Even if we cannot follow Heywood’s engagement with the fine details of political events in his work in these years in quite the way that we could through his earlier interludes, it is nonetheless possible, and important, to track his path against the wider picture of English Reformation politics, the advance of royal policy and the reactions it provoked, in order to see how the twists and turns of Fortune’s favour affected him, his family, and influential patrons such as Mary Tudor, and how and why Heywood was brought to his own crisis of conscience in the winter of 1543. This chapter examines Heywood’s fortunes in the years following More’s death against the curious contortions of Henry VIII’s religious policy, describing the evolution of Henry’s Erasmian ‘middle way’ in religion, and the tensions that it permitted and exacerbated, setting the scene for Heywood’s condemnation for treason for denying the Royal Supremacy in 1542.