Primary external auditory canal wall cholesteatomas are usually present in the inferior portion of the canal lateral to the tympanic membrane. Small inclusion cysts are a common finding along incision lines after ear surgery. This report details 5 cases of large canal wall cholesteatomas after prior ear surgery. The middle ear or mastoid was not directly involved in any of the cases. The largest of these presented 8 years after the initial procedure and eroded in the middle and temporal fossae. A common feature among these patients was an extended period in which the patient was lost to follow-up after surgery. This experience reinforces the need for vigilant long term follow up even in the asymptomatic postoperative patient.