Then he gets fired for hacking. And possibly winds up arrested for illegal activity.
It's a stupid idea.
Just send the boss an email that says what they spoke about verbally. That way if the system does get hacked, the guy has a paper trail to cover his own ass to show he told the boss.
Yes, but if any individual would fly a plane, I wouldn't be to shocked when most of them crash, but when a pilot is flying one, I'd expect him to land safely.
You understand that legally speaking this is approximately the same thing as telling your boss that the front door isn't strong and thieves could easily kick it in, and then when they refuse to fix it, the response you're suggesting is "show up at 3 am and take a sledgehammer to the door, but just dont steal anything from inside" right?
The point is to cover your ass, not pull your pants down.
Yes I understand the intention, but in one of these scenario's I've covered my ass legally and if something happens where the company gets ransomware for example, I likely get paid thousands of dollars in overtime restoring backups and the user ends up updating anyway, and in the other I can go to prison, lose my job, and never be able to use my time at that company as a reference on a resume let alone probably easily get a job again because now I have a criminal record.
I know this because I have lived scenario A probably 6 times in my life.
I know, I live those scenarios too, I said let some 4chan degenerate do the dirty work, get paid for fixing it and get your network in check - if you morally can't handle that situation because of the data, then do it yourself and you can ensure that your boundaries are not crossed.
Free pro tip: If you do it yourself, you still get paid to fix it ;D