This chapter focuses on the Medicean context of the publication of the 1568 Primo libro a4, dedicated to Isabella de’ Medici. After hypothesizing about the Romano–Florentine networks that brought Casulana into contact with Isabella, it shows that Casulana’s book sits within a broader tradition of Medicean philogyny. The woodcut printed on the frontispiece of the Lamento di Olimpia, published by Stefano Rossetti in 1567 with a dedication to Isabella, contains a Sibylline philogynist message that provides a direct precedent for the much more explicitly pro-women statements that Casulana would make a few months later. The chapter analyzes how Casulana’s dedication draws on philogynist arguments that had been circulating in Italy for several decades, and how she set herself up as a living example of female excellence. Casulana’s dedication also had a more utilitarian purpose, that of gaining the support of the Medici in the lawsuit she was about to file against her husband for squandering their household’s money.