This chapter shows that the faculty of the will was presented as a ubiquitously dangerous facet of selfhood in Elizabethan and Jacobean plays, when used to gratify selfish or sinful desires. ‘Punishing the Transgressive Will’ explains how this convention helped define how the limitations of human ambition and the boundaries of moral transgression were depicted. I do so primarily through a comparative analysis of the notorious acts of wilfulness performed in Christopher Marlowe’s Tamburlaine the Great, Dr Faustus, and Elizabeth Cary’s The Tragedy of Mariam. Enticing as it was dangerous, the capacity for the will to incite violence or disorder was commonly shown to be the primary cause of its own ruin. This literary topos is, however, importantly refuted in Cary’s play through the character of Salome. Among all of the excessively wilful characters who feature in Renaissance drama, Salome proves to be an exceptional type of Neo-Senecan villain whose will functions without limit: her will is not self-defeating, nor is she punished for exercising it. I propose that Salome’s fate can help to redefine our understanding of transgressive acts in Renaissance tragedies.