Headache is a common symptom in patients with sellar and parasellar lesions. However, when it is sudden, severe, and accompanied by visual or neurological disturbances, it may indicate pituitary apoplexy—a rare, life-threatening syndrome caused by infarction and/or hemorrhage of the pituitary gland. This chapter presents the case of a 37-year-old male who experienced an abrupt, intense headache, followed by vomiting and decreased visual acuity. Imaging revealed a previously undiagnosed pituitary macroadenoma with signs of hemorrhagic expansion and suprasellar extension. He underwent urgent microsurgical transsphenoidal surgery with endoscopic assistance, with significant postoperative improvement in both headache and visual symptoms. Histopathological analysis confirmed a non-functioning adenoma with mild prolactin elevation due to stalk compression. The discussion explores clinical presentation, pathophysiology, and differential diagnosis of pituitary apoplexy, emphasizing the importance of early recognition and prompt management. The headache in pituitary apoplexy often arises from sudden sellar expansion and meningeal irritation. Surgical decompression remains paramount for patients with visual deficits or deteriorating neurological status. The case exemplifies the need for multidisciplinary coordination to ensure favorable outcomes and highlights the essential role of headache as an early warning sign of pituitary apoplexy.