Q: When I try to sync podcasts to my Nano, iTunes freezes

Same issue here but I'm getting this on a Mac, and not just with podcasts. Any manually synced content (songs, photos, etc) for my 6th Gen Nano cause this hang. This is a new problem, everything used to work fine, but I have since updated iTunes (I am also at 10.6 for iTunes). I do *not* get a hang if I just use the default settings where iTunes automatically fills in as much music as it can. Then I get normal sync behavior and the sync animation shows on the Nano screen. But if I try to custom sync any content, iTunes hangs and the Nano screen simply displays the "Connected" screen.

Going to try to roll back the version of iTunes.

MacBook Pro 10.6.8

iTunes 10.6 (40)

iPod Nano 6th Generation 8GB

Problem solved. Rolling back to iTunes 10.5.3 fixed this and restored normal behavior to the sync process. This would seem to corroborate the idea that this issue is the result of some sort of problem with iTunes 10.6. Here are the steps I took to rollback to the previous version of iTunes:

• Download the appropriate version from this page and install (but don't launch iTunes yet). The availability of this installer is time sensitive, of course.
• Assuming you have already used iTunes 10.6, there is a file called iTunes Library.itl that iTunes creates and you will need to either delete it (if you don't care about losing your playlists) or replace it with the last version in the "Previous Libraries" folder (assuming you ran iTunes 10.5.3 before this). Just move the last version from the Previous Libraries folder (it will probably have a date in it's name), put it in the same place as the original file and rename it to be iTunes Library.itl. These files are located in /Users/username/Music/iTunes/ (for Mac OS), or \Users\username\My Music\iTunes\ (for Windows 7). More info here fo other Windows OS's.

Once the iTunes Library.itl file is dealt with you should be able to launch iTunes 10.5.3 successfully.

Worked for me.

I'm having the same problem, but when I try to install 10.5.3 I'm told that I can't because a new edition of iTunes is already installed on the disk.  Any ideas?  Thanks.  I'm using OSX 10.6.8 on an iMac 11.3

Yes, I should have included in the first step above that you need to delete iTunes prior to installing it. On a Mac this means going to the application folder and moving iTunes to the trash (you'll need to authorize this with an admin pw). On a PC refer to this page.

I use auto-sync with only checked songs and podcasts. I don't think it's any slower than manually dragging the tracks I want to the iPod.

I actually have the same issue, except that the Nano syncs just fine when I manually swap out songs (I have "Manually manage music and videos" checked, and I click and drag music and audiobooks). But if I don't check that, and try instead to manage audiobooks and songs by checking boxes (under "music" or "books"), iTunes (10.6, build 40, 64-bit mode) freezes, and none of the changes are made.

I am running version 1.2 of the iPod OS, and I did not have this problem until I upgraded to iTunes 10.6.

CHF

THANK YOU SO MUCH dougmc!!! I just downloaded a bunch of new music and I was so bummed that I was having a hard time syncing...thanks for putting so much effort into your troubleshooting steps! I needed the 64bit version of iTunes 10.5.3, which I found here:

http://support.apple.com/kb/DL1427

This solved my problem! Thank you!

This fixed me up, too!  Thanks! 

I can't delete iTunes 10.6.  I get a message saying it cannot be deleted because OSX requires it.

So... any other way to backdate to 10.5.3?

This article may be helpful, thanks to the good folks at osxdaily:

http://osxdaily.com/2012/02/06/delete-itunes-mac-os-x/

I had the same problem with my 6th generation ipod Nano. Rolling back to 10.5.3 took care of the problem. I remember a time when Apple stuff just worked without hassles. I hope that this is just a tiny glitch and not a future forecast.

I also had the same problem with my 6th generation ipod Nano. Rolling back to 10.5.3 took care of this problem and also of the sudden slowness my PC seemed to experience now I look back. Hope the next update will be according to the high standard Apple normal delivers.