Drawing from the experiences and reflections of new urban educators, this study examines how teachers undergo their first year of teaching on account of their student teaching. Using "Situated Learning Theory"--with an emphasis on legitimate peripheral participation--this study explores how sociocultural and contextual elements of schools contribute to teacher development. Findings suggest that teachers who complete student teaching in environments that mirror their first-year school placements feel more confident and competent in their ability to teach and serve students than teachers who complete student teaching in environments that do not match their first-year school placements. Implications for urban teacher preparation and student teaching placement are discussed.