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Helpful answers
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Jul 27, 2016 5:37 AM in response to indigotygerby JimmyCMPIT,one way to do this is to make invisible files on your mac temporarily visible. If you proceed with this method make sure you have a current backup and do not remove unidentified files, many of these are for the system to function correctly and do not need to be managed by the user (hence, they were made invisible by the OS)
Connect your ipod
Open the Terminal (Macintosh HD/Applications/Utilities/Terminal)
type
defaults write com.apple.finder AppleShowAllFiles YES.
Press return.
Hold the 'Option/alt' key, then right click on the Finder icon in the dock and click Relaunch.
the contents of your iPod will now be be browsable, the contents will show as four character long file names that appear to be named at random. This will make it difficult to identify what is what but once you drag these into the iTunes window they should accept the meta data and convert over correctly, or you have to do them by hand (it's been a long time since I had to do this, but it did work at the time)
once you complete the copy
Open the Terminal (Macintosh HD/Applications/Utilities/Terminal)
type
defaults write com.apple.finder AppleShowAllFiles NO.
Press return.
Hold the 'Option/alt' key, then right click on the Finder icon in the dock and click Relaunch to allow the invisible files to return to their "invisible" state.