The story of the past 15 years in U.S. education has been one of fundamental reform and transformation. These changes are felt most acutely in the daily lives of teachers and principals and often have lasting effects on the context of the school community. This case study explores the challenges facing a principal when attempting reform and improvement efforts set in a larger backdrop of social and economic change. This case involves issues related to understanding school context and improving communication skills for new principals and can be used for principal preparation and educational leadership courses.