This dissertation focuses on the philosophy of Sextus Empiricus (c. late 2nd Century CE), a skeptic who provides the most complete account of Pyrrhonian skepticism that survives from antiquity. In particular, this dissertation examines Sextus' account of skeptical assent, the attitude that structures and informs the life of the skeptic. Accordingly, this dissertation has two aims: first, to elaborate and defend a novel method of interpreting Sextus' claims and concepts, one based on their significance in ordinary life and language; and, second, to apply this method to Sextus' claims about the nature of skeptical assent in order to generate a novel account thereof. In the first chapter, the most widely-held and influential interpretations of...