Check-In/Check-Out (CICO) is an effective and widely used Tier 2 behavior program in elementary and middle schools. This article describes a pilot study focused on examining the impact and usability of an adapted CICO program in a high school. We used a single-case multiple baseline design across five 9th grade students to evaluate the effects of the program on student academic engagement and disruption/non-compliance. In addition, we administered social validity questionnaires to school personnel and students to assess the usability of the program. Findings were mixed in terms of impact on student behaviors. Both school personnel and students found the program useable. Based on these findings, we discuss limitations and offer recommendations for how high school personnel could use CICO to support students at-risk of school failure.