Background: olesteatoma is defined as the presence of collections of kertatinized squamous epithelium within a sac in temporal bone & skull base, commonly involve the middle ear cavity & mastoid cavities. Congenital cholesteatomas compose only 2% of middle ear cholesteatomas. Aim of the Work: to evaluate the role of DWMRI in detecting residual and/or recurrent cholesteatoma and to compare it to the intra-operative findings. Patients and Methods: this study was conducted on patients with recurrent or residual cholesteatoma suspected clinically or by CT examination at Ain Shams University hospitals or Hearing and Speech Institute. The patients were referred from the department of Otolaryngology, Ain Shams University hospitals, Hearing and Speech Institute and also from other private clinics. Results: from the 30 cases we examined, 19 cases (63%) showed areas of DWI restriction within the middle ear denoting primary or recurrent cholesteatoma. The smallest size of cholesteatoma detected was 4.5 mm. All 19 cases that showed evidence of recurrent cholesteatoma on MS-EPI DWI MRI images underwent second look mastoid surgery will all cases (100%) showing intra-operative evidence of cholesteatoma. Of the 11 cases that were negative for cholesteatoma on DWIs, 9 of these cases underwent second look mastoid surgery with 4 cases (44%) showing small cholesteatomas measuring less than 4 mm while the other 5 cases (56%). Conclusion: DWI is a beneficial tool in the evaluation of recurrent cholesteatoma with excellent specificity that reduces the need of second look surgeries in multiple cases.