Abstract Introduction Cholecystocoloic fistula (CF) is a rare sequelae of biliary stone disease with a 2% prevalence, previously it was considered a contraindication for laparoscopic management. Preoperative diagnosis can be very challenging, the pathognomonic triad of Pneumobilia, chronic diarrhoea, and vitamin K malabsorption should raise a high index of suspicion but is not always present, furthermore, preoperative imaging (EUS, ERCP, and Barium enema) help in the diagnosis, however, those are not routine practice in investigating typical biliary colic presentation. Case presentation We report a Cholecystocoloic fistula diagnosed intraoperatively and successfully managed with a laparoscopic approach. A 63-year-old male with a background of hemiplegia and aphasia followed a surgical treatment for intracranial haemorrhage 12 years ago. He presented with recurrent attacks of acute calculus cholecystitis investigated by US and CT scans, and both have failed to detect CF. During his previous admission, he was managed conservatively and added to the elective laparoscopic cholecystectomy list. His surgery was challenging, Intraoperative findings revealed a gallbladder adherent to the surrounding omentum and transverse colon, with a fistulous communication of the gallbladder fundus to the transverse colon, the fistula was divided, and the colonic opening was sutured. The surgery was uneventful and he was discharged home after 18 hours with no postoperative complications. Conclusion A high index of suspicion should be raised for Cholecystocoloic fistula diagnosis intraoperatively, especially with a history of long-term recurrent cholecystitis even in the absence of usual presentation and imaging. Moreover, a laparoscopic approach is possible and successful in experienced hands.