<p>Headache is a common and potentially critical symptom in emergency settings, particularly among middle-aged patients, where it may indicate underlying pathologies. While neurologists must remain vigilant for alarming symptoms commonly referred to as “red flags” to prevent life-threatening conditions, other less familiar causes of secondary headache may fall outside their immediate expertise, such as skull base osteomyelitis, a condition more relevant to other specialties. We present the case of a middle-aged diabetic patient who was admitted to our emergency department several days after a prolonged hospitalization for a secondary headache initially attributed to giant cell arteritis. The patient had been treated with corticosteroids for an extended period but experienced progressive clinical deterioration despite this intervention. A reevaluation of the patient’s medical history revealed a previously overlooked ear-nose-throat (ENT) procedure preceding the onset of symptoms. This finding prompted suspicion of atypical skull base osteomyelitis as the underlying cause, which was subsequently confirmed through radiological imaging and nasopharyngeal biopsy. Although time constraints in emergency settings often limit detailed patient evaluations, a comprehensive review of the medical history is essential. Such an approach can uncover critical information that guides clinical suspicion, supports diagnostic processes, and improves patient outcomes.</p>