High school students, particularly those with disabilities, often struggle with academic engagement in general education classes. One empirically supported method for improving academic engagement includes self-regulation interventions. However, individual effects of frequently used self-regulation strategies’ goal setting and self-monitoring remain unknown. To address this issue, we implemented a multiple-probe single-case design with embedded alternating treatments to evaluate the differential impact of behavioral goal reminders and self-monitoring. The sample included three high school students with emotional or behavioral disorders (EBD) in general education classes who also received special education services. Innovative approaches to intervention design included student-determined behavioral goals and self-monitoring procedures informed by triangulated behavioral assessment data. Although visual analysis indicated only moderate improvements in academic engagement, and no functional relations were determined for either the multiple-probe or alternating treatments designs, the intervention was rated with high social validity from teachers and students, and the study represents an exemplar of high-quality special education single-case research. Practical implications, limitations, and directions for future research are discussed.