In his sermons, Augustine applies his more theoretical considerations of God’s impact on human willing to the concrete, day-to-day challenges of his flock. As he seeks to spur his congregation on in its mundane struggles of will, Augustine develops an account of God’s grace and our willing that is at once starkly realistic about human limitations and hopeful about what God can do in and for the faithful, even in this life. While Augustine frankly forecasts that ongoing wrongful desires, painful curative procedures, and inner turmoil will be the norm, he also emphasizes that love eases these burdens, enabling genuine progress and human contributions. The resulting vision carries, rather than dissipates, the energy generated by the biblical friction between such realistic and optimistic assessments of God’s mercy at work in human life. In this sense, Augustine’s preaching on God’s grace and our willing is charged, never neutral.