Many African American males experience disproportionate exclusionary discipline actions, disproportionate special education referrals and restrictive placements, poor academic achievement, and poor post-school outcomes, a phenomenon often referred to as the school-to-prison pipeline. Reformists suggest that multi-tiered systems of support (MTSS) such as School-wide Positive Behavior Interventions and Supports (SWPBIS) have the potential to mitigate disproportionality and minimize the effects of the school-to-prison pipeline (e.g., Advancement Project et al., 2011; Florida's Positive Behavior Support Project & University of South Florida, 2011). Check-In Check-Out (CICO), a frequently used Tier II intervention within the tiered framework of SWPBIS, has been shown to reduce problem behaviors and increase academic engagement of targeted students. Although effective with some students, CICO has not provided enough support for approximately 22-33% of students receiving the intervention (Hawken, Bundock, Kladis, O'Keeffe, & Barrett, 2014; Swoszowski, McDaniel, Jolivette, & Melius, 2013b). Tier III interventions are often implemented with Tier II nonresponders. One intervention meeting the characteristics of a Tier III MTSS intervention and demonstrating positive effects on the behaviors of at-risk students, to include African American males, is function-based self-management (Lo & Cartledge, 2006; Stahr, Crushing, Lane, & Fox 2006). This study evaluated the effects of a MTSS using CICO as a tier II intervention and function-based self-management delivered via an electronic device as a Tier III intervention on the disruptive behaviors and academic engagement of three African American male students. A single-case, multiple baseline across participants design (Cooper, Heron, & Heward, 2007) was conducted to evaluate the effects of CICO on the participants' disruptive behaviors and academic engagement. Additionally, a reversal design (Kazdin, 1982) was used to evaluate the additive effects of function-based self-management with one of the participants. Results indicate a reduction in disruptive behaviors to the level similar to that of comparison peers for the three participants and decreased variability in disruptive behaviors for two of three participants upon introduction of CICO. In addition, two of the three participants increased academic engagement to the level similar to that of comparison peers and experienced decreased variability of academic engagement upon the introduction of CICO. Evaluations of electronic function-based self-management reveal a decrease in disruptive behaviors and inconclusive findings on academic engagement. Implications for practice and suggestions for future research are discussed.