People with with criminal legal involvement are disproportionately impacted by HIV acquisition and are at high risk for poor HIV care outcomes due to care disruption posed by re-incarceration, medication non-adherence and other co-occurring conditions disproportionately represented among this group (e.g., mental illness, substance use, homelessness). Novel modalities for antiretroviral treatment (ART), such as long acting injectables (LAIs), present a promising solution to achieving viral suppression among those with adherence challenges. This study will use a unique longitudinal cohort of people living with HIV with criminal legal involvement (PWH-CLI) to understand HIV care outcomes and trajectories following release from jail, and leverage patient access through a specialty re-entry clinic for PWH-CLI released from jail to pilot test strategies to initiate PWH-CLI on LAI-ART prior to release from jail as a bridge to linkage with a community HIV care provider.