This paper briefly lays out the well-known obstacles to surrogate decision-making that comports with incapacitated patients’ wishes, but then focuses primarily on exploring an additional layer of complexity that makes surrogate decision-making even more challenging. Health care agents face particularly vexing obstacles to making decisions for their incapacitated family members. A combination of factors impact the objectivity and reliability of the process. In addition, there is another decision-making realm in which the added complexities of bounded rationality, clinical uncertainty and overall Knightian uncertainty provide insurmountable, unalterable barriers to confident rational surrogate decision-making. The combination of all of these factors often leads health care agents to consent to more care than the incapacitated patient might have chosen. Even in situations in which the medical decision itself is simple to comprehend, the broader ethical and cognitive challenges inherent in such a decision are daunting. Recognition of the role of clinical uncertainty and resultant rational apathy in health care decision-making may help physicians to more effectively guide surrogate decision-making. This in turn may help surrogate decision-makers in their quest to make good decisions on behalf of patients and may provide surrogates with some comfort that they have done well in the face of an emotionally and morally challenging dilemma. Finally, it is important to recognize that there are two worlds of end-of-life care—one for low-income, uninsured patients, and another for the well-off, educated, well-insured patients. Empirical research demonstrates that minority race and lower socioeconomic status are associated with poorer patient ratings of health care quality and provider communication at the end of life.