iTunes 10 Forum

I'm a recent Linux convert from windows, but I own an iPhone and an iPad. I've tried wine in the past and crossover. But neither worked with an updated version of iTunes. I just recently saw something on YouTube about crossover9, so I got all excited. Now I'm disappointed again because there is no syncing ability with the iPhone & iPad. I would gladly pay whatever price if I can just get that ability with crossover. I hope there's an update soon so that I don't have to keep rebooting into windows just to sync or update my devices. And I really don't want to have to overpay for a Mac.

syncing music with iPod may work with other Linux utilities but will likely never work with iTunes through wine or crossover. There are two reasons for this. One is that Apple keeps updating the product, making it a moving target. And that Apple frowns upon messing with the syncing with ipods and iphones as the constant update war that occurred when the palm pre synced with the iphone.
Secondly getting an USB device to talk to a program running through wine requires more than just the program running. I've asked this before I am still unclear about what is what, but apparently you need to make a shim or a type of bridge driver in linux that will translated for a windows driver.

I did ONCE get my iPod nano 5th gen to sync with iTunes 9.

My tip is to install every iPod, iPhone and iPad tool that runs under windows in the same bottle, then try it out. WinAmp worked for my iPod and for my friends 4th gen nano, but iTunes hated my iPod and wiped it clean.

I don't know exactly what I did, but I had installed WinAmp, and no sync, then installed iTunes 9 and hey presto, both (with some disgruntlement) synced my pods. I tried it again, and it just wouldn't work again.

All you can do is fiddle.