Surgical treatment of cholesteatoma requires a highly individualized approach, balancing disease eradication with hearing preservation, and necessitates thorough patient counseling on expected auditory outcomes and options for rehabilitation. The choice between canal wall up and canal wall down mastoidectomy can influence hearing outcomes. Hearing rehabilitation options following cholesteatoma surgery include air- and bone-conduction devices and are individualized for the patient. Assistive listening devices such as frequency modulation systems, hearing loops, and Bluetooth technology are critical for enhancing speech understanding in noisy environments for patients who employ various hearing rehabilitation methods and require further advanced solutions.