Promoting self-determination is essential to effective transition services and supports. The Goal Setting Challenge App (GSC App) was developed to deliver self-determination instruction via technology, building on the evidence-based Self-Determined Learning Model of Instruction (SDLMI). This article presents data on goal attainment outcomes for students with disabilities who participated in a small, cluster-randomized controlled trial (C-RCT) of the GSC App during the 2020 to 2021 academic year and the ongoing COVID-19 pandemic. Findings suggest it is highly probable the GSC App enhances student transition goal attainment outcomes after one semester, with students three times more likely to attain their self-identified transition goals in the GSC App than in the business-as-usual condition. The impact of COVID-19 on implementation and sample loss is described, as are implications for research and practice.