A 60-year-old female with chronic pancreatitis and a history of splenectomy presented with epigastric pain, vomiting, and asthenia. Elevated pancreatic enzymes and CT imaging revealed a pseudocyst in the pancreatic head with suspected communication to the portal vein, confirmed by MR Cholangiopancreatography and endoscopic ultrasound (EUS). EUS-guided puncture revealed high amylase levels. Given her manageable symptoms, a conservative approach was adopted, leading to symptomatic relief and pseudocyst size reduction. Pancreatic pseudocyst-portal vein fistula is a rare pancreatitis complication, challenging to diagnose, with no gold-standard treatment. Endoscopic stenting offers a promising alternative to surgery for severe cases.