This study conducted 28 semi-structured, in-depth interviews with Young Black Men who have Sex with Men in Chicago to investigate the impact of COVID-19 on their HIV care and ancillary service access. The qualitative analysis identified both negative and positive effects. The negative effects included: (l) mixed disruptions in linkage to and receipt of HIV care and ancillary services, and (2) heightened concerns about police and racial tensions in Chicago following the murder of George Floyd, contributing to possible disruption of retention in care. The positive effects included: (1) the ability to reflect and socially connect, contributing to heightened self-care and retention in care, and (2) some improvements in receipt of medical care. These findings suggest that while COVID-19 disruptions in care reduced in-person use of HIV care, the expansion of telemedicine allowed more administrative tasks to be handled online and focused in-person interactions on more substantive interactions.