Cryptococcosis is a fungal infection that typically affects immunocompromised patients. It most commonly affects the lungs and may then disseminate to the central nervous system, bone, skin, and adrenal glands. Herein, we describe a 69-year-old man who presented with skin lesions as the initial manifestation of disseminated cryptococcosis. Initial workup led to an assumption that the patient was immunocompetent. Later in the clinical course, idiopathic depletion of CD4 T cells was discovered. This case highlights that disseminated cryptococcosis may present with cutaneous symptoms even when there is no evidence of pulmonary or central nervous system involvement and may be the first sign of an underlying cellular immune dysfunction.