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Southern African cities face several challenges including management of rapid urbanization, rising populations, expanding informal settlements; adequate water and other service provision, and a host of governance challenges. Climate change and variability add a compounding effect to this complex, multi stressor context. Addressing the complexity requires an understanding of urban ecosystems functioning and interactions amongst the built and natural environment (climate) and human systems. In this paper we argue that learning is essential for cities to be resilient to current and future challenges. We profile the Future Resilience for African CiTies And Lands (FRACTAL) project which contributed towards climate resilient development by providing relevant climate information for decision-making at the city regional scale in southern Africa. Following FRACTAL's city-to-city learning approach of sharing good practices, knowledge and experiences framed around transdisciplinary research, the study cities of Harare, Lusaka, Windhoek and Durban conducted city learning exchange visits between 2017 and 2018. We used a mixed methods approach to collect and analyze historical climate and hydrological data and current socio-economic and development data among the cities. A qualitative, in-depth, case study comparative analysis was used to identify similarities and differences as well as lessons drawn from the learning process during the city exchanges and these were complimented by desktop studies. Results showed water scarcity, large informal settlements, reliance on external water and energy sources, inadequate protection of ecologically sensitive resources and service provision as some of the common complications in the cities. Several lessons and transferable practices learnt from the cities included effective water conservation and waste management and the use of public-private partnerships in Windhoek, community engagements in Durban and Lusaka while lessons on decisive leadership in dealing with informal settlements emanated from Harare's limited informal settlements. Lastly, Durban's Adaptation Charter and integrated climate planning provided lessons for biodiversity protection and mainstreaming climate change at city governance level. While we recognize that cities are context-specific we consider these good practices as being broadly transferable to other southern African cities. We conclude that social, experiential and structured learning can be an innovative way of multi-stakeholder engagement and a useful approach to increase city resilience planning across southern Africa and cities that face similar developmental challenges. [ABSTRACT FROM AUTHOR]