I have Pippa in a playpen, pee pad on one side, bed on the other. She uses the pad consistently. If I put her in a crate at night I am sure that at this point she would not hold it because I give her free access to her pads...KWIM? Maybe you are using two methods (pads in the day, crate training at night) and he is not ready for that, he is kinda young still...