[albertni]

It said in the article that the machine analyzes the category. My speculation is that if it correctly deduces that the category is one of those "answer-hybrid" ones, then it can try to break down the question into two parts, answer each, and cross-reference to find an overlap. In this case it seems pretty reasonable that such a sophisticated machine could break the problem down to "classic candy bar" and "female Supreme Court justice", combined with the knowledge that they share a word this would actually become "straightforward".