Demodex folliculorum and Demodex brevis are commensal human ectoparasites that reside within or near hair follicles and have been highly associated with rosacea-like papulopustular skin eruptions. We present an interesting case of recurrent, iatrogenic demodicosis in a 56-year-old man. We suspect this to have been triggered by antifungal therapy given it occurred twice closely following azole treatment. We propose that oral antifungals in the setting of immunosuppression can alter the skin microbiome, facilitating Demodex proliferation.