Arlisha Norwood examines a special category of women, those who temporarily or permanently could be classified as “single” in Virginia. This chapter argues that this population which includes unmarried, divorced, widowed, abandoned and separated women were the most economically vulnerable group during and after the war. Despite the unique obstacles they faced, single Black women asserted their needs, worked together to prevent destitution, and challenged the agendas of governmental agencies and private organizations whose well-meaning intentions often clashed with their own expectations. Their petitions for support and compensation altered the roles and responsibilities of federal and local agencies and made these women prominent characters in defining freedom, welfare, citizenship, and womanhood in the nineteenth and early twentieth centuries.