Gestational pituitary apoplexy is an extremely rare condition. It is characterised by an unexpected headache, vomiting, nausea, and visual disturbances. Pituitary apoplexy in pregnancy and postpartum is a challenging diagnosis with symptoms overlapping multiple conditions. There is a limited number of articles presenting cases or case series of gestational pituitary apoplexy. This is a potentially life-threatening emergency which requires a high index of suspicion for its diagnosis. This article presents a case of postpartum pituitary apoplexy and outlines the current stage of clinical, imagistic diagnosis and management options. A 26-year-old primipara was submitted to a Caesarean section, with no perioperative incidents. Forty-eight hours later she reported the apparition of frontal and temporal throbbing headaches, nausea, photophobia, and she was diagnosed with a pituitary tumor measuring 33×10.5×15.5 mm. Although initially conservative treatment was proposed, the clinical outcome was not favourable, thus the patient was submitted to endoscopic transsphenoidal resection. The histopathological studies demonstrated the presence of a pituitary macroadenoma. At the 2-year follow-up, the patient is free of disease. Although it represents an extremely rare condition, gestational pituitary apoplexy should be suspected whenever headache and neurological disorders such as nausea and photophobia are reported during the postpartum period.