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Approximately 40% of all women report experiencing headaches during the postpartum period, regardless of a previous headache history. This case narrative describes the clinical case of a 22-year-old woman who presented for the evaluation of an intractable headache for 2½ weeks. It demonstrates the inherent difficulty in diagnosing patients not presenting with “textbook” symptoms and highlights the fact that signs and symptoms of eclampsia/preeclampsia, such as elevated blood pressure, may fall below the threshold for hypertensive emergencies and not be considered in the differential. Emergency department providers must possess a strong knowledge base and skill set to recognize subtle presentations and direct care accordingly to ensure positive patient outcomes.