Because dominant social work is mismatched to many contexts, alternative practice and educational approaches have emerged. To highlight educational examples, this phenomenological study explores the experience of 28 Canadian and South African educators teaching alternative social work. These educators conceptualized a multidimensional, integrated, contextualized framework that attends to power and resistance, and extends critical social work education by its focus on the local context. Their pedagogy included experiential, intentional, relational, reciprocal, and participatory, dialogical, land-based, reflective, and reflexive aspects. Their accounts illuminate the importance of developing personal intent, appropriate policy environments, adequate resourcing, and an activist social work body toward entrenching contextualized social work education. Considerations for implementing contextualized social work education in other contexts are discussed.