Background: Military metaphors have long dominated the cancer discourse in America, and patients are expected to be willing to endure anything in order to “fight” and “battle” cancer. In recent years, however, cancer care has expanded in response to a need to better holistically support patients as they undergo treatment. Patients are increasingly referred to psychology, nutrition, and palliative care for co-management. Coupled with the movement in healthcare to engage patients in their care and to provide care that is more “centered” to the patient, these shifts have the potential to radically transform patient experiences of cancer care. However, it is unclear how cancer patients currently view their own roles as well as those of their growing healthcare team. Objective: Using role theory, we sought to identify patients’ and caregivers’ current approaches to patient and healthcare provider roles, in the context of an outpatient cancer care with palliative care. Methods: A qualitative interview study was designed to investigate the perspectives, attitudes, and experiences of patients and caregivers surrounding cancer care, specifically with palliative care and symptom management. Thirty-one interviews were conducted and audio-recorded with patients (n = 18) and caregivers (n = 13). Following a grounded theory approach, we iteratively analyzed our data to develop a typology of approaches. Findings: Patients and caregivers conveyed three approaches to expectations and roles in the context of their cancer care experience. The conventional approach saw fighting cancer as the top priority, and oncologists as the most important healthcare professional. In contrast, the unconventional approach rejected this traditional view and placed more value on aspects of life and care that were outside of their cancer diagnosis; participants with this approach often described instances in which oncologists dismissed critical components of their care. Finally, the ambivalent approach acknowledged gaps in current oncology care, but participants with this approach were quick to defend their oncologist and justify these oversights. Conclusion: Our study showed that patients with cancer are actively shaping the expectations and roles they ascribe to themselves and to their healthcare providers. Interestingly, however, some patients seemed content with a more traditional, paternalistic approach while others described some resistance when trying to advocate for their values and desired illness experiences.