In this article, I employ sociocultural theory to analyze the learning to teach process of two novice teachers enrolled in one Urban Teacher Residency (UTR). Findings show that Genesis and Jackie were differentially drawing on programmatic, disciplinary, relational, experiential, and dispositional resources as they learned to teach in an urban context. I show that programmatic resources of supervision and classroom management requirements (i.e., Doug Lemov’s Teach Like a Champion) not only differentially influenced teachers’ learning and development but also differentially impacted the development of trust with students.