Make:

With the new Nano, iPod Classic and iPod Touch devices, Apple altered the iTunes database slightly to include a cryptographic checksum, which immediately broke all third party iPod management software. Since there's no iTunes for Linux, this essentially meant that Linux users had to look for another solution for putting music on their devices. Great software like gtkpod and Amarok no longer worked.

This was a few days ago, and it looks like the hash used by iTunes has already been reverse engineered. Every time the database is updated--whether you change the name of a song file, or add or remove music--a new checksum needs to be calculated, based on the contents of the library and your device's unique ID.

Right now, you can continue to use your current software, and then generate and update the checksum in the database manually. No doubt that within another three days all of the nitty gritty details will be automated for you in your favorite open source iPod software.

Ian Monroe, makes this valid point, however:

Really the only "correct" solution is for folks to stop using Apple products. The iPod might have its own version of DAAP's iTunes 7 which has a checksum more difficult (apparently) to crack. But for the time being, things are fine.

Fifteen years ago, a lot of us started making the switch to Linux from Windows, even though the platform was a little foreign, took some work to learn, and was a bit crusty around the edges. The real catalyst was that Linux had a hell of a lot more to offer in terms of networking capabilities, a programmer-oriented free development environment out of the box, and a level of performance and stability that the Microsoft operating systems couldn't touch.

I'm not sure what the final motivating factor will be for people to switch to an open hardware/software platform for their mobile connectivity and media devices. The ability to use it with your preferred desktop OS--not to mention the ability to share your data between multiple devices and multiple desktop clients--is enough reason for me.

Making New iPods work in Linux - Link