A 61-year-old male with prior history of endoscopic urethral calculus removal presented to the emergency room with urinary retention and a palpable perineal mass. A CT showed a large calcification within the bulbar urethra. After multiple unsuccessful attempts at foley catheter insertion, the urology service was consulted. The patient was taken to the operating room where an obstructing urethral calculus with associated urethral stricture was visualized on cystoscopy. We present an exceedingly rare case of recurrent urethrolithiasis with associated urethral stricture managed with initial suprapubic tube and delayed primary end-to-end urethroplasty, excision of urethral stricture and urethral diverticulectomy.