Background Operations requiring biliary-enteric anastomosis are uncommon, and the true incidence of postoperative stricture is unknown. Our goal was to determine the timing, incidence, and management of stricture after biliary-enteric anastomosis. Methods We used 5% Medicare claims data (1996–2011) to identify patients ≥66 years who underwent an operation requiring a biliary-enteric anastomosis. A cumulative incidence curve was used to describe timing of stricture diagnosis. The use of imaging and intervention was evaluated. A Cox proportional hazards model was constructed to identify factors associated with stricture. Results A total of 3,374 patients underwent an operation requiring either a hepaticojejunostomy (54.33%; N = 1,833) or choledochojejunostomy (45.67%; N = 1,541); 2-year survival was 57.0%. Overall, 403 (11.9%) patients developed a stricture. The cumulative incidence of stricture was 12.5% at 2 years. Mean time to stricture diagnosis was 16.8 ± 21.6 months (median = 8.5 months); 23% of patients with a stricture required hospitalization for cholangitis (N = 94). Only 18 (4.5%) patients with a stricture required reoperation. Younger age (hazard ratio 0.98; 95% confidence interval 0.98–0.99) was associated with a decreased likelihood of stricture formation; presence of an endostent (hazard ratio 1.66; 95% confidence interval 1.35–2.04) predicted stricture formation. Conclusion Biliary-enteric anastomotic strictures occur with significant frequency after a biliary-enteric anastomosis. Although many patients are managed nonoperatively, stricture diagnosis remains burdensome.