This particular dialog deserves a special place in user interface hell. It doesn’t win any points back for coming from Cupertino. It scores a couple for irony alone, that’s it.

If you use the latest, greatest version of iTunes and dare add some MP3s or videos to your iPod which can’t be played, or which are momentarily unavailable (external HD not connected) when iTunes wakes from its slumber, you will be delighted to meet this dialog.

What’s so bad? This baby is straight from Redmond. It’s an application-modal dialog that has an OK button. It’s got Aqua (ooh), it’s got an internal scrolling pane, but that’s it. Does it try to help you solve the problem? Nope. In fact, it seems to be going out of its way to make it impossible to solve, and I guarantee that if you see this dialog once, you’ll be seeing it a few times unless you’ve got a pen handy.

Unless you’re the “ignore this problem entirely” kinda person, that is. It does have a checkbox for that.

But if you want to solve the problem, then you might hope that this window would give you a few options:

Automatically fix these tracks. (Convert the tracks which can’t be played, prompt to find the tracks which can’t be found.)
Make a new playlist of these tracks, so I can re-convert them / delete them / fix ‘em up later
Just remove these tracks from the iPod […]