Cities are facing challenges from climate change. Impacts like flooding and extreme weather, and solutions like green infrastructure and carbon pricing, exploit weaknesses in human cognition and organizational design. Neither urbanites nor city governments are predisposed to prioritizing long-term resilience and sustainability over short-term development. A persistent challenge in sustainability science remains the co-developing of solutions that are desirable, politically viable, and truly sustainable in accounting for impacts across multiple interconnected systems. Recently, some in sustainability have shifted focus to transformative capacity building among key actors in cities as a means of fostering transformation in urban systems toward sustainability and resilience. Transformative capacity in individuals and organizations is conceptualized as constituent of competence, confidence, commitment and power. This paper describes two game-based approaches to building transformative capacity in city administrations and utilizes the concept of transformative capacity to unpack how universities and cities can collaborate and learn from one another and from other such partnerships. The two games, Future Shocks and City Resilience, and AudaCITY, are based on key competencies in sustainability education, the Sustainability Research and Problem-Solving framework, and Transition Management. They aim to develop the competence, confidence, and commitment of players, in particular city administrators, to develop, test and implement solutions for urban resilience and sustainability, while shifting power dynamics in favor of such efforts. The games were developed and tested in Tempe, Arizona with the City of Tempe. They served as the primary transformative capacity building exercise for senior leadership in the city administration in advance of the city’s first effort at developing a Climate Action Plan. The paper concludes with insights on the theoretical contribution of transformative capacity to reframing urban resilience as a challenge of human and organizational learning and methodological insights on the role of game-based approaches in enabling such learning.