Donne took holy orders and was appointed royal chaplain to James in 1615, and became Dean of St Paul’s Cathedral in 1621. This chapter explores his engagement, across a range of his sermons and other works, with both the immediate challenges posed by preaching for the King, and the underlying question of the relationship between earthly and heavenly authority. Donne was, the chapter argues, especially concerned to resist James’s exploitation of scripture for political purposes and to maintain autonomy as a preacher. The discussion culminates in a detailed examination of Donne’s Paul’s Cross sermons of September and November 1622. Engaging closely with royal words, these two key sermons extend the model of subjecthood Donne had developed. The chapter thus highlights that James’s books and interventions into the work of his clergy helped to shape Donne’s conception of preaching and practice as a preacher. It suggests that James, who approved of one of these two sermons and not the other, was willing to engage in the kind of ‘conversation’ Donne sought but only up to a point. These interactions illuminate some of the ways in which the intersections of religious and political authority were contested in Jacobean England.