The transition from middle school to high school poses as one of the most challenging transitions students will make in their academic career in grades K-12. The transition from grade eight to grade posts the greatest loss with the highest dropout rates nationally occurring during this transition. This book shares authentic examples through story telling of the situations students have experienced during their transition to high school. Also included in this book are intervention strategies schools could implement to counter the downward spiral. This book opens dialog and increases communication among teachers, parents and administrators with the goal of seeking solutions and implementing transition activities that increase the chances of student and school success.