Promoting student self-determination is recognized as the best practice in secondary transition planning. Few self-determination interventions have utilized technology to provide individualized learning opportunities. The Goal Setting Challenge (GSC) App was developed to provide a technology-based instructional approach to support developing self-determination. The purpose of this single-case study was to evaluate the impact of the GSC App on self-determination knowledge outcomes for students with disabilities and explore the feasibility of students' use of the App in transition planning over an academic semester. Results were significantly impacted due to the COVID-19 pandemic; however, this created opportunities to explore feasibility during in-person instruction and the unprecedented shift to remote learning. Findings suggest mixed results related to outcomes for student use and feasibility but suggest the possibility of the App providing a student-friendly means for engaging in self-determination instruction during in-person and remote instruction. Limitations and implications for future research and practice are discussed.