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Based on the differential reactivity model of personality and stress, we examined the Big Five personality traits as predictors of individual differences and changes in the perceived stressfulness of the COVID-19 pandemic in Germany between early April 2020 and early September 2020. This timeframe includes the national “lockdown” period (early April 2020), the period of “easing” of restrictions (early May 2020 to early July 2020), and the summer vacation period (early August 2020 to early September 2020). Data were collected from n = 588 respondents who provided baseline data on their personality traits in early December 2019, and then later provided data on perceived stressfulness of the COVID-19 pandemic at five time points, spanning six months. Consistent with hypotheses, results showed that, on average, perceived stressfulness declined between early April 2020 and early September 2020. Moreover, this effect was stronger between early April 2020 and early July 2020. Emotional stability was associated with lower, and extraversion associated with higher, average levels of perceived stressfulness. Finally, extraversion was associated with increases (i.e., positive trajectories) in perceived stressfulness between early April 2020 and early July 2020 and decreases (i.e., negative trajectories) in perceived stressfulness between early July 2020 and early September 2020.