My biggest pet peeve in iTunes is undoubtably how it asks you “Are you sure?” before doing anything, and always in an unhelpful way.
As an example, I mentioned to my wife a Christmas album I used to love. I spotted it in the iTunes Store and clicked Buy Album1. iTunes “helpfully” asked me:
This is a completely useless confirmation screen. If — and we’re talking hypothetical here — I considered $7.99 a big purchase and needed a confirmation screen for it, wouldn’t I want to know the price, too? Wouldn’t this dialog make more sense as:
Are you sure you want to spend $7.99 on an 80s Christmas album?
Really, you’re being a bit impulsive here. That’s cool, we’ll take your money, but we want to make sure you’ve checked with your wife first.
(Okay, not actually those words. But something involving the price.)
But instead, I’ll shake my head at the idiocy, of click “Don’t ask me about buying albums again,” and never see the warning again. What was the point, then?
- After discussing it with my wife, of course. [↩]

I know! I don’t use ITunes, but I have experienced that kind of thing elsewhere.
I find I usually just get in the habit of clicking YESYESYES all the time that I don’t even read them anymore.
What’s that called? Habituation or something…
It’s really bad in iTunes. A few months back I reset all the warnings and decided to get screen shots of all the stupid questions it asked me. I gave that up a week later, it was just too much work.