This study explored the influence of mentoring on the future expectations of youth, comparing those with and without an incarcerated family member. Using data from the Big Brothers Big Sisters of Metro Atlanta program, it investigated initial differences in educational and future expectations and how these evolve through mentoring. It hypothesized that mentoring would significantly benefit youth with incarcerated family members. A longitudinal design assessed the impact of mentor-mentee relationship quality, youth engagement, and perceived competence/autonomy. Results showed that high engagement in mentoring improved educational expectations after six months, while mentors' perceptions of youth competence/autonomy enhanced future expectations over 12 months. Having an incarcerated family member did not significantly alter these relationships. The study highlighted the importance of high-quality mentoring and suggested further research into culturally responsive programs for youth with incarcerated family members, emphasizing the need for detailed measures and rigorous data to understand mentoring's long-term impact.