The Progressive Era was characterized by debates about the future of the United States and the role of individuals, households, and organizations in shaping that future. These debates included those about domestic work, sometimes specifically referred to as the “servant question” or the “servant problem.” This discourse considered not only paid household labor, but also the nature of race, gender, and American life after slavery. This article reviews the servant question in Washington, D.C., and reveals how commentators engaged with modernity and nostalgia to understand the contradiction between their sense of white and African American women’s failures and their belief that both groups of women belonged in white households. The servant question is key cultural context for a 1917 “favorite servant contest.” The second half of the article examines the clubwomen who organized the contest and the experiences of an elderly, formerly enslaved woman named Theresa Harper. The organizers responded to the D.C. servant question with an effort to carry racial hierarchies into the twentieth century, a vision of the future of household labor very different from that of Black domestic workers.