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Songs no longer sync to my iPhone 5s

Songs no longer sync to my iPhone 5s

I've had my playlist of local files that are on my laptop downloaded and available offline for over a month now and when I accidentally switched Available Offline to the OFF side earlier today all the songs were removed. I didn't panic and turned it back ON again, but now I am panicking because nothing is redownloading even though I am connected to the same Wi-Fi as my laptop. All I see is "Waiting to download." at the top of the screen. I tried downloading a different playlist and that worked FINE but whenever I try and download a song from that local files section on my laptop it fails.

 

Please help fix DX

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Removed my iPhone 5s from my list of Offline Devices and now I have no idea how to get it back on the list so I can redownload these playlists... SOMEONE HELP PLEASE

89 Songs, over 4.0 GB left on my phone, what's up???

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