For a while now I've been wishing I could replace iTunes with something on Linux and reduce my need for Windows. It would be nice if Apple would just release iTunes for Linux but I'M pretty sure that's not going to happen. The thing is, nothing handles an iPod as good as iTunes. I can't even play my audio books(.aax) from audible.com on a Linux machine at all. Last time I had Banchee as my Linux media player and had it running my iPod, a lot of really bad things happened. For starters, it started re-naming all of my songs to 4 random capital letters, something like this, TAGK, or XAZU, and also deleting songs from my computer completely. I didn't notice it removing songs because it wasn't removing them from my iPod. So when I transferred my music back to my Windows iTunes, my iPod was wiped out and re-loaded without all the songs that Banchee had been removing behind my back. Those songs weren't anywhere, not in my music folder and not in the recycle bin. Anyway, wouldn't it be easier if media players attempting to work with an iPod would just remove everything from an iPod and load one with it's own music software? I would think that that would be a lot less buggy than the media player(s) trying to work with the Apple software already loaded onto the iPod. Any thoughts or suggestions?

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First make sure you've installed the restricted extras package that supports popular audio and video formats such as flash and mp3, this can be found on the software center

now if you already have this, the media player I'd suggest you try is clementime, they have supposrt for external device storage such as mobile phones though I'm not sure about iPods, apologies if it doesn't work after all iTunes was born for this:)

Might I suggest that you take at Rockbox?
I have been using for 2 years, now.

Banshee and Amarok to name some others.

There are many great media players similar to iTunes, but plug-and-play ipod support is not always so great.

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