Apple has never been Free Software friendly with their iPod. The whole business is based on the vendor and application lock-in of iTunes.

But this time it is apparently worse. Apparently Apple has decided that the database file for the song has to be validated with some cryptographic hash, or it appears to be. If the hash is not valid, the iPod refuse to playback any music (source). Read also BoingBoing's Cory Doctorow rant. This make gtkpod, Rhythmbox, Amarok and all these fabulous tools no longer working with the new devices.

How long before it get cracked? No idea. But one thing is sure. If you use Linux, don't buy an iPod. If you use OpenSolaris, don't buy an iPod. If you use BSD, don't buy an iPod. If you don't like this way of doing things, don't buy an iPod. I'm actually surprised that this didn't happen sooner, or maybe I'm like seeing too much evil or a giant conspiracy in what is an implementation detail...

Update: Lennart remind us some facts. I guess I might not be that wrong.