IPod Classic 120GB cannot sync, "Required disk not found"

Question

Somebody, please help! iPod Classic 120GB charcoal, current OS as of about a week ago (won't stay synced long enough for me to see what it is), iMac 24" 10.6.4, iTunes 10.0.1. Let me know if you need any more info and I'll try to provide it.
Everything was absolutely fine until I updated to the newest version of iTunes. Now, when I plug in my iPod, it says it's connecting then jumps straight to the "Okay to disconnect" screen. It never shows up in iTunes at all. After doing this repeatedly, I unplugged it then immediately plugged it in again before it had finished the progress bar on the "Okay to disconnect" screen, and it finally showed up in iTunes, but it gave me an error of "iPod was not properly disconnected" then "cannot sync - required disk not found" and disconnected itself again.
I tried resetting it (menu+center buttons) while it was plugged in, and this did nothing. iTunes still didn't recognize it at all.
About a week ago, I followed some instructions somewhere and toggled the "enable disk use" option (I usually keep it unchecked) then was able to restore it. The songs were added back in a bizarre order (not alphabetical, not chronological, songs within an album added out of order, jumping from artist to artist, etc.) and I had to sync it again for three random albums that it missed the first time, but once everything was in again it was fine. I haven't added any new songs or playlists to my iTunes library since then (just changed a few ratings and I like to keep track of play counts), but when I tried to sync it again this morning, I got exactly the same errors.
The only difference this time is that it alerted me that one song in my library (a song I happen to like very much) could not be synced. The song still shows up on my iPod, but will not play. It still appears and plays in iTunes on the computer.
The iPod works perfectly in day-to-day use and is a little over a year old. I take very good care of it (my previous iPod is four or five years old and still works fine) and it has never had any problems before this. It has almost 100GB worth of music (no other media, just music), which makes it pretty annoying to have to restore it more than absolutely necessary. What is going on here and is there some way to fix it that will last longer than a week?

Answer 1

Hi, yeah I'm experiencing the same issue as everyone else with a 120gb iPod classic using iTunes 10.1.1 (4). Started about the time of OSX 10.6.5 update and hasn't been resolved with the OSX 10.6.6 update.
iPod attempts to Sync but now quits without even appearing on the computer let alone iTunes.
I have ESET security but quitting the app doesn't help.
I also have an iPhone 3Gs and that's still syncing fine (thank heavens), via a different library.
I've since managed to wipe the iPod clean (back to factory settings) as forced to do so by following the instructions in another post to remove the iPod Photo Cache. I then moved my iTunes folder to another directory for safe keeping.
I set up a clean iTunes database thinking my old one might have been corrupted. To do this you open iTunes from scratch while holding down the option key and select "Create Library". iTunes then remembers the last library created whenever you open the app.
When I am able to see the iPod summary screen (a rare occurrence now) I see that "enable disk use" is checked ok - this has been noted as a problem in previous forums. So that's not the issue.
Actually the iPod doesn't even stay connected to my 2010 unibody MacBook Pro when the iPod is switched over to disc mode. It immediately goes into "OK to Disconnect".
So I now have a clean iPod, and clean iTunes - all empty and essentially useless!
Anybody out there with any ideas? Plllleeeeeeeese?