When my NAS recently died, it took (among other things) our music collection with it. Luckily, I had a full backup from three weeks ago, so I recovered 99% of what we had. But, those missing three weeks were three busy weeks for music purchases. I had two records from Anita O'Day, the new Beastie Boys, Dirty Projectors, Old Crow Medicine Show, and many others that I couldn't remember.
Then I remembered that most of those new songs are on my iPod, so they weren't lost forever. But, as I recalled, plugging an iPod into iTunes starts the sync process, which would sync the iPod with the old iPod playlist, which didn't have the new stuff, which means those new songs would be deleted. Can't do that! So, I found an program that could take songs off an iPod and import them back into iTunes. All I had to do was find the songs I bought during the lost three weeks and click a couple of buttons. Simple! Except, I forgot all the things I'd purchased. I got most of them, but knew there were more... After racking my brain for a while, I gave up and decided I'd just have to repurchase anything I forgot to save.
So... Did all that, plugged the iPod into the dock and iTunes popped up a box that said "Hey, looks like there are some songs on the iPod that aren't in your library. Do you want me to add them to your library for you?" Fuck yeah I do! Finally, when confronted with an exceptional situation, iTunes does exactly what a normal person would want it to do! Thanks, Apple!

Thanks, Apple!
*faints*
Holy crap! Not that this erases the Fucking Goat Shit assessment, but still, nice to give credit where due.
It only took like 11 versions for them to get this right.
I don’t have an iPod because I am allergic to Apples (and I am a Cowon fanboy) but my daughter does. We turn off the auto sync first thing and do all the syncing manually. I just don’t like the loss of control when a device wants to do things all on its own.
It’s great that iTunes is finally doing this but I wish I could get the unholy piece of crapware off my computer once and for all. Might be time to convert the kids to Sansa or something (Cowon is a bit pricey for kids).