Cholesteatoma is a common problem encountered in otolaryngology clinics around the world. The true incidence of acquired cholesteatoma is not known but retrospective studies from Europe have suggested a mean incidence of 9.2 per 100,000.1,2 Although an important problem, the aetiology and management of cholesteatoma are shrouded in controversy. It is therefore of little surprise that there is much debate on the indications, timing or modality of imaging used in the diagnosis and monitoring of patients with cholesteatoma. It is the aim of this article to iron out some of this controversy by identifying some of the benefits of different imaging modality choices and discussing recent developments in the field. The choice of imaging strategy differs greatly between those patients who present with a new diagnosis of suspected cholesteatoma and those who have previously undergone surgery. In order to address this, the imaging strategies used for pre-operative and post-operative cholesteatoma have been presented separately.