Understanding attitudes and motivations regarding safe sex is especially important for those working with incarcerated youths, as this population is considered an at-risk group for HIV infection. In order to better understand their attitudes toward safe sex, the authors and correctional staff interviewed 820 youths (691 males and 129 females) incarcerated in the Virginia juvenile justice system. Among the data obtained was information regarding attitudes toward sex and safe sex practices, age, ethnicity, length of time lived with biological mother and father, HIV/AIDS knowledge, self-esteem, hopefulness, perceived social support from family, alcohol use, and drug use. Results of statistical analyses revealed that positive safe sex attitudes were associated with being female, being African-American, having HIV/AIDS knowledge, and having high self-esteem and hopefulness. Negative attitudes regarding safe sex practices were related to alcohol use and drug use. The authors offer that the variables of HIV/AIDS knowledge, self-esteem, and hopefulness may be important factors in HIV prevention programs designed for incarcerated adolescents.