Background Patients with therapy-resistant benign esophageal strictures (TRBES) suffer from chronic dysphagia and generally require repeated endoscopic dilations. For selected patients, esophageal self-dilation may improve patient's autonomy and reduce the number of endoscopic dilations. We evaluated the clinical course and outcomes of patients who started esophageal self-dilation at our institution. Methods This study was a retrospective case series of patients with TRBES who started esophageal self-dilation between 2012 and 2016 at the Academic Medical Center Amsterdam. To learn self-dilation using Savary-Gilliard bougie dilators, patients visited the outpatient clinic on a weekly basis where they were trained by a dedicated nurse. Endoscopic dilation was continued until patients were able to perform self-bougienage adequately. The primary outcome was the number of endoscopic dilation procedures before and after initiation of self-dilation. Secondary outcomes were technical success, final bougie size, dysphagia scores, and adverse events. Results Seventeen patients started with esophageal self-dilation mainly because of therapy-resistant post-surgical (41%) and caustic (35%) strictures. The technical success rate of learning self-bougienage was 94% (16/17). The median number of endoscopic dilation procedures dropped from 17 [interquartile range (IQR) 11-27] procedures during a median period of 9 (IQR 6-36) months to 1.5 (IQR 0-3) procedures after the start of self-dilation (p < 0.001). The median follow-up after initiation of self-dilation was 17.6 (IQR 11.5-33.3) months. The final bougie size achieved with self-bougienage had a median diameter of 14 (IQR 13-15) mm. All patients could tolerate solid foods (Ogilvie dysphagia score ≤ 1), making the clinical success rate 94% (16/17). One patient (6%) developed a single episode of hematemesis related to self-bougienage. Conclusions In this small case series, esophageal self-dilation was found to be successful 94% of patients when conducted under strict guidance. All patients performing self-bougienage achieved a stable situation where they could tolerate solid foods without the need for endoscopic dilation.