2 options:
a) Outlook profile issues.
Create a new profile.
start > run > control
mail > new profile.
Pull all emails from exchange.
b) If A) doesnt work, create a test mailbox and connect outlook to that and test it from there.
It's easier to create a test mailbox, Exmerge all mails into that, and then have the user up and running, rather than trying to figure out why outlook is behaving in a particular way.
my $.02