The complexities and uncertainties of social entrepreneurs' worlds require them to juggle social and business aims. Using social theories of learning, we provide a deeper understanding of learning within social entrepreneurship education. Programs aimed to develop reflective thinking and communities of practice to equip social entrepreneurs for their unique circumstances. Two programs are compared and the implications of social and commercial entrepreneurs learning together are examined. Challenges and successes in the cultivation of a community of practice reveal the importance of learner identity and psychological safety. The paper culminates with key principles for educators of social entrepreneurs.