The synchronous presentation of multifocal pancreatobiliary tumors is a rare occurrence and can prove to be a significant diagnostic and therapeutic challenge. We describe the case of a 70-year-old female who presented with a 2-week history of jaundice, reduced appetite, and mild epigastric discomfort of insidious onset. Radiological evaluation with computed tomography and magnetic resonance imaging demonstrated features consistent with a hilar cholangiocarcinoma , also known as a Klatskin tumor, involving both the cystic duct and gallbladder neck. In addition to this, a pancreatic neoplasm with associated splenic vein occlusion and metastatic deposits in the liver and lung were identified. The patient was managed with percutaneous transhepatic external biliary drainage and stenting by interventional radiology. Cytology results from the brushings obtained from the aforementioned procedure were nondiagnostic. Core biopsies were performed of the pancreatic lesion; the histopathological results of which were in keeping with pancreatic ductal adenocarcinoma . The patient was scheduled for chemotherapy however unfortunately deteriorated clinically prior to commencement. This case highlights the diagnostic and management challenges of synchronous pancreatobiliary malignancies.