Marginalized adults have limited access to learning experiences that prioritize reflection and discourse, both considered preconditions in the Mezirow-informed field of transformative learning (TL). Using narrative analysis of a staff focus group and participant interviews over a 1-year learning journey, this study shows how a literacy program in a women's homeless shelter created conditions that supported TL for two marginalized women of color. Results show how program learning goals were attuned to issues of positionality for women marginalized by race, class, and gender and were consistent with Africentric womanist epistemological and axiological assumptions. Conditions that fostered connectedness among women in troubling contexts and contributed to qualitative change in ways of knowing included purposeful spaces dedicated to reflection, dialogue, and student-centered pedagogy. The findings have important implications for the theoretical grounding of policy and practice in support of marginalized women's TL.