Founded in 1875, the Girls’ Friendly Society (GFS) began as an organization to assist girls travelling to cities in Britain for the purposes of work. However, by the turn of the century, it increasingly focused its efforts on imperial matters and in particular on facilitating the emigration of working-class girls to the colonies. Yet emigration and the task of empire building proved more difficult than the organizers had envisioned. Using GFS reports, newsletters, correspondences, and memoirs, this chapter traces the challenges faced by the GFS, focusing in particular on its operations in South Africa. Through its emigration programs, the GFS sought to fashion imperial-minded girls who would in turn reinforce social and racial hierarchies within South Africa, but their efforts met with resistance from British girls, who opposed conditions in the colonies, and from African girls, who protested against their exclusion from the organization. Moreover, debates between branches in Britain and South Africa exposed fundamental misunderstandings about the complexities of colonial life. These contestations highlight the contradictions of the GFS’s professed commitment to “the care of the girlhood of the empire” and call into question the solidity and meaning of class, racial, and gender hierarchies that underpinned British society in South Africa and the wider empire.