This article presents an argument for framing chronic pain within a complex adaptive systems (CAS) paradigm. The first aim of this article is to demonstrate how chronic pain can be framed as a CAS and how paradox, one of the core characteristics of a CAS, exists within the chronic pain experience. The second aim is to illustrate how paradox exists at multiple levels within the health care encounter and ongoing experience of chronic pain. Finally, the article will use the example of interactions at the patient/clinician level to illustrate how health care workers' efforts to deal with issues emergent from the range of paradoxes have for the most part been ineffective, and at times harmful, to persons experiencing chronic pain. This article uses the example of chronic pain to explore how the manner in which health care providers and patients recognize and deal with paradoxes can either worsen the pain experience or help generate creative new ways to manage the chronic pain condition. The CAS principles discussed in this article hold application across a range of chronic conditions for which a traditional biomedical paradigm proves insufficient.