Homework enables students to practice what they learn from classroom instruction. However, students' off-task behavior may negatively impact their engagement and performance during homework activities. Self-monitoring is an evidence-based intervention associated with improved engagement and decreased off-task behavior. Compared to traditional self-monitoring using paper and pencil, technology-based self-monitoring (TBSM) has several advantages in supporting students. This study aimed to investigate the effects of a TBSM intervention package on students' off-task behavior and homework completion during homework routines at home. In addition, this study explored whether parents and students (a) were able to implement TBSM with fidelity at home and (b) perceived TBSM intervention package as feasible and socially valid in their home setting. The intervention consisted of a TBSM mobile application named I-Connect, explicit online training, a self-monitoring accuracy monitoring system, and parents' on-going support. I employed a single-subject multiple baseline design across three participating families. The results demonstrated a functional relation between the TBSM intervention package and desired behavior change. The intervention's effect on homework completion was not compelling. The results indicated that parents and students could employ the intervention package with fidelity, and they found it socially acceptable. I conclude with a discussion of study limitations and implications for future research. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]