Boethius’ Consolation of Philosophy promises an existential consolation that results from a philosophical insight. But what exactly does this consolation consist in and what is the insight that provides it? This chapter argues that Boethius’ philosophical consolation arises from an insight into the highest principle (principium) of practical knowledge: God conceived of as the highest good (summum bonum). For Boethius, the cognition of this principle also leads to an insight into a comprehensive cosmic order, ruled by God as the highest good, against the background of which even painful experiences, such as those of the first-person narrator of the Consolation, can be reassessed. Given that Boethius’ notion of consolation is embedded in the context of the Greco–Roman philosophical tradition, this chapter considers the metaphysical underpinnings of Boethius’ practical philosophy in light of his main philosophical predecessors: Plato, Aristotle, the Neoplatonists, and Augustine.