This case involves a ten-year-old female who underwent a complicated tympanoplasty. During the procedure, the otolaryngology/audiology surgeon encountered a high jugular bulb and perforated through the vessel, which resulted in significant bleeding. During the recovery period, the patient experienced conductive hearing loss that did not improve over time. The patient underwent a re-exploration of the ear that revealed a damaged stapes and incus. An attempt was made to remove scar tissue around the site of the fracture to re-elevate and re-position the bones. The patient had to undergo an additional surgery for the placement of a prosthesis that eventually became dislodged. After the last procedure, the patient has had some improvement in her hearing but is still significantly hearing impaired.