I would go by how well humans do it, which would mean: "yes, you can probably talk it out of it, but when it matters, that's hard enough to do in practice such that the human/system can be used for important tasks"

With humans it's just that the stakes are high because you cannot generally have a human at your beck and call like we do with machines in general. If you limited to 5 questions per topic and and overall use time limit, you might see different input still.

Cf. "Help, I'm a prisoner in a fortune cookie factory!".

Apparently something like this really does happen, although it continues to be hard to tell whether any particular instance is real:

https://www.businessinsider.com/chinese-prisoners-sos-messag...