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Only recently has research started to examine relationships between proactive behavior and employee well-being. Investigating these relationships is important for understanding the effects of proactivity at work, and whether proactivity leads to an increase or a decrease in well-being. In this study, we investigated day-level effects of proactive behavior on four indicators of occupational well-being (i.e., activated positive and negative affect, emotional work engagement and fatigue). Moreover, based on theorizing on “wise proactivity,” we examined organizational tenure and emotion regulation as moderators of these effects. In total, N = 71 employees participated in a daily diary study with two measurements per day for ten consecutive working days. Results revealed that emotion regulation interacted with daily proactive behavior to predict daily emotional work fatigue, such that the effect of proactive behavior on emotional work fatigue was only positive for employees with low (vs. high) emotion regulation. Supplementary analyses examining reverse effects of occupational well-being on proactive behavior showed that organizational tenure interacted with daily activated positive and negative affect in predicting proactive behavior. For employees with lower (vs. higher) organizational tenure only, both activated positive and negative affect were negatively associated with proactive behavior. Overall, our findings contribute to the growing body of research on proactive behavior and well-being by demonstrating reciprocal and conditional day-level relationships among these variables.