Women represent a significant and growing segment of jail detainees and persons living with HIV. This paper examines gender differences in health status, care and social service needs, and care engagement among jail releasees with HIV. Data are from 1,270 participants in the HRSA-funded Enhancing Linkages to HIV Primary Care and Social Services multisite demonstration project (EnhanceLink). Compared to men, more women reported homelessness, reduced adherence to prescribed ART, worse health, more severe substance use disorders, and more chronic health conditions. Men and women generally reported different needs post-release. As the number of expressed needs increased, women were more likely to drop out of care. Our findings suggest that effective and gender-specific strategies are required to identify needs, link services between jails and communities, and sustain retention of women with HIV in programs after release from criminal justice settings.