Hi folks,
I'm also having this same problem, and have replicated this issue on my brand new Gen5 Nano (using iTunes 9.0.1 and Gen5 firmware 1.0.1).
Having spent the better part of 12 solid hours on this 😟 I confirm that:
1) This manifests with the iPod synchronising properly, but then when coming to disconnect, it gets stuck on the "OK to Disconnect" screen.
2) When the iPod is forcibly removed, the OK to Disconnect screen remains, and the iPod is unusable until a Reset and Restore is performed (Reset with Menu+Select; Disk Mode with Select+Play; Restore with iTunes).
3) This only seems to appear when when synchronising Smart Playlists that have Live Updating enabled. Any normal playlists, or Smart Playlists without Live Updating are fine. Additionally, manually managing music works fine.
4) I've also seen this coupled/exacerbated with an intermittent/unpredictable Windows dialog that says "There is no disk in the drive. Please insert disk into drive X (where X is the drive letter of the iPod)". Cancel/Retry/Ignore. This appears to be quite a widespread occurrence (
http://www.google.co.uk/search?q=nodisk+in+drive+erroripod).
When this disk issue happens to me, Cancel is the only option that doesn't crash both iTunes and the iPod. For me, Disk Mode exacerbates this problem: if it's enabled, this error will cause both iTunes and the iPod to become totally unresponsive (requiring Reset/Restore as in 2) to restore functionality).
5) So the workarounds that I've pegged down are not to use Disk Mode or Smart Playlists that have Live Updating.
6) It looks like the Smart Playlists issue is something that this wide-ranging with other iPod models - the Touch and iPhone also appear to be experiencing problems in these areas (see their respective boards on Discussions).
This is not the first time we've had problems with Smart Playlists. I've discussed this previously with Apple:
http://discussions.apple.com/message.jspa?messageID=1514307#1514307 and this appears to be an iPod firmware not hardware issue (as a few of you have reported here, replacement iPods behave identically). This is also not the first time we've seen problems with iPod firmware (
http://discussions.apple.com/message.jspa?messageID=613087#613087). I've worked with Apple Level 2 Support on these two legacy issues - and am going to see if I can get in touch with the same Level 2 folks again, to see if I can get this flagged for attention.
Any further opinions/examples/discoveries would be useful. One of the biggest problems it seems is that the latest (Gen5) iPod software does not recover once it crashes and is reset. Resetting causes the iPod to become frozen on the Apple logo - necessitating Disk Mode and a Full Restore to bring functionality back. When previous iPods crashed, a reset would bring them back to the main menu. And my Gen4 Pod works fine with iTunes, and doesn't experience any of the above, so it appears to be specific to the latest Pods/firmwares with iTunes 9.0.1.
Cheers,
Gopha.