OBJECTIVE: The video presents a 78 year-old G1P1 female with a history of endometriosis who presented with post-coital vaginal bleeding. She had a history of a total abdominal hysterectomy at the age of 46 due to pelvic pain, and later underwent bilateral salpingo-oophorectomy and treatment of endometriosis at the age of 56 due to continued pain. She was on hormonal supplementation with transdermal estrogen. Preoperative examination and imaging revealed a 5 cm friable mass at the vaginal cuff and a smaller pelvic mass in the left pelvic sidewall. METHODOLOGY: The patient underwent small diameter laparoscopy using a multi-puncture technique. The left pelvic sidewall mass near the left ureter was carefully resected and found to be endometriosis on final pathology. The vaginal cuff mass was also resected and determine to be endometriosis juxtaposed with well-differentiated endometrioid adenocarcinoma. CONCLUSIONS: Although not fully elucidated, there is a relationship between endometriosis and ovarian cancer. Therefore, among patients with a history of endometriosis, continued regular gynecologic follow up is recommended not only for recurrence but also for possible malignant transformation.