Diabetic mastopathy is an uncommon immunologic breast disease occurring usually in patients under long-term insulin treatment. It can pose a question of differential diagnosis with breast cancer especially in case of family history of breast cancer. We report the radiological diagnostic approach of a case of diabetic mastopathy with family history of breast cancer. The mammogram was nonspecific. Ultrasound showed two suspicious masses of right breast without suspicious enhancement on MRI. Diabetic mastopathy was confirmed on histology without cancer cells. Diabetic mastopathy is a diagnostic challenge and needs to be suspected in all patients with type I diabetes. Image-guided biopsy confirmation remains mandatory. The literature is briefly reviewed.