It may be that because he knows you better, he can better predict what your reactions will be in the situation, and also he is more able to assess that this may actually be helpful, thus he is willing to work with the legal issue.

My analogy is with teaching a physical activitY, let's say yoga. I might not teach certain balancing moves that could cause injury to a new student. But after I know them, their abilities and reactions better, I might feel more comfortable with it, even if for other people I would still keep it off limits.

But of course, I think you should talk this through more with kashi.