In response to a number of late, repetitive bleeding episodes from the site of the enteric anastomosis, we herein analyze the clinical courses and etiologies of 379 consecutively performed pancreas transplants between January 2000 and December 2016. Duodenojejunostomies for enteric drainage were performed at the upper jejunum in a side to side, double layer fashion. Five patients (1.3%) developed recurrent late hemorrhagic episodes originating from the graft duodenal anastomosis. Bleeding from the anastomotic site was associated with hematochezia, hemodynamic instability and decrease in serum hemoglobin. Mean onset was 6.4(±2.8) years after transplantation. Bleeding was recurrent (mean 5.2 ± 2.6) and required 9(±2.5) interventions. Hypervascularization, mucosal vulnerability, and bleeding at the site of the enteric anastomosis could be identified in all cases. In four patients, the enteric pancreas anastomosis was resected and a new duodenojejunostomy was performed. No pancreas graft loss occurred due to bleeding. In two patients, hepatic cirrhosis and portal hypertension were identified, one patient had a liver fibrosis as putative cause for the repetitive bleeding episodes. Late anastomotic hemorrhage is a rare but severe complication following pancreas transplantation. The treatment is challenging and includes endoscopy, interventional radiology, and surgery. Hepatic conditions with an increased portal pressure may be the underlying cause.