Phaeohyphomycosis is an infection caused by dematiaceous fungi, which are ubiquitous throughout the world. We present the case of a 41-year-old immunocompromised man with Cushing syndrome who developed a phaeohyphomycotic infection. The patient presented with painful, progressive nodules that were biopsied and cultured to reveal dematiaceous fungi. Treatment of this condition is particularly difficult as demonstrated by this patient’s intolerance to itraconazole and amphotericin B. Because of the increasing number of immunocompromised patients and incidence of phaeohyphomycosis, a heightened level of suspicion is necessary on the part of the clinician for both diagnosis and treatment of this disease.