Urethro-ejaculatory duct reflux (UEDR) is an uncommonly discussed entity that may result in devastating complications. We discuss the case of a young married male with obstructive voiding symptoms along with intermittent left scrotal pain for last the 2 years. On voiding cystourethrography, he had intravasation of contrast into the prostatic ducts, vas deferens and epididymal ducts suggestive of UEDR which might be the cause of his scrotal pain due to recurrent episodes of epididymitis. Complete resolution of voiding symptoms and recurrent scrotal pain occurred after management of urethral stricture. The possibility of UEDR should be kept in mind while dealing with men suffering from recurrent prostatitis, seminal vesiculitis, epididymitis or, less commonly, infertility.