Within the broadly generalized HIV epidemic in Swaziland, men who have sex with men (MSM) have specific HIV acquisition and transmission risks. In the current era of expanding antiretroviral therapy-based prevention and treatment approaches, condom use remains a core component of mitigating these risks. A cross-sectional study characterizing the vulnerabilities for HIV among MSM in Swaziland was analyzed to describe factors associated with condom use at last sex with a male partner. Bivariate and multivariate logistic regression analyses were conducted to assess correlates of condom use at last sex with both casual and regular male partners. Disclosure of sexual practices to a healthcare provider and being able to count on other MSM to support condom use were significantly associated with condom use at last sex with a causal and a regular partner, respectively. Reporting difficulty insisting on condom use was inversely associated with condom use at last sex with both regular and casual partners. In addition, having faced legal discrimination was similarly inversely associated with condom use at last sex with a regular partner. Condom use among MSM in Swaziland may increase with improved partner communication, provider sensitization to encourage sexual disclosure, and the promotion of safer sex norms within MSM communities. These approaches, in combination with existing and emerging evidence of informed and human rights affirming prevention and HIV treatment approaches may reduce the incidence of HIV among MSM in Swaziland and all those in their sexual networks.