Anticoagulant-related adrenal hemorrhage, as a cause of adrenal insufficiency, is rarely suspected and diagnosed during life. We report three patients in whom prompt diagnosis allowed successful treatment with replacement doses of corticosteroids. In all three patients, a hypotensive episode preceded the signs and symptoms of acute adrenal insufficiency. The symptoms and signs of adrenal hemorrhage were nonspecific and variable, making clinical diagnosis difficult. In none of our patients was the prothrombin time, partial thromboplastin time, or Lee White clotting time prolonged beyond the therapeutic range, and in none were excessive doses of anticoagulant therapy employed. Characteristic serum chemistry abnormalities, serum ACTH stimulation tests, and daily urinary collections for free cortisol, 17-OH ketosteroids, and 17-ketosteroids confirmed the clinical suspicion of primary adrenal insufficiency in all cases. Diagnosis was aided in one patient by abdominal computerized axial tomographic scan. In all patients, response to replacement doses of corticosteroids was prompt and gratifying, underlining the importance of suspecting this complication of anticoagulant therapy and instituting prompt lifesaving therapy. Adrenal hemorrhage is a complication of anticoagulant therapy that has been diagnosed during life in only 11 reported cases. We describe three patients in whom early diagnosis allowed prompt medical therapy and favorable outcome. The clinical presentation, diagnostic laboratory features, and therapeutic modalities are reviewed. Prolongation of prothrombin time, high levels of stress, and hypotension predispose to this complication in a patient maintained on anticoagulant therapy.