The purpose of this case study was to examine the supports provide by school leadership to academically and socially prepare ninth grade students for high school. A quarter of students who endeavor to make academic and social progress are those who have just transitioned to high school as, ninth-grade students. The study used the qualitative case study methodology. For this purpose of this study, the case includes the school leaders and grade-level teachers at one middle school and one high school to examine various elements of the eighth to ninth grade transition. Through the interviews of 14 participants the researcher was able to explore and analyze leaders’ expectations for ninth grade students, and how those expectations shape the academic and social difficulties for ninth-grade students. The data from the 14 participants provided evidence that there warrants further examination for further examination of the ninth grade transition process at to foster academic and social preparedness of ninth grade students. This study found that there is a clear lack of systems and resources present for ninth grade students to academically and socially prepare for ninth grade. The implications of this study were offered to promote student academic and social success. These implications can serve to prevent further decline in the academic and social preparation of ninth grade students. The struggle to successfully transition ninth grade students into high school is indicative of the additional attention and resources needed for ninth-grade students.