Until this 24 -year -old male was sexually active, the small dimple on his penile glans had never required any consideration. However, persistent focal irritation during sexual intercourse compelled him to pursue medical attention. Following urological consultation he was referred for imaging evaluation that demonstrated urethral duplication. After determining the subtype classification, urologic repair was successfully completed without complication. Urethral duplication is an exceedingly rare genitourinary anatomic anomaly with a variety of presentations and symptomatology. The vast majority of urethral duplications are diagnosed within the paediatric and adolescent populations. Although urethral duplication is managed by urologists, imaging identification of the particular subtype is critical for proper management planning. A thorough review of existing literature on the classification strategies and diagnostic criteria is discussed. Owing to the scarcity of clinical experience, a wide variety of diagnostic approaches are described. These often include unnecessary radiation, invasiveness and cost. A strategic and efficient diagnostic algorithm is included to guide future imaging evaluation of suspected urethral duplication. This provides the essential clinical information, while minimis ing radiation, invasiveness and cost.