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by tim333 592 days ago
In 2001 an S200 missile fired at a drone during a military exercise missed the drone, saw an airliner 160 miles further away and went and took that out. Not sure if that counts?

No one actually told it to go for the airliner but it kind of took the initiative. (https://en.wikipedia.org/wiki/Siberia_Airlines_Flight_1812)