The information-transference account of teaching takes it to be a process in which information is transferred from one person's mind to another's. Augustine argues that this is impossible, since in order to understand something the person who understands must come to see why it is so, and that is an internal episode of awareness that isn't caused by an outside source. Augustine's insight here is contrasted with the contemporary view, following Wittgenstein, that learning is a matter of conformity to rules (public norms). The case is made that teaching and learning pose philosophical problems that contemporary theories don't address, and a brief examination of Searle's Chinese Room example suggests that its plausibility derives from Augustine's insight that mere rule-following behavior isn't enough to explain the phenomenon of understanding at the heart of knowledge. A reconstruction of Augustine's epistemological claims, divorced from his discredited views in the philosophy of language, is also provided.