Aim: Gynecologists, or for that matter any surgeon, are often looking forward to challenges. While challenges come in various forms, the ones encountered intraoperatively are the most challenging and satisfying as well once successfully countered. Background: Uterine leiomyomas are a routine presentation at a gynecologist's table. Depending upon the location, size, and desirability of fertility in the future, multiple therapeutic options can be offered to the patient ranging from expectant and medical management to a conservative surgical myomectomy or a more radical method, hysterectomy. Preoperative optimization of the surgical field can be done in several ways, as we did with ureteric stenting in this case. Case discussion: We report a case at our tertiary care center in a patient with multiple intrauterine fibroids, a huge broad ligament fibroid, a large endometrioma, a hematosalpinx with a history of imperforate anus and horseshoe kidney, and an intraoperative finding of the umbilical urachal sinus. Conclusion: A diagnostic challenge with a therapeutic riddle, with a multidisciplinary team approach, the patient was successfully operated on and freed of her ignominy. Clinical significance: Ureteric stenting, in this case, helped avoid inadvertent ureteric injury as was anticipated due to the broad ligament fibroid and deep endometriosis.