The Student Trajectory Enhancement Program (STEP UP) was launched in 2014 by Hillsborough County Public Schools (HCPS) as a six-week summer program that targeted over-age, retained, potentially under-achieving students completing the sixth grade. The purpose of this study was to conduct a summative evaluation of the effectiveness of the STEP UP program in keeping program participants “on track” for high school graduation and to determine if the intended goals of the program were realized. STEP UP was developed in response to compelling data that there is an unacceptably high number of overage students in middle school in HCPS. STEP UP was intended to decrease the number of potential dropouts in HCPS, with the assumption that a number of students who drop out of high school originate as overage students in the elementary and middle grades. The evaluation focused on students who participated in the initial cohort in the summer of 2014. Data analyzed were students’ attendance, behavior, course performance, and grade point averages—the district’s Key Performance Indicators (KPI’s) serving as the benchmark for determining whether students are “on track” to graduate. Findings of the study suggested that students’ “on-track” performance on individual KPI metrics was significantly higher than the overall “on-track” performance on all Key Performance Indicators as an aggregate. Data reflected that the majority of students in the program were minority (78.74%), designated as Free/Reduced Lunch (91.27%), and classified as ESE and ELL (54.09%). Of the variables studied (ethnicity, gender, ESE status, ELL status, and FRL status), students in poverty and students with profound exceptionalities had the lowest “on-track” performance rates. While there were differences in individual KPI performance rates among ethnic groups, there was little difference among the three largest ethnic subgroups in the data set (Hispanic, white and African-American) when analyzing “on-track” performance rates for all KPI’s together. This study contributes to the school district’s ability to make improvements to the program. In addition, other districts might gain insights to help them determine if a similar program could prove beneficial for their overage, retained students in middle school.