Histoplasmosis capsulatum is an opportunistic fungal infection that is largely asymptomatic and found to have nonspecific signs and symptoms. It predominates in Central and North America, and is one of the leading causes of hospitalization among the fungal family. However, in the right host, such as in this case, a patient with significant immunosuppression can develop serious manifestations as it disseminates outside of the pulmonary system. The challenging element of disseminated histoplasmosis is that despite proper treatment immunocompromised patients will frequently relapse with worsening presentation. There is limited literature on subacute stroke-like presentation in a patient with chronic infection of histoplasmosis, yet this patient has been repeatedly admitted over the last 10 months and found to show significant improvement upon receiving antifungal treatment. We hereby present a case about a young female patient in her late 20’s with a past medical history of congenital HIV, and hydrocephalus status post a ventriculoperitoneal (VP) shunt that presented to the emergency department with left sided weakness of the upper and lower extremities, dysarthria, and left facial droop. On brain imaging, some subacute MCA ischemia involving the right frontal, parietal, and basal ganglia and worsening cerebritis was found. The patient also underwent a lumbar puncture showing leukocytosis, and hyperproteinorrachia. Despite inconclusive findings in the CSF the patient was treated with amphotericin B intravenously and her mental status and motor deficits improved almost instantly.