Background: Given that the temporal bone is one of the most complex regions of the human body, cadaveric dissection of this anatomical area represents the first necessary step for the learning and training of the young oto-surgeon in order to perform middle ear surgery, which includes the management of inflammatory pathology, hearing rehabilitation, and also cognitive decline prevention surgery. The primary objective of this study was to identify common mistakes and critical passages during the initial steps of temporal bone dissection, specifically cortical mastoidectomy and posterior tympanotomy. Methods: A survey among 100 ENT residents was conducted, gathering insights into the most prevalent errors encountered during their training to uncover the most challenging aspects faced by novice surgeons during these procedures. Results: The most common mistakes included opening the dura of the middle cranial fossa (MCF), injury of the sigmoid sinus (SS), chorda tympani (CT), and facial nerve (FN) injury while performing the posterior tympanotomy. The most important critical steps to prevent mistakes are related to the absence of wide exposure during cortical mastoidectomy and the consequent impossibility of identifying the landmarks of the facial recess before performing posterior tympanotomy. Injury of these structures was more common in younger surgeons and in the ones who performed less than five temporal bone dissection courses. Conclusions: Numerous temporal bone dissections on cadavers are mandatory for ENT residents looking forward to performing middle ear surgery.