Roux-en-Y (RY) hepaticojejunostomy (HJ) is a critical component of complex hepatobiliary operations, and it is the treatment of choice for post-cholecystectomy biliary strictures (PCBS). Complications related to the Roux limb, particularly those leading to cholangitis, can severely compromise outcomes. We present a case of a 54-year-old lady who had previously undergone two HJ procedures for recurrent PCBS. The same Roux limb had been used in each of the operations. Short Roux/Roux reflux syndrome led to recurrent cholangitis in this patient, as proven by the reflux of oral contrast into the biliary tree on imaging. This was effectively treated by lengthening the Roux limb (60 cm) with a redo-jejunojejunostomy, and creation of a Nakajo type valve. One-year post surgery, the patient remains well at follow-up. Enteric reflux into the biliary tree may lead to refractory cholangitis. We present the first ever case in an adult, where a simple and effective modification to the HJ obviated this complication.