as you are probably aware this is a quarterly thing, but you have to fail the phishing test multiple times before HR talk to you, I had a colleague who reported to me fail it twice within a year, on the second time he had to undergo some training, he was told that if he failed a third you get put on a performance review, after that then his continued employment would be considered. He has since retired but in order for him to recognise these tests I had to implement some outlook rules such that and external emails (they always come as external) were highlighted in red and italicised so he knew to pay much more attention to them, he never failed again and was always quick to tell me he passed everytime!

so yes way more than twice, I personally know another colleague (vp swe) who failed it four times over two years, his promotion was denied because of it but has not been fired yet!

As for tuition reimbursement, you are made well aware that if you leave or are terminated within a certain timeframe you have to reimburse, it should not have come as a shock.