The appropriate imaging of patients with headache presents a number of important and vexing challenges for clinicians. Despite a number of guidelines and studies demonstrating a lack of cost-effectiveness, clinicians continue to image patients with chronic nonfocal headaches, and the trend toward imaging is increasing. The reasons are complex and include the fear of missing a clinically significant lesion and litigation, habitual and standard of care practices, lack of tort reform, regulatory penalties and potential impact on one's professional reputation, patient pressures, and financial motivation. Regulatory and legislative reforms are needed to encourage best practices without fear of professional sanctions when following the guidelines. The value of negative findings on imaging tests requires better understanding because they appear to provide some measure of societal value. Clinical decision support tools and machine intelligence may offer additional guidance and improve quality and cost-efficient management of this challenging patient population.