Objective: This study examines whether disparities exist in poor health and depressive symptomatology among older gay/bisexual men (50+) with (n = 371) and without (n = 973) HIV. If so, what risk/promoting factors account for those disparities? Method: These cross-sectional analyses used 2014 data from the Aging With Pride: National Health, Aging, and Sexuality/Gender Study. Results: Those with HIV reported poorer health and more depressive symptomatology accounted for by lower income, resilience and social support, and more lifetime victimization. Poorer health among those with HIV was associated with more chronic conditions. Higher depressive symptomatology was associated with diagnosed anxiety and drug addiction. Community engagement reduced disparities in poor health and depression. Implications: Older gay/bisexual men living with HIV infection are at greater risk for physical and mental health issues. Assessments should be conducted with attention to these risk factors. Interventions for improving social support, resilience, and community engagement are warranted.