and why does it work as expected most of the time?
ASKED: December 28, 2007  6:04 AM
UPDATED: December 31, 2007  6:24 PM

Answer Wiki

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Problem solved. The issue was that some of the mail clients still had cached recipient information from a previous Exchange installation. To fix this problem:

1.) Delete the Outlook clients nickname cache file by searching the local Outlook profile for a .NK2 file and deleting it.

2.) Change the Outlook to non-cached mode to ensure it is not a cached entry from the Offline Address Book.

3.) Check the behavior in OWA to confirm the server is generating the correct address list and has updated the GAL.

Cheers!

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