Women’s work both within their own households and within the community at large has been the focus of a significant amount of historical research during the last century.1 Just how women worked outside the home and what the conditions of their labor were over the century has been the subject of ongoing debate. Most of these studies, particularly Marjorie McIntosh’s 2005 groundbreaking work, have mined poll tax records, equity petitions, and other court documents to form a kaleidoscope of impressions regarding late medieval and early modern working women. This chapter takes a new approach by shifting the focus of the research to women’s wills, using them as reference points and exploring the material available in them to isolate and analyze both the work that women did and how they contextualized it in their last testaments. These testaments reveal not only the occupations of the will-makers themselves but often describe the occupations of other women known to them. This probate-based approach listens to the voice of the will-maker unfiltered by the male-dominated processes that compiled and registered tax and court records.