The purpose of this study was to examine the effects of a technology-based self-monitoring application, I-Connect, to enhance the on-task behavior of five secondary students (ages 15-16) with autism spectrum disorder, intellectual disability, and specific learning disability during Biology instruction in a rural special education classroom. We used an A-B-A-B withdrawal design with a generalization condition. The primary dependent variable was percent of intervals with on-task behavior as measured by momentary time sampling procedures. Results indicated overall higher levels of on-task behavior for all students when using I-Connect to monitor their behavior. However, there were also high percentages of overlapping data, and student satisfaction with the application was relatively low. Students used I-Connect in an employability seminar offered at their school as a means to generalize to a different setting. We provide implications for practice in rural settings and suggestions for future research related to I-Connect. We also provide recommendations for enhancing the social validity of technology-based self-monitoring for secondary students with disabilities.