This dissertation explores the South African War (1899-1902) and Canadian literary production. I examine newspapers, periodicals, and books published during and shortly after the War to argue that early articulations of Canadian identity, settler colonial discourses of whiteness and gender, and ideas about national literature were informed by Canada's participation in a conflict in a distant settler colony. In chapter one, I study how the Canadian Magazine produced a nationally-identifiable image of the volunteer soldier and the mounted policeman. This construction of the soldier occurred when the emergence of a "modern realism" in literature was debated. In this period often characterized by romantic nationalist discourse, I identify a contiguous materialization of a form of realism in the pages of the Canadian Magazine, as editors and writers portrayed the War. In chapter two, I turn to the understudied participation of forty Canadian school teachers in War internment camps and reveal how the women were constructed as models of Canadian femininity through national media coverage. I study E. Maud Graham's writing and recuperate uncollected letters by Florence Randal Livesay to argue that their narratives, rather than benevolent feminized observations, enacted a settler femininity that was not simply British, but British Canadian. In the final two chapters, I trace how the War occupies a complicated place in an ambivalent literary memory. I examine fiction by Gilbert Parker, Stephen Leacock, and Sara Jeannette Duncan. Parker's imperial romance centring Britain is a model that Leacock and Duncan resist; they use the romance as a foundational genre to represent Canadian experience in a triangulated relationship with South Africa and Britain. I trouble Leacock's representation of South Africa as a romantic space that exposes, by contradictorily silencing, criticism of war and settler violence. I reveal how Duncan depicts Canadian experience as resisting the lingering effects of martial imperialism in order to centre women in future imperial projects. I argue that the settler race-making enacted in the texts I examine depends on an emergent realism that, produced by the discursive and material transperipheral connections of the War period, registers the insufficiency of the romance and its binary structures.