Engagement in HIV care is critical to achieve viral suppression and ultimately improve health outcomes for people living with HIV (PLWH). However, maintaining their engagement in care is often a challenging goal. Utilizing patient navigators, trained in an adapted ARTAS intervention, to help re-engage out-of-care PLWH has proven to be a valuable resource. This qualitative study describes the encounters between PLWH (n = 11) and their care re-engagement navigators (n = 9). Participants were interviewed in-person; interviews were transcribed and analyzed using the strengths model of case management. PLWH shared how working with navigators increased their motivation to return to HIV care and assisted them to overcome barriers that were a hindrance to care engagement. Navigators described a strengths-based approach to working with their clients, thus helping facilitate PLWH care re-engagement goals and successes. Results from this study may inform the development of effective HIV navigation programs to re-engage out-of-care PLWH, often the hardest-to-engage.