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please use the windows media player 10, click on sync and put all the songs you want in the sync list then click on start sync and it should sync properly without any problems.
Did it always do this...if so it may just be the way the unit was built... a way around this is to turn on shuffle so even when it starts at the begginging you dont hear all the same songs over and over.
Make sure that the mp3's that you upload in the phone are in the correct folder, moreover make sure that the folder itself is named correctly otherwise the phone won't recognize it and might just ignore.
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