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Helpful answers
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Mar 27, 2016 2:40 PM in response to APPHelppleaseby sterling r,Hi there!
It sounds like your iTunes keeps checking music that you are unchecking to prevent it from syncing to your device. I would start by using the section titled "Start iTunes in Safe Mode" in the following article to help troubleshoot the issue.
Fix unexpected quits or launch issues in iTunes for Windows
If there are no third party plugins then I would next use the section titled "Create a new user account" and work your way down the article from there to help isolate the issue to a specific user, or system wide issue. It will help you along the way as you go about it. Thank you for using Apple Support Communities, I would appreciate an update to let us know how that worked!
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Mar 27, 2016 3:26 PM in response to APPHelppleaseby turingtest2,It is purchased tracks that are rechecked? This seems to be a bug with the last few versions. Make a playlist of the content you want on the device and sync that instead, or make a playlist of the tracks that should be unchecked. You can then ctrl+click any check box to reset all tracks in that list should it be needed.
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