© 2019, Springer Nature B.V. This research explores the agent dynamics, learning processes, and enabling conditions for the implementation of microscale win-win solutions that contribute to energy poverty eradication and climate resilience in a selection of low-income rural and peri-urban communities in India, Indonesia, and South Africa. We define these micro-solutions as energy-related interventions and resilience services or products—used at community, household, small production unit, or business level—that yield both economic and climatic gains. Our analysis identifies five elements critical for the robust design of these interventions: (i) The ability to collaborate and share different kinds of expertise with a range of networks operating at multiple levels of activity; (ii) The application of place-based systems-learning perspectives that enable project participants to integrate different types of solutions to meet different needs at the same time; (iii) The ability to yield tangible short-term benefits as part of long-term strategic visions and commitment; (iv) The use of novel technologies and financial instruments in ways that foreground the needs of poor populations; and (v) The inclusion and empowerment of economically marginalised groups through institutional and technological innovations and responsible business models. We conclude that the most critical aspect of successful micro win-win solutions is support for communities’ own endogenous transformative capacities as this helps ensure that solutions are shared and continuously adapted to changing conditions over time.