This book provides an autobiographical and research-based exploration of the perceptions of Black middle and upper class preservice teachers about teaching and learning in high poverty urban schools. While there is an extensive body of knowledge on White preservice teachers, limited studies examine Black middle and upper class preservice teachers who may also lack experience with students in high poverty urban schools. Through this narrative, the author explores her own professional journey and a research study of former students who experienced the same boundary crossing. Their voices add to the body of current knowledge of how race and class affect the perceptions of preservice teachers.