This chapter focuses on vaginal surgeries with adnexal pathology. The most gynecological surgeries are hysterectomy, ovarian cystectomy, myomectomy, and pelvic endometriosis. With the advent of laparoscopy and safer anesthesia protocols, abdominal route for gynecological pathology has been gradually decreasing. When uterine pathology is associated with any adnexal pathology like ovarian cyst, hydrosalpinx, paraovarian cyst, broad ligament fibroid, the gynecologist review their decision of vaginal approach for surgery. Technique for vaginal surgery for adnexal masses and transvaginal extraction through posterior colpotomy are covered in this chapter. During the past two decades, laparoscopy has become the most common route of gynecological surgeries especially hysterectomy and ovarian cystectomy. The well-known advantages of laparoscopic procedures are smaller abdominal scars, better exposure of pelvic anatomy and lesser postoperative pain and intra-abdominal adhesions and shorter postoperative hospital stay. But, one of the most important disadvantages or downside of endoscopic surgery is the retrieval of surgical specimens like large myomas, dermoid ovarian cyst, and solid ovarian tumors intact from the small ports.