Background: Various technical improvements have decreased the morbidity and mortality after pancreaticoduodenectomy. However, postoperative pancreatic fistula (POPF) is the most feared complication, and the ideal technique for pancreatic reconstruction is undetermined. The aim of this study was to identify the risk factors and incidence of POPF with different types of pancreatic stump management after robot-assisted pancreaticoduodenectomy (RAPD). Materials and Methods: This study is a retrospective review of consecutive patients who underwent RAPD at the University of Illinois Hospital and Health Sciences System between September 2007 and January 2016. The cohort was divided based on the type of pancreatic stump management: pancreatic duct occlusion with cyanoacrylate glue (CG), pancreaticojejunostomy (PJ), posterior pancreaticogastrostomy (PPG), and transgastric pancreaticogastrostomy (TPG). Results: The cohort included 69 patients: pancreatic duct occlusion with CG (n = 18), PJ (n = 12), PPG (n = 11), and TPG (n = 28). Pancreatic duct diameter < 3 mm and duct occlusion with CG were identified as risk factors for POPF (p < 0.05). The incidence of POPF was lower when TPG and PJ were performed (p < 0.001). Conclusions: Reconstruction with PJ and TPG had better results compared to pancreatic duct occlusion with CG and PPG. However, TPG was the technique of choice and showed comparable results to PJ.