Pancreaticobiliary obstruction is a rare but life-threatening complication. Plastic biliary stents are a temporary utility to maintain the patency of the common bile ducts, typically lasting about four months. Biliary stents can rarely have complications, with the most common being migration through the gastrointestinal tract. We present a case of a patient with a plastic stent placed over five years, which was complicated by severe hematochezia due to the retention of the stent in a diverticulum. Given the increased risk of life-threatening complications post-stent life expectancy, there should be systems in place to prevent patients from being lost to follow-up.