Cholelithiasis and its complications are among the most prevalent and costly medical conditions in the United States. Chronic gallbladder disease can progress into more complicated conditions, such as a cholecystoenteric fistula and, more specifically, a cholecystoduodenal fistula (CDF). Repair of these fistulas is complex and usually performed with an open approach. However, if discovered pre-operatively, they can be referred to a hepatobiliary surgery center, where surgeons have specialized training to do such procedures laparoscopically. Here, we present a case of a 57-year-old female with a past medical history of migraines, arthritis, chronic back pain, and fibromyalgia, with no prior surgical history. She presented with an approximately six-month history of colicky right upper quadrant pain and symptomatology consistent with symptomatic cholelithiasis. She elected to have a robotic-assisted laparoscopic cholecystectomy performed. Intraoperatively, she was found to have a CDF and subsequent bile duct leak that were successfully repaired. While more research is required to further characterize and more quickly identify this complication of gallbladder disease, this case highlights the value of robotic-assisted surgery in technically challenging cases. We aim to describe and advocate for the adoption of a robotic approach in patients with comparable presentations, allowing for excellent visualization and control in the removal of inflamed gallbladders, repair of fistulized tissues, and stabilization of bile leaks.