I don’t know about OP, but I remember reading and watching a lot of videos about blue hat hacker, whose sole job is to break things then report to secops so they fix it. They test everything including social hacks and physical ingress testing (getting in and out of a place they aren’t supposed to be in). One described their job as professional trespasser. The crazy shit they did was simple and could get them walking right into data centers without anyone noticing.