In Categories 12 (14b11–22), Aristotle famously claims that [1] true sentences and reality stand in a mutually implicative relationship, and that [2] reality causes the truth of sentences but not vice versa. In this paper, I first argue that Boethius’ reading of the above passage led medieval logicians to assess [1] and [2] within the framework of a theory of consequence. Then, I consider two important questions raised by Boethius and later logicians in relation to [1] and [2], and, namely, whether the implication described in [1] really satisfies the requirement for consequence, and whether the truthmaking relation posited in [2] can be boiled down to the relation of consequence. Boethius himself, I argue, answered affirmatively to both questions and thus (much like some contemporary truthmaker theorists) committed himself to an account of truthmaking as entailment. I then consider criticisms to Boethius’ account found in the writings of William of Champeaux, two anonymous authors connected to the school of Jocelyn of Soissons, Peter Abelard, and the author of the Ars Meliduna. Here, I argue that the emergence of a concern for relevance drives the need for abandoning Boethius’ account as well as his conception of truthmaking as entailment.