This study investigates how the college readiness of participants in a compensatory program designed to facilitate interest in science and engineering was determined. Archival data were used to qualitatively analyze the performance reports of 205 student participants during the compensatory program’s first 5 years. Findings indicate participants were evaluated favorably for maintaining a positive disposition toward coursework regardless of their actual numeric scores. Consequently, many participants, whose numeric scores made them less viable candidates, were recommended for admission to college. Because 95% of the students participating in the program were African American, this article highlights how context-specific evaluation can reduce biases encountered by this population when colleges rely on traditional measures of achievement to determine college readiness.