Researchers have found that English teachers in the United States of America (USA) perceive providing writing instruction to students with emotional behavioral disorders (EBD) as a difficult task. This could be associated with the fact that students with EBD often work below skill level in the content area of writing compared to same age peers. Researchers continue to investigate interventions to increase academic outcomes for students with EBD. Utilizing a single case design, three middle school students with EBD were observed in a self-contained classroom to determine the effects of a traditional and technology based self-monitoring intervention focused on decreasing student off-task behaviors while increasing scores on writing assignments. The study took place in an urban school district within the Southeastern region of the USA. Results indicated that the first two intervention phases were equally as effective at reducing off-task behaviors. Additionally, the third intervention phase led to decreased off-task behaviors and increased writing scores for all students compared to the previous two phases. Social validity assessments indicated that the self-monitoring interventions were useful and relevant for teachers and students with EBD in the self-contained setting. Implications for teachers and educational researchers are discussed within this article.