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While a headache can have a wide variety of clinical presentations, it may occasionally be a red flag for underlying pathology that should prompt further investigation. Here, we present a case report demonstrating headache as an uncommon symptom of deep brain stimulation (DBS) device failure and discuss its clinical significance in the rapidly expanding list of current indications of DBS treatment. A 61year-old female underwent bilateral hypothalamic DBS implantation for refractory morbid obesity. After a successful course involving significant weight loss, the patient began to experience worsening of her chronic headaches, refractory to her existing regiment. On interrogation, her generator was found to be depleted and its subsequent replacement led to a near total resolution of her headaches. This represents one of the few reported instances of headache as a sign of device failure in DBS treatment, thus adding to the wide possibility of headache presentations and their underlying pathology.