Unchecked/Checked songs in my self-created Playlists on iTunes disappear whenever I sync my iPod

Question

Unchecked/Checked songs in my self-created Playlists on iTunes disappear whenever I sync my iPod

Running iTunes 12.2.2.25

64-bit

Windows 10

I've been having this problem with iTunes where one of my playlists, "Movie/TV music" started with many songs, some checked and unchecked. I like to upload only songs that are checked to my iPod, however I still want to see all the songs (checked or unchecked) in the iTunes player and listen to unchecked songs when I want. I have been experiencing an issue where I plug in my iPod to sync it and later upon returning to iTunes all songs that were unchecked no longer display on iTunes. This has also spread to songs that are checked are disappearing. None of the original mp3 files are deleted and if I add those deleted songs to the iTunes player they restore to their checked/unchecked position. Any thoughts on this? I'm wondering if something screwy is going on with the sync process?

iPod (5th generation), iOS 8.3

Posted on Aug 19, 2015 5:38 PM

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Answer 1

brenden dv

Community Specialist

Aug 21, 2015 6:37 AM in response to TheOldRepublic7

Hi TheOldRepublic7,

I'm sorry to hear you are having these issues with iTunes on your Windows machine. If you are having unusual display behavior with various songs (song file is still there, but iTunes stops displaying it), you may want to make sure you have a current backup of your data (including your iTunes Library files), then try rebuilding the library as outlined in the following article:

iTunes: How to re-create your iTunes library and playlists - Apple Support

Regards

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Answer 2

Oct 4, 2015 12:07 PM in response to brenden dv

Thanks, I'll check it out.

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