Accurate imaging of urethral strictures is critical for preoperative staging and planning of reconstruction. The current gold standard, retrograde urethrography (RUG), allows for accurate diagnosis, staging, and delineation of urethral strictures, and remains a cornerstone in the management of urethral stricture disease. In complex situations, the RUG can be combined with voiding cystourethrogram (VCUG) in order to better visualize the posterior urethra or complex distraction defects. Direct visualization of the stricture by cystoscopy, either retrograde or antegrade, can provide additional information as to the location and appearance of stricture, as well as precise location on fluoroscopic imaging. Sonourethrography (SU) is a useful adjunct to allow for three-dimensional assessment of stricture length and location, and can be a useful intraoperative assessment tool, however, its use remains limited to a second-line setting. Cross-sectional imaging in the form of computed tomography (CT) or magnetic resonance urethrography can provide additional three-dimensional information of anatomic structures and their relations, and can serve as a useful adjunct in complex clinical scenarios.