Actually - 1) Plug in iPod 2) Wait a f**king age for iTunes to load 3) Look at the songs you want to load up - they should be in order if you care about the ID3 tags - and select them 3a) If you have a shuffle, you must either select all the songs or create a playlist, the shuffle takes a lot longer to transfer. 4) click and drag 5) eject If it's a wma, it will convert it straight away as soon as you add it to the library. I don't like WMP, iTunes is so much better laid out. I tell you what, it pisses me off having many ID3 tags for one artist. For example, Lost Prophets, lostprophets, Lostprophets, LostProphets, and that's without typos. Then, when you scroll through your ipod, you have to enter each different version of the same artist to find the one song you want to listen to. If you changed them all to the same thing, they're all in the same place. YOU KNOW IT MAKES SENSE.