Exchange 2010: Certain users cannot email certain other users

We upgraded our Exchange 2003 on Win2003 to Exchange 2010 on Win2008 R2 recently.  The X03 server has not been demoted yet, but is currently turned off.  The issue I am having is that one particular user (USER 1) cannot email another particular user (USER 2) whose name shows up in the global address list.  User 1 can see and select User 2 in the global list, but gets a non-delivery reply.  

Note that this only happens when User 1 tries from inside the network.  From OWA, User 1can email User 2 fine.  Note also that User 2 can send emails  to User 1 from any location.

The only possible cause I can think of is that when moving mailboxes from 2003 to 2010, User 2's mailbox would not move.  I kept getting errors.  I finally downloaded its messages to local folders and deleted the account from active directory.  I then recreated the account, established a mailbox on the 2010 server, and reloaded the saved messages from the local folders.  This procedure worked well, but I'm wondering if the User 2 entry in User 1's Global address list is actually tied to the old account?

The strange part is User 2 does not seem to be having any difficulty receiving email from anybody else (at least I am not aware of any difficulties.)


p.s.  This is a school and I am responsible for a few classes.  I will try to monitor this, but may not be able to respond as promptly as I would like.
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jojo_ORConnect With a Mentor Commented:
Check under Organization Configuration/Mailbox and look for the Offline Address Book tab.  Make sure that the distribution mechanism is setup for web-based and public folders.  You can right click on default OAB, go to properties and enable web-based distribution on the distribution tab.  I'm wondering if the OAB for user 1 has to be updated.
Does it still do that if you turn on the old e2k3 server?  Want to get that out of the equation.  Also are users using cached mode for outlook?  Might be the OAB on for user1.  Are you using public folders for e2k10, or http as well?
I meant public folders for OAB for 2k10.
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srsdtechAuthor Commented:
Hi jojo,
First, the issue does still occur if the X03 server is on.  And yes, users are using cached mode for outlook.  Re: Public Folders--I have not configured any on purpose.  But some of the configuration questions were confusing to me and I may have turned something on inadvertently.  How do I check to see for sure?
srsdtechAuthor Commented:
Okay, I checked that.  Web-based was not enabled.  I chose the default for the location of the OAB.  How do I update the OAB for a single user?
srsdtechAuthor Commented:
Never mind.  I got it.  The changes you suggested plus turning on the System Attendant solved the issue.  Thanks!
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