Medieval literary narratives and historical records show that medieval women navigated various spiritual and material postmortem concerns in their families and communities. They arranged for prayers to speed their loved ones' souls through purgatory and made similar provisions for themselves, overseeing the administration of their loved ones' estates and coordinating the correct execution of their own property. This dissertation takes the unusual approach of considering women's differing approaches to these overlapping concerns. Chapter One argues that vision narratives in Bede's Historia Ecclesiastica encourage readers to understand their responsibilities to pray for souls in the afterlife as they do penance for their sins. It then turns to extant Anglo-Saxon wills to discuss how the responsibilities of noble and aristocratic women are represented. Chapter Two presents a new reading of the "Wife of Bath's Prologue" that emphasizes her unique approach to her fourth husband's death as she balances her postmortem responsibilities to him with her immediate remarriage. Alison compares the tomb she provides her fourth husband unfavorably with the one built by Alexander for his enemy Darius, but reveals that she acts with concern, while also tending to her own wishes.The third chapter examines a network of wills of women from aldermanic families in late thirteenth-century London, particularly focusing on Isabella Bukerel, one of the wealthiest women in London during this period. As they prepared for their deaths, thirteenth-century London women capably prioritized not only their own legal, material, and spiritual interests, but also those of their family members. Additionally, Bukerel's will and her sister's acknowledge an important relationship between Bukerel and her clerk. Chapter Four argues that in the Middle English romance Ywain and Gawain, a network of grieving women grapple with competing personal and public responsibilities after the death of an important male member of the community. Alundyne's responsibilities to her court must outweigh her desire to mourn her husband, while the daughter of a lord ignores her private and public responsibilities and disinherits her sister to keep the estate for herself. The conclusion closes the dissertation with a discussion of another fourteenth-century romance, The Awntyrs off Arthure, in which Guinevere must fulfill her own responsibilities to her dead mother after a visit. This narrative crystallizes the important private and civic responsibilities that women in this dissertation must meet and the resources they utilize to balance their concerns.