A temporal massive hemorrhagic necrosis is an uncommon but known complication of herpes encephalitis. Cerebral vein or sinus thrombosis is a very rare complication of herpes encephalitis. Due to its rarity, this complication can go under-diagnosed, resulting at times in grave neurological deficits for the patient. The concurrent existence of both complications is even less common and difficult to diagnose. This also complicates the medical management of the patient due to contradicting considerations. We report a case of a twenty years old female, admitted with herpes encephalitis. The clinical course was complicated by a right temporal lobe massive hemorrhagic necrosis and a late sigmoid sinus vein thrombosis. Intravenous heparin, administered for the thrombosis resulted in further deterioration with evidence of increased hemorrhagic mass lesions, elevated intracranial pressure, uncal herniation and a right "blown pupil". The patient underwent a decompressive craniectomy with dural fenestrations. The patients quickly recovered, regained consciousness and was weaned off respirator. Anticoagulant therapy was reinstituted within 48 h of surgery with no further complications. We advocate a high index of suspicion (clinical and radiological) for both hemorrhagic and thrombotic complications in herpes encephalitis patients, and a judicious use of anticoagulation. A multidisciplinary team approach and an early neurosurgical consult in such patients should be the routine.