Black and African American men who have sex with men (Black MSM) experience the greatest proportion of new HIV infections in the United States. To address this challenge, a better understanding of the HIV environment riskscape including both risk and resilience factors is warranted among Black MSM. Research indicates that stress is associated with increased HIV sexual risk behaviors. Further, behavioral factors such as serosorting and community level factors including social support and community connection are resilience factors that protect against risk behaviors. The present study examines whether everyday stress is associated with HIV sexual risk behavior, as well as the role of risk and resilience factors among 125 Black MSM recruited in the Real Talk study. The Real Talk project examined the relationships between resilience, HIV risk behaviors, and HIV prevention strategy among a sample of Black MSM. Using generalized estimating equations, our results indicate a positive association between everyday stress and engaging in condomless anal intercourse only after adjusting for risk, resilience, and correlate variables. Similarly, having multiple sex partners and using substances during sex also show positive associations with condomless anal intercourse. Resilience factors of engaging in serosorting and being connected to both the Black and gay communities were negatively associated with condomless anal intercourse. Future prevention research and programming should focus on both risk and resilience factors to mitigate new HIV infections among Black MSM.