Background: There have been several studies that involved technology-based self-monitoring procedures to increase on-task behavior. Although there are continued advancements in technology application such as functions that are embedded in the application (e.g., reinforcement, feedback), the appropriate use of technology is required to be accompanied by evidence-based guidance. Objectives: The purpose of this meta-analytic approach was to (a) examine the effectiveness of a technology-based self-monitoring system on the on-task behavior of students with disabilities and (b) provide information that can support the use of a technology-based approach as an effective method for the teaching of relevant behavioral skills. Methods: All reviewed 16 studies employed a single-case research design, targeting technology-based self-monitoring interventions for students with disabilities. Studies were descriptively analyzed and evaluated for methodological quality using the What Works Clearinghouse (WWC) standards and criteria. Additionally, to examine the level and trend of reading fluency outcomes, Tau-U was calculated across the studies by measuring the impact of various moderator variables on the intervention effects. Results and Conclusions: Overall, studies showed a strong effect of using the technology-based self-monitoring on on-task behaviors. The impacts of six possible moderator variables (i.e., school level, types of technology, student training, teacher feedback and teacher reinforcement) were analyzed and there was no significant difference in the six variables with regards to the effects of the technology-based self-monitoring on the improvement of on-task behaviors. Implications: Based on the findings that support the positive impact of using mobile technology for increasing on-task behaviors of students with disabilities, directions for future research and practical applications were discussed.