Pituitary apoplexy is a rare and life-threatening clinical condition caused by hemorrhage and/or infarction of the pituitary gland or adenoma. Although pituitary apoplexy is usually spontaneous, it has been associated with numerous precipitating factors, such as bromocriptine use. However, reports of pituitary apoplexy during cabergoline therapy are scarce. We report three patients with cystic macroprolactinomas who developed pituitary apoplexy during cabergoline treatment.