Educational attainment level has long been a strong predictor of adult health and longevity in the United States. Interestingly, the association between education and these outcomes has strengthened in recent decades. Since the 1980s, higher-educated adults have experienced favorable trends in health and longevity, while lower-educated adults have experienced stagnation or unfavorable trends. Studies have provided important clues about why the association between education and health and longevity has strengthened over time. However, explanations remain incomplete and contested. This article discusses key findings and debates about why the association has become stronger and offers recommendations to advance robust explanations. Two key recommendations call for a fundamental shift in how researchers conceptualize and study the increasingly strong association. These include (a) reconsidering which education groups should be viewed as normative in analyses of the trends and (b) elevating attention on contexts, institutions, and actors that have had an outsized influence on the trends.