Dropping out of high school has negative results and implications for individuals and society. The likelihood of dropping out is attributed to both social and academic risk factors. Poor high school attendance, low course completion, and low grade-point-average (GPA) have been identified as three leading indicators that students are at risk for dropout. Early identification of at-risk high school students is critical during the first semester of ninth grade. This study utilized a single case study design with embedded quantitative statistical analyses to understand the characteristics of 416 students transitioning from three middle schools to a large suburban high school. Regression analyses were used to examine the relationship of 12 middle school indicators to ninth grade attendance, course completion, and GPA. Findings indicated that middle school GPA, grades, attendance, and ACT math scores were all strong predictors of ninth grade performance. Using these middle school risk indicators, ninth grade students at risk of school failure may be identified early and provided interventions during their first year of high school.