Owing to rapid urbanisation, cities are becoming a key locus for making sense of, and influencing, social and technological development. Urban sustainability is high on the research as well as on the development agenda. The complexity of modern cities often defies conventional governance mechanisms to promote sustainability, such as regulation, information and economic incentives. This has prompted a growing interest in innovative approaches based on collaborative learning in diverse groups of stakeholders in pursuit of sustainability. In this article, we wish to contribute to, and advance, the research and practice regarding urban sustainability by exploring the experiences of designing and facilitating a programme for multi-stakeholder collaboration, trust-building and concerted action in six cities in Europe, southern Africa and Southeast Asia. We apply an action research method called ‘learning history’ to understand the learning processes in the design and facilitation team and in two multistakeholder groups in Makana in South Africa and Malmö in Sweden. The findings illustrate how collaborative learning theory and systems thinking framed useful praxis for facilitating rich learning processes in these three teams. The article is presented in four sections: Section 1 provides the introduction and orientation; Section 2 provides a process description of the design of the SUS Programme; Section 3 provides learning histories; and Section 4 provides reflexive engagement on these.