OBJECTIVE Congenital anterior urethral diverticulum is a rare entity. This teaching video shows the scrotal pop-off mechanism for an anterior urethral diverticulum and the unique voiding pattern of a boy who empties his bladder by compression of his scrotum. The findings during urethroscopy and open reconstruction are also demonstrated. METHODS A four-year-old boy presented to the clinic with a poor urinary stream and scrotal swelling during voiding. Physical examination during voiding revealed a dumbbell-shaped anterior urethral diverticulum with scrotal pop off and preserved renal function. RESULTS Open excision of the scrotal part of diverticulum was performed. Urethroplasty was conducted using a de-epithelialised diverticular wall flap from the penobulbar urethra. On follow up the boy voided with a good flow and resolution of symptoms. CONCLUSIONS Scrotal pop off with completion of voiding by manual compression of the diverticulum may preserve bladder and renal function. The preferred treatment of anterior urethral diverticulum is open excision of the diverticulum and reconstruction. The wall of the diverticulum may be used to reinforce the repair ventrally, where the corpus spongiosum is deficient.