African-American female inmates are disproportionately affected by the human immunodeficiency virus (HIV), with heterosexual contact as the primary mode of transmission. This could be the result of racial differences in the strategies used by women to persuade a potential sexual partner to discuss HIV/AIDS and engage in condom use. Data were collected from 336 female inmates as part of the Reducing Risky Relationships for HIV (RRR-HIV) protocol within the Criminal Justice Drug Abuse Treatment Studies (CJ-DATS) cooperative agreement. Bivariate analyses indicated that African-American drug-using women were more likely than Whites to use the rational, withdrawal, and persistence approaches to discuss HIV/AIDS with a sexual partner. Negative binomial regression models were used to identify which interpersonal discussion strategies were significant correlates of the number of the times White and African-American participants had unprotected vaginal sex in the 30 days before incarceration. Results from the multivariate model indicate that White women who are more likely to use the rational discussion strategy were 15% less likely to engage in unprotected vaginal sex; however, these findings were not replicated in the African-American sample. Findings add to the literature on racial differences in HIV/AIDS discussion strategies and sexual risk behaviors among drug-abusing female criminal offenders.