Migrating from Windows to Mac, no loger have the Windows machine

Question

Hi All,
I have a two year old iPod that's pretty loaded. I originally had it set up with a Windows computer that I ripped all my CD's to. Since that point my Windows machine needed to be rebuilt so I lost all the iTunes stuff on it. I also recently got a MacBook Pro. Now I'd like to be able to use the iPod with the MacBook, but I don't want to have to reload everything onto it. So how can I take an iPod originally formatted for Windows and retrieve all the data so that when I plug it into the MacBook I won't lose everything. I don't mind if I have to wipe out the iPod and reformat it then reload the music. I just don't want to have to rip all my CD's again. If it's any help I do have a networked Windows machine available to help with this.
Thanks,
-Bruce
MacBook Pro   Mac OS X (10.4.8)  

Answer 1

Macs can read Windows formatting so you should be able to connect your iPod without any bother. You can use a keyboard command to prevent your iPod auto-syncing with iTunes. While connecting the iPod to the computer on a Mac hold down the Option and Command (⌥ and ⌘ Apple) keys. This will stop the iPod from auto-syncing with iTunes and it will appear in the source list. Wait until you are sure the iPod has mounted, and that it will not auto sync and then you can let the keys go. This may take between 20 to 30 seconds depending on your computer. Once you are connected change the update setting to manual so you can use your iPod without the risk of accidentally erasing it. Also when using a lot of the utilities your iPod needs to be enabled for disc use, changing to manual update will do this by default. Check the "manually manage music and videos" box in Summary then press the Apply button:
Managing content manually on iPod
iTunes Keyboard Shortcuts for OSX
If you have any iTMS purchases the transfer of purchased content from the iPod to authorised computers has been introduced with iTunes 7. A paragraph on it has been added to this article: Transfer iTunes Store purchases using iPod
The transfer of non iTMS content such as songs imported from CD is designed by default to be one way from iTunes to iPod. However there's a manual method of copying songs from your iPod to your Mac. The procedure is a bit involved but if you're interested it's available at this link: Two-way Street: Moving Music Off the iPod
If you prefer something more automated there are a number of third party utilities that you can use to retrieve music files and playlists from your iPod, this is just a selection. I use Senuti but have a look at the web pages and documentation for the others too, you'll find that they have varying degrees of functionality and some will transfer movies, videos, photos and games as well. You can also read reviews of some of them here: Wired News - Rescue Your Stranded Tunes
Senuti Mac Only
iPodRip Mac Only
PodWorks Mac Only
PodView Mac Only
iPodAccess Mac & Windows
YamiPod Mac & Windows
PodUtil Mac & Windows
iPodCopy Mac & Windows
Keep your iPod in manual mode until you have reloaded your iTunes and you are happy with your playlists etc. then if you wish it will be safe to return it auto-sync again.