Alright, this is going to be a little lengthy, but I want to provide all the information I can from the beginning. I bought an iPod Classic 160GB in February. I had no problems with it, until about a week in. At this point, I connected the iPod to sync it with my library and I got some error (I don't remember exactly what it was) that asked me to restore my iPod. So, I did that and re-synced it.. everything was fine. I synced it a couple more times and it worked fine.. then the next time I got the same error message. This became a regular thing, so after it happening 3 more times, I took it back to Best Buy and they replaced the iPod with a brand new one. I brought it back home and the same exact thing happened. This led me to believe it wasn't the iPod that was the problem, so I updated iTunes and tried to sync it without the Apple dock. Still, the problem persisted. I tried uninstalling, then reinstalling iTunes and I still have the problem. Now, I am syncing and it takes a while for iTunes to recognize my iPod, then when it does, it takes forever to sync it (when it should only take a few minutes depending on the updates I have made) and now it's going through songs that haven't been touched saying "iTunes could not copy (insert various song names here) to the iPod because an unknown error occurred (-50)." It has done this for about 10 songs already. The iPod works perfectly when it's not connected to the computer. I install my updates regularly. I am currently running OSX version 10.6.3 and iTunes version 9.1 (I installed the new update a couple days ago) on a Mac Mini (newest iteration) 2.26GHz Core 2 Duo and upgraded to 4GB RAM. After the process of elimination, I can only conclude that the problem lies somewhere in my computer/OS, but that is beyond my knowledge-base. Any help or insight would be fantastic. If you have any questions about anything I haven't included, please ask if you think it would help. Thanks so much!