No ‘Pelagian’ sermons have been preserved. The anti-Pelagian sermons, especially those of Augustine of Hippo, raise two research questions: how to preach on grace or predestination in a mainly exhortative genre? Do the specific contexts of the sermons furnish different insights with regard to Augustine’s anti-Pelagian tenant? This chapter analyses the popular translation of Augustine’s doctrine of grace, the place of Scripture, the chronological continuity and developments of his thought, and his heresiological strategies in his anti-Pelagian sermons. It shows that the preaching’s content is broadly the same as in the treatises, but that different contexts entail unique frameworks and unique thematisation, because the sermons emphasise human freedom and ethical responsibility. They thus provide a new understanding of Augustine, more complex than the treatises. Finally, Pelagianism is rarely mentioned in the sermons after Augustine.