John Milton’s masque, with its chaste maiden trapped in Comus’s unchaste throne, offered a particular argument about the need to overcome both the unchaste tyranny of princes and, within the individual heart, the tyranny of pride. Milton’s vision of chastity saw spiritual combat enacted through the processes of textual production and a complex deployment of the classical humility topos that placed the submission of the self to authority within a framework of political opposition. This chapter offers a comparative reading of the performed and printed versions of A Maske Performed at Ludlow Castle because in each text Milton drew the line between chastity and tyranny very differently. The chapter’s analysis of Milton’s performed and printed masques demonstrates how intentioned was Milton’s translation of the performed genre into the written word. Strengthened by those anti-court and anti-Laudian arguments laid out in Chapter Three, Milton’s adaptation explicitly denied the chastity most associated with the court’s performed masques and reinscribed it in the language and printed discourses of political rebellion and theological introspection. In this sense, his masque constitutes a major intervention in the Caroline cult of chastity and needs to be considered as a significant marker of change in the turning of public opinion against the King.