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Adherence to antiretroviral therapy (ART) is crucial for thwarting HIV disease progression and reducing secondary HIV transmission, yet youth living with HIV (YLH) struggle with adherence. The highest rates of new HIV infections in the United States occur in young African American men. A sample of 387 HIV-positive young African American males on ART was selected from a cross-sectional assessment of (YLH) receiving medical care within the Adolescent Trials Network for HIV/AIDS Interventions (ATN) from 2010 to 2012 (12-24 years old, median 22.00, SD 2.08). Participants completed self-reported adherence, demographic, health, and psychosocial measures. Sixty-two percent self-reported 100% ART adherence. Optimal data analysis identified frequency of cannabis use during the past 3 months as the strongest independent predictor of adherence, yielding moderate effect strength sensitivity (ESS) = 27.1, p < 0.001. Among participants with infrequent cannabis use, 72% reported full adherence; in contrast, only 45% of participants who used cannabis frequently reported full adherence. Classification tree analysis (CTA) was utilized to improve classification accuracy and to identify the pathways of ART adherence and nonadherence. The CTA model evidenced a 38% improvement above chance for correctly classifying participants as ART adherent or nonadherent. Participants most likely to be adherent were those with low psychological distress and minimal alcohol use (82% were adherent). Participants least likely to be adherent were those with higher psychological distress and engaged in weekly cannabis use (69% were nonadherent). Findings suggest multiple profiles of ART adherence for young African American males living with HIV and argue for targeted psychosocial interventions.