Cryptococcus is a yeast typically found in bird feces such as pigeon droppings. Infection may occur through inhalation of spores or via direct inoculation into the skin. Typically there is a history of immunosuppression, but cases are also reported in immunocompetent hosts. Cryptococcus may manifest as pulmonary disease or primary cutaneous infection, but dissemination to a systemic illness is the most life-threatening concern. We present the case of a 71-year-old man with a four-year history of idiopathic lung disease, treated with oral prednisone and mycophenolate, presents with a new onset skin rash on the right wrist. He has a history of cleaning and clearing barns and sheds after a recent storm devastated the area. Birds and bats were present in these structures while he was working. Initial therapy failed, and subsequent biopsy showed the presence of Cryptococcus yeast. Further investigation yielded a positive, low titer Cryptococcus antigen screen but negative blood cultures. This case illustrates three valuable facets of patient care. Ideally, one diagnosis will explain all of the clinical presentation, but when that is not the case then multiple etiologies must be explored. Sometimes first-line therapy is ineffective, and the clinician should not be afraid to recognize that and change course. Importantly with skin lesions, failure to respond to treatment or worsening of the lesion in the face of topical and/or oral steroids should lead one to consider the possibility of infection, particularly in an immunosuppressed patient, and prompt biopsy is prudent.