Background/Context: In-school racial segregation, also called second-generation segregation, is a social dynamic that is manifest in different and complicated ways in schoolhouses across the United States. This study sought to investigate how building-level leadership facilitates or impedes the practice of racial equity in an urban high school, from teachers' and administrators' perspectives. Purpose: The primary purpose of this exploratory study was to investigate how educational leaders perceive and influence second-generation in urban secondary schools. Research Design: As the purpose of the study was to ascertain leaders' perspectives, we followed a dialogic methodological approach used in studies seeking to investigate similar perceptual phenomena. This methodology emphasizes both personal narrative and dialogue. This study took place in a single urban high school in the Southeastern United States over the course of two academic years. Conclusions/Recommendations: The study revealed that both formal and informal leadership influenced second-generation segregation in the school. The authors conclude with recommendations for improving future research focusing on the topic and with recommendations for improved practice.