Despite campaigns to increase safer sex practices, there are people living with HIV/AIDS (PLWH) who do not disclose their HIV status to sexual partners and engage in condomless sex. The purpose of this research was to: 1) describe factors associated with disclosure of HIV status to sexual partners; and 2) determine if disclosure and/or receipt of prevention counseling are independently associated with condomless sex. We used the Florida Medical Monitoring Project to analyze data from 376 HIV positive men with more than one sexual partner. Results indicated that 55% consistently disclosed their HIV status to sexual partners, 30% inconsistently disclosed, 15% did not disclose, and 48% reported any condomless sex. The odds of having condomless sex was 3.3 (CI = 1.5, 7.3) times greater in men who disclosed to all partners. Results suggest that men who disclose are also those who are more likely to have condomless sex. More research is needed to better understand the complex nature of disclosure and sexual risk behaviors and how disclosure impacts sexual risk.