A 53-year-old male with uncontrolled diabetes mellitus who presented with progressive scrotal swelling and straining was found to have a scrotal mass highly suggestive of scrotal abscess on inguinoscrotal ultrasound. Incision and drainage of abscess revealed a mass extending from the bulbous urethra. Subsequent urethrotomy revealed a large stone enclosed in a wide based urethral diverticulum. Urethral diverticulum (UD) is a rare urologic disease entity with a prevalence rate of 0.5 to 5% for both sexes. One complication of UD includes the formation of stone calculi which only occurs in 1% to 10% of all UD cases. UD calculi masqueraded by scrotal abscess has caused diagnostic dilemma as reported cases are often misdiagnosed. Furthermore, the lack of a standard guideline for surgical management of UD in males has led to individualization of the surgical technique done in reported cases. Only 2 other similar cases have been reported in literature worldwide.