As black women over age 50 represent a growing share of women living with HIV, understanding what helps them persist and engage in ongoing HIV care will become increasingly important. Delineating the specific roles of social support and stigma on HIV care experiences among this population remains unclear. We qualitatively examined how experiences with stigma and social support either facilitated or inhibited engagement in HIV care, from the perspective of older black women. Semi-structured interviews were conducted with 20 older black women currently receiving HIV care at primary care clinics in the Metropolitan Boston area. Women expressed that experiences with stigma and seeking support played an important role in evaluating the risks and benefits of engaging in care. Social support facilitated their ability to engage in care, while stigma interfered with their ability to engage in care throughout the course of their illness. Providers in particular, can facilitate engagement by understanding the changes in these women's lives as they struggle with stigma and disclosure while engaging in HIV care. The patient's experiences with social support and stigma and their perceptions about engagement are important considerations for medical teams to tailor efforts to engage older black women in regular HIV care.