The current trend of higher education for sustainable urban development links with parallel developments in urban governance and environmental pedagogy. Many programs and policies identify cities and citizens as key drivers of change for sustainable futures, however scholarly work on the related pedagogies is lacking. These endeavors are clearly present in the Tampere city-region, Finland. Supported by national educational and city-regional strategies, the city is promoting sustainable lifestyles and infrastructures by means of multistakeholder governance including citizen participation and sustainability education. This paper analyzes, as a case study of transdisciplinary sustainability education, a collaboration between Tampere University, a skateboarding high school, and the Hiedanranta urban district developed as a real-life laboratory of sustainable urban development. We explore the pedagogical dimensions of the collaboration by drawing from the theoretical perspective of ‘positive recognition’ and conceiving the Hiedanranta skatescape—a socio-physical entity formed around skateboarding—as a ‘boundary object’. The paper suggests urban environments act as boundary objects that enable productive collaboration between various actors when informed by pedagogies of positive recognition. In conclusion, we propose that the value of this approach, binding together multistakeholder governance and transdisciplinary learning, lies in its capacity to encourage novel forms of sustainable agency.