To address instructional challenges and poor academic outcomes of youth in juvenile correctional facilities (JCFs), we must understand how and why some teachers are effective and why students are responsive to instruction in these settings. We observed and coded teacher--student instructional interactions from 733 fifteen-minute classroom reading sessions for seven teachers and 40 students in a secure U.S. JCF school. We then applied a series of time-window sequential analytic procedures to assess connections between instructional approaches and teacher behaviors, and contingent student engagement and response behaviors. We also compared contingent probabilities for students with disabilities and students without disabilities. Across all students, our observations were characterized by larger proportions of passive student engagement. We also found a relatively low use of teacher praise. When teachers provided either directives or opportunities to respond, conditional probabilities for appropriate student responses were higher across students, particularly when directives were provided to students with disabilities. We discuss additional results and implications for research and practice.