Vengeance has been shown to be a risk factor for HIV nondisclosure. Research examining the associations between vengeance, condomless sex, and HIV nondisclosure is lacking. The aim of the current study was to explore the association between vengeance, condomless sex and disclosure (behavior, attitude and intention) among men who have sex with men (MSM) living with HIV. Participants included 266 MSM who were a part of a disclosure intervention study. Men were recruited from local and state AIDS service organizations (ASOs), HIV-related venues and forums, and at local eating and drinking establishments in Tampa, Florida, and Columbus and Dayton, Ohio metropolitan statistical areas (MSAs). Advertisements were also placed in local daily newspapers. Vengeance was operationalized into three groups based on percentiles (least, more, and most vengeful) and as a continuous variable. Crude and multivariable logistic regression models were used to examine the association between vengeance and condomless sex in the past 30 days. Simple and multiple linear regression models were used to determine the association between vengeance and HIV disclosure. After adjusting for demographic and geographic characteristics, participants who were “most vengeful” had, on average, an approximate six-point decrease (β: −5.46; 95% CI −9.55, −1.36) in disclosure intention compared to MSM who were “least vengeful.” Prevention and intervention programs geared towards improving disclosure among MSM should address vengeance.