This case report describes delayed cholesteatoma detection in a six-year-old boy with recurrent ear discharge since the age of two with no history of vertigo. Removal of the cholesteatoma disclosed facial nerve dehiscence, exposure of the sigmoid sinus and the dura covering the posterior fossa, as well as two fistulas to the semicircular canals. Erosive breaches of extra- to intracranial barriers entail a risk of developing severe intracranial infections, cerebrospinal fluid leakage, irreversible deafness, and loss of vestibular function. Therefore, early diagnosis of cholesteatoma is of utmost importance.