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File System Security and Ownership

As a Domain Admin I have created a Share on a Windows 2008 R2 server and given a particular user Modify permission to the share.  He has recently moved data from another system under this Share and when he does the Ownership changes to Unknown and I have to override it to reinstate the Administrator.  How does this happen when the top-level down is supposed to continue to inherit permissions?

Also, is there a way to have anything he moves under the share automatically inherit the permissions from the parent without having to force it?
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Paul MacDonald
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How, specifically, does he perform the move?
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I moves a folder via My Computer from another area on the same server.
Sorry for the typo - "HE" moves a folder...
Same drive/partition or different?


Does he own the original files?
Same Drive and Partion as well as same parent folder.  The source and destination folders are 1 level down from the parent and Administrators owns the source files.
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Paul MacDonald
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The Administrators, Domain Admins have Full permission.  So Copying on the same partition or in general will take on the paermissions of the parent?
Yes, but it seems like it shouldn't matter.  It's worth trying though.

Are the files encrypted, either at the source or destination?
No encryption at all...
weird