Comment by jstummbillig

How about "Why does sshd not work?"

You are hinting that it doesn't. You are not suggesting that you know it should, or why, even if they can't give you a good answer. You are also not assuming that they don't know.

It's easy enough for the other party to come up with some mediocre reply to save face. That allows you to further assess how perceptive the other party is to receiving assistance. For example some version of "I tried that at some point, didn't work" would probably lead to me backing off respectfully. Any "why/how" question and we can take it from there.