Purpose of review <p>Sleep and headache disorders share a complex, bidirectional relationship. This review summarizes current evidence on various aspects of sleep and three primary headache disorders—migraine, tension-type headache, and cluster headache. We also suggest inclusion of a clinical questionnaire and treatment pearls for clinicians treating patients presenting with headache and sleep complaints.</p> Recent findings <p>Several sleep disorders, particularly insomnia and restless legs syndrome, are highly prevalent in patients with migraine. Insomnia may contribute to or be a manifestation of a more severe migraine phenotype. Poor sleep is associated with worse pain severity for chronic tension type headache. Circadian studies in cluster headache further confirm hypothalamic and possibly, the trigeminal ganglion control. Behavioral interventions and pharmacologic considerations may optimize sleep and headache outcomes.</p> Summary <p>Sleep symptoms and headache frequently co-occur, with emerging evidence identifying underlying networks and drivers. Individualized sleep assessments and interventions are an important part of comprehensive headache treatment for many patients.</p>