Herpes simplex virus (HSV) encephalitis is the most common cause of nonendemic sporadic encephalitis in the United States. Treatment with acyclovir has been proven to reduce mortality by 50%. Antiviral therapy should be initiated immediately in patients with clinical suspicion of viral encephalitis and should not be delayed by serological confirmation of the diagnosis. The most common central nervous system complication of HSV encephalitis is seizures (38%), while intracranial hemorrhage is very rare (2.7%). We describe a case of a 59-year-old African American male who presented to the hospital after being found unresponsive for a day and was found to have HSV-1 encephalitis that was complicated by hemorrhagic conversion. Our patient's neurological status did not improve even with appropriate antiviral treatment with a 28-day course of intravenous (IV) acyclovir. Intracranial hemorrhage is a rare complication in patients with HSV encephalitis. Close monitoring of neurological status is recommended for signs of deterioration or lack of improvement, and further imagings are needed (as in our patient) to evaluate for neurological complications such as intracranial hemorrhage.