In times of climate change, the possibility of regenerative futures is deeply intertwined with the potential of healing the Earth and her people. Climate change adaptation, resilience, and transformation all signal the need to reframe the way we live at intersections of complex past(s)-present-future(s), i.e. to co-create regenerative cultures and futures. This chapter focuses on the cultural dynamics of how we might do this, with an emphasis on mobilising possibility knowledge in and through expansive learning processes. Possibility knowledge occupies a liminal space in the transitions that emerge from challenges and contradictions in life worlds. The chapter offers a case of co-creating regenerative agro-ecological practices in South Africa amongst historically marginalised climate-affected communities. It surfaces seven different types of possibility knowledge that are dialectically related. It argues that possibility knowledge can offer ways of thinking about environmental education processes that respond to climate change through open process approaches of learning ‘what is not yet there’. Possibility knowledge would necessarily differ from context to context due to the ontological-axiological and agency-centred nature of such knowledge which helps to re-think top-down and techno-centric models of environmental and climate change education most often based on the transfer of stabilised categorical knowledge.