Usually when uncertain about something I'll try and approach it from several angles and batch up a number of questions to send them off in one go so that the person on the other end can answer them more easily and possibly gain extra insight as to what's amiss. But there are some people who are distracted and so when sent a list of five questions one of which is hard, they'll omit the answer to the hardest question... So with them I just resend a response with different wording and just that question. I'm usually not asking these questions of developers and instead communicating with stakeholders but yea, question weaseling is a thing, sometimes accidental, sometimes intentional, but it's good to resolve your question to a definite answer (including "I don't know")