A 72 year old Caucasian female presented to the acute medicine unit with an episode of loss of consciousness and reports of daytime sleepiness with descriptions of an apathetic facade and somnolence from her family. Her past medical history includes mechanical aortic valve replacement and paroxysmal AF for which she was anticoagulated with warfarin, an aneurysmal subarachnoid haemorrhage complicated by hydrocephalus for which a ventriculo-peritoneal shunt had been inserted, and two previous TIAs. Examination showed a GCS of 15, bilateral superior gaze paresis, and an Epworth Sleepiness Scale score of 15/24. A non-contrast CT head showed a new well-defined hyperdensity with anterior calcification in the region of the pineal gland measuring 10 mm suggestive of a small haemorrhage into a pineal cyst. An MRI brain 2 months later showed haemosiderin staining in the pineal region in keeping with previous haemorrhage at this site. The target INR for her warfarin treatment was reduced from 3.5 to 2 as a compromise between the risk of further haemorrhage and that of valve-related thromboembolism. This is an illustration of a case of symptomatic pineal cyst and of the rare occurrence of haemorrhage into a pineal cyst in an anticoagulated patient.