Ok, I have an old iPod (10 GB dock connector) purchased in 9-2003. For the most part it works great. Last night I downloaded some music from iTunes and I get this message when I hook up my iPod to update it: The music I just purchased will not go onto the iPod. So, I checked the software on my iPod and find that I've got v. 2.2 on it, but I need 2.3 according to the site. I download the iPodUpdater2005-11-17.dmg and clicked through the files. My OS is Mac OS X 10.3.9 (7W98), so everything should be hunky dory right? Well, I start to run the updater and I click through it, get through the Intro, Read Me, License, and Select Destination. At this point it says that I'm custom installing onto my mac, but it won't let me check the boxes for the iPod Updater 2005-11-17 or System UI Server (whatever that is). It says the action is disabled. The only button on the bottom available is "Go Back". Apparently I'm supposed to update the software on my iPod, but I'm not being allowed to. How can I update the software when it won't allow me to do it? I would really love to throw that music on there asap. Anybody have any suggestions or ideas on how to fix this problem?