A 23-year-old woman was referred with light periods and subfertility with a raised prolactin (1175 miu/l). Remaining pituitary function tests were normal. As she was now pregnant, investigations were postponed until post-pregnancy. Post-partum prolactin was 1823 miu/l and MRI pituitary demonstrated a 13.5 mm pituitary macroadenoma. Cabergoline was commenced but stopped due to a further pregnancy. At 22 weeks gestation she experienced left visual field loss. MRI showed subacute haemorrhage within the pituitary. Prolactin 1673 miu/l, cortisol 354 nmol/l, thyroid function normal. The remainder of the pregnancy was uneventful. MRI post-partum showed reduced size of the pituitary lesion. There was no indication for surgery and she was restarted on cabergoline. During her third pregnancy an MRI scan was arranged due to constriction of the visual fields showing new haemorrhage. Prolactin was 2351 miu/l. Remaining pituitary function tests were normal. She was commenced on hydrocortisone. The remainder of her pregnancy was uneventful. Five days post-partum she presented with severe headache. MRI showed no evidence of fresh haemorrhage and a reduction in size of the pituitary lesion. She restarted cabergoline with good response; prolactin 25 miu/l with significant reduction in lesion size (4.5 mm). Her prolactin rose to 2055 miu/l when cabergoline was discontinued and it was restarted. During a further pregnancy she presented with severe headaches at 27 weeks. MRI showed a significantly enlarged pituitary gland with evidence of an acute haemorrhage into the gland. There was no derangement in pituitary function. She successfully completed her pregnancy and continues on oral hydrocortisone. Pituitary apoplexy is a rare but potentially life threatening condition. There is increased risk in pregnancy due to the physiological enlargement of the pituitary gland. To our knowledge this is the first documented case of recurrent pregnancy induced pituitary apoplexy. This case raises questions over the optimum management of pregnancy induced apoplexy.