itunes 9.1 and ipod classic sync is a mess!!!!!

You might try syncing the iPod to another computer. If it works, then you'll know there's an issue with your computer. Alternately, create (or log in under) a different user account on your Mac and see if the iPod will sync.

My Ipod Classic had the same problem after I updated to iTunes 9. I discovered it was a problem with the software version on the iPod; not so much iTunes 9. I think this is why only some of us are suffering this problem. The catch is, you need a successful sync to update the iPod software.

If you happen to have a second computer with iTunes 8.2 or earlier, you can use that, but if you are like 99% of people with the same version of iTunes on all computers, you need to rollback to 8.2, update the iPod, and then reinstall iTunes 9. It took me about 30 minutes to get my iPod classic working with iTunes 9 using the following steps:

1. Uninstall the iTunes 9 application as far as step 13 on this help file http://support.apple.com/kb/HT1224
(this will remove the application, but leave the music and your libraries intact)

2. Download and install iTunes 8.2. I found a site with an old version using a google search http://en.kioskea.net/telecharger/telecharger-241-itunes-for-mac

3. After version 8.2 is installed, start iTunes by holding down the OPTIONS key on your keyboard and use one click (don't double-click) on your iTunes icon (if it doesn't work, just quit iTunes, and try again...you will get it eventually). A window will pop-up enabling you to create a new library. Do that, and give it a random name (you won't use this library again).

4. iTunes will start (without any of your original library showing, but don't panic; it's still there), and your iPod should now connect. Choose not to transfer any files, or authorisation, however, take the option to update the iPod software.

5. Once the software is updated and has restarted, eject the iPod (no need to complete the sync)

6. Perform a normal mac software update to reinstall iTunes 9.

7. When starting iTunes 9 for the first time after reinstalling, hold down the OPTION key on your keyboard and use one click on the iTunes icon; pick the CHOOSE LIBRARY option. Open your original library that has all your music, and you should be back to where you want to be; your iPod syncing as normal. Next time you open iTunes, it will open to the correct library. The use of the OPTION key is only needed the first time.

8. Hopefully, stop banging your head against your desk.

Thanks Gregga34 - unfortunately that doesn't work for me and my 80GB iPod classic. What version iPod are you using? And how much music have you managed to sync with your iPod? Since being forced to restore mine in iTunes 9.0.2 I can no longer sync more than around 13GB of music. (Lots of people post answers on here but then say they've only added 500 songs...)

Hi citygirloutdoors,

I have a 6th Generation iPod Classic 80Gb with software version 1.1.2 in Macintosh format. When I read your reply I did a factory restore on iTunes 9, followed by a sync of all the data I could find to see what happened. It wasn't quite enough to fill it but came close.

The result is 18.49 Gb of songs (4153), 6.67 Gb of movies, 31.58 Gb of photos (about 8500), and 377.3 Mb of contacts and iCal events leaving only 17.26 Gb free.

Ah that's useful to know, thanks. Were you forced to restore your iPod with iTunes 9.0.2 or did you not get that far?

Unfortunately I suspect that's what is ruining iPods as if I hadn't done that then it should be working as before on downgraded versions of iTunes. But it's not. Am now trying to figure out what firmware I had before and if I can get back to that...

citygirloutdoors,

I restored the iPod to factory settings using iTunes 9.0.2 after I updated the firmware with a temporary rollback to iTunes 8.2.

Prior to updating the firmware, iTunes 9 couldn't 'see' my iPod, but now everything is working ok.