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Message: <blockquote data-quote="buzzard" data-source="post: 2848100" data-attributes="member: 3003">I haven't played with a shuffle, but I am fairly familliar with iTunes. I guess first off, did you import your music into iTunes? It won't simply search your HD or make assumptions based on where Windows stores stuff. You will need to actually import songs into it. This will not modify the songs, but merely enter them into its database and put them into its folder. Once that is done you should end up with all your stuff in the library. From there you can make either smart playlists or normal ones. Smart playlists allow for query types to choose the music on the list. Normal playlists you drag and drop manually onto the list. When you plug the shuffle into a USB port, it should appear in the iTunes list on the left. Given that I have an iPod bigger than my music collection, I am unfammiliar with the details of making playlists that fit into shuffles, so sorry, but I can't help you there. I believe there is an automated process by which it can take a random selection of music to fit the shuffle size. I also believe you can designate playlists that you want to dump on there yourself. buzzard</blockquote>