Seriously ill surgical patients require complex and integrated surgical, interventional, and medical management to balance the risks and benefits that complicate decision-making. Palliative care principles can aid surgeons in these cases. To illustrate this, we describe a scenario of a patient with unresectable hepatocellular carcinoma with portal vein tumor thrombus causing portal hypertension. We discuss options for managing the sequelae of portal hypertension, including varices and ascites. We explore the interventional and surgical options for mitigating or palliating the underlying portal hypertension. Advances in interventional radiological techniques can facilitate the creation of transjugular intrahepatic portosystemic shunts (TIPSs), even with extensive portal vein thrombus. If interventional approaches are not possible, surgical shunts can be considered but carry significant risks that must be weighed against the benefits. To communicate effectively, we outline key steps to breaking bad news. To make shared decisions in challenging cases, we describe how to elicit a patient’s hopes, expectations, concerns, and preferences; how to synthesize goals of care from these stated values; and how to use those goals to guide decision-making.