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Server 2003 to 2008 Migration My Docs problems

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http://serverfault.com – I have a school with about 100 teachers and a complex situation. Every year the teachers turn in their laptops for 1 week for maintenance. After that we send them back out so they can prepare for next year over the summer. After this happened My co-worker did a Server 2k3 to 2k8 migration and then left the company. Everything seemed fine then we noticed that any teacher that opened a document in their My Docs folder (which was on the 2k3) offsite, prior to the migration those files will not sync to the 2008 server. However as long as they opened their documents after the migration to the (HowTos)