The question of how high-performance work systems (HPWSs) impact organizational performance is no longer novel in research. However, the mechanisms that underpin this relationship, often referred to as the “black box” of HRM, remain controversial. The mutual gains perspective suggests that HPWSs enhance employee well-being, leading to performance improvements, whereas the conflicting outcomes perspective argues that such gains come at the expense of employee well-being. Moreover, little attention has been paid to the role of individual dispositions in moderating the relationships between HPWSs and employee-employer outcomes. Integrating Job Demands Resources (JD-R) model and Transactional Theory of Stress (TTS), we aimed to unpack the processes through which HPWSs influence individual and organizational outcomes. Further, we examined the moderating role of dispositional “grit” as a critical contingency influencing these underlying mechanisms. Drawing on the JD-R theory, our results suggest that HPWSs are positively related to performance pressure. However, consistent with the TTS, our findings highlight the paradoxical effects of performance pressure. When performance pressure is appraised as a threat, HPWSs lead to psychological stress. Conversely, when performance pressure is appraised as a challenge, HPWSs enhance job performance. We found significant support for the role of grit in shaping employees’ responses to performance pressure stemming from HPWSs. Overall, our results indicate that HPWSs produce conflicting outcomes. Theoretical and practical implications of these findings are discussed.