Although non-malignant,middle ear cholesteatoma can result in significant complications due to local bone erosion and infection. The treatment of cholesteatoma is surgical, but residual disease is common and may be clinically occult, particularly when the canal wall is preserved or reconstructive techniques are employed. Imaging plays a pivotal role in the management of patients with middle ear cholesteatoma-aiding clinical diagnosis, identifying complications, planning surgery, and detecting residual disease at follow-up. Computed tomography is the primary imaging tool in the preoperative setting since it canprovide botha surgical roadmap and detect erosive complications of cholesteatoma. The ability of magnetic resonance imaging with non-echoplanar diffusion-weighted sequences to accurately detect residual disease has led to a shift in the diagnostic paradigm for post-surgical follow-up of cholesteatoma, such that routine "second-look" surgery is no longer required. The following practice recommendations are aimed athelping the radiologist choose appropriate imaging approaches and understand the key diagnostic considerations for the evaluation of pre- and post-surgical middle ear cholesteatoma. KEY POINTS: In the preoperative setting, CT is the first-line imaging modality and MRI is reserved for rare clinical scenarios (low evidence). Non-echoplanar imaging (EPI) DWI is the optimal MRI sequence for the detection of residual cholesteatoma (moderate evidence). Non-EPI DWI plays an important role in the postoperative surveillance of cholesteatoma (moderate evidence).