This study explores the complex relationship between gratitude—a positive, moral emotion—and Unethical Pro-Organizational Behavior (UPB), which involves actions intended to benefit the organization but that violate ethical norms. Using Social Exchange Theory (SET), we theorize two pathways through which gratitude may foster UPB: an indebtedness pathway, where employees feel compelled to reciprocate the organization’s generosity, and a prosocial motivation pathway, where gratitude encourages employees to prioritize organizational success over ethical considerations. Moreover, we introduce organization-oriented moral disengagement (OMD) as a second-stage moderator that intensifies the indirect effect of gratitude on UPB. Using an experimental design with 172 participants, results indicate that gratitude increases UPB, as well as indebtedness and prosocial motivation. While the initial global tests did not support the mediating and moderated mediation effects, supplementary analyses showed that indebtedness significantly mediates the gratitude–UPB relationship. Furthermore, OMD amplifies the indebtedness–UPB link and moderates the prosocial motivation–UPB link only at very high OMD values. These findings challenge the conventional view of gratitude as a purely positive, moral influence, demonstrating that gratitude can, in certain organizational contexts, lead individuals to prioritize the organization’s interests over ethical standards. Practically, organizations should integrate ethical training with gratitude initiatives to harness gratitude’s benefits while mitigating potential UPB.