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I have setup a new Server 2008R2 DC to run a new domain. I have also setup folder redirection for client machines Desktop and Documents.

Its all working okay, except I added a Win 8.1 client to the domain which had a local user account which a user had been using before they had a domain in place. I used Profile Wizard to migrate the local account to the new domain account and as expected when I logged the user in to his new migrated account his desktop and documents started to copy to the server.

However, I hadn't noticed that the user had 75GB of data on his desktop. The process of copying files was taking an age, so I decided to copy the files to his downloads folder which is not part of the redirects.

After the copy had finished I deleted the files from the desktop. I rebooted the machine and expected that the offline files sync would see that the files had been deleted and then take care of the deletion on the server.

Well it seems for some reason the files are still being copied to the server. I checked in resource manager on the server under disk io, and I can see the names of the files being written to disk. Theses files no longer exist on the workstation.

Do I need to do something to get offline files to see the deletion. Do I need to empty the cache?

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I would clear out the Offline Files (CSC) cache, otherwise it's going to keep trying forever. The FixIt in this KB article will do the trick: http://support.microsoft.com/kb/230738

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