Patients cope in different ways when living with an incurable cancer. These varied coping styles impact how oncology providers communicate with patients. If providers do not tailor communication with a general understanding of how a patient is coping, this risks miscommunication with the patient, inaccurate disease understanding, and suboptimal care. This review explores the spectrum of coping patterns that influence a patient's behaviors and communication with their oncology team throughout a cancer course. We then review several strategies to assist with coping in order to provide more transparent communication throughout the cancer course. Patients express coping styles on a spectrum, from “avoidant” to “resistant” to “engaged.” The “avoidant” and “resistant” coping styles often impede transparent communication between patient and provider due to expressions of unrealistic hope by the patient. Several communication skills can improve patient coping and readiness to discuss prognostic information about the cancer, which will better facilitate conversations around end of life and readiness to stop cancer treatment and initiate hospice when indicated. Understanding the spectrum of coping styles and stress responses by patients and families can improve shared understanding between patient and provider as well as a sense of partnership with patients and families.