The commitment to understanding the implications of a 1.5 °C global temperature warming limit has contributed to a growing realisation that transformative adaptation is necessary to avoid catastrophic environmental and social consequences. This is particularly the case in urban settlements where disconnection from the systems that support life is pervasive and injustice and inequality play out daily. This paper argues that in order to transform towards thriving social-ecological systems, transformative capacity needs to be strengthened. The paper builds on the rich literature of adaptive capacity, alongside concepts of transformation that are drawn from resilience theory, organisational change, and developmental psychology. Reconnection to life-support systems, agency, and social cohesion are put forward as three foundational aspects of transformative capacity. A transdisciplinary case study of the FLOW programme in the Bergrivier Municipality, South Africa, is used to explore how transformative capacity has been built in practice. The case study explores an innovative programme that works with unemployed urban youth, alongside the exploration and introduction of a community currency in the informal business sector, and strengthening cross-scalar interaction between the local municipality and youth. The paper suggests that working across sectors and scales in a transdisciplinary manner is a challenging endeavour but necessary for building inclusive, thriving, and regenerative urban settlements.