Since 2001, the San Colombano Project has provided the College-Bound Tutoring program for disenfranchised prospective first-generation college students in a southwestern community of the United States. However, an evaluation of the program had never been conducted. The purpose of the study was to conduct a qualitative, responsive program evaluation in a naturalistic setting using a case-study approach with a constructivist lens to create a narrative portrait of the program. Guided by critical race theory, Vygotsky's zone of proximal development, and Wlodkowski's motivational theory, the study explored the effectiveness of the program. Interviews were conducted and archival data were examined to understand the effectiveness of the program. Interview participants included 5 leaders, 4 alumni/staff members, and 2 adult volunteer tutors. Typological, inductive, and content analyses were applied to the contextualized data. The findings arising from data analyses were based on these themes: (a) authentic hope, (b) social and emotional learning, (c) organizational leadership, and (d) creation of a college completion culture. To promote social change, a program evaluation was provided to San Colombano Project based on these findings. Social change may be achieved through implementation of the program evaluation on behalf of these disenfranchised students by (a) embedding promising practices; (b) extending learning and growth opportunities; (c) leveraging data to improve, sustain, and embed processes; and (d) applying recommendations for enhancing an organizational learning culture.