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Well firstly on Media Player, have a playlist. You can create one by dragging music to the "Now Playing" column on the right-hand side, then by saving the playlist. Next, open iTunes and click file (up the top) and click Import. Find the place where you saved the Windows Media Playlist. Click the playlist. There will be some load time then when thats finished, you will have all your music from the playlist ONLY on iTunes. If you want all the music to iTunes, then you must make a playlist with all the music. Then save, import etc.
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