This study explored the idea of “flourishing under fire” to determine whether a ratio of positive to negative affect could predict high levels of well-being for older adults with multiple chronic health conditions. Using a sample of elders either living in the community (n = 762) or a nursing home (n = 53), we calculated ratios of positive to negative affect and measured well-being with several indicators. The 2.9 positivity ratio differentiated high levels of well-being in both samples. The ability to regulate positive affect to maintain a higher ratio of positive over negative affect appears to be important to successful late life adjustment.