Situating the endeavors of Asa Shinn Mercer and Domingo Faustino Sarmiento within the broader settler colonial histories of the US and Argentina, this study provides two cases in which men representing prominent settler groups in the Americas attempted to regulate via internal educational colonialism populations they considered divergent from the nations' ideals. Both projects recruited women to serve as civilizing agents who would help align disparate groups with the desired standards of citizenship. The female participants, however, did not blindly conform to their leaders' expectations of behavior, instead asserting their own will at key points during the projects' execution. Examining the groups' dynamics in tandem provides new examples of the gendered processes at play within the settler colonialist structures of two nineteenth-century American countries.