Multitiered frameworks like Positive Behavior Interventions and Supports (PBIS) have been recommended for preventing and remediating behavior problems. In this study, technology-based self-monitoring was used as a Tier 2 intervention to improve the academic engagement and disruptive behavior of three middle school students who were identified as at risk for failure and needing immediate intervention. Results of the multiple baseline design across settings indicated the intervention was highly effective for one student and moderately effective for another. The third student required more intense support than offered in Tier 2. Issues of matching students to Tier 2 intervention based on multiple data sources, the alignment of technology-based self-monitoring with key features of Tier 2, limitations of the study, recommendations for future research, and implications for practice are discussed.