Introduction Operative complications after pancreatoduodenectomy can be managed by nonoperative or operative interventions. The aim of this study was to analyze the shift in management of five major complications and their success rates. An algorithm was developed according to predictors for type of intervention and failure of management. Methods From 1992–2012, patients with pancreaticojejunostomy, hepaticojejunostomy or gastroenterostomy leakage, postpancreatectomy hemorrhage, or primary abscess after pancreatoduodenectomy were selected from a prospectively maintained database. Complications were treated by nonoperative or operative intervention Two cohorts were created according to period of index operation. Pre- and postoperative characteristics were analyzed. Results Of 1,037 patients, 263 (25%) experienced operative complications. The incidence of pancreatic fistula increased from 11 to 18%, accompanied by a shift from operative toward nonoperative management. This was also seen in the management of late hemorrhage. Success rates of interventions remained similar for all complications. The incidence of primary abscesses decreased. Early sepsis (odds ratio [OR] 17.8, 95% confidence interval [CI] 4.9–64.4) was associated with failure of nonoperative interventions in patients with pancreatic fistula. Hemodynamic instability (OR 17.2, 95% CI 1.8–160.1) and sepsis (OR 6.7, 95% CI 2.7–16.3) were predictive for operative intervention. Failure of nonoperative intervention (HR 3.95% CI 1.3–7.1) and operative intervention (HR 6.4 95% CI 3.2–12.8) were predictors for poor survival. Conclusion The shift towards nonoperative interventions was notable in patients suffering from pancreaticojejunostomy leakage and late hemorrhage. Anastomotic leakage, late hemorrhage, and primary abscesses can be managed nonoperatively however; hemodynamic instability and early sepsis are strong arguments to perform surgery.