Chapter 1 takes Gertrude Stein’s visit to the recently incorporated “Indian Territory” of Oklahoma as an opportunity to reread her geographical histories of the United States from a point in Native space. It contrasts Stein’s love for state lines with the writings of Yankton Dakota writer Zitkála-Šá. Her autobiographical essays of the early twentieth century contain shadow maps of Očhéthi Šakówin, or The Great Sioux Nation. They complicate Stein’s excitement over how the airplane makes patchwork earth look like an official US map. By reading contrapuntally between Stein and Zitkála-Šá, this chapter considers autobiography as a contested genre of cartographic literature. In response to technics of automated transport, the form was retooled by Stein and Zitkála-Šá in ways that make the overlap of US geography and Native space visible as a differential space.