Research indicates that early school success influences eventual life chances and that attentiveness in the classroom contributes to early school success. Using ethnographic fieldnotes, interviews, short surveys, and video footage collected over three school years, I investigate how teachers and young students experience "attentiveness" during their day-to-day interactions at school. Specifically, I reveal some of the social foundations and consequences of attentiveness in the first grade classrooms of "at-risk" students. In the first substantive chapter, I focus on teachers, describing how they take great efforts to manage attentive behaviors, yet are also the inadvertent sources of distractions. Additionally, by typologizing the kinds of inattention teachers deem acceptable, I unpack how judgments, circumstances, and student identities influence their enforcement of attentive behaviors. I also illuminate how teachers harness the idea of "attention" for classroom discipline and social control. The second substantive chapter highlights how students dynamically shape attentiveness in their classrooms. By self-regulating and collaborating with peers, first graders effectively direct focus onto their teacher's intended target. However, children also participate in auto-involvements and mutual engagements, often cultivating attention away from the task at hand. Moreover, young students actively perform attentiveness and as a result, skillfully remain undetected by the disciplining radar. In the third substantive chapter, I use my longitudinal data to examine how certain first graders become the "most inattentive" students in their classrooms. Teachers and peers identify various attentional difficulties—sometimes academic, but always social—of specific children and collectively inform their school identities. These outlier students—the "Easily Distracted," the "Needs to be Tested," "Divas and Drama Queens," and the "Bad"—serve as cautionary tales; their examples (re)establish normative behavior in the broader classroom culture. In sum, by providing a contextual understanding, this dissertation reveals that student attentiveness is in some ways a product of the collectively constructed social relations of a local culture, like the classroom.