Background <p>Pineal cyst is an uncommon condition in pregnancy. It is often encountered as an incidental finding. Most pineal cysts are benign and asymptomatic. Bleeding inside these cysts is rarely encountered in pregnancy.</p> Clinical presentation <p>A 30-year-old female patient with no significant past medical history, presented to the emergency department at 36 weeks gestation with a transient episode of unilateral headache. Headache was associated with dizziness and left arm ascending numbness. She has a history of a known pineal cyst. The neurological examination was normal.</p> Investigations <p>CT head was obtained, reviewed and compared to previous scans 7 years ago. It showed a hemorrhage inside the pineal cyst .</p> Management <p>The patient was admitted to the neurosurgery department for conservative management and a few days later, symptoms gradually improved.</p> Follow-up <p>Three weeks later, the patient reported spontaneous improvement of the presenting symptoms. The decision was to proceed with continued watchful follow-up and awaiting a caesarian delivery. The patient returned for a follow-up three months later without any symptoms. Following delivery, the patient remained asymptomatic.</p> Conclusion <p>Pineal cyst apoplexy is a relatively rare condition and it usually affects young females, however, the exact relation to pregnancy and the effect of apoplexy on the course of pregnancy are not well defined.</p>