Q: iPhone Syncing Problem
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Sep 1, 2015 9:27 AMby alex_h1,Hello EthanHuntington,
Thanks for using Apple Support Communities.
From your post I understand that you'd like to manually manage the music on your iPhone, but it's not allowing you to move music to it in iTunes. Given you said this happened only after some updates, then you might've enabled Apple Music with iCloud Music Library on the iPhone. Having this option enabled will prevent you from syncing music to the iPhone in iTunes.
If you're a member of Apple Music or have an iTunes Match subscription, you have iCloud Music Library turned on. When you have iCloud Music Library turned on, you can't manually manage music.
Move content from iTunes on your computer to your iPhone, iPad, or iPod touch - Apple Support
Take care.
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Sep 5, 2015 1:22 PMby alex_h1,Hi EthanHuntington,
I'm sorry to hear that the issue persists. For further troubleshooting this issue I suggest that you get in contact with our support by using the link below.
Apple - Support - Product Selection
Have a great weekend.
