Purpose of Review <p>This review aims to (a) synthesize available cannabis and sleep health literatures to propose a bidirectional risk model, and (b) provide a research agenda addressing priority literature gaps.</p> Recent Findings <p>Sleep problems prompt self-medication with cannabis, which inadvertently maintains or worsens sleep problems due to predictable neurobiological processes. Over time, self-medication behavior may increase to compensate for cannabis tolerance and ongoing sleep problems, ultimately increasing risk for cannabis use disorder and associated consequences. Several theoretical mechanisms may explain self-medication with cannabis for sleep aid, and underlying social determinants&#xa0;may explain sociodemographic variability and disparities.</p> Summary <p>This review proposes a bidirectional model in which cannabis use and sleep health interact in a feed-forward cycle, ultimately maintaining and exacerbating risk in both domains over time. Clinical implications are reviewed for cannabis sleep aid presenting to behavioral medicine settings. A research agenda is proposed spanning domains of epidemiology, bidirectional processes, and transdiagnostic social determinants.</p>