Once you're connected, you'll see a setup dialog where you can make sure the VoiceOver kit is enabled and decide whether to sync music automatically. Leaving this box checked is the quickest way to get up and running, but since the Shuffle's capacity is rather limited, iTunes will likely grab a random selection of music from your library instead of the whole collection. If you'd rather have direct control over what music is added, leave the box unchecked.
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