A 47-year-old woman with a recent clinical diagnosis of acute cholecystitis developed acute adrenal failure. Initial computed tomograms of the abdomen showed bilateral adrenal swelling which evolved into bilateral adrenal hemorrhage on repeat examination a few days later. Laboratory investigations revealed a previously undiagnosed primary antiphospholipid syndrome and homozygosity for the MTHFR C677T mutation with hyperhomocysteinemia. This case highlights the protean clinical manifestations of adrenal vascular accidents and the need for a thorough search for underlying prothrombotic states in this setting.