In a longitudinal design experiment conducted within an urban teacher preparation program, we employed ethnographic and auto-ethnographic methods to investigate the following questions: 1) In what ways do clinical experiences (CEs) support prospective teachers' (PTs) development of knowledge, skills, and dispositions necessary for urban teaching? 2) How is it determined that adjustments need to be made to the design and facilitation of CEs, and what did these adjustments yield in terms of student learning outcomes? The program centers and leverages CEs in order for PTs to connect theory and practice, particularly an awareness of, and skills associated with, equitable teaching practices. In our two-year field-based program, CEs included community explorations, one-on-one and small group work with children, two student teaching practicums, and various school-community events. We describe the process undertaken to maximize the benefits yielded from CEs. After working with three cohorts of PTs for their entire professional training, we found that: 1) focusing attention on the intentional design and assessment of the mediational activities coupled with CEs leads to more nuanced understandings and enactments of culturally relevant teaching among PTs; and 2) CEs afford PTs abundant opportunities to shape complex identities as urban teachers. Specifically, we found that clinical experiences and corresponding mediational activities support PTs' understanding of families of color, allow them to recognize and address problematic schooling practices, and strengthen PTs' otherwise fragile critical consciousness. We conclude that strategic interventions can provide clarity for PTs around what has been learned, and what is left to be developed.