The multi-tiered school-wide positive behavioral interventions and supports offers a comprehensive model for the prevention of behavioral and academic problems in schools. This study evaluated Check-in/Check-out (CICO), a Tier 2 intervention, with three elementary school students from a high-need population, whose problem behavior was hypothesized to be maintained by teacher attention. The study employed a concurrent multiple baseline design across participants, a single case experimental design to examine the effects of CICO on student academic engagement and problem behavior during instruction. Results indicated that implementation of CICO with fidelity by the CICO coordinator, classroom teachers, and parents lead to increased academic engagement and reduced problem behavior in all three students. Tau-U Effect sizes were medium to large for academic engagement and small to medium for problem behavior across students. Data on two students indicate that systematically fading the number of times teachers utilize the daily report card has the potential for promoting maintenance effects. For one student, fading of the coordinator was successful. Social validity assessment indicated high levels of satisfaction with the CICO intervention by the participating students, teachers, and one parent.