Anticoagulation is used to prevent and treat thromboembolic disease. While anticoagulation is an effective, adverse event from the treatment can be devastating. One of the most serious complications of anticoagulation is intracerebral hemorrhage (ICH). This chapter presents a case study of a 66-year-old male with a history of prior ischemic stroke, atrial fibrillation, hypertension, and type 2 diabetes, who developed the acute onset of right arm and leg weakness. The direct thrombin inhibitors, often used in the setting of heparin-induced thrombocytopenia, bind to thrombin leading to downstream anticoagulant effects. Risk factors for ICH in anticoagulated patients are similar to patients not receiving anticoagulation, but increasing anticoagulation intensity also contributes. Most anticoagulation agents can be reversed. Correction of the coagulopathy should occur quickly to prevent hematoma growth, a predictor of poor outcome.