Urethral strictures arise from various causes and can result in a range of manifestations, from an asymptomatic presentation to severe discomfort secondary to urinary retention. Establishing effective drainage of the urinary bladder can be challenging, and a thorough understanding of urethral anatomy and urologic technology is essential. Consultation with a urologist should be obtained for any patient presenting to the emergency department with urinary retention secondary to urethral stricture disease.