In comparison to resident fathers, non-resident fathers face formidable challenges in maintaining a consistent presence in their children’s lives. Such challenges tend to exist on multiple contextual levels--intrapersonal, interpersonal, neighborhood, community, cultural, and societal. We conducted semi-structured, qualitative interviews with a sample of eight participants who identified as an African American, biological, non-resident father to at least one child, ages 5–17. We explored barriers and facilitators to their involvement on five contextual levels—self, co-parenting, family, social/community, and societal. We employed a phenomenological methodology which revealed numerous barriers to involvement with children, including the father’s own personal lived experiences, conflictual co-parenting and family dynamics, engagement in the street lifestyle, and challenges with parenting across multiple households. Findings also revealed several supports to involvement with children, including the father’s determination to be involved and growth mindset toward fathering, positive and supportive co-parenting relationships, family support, and fatherhood programs. The results of this study are intended to provide contextually-based insights for service providers that can be translated into service delivery and applied to programs that focus on eliminating barriers and increasing supports to father involvement, thereby improving child well-being and enhancing family functioning.