Student retention is an issue of perennial interest to educational institutions and is frequently a focus of pedagogical research and evaluation of programming, although some recent literature on factors affecting college student retention recommended attention to academic preparedness and student engagement as key variables influencing college student retention. This study explored the barriers and facilitators of retention and attrition of Helping Youth Pursue Education (HYPE) program participants in regular college programming, and the role of service supports and mentorship in improving the college experience of youth from underserved neighbourhoods. The qualitative research focused on how gains in interpersonal and problem-solving skills and connecting with one or more mentors at the College related to student success. The analysis revealed that, while the current program delivery model has resulted in steady improvement in outcomes relating to application, admission and student success for those who are ‘ready,’ more could likely be done to improve participant experience and outcomes. Recommendations for improvement focused on strategies for the early identification of HYPE program participants likely to enter post-secondary education, faculty and staff development to enhance program delivery, and consideration of other program amendments to improve outcomes. Further work is needed to explore reasons why students do not follow-through on their learning plans, and to find ways to encourage them to do so.