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May 26, 2015 11:36 AM in response to usernamejabby joe_7399,Greetings usernamejab,
Welcome to the Apple Support Communities!
I understand that you are trying to drag an audiobook from iTunes onto your iPod shuffle, but the audiobook will not sync as you would expect. In this situation, I would recommend reading over the If you can't manually add or remove content from your device section in the attached article to verify that your iTunes is set up correctly to drag and drop items to your devices.
Manage content manually on your iPhone, iPad, and iPod - Apple Support
Cheers,
Joe
