(1) 30-year-old woman presenting at 34 weeks of pregnancy with symptoms of persisting headaches, diplopia and nausea. She presented again 4 years later with similar symptoms in a subsequent pregnancy at 35 weeks with additional complaints of blurred peripheral vision. (2) During her first pregnancy biochemistry revealed marked prolactin elevation (14,000 mIU/l). A non-contrast MRI scan of the pituitary revealed significant enlargement of the gland (22 x 14.4 x 12.5mm) beyond expected physiological limits in pregnancy and in close relation to the optic chiasm. Ophthalmology assessment showed normal visual fields, visual acuity and colour vision. She was managed conservatively with spontaneous resolution of symptoms after delivery. A 3 month post-partum contrast MRI showed her pituitary gland had returned to normal. Prolactin levels normalised (156 mIU/l) at 17 months post-partum, after breast feeding had ceased. During her second pregnancy prolactin levels were once again markedly elevated (34,692 mIU/L and 24,855 mIU/L on repeat). A non-contrast MRI scan revealed a 22 x 14.5 x 12mm well defined isointense pituitary lesion reported as a macroadenoma, with mild mass effect on the optic chiasm. Ophthalmology assessment showed an unremarkable OCT with a slightly constricted right-sided Goldmann visual field. (3) Per MDT discussion she commenced Cabergoline therapy (only taken for 1 week). Symptoms once again resolved soon after delivery. A contrast MRI scan at 4 months post-partum showed her pituitary gland had returned to normal again without an identifiable focal lesion. 6 months post-partum her visual field assessment was unremarkable; additionally further prolactin levels were normal (breast feeding ceased at 3 months post-partum). On endocrine clinic review at this time she remained stable and asymptomatic. On further questioning she had regular menstrual periods between pregnancies (both of which were spontaneous) and there was no history of galactorrhoea when not breast feeding. No further children were desired, but a recommendation was made for visual field monitoring during any potential future pregnancy. (4) Pituitary hyperplasia is a common entity in pregnancy. Exaggerated symptomatic hyperplasia in pregnancy is a rare occurrence and recurrent episodes in the same individual even more so. Assessment requires review of clinical, hormonal and radiological findings. Surgical intervention is unlikely to be indicated in such cohorts due to its transient nature across the peripartum period. Medical therapy with dopamine agonists should be considered especially when associated with accelerated biochemical hyperprolactinaemia, and visual field monitoring is advisable in future pregnancies.