Cerebral venous thrombosis is a rarely reported complication of iatrogenic intracranial hypotension. We discuss a rare case of a 46-year-old woman presenting with a week-long history of severe orthostatic headaches two weeks following L4-L5 microscopic discectomy for symptomatic lumbar disc herniation. Computed tomography venography of the head revealed evidence of superior sagittal sinus thrombosis while contrast-enhanced magnetic resonance imaging of the brain revealed signs of intracranial hypotension consisting of pachymeningeal enhancement, bilateral subdural hygromas, enlarged pituitary gland, effacement of the basal ambient cisterns, and low-lying cerebellar tonsils. Additional lumbar spine imaging revealed the culprit to be a large epidural fluid collection extending from the epidural space to the superficial subcutaneous fat, suggestive of a cerebrospinal fluid leak. The patient was managed with admission, bed rest, isotonic intravenous fluids, caffeine, and therapeutic dosing of low molecular weight heparin. In such cases, clinical suspicion and early recognition and management are of paramount importance to prevent devastating consequences. Management, whether conservatively or with surgical intervention, should be made on a case-by-case basis.