Hemorrhage associated with anticoagulation therapy is a feared and relatively common complication. Few cases have been documented of spontaneous pancreatic hemorrhage related to anticoagulation, and fewer yet of ruptured pancreatic pseudocyst secondary to anticoagulation-related bleeding. We describe the case of a 74-year-old female with massive intra- and extraperitoneal hemorrhage secondary to an anticoagulation-related ruptured hemorrhagic pancreatic pseudocyst that was treated successfully with coil embolization. An inferior vena cava filter was placed at the same time as the embolization procedure, as she had a contraindication for anticoagulation in the setting of submassive pulmonary emboli and lower extremity deep venous thrombosis.