Abstract
Simultaneous bilateral adnexal entanglement is a rare condition with only a few cases documented in the literature. It represents an exceptional cause of symptomatic pelvic masses, posing unique diagnostic and management challenges. A 56-year-old postmenopausal woman presented to the emergency department with progressive abdominal pain. Imaging revealed bilateral adnexal masses, initially interpreted as secondary lesions to prior abdominal surgeries. Surgical exploration uncovered bilateral adnexal entanglement without evidence of ischemia. Histopathology examination confirmed mature cystic teratomas. This case highlights the complexity of diagnosing adnexal masses in postmenopausal women, especially when imaging findings overlap with benign post-surgical changes. A thorough multidisciplinary approach is essential to avoid delays and ensure accurate diagnosis.