In this article, the author uses insights gained from reflection on a qualitative research project to raise issues about the introduction of preservice teachers to urban schooling. In particular, she examines her experiences as a White, middle-class researcher as she conducted research with students of color in a poor urban school and community. She documents the ways her roles and relationships inside the research project shifted and how issues of power and control became more apparent as she followed students from school to their workplaces and community settings. She uses this analysis to raise questions about what happens when a predominantly White, female, middle-class group of preservice teachers from the suburbs is introduced to the challenges and rewards of teaching in urban settings. She suggests the need to transform the roles and relationships between students and teachers, particularly with respect to issues of race and class in teaching and research.