In his letter Against Monastic Life (1514-1517), Andrea Alciato, an Italian jurist and writer famous for his Emblemata, urges his friend Bernardus Mattius to reconsider his choice of monastic life. Alciato makes his argument by criticizing religious superstition, the Church’s hierarchy, and monastic practices, particularly the Franciscans’ hypocrisy, wealth, and divisiveness. Instead, he defends a stoic, civic humanism. Due to the troubled history of this unique manuscript and the inadequacies of the two subsequent editions, Alciato’s discourse has been obscured for centuries. This edition and translation seeks to make clear the biographical importance of the text for one of the major figures of the European Renaissance.