Radical prostatectomy remains the gold-standard surgical treatment for clinically localized prostate cancer. Contrast imaging of the upper urinary tract is not part of the routine work-up of the patient before radical prostatectomy. This may lead to rare, albeit serious complications when anatomical anomalies are present. This article reports a case of delayed anastomotic leakage following radical prostatectomy due to an unrecognized duplex system on the left side and inclusion of the ureteric orifice draining the upper moiety in the anastomosis, which caused failure of healing and persistent leakage.