Transfer of IPOD Tunes to New Mac Book

Question

Prior to purchasing a new Mac Book and IPOD (80 Gig), I ripped my entire CD collection using ITunes to my old PC. Connecting my new IPOD to the PC, I then sync'd the entire ITunes Library to the IPOD. Upon purchase of the MacBook, I attempted to "sycn" from the IPOD to the MacBook but received a message stating that in order to sync, my IPOD would have all its current tunes deleted. All the ripped files were extracted from legitimate CDs but Mac, I believe, assumes the library on the IPOD is not legitimate. Could someone offer a suggestion on how I can transfer the entire contents of my IPOD to my MAC Book? I am a "tecno peasant" so simple explanations would be greatly appreciated. Thanks.

Answer 1

Connect your iPod to your computer. If it is set to update automatically you'll get a message that it is linked to a different library and asking if you want to link to this one and replace all your songs etc, press "Cancel". Pressing "Erase and Sync" will irretrievably remove all the songs from your iPod. Your iPod should appear in the iTunes source list from where you can change the update setting to manual and use your iPod without the risk of accidentally erasing it. Also when using most of the utilities listed below 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
Once you are safely connected there are a few things you can do to restore your iTunes from the iPod. If you have any iTunes Music Store purchases the transfer of purchased content from the iPod to authorised computers was introduced with iTunes 7. A paragraph on it has been added to this article: Transfer iTunes Store purchases using iPod
The transfer of content from other sources such as songs imported from CD is designed by default to be one way from iTunes to iPod. However there are a number of third party utilities that you can use to retrieve music files and playlists from your iPod. 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. This is just a small selection of what's available, you can also read reviews of some of them here: Wired News - Rescue Your Stranded Tunes
Senuti Mac Only
PodView Mac Only
PodWorks Mac Only
iPodDisk PPC Mac Only (experimental version available for Intel Macs)
iPodRip Mac & Windows
YamiPod Mac & Windows
Music Rescue Mac & Windows
iPodCopy Mac & Windows
There's also a manual method of copying songs from your iPod to a Mac or PC. The procedure is a bit involved and won't recover playlists but if you're interested it's available at this link: Two-way Street: Moving Music Off the iPod
Keep your iPod in manual mode until you have reloaded your iTunes and you are happy with your playlists etc then it will be safe to return it auto-sync. I would also advise that you get yourself an external hard drive and back your stuff up, relying on an iPod as your sole backup is not a good idea and external drives are comparatively inexpensive these days, you can get loads of storage for a reasonable outlay.