Shakespeare’s plays exhibit a sustained interest in rhetoric and in epistemology. Critics have been attracted to Othello in their attempts to understand Shakespeare’s view both of the nature of rhetoric and of the ability of human agents to penetrate beneath false appearances so as to acquire authentic knowledge. This article proposes that our understanding of Shakespeare’s view of rhetoric and of epistemology can be deepened by reading Othello with Cymbeline . While Shakespeare shows the real power of sophistry and concealment in the character of Iago, whose façade is impenetrable and whose words are persuasive, Imogen’s ability to discern the evil intentions of the honey-tongued Iachimo and to forestall tragedy with her own ethical, skilled speech enlarges our understanding of Shakespeare’s conception of rhetoric and epistemology and challenges interpretations in which it is proposed that he has a cynical view of rhetoric and a skeptical epistemology.