This study investigated psychosocial and demographic variables that might influence internalized homonegativity (IH) in midlife and older gay and bisexual men (GBM). Data were collected from 802 community-dwelling GBM aged 40 to 94 years ( M = 54.8) through an anonymous questionnaire that assessed levels of IH, coping self-efficacy, self-silencing, and other characteristics. Multivariate logistic regression analysis successfully explained 22% of the variance in predicting IH, which was significantly related to coping self-efficacy, self-silencing, gay community volunteering, partnership status, and race, F = 59.74, p < .001. IH scores were highest in participants who were single, had lower education levels, were non-White, were less involved in gay community volunteering, experienced less coping self-efficacy, and reported higher levels of self-silencing behaviors. These data underscore the need for more tailored programming approaches for midlife and older GBM, focusing on underlying factors contributing to IH that include skill-building to increase coping self-efficacy, community involvement, and decrease self-silencing behaviors in this overlooked population.