To be fair, iTunes suffered from the same defect at one point. Microsoft is now a clinic on defective design, execution, and attitude. But back then it wasn't that bad.

The iTunes case was also a classis UI 101 blunder combined with stupidity. If there was no iPod plugged in, the "Sync on connection" toggle in iTunes simply disappeared. First of all, when something is inapplicable, you grey it out. You don't just make it disappear.

But in this case, even greying it out would have committed the same blunder, because the default state for this behavior was YES.

So if the hard drive in your computer went bad and you installed the OS fresh on a new one, thinking that all your music was backed up on your iPod, you were right... until you plugged it in.

So, so dumb.

And finally: Apple never addressed the lack of "computer overwrites mobile" and "mobile overwrites computer," which Palm OS syncing nailed in the '90s.