Background: For decades, scholars have argued that teaching and learning depend funda–mentally on the quality of relationships between teachers and students, yet there is little research about how teachers develop relationships with students or how teacher education prepares teachers to do this work. Arguably, articulating the relational practices of teaching is critical for those aiming to prepare teachers to reach across differences, educate from a social justice perspective, and teach an increasingly diverse population of students. Noting the emphasis on relationships in community–based organizations (CBOs), the authors investigated preservice field placements in CBOs as potentially strategic contexts for learning about relational aspects of teaching. Objective: The authors engaged the questions: What do candidates learn in CBO field placements? What are sources of variation between candidates’ learning outcomes? What are individual and contextual factors that shaped candidates’ opportunities to learn in CBOs? Specifically, which factors influenced candidates’ inclination and capacity to enact relational teaching practices (e.g., the methods and skills associated with learning about and connecting with students, families, and communities)? Research Design: This study was a 3-year longitudinal investigation. Authors followed two cohorts of candidates from their first quarter of preparation into their first year of teaching. Qualitative methods, such as interviews, observations, and document review were employed in this inquiry of 12 case study candidates. To examine questions of variation, authors also conducted an in-depth comparative case analysis of a subset of two candidates and their CBO placement contexts. Findings: CBO placements facilitated opportunities for candidates to “see students”: candi-dates developed deeper understandings about children and more nuanced conceptions of diversity; experienced and examined school from an out-of-school perspective; and demon-strated greater attentiveness to the role of context in learning. The more detailed compara-tive analysis of two cases revealed variation in candidates’ experiences and their enactment of practices involved in building relationships with children and families. This analysis identified individual and situational factors (in coursework and CBOs) that facilitated and impeded candidate learning in CBOs. Conclusions: Findings from this study highlight the types of learning outcomes that preser-vice community-based placements potentially afford, as well as factors that make some place-ments more educative than others. The authors offer a theoretical lens that attends to variation in learning, which could be leveraged in future empirical work. This research con-tributes to the field’s developing efforts to identify key social justice teaching practices and to conceptualize pedagogies of enactment for such practices.