This article compares the work of two late medieval bishops and the guidelines each produced for convents. In the late fifteenth century, Talavera (1430–1507), bishop of Avila in Spain, wrote a treatise addressed to the Cistercian nuns of the city that touched on the core elements of female cloistered life. In 1517, Fox (1448–1528), then bishop of Winchester in England, chose to rewrite the Benedictine Rule in a format specifically addressed to women, adapting its principles more directly to the needs of female religious. A comparison of these two texts, their authors, and the environments in which each wrote facilitates a deeper understanding of the campaigns to manage and reform female monasticism in Spain and England. But it also invites a consideration of what a transnational examination of these questions might add to our understanding of female monasticism that has, until recently, been bound by strict geographies.