Teaching Shakespeare and Moral Agency begins with respect for the unschooled insights students express and supports their emotional engagement with the plays. Students were asked to set aside historical context and to engage directly with the resistant structure of the text. Building from their own background knowledge and the spontaneity of their response, it is then possible to develop their preliminary insights into a more rigorous understanding of the moral seriousness of Shakespeare’s dramatic art. Contrasting styles of moral inquiry can then be used to put questions of this kind into a philosophical context. Required philosophical reading included Aristotle, Nichomachean Ethics; Erasmus, Enchiridion; Immanuel Kant, Prolegomena to the Metaphysics of Morals; Friedrich Nietzsche, Genealogy of Morals. These ethical encounters between contemporary readers and Shakespeare’s fictional universe often turn out to be profoundly disturbing. To illustrate the ethical distress provoked in these encounters the chapter builds on student responses to Isabella’s moment of decision in Measure for Measure: “More than our brother is our chastity.” What students discover from this program is a distinctively Shakespearean account of virtue ethics - conflicted, panoramic in scope and grounded in the concrete immediacy of experience.