Select “Devices” and check the “Prevent iPods, iPhones and iPads from synching automatically” box.
Select “Advanced” and check the “Keep iTunes Music folder organized” and “Copy files to iTunes Music folder when adding to library” boxes.
Plug your iPod into your Mac.
iPods and iTunes are meant to work together flawlessly. While you can transfer music easily from iTunes to the iPod, transferring music from the iPod to iTunes isn’t nearly so easy. In attempting to combat music piracy, Apple has not included an easy function for getting music off of your iPod and back onto iTunes. However, it can be done as long as you know how to use Terminal on the Mac.
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