Recent studies have revealed a variety of contexts involving HIV risk behaviors among women who exchange sex for money or drugs. Event analysis was used to identify the individual, relationship, and contextual factors that contribute to these high-risk sex exchange practices. Analyses were conducted on data obtained from 155 drug-using women who reported details of their most recent sex exchange event with male clients. The majority of sex exchange encounters (78%) involved consistent condom use. In multivariable analysis, protective behavior was associated primarily with situational and relationship variables, such as exchange location, substance use, sexual practices, and respondent/client discussion and control. In order to inform HIV prevention programs targeted to women sex exchangers, further research is needed on the contextual determinants of risk, especially with regard to condom-use negotiation and factors involving substance use that adversely affect women's ability to manage protective behavior in the context of sex exchange.