Young Black men who have sex with men (MSM) living with HIV evidence the lowest rates of linkage to care and viral suppression of all US MSM. Kentucky, identified by the US Department of Health and Human Services as a “hot spot” state with elevated HIV incidence compared to the rest of the country, exhibits similar racialized outcomes. Structural, interpersonal, and individual drivers of engagement along the HIV care continuum among people living with HIV have been identified, primarily through quantitative designs. However, the mechanisms by which these factors shape HIV care engagement, and the ways they may combine or reinforce each other, as well as from the lived experience of young Black MSM living with HIV, have been studied to a lesser extent. In this study, a purposive sample of n = 29 HIV-positive young Black MSM (age M = 25 years old; 38% retained in care) residing in Kentucky participated in in-depth interviews. Factors that were most influential on engagement varied along the continuum, with health insurance status and knowledge of HIV being relatively more influential to diagnosis, and housing stability, psychological processes, and interpersonal relationships being more influential on retention. For some participants, barriers to care at multiple levels had a mutually influencing and intensifying impact on care engagement. Additional efforts to center the voices of young Black MSM living with HIV will help illuminate acceptable and sustainable interventions for increasing their care engagement and narrowing persistent racial disparities in HIV morbidity and mortality.