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Internal NDR's for some mailboxes on Exchange 2010.

bworley1404 used Ask the Experts™
We're migrating mailboxes from Exchg 2003 to Exchg 2010.  The Move Mailbox feature will not work for us, so we are manually moving the mailboxes by exporting them from the 2003 to a .pst, deleting the user's mailbox, then creating a new mailbox for the user on the 2010 server, and then importing the .pst into the users mailbox.  This works without any error.  Most of our mailboxes are still on the 2003 server, although we have moved 3 mailboxes to the 2010 server.  Mail is flowing back and forth.  Yesterday, we migrated 2 mailboxes via the process above.  We can send emails from either of these accts to any other mail acct on the 2003 or 2010 servers, but if we send emails between these two accts we get an NDR.  It appeared this was an Outlook cache issue, so on each user's machines we deleted their Outlook profile, renamed any .ost files to .old, and deleted an .N2K files, then created a new Outlook profile...still the same problem.  

I can't figure out why this is happening with just these two mailboxes, so far.  I'm hessitant to move any other active mailboxes because I don't want this problem to be expanding to any more users.

One other item that I find odd...our mail server(s) accept mail for two different domains...@company1.com and @company2.com.  (most front office users have their primary email address as @company1.com, but our IT and administrative users have their primary email address as @company2.com.)   The Default Accepted Domain on the mail server is company1.com.   The two mailboxes having the problem have primary email addresses as @company2.com (their default reply address)...AS I said above, if the users send each other emails to the @company2.com address, they get an NDR (#550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found ##), BUT if they send the email with the address of xxxxx@company1.com, the email is delivered.   So, this is making me think it is not an issue with Outlook caching (especially since we tried deleting all of the cached files), but perhaps more an issue with some configuration on the server?  Any ideas?
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is this an interorg move? make sure the domain company2.com is listed under get-accepteddomain


Yes, this is an interorg move.  We've upgraded from Windows 2003/Exchg 2003 to Windows 2008/Exchg 2010.  Within Exchg Management Console I see both domains listed under the Accepted Domains, and if I go into EMS and issue a get-accepteddomain I see both domains, as well.  Both are Authoritative Type which they should be, and as I stated before, the company1.com is the Default.


Anybody have any ideas on this?  This doesn't make sense to me why this is happening.  I've had this type of setup before at another company.  Basically, a configuration with one forest/domain with one Exchange server (2003) migrating to a new Exchange server (2010).  We're accepting email for two different domain names...we were on the 2003 server without a problem, and should be able to on the 2010, as well.  All of the users have SMTP addresses for both mail domains....most have company1.com as their primary address, and a few users have company2.com as their primary address.  Not sure if this matters, or not, but the first two accounts we've migrated have the company2.com SMTP address as their primary address.  We also have two service/generic accounts that we have moved to the new server.  The first two accounts can send emails to users on the 2003 box or to the service accounts ok.  When they send emails to each other we get the "IMCEAEX- O=DOMAIN OU=First+20Administrative+20Group cn=Recipients cn=user1@company1.com" "550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found" NDR.  The message headers show that the email is going from user2@company2.com to user1@company2.com, but the error message above shows the recipients email address as the user1@company1.com address??

We've tried deleting the .NK2 and .ost files on the Outlook profile, but it had no difference.  Regardless, I don't know why it would still have a problem if both users have both SMTP address formats set up for them?
make sure the legacyExchangeDN value for the mailbox you received the NDR for matches the value in the NDR
We ended up opening a Microsoft incident, and here was the resolution.  We were migrating from Windows 2000 running Exchg 2003 to Windows 2008 running Exchg 2010.  It turns out that the recommended migration is to bring up the new environment and issue "Move Mailbox" calls in order to have the proper Exchange attributes set up in AD.  We were unable to do this due to logical errors in the Exchg 2003 metabase as per Microsoft's determination.  Our option was to run the isinteg utility which we were told would attempt to clean up the logical errors, but that we could possibly lose data, so we did not want to go this route.  We chose to Export the mailboxes to .pst's and then import them into Exchg 2010.  What we were missing, and was informed of later, was that by doing this, the exchg attributes in AD would not be created correctly, or overwritten by the import of the .pst....again, this is how it was explained to us.  So, in order to work around it, we had to create the X500 custom address for each mailbox user.  Once we did this, everything was fine.  Just to note, this was still related to the Outlook caching on the client, but we were intermittantly having successful/unsuccessful results until we created the X500 addresses.  

For us, this solved our problem, and therefore, this question can be closed.
which is where i was going when i asked about the legacyExchangeDN, this is what you would use for the X500 address
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This question has been classified as abandoned and is being closed as part of the Cleanup Program.  See my comment at the end of the question for more details.