The easiest way (though tedious when you start) I found was to just sync all my music, etc. through Window Media Player, then open the Walkman in Windows Explorer. Open the music folder and create a file for the music you want on the playlist. Copy all the songs you want the select the songs in the file, right click and create a playlist. Double-click on the playlist and put them in the order you want them. Click OK. Whan you disconnect the walkman, your playlist will be there. This is the only way I have found to actually have my playlist show up in the Playlist feature on my Walkman in the order I want the songs.
Use the Driver software that came with the player. There should be a Playlist tab. Organize it and sync it to the player. You can also do this in Windows Media Center.
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