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Acquired atresia of External Auditory Canal (EAC) is seldom encountered in routine otolaryngology practice. Apart from resulting in moderate-to-severe conductive hearing impairment, it is a potentially dreaded condition which might lead to canal cholesteatoma. Suspected to develop as a consequence of a pre-existing chronic otitis externa/media, the EAC atresia leads to proximal (medial) accumulation of desquamated epithelium and denatured keratin (the canal cholesteatoma) that further leads to aggravation of the chronic otitis, thereby initiating a vicious cycle. The canal cholesteatoma might progress unhindered into the middle ear and mastoid cavity, with its characteristic bone-eroding property, producing complications. A high index of clinical suspicion along with proper imaging are therefore essential to apprehend the disease progression in a patient presenting with an apparently innocuous EAC stenosis/atresia. In this report, we illustrate the clinical details of a young girl with unilateral acquired EAC atresia where canal cholesteatoma had turned extensive, invaded the middle ear cleft, and produced a post-aural fistula, thereby establishing one of the extreme outcomes of chronic otitis.