Penile and scrotal entrapment from a metal ring placed at the base of the penis is a rare, but important clinical dilemma encountered in urology. Emergent presentation to the urologist, after ring placement far longer than safely practiced, risks ischemic and permanent injury to penile, scrotal, and intrascrotal structures. Treating urologists should be aware of the prevalence of metal ring use, their potential complications, and the surgical approach to their safe removal. We present two patients who were identified at our institution with strangulating injuries of retained penile rings. The first patient was a healthy, 43-year-old male with a metal ring retained for 24 hours that was safely removed with industrial bolt cutters. The second patient, a 74-year-old male, died as a result of sepsis from injuries secondary to penoscrotal ischemia after >48 hour ring retention despite prompt removal at emergent presentation. Although rare, sexual practices may include the use of penoscrotal rings. When retained, ischemic injury and edema may lead to strangulation. Emergent removal may require industrial equipment that is not within the confines of normal operating room tools. Tissue injury may be severe and sepsis life-threatening, even after ring removal.