The authors report a patient who underwent elective cystogastrostomy for pancreatic pseduocyst and had three episodes of massive gastrointestinal bleeding postoperatively. The patient had bleeding vessels in the pseudocyst cavity of which conservative management of cold saline lavage and octreotide was instituted. Endoscopy was done after the 1st episode of bleeding and showed no active bleeding, no suture site bleeding and with blood clots inside the cavity. After the 2nd episode of gastrointestinal bleeding, there was a note of pinpoint hemorrhages on the pseudocyst wall. The plan was to do angiography but the patient succumbed to hypovolemic shock due to gastrointestinal bleeding hours after endoscopy. On retrospect, early angiography and possible embolization should have been done. Prompt surgical re-exploration is warranted among patients with hemodynamic instability.