A 63-year-old male presented with a prolonged history of bilateral ear discharge, otalgia, and hearing loss. The patient required a significant number of investigations prior to obtaining a diagnosis. Subsequent investigations identified keratoacanthoma affecting the external ear canal (EAC). There has been no case report of keratoacanthoma within the EAC till now. The only risk factor identified for the development of keratoacanthoma, in this case, was the frequent use of earbuds and subsequent long-term trauma associated with a retained bud. The histology of keratoacanthoma is difficult to differentiate from that of squamous cell carcinoma but this is essential for the ear, nose, throat (ENT) multi-disciplinary team.