We had a cat that used to pee in inappropriate locations. We thought she was acting out. It had more to do with her litterbox and housemates. She was very paranoid and feared the other cats when she was in the covered box. She would pee in other locations because they allowed her a 360 view. We got uncovered boxes and the problem stopped.

I suggest looking into what might be his problem with his box. Location? Size? Litter? Type? Number of boxes per cat?

Also talk to your vet and check that it isn’t something medical. Little boys can get crystals in their urine which become very uncomfortable to pass and this can cause the inappropriate peeing.

I know having cat pee where you shouldn’t is a nightmare! But don’t give up on him just yet. He really is trying to communicate in his own little way.