A 54-year-old male with cirrhosis and portal hypertension developed recurrent upper GI bleeding after transjugular intrahepatic portosystemic shunt (TIPS) placement. Severe anemia and hypotension ensued, with imaging revealing a hepatic artery pseudoaneurysm and arterio-biliary fistula. Arterio-biliary fistulas, though rare, are serious complications often linked to trauma or iatrogenic injury. This case highlights the importance of early recognition, imaging, and multidisciplinary management in high-risk post-TIPS patients to prevent catastrophic outcomes.