Incarcerated individuals in the United States are reportedly four times more likely to be infected with HIV than members of the general population, and a substantial proportion have a history of drug use. Postincarceration, many struggle to maintain their antiretroviral therapy (ART) regimen. This pilot study tested the potential performance of two ART adherence interventions, Project ADHerence Education and Risk Evaluation (ADHERE) and Medication Adherence and Care Engagement (MACE) among drug-using HIV-infected formerly incarcerated individuals in New York City. Thirty participants were randomized and completed the ADHERE or MACE intervention. Participants were interviewed and had their blood drawn for viral load testing at baseline and 3 months postintervention. Our findings suggest that drug-using HIV-infected formerly incarcerated individuals can benefit from brief ART adherence interventions. They also suggest that marijuana use may not have a negative impact on ART adherence.