Prior’s puzzle is standardly taken to be the puzzle of why, given the assumption that that-clauses denote propositions, substitution of “the proposition that P” for “that P” within the complements of many propositional attitude verbs is invalid. I show that Prior’s puzzle is much more general than is ordinarily supposed. There are two variants on the substitutional form of the puzzle—a quantificational variant and a pronominal variant—and all three forms of the puzzle arise in a wide range of grammatical positions, rather than merely in the complements of propositional attitude verbs. The generalized puzzle shows that a range of proposed solutions to the original puzzle fail, or are radically incomplete, and also reveals the connections between Prior’s puzzle and debates over the nature of semantic types and higher-order quantification. I go on to develop a novel, higher-order solution to the generalized form of the puzzle, and I argue that this higher-approach is superior to its first-order alternatives.