Yes, it CAN!! (It's called "slant drilling."
I'm in the business, son.
I know more about drilling, slant or straight, than you could accumulate in a lifetime.
They didn't need to slant drill.
They share the same reservoirs!
Oh, yeah, I'd forgotten that they are actually the same resevoir on both sides of the border. When it's the same resevoir, what does it matter where you drill the hole?
Kuwait was never stealing oil from Iraq. Even if they were, by your own arguments, the Iraquis were the aggresers, and did horrible things in Kuwait.