The complexities of including students with autism in schools throughout Australia has resulted in the increased necessity for collaboration between stakeholders. For included students with autism, secondary school presents a variety of subjects, teachers and peers that have the potential to increase anxiety levels compared to their primary experience. Communication between important stakeholders is critical in alleviating issues for students with autism before they escalate. In this paper, researchers report and reflect on the implementation of a co-design process as a rigorous practice-based research methodology that provided an empathy focussed platform to explore possibilities in designing a prototype digital solution to support students with autism. The project was designed to identify communication issues associated with the secondary experience of students with autism and to create solutions via the development of a rapid prototype communication app. Findings from this project suggest that involving diverse stakeholders in co-designing and exploring possibilities in complex school environments had two benefits: stakeholders had the opportunity to see the challenge from other parties' perspectives, and the process promoted creativity and flexibility in generating people-based solutions.