Augustine played a crucial role in the history of philosophical skepticism. The paper emphasizes the three main reasons that place Augustine at a strategic point in relation to skepticism. Firstly, he is the author of Against the Academics, a philosophical dialogue where he discusses the arguments of the New Academy in order to go beyond skepticism. But, secondly, his conception of belief in the Christian faith can be interpreted as a response to the skeptical contention that one should live without belief. Finally, through his reflections on the problem of skepticism, Augustine conceived of a new form of it: skepticism as a thought experiment of the inner self, which exhibits a metaphysical and epistemological strength that from Descartes onward has remained vibrant.