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Outlook cache does not retain data

One of our users is unable to write to his nk2 file.  The addressee cache remains only in temporary storage, and once he restarts, the cache is lost.  I went to look at his cache file, and it wasn't even there.  

So I changed the permissions on the Outlook directory to remove any read only attributes, opened Outlook, addressed a message, closed Outlook, and the file appeared.  However, that change is the last that has happened to the file.  It is not updating.   I verified that he has permissions on the file.

Original question below (he was given an entirely different system following the list of attempts to remedy below):
We are in an Exchange 2003 environment with Windows XP Pro and Outlook 2003.

We have a partner who recently acquired a Dell Latitude D620.  This is a relatively new laptop as it was bought in the last year.  It has had one prior owner, and it was given a fresh image prior to assignment.  The user indicates that ever since he received the laptop, his Outlook cache randomly drops addresses.  I tested and verified this myself.  I could send to one address, restart, and the address would still be in cache.  I would send to another address, restart, and the address would not be in cache.  

We tried deleting the Outlook file that contains this data (I forget which one it is off the top of my head).  That didn't work.  We tried deleting frmcache.dat (just because it seems to be the fix it all for Outlook).  That didn't work.  We recreated his profile.  We had him not run various programs.  We recreated his profile.  We built a new image for the laptop and redid the whole thing.  The issue still persists.

I started thinking this might be coming down from his Citrix profile, as he does not have a roaming profile to consider.  However, he indicates today that his Hearts game also lost his stored name.  

Please advise.
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I used the bottom 2 utilities originally to view the nk2 file for any records that might give indication of corruption, and to copy the contacts in to the cache.  

While contacts are certainly the superior way to store the information, one cannot reason with a partner who insists it is inefficient and that his billing hours are suffering.  So I still need to figure out why the cache is not updating.
if you enable Contacts as Outlook Address Book, the contacts addresses will appear when you click on emty space in To field.

Enable Contacts Database As An Email Address Book in Outlook 2003
http://domino.lancs.ac.uk/pub/usghelpdesk.nsf/9fb9e62b73055de48025680100698378/c8dbe9bb81766cf080256e5800438856?OpenDocument

For Outlook 2007, here is how to enable Contacts as Address Book
http://office.microsoft.com/en-us/outlook/HA102194281033.aspx
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I will try to convince the partner to add everyone he emails to his address book, but he insists it is a waste of his time to create an address book entry.

As a work around, if I can sway him, that would be great.  But I really still need to find out why Outlook won't write to the cache file.

What I've found is that I can modify it from utilities like nk2view, but that Outlook itself will not.  Any ideas on what would cause Outlook to be unable to save changes to the NK2 file?
The outlook.nk2 could be corrupt.  With Outlook closed, rename it. Then open Outlook and type in an address to send an email. Next time the address should be remembered.
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We did that.  Three times.  
I've now tried setting his address book to pull first from contacts, and his mail options to download an offline address book...  I'll post back when I hear from the user.
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No luck with the most recent attempts.  And I did try to convince the partner to use his contacts.  He simply insisted that the cache is supposed to work, used to work, and must be fixed.
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