Ureteroarterial fistulas (UAFs) are defined as an abnormal communication between one of the major arteries and the ureter. Urologists most frequently encounter iatrogenic fistulas occurring in patients with a history of pelvic extirpative surgery, chronic ureteral catheterization, and history of pelvic radiation. We present two cases of UAFs in patients with no history of prior radiation, who underwent open radical cystectomy and robot-assisted radical cystectomy with intracorporeal ileal conduit. Both patients developed postoperative ureteroileal anastomotic leaks that were managed with indwelling ureteral catheters. Furthermore, both patients were having left-sided UAF after presenting with nonlife threatening gross hematuria, which became brisk and pulsatile during ureteral stent exchange. Endovascular stenting was performed in both patients with resolution of hemorrhage and full recovery. In one patient, nephrostomy tubes were placed and ureteral catheters were removed; the second patient was managed with continued ureteral catheterization without further episodes of hematuria.