Abstract Objective To describe the experience and long-term follow-up after Roux-en-Y hepaticojejunostomy and define potential risk factors for early and late postoperative outcomes, such as bile leakage and anastomotic stricture. Summary Background data Roux-en-Y hepaticojejunostomy is widely used in gastrointestinal surgery. Bile leakage and anastomotic stricture are of the most relevant postoperative complications. The risk factors for postoperative morbidity are poorly described. Methods All patients who underwent hepaticojejunostomy between January 2014 and December 2020 were included in this study. Follow-up was performed for four years. Exact logistic regression was performed, associations between clinical and operative variables were explored. Bile leakage and anastomotic stricture were defined as outcomes at early and late follow-up respectively. Results A total of 199 patients were included in this study. Female patients were 56.28%. Mean age 61.73yo. The mean follow-up period was 54 months. Pancreatic cancer was the most common preoperative diagnosis (52.26%). Bile leakage was observed in 4.02%, and anastomotic stricture in 4.52% after 4 years of follow-up. A body mass index (BMI) of 27 kg/m2 or higher was associated with bile leakage (p = 0.002 95% CI 1.9-13.85), A benign diagnosis was associated with an anastomotic stricture. (p = 0.001, 95% CI 2.2-21.4). Conclusion The appropriate technique is the key factor in decreasing both biliary leak and anastomotic stricture after surgery. It seems that a BMI greater than or equal to 27 kg/m2 is associated with an increased risk of postoperative bile leakage. Oncologic conditions increase postoperative morbidity but do not affect biliary leaks or stricture. In addition, benign conditions are associated with a high risk of anastomotic stricture.