Recidivistic cholesteatoma encompasses residual as well as recurrent disease, and can occur in up to 61% of cases. Pediatric disease may have a higher propensity for recidivism. Serial physical examination and MRI including non-EPI DWI sequences are useful in surveillance. Canal wall down approaches with mastoid obliteration may be an approach to reduce recidivism while minimizing the need for mastoid cavity maintenance. Modern techniques of Eustachian tube dilation and endoscopic ear surgery may yet prove particularly helpful in reducing re-retraction and residual disease in the retrotympanum, respectively; however, they require further study.