A 35-year-old G3P2002 woman at 35-weeks gestation presented with recurrent thunderclap headaches, transient vision loss, and right hand numbness. She had a known 1.3 x 0.75 x 0.95 cm pineal cyst on imaging ten years earlier. Initial neurological evaluation revealed neck tenderness without focal deficits. Given the acuity and intensity of her headaches, MRI of her brain without gadolinium was obtained and demonstrated a 1.6 x 1.3 x 1.1 cm pineal cyst with fluid level and hemosiderin rim suggesting pineal apoplexy. MRA and MRV did not reveal any vascular dissection, tortuosity, stenosis, or occlusion. There was no hydrocephalus and no acute neurosurgical intervention was required. She was managed conservatively and discharged to follow-up with neurology and obstetrics. Given her clinical improvement and history of two prior successful vaginal deliveries despite her known pineal cyst, she was cleared to proceed with vaginal delivery at 39 weeks, which was successful.