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Simple - if you "jailbreaked" your iPhone, you won't get the 'free' update, you'll get bricked.
Also, if you've jailbroken your iPhone, Apple probably isn't getting their $20/month "cut" from the "new at&t".
BUT - if you have an iPod touch, there's no recurring revenue to Apple, unless you pony up $20 for the software upgrade.
It would further add insult to injury if the $20 upgrade bricked your iPod touch...
(Pardon my English, is it "jailbroke", "jailbroken" or "jailbreaked"?)