In the decades following their convent’s foundation, Diana d’Andalò (d. 1236) and the sisters of Sant’Agnese maintained a literary correspondence with a number of leading Dominican friars—Master Jordan of Saxony (d. 1237) foremost among them. And while the sisters’ letters have not survived, 58 of those they received, and subsequently copied, reveal much about the nature of their religious life. Shorter and more occasional than what is typically found in twelfth-century religious correspondence, the letters shed light upon the sisters’ particular circumstances, pastoral needs, and spiritual aspirations. Moreover, even as they disclose the development of Diana and Jordan’s spiritual friendship—for which the letters are best known—they also record a variety of relationships between the sisters and other friars besides Jordan, even as Sant’Agnese struggled to maintain its status as a house of the Order of Preachers.