The chapter traces statements on Cicero’s philosophical position from his earliest treatise (on rhetorical theory) to the philosophical works of the 40s bce, while attending to the literary form of Cicero’s oeuvre. It argues that Cicero’s stance is stable over time, that it exhibits a number of features that would warrant calling it mitigated skepticism, but that, given the way different Academic positions are conceptualized in Cicero’s texts, notably the Academica, his position is formally one of radical skepticism. The chapter tries to identify features of the evidence from Cicero which are distinctive compared to other texts (e.g. by Sextus Empiricus and Numenius), notably an unusual wealth of comments on the practice of Academic skepticism (i.e. on what being an Academic skeptic was like, at least on Cicero’s construal and to what extent it was compatible with being a fully functioning Roman of a certain social class and with a particular occupation).