Kate Chilton’s chapter explores the unique experience of women in the District of Columbia and argues that Black women drew on women’s strong position in the urban economy to choose work that allowed them to help support their families and demand respect and reciprocal obligations from their husbands. The strategies practiced by African American women during and after emancipation reveal the continuities between the prewar and post–Civil War periods that made urban freedom in the District of Columbia different and distinct. Despite the dislocations of the Civil War and the Reconstruction and the attempts of agents of the Union Army and the Freedmen’s Bureau to impose Republican ideals on Black women, emancipation ultimately served to reinforce prewar patterns of gendered behavior in former slave households. While Black men experienced great demand for their labor during the war, the resumption of a peacetime employment market meant that the majority of Black women would have to work in freedom.