The purpose of this study was to investigate how former Upward Bound students’ experiences may have influenced their high school completion and college readiness to bridge the opportunity gap. This study describes the personal experiences of former Upward Bound students and current staff to understand how a specific Upward Bound Program assists its students with being college ready. The results gathered provided indications about how the Upward Bound Program influenced the students’ transition from high school to college. The main data collection method was the use of interviews. Qualitative research methods were used to explain the data gathered from the interviews. The results of the study suggested that the Upward Bound Program positively influenced its students through the activities, awareness, and support provided by the staff to impact the opportunity gap.