Today there was some buzz about a battery bug in the iPod classic. Since perceived bugs aren't always universal, or even widespread, we like to wait a bit before sounding the alarm. Well, this afternoon, when I plugged in an iPod classic that I swore was close to fully charged and saw the "Connect to Power" error message you can see above, I decided to dig deeper.
Sure enough, many, many classic owners are experiencing troubles. On this Apple Support thread alone, 33 posts discuss the issue, with speculation about whether the cause is use of Cover Flow or even leaving the clock display on (for as long as it lasts) when music isn't playing. Most people say the problem hit when they upgraded to 1.02, the supposed classic "fix."
In my own circumstance, the cause couldn't be Cover Flow, because I rarely use it. (Sorry Steve!) It could definitely be related to the 1.02 update, as I had no problems until I updated. If you haven't updated to 1.02, you may want to hold off. If you have, some people recommend restarting it to get it out of its continuous battery-draining spin. Some people simply recommend taking it back to the Apple Store for a replacement.
Over the next few days or weeks, I will be paying careful attention to the classic's power consumption, and I encourage you to comment to this post if and when you experience similar issues. And Apple, I know you're listening: if, as we presume, this is a software problem, please fix it before thousands of poor bastards try to take their classics back to the shop. [Apple Support, iLounge Forums]