In the Trinitarian Convent of San Ildefonso, located in the barrio de las letras in Madrid, two nun authors—Sor Marcela de San Félix (1605-1688) and her successor Sor Francisca de Santa Teresa (1654-1709)—lived and wrote plays. The works these playwrights produced were spiritual colloquies meant to both entertain and educate their sisters. Despite the orthodox nature of these plays, the paradoxical convent space allowed for interesting and arguably unconventional uses of humor in what is usually considered a sacred space. The comic moments present in these texts usually stem from self-referentiality, such as bemoaning the strict nature of convent life or complaining about the lack of food Intramuros, or from social and gender norms, as when the World is represented as a lecherous but very rich old man attempting to woo the young and beautiful Soul. In both cases, the unique context of the cloister provides space for a particular brand of comedy that may not have been considered appropriate outside the convent walls. Only in this enclosed space could women such as Sor Marcela and Sor Francisca explore nuns’ lived experiences in such a jocular way while still underscoring their religious message of salvation.