Try cleaning out the Outlook temp folder for the user. It is normally located at C:\Documents and Settings\username\Local Settings\Temporary Internet Files\. The folder that you want will be OLK# where "#" is a random number. You will need to show hidden files and folders in order to see the folder.
The easiest way to find the folder is to do a search for OLK in C:\Documents and Settings\username and include hidden files and folders in the search criteria.
If your user profiles are not on drive C: then substitute the correct drive letter.
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