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Cannot play synced music - crashes

Cannot play synced music - crashes

So this has been going on for a while. At first I could sync music to my playlists and listen to them but after a while a window came up saying it was not synced. Nowadays when i sync my music an then play them on my phone, spotify just shut down. Have I done something wrong? Is there anything i can do to make it work again?

 

Im using a HTC Desire HD.

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