This study proposed a conversation analytic (CA) investigation of the interactional organization of pain communication during cancer care. Transcriptions and video recordings of patient-provider interactions during clinical encounters were analyzed to closely examine how issues of pain are raised, responded to, and negotiated between cancer patients and their doctors. Pain is a unique symptom of illness, injury, or disease because there is often a physical element that cannot be measured, evaluated, or treated by doctors without co-constructed communication. Pain is inherently dispreferred and yet commonly misunderstood due to its dynamic nature and the malleable nature of how pain gets expressed and interactionally negotiated. Only minimal attention has been given to analyzing interactional moments when patients and providers talk about and through “pain.” Yet little is known about how patients raise and respond to pain. Three practices are examined for expressing pain to doctors: upgrading, downgrading, and combinations of both. Close examination of these social actions provides basic knowledge about pain communication, implications for future research, and insights into how clinical practice and medical education can be improved by understanding the complexities of communication about pain.