Used to shoot a .22lr Remington semi-auto. Could hit soda cans at 125 yards more times than not and hits from 250 yards were possible. That made me curious. I started incrementally shooting further and further away at targets.
Longest shooting was 476 yards (tape measured) (with hits). Target was a piece of stovepipe (hits were faint but audible) about 1 yard high and 8 inches across with a paper target fixed to it. Was shooting from a hybrid position to see over the weeds and stay out of the snow (squat with arms supported by legs) I could hold that light 22lr really well from that position, but I also remember that little gusts of wind would move me. Hits were not as common as misses, probably about a 5 to 10 mph wind (waited for calm before letting the shots go), about 6 hits out of 20 if I remember correctly.
I was using a 4X BB-gun scope, had to hold the target in the very bottom of the scope, with the thick line just to the right for windage. That put the cross-hairs around the top of a cliff on a hill behind the target.
Tried as far as 540 yards, but the vertical spread was ridiculous (shallow snow over sandy dirt made inspection possible) and the target was not visible with my setup (had to aim at a point on the hill above the target)!
That was long ago, and that .22lr was my only rifle at the time. After that I started memorizing ballistics tables and dreaming of long range shooting rigs