Leiomyoma of the uterus, also called fibroids, are common in women. In this case report, we describe the case of a nulliparous woman with a large, prolapsed submucous uterine leiomyoma of 10 × 11 cm was vaginally impacted. The aim is to highlight the challenges in managing such uncommon clinical scenario focusing on the factors predicting the success of vaginal myomectomy including the size of the myoma but also the role of vaginal laxity to allow the steps of devascularization, detachment, and removal of the myoma. We also describe the preoperative and intraoperative methods that can be used to minimize intraoperative blood loss and enhance the safety and feasibility of the surgical procedure. Gonadotropin therapy was not applicable in our patient, and other treatments were also unavailable such as temporary ligation of uterine arteries, while others were unsuccessful like devascularization by hysteroscopy, twisting, and ligation of the pedicle. The final resort used in our case was morcellation of the myoma with intact pedicle, which should be attempted by experienced gynecologic surgeons only.