Striving toward goals is associated with higher levels of subjective well-being; however, many potential roadblocks to goal achievement exist. The current study extends the understanding of goal regulation processes in its examination of the relationships between dispositional and situational goal adjustment to a profound stressor and their associations with psychological adjustment. Women (N = 103; M age = 57.2 years; 82% Caucasian) with metastatic breast cancer completed semistructured interviews and self-report measures at study entry and 3 months later. Measures of dispositional and situational goal reengagement were significantly correlated, but dispositional and situational goal disengagement were unrelated. Greater dispositional and situational goal disengagement abilities were associated with fewer cancer-related intrusive thoughts at Time 1. Dispositional and situational reengagement were positively associated with life satisfaction and sense of purpose and negatively associated with depressive symptoms at Time 1. However, greater initial situational goal disengagement predicted an increase in depressive symptoms over time. Both how an individual typically responds to goal blockage, as well as how an individual is currently responding to a specific blocked goal, appear related to psychological adjustment.