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Barebacking has been defined as condomless anal intercourse (CLAI) in the presence of HIV risk among men who have sex with men. As HIV risk contexts are evolving due to advancements in biomedical HIV treatment and prevention, we need to examine previous assumptions about risk behaviour. The present study compares correlates of risk-taking, risk reduction and pleasure and intimacy among (n = 256) self-identified barebackers (barebacker group), men who engaged in condomless sex with partners of unknown or positive serostatus (CLAI group) and men reporting neither identity nor behaviour in Canada and the U.S (non-CLAI group). Barebacker identity was associated with sexual sensation-seeking, perceived benefits of barebacking, pleasure interference with condoms, chatting about barebacking online and use of seroadaptive strategies. Participants in the CLAI group used more seroadaptive strategies yet were higher in STI vulnerability. Condomless anal sex is likely a significant aspect of self-concept in barebackers. HIV-prevention efforts that focus on enhancing efficacy of seroadaptation is more appropriate for this population rather than promoting condom use.