This chapter explores homiletical possibilities afforded by the book of Jeremiah to the Christian preacher. The earliest layers of contextualization are examined through consideration of preaching on Jeremiah in the early Church, focusing on sermons of Origen. In discussing the early modern period, the chapter attends to the preaching of Reformers Martin Luther and John Calvin. Finally, the chapter reflects on homiletical moves made by contemporary preachers in a variety of ecclesial contexts from the nineteenth century to the present, including Charles Spurgeon and Walter Brueggemann. Noteworthy in the homiletical reception of Jeremiah are four passages: first, the commissioning of Jeremiah (1:4–10), which foregrounds agonistic dimensions of prophetic witness and has served as a focus in liturgies of ordination; second, the lament, “Is there no balm in Gilead?” (8:22), transformed in a renowned African American spiritual into the asseveration that “there is a balm in Gilead,” namely, Jesus; third, Jeremiah’s depiction of the divine word as irresistible, “like a burning fire shut up in my bones” (20:9); and fourth, the promise of the new covenant that God will inscribe on the heart (31:31–34).