This intervention study explored the effectiveness of a Tier 2 intervention, Check Ins and Logging Moods (CALM) (e.g., Check-in/Check-out with integrated components of Cognitive Behavioral Therapy and daily self-monitoring) on 7th grade students at risk for internalizing behavior problems. The study was conducted in two different school sites, CA and MA and used a combination of Multiple Baseline and simple AB single-case design with multiple outcome measures. The CALM intervention consisted of 6 lessons taught once a week for 6 weeks by the interventionist who held weekly meetings to review students’ self-reported mood, engagement and use of coping skills-- holding a space for students to reflect upon their week. Data collectors also conducted 20-minute observations to monitor the frequency of students internalizing behaviors. Visual analysis of direct observations, student self-reported mood, engagement and coping skill use data along with single-case effect size calculations indicated that there was a functional relation between the CALM intervention and an increase in students self-reported engagement at the school site in CA. However, many challenges occurred conducting school-based research. Findings from the current study provide evidence that through frequent check-ins and teaching coping skills, middle school students who are at-risk for internalizing behavior problems can increase perceived engagement in school and self-awareness.