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The most chaotic good thing to do would be to use the known security issues to hack into your boss' computer in the most scarry looking but harmless way. That would possibly scare them into upgrading.
With that said, you should create a paper trail on how you warned your boss, and either wash your hands of the issue or kick it up the chain, depending on how much you care.
EDIT: since it seems some people didn't get it, I meant the first option as a joke. My actual advice is the second paragraph
More like chaotic dumb. This is a good way to get fired and possibly end up with criminal charges depending on how petty the boss is. And based on how stubborn and tech illiterate they are it is likely.
I didn't actually mean the fist option, it was meant as a joke. I clarified it in another comment, maybe I should just edit the original one.
Yes! There is a website somewhere that has a tonne of fake os screens - updating/upgrading windows, bsod loop etc.
Run a scary looking one of those, disconnect mouse/keyboard so it can't be interrupted and let the boss discover it
Just be be clear, I wasn't advising OP to do the first idea. It was more of a joke. It has potential to be traced back and get him into trouble.
As a user at a big company that needs to lock down its security, we get quarterly phishing emails that would tell you that you failed the test so to speak if you click the link. It shows how easy it is to everyday users of how easily an entire system can get compromised.
Having a "test" like this might not be bad if you run it by boss first?
As far as I understood the problem here is OP's boss, so I don't think that would be a feasible solution in this situation