Thesis advisor: Marilyn Cochran-Smith / The clinical experience of future urban teachers is increasingly regarded as one of the most important aspects of teacher preparation (NCATE, 2010; NRC, 2010). However, there is widespread agreement that further knowledge must be acquired on what constitutes rich clinical experience, and on the influence of such learning opportunities especially in urban, high-needs contexts (Anderson & Stillman, 2013; Levine, 2006; Picus, Monk, & Knight, 2012). This dissertation aims to increase our understanding of clinical experience. Based on sociocultural and socio-constructivist perspectives, and drawing on Lave and Wenger’s (1991) theories of learning within communities of practice, this dissertation employed qualitative research methods to examine the phenomenon of content coaching during an urban teacher residency program. This dissertation argues that residency content coaching provided a context within which residents could integrate what they were learning about “ambitious teaching” (Lampert & Graziani, 2009; Newmann & Wehlage, 1993) into their own practice through ongoing negotiations with their coaches. Coaching interactions were by and large responsive to individual resident’s learning needs, and guided residents to begin to place their students’ learning at the center of decision-making when planning, teaching, and assessing. The dissertation further investigates the actual and aspirational characteristics of coaching in this context. Overall findings suggest that content coaching addresses several persistent problems of traditional pre-service fieldwork supervision (Darling-Hammond, 2010; Featherstone, 2007), and offers a more coherent approach. Consequently, this dissertation contributes to our collective understanding of clinical experience in preparing teachers to teach ambitiously in urban classrooms. / Thesis (PhD) — Boston College, 2016. / Submitted to: Boston College. Lynch School of Education. / Discipline: Teacher Education, Special Education, Curriculum and Instruction.