The burden of depression is exacerbated by its chronic and recurrent nature, as studies have estimated that on average, individuals with depression will experience five to nine depressive episodes in their lifetime, with the risk of relapse increasing with each consecutive episode. The differential activation hypothesis proposes that an individual’s heightened risk of relapse with each episode is due to cognitive reactivity to changes in depressed mood. With cognitive reactivity, the association between negative cognitive patterns and depressed mood is strengthened with each consecutive episode, such that milder negative events or dysphoric moods are required to re-activate negative thinking patterns. Once activated, maladaptive cognitive patterns likely play a key role to intensify depressed mood and potentially trigger relapse. The current study examined the hypothesis that cognitive reactivity varies as a function of depression chronicity. More specifically, the study explored whether individuals with more chronic depression would be more likely to engage in ruminative and negative thinking patterns following a negative mood induction procedure than individuals with less chronic depression. The results of the study indicated that in a sample of recurrently depressed participants in remission, both groups evidenced cognitive reactivity in a low mood state; however, this activation of rumination and negative thinking did not differ based on chronicity, despite adoption of multiple definitions of chronicity. These findings call into question the use of the cognitive reactivity hypothesis to explain the increased risk of relapse with consecutive depressive episodes. The current study provides a unique contribution to the literature, as it represents the first examination of cognitive reactivity as a function of chronicity. The implications of the study, the strengths and limitations of the current research, and the directions for future research are discussed.