My husband crossed a boundary

I know this sounds weird but my husband is too generous. I asked him before we got married to not put anyone or anything in front of his family (in addition to one other request). I consider this a boundary and he has now crossed in a huge way- twice. Maybe I should not be upset because essentially no one was physically harmed by this? But last time this happened he could have ended up in jail and family ended up helping with $6000 plus in legal fees. I just don’t understand why he doesn’t get it. I don’t understand why he is always trying to put other people’s needs ahead of his family. He states this is not intentional… but what next? I actually lose my husband? Most of the time I catch him and say ‘no’… but this time I did not catch it. He says he did not understand or catch my ‘no’ on this one. But he gets mad at me for being too blunt- but he does not understand unless I am blunt. I don’t know. I feel like I should be more specific here, but I don’t know what else to say.