An 18-year old man presented with left loin pain and recurrent urinary tract infections. Ultrasound and IVU revealed a duplex left kidney with hydronephrosis of the upper polemoiety. F-15 Mag-3 renography confirmed obstruction of the upper pole moiety. Cysto-urethroscopy identified the site of ectopic insertion to be adjacent to the verumontanum in the prostatic fossa. Retrograde ureterography showed the level of obstruction and dilation of the stricture was carried out. Post operatively, the patient became asymptomatic and remains so at 5-year follow up. This is an unusual case of obstructive upper pole ureter with an ectopic insertion into the prostatic fossa. We a lso demonstrated that dilatation of a stricture at this site can achieve good long term outcome. © 2004 Kluwer Academic Publishers.