Iliac-ureteral fistulas (IUF) are a rare but potential life threatening event and an important cause of gross hematuria. We report on three cases of IUF. In all cases, prior chronic ureteral stenting, extended pelvic surgery or pelvic irradiation had been performed. Diagnosis was confirmed with angiography in one case, in the others a CT scan revealed the IUF. Treatment included surgical exploration with local reconstruction, extra-anatomical bypass and nephrectomy with arterial patch repair. The increasing incidence of IUF is a consequence of an increasing number of advanced and extended pelvic operations, radiation therapy and long-term ureteral stenting. Diagnosis should be made by provocative angiography or CT. Treatment options vary depending on the site and morphology of the local situation, but morbidity and mortality is still high due to delayed adequate diagnosis and treatment. A conclusive algorithm should be followed for the successful management of IUF.