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Exchange emails not being sent?

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Got a strange one that I unfortunately don't even know where to check.  Running Outlook 2010 and Exchange 2010.  One user had been sending emails to our purchasing agent and was not receiving the product they were writing POs for.  Come to find out its because the purchasing agent wasn't receiving the emails. 

Then yesterday the purchasing agent received all the emails at the same time.  4 emails came through that had been sent over a 5 week period.  Where could I even look to try and troubleshoot this?

The only caveat to the setup is that I have been moving mailboxes from Exchange 2007 to Exchange 2010 (both servers are up and running with mail currently moving through the 2007 box).

Thanks.


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