Mirizzi syndrome is a rare complication of gallstone disease caused by extrinsic compression of the common hepatic duct, resulting in biliary obstruction. We present a 27-year-old female with known cholelithiasis who developed persistent right upper quadrant pain, nausea, and vomiting. Initial imaging showed cholelithiasis without acute cholecystitis, and she underwent robotic-assisted cholecystectomy. Although initially improved, she re-presented weeks later with worsening abdominal pain and new-onset jaundice. Laboratory studies showed transaminitis and hyperbilirubinemia, with imaging revealing biliary ductal dilation. Magnetic resonance cholangiopancreatography confirmed retained cystic duct stones causing extrinsic bile duct compression, consistent with Mirizzi syndrome, emphasizing the need to evaluate postoperative biliary obstruction promptly.