This is kind of fascinating because I just tried to play mussolini or bread with chatgpt and it is absolutely _awful_ at it, even with reasoning models.
It just assumes that your answers are going to be reasonably bread-like or reasonably mussolini-like, and doesn't think laterally at all.
It just kept asking me about varieties of baked goods.
edit: It did much better after I added some extra explanation -- that it could be anything that it may be very unlike either choice, and not to try and narrow down too quickly