Each year approximately 1.3 million students dropout of high school and an estimated 40% of minority students do not graduate on time (Roybal, Thornton, & Usinger, 2014). In high school, 22% of students repeat 9th-grade classes because students fail to make a smooth transition. This gives the 9th-grade the highest enrollment rate and the highest dropout rate (McCallumore & Sparapani, 2010). In an effort to increase high school graduation rates, the Peabody County Public School District created Achievement schools, an initiative to recruit highly effective administrators, teachers and staff members to support students with the highest academic and nonacademic needs. This study examined school administrators' perceptions of middle school students transitioning to Achievement high schools. The purpose of the case study was to examine how school administrators perceived an ideal 9th-grade transition, challenges 9th-grade students faced through transitioning, and the vision of a successful 9th-grade transitioning to an Achievement High school. This study focused on a group of Achievement high school administrators and the middle school administrators at their respective feeder schools. I utilized qualitative methods to analyze the administrators' perceptions collected through individual interviews about their views of best practices for student transitioning. The findings of this study can contribute to the overall evaluation and aid in establishing policies and programs to assist with 9th-grade transitioning. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]