The purpose of this study was to gain a better understanding of early preparation for postsecondary education and explore the effectiveness of Gaining Early Awareness and Readiness for Undergraduate Programs (GEAR UP). This comparative case study included 836 students from two cohorts (GEAR UP and Non GEAR UP). We compared high school attendance, retention, behavior incidents, GPA, graduation rates, and college attendance by GEAR UP, socioeconomic status, and race. GEAR UP students performed significantly better on all measures. There were differences found in both cohorts along SES and racial lines; these differences were less pronounced within the GEAR UP cohort. Recommendations for school reform, collaborations between education institutions, and further research are included.