The transition period of a student from middle school to high school is of critical importance because students who can successfully navigate the first-year physical, academic, and social pressures of high school have the greatest chances for successfully completing high school in four years (Allensworth & Easton, 2005). Students who cannot successfully overcome transition barriers are at greater risk of dropping out of school and thus experiencing lower economic and social potential in their lives (Nield, 2009). The importance of a successful freshmen year transition has led high schools to develop many different student academic interventions. However, there is no recognized best practice intervention systems that have been developed. This dissertation examined the use of a pre-freshmen-year Summer Academy that provided academic and social interventions to identified at-risk students. The goal of the Summer Academy was to provide extended teaching and learning opportunities during the summer to at-risk students to enhance the skills needed for high school success. The results of this causal-comparative ex post facto study showed that students enrolled in the program did not experience any significant changes in academic grades, standardized tests scores, or participation rates in extracurricular activities compared to peers who did not participate in the program. However, the data did show positive trends in course grades for program participants, suggesting a need for further study. Considerations for schools and future research on high school transition programs are discussed, specifically instructional and social-emotional curriculum changes that may enhance a pre-freshman year Summer Academy program. [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.]