For a long time, it has been held by both academics and practitioners in the field of management that the behavior of violating or breaking an organization’s formal rules displayed by employees is self-interested, deviant, and detrimental to the organization. In 2006, Morrison introduced a more nuanced perspective on rule breaking, suggesting that some type of rule breaking may be motivated by positive intentions and beneficial to the organization. She further developed and empirically tested the construct of pro-social rule breaking (PSRB). The present research employed a scenario experiment and a field study to examine the effect of benevolent leadership on employee PSRB by focusing on the moderating role of organizational uncertainty and employee values (i.e. zhong-yong and power distance orientation). The scenario of the experiment described certain situation in which an employee had to decide whether or not to break a rule by placing an urgent order for a large, important customer. The study used a between-subjects design in which benevolent leadership (high or low) and organizational uncertainty (high or low) were manipulated, resulting in four versions of scenarios. Totally, 126 part-time MBA students were randomly assigned to one of the scenario versions. At the end of each scenario, participants responded to four questions which were included as checks of the organizational uncertainty and benevolent leadership manipulations. Then, they responded to five questions that assessed the likelihood that they would break the rule. Finally, respondents completed a short survey that assessed zhong-yong and power distance orientation. The results of the experiment revealed that: (1) Benevolent leadership impacted positively on employee PSRB. (2) Organizational uncertainty related positively to employee PSRB and moderated the relationship between benevolent leadership and employee PSRB, such that this relationship was weaker when organizational uncertainty was high. (3) Zhong-yong and power distance orientation had significant negative influences on employee PSRB. Meanwhile, power distance orientation also moderated the association of benevolent leadership with employee PSRB in such a way that it was stronger for employees low (versus high) in this orientation. The sample of our field study consisted of 187 employees from enterprises located in South Jiang province. Cronbach’s alpha coefficients for the measures were from 0.73 to 0.95, showing acceptable measurement reliabilities. Results of confirmatory factor analysis indicated the discriminant validity of the measurement was also satisfactory. Results of hierarchical regression modeling replicated most of those findings in the scenario experiment except the negative effect of zhong-yong on employee PSRB. As to the specific moderating patterns of the moderators, results from the two studies consistently showed that organizational uncertainty worked as a substitute for benevolent leadership to increase employee PSRB, while employee power distance orientation acted as a buffer or neutralizer to weaken the benevolent leadership-employee PSRB linkage.