Uretero-iliac artery fistulas (UIAFs) are a rare cause of gross hematuria. They form as a result of poorly vascularized uretero-iliac adhesions and the resultant fibrosis and chronic inflammatory changes. Causes include previous pelvic surgery, radiotherapy, and chronic ureteral stenting. The presentation is usually intermittent massive gross hematuria with acute anemia and hemorrhagic shock. A high index of suspicion is warranted in patients with predisposing factors for prompt diagnosis and management as it may be associated with life-threatening hemorrhage. Due to the intermittent nature of symptoms, identification is not always apparent. Open surgical repair was the treatment of choice in the past. With advancements in interventional radiology techniques, endovascular stenting of the iliac artery and concomitant ureteral stenting is the current treatment of choice. We report a case of massive gross hematuria leading to hemorrhagic shock with underlying UIAF and predisposing risk factor of pelvic irradiation. Our case report describes the diagnostic challenges with associated comorbid conditions causing delays in successful management.