This case traces the involvement of a principal of an Early College High School (ECHS) and her understanding of performance of Latina students attending the school. Latina students are the lowest academic performers in the ECHS, despite the school obtaining high accolades in terms of accountability. To best understand the phenomena of underperformance of Latina students, the principal hires a consultant. The consultant discovers aspects of the ECHS and aspects of schooling as experienced by the Latina students that contribute to underperformance. The case raises important issues for aspiring leaders, making it an excellent example of the complexities embedded in student achievement.