Anastomotic stricture (AS) is a common late complication after esophagectomy. Evidence guiding endoscopic escalation (“step-up”) and the risk of post-treatment recurrence remains limited. We assessed clinical, surgical, and procedural determinants of (i) need for step-up therapy and (ii) recurrence after initial endoscopic success.

We conducted a ten-year multicenter retrospective study at two Milan tertiary centers (2014–2024). Adults with naïve post-esophagectomy AS underwent standardized endoscopic management (bougie or pneumatic dilatation with predefined step-up options: incision therapy, stenting, steroid injection). Outcomes included technical (TS) and clinical success (CS), safety, rate of step-up and recurrence, and uni/multivariable predictors for change of strategy and recurrence.

Among 1,729 esophagectomies, 61 patients (3.5%) developed benign AS. Initial therapy was bougie in 54.1% and pneumatic in 45.9%. TS was reached in 100% and CS in 93.4%. Safety was favourable (1/61, 1.6%). Overall, 39.3% required a change of strategy, typically early: the first switch occurred at a median of 35 days, and 62.5% within 30 days, most often for failure to achieve a ≥2-mm lumen gain (66.7%). On multivariable analysis, higher BMI (OR 0.81 per 1 kg/m², p = 0.022) and baseline dysphagia <2 (OR 0.13, p = 0.006) independently reduced the likelihood of step-up. Among patients with CS, recurrence occurred in 24.6% (14/57). In models restricted to surgical variables, stapled versus hand-sewn anastomosis was protective (OR 0.11, p = 0.022), whereas procedure type (McKeown vs Ivor-Lewis) and calibre ≤25 mm were not significant.

Endoscopic treatment of post-esophagectomy AS is highly feasible and effective. Early escalation clusters within the first month and is more likely in patients with lower BMI and greater dysphagia, supporting closer early surveillance. After initial success, stapled anastomosis appears to mitigate recurrence risk.