A 64-year-old woman presented with a dilated right pupil and nausea that began 3 days after the onset of a mild but constant headache. She complained of an inability to focus but had no loss of vision and reported no diplopia in primary gaze. There was associated photophobia but no neck stiffness. She had completed 2 weeks of therapeutic enoxaparin for a right below-knee deep vein thrombosis (DVT), diagnosed a month prior. Anticoagulation medication was prescribed after a follow-up scan at 2 weeks showed minimal residual DVT in a branch of the medial gastrocnemius vein along with partial resolution of the thrombus in the greater saphenous vein. The patient’s medical history was remarkable for hypothyroidism, but she did not suffer from hypertension, diabetes, or cardiovascular disease. She had noticed a gradual weight gain over the preceding year, and her primary care physician began testing free urinary cortisol 2 weeks prior to presentation.