Abstract The teacher–student interactions of 39 students exhibiting high externalizing behavior problems and 59 students exhibiting average behavioral adjustment from urban elementary schools were directly observed. Comparisons between these students within four different instructional contexts indicated that levels of student engagement were significantly related to both behavior and classroom context. Although teachers’ use of behavioral management strategies was minimal, it was significantly related to the type of instructional context in which it occurred. Findings are discussed in terms of how different instructional contexts place unique demands and offer distinct affordances for students with behavior problems. A more comprehensive understanding of the influence of these environmental contexts can allow teachers to scaffold task demands to bring them within the domains of the student's ability.