The transformation of benign endometriosis into endometriosis-associated cancers is rare. The physiopathology of this phenomenon is still complex and remains controversial, but atypical endometriosis has been described as a precursor to endometriosis-associated ovarian cancer, especially in endometrioid and clear-cell ovarian carcinomas. This chapter explores the pivotal role of imaging in the diagnosis of atypical endometriosis and endometriosis-associated cancers. Radiologic techniques, such as ultrasound (US), computed tomography (CT), and magnetic resonance imaging (MRI), play a crucial role in the early detection, characterization, and monitoring of atypical endometriosis and endometriosis-associated ovarian and extra-ovarian cancers. The chapter also highlights the challenges in accurately diagnosing atypical endometriosis and emphasizes the significance of imaging modalities in distinguishing benign from potentially malignant tumors. A comprehensive understanding of the imaging features associated with atypical endometriosis and endometriosis-associated cancer is fundamental as it aids clinicians in making informed decisions regarding treatment strategies, contributing to improved patient outcomes.