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More than 20,000 primary- and secondary-level schools, which represent 20% of all schools in the United States, are implementing school-wide positive behavior supports (SWPBS) to enhance socially desirable behavior and promote a decline of problematic behavior among students. The overall efficacy of the 3-tier SWPBS framework is well documented. However, a paucity of empirical research addresses the use of check in/check out (CICO), a Tier 2 intervention, for youth who present as quiet and withdrawn, and who are at risk of academic and social disengagement. Accordingly, this quasi-experimental, nonequivalent groups study assessed the overall effectiveness of CICO and considered the differential effects of conducting a functional behavior assessment (FBA) at the secondary level of SWPBS. Twelve students from 1 middle school formed the convenience sample. Analysis of covariance repeated across time, with the preintervention scores being the covariate, was used to assess between group differences in the students' internalizing behaviors on the Behavior Assessment System for Children-Second Edition (BASC-2) Self-Report, teachers' BASC-2 ratings of adaptive skills, and office discipline referrals. Paired sample t tests were conducted to assess within-group effects. Findings indicate that CICO was an effective intervention for students presenting with a pattern of internalizing behaviors. For participants in the experimental group, a significant effect was found on the functional communication scale. Social change implications include educators having a better understanding of how Tier 2 interventions can be enhanced to meet diverse needs and that inclusion of youth's self-reports is needed when determining effects of supports.