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Introduction and Aims—Commercial sex workers (CSW) are often portrayed as vectors of disease transmission. However, the role clients play in sexual risk taking and related decision making has not been thoroughly characterised. Design and Methods—Participants were drawn from the Vancouver Injection Drug Users Study, a longitudinal cohort. Analyses were restricted to those who reported selling sex between June 2001 and December 2005. Using multivariate generalised estimating equation, we evaluated the prevalence of and factors associated with being offered money for sex without a condom. Results—A total of 232 CSW were included in the analyses, with 73.7% reporting being offered more money for condom non-use, and 30.6% of these CSW accepting. Variables independently associated with being offered money for sex without a condom included daily speedball use [adjusted odds ratio (AOR) = 1.21, 95% confidence interval (CI): 0.23–0.62], daily crack smoking (AOR = 1.51, 95% CI: 1.04–2.19), daily heroin injection (AOR = 1.76, 95% CI: 1.27–2.43) and drug use with clients (AOR = 3.22, 95% CI: 2.37–4.37). Human immunodeficiency virus seropositivity was not significant (AOR = 0.98, 95% CI: 0.67–1.44). Discussion and Conclusions—Findings highlight the role clients play in contributing to unprotected sex through economic influence and exploitation of CSW drug use. HIV serostatus has no bearing on whether more money is offered for sex without a condom. Novel interventions should target both CSW and clients. [Johnston CL, Callon C, Li K, Wood E, Kerr T. Offer of financial incentives for unprotected sex in the context of sex work. Drug Alcohol Rev 2009]