First make sure that all the files in the playlist are supported by the device (all mp3 files)..also ..make sure that the playlist you are trying to sync contain only files that are in the library of windows media player ..(to be sure ..better scan all hdd again and add all media files on the library again )..
be sure that you do not have files in the Play-list that were originated from a disk or some device that it is not in use at the moment...cause this is the main reason for these kinda errors..
If it do not want to work ...better look for the device in My computer folder and load the files manually in the device(removable storage) using the copy/ paste feature..
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