The excitement about immunotherapy is justified. Patients with advanced disease and limited life expectancy before immune checkpoint inhibitors are now having prolonged and sometimes complete responses to treatment; however, most patients do not respond to checkpoint inhibitors. The hope for a meaningful response with only a limited risk of high-grade toxicity generated a prognostic dilemma for patients with advanced cancers and their treating oncologists. Older adults with advanced cancers are at the intersection of multiple biologic and clinical factors that can influence the efficacy of immunotherapy. Treating physicians should take all of these elements into account when considering treatment options for an older adult with advanced disease. Oncologists should have an honest conversation with their patients regarding the uncertainty around the clinical profile of checkpoint inhibitors. Early high-quality goals of care discussions can help manage expectations of older adults with advanced cancer treated with immunotherapy. We review in this paper select clinical characteristics that are important to consider when evaluating an older adult for checkpoint inhibitor therapy. In addition, we discuss strategies to optimize goals of care discussion given the increasing complexity of prognostication in the immunotherapy era.