Background <p>Tympanic membrane retraction pockets (TMRP) are supposed to happen because of Eustachian tube dysfunction (ETD), leading to progressive tympanic membrane (TM) retraction. Left untreated, these may progress to cholesteatoma with ossicular erosion and hearing loss.</p> Aim <p>To evaluate conventional microscopic against transcanal endoscopic intervention in the surgical management of TMRP as a preventive strategy for developing cholesteatoma with restoration of normal hearing.</p> Patients and methods <p>This was a prospective analytic comparative study performed on the 60 patients admitted to the Otorhinolaryngology Department, Mansoura University Main Hospital. The individuals were separated: localized retractions of the pars tensa, generalized retractions of the pars tensa (atelectasis), and retraction of the pars flaccida (around 20 persons for each subgroup who have additionally been separated into 2 groups: group I (number = 30): treated transcanal endoscopically, group II (<i>n</i> = 30): treated microscopically.</p> Results <p>Pain following the predation has significantly been reduced in the endoscopic group across all subtypes (<i>p</i> &lt; 0.05). Patient satisfaction was higher with endoscopic surgery, particularly in localized pars tensa retractions, where 70% rated their outcome as excellent versus 10% in the microscopic group. Recurrence and cholesteatoma incidence were significantly reduced in pars flaccida retractions treated endoscopically (0% vs 40%, <i>p</i> &lt; 0.05). Hearing improvement was achieved in over 90% of both groups with no significant difference. No major complications such as facial nerve injury were reported.</p> Conclusion <p>The endoscopic-assisted method may facilitate less invasive surgery and enhance postoperative results than the conventional method.</p>