Researchers target 9th grade as the make or break year for completing high school. During the 9th-grade year, many students for the first time have to earn passing grades in core courses, and these core courses are typically some of the toughest and most rigorous academic classes a student must take in high school. Furthermore, the rising use of standardized tests to measure school performance, and exit exams required to earn a diploma add to the difficulty and importance of doing well in high school. Statistics generated from freshman year are concerning. Ninth graders have the lowest grade point average, the most missed classes, the majority of failing grades, and more misbehavior referrals than any other high school grade level. The 9th grade also has the highest enrollment rate in high schools, mainly due to the fact that approximately 22% of students repeat 9th-grade classes. This number can be even higher in large urban high schools. While the transition from middle school to high school can represent an important milestone, it can also be a time of loneliness, isolation, and disconnection for some students. This transition period is frequently marked by declining academic performance, increased absences, and increased behavior disturbances. These factors put freshmen more at risk than any other school-aged group. The differences, both academically and socially, between middle school and high school make the transition difficult. The authors contend that it is important to consider what can be done in middle school to better prepare students for new challenges and also important to not drop the ball on students after 9th grade, but to continue support during their remaining high school years. This article discusses some solutions to ease transition.