<h3>Objective:</h3> N/A <h3>Background:</h3> Pituitary apoplexy is a medical emergency resulting from acute hemorrhage or infarction of the pituitary gland. Symptoms include headache, diplopia, visual impairment, and encephalopathy. We present a diagnostically challenging case of pituitary apoplexy in a patient who presented with fever, headache, diplopia, cerebrospinal fluid showing neutrophilic pleocytosis with elevated protein, and neuroimaging showing a left basal ganglia infarct with diffuse cerebral vasospasm. <h3>Design/Methods:</h3> A 46 year old post-menopausal female exhibiting a two day prodrome of severe headaches, nausea, and double vision. She presented to the emergency department febrile (104.6 F), disoriented, with a left lateral rectus palsy and mild right hemiparesis. MRI brain revealed an enhancing suprasellar lesion extending into the sphenoid sinuses and left cavernous sinus with optic chiasm effacement. Diffusion weighted imaging showed evidence of a left recurrent artery of Heubner infarct. Intracranial CT angiography revealed anterior circulation vasospasm. Cerebrospinal fluid resulted in 300 nucleated cells with neutrophilic predominance and elevated protein (121 mg/dL). Her presentation and workup was concerning for an intracranial abscess versus pituitary apoplexy. The patient underwent transsphenoidal pituitary resection, confirming a macroadenoma and pituitary apoplexy. As her CSF infectious work up and biopsy cultures remained negative, the results were suggestive of sterile inflammation and her antibiotics were discontinued. Following surgical intervention and on six month follow up, the patient remained at her baseline functional status without deficits. <h3>Results:</h3> N/A <h3>Conclusions:</h3> Pituitary macroadenomas have varying severity of presentations. Pituitary apoplexy should be considered in a patient with altered sensorium, severe headache, and cranial nerve deficits. Cerebral infarcts can result from mechanical compression from mass effect or arterial vasospasm secondary to vasoactive substances released from necrotic and hemorrhagic pituitary tumor. Prompt diagnosis and early intervention can reduce mortality and morbidity and is critical for successful patient outcomes. <b>Disclosure:</b> Dr. Sandhu has nothing to disclose. Dr. Saini has nothing to disclose. Dr. Liang has received personal compensation in the range of $500-$4,999 for serving on a Speakers Bureau for Abbvie.