This article shares findings from a qualitative study of an undergraduate urban education fellowship designed to connect teacher-candidates with activist teacher communities and explore questions of social justice, equity, and multicultural teaching. Fellows attended conferences, professional meetings, and on-campus dialogues over one semester. Interview transcripts and meeting notes were analyzed through the lenses of teacher inquiry and transformative learning theory. Findings reveal how teacher-candidates experienced shifts in their viewpoints through encountering new perspectives, discomfort with returning to their lives with new understandings, and a strong drive to further their learning about urban education. Within the context of a persistent gap between a mostly White, middle-class teaching force and a racially and socioeconomically diverse student population, this study offers an image of transformative preservice teacher education in which teacher-candidates encounter professional communities outside of the confines of the classroom.