Mates’s Puzzle has flown below many philosophers’ radar, despite its relations to both Frege’s Puzzle and the Paradox of Analysis. We explain the relations amongst these puzzles on the way to arguing that Mates’s Puzzle suggests a generalization of Frege’s Puzzle, and of the sense-reference distinction itself, in the form of hierarchy of senses. We explain how Mates’s Puzzle and the hierarchy, to different degrees, illuminate each other, and how their connection is missed in the literature. However, we argue that the potential of Mates’s Puzzle to illuminate the hierarchy is yet to be fully actualised. We suggest that in order to do better, we need to formulate Mates’s Puzzle as a puzzle in the philosophy of thought and not as puzzle in the philosophy of language. What is needed, to which the present paper is a precursor, is an account of the cognitive significance of higher-order senses.