How can we teach empathy to design students? How might we encourage them to consider people beyond their own perspectives? Can Product Design students be empowered to make a positive change in the life of another? Here we propose a way to start the conversation, using matchsticks. This project challenges universities to beyond the obvious ethical and social issues framed around sustainability and asks Undergraduate Design Students to engage with a demographic that is typically underrepresented both in society and in design intervention, Prison Offenders. In order to encourage a more empathic approach to Design, working in collaboration with a UK Prison, First Year Product Design Students at Nottingham Trent University were set a Design Project that challenged them to improve life within the confines of a prison cell. Over the course of 2 weeks, student groups were tasked with creating products that improved quality of life within a prison cell, utilising matchsticks, and construction techniques available to inmates. Guided by an expert Custodial Educator, students collaborated to generate visual, wordless guides that would enable any inmate to generate their products. Overall, the project was a success, with a number of innovative outcomes being produced, and empathetic skills being developed, however, there are areas for improvement which we discuss. The results were confirmed via an anonymous end-of-project questionnaire with students commenting that the experience was immersive and designing from the perspective of a Prison Offender being a truly unique opportunity.