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I'm trying to create an "albums not played for the last 3 months" playlist, that I could sync onto my iPod.

Is it normal that autofill always chooses the same songs out of my library to fill the iPod with? No matter what I do to those tracks (listen to them on the iPod, try do delete them in "manual" mode), they always come back when I sync with autofill.

I do have quite a substantial amount of other tracks that I like as well, but it feels like autofill picked once and for all the tracks it likes most.

I have read the Managing Your iPod With Smartlists document (PDF) (non-PDF link) but nothing has come of it.

I own a 2G iPod nano (first generation) that I'm using together with iTunes 9.0.1 on my Mac.

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I sympathize completely. This is one of my biggest complaints with iTunes - that it doesn't inherently make any distinction between complete albums and "singles" - random tracks that aren't with a complete album.

What I've ended up doing is systematically clearing the album tag from all singles. You can then make a smart playlist that omits tracks with no album. If it bothers you to mess with the metadata that way, you can find a different attribute to change, as long as you're consistent and it's something smart playlists can filter for.

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I did not find a way to to this using smart playlists, but in the end i still acheived my goal (i.e. get random albums onto my ipod) thanks to an application called NanoFibre.

Enjoy...

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