I'm presenting a case of recurrent ascending cholangitis after Roux-en-Y hepaticojejunostomy. The patient is a 50 year-old woman who had open cholecystectomy in 1994. Postoperative course was complicated by recurrent cholangitis presumably secondary to biliary stricture requiring open Roux-en-Y hepaticojejunostomy in 2008. We first evaluated her for morbid obesity in 2014 and elected to perform vertical sleeve gastrectomy so as not to complicate her biliary tract reconstruction. She did well postoperatively and lost 70lbs. However, she developed another episode of cholangitis in 2016. A percutaneous transhepatic cholangiogram showed no anastomotic stricture or biliary dilation, but rapid transit of contrast into the Roux limb, suggestive of enteric reflux as the cause of her recurrent cholangitis. She was then lost to follow-up, but returned in 2019 with severe pain and was found to have a hepatic abscess which was percutaneously drained. After significant consideration, we decided to lengthen her Roux limb in an attempt to decrease the enteric reflux. However, upper endoscopy performed at the beginning of the operation showed 3 choledochoduodenal fistulas, suggesting that the recurrent cholangitis was most likely secondary to enteric reflux from these fistulas and not from the pre-existing Roux limb. In order to completely divert the gastric contents away from the biliary system, decision was made to convert her sleeve gastrectomy to a Roux-en-Y gastric bypass. She did well after the conversion and has not had any episode of ascending cholangitis or hepatic abscesses in more than a year.