Benign osteonecrosis of the external ear canal is a rare pathology that commonly gets misdiagnosed as cholesteatoma of the external ear canal, keratosis obturans and malignant otitis externa. Each pathology has characteristics that allow for differentiation between them. Careful analysis is required to diagnose properly and determine the best modality of management. This case series presents two patients that were diagnosed with benign osteonecrosis of the external ear canal and is being managed conservatively with serial debridement. Response to conservative treatment has resulted in adequate control of symptoms in both patients.