Concurrent malignant biliary and gastric outlet obstruction requires urgent palliative intervention to improve patient quality of life and permit systemic therapy. Traditional management has been surgical gastrojejunostomy and hepaticojejunostomy, two morbid procedures. Comparatively, endoscopic stenting can relieve both sites of obstruction with less complications and quicker recovery. In patients with previous plastic biliary stents in situ, it is crucial for subsequent bilioduodenal obstructions to be managed with proper sequencing and precise stent placement to achieve successful bilioduodenal patency. We report a case of a 53-year-old male patient who presented with simultaneous jaundice secondary to blocked biliary stent and vomiting due to gastric outlet obstruction at the first part of the duodenum on background of unresectable pancreatic adenocarcinoma. Fourteen months prior, he had a plastic endobiliary stent placed for biliary obstruction secondary to choledocholithiasis, but intraprocedural cholangiogram also revealed a distal common bile stricture with subsequent investigations revealing unresectable pancreatic adenocarcinoma for which he underwent palliative chemotherapy. Duodenal stricture dilation with subsequent duodenal self-expanding metal stent was placed under direct endoscopic vision precisely proximal to the blocked biliary stent. After 48 hours, endoscopic retrograde cholangiopancreatography was then performed through the duodenal stent to exchange the blocked plastic biliary stent for a metal biliary stent. The patient had prompt relief of jaundice and tolerated oral intake by date of discharge post-procedure day two and was initiated on chemotherapy on post-procedure day 12. Endoscopic stenting of concomitant biliary and gastric outlet obstruction can be successful in patients with occluded indwelling plastic biliary stents.