Yeah, unless you’re particularly well equipped for that type of interaction, you’re unlikely to get any kind of satisfying outcome by asking them a question
Those sorts of people have a lot of experience gish galloping, rationalizing their own contradictions, and feeling smug about whatever bullshit response they give.
I don’t think their facade is impossible to engage with or break through, but it will always take more than one clever question to get there.
The chest in those rooms is always either a ring, an artifact, or a wand. It’s often the better option.