In the fifth century, the critiques leveled by Pelagius and his supporters troubled Augustine so much that he spent much of his last years refuting the Pelagians and distinguishing his thoughts on sin, sinlessness, and baptism from theirs. Melania the Younger and her husband were caught in the middle of these theological debates, due to their friendly relations with both Pelagius and his supporters and Augustine and his. The Life of Melania the Younger preserves unresolved Pelagian tensions by celebrating Melania’s asceticism and insisting on her humility and sinful nature. In the Latin Vita, in a speech following a miraculous delivery of a stillborn child, Melania defends the purity of babies and bodies, all while reminding her audience of the filthiness of human sin. This chapter examines how the Life negotiates conflicts over theodicy, grace, sin, and the human potential for overcoming sin set in motion by the Pelagian controversy.