To promote and enhance self-determination, the Self-Determined Learning Model of Instruction (SDLMI) was developed for teachers to teach students the skills needed to engage in goal-directed actions. The SDLMI was originally designed to be delivered by teachers, but technologies are emerging that can provide an alternative medium to delivering instructional content and promoting individualised learning experiences. This study: (a) describes the iterative development of the Goal-Setting Challenge (GSC) App, which 'translates' the SDLMI into a web-based platform; and (b) shares findings from focus groups with students and teachers to support student engagement with the App with a focus on usability and feasibility. The first phase of an iterative multi-year project to develop the GSC App for students with disabilities is described. Two themes (motivation and engagement, modifications and accessibility) emerged from participant focus groups and informed iterative development. Limitations and implications for future research and practice are discussed.