Evaluation of cholesteatoma depends on clinical history and examination, with microscope and/or endoscope. A history of hearing loss with a chronic draining ear, refractory to ototopical medication, raises suspicion for cholesteatoma. Symptoms of Eustachian tube dysfunction or prior ear surgery including ear tubes should be elicited. Inflammation can be severe and should be suppressed if possible. Once cholesteatoma is diagnosed or strongly suspected, further workup includes audiometry prior to surgical excision. Imaging may supplement the workup and is especially helpful if there are concerning features including vertigo, third window symptoms, asymmetric bone line, facial nerve weakness, or for anticipatory guidance.