A 43-year-old male has a medical history of Human immunodeficiency virus (HIV) with no anti-retroviral therapy for six years prior to admission. He presented from an outside hospital with 40 lbs weight loss over one year, worsening abdominal pain, and odynophagia, with CT-confirmed small bowel obstruction (SBO) in the setting of untreated cytomegalovirus (CMV) ileitis. Treatment for both the untreated HIV and CMV ileitis was started during this hospitalization, and his hospital course was complicated by disseminated histoplasmosis in his lungs and GI tract, leading to stricture and a recurrent SBO. This case report will focus on an unusual complication of untreated HIV and a late diagnosis of histoplasmosis: Histoplasma ileitis-induced stricture and recurrent SBO. To date, there are a limited number of reports that describe gastrointestinal histoplasmosis in HIV patients, and SBO remains a rare and serious complication of disseminated histoplasmosis.