This paper examines an emerging shift in Augustine’s preaching of the work of charity, as it relates to poverty and almsgiving, in his commentary on The Lord’s Sermon on the Mount in 394 and a group of sermones ad populum from around 410-416. It compares his commentary on the Beatitudes in Book 1, which he characterizes as being about mercy, with sermons from the 410s, particularly sermons 53 and 53/A, explicitly on the Beatitudes, and related sermons, including four on the Lord’s prayer (56-59) and several others on isolated verses. In analyzing in these works, I give primary attention to the examples and motivations Augustine appeals to in explicating Mt 5:7 (the merciful), 5:1 (the poor in spirit), and 5:8 (those who hunger and thirst for justice/righteousness). When Augustine steps aside from his critique of the Donatists’ false charity and good works, on the one hand, and the formality of his structural analysis of the beatitudes and the seven gifts of the Holy Spirit, on the other, he opens a space for considering more material works of mercy in loving one’s neighbor. I argue that, in conjunction with his use of related Matthaean texts, we can see in these sermons from around 410 to 416 the beginnings of a larger shift in Augustine’s preaching of mercy that will become prominent in the last decade of his life.