The diagnosis of a primary headache disorder requires applying symptom profiles to existing diagnostic criteria and ruling out organic disease that can mimic the primary headache disorders. Many physicians encounter patients whose headaches appear consistent with a primary condition but whose response to treatment is insufficient or absent altogether. This chapter provides a strategic approach to the patient with intractable headaches, emphasizing the possible reasons for intractability and ways to address these variables. The most important factors to consider include medication overuse headache (formerly rebound), the presence of an incorrect diagnosis, improper medication selection or dosing, psychological barriers, the need for a more intense and aggressive treatment environment (hospitalization), use of opioids, and the need for interventional therapy. Each of these variables will be considered in detail with recommendations and approach strategies provided.