Uncontrolled postoperative pain continues despite abundant research in the area. The purposes of the paper are to review how past research influences our understanding of pain in the postsurgery context and to argue for a methodological shift towards naturalistic inquiry. Such a shift incorporates the complexities of pain assessment and management in the clinical practice environment. Decisions regarding pain are often examined outside of the contextual concerns of clinical practice. Research approaches have involved analyses of nurse and patient-related factors associated with pain. These approaches do not account for complex interactions that occur between nurses, patients and the dynamic environment in which these interactions take place. The failure of research to address the context of pain decisions has several implications. It limits our understanding of why pain continues despite ongoing research and it does not enable evaluation of clinical strategies to improve pain decision-making and pain outcomes for patients.