Rebecca Ashe, a first-year mathematics teacher at North Hills High School, considered herself well-prepared after her university preparation. She is energetic and dedicated to her students, providing real-world examples in her classes from past experiences as an engineer. After 3 months in the classroom, however, Rebecca had become disheartened and exhausted. Moreover, Rebecca felt her school principal, Andy Anderson, had provided only superficial support. This case study explores obstacles that early career teachers face and asks readers to consider strategies that school administrators can employ to support these teachers. This case is suited for use in administrative preparation courses, specifically those focusing on human resources, evaluation, leadership, and supervision.