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While uncertainty has always been a feature of the healthcare environment, its pace and scope are rapidly increasing, fueled by myriad factors such as technological advancements, the threat and frequency of disruptive events, global economic developments, and increasing complexity. Contemporary healthcare organizations thus persistently face what is known as “deep uncertainty,” which obscures their ability to predict outcomes of strategic action and decision-making, presenting them with novel challenges and threatening their survival. Persistent, deep uncertainty challenges us to revisit and reconsider how we think about uncertainty and the strategic actions needed by organizations to thrive under these circumstances. Simply put, how can healthcare organizations thrive in the face of deeply uncertain environments? We argue that healthcare organizations need to employ both adaptive and creative strategic approaches in order to effectively meet patients' needs and capture value in the long-term future. The chapter concludes by offering two ways organizations can build the dynamic capabilities needed to employ such approaches.