(e) I say something that someone doesn't understand. I think "maybe the person needs more context," and follow up by giving more context. The person still doesn't understand, so I think "ok, I guess I have to give even more context" and so continue in the same direction. In fact, the amount of context that I would need to give for my point to be clear would take ~100 hours to convey, so that what I'm doing is actually not at all productive. The person perceives the situation as

Jonah is totally ignoring the fact that I'm not understanding what I'm saying, and keeps going on and on about the same thing, oblivious to my feelings

because he or she has no way of knowing that I'm explicitly trying to address the fact that the person is uncomfortable about not understanding.

Oh. Well. Oops.

But what alternatives are there? Should I just give up? That seems rude too.