A cholecystoenteric fistula is an anomalous communicating tract between the gallbladder and any segment of the gastrointestinal tract. It is a rare complication of gallstone disease and typically affects elderly patients with multiple medical comorbidities. These fistulae can present in a variety of ways, and the diagnosis is often made only after extensive workup. Despite notable advances in imaging techniques in the last half-century, a considerable number of cases are still discovered incidentally during open or laparoscopic surgery. We present a series of 3 cases, each with different etiologies and presentations, but all of whom were found to have a cholecystoenteric fistula. Each case was managed differently, highlighting the diversity of this intriguing condition.