A while back my friend Jeremy told me about a little tool he used for importing music from his iPod into his iTunes library called Senuti. He mentioned it as a way of getting around iTunes content DRM issues. When you buy media from the iTunes store, the DRM it comes with will only allow you to transfer it a certain number of times before it disables it. Well, I’ve transferred my stuff enough times that I was beginning to worry that I might be getting close, and I had a need to transfer my stuff again, so I decided to take a look at Senuti.

So, since I got my MacBook Pro, I’ve sort of put off the task of trying to get all of my media transferred to the new laptop. The idea of backing up my iTunes library on my old PC laptop, and then importing it all (over 15GB worth of data) over the network into my iTunes library on the new laptop just did not sound appealing at all. So then I remembered about Senuti, and how it would let me import everything directly from my iPod. My only question was whether or not it would have any issues with the fact that my iPod was formatted for Windows and not a Mac. According to the FAQ, there had never been any reported issues with this. Apparently it would work just fine with Windows formatted iPods. Sweet! So last night I gave it a shot. I was very pleased with the outcome.

So I downloaded and installed it (have I ever mentioned how much I LOVE how dead simple it is to install/uninstall software on a Mac? Maybe a post for another day…). I opened up iTunes and turned off automatic syncing. I followed the QuickStart and got my iPod plugged in, and I was off. One thing that the QuickStart didn’t mention: when I got my iPod plugged in, iTunes recognized it…it didn’t start syncing, but what it *did* do was start analyzing all of the content on it (not sure what that means exactly…I don’t really know what it was doing, but the iTunes status window kept saying that it was "analyzing" all of the content on the iPod). I had to manually put a stop to that (clicking the little "X" at the right side of the status window in iTunes did it). Once I got that stopped, I clicked the "Library" item for my iPod on the Senuti navigation bar, then clicked the big green down arrow "Transfer" icon up on the toolbar, and I was off. About 20 minutes later, all of my content, music, TV shows, Audiobooks, everything, had been transferred from my iPod into my iTunes library on the new laptop.

After that was done, I was able to "Reset" my iPod, which basically reset it to factory condition and got it formatted for my Mac. Once it restarted, I had a fresh iPod ready-to-go on my Mac, and I was able to transfer all of my content from my iTunes library *back* onto the iPod. Again, about 20 minutes later I was all done. Thanks Senuti for making my life easy…and thanks J for the tip.