The turn from the nineteenth to the twentieth century marked a time of intensified data collection in the United States focused especially on childhood. This article explores how two children’s narratives, Francis La Flesche’s The Middle Five (1900) and Francis Rolt-Wheeler’s The Boy with the U.S. Census (1911), reflect and respond to this conjunction of boyhood, settler colonialism, and official surveillance. Read together, these texts provide a window into the ways that data collection mediated between the everyday lives of children and the bureaucratic machinations of US colonial governance, marking those data as a site at which governance could be asserted or contested. The colonizing discourse with which these texts engage treats numeracy (rather than the more common literacy) as the threshold for citizenship and reduces Indigenous people, in particular, to the passive objects of measurement and administration. More surprisingly, though, these books also display the role that children’s literature played in placing children themselves in a relationship with numerical data collection, either as enthusiastic and active participants or wary counteragents. While Rolt-Wheeler portrays bureaucracy as an imperialist adventure in which white boys should joyfully partake, La Flesche offers a portrayal of the harm that this incessantly quantitative thinking did to Native children, but he also adds a nuanced critique of the epistemologies underlying such thinking.