Study Purpose In the United States, approximately one million women are on probation and/or parole. A majority of women on probation and/or parole have recently resided in a controlled living environment (CLE), and a disproportionate number of women on probation and parole are living with HIV. Prior research has examined associations between recent residence in CLEs, substance use, and histories of victimization among women; however, residing in a controlled living environment and associations with HIV sexual risk behaviors have received limited attention. This study used Nyamathi’s (1989) Comprehensive Health Seeking and Coping Paradigm (CHSCP) as a guiding framework to examine associations between recent residence in a controlled living environment and HIV sexual risk behaviors among women on probation and parole. Methods This study involved secondary analysis of baseline data gathered through the NIDA-funded Women’s Health Research Study, which was conducted in an urban county in Kentucky. Study participants were recruited through flyers posted in probation offices, referrals from probation and parole officers, direct recruitment by interviewers and by mail, and local media announcements. Interviews were conducted by trained interviewers and relied on audio computer-assisted interviewing (ACASI) technology. A total of 406 women on probation or parole with histories of lifetime victimization participated in baseline interviews, which included attention to sociodemographic information, HIV risk behaviors, criminal legal system involvement, housing, mental health, victimization, substance use, social support, and other domains. STATA 17 was used to conduct all data analyses, including multiple imputation of missing data, descriptive analyses, and logistic regression analyses. Results The mean age of participants was 37.20 years old (SE=0.51). Most of the participants identified as Black/African American (42%) or White (51%). Approximately 49% of the participants recently resided in a CLE, and approximately 5% of the participants were living with HIV. Bivariate and multivariable regression analyses found no statistically significant associations between recent residence in a CLE and engagement in HIV sexual risk behaviors. However, housing instability, intimate partner violence (IPV), and marital status were associated with increased HIV sexual risk behaviors. Age, occupation, and social support were associated with decreased HIV sexual risk behaviors. When the CLE definition was expanded to include halfway house residence, there was an association with increased HIV sexual risk behavior. Implications This study found that recent residence in a CLE is not associated with increased HIV sexual risk behaviors. Additional research in this area may further explore different types of controlled living environments, including halfway houses, to understand their potential associations with HIV sexual risk behaviors, as well as to explore residents’ perspectives on and experiences with their housing and HIV risks. The findings align with prior research regarding the importance of addressing housing instability, IPV, and social support in HIV risk reduction interventions among this population of women. The study also reflects the value of Nyamathi’s CHSCP as a useful framework for conceptualizing complex phenomena associated with health experiences and identifying targets of intervention to improve health outcomes among vulnerable populations.