Shuffle doesn't autofill all songs!

Really annoying.
I have a playlist of 69 songs and it only loads up 67 songs onto my shuffle.
It's not as if the songs are a different format either. Both songs have been purchased from the itunes store and are bona fide apple products but wont frigging autofill...!!!
And before you wonder, I have used only 487MB's of the 1GB capacity.
Yesterday it was fine. But then I updated itunes to the latest version, I'm wondering if that has anything to do with it???
Thanks.

Hi,
No error messages. The songs are checked, it plays perfectly in itunes, but it's as if it doesn't exist when I use autofill.
I've even restored the shuffle and autofilled with just this ONE file. It shows on the shuffle via itunes but STILL doens't play
Really bugging me now as I've paid £9.99 for it and can't play it on my shuffle.
Message was edited by: Sinnerman

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jangell2 wrote:
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