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iPhone 5 Keeps Unchecking "Manually manage music and videos" on iTunes

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I'm currently having an issue managing my music on my iPhone cause it constantly unchecks the "Manually manage music and videos" from my iTunes and it won't let me manage my files on my iPhone.

Every time I want to manage my media files on my iPhone, I have to sync my iPhone and it deletes everything on it and then I have to transfer them to my iPhone again.

I noticed this only happens on my iPhone since it doesn't seem to happen at all on my iPad.

For those curious, it's an iPhone 5 with iOS 7.1 on iTunes 11.1.5. I have my iTunes set up so I can manage all of my iDevices via WiFi. The problem however persist even when I'm trying to manage my files when my iDevices are connected to my iMac via USB.

Does anyone know how to possibly fix this error?

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