I've been having the same problem on my workstation and tried the steps in at 
this page.
http://www.slickit.ca/2011/03/outlook-2010-auto-complete-cache.html
No help;
But, starting outlook from the command line with  /ClearAutoCompleteCache
Fixed the problem for me.

From: Dean Cunningham [mailto:[email protected]]
Sent: Sunday, October 16, 2011 6:32 PM
To: MS-Exchange Admin Issues
Subject: Outlook 2010/win7 - nicknames not "sticking"

Have a user recently upgraded to OL2010 and win7 against a exchange 2007 server

Yes , know they should use propercontacts, but the nicknames don't stick once 
teh user logs off.

Any bright ideas?

cheers
Dean

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