Pituitary apoplexy (PA) occurs in the setting of an infarction and/or hemorrhage of a pre-existing adenoma. The most common presenting symptom is a severe, sudden onset headache. However, the characteristics of headache in the setting of PA are varied and can sometimes mimic primary headache disorders. The purpose of this article is to review the various presentations of headache in PA. We also outline treatment options for persistent headaches following PA.A recent retrospective review of patients undergoing transsphenoidal resection of sellar lesions, including PA, found that gross total resection and short duration of preoperative headache were predictors of improvement in headaches postoperatively. This strengthens the importance of timely recognition of PA as potential etiology of headache. The most common presentation of PA is thunderclap headache; however, several other primary HA disorders have been described including status migraine, SUNCT, and paroxysmal hemicrania.