I have heard of Apple letting you re-download your music but you have to contact support, give them a good excuse and they will only do it once. Here is my email to them (trying to sound like “normal” user so they take pity on me).

I bought this brand new MacBook Pro after my Windows machine cratered about 2 weeks ago. I had all my music on an external hard drive. After connecting to my new Mac, I was able to load all the files into iTunes fairly painlessly.

The irony is that I wanted to setup Time Machine using that hard-drive as the backup device but I had to reformat. So I went to copy all the files to my local drive. What I didn’t notice was that the copy would be to big for the partition I was coping to until after it had already started, so I stopped. Not completely up on Mac usage pardime differences, I didn’t notice I was actually doing a “move” and not a “copy”, until I noticed half my files were in on the local drive and the on the external drive. Used to how Windows works, I knew that dragging the one folder to one of the same name in a different location will merge the contents of those folders, but on Mac that actually means deletes the destination folder and replace it with your source folder. (ARGGG!!!)

I though it was going to somewhat ok because I had my favorite music still on my iPhone and I knew I could pull it off there. I plugged it in but I had not associated it with my new Mac. I did so and then “backed up” in iTunes just to be safe (which turns out is not really a “full back up” like it says but just copy of the settings), and synced then I synced it up (copy purchases from iPod menu was no where to be found like remember from my iPod back in version 6). It then deleted everything on the iPhone and tried to resync from scratch.

I have lost nearly all the music, movies, tv shows, and audiobooks I’ve purchased since 2005 (everything I had before then is still on my old iPod Photo).

Can you allow me to re-download my purchases, or offer any tools that will help recover files on a FAT formated drive from the mac?

Lets see if this works :-)