Displacement of the bladder outside of the pelvis by way of the inguinal canal represents an infrequent presentation of an inguinal hernia that rarely causes urinary tract obstruction. However, bladder hernias can become bothersome, painful, and potentially dangerous. We report a 56-year-old man with a chronic bladder hernia who became acutely unable to empty his bladder from its position in the right hemiscrotum after a motor vehicle accident. At hernia repair, bladder and ischemic bowel were discovered, mandating significant small bowel resection. This case presents interesting considerations and potential pitfalls when evaluating a patient with a bladder hernia.