It gives you a pop-up warning though? It's entirely non-obvious from a UI perspective that you need to right-click on the device and choose 'transfer purchases

It gives you a pop-up warning though? It's entirely non-obvious from a UI perspective that you need to right-click on the device and choose 'transfer purchases' though. I had thought this was incompetence on Apple's part (specifically the iTunes team) but perhaps it was a semi-deliberate broken offering to prepare people for iCloud?