 Augustine (354–430) is the central bridge between the ancient and medieval eras of philosophy. His mature thinking about the will was influenced by his early encounter with late classical Neoplatonist thought, which is then transformed by the theological views he embraces in his adult Christian conversion, famously recounted in his Confessions. In that work and in the earlier On the Free Choice of the Will, Augustine struggles to draw together into a coherent whole the doctrines that creaturely misuse of freedom, not God, is the source of evil in the world and that the human will has been corrupted through the ‘fall’ from grace of the earliest human beings, necessitating a salvation that is attained entirely through the actions of God, even as it requires, constitutively, an individual’s willed response of faith. The details of Augustine’s positive account remain a matter of controversy. He clearly affirms that the will is by its nature a self-determining power—no powers external to it determine its choice—and that this feature is the basis of its freedom. But he does not explicitly rule out the will’s being internally determined by psychological factors, as Chrysippus held, and Augustine had theological reasons that might favor (as well as others that would oppose) the thesis that all things are determined in some manner by God. Scholars divide on whether Augustine was a libertarian or instead a kind of compatibilist with respect to metaphysical freedom. (Macdonald 1999 and Stump 2006 argue the former, Baker 2003 and Couenhoven 2007 the latter.) It is clear, however, that Augustine thought that we are powerfully shaped by wrongly-ordered desires that can make it impossible for us to wholeheartedly will ends contrary to those desires, for a sustained period of time. This condition entails an absence of something more valuable, ‘true freedom’, in which our wills are aligned with the Good, a freedom that can be attained only by a transformative operation of divine grace. This latter, psychological conception of freedom of will clearly echoes Plato’s notion of the soul’s (possible) inner justice.