If it happens that often then iTunes isn't communicating clearly enough to the user what is about to happen. I'm reminded of this advice:
> The principle is simple: it's not your fault. (Side note: if you don't understand this reference, then do yourself a favor and watch this video[1].)
It's not your fault. It's not the user's fault. It's not the designer's fault. In fact, it's nobody's fault. What's crystal clear to you might be confusing to me, and no one is to blame for that. It's just something we have to work with. — Source: http://moz.com/blog/5-lessons-learned-from-100000-usability-...
> If it happens that often then iTunes isn't communicating clearly enough to the user what is about to happen.
Yes, I agree completely. But given that, I have to say I hear regularly from people who (a) buy a new iPhone, and then (b) wipe their music collections later on the same day.
Many people assume that an apparently sophisticated, polished program like ITunes will "do the right thing." But no.
> The principle is simple: it's not your fault. (Side note: if you don't understand this reference, then do yourself a favor and watch this video[1].) It's not your fault. It's not the user's fault. It's not the designer's fault. In fact, it's nobody's fault. What's crystal clear to you might be confusing to me, and no one is to blame for that. It's just something we have to work with. — Source: http://moz.com/blog/5-lessons-learned-from-100000-usability-...
[1] http://www.youtube.com/watch?v=dfXpRn8uFL8