This chapter compares the epistemological assumptions of late-antique Prolegomena to Philosophy with those of the Didaskaliai of Dorotheus of Gaza, a sixth-century ascetic teacher. It focuses on the epistemic role of godlikeness, the claim that the goal of philosophy, understood in terms of either Neoplatonism or the monastic life, is to become like God. In both Neoplatonism and in Dorotheus’ teaching, the concept of godlikeness orders knowledge and promotes ways of knowing developed in order to bridge the gap between the politico-ethical and the spiritual, the practical and the theoretical. Comparing Dorotheus’ teachings with the Introductions to Philosophy identifies substantial shared epistemic assumptions. A key difference between the schemes is generated by the epistemic role of humility in Dorotheus’ account.