ANSWERS: 1
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Some mp3 players can't deal with file structures, so if you've got a neat and tidy file structure on your pc with everything in folders by artist or name, and you simply drag and drop that to your mp3 player - and that mp3 player can't handle structures - then you'll get that problem. If you can, try and drop a few mp3 files into the root directory without using any folder structure. Chances are the mp3 player will see those files. If it does, you have your answer.
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