The current study examined whether stress reactivity becomes stronger or weaker with age. Daily stress and daily negative affect were modeled using 1,012 subjects from the National Study of Daily Events (NSDE), an 8-day daily diary study. Age ranged from 25 to 74. Data were modeled using within-person HLM techniques. Daily stress and neuroticism interacted in their effect on daily negative affect. There was a stronger association between daily stress and negative affect for persons high in neuroticism as compared to those low on the trait. In addition, daily stress and age interacted in their effect on daily negative affect. There was a stronger association between daily stress and negative affect for older as compared to younger adults. Results suggest heightened reactivity to stressors in older adulthood, perhaps due to kindling effects. Changes in the aging brain may explain this effect. Our investigations illuminate the complexities that characterize the set of associations among negative affect, stress, personality, and age, and point to potential aging or cohort effects.