Urban green infrastructure is not acknowledged in the Global South for the critical social and ecological functions it can provide. Contextual design solutions and innovative approaches are urgently needed to transform the status quo. University-local government collaboration could be a way to encourage new thinking, new roles and design skills to develop solutions to these complex problems. This paper presents a case study analysis of such a collaboration. Qualitative research was conducted to establish the degree to which the exposure to real-life projects stimulates postgraduate design students’ transformative learning. The researchers also inquired into the benefits of the collaboration for the municipality. The participants’ reflections were recorded by means of anonymous questionnaires. The findings show that the live project created a municipal setting for seeking alternative solutions in design processes and outcomes. For the students, the project created rich social dynamics and an interplay of familiarity and uncertainty, which aided transformative learning. The students’ deeper learning indicates greater social empathy, reconsidering the role of the profession, greater design process flexibility, and learning and valuing skills across disciplines. The findings hold promise for a more just and sustainable future built environment through collaborations that transform the design professionals involved, the outcomes they pursue, and the processes they follow.