The new appendix criteria for a broader concept of chronic migraine from the International Headache Society no longer require headache resolution or return to the previous headache pattern to confirm the diagnosis of medication overuse headache (MOH). MOH can be subdivided into simple (Type I) and complex (Type II). Complex cases may involve long-term use of daily opioids or combination analgesics, multisourcing, multiple psychiatric comorbidities, and/or a history of relapse. Daily use of opioids for other medical conditions, psychiatric comorbidity including borderline personality disorder, prior history of other substance dependence or abuse, and family history of substance disorders are risk factors for MOH. Relapse for analgesic overusers can be as high as 71% at 4-year follow-up. A case illustration spans 20 years from initial presentation through multiple periods of recovery and relapse to illustrate issues in the screening and management of complex MOH patients.