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I am trying to copy old files from an OS X 10.5.8 to a new external HD. When trying to copy a folder I get the message:
The operation cannot be completed because you do not have sufficient privileges for some of the items.

I've checked the privileges and they seem ok (read & write for me). What is curious is that the folder is created empty on the target drive and I can then copy the contents from inside the original folder to inside the new folder without changing anything else.

This happens with several folders but not all and is making backup a pain. I have to figure out which folder broke the copy, copy its contents to the external disk and then select what hasn't been copied to copy (and eventually stop at some point and repeating the experience)

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Are you trying to copy a folder in your Users folder or some system folder? Also, if you check privileges, be sure to select that the privileges are applied to all the contents in that folder. It might be worth using something like Carbon Copy Cloner for this (bombich.com). –  fideli Dec 29 '09 at 4:52
    
Yes, the folder is inside my User folder. I verified that the privileges are applied to all the contents and even did a Repair Disk Permissions using Disk Utility following an article I found on Apple Knowledge Base. –  greye Dec 29 '09 at 10:27
    
What is the filesystem of the new external HD? Did you format it as Mac OS Extended Journaled (i.e. HFS+)? I have a potential solution that I've written as an answer. –  fideli Dec 29 '09 at 14:54

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There's an article on MacWorld (which links to an article at Apple KB) about repairing permissions and ACLs for the Users folder. Note that Repair Disk Permissions in Disk Utility does not do anything for the Users folder. It only repairs permissions of files of Apple-originating software listed in /Library/Receipts.

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