Histoplasmosis is a chronic, infectious disease caused by the environmental fungus H. capsulatum, primarily affecting the respiratory system. In immunocompromised patients, histoplasmosis can become severely complicated due to dissemination into various other organ systems. Adrenal insufficiency is an uncommon complication of disseminated histoplasmosis, as its manifestation requires necrotizing granulomatous inflammation of both adrenal glands. We describe a rare case of delayed histoplasmosis in the bilateral adrenal glands and liver of an immunocompromised patient with development of symptoms at 21 years after liver transplant and nine years after renal transplant. In addition, this patient presented with secondary adrenal insufficiency due to long-term use of corticosteroids rather than the typical primary adrenal insufficiency seen in histoplasmosis with adrenal involvement.