
I'd say that that's enough warning.
Ahh. Now delete the songs from outside of iTunes. Then try it. It’ll show no such warning.
When deleting files on a computer to free up space, one normally wouldn’t tend to go into each specific program alloted to the files to do so.
An explorer-type program is used usually, and using this is when those wonderful warnings don’t show up.
If the iPod’s interface had been a simple drag-and-drop, this process wouldn’t be necessary. Nor would the redundancy of storing the same files once in the computer’s drive and also in the iPod. When song archives go 40GB to 60GB, this is a real PITA to waste such large amounts of space. Especially on a laptop.
i disable the auto feature.... almost happened to me.