Scholars agree that counterproductive work behavior (CWB) is instigated by psychological contract breach and feelings of violation. This article focuses on the mediating role of feelings of violation (a mixture of negative emotions) in the relationship between psychological contract breach and CWB, and assesses whether volunteers and paid employees experience a similar chain of events. The study uses Mplus 7 to estimate a moderated mediation model with bootstrapping. The results indicate that both paid employees and volunteers (1) experience feelings of violation when perceiving psychological contract breach, and (2) engage in CWB targeted to the organization (CWB-O) when experiencing feelings of violation. However, these relationships were not significantly different when comparing paid employees and volunteers. It is hence concluded that a similar chain of cognitions and emotions explains why volunteers and paid employees engage in CWB-O. In unraveling this sequence, possibilities for targeted interventions are suggested.