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Objectives: In a retrospective analysis of a quaternary referral neuro-otologic private practice, we identify complex cases of petrous bone cholesteatoma (ie, cases with encasement of vital structures such as the internal carotid artery, jugular bulb, and sigmoid sinus, with further extension to the clivus, sphenoid sinus, or rhinopharynx), review surgical approaches and techniques of management of vital structures, and propose the ideal surgical management. Methods: We performed a retrospective case study of 130 cases of petrous bone cholesteatoma submitted to surgery between 1979 and 2009 to identify the complex cases and their classification, approach used, outcomes, and recurrences. Results: Of 130 cases. 13 were complex. Facial palsy was the presenting feature in 11 cases, 7 of which presented with grade VI palsy. A long duration of facial palsy (more than 3 years) was seen in 5 cases. Clival involvement was seen in 6 cases; 1 case extended to the sphenoid sinus, and 1 to the rhinopharynx. The internal carotid artery was encased in 11 cases in the vertical and the horizontal parts. The jugular bulb was involved in 7 cases. Modified transcochlear approaches or infratemporal fossa approaches were used in all cases. There were no recurrences. Conclusions: Classification is fundamental to choosing the right surgical approach. Transotic and modified transcochlear approaches hold the key to treating complex cases. Infratemporal fossa approach type B has to be used for extension into the clivus, sphenoid sinus, or rhinopharynx. Internal carotid artery, jugular bulb, and sigmoid sinus involvement should be identified before operation. [ABSTRACT FROM AUTHOR]