Purpose. The aim of this qualitative study was to close the gaps in our knowledge regarding the decision making experiences, challenges, and frustrations of women when breast cancer recurs. A great deal of attention has been devoted to understanding the decision making processes of women diagnosed with early stage breast cancer (Pierce, 1993, 1999, 2003). However, very little research has been devoted to understanding the challenges women face when the cancer returns to threaten their lives once more. It is not known, for example, if the initial decision making experience supports or impairs the capacity to make decisions regarding recurrent disease. Further, it is not known if the occurrence of recurrent disease causes a psychologically detrimental post-decision appraisal such as guilt, remorse, or regret concerning the decisions made for early stage treatment. Nor do we have sufficient information to fully understand the complexity of the decision problem, or the demands imposed upon the decision maker, of dealing with a cancer diagnosis once again. Method. Intensive face-to-face interviews with 60 women at the time of diagnosis provides an elaborated description of women facing recurrent cancer. Using the constant comparative method, the analysis furthers our understanding of how the initial decision making process shapes the confrontation with decisions inherent in recurrent disease, and how it informs our understanding regarding hindsight bias, regret, decision satisfaction, and resilience in the face of this life-threatening disease. The theoretically challenging task is to find an explanation that accounts for the relative ease with which some women make a complicated and serious medical decision, and the overwhelmingly difficult and stressful experience of others. Results. Analysis of these data reveal ways in which naturalistic decision processes express optimistic bias (looking ahead) and hindsight bias (looking back) and indications of the ways in which the decision making process and cognitive biasing influences decisional and psychological coping with the demands of recurrent disease. Conclusions. From a clinical perspective, it is important to understand the processes which lead women to select unnecessarily aggressive therapies or decline therapy altogether from a sense of despair rather than reasoned deliberation. Further, the importance of understanding this decision lies in targeting areas where structured interventions are needed to improve decision outcomes and quality of life in life-threatening diseases.