Background: In many Western countries, the state pension age is being raised to stimulate the extension of working lives. It is not yet well understood whether the health of older adults supports this increase. In this study, future health of Dutch adults aged 60 to 68 (i.e., the expected state pension age) is explored up to 2040. Methods: Data are from the Dutch Health Interview Survey 1990–2017 (N ≈ 10,000 yearly) and the Dutch Public Health Monitor 2016 (N = 205,151). Health is operationalized using combined scores of self-reported health and limitations in mobility, hearing or seeing. Categories are: good, moderate and poor health. Based on historical health trends, two scenarios are explored: a stable health trend (neither improving nor declining) and an improving health trend. Results: In 2040, the health distribution among men aged 60–68 is estimated to be 63–71% in good, 17–28% in moderate and 9–12% in poor health. Among women, this is estimated to be 64–69%, 17–24% and 12–14%, respectively. Conclusions: This study’s explorations suggest that a substantial share of people will be in moderate or poor health and, thus, may have difficulty continuing working. Policy aiming at sustainable employability will, therefore, remain important, even in the case of the most favorable scenario.