iTunes Auto Synchronize

1. Hold down the Apple + Option keys on the keyboard and don't let go.
2. Connect the iPod to the iBook.
3. When iTunes opens and the iPod shows up in the Source list, let go of the keys. You have temporarily disabled auto-syncing this one time.
4. Click the iPod in the Source list. And click the iPod prefs button on in the lower right corner with an iPod symbol on it.
5. Disable auto-syncing permanently in the window and you should be fine.

Everything was looking good, for the first few minutes anyway.

I followed the steps you listed, checked the iPod prefs, and it was already set to "Manually manage songs and playlists" and both options to "Automatically update" were not selected. I was able to see, and play, my music.

I let the iPod idle for a little while (maybe 5 minutes), and when I went back to it none of the songs would play in iTunes. I would receive a little exclamation mark next to each track that I would try to play. I then disconnected the iPod and tried to use it like I normally would. It just skipped over every track that it tried to play. The tracks look like they are there, but none of them will play, and a look at the properties of the iPod's drive shows that only 22Mb is in use.

So, although iTunes is not set to automatically update, I still lose all of the tracks when I connect my WiniPod to a Mac.

The files are probably still there. If you plug the iPod back into your Windows machine, they should read fine.

Several users have reported this kind of trouble when connecting WiPods to Macs. No one has ever figured out what the problem is, exactly.