MS Outlook 2000 - adding attachment through Insert File/paperclip into message problem

Environment is Exchange 2000 with Windows 2000 & Outlook 2000 on the PCs.  I've got a user who for the past few days has been unable to add attachments by clicking on the paperclip for Insert File in a message that he wants to send.  When he does click on the paperclip, he gets the typical Insert File prompt, but instead of seeing all of the contents of his My Documents folder, its just about 8-10 folders between T and U.  In addition to the "missing" files & folders, Outlook hangs and after about 30 seconds he receives the typical "program is not responding" prompt and has to End Task on Outlook.  No problems opening attachments.

Have verified that the folders documents are actually there in My Documents.  Able to attach files by dragging them into the new message.  Have scanned for viruses and the unit is clean.  Have also installed all of the critical Windows Updates, ran a Defrag and disk check.  Nothing on the MS website or other searches have given any clues as to what this might be.

Hopefully someone else has seen this before.  Thanks in advance.
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Has he done this yet

on the menu Help > Detect and Repair
And it may be an OS issue do give this a go

Start > Run sfc/ scannow


Start > Run chkdsk /f
then defrag
lreesAuthor Commented:
CrazyOne - tried the detect and repair as the user (who only has user rights) and of course got the error about no Office installation source.

Already did the disk check and defrag.  Don't recall what the sfc /scannow was for though.

Logged in as myself (remotely with vnc) and decided to check and see if I had the same issues under my profile.  This is where things get weird.  Under my profile, no problem going to My Documents.  So, figured might as well try accessing his My Documents folder.  Browsed down and located the folder and boom - same set of folders displayed and Outlook hung.  Drilled down through My Computer and yep, all 139 files and folders displayed in the My Documents folder.  That's not counting the stuff within the subfolders - just what was in My Documents itself.  Created a couple of folders (called A-folders, B-folders, etc) and moved the folders that started with those letters in to the corresponding folder.  Did about 6 different letters and dropped the count to under 100.  No problems viewing/accessing the user's My Documents folder through the Outlook Insert File window.  Started moving stuff back.  When there were 138 files and folders in the My Documents folder, it works.  But as soon as it hits 139 and higher, it hangs.

I had a similiar problem with one of our users. Whenever he tried to attach a file from a network drive to an email, Outlook would hang. I thought it was his computer, but then I tried it on my computer and same thing. It seemed it was the directory. The directory had about 107 files and folders combined. I took all the loose files and placed then in a directory, then started sorting them out. I put the docs in a word folder, xls in an excel folder, and the rest of the bunch in a misc folder. I tried to attach a file again and I drilled down to all the word and excel folders without any problems. Except for the misc folder, Outlook would hang there. So I started removing files to see which file was making it hang. It turns out that the very last file I removed was a shortcut. I guess it was corrupt or something. So maybe that 139th file that have is corrupt.

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