Cicero’s dialogues exhibit a sceptical philosophy of education that uses problems in the epistemology of testimony to motivate inquiry from the reader. Sceptical Academics before Cicero devised a pedagogical method for their auditors that comprised of three practices: to argue against testimony as a source of knowledge, to conceal personal views by privileging the role of questioner in dialectical exchange, and to controvert established interpretations of philosophical predecessors whose texts might be used as authoritative testimony. Cicero textualizes these sceptical methods in interesting ways. The result is what I call “textual scepticism”, an authorial attitude that not only is sceptical of texts as sources of testimonial knowledge but also uses literary conventions to direct this scepticism recursively on the text in which it is expressed. After reconstructing the sceptical pedagogy of the Academy by looking for the presence of the three above mentioned practices in the evidence for Hellenistic Academics, I argue for its reception and textual transformation in Cicero’s De finibus, Tusculan Disputations, Brutus, and De oratore. Cicero’s textual scepticism relies on literary conventions of dedication and prefatory address. In the case of De finibus and Tusculan Disputations, Cicero uses these conventions to oppose an earlier work of Latin philosophy, Brutus’ De virtute. There is, then, an argument between authors supervening on the dialogues’ first-order disputes. In the case of Tusculan Disputations, Brutus, and De oratore, episodes of reading and interpretation—Cicero reading Plato in TD, Atticus interpreting Cicero in Brut., Crassus reading Plato and Cicero interpreting Crassus in De or.—create arguments over authors, in a way that leaves readers with questions and, with hope, a desire to look for the truth outside of a book.