Surgical clip migration post-laparoscopic cholecystectomy is a rare but important complication to consider in patients presenting with biliary obstruction. Titanium surgical clips are widely used in laparoscopic surgery to ligate vessels and ducts and are particularly important in laparoscopic cholecystectomy to ligate the cystic duct. More common complications associated with clips involve dislodgement, however, there are reported cases of migration into visceral structures causing an obstruction. We describe a case that demonstrated an acute migration of surgical clips into the common bile duct (CBD) within a three-week period, which occurred 32 years after laparoscopic cholecystectomy, likely attributed to erosion. On the patient's first presentation, she had acute pancreatitis with a CT demonstrating clips in the correct position. Three weeks later, the patient presented a second time with acute cholangitis and the repeat CT demonstrated the clips in the CBD. We hypothesize that the erosion of the bile duct is due to the pressure effects from either intra-abdominal organ movements or subtle clip movements, and eventually, persistent erosion leading to intra-ductal migration of the clips with the passage of the clips along the path of least resistance into the CBD, resulting in biliary obstruction. Management included standard treatment for biliary obstruction with intravenous broad-spectrum antibiotics and endoscopic retrograde cholangiopancreatography with excellent outcomes.