This article examines a recent reform effort that has opened hundreds of small high schools in poor urban communities in New York City, The New Century Schools Initiative (NCSI). Founders hoped that the small schools strategy would create personalized environments where relationships could develop between teachers and students, leading to improved outcomes for poor students and students of color. Looking at three of the NCSI high schools in the Bronx, this ethnographic study reveals that small school size does not always lead to relationship-building between teachers and students. Teachers need support and training which is currently missing from NCSI's theory of action. The study suggests that NCSI can be strengthened with incentives and support for teachers to develop relationships with their students.