<p>This phenomenology explored the mentoring experiences of children and adolescents with incarcerated parents participating in the 2023 Visiting Mentoring Program in South Korea. The research aimed to illuminate mentees’ experiences and relationships within the structured program to offer guidance for implementing mentoring initiatives that foster positive outcomes and successful adaptation. Nine mentees and four mentors participated in in-depth interviews, which were analyzed through thematic analysis and phenomenological methods using the Family Stress-Proximal Process model as a theoretical framework. Findings uncovered that mentees experienced emotional and personal growth through close relationships with mentors and peers, enjoying new activities that fostered social skills, self-determination, and career aspirations. Mentors served as sources of joy, positive adult role models, and trusted confidants, to whom mentees disclosed personal stories and challenges, including those related to their incarcerated parents. These relationships helped mentees overcome societal stigma, develop a sense of hope, and envision stable futures. The program was a turning point for many mentees, filling emotional voids and fostering a sense of liberation from societal labels. While highlighting positive developmental outcomes for mentees that emerged naturally, the study suggests the need to clearly define mentors’ multifaceted roles in cultivating long-term, supportive relationships. These findings underscore the potential of well-structured mentoring programs to positively impact vulnerable populations and provide actionable insights for program development.</p>