From ArsTechnica:
Apple didn’t really mention the expansion of Autofill when it announced iTunes 8.1 and, unlike Genius, iTunes itself doesn’t exactly get in your face about using Autofill. In fact, you’ll have to visit a few different screens to use the feature, although enabling it isn’t difficult by any means. Basically, once your iPod is connected, visit the Summary tab and make sure you’re set up to “Manually manage music and videos.” Once you’ve done that, use the triangle to reveal the contents of your iPod or iPhone, and click on Music, at which point you’ll see the source selector, Autofill settings, and Autofill button at the bottom of the screen.
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