This study addressed questions about the relations among teacher instructional interactions, classroom environmental contexts, and students' subsequent self-regulated learning behaviors in upper elementary school. One hundred and six 4th- and 5th-grade students from five classrooms in two schools in two communities (one urban and one rural) in the southern United States participated in the study. Each student was observed in ongoing classroom learning activities during teacher-directed and student-centered academic tasks throughout the school year. A structured observational protocol was used to record information about instruction and feedback provided to students by teachers, classroom and environmental contextual features, as well as students' self-regulated learning behaviors. Findings revealed that teachers' instructional information and feedback content both directly and indirectly predicted students' self-regulation behaviors in the classroom. However, features of the classroom environment and structure influenced how the students made use of the available information and mediated the effects of classroom social interaction.