Abstract Objectives Hepaticojejunostomy anastomotic stricture (HJAS) is a serious adverse event of pancreaticoduodenectomy. Preoperative biliary drainage with a self‐expandable metal stent (SEMS) is often performed before pancreaticoduodenectomy. The purpose of this study is to evaluate the risk factors and impact of preoperative SEMS placement on developing benign HJAS after pancreaticoduodenectomy. Methods We retrospectively analyzed consecutive patients who underwent pancreatoduodenectomy at our institution between July 2014 and June 2020. Risk factors for benign HJAS were identified using univariate and multivariate logistic regression analysis. We also compared outcomes of preoperative biliary drainage using SEMS and non‐SEMS. Results Of the 626 included patients, benign HJAS occurred in 36 patients (5.8%). The median follow‐up time was 36.7 months (interquartile range, 25.4–57.4 months). Multivariate logistic regression analysis revealed that lack of preoperative biliary drainage, preoperative bile duct diameter <5 mm, and former or current smoking were independent predictors of benign HJAS. In the preoperative biliary drainage group, the rate of preoperative bile duct diameter <5 mm was significantly lower in the SEMS group than in the non‐SEMS group (2.0% vs. 12.8%, p = 0.04). Conclusions Preoperative biliary drainage with SEMS may be useful to maintain bile duct diameter ≥5 mm and to reduce benign HJAS as a result.