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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