We present the case of a 58-year-old diabetic renal transplant patient who developed a left jugular foramen syndrome, secondary to an ipsilateral staphylococcal malignant (necrotizing) otitis externa. This followed a protracted episode of uncomplicated otitis externa with no evidence of bone involvement on computed tomography (CT) scanning. Cyclosporin-induced hypertrichosis (excess hair growth) in his external auditory canal contributed greatly to the initial difficulty in managing his otitis externa. Following an initial successful treatment with prolonged intravenous antibiotics the patient relapsed with a secondary infection in the same anatomical site due to Candida parapsilosis. Despite further intensive treatment including antimicrobials, a subtotal petrosectomy and hyperbaric oxygen therapy he eventually succumbed to his disease.