I just try to reuse the same woodruff key until it is really gouged up and jammed in there tight, as well as keep a few spare woodruff keys in my wallet.
The key slips a little, you clutch and the gear breathes a little, then accelerating vibrations unscrew the screw like a mini hydraulic. When I get a replacement screw I'm gonna locktite that key because I think that's what's caused it. #purpleLocktite
Still haven't found an m8x1t screw, trying another Hardware shop later today.
Everybody breaks a bike differently the moment they sit on it, also tho - only so many things can happen.