The transition into high school is a critical time to act for students with a history of academic difficulty. In this study, researchers examined the impact of a learning strategies intervention program called High School Success on performance of students demonstrating deficits in literacy and academic skills. Data were collected on performance in a 9th grade English course, an associated high-stakes literacy test, and subsequently their long-term rates of graduation following this unique 9th grade experience. Chi-square analysis comparing the treatment group (n = 428) who participated in High School Success to a control group of at-risk students not exposed to the intervention course (n = 629) revealed a significant impact (X[superscript 2] (df = 1) 28.02, p < 0.001) on whether students dropped out of high school. The data revealed that students in High School Success had statistically significantly better achievement and rates of high school graduation. These results provide evidence for ninth grade literacy and learning interventions as primary strategies for easing transition into high school and increasing retention of students with a history of academic difficulty.