Paraphimosis is a urologic emergency. It is caused by the entrapment of a retracted prepuce behind the coronal sulcus. When trapped for a prolonged time, this results in a tight constricting ring of tissue formation causing vascular compromise and swelling of the glans, which prevents the retracted prepuce into its naturally occurring anatomic position. If left untreated, can lead to glans necrosis, tissue injury or urinary outflow obstruction. A patient with paraphimosis often presents with penile pain. We present a case of urinary tract infection due to painless paraphimosis with urinary outflow obstruction. Prevention and early intervention are key elements for paraphimosis in long-term care facilities.