<p>Workplace boredom, an unpleasant emotional experience, is predominantly associated with detrimental outcomes. Yet emerging scholarly debate suggests potential variability in employees’ responses to this phenomenon. Based on the control-process model of coping with boredom, we examined the dual-path mechanisms through which workplace boredom may relate to counterproductive work behavior (CWB) and organizational citizenship behavior (OCB). Through two studies involving a scenario experiment (<i>N</i> = 97) and a three-wave survey (<i>N</i> = 149), the results consistently indicated that workplace boredom had a positive indirect effect on CWB through the dimension of sensation seeking—disinhibition, while the indirect effect was stronger when trait self-control was lower rather than higher. However, meaning seeking did not significantly mediate the relationship between workplace boredom and OCB, nor did trait self-control serve as a moderator in this relationship. These findings deepen our understanding of workplace boredom and offer evidence-based strategies for mitigating its detrimental effects in organizational settings.</p>