Planning to pick up a new iPod Nano/Classic/touch? You might want to re-think that purchase if you are a Linux user, as the latest models break support with all of the popular iPod synching applications. This was done due to changes in the iTunesDB, which likely means that it can be reverse engineered, just as previous updates have been. Did Apple do this on purpose or was this an actual feature update? Good question.
I have been throwing the idea of purchasing an iPod touch later this month, but this news definitely sideswiped it since I use Linux full-time. Is Apple trying to force people to their OS? If so, breaking iPod support is not likely going to do it. If people are willing to make an OS switch because of a music player, then kudos to them. I think it’s about time that Apple realizes that Linux is going nowhere and begins supporting iTunes under the OS, or even better, stops breaking support for other applications in general.
At the very start of the database, a couple of what appear to be SHA1 hashes have been inserted which appear to lock the iTunes database to one particular iPod and prevent any modification of the database file. If you try to do either of these, the hashes will not match and the iPod will report that it contains “0 songs” when the iTunesDB would otherwise be perfectly adequate.
Source: iPodMinusiTunes Blog