I was having that same problem today, but "syncing" with iTunes would most likely erase the iPod, wouldn't it? I believe it only syncs in one direction: from iTunes to iPod. I believe this is so you can't "smuggle" music from one iMac to another. However, I legitimately need to get my music from my iPod to my iMac. Drat.

Sincerely,
iScrewed

iTunes is programmed to mirror the contents of its library onto the iPod. This means that if you have no music in your iTunes library, it will completely delete your iPod. I recently ran into this same problem. There are, thankfully, a large number of third party applications that allow you to bypass this limitation. I downloaded iPod.iTunes. This application actually checks your iTunes library and if there are any duplicate tracks on your iPod it doesn't move them to iTunes. Worked flawlessly for me. I was able to move all my music from my iPod to iTunes. Anyway, if you type iPod in versiontracker you will find any number of applications that will let you perform this function. Make sure you read their instructions carefully so that you don't end up erasing your iPod. By the way, you cannot mount your iPod as a hard drive and copy music to iTunes. When the iPod is mounted, it doesn't show any of the music files in the finder.

If you have access to a PC machine I have an easy fix. The same thing happened to me. Luckily the restrictions apple put on there so you can't copy the iPod songs to other songs don't work on windows. connect your ipod to your mac. Enable file sharing for windows. From a PC mount the iPod and mount the HD you want to copy the songs to. On the PC you will be able to see the hidden files that you cannot on the mac. Simply drag them from the iPod to the new HD. **Note** When I did this, I actually moved the files from the iPod to the PC and then copied them to the mac, but I don't see why it wouldn't work, skipping that middle step. Mounting the drive from the PC gets you access to files that are hidden, which i believe is the only thing you need to bypass.

Use xPod it automatically will export your all of your songs onto your hard drive and then you put them into the iTunes library they will be organized in the library becasue the tags ID# tags will be OK. A while I go I accidentally screwed up the partition on my iPod and had to back it up so i could reformat it.

Make sure you have enabled root access by going to NetInfo Manager in your Utilities folder. In the menu, select Security and Authenticate. Then select allow root access and reauthenticate. Next open terminal, and type su <return> and your password. You will now be in root mode so be careful. Type cd .. <return> and keep going until you are at the root of your drive. At any time, type ls -al to see a list of files (hidden and visible) contained in that folder. Then type cd ipod and navigate to the music folder. You should see a list of folders called F01 to F20. Each is a folder containing hundreds of Mp3s. From there, just cp (copy) any file you wish to your desired destination folder on your hard drive. I would consult some general help in terminal on the actions: pwd, ls -al and cp. Good luck.