Objective To determine the natural history and rate of progression of incidental wide-caliber, anterior urethral strictures (USs) in men using a validated stricture staging system. Subjects and Methods Men with incidental findings of anterior US on cystoscopy performed for urologic conditions other than US were retrospectively reviewed from 2001 through 2016. Diagnosis of US on cystoscopy was made according to a validated staging system: stage 0 = no stricture; stage 1 = wide-caliber stricture; stage 2 = requires gentle dilation with a flexible cystoscope; stage 3 = impassable stricture with a visible lumen; and stage 4 = no visible lumen. Using this staging system, this study assessed the change over time of US in patients found to have a stage 1 stricture. The primary outcome was the US grade at time of follow-up. Secondary outcomes include the need for further intervention. Results Thirty-two patients with 42 separate strictures were evaluated. Median length of follow-up between first cystoscopy and ultimate cystoscopy was 23 months, with a median of 4 cystoscopies per patient. Of the 42 strictures, 15 regressed to a stage 0 (36%), 22 remained as stage 1 (52%), and 5 (12%) progressed to stage 2. None of the patients required additional intervention. Conclusion The majority of low-stage USs does not progress. This supports the notion that strictures are a graded phenomenon, and not all require surgical intervention.