Doing The Prep Work
This may sound obvious, but before you begin, you will want to round up all of your iPods and their cords. iPods tend to accrue as we upgrade, so unless you traded in or gave them away, now is a really good time to find them. They may have hidden gems that you were not listening to (or watching) recently, that you do want to keep in your collection in general. While you are at it, dig up any old CDs you have with media you want to add to your collection or external storage (such as flash drives) with parts of your media library on them. This will lead to maximum restoration of your files.
Importing From Your iPod
Now, you can plug in your first iPod. When you do so, iTunes will open automatically and you should get a pop up window with your syncing options. Choose “Transfer Purchases”
If you are adding to a new system, or you needed a complete reinstall of the OS, you will have to re-authorize the computer. Choose “Authorize” and enter your username and password for iTunes. Remember, if you copy your songs back from a friend with similar music tastes, you will need to use their login to authorize and not your own.
The automatic transfer should happen now. Eject this iPod when the transfer is complete and repeat with any other iPods you happen to own. Note to iTouch users: In some cases, when a library was wiped but the software is intact, you may have to follow a bit of a different procedure. Once you plug in and open iTunes you will see tabs labeled with titles like “Music”, “Movies” and “TV Shows”. Check the box next to the word sync in each media category, then click on the button labeled “Sync” in the bottom right hand corner of the screen. This will sync your library to the system.
Importing From A Flash Drive
Plug in your drive. When it appears on your desktop, double click it to open the drive. Double click on the songs that you want. When iTunes opens to play them, a box will appear asking if you want to “Add to Library”. Click on “Ok” and your songs will import.
Importing from Your CD’s
I know, if you have an iPod, you probably don’t have a large CD collection, but get out what you do have and get ready to import. This will take the longest, and work only for your music, but it will get back things you cannot retrieve any other way. Insert your CD into the slot. If iTunes is not still open, it will open again and take you to the disks information. Click on the words “Import Disk” and the songs will be copied to your library.
There you have it, as good of a restoration as you are going to get from external media sources. If you had a real favorite that you just cannot restore, you should ask apple to let you re-download it. Just be ready to prove (with your digital receipt) that you own it, and know that asking is a bit of a shot in the dark. Sometimes it is a yes and sometimes it is a no, depending on how much you want to re-download and your proof. Next time, back up your files please.