We report the case of a 34-year-old female with right-sided cholesteatoma and progressive left-sided conductive hearing loss. A cephalocele contacting the left incudomalleolar joint was suspected preoperatively and treated, but a facial nerve prolapse contacting the stapes was also discovered intraoperatively. This case emphasizes the importance of thorough and systematic evaluation to avoid satisfaction of search and anchoring bias, and illustrates the need for collaborative review of imaging findings among clinicians and radiologists to mitigate cognitive biases and improve diagnostic accuracy. Laryngoscope, 2025.