Pro-social rule breaking, the volitional violation of explicit organizational rules in an attempt to increase organizational efficiency or to provide a greater service to a stakeholder such as a customer or coworker, has drawn the interest of several theorists in the development of conceptual models. However, scant empirical research exists examining either the reasons that employees are likely to engage in such behaviors or the resulting implications of their actions. As a component of the umbrella construct of positive or constructive deviance, an outgrowth of the positive organizational scholarship movement, pro-social rule breaking, like other prosocial behaviors, has traditionally been conceptualized as a collection of behaviors that are beneficial and should be fostered and encouraged. Yet results to date suggest that employees that engage in pro-social rule breaking are high in risk-taking propensity and low in conscientiousness, a personality profile that may be less than ideal in the eyes of practicing managers. Further, employees who deviate from the organization’s rules to help others also experience negative repercussions through lower performance evaluations as assessed by supervisors as well as coworkers. Therefore, there is much ambiguity surrounding the construct that I suggest is synonymous with organizational martyrdom such that, in seeking to help others, the employee’s career is negatively impacted. I seek to glean important understanding of pro-social rule breaking through a number of approaches. First, through the use of a pilot study, I attempt to replicate and extend earlier categorization efforts as well as develop a collection of narratives to serve as exemplars. Next, I offer a revised conceptualization of pro-social rule breaking such that it is suggested to be the behaviors of good employees in negative contexts who feel constrained by the rules of the organization. Guided by role identity theory, a new theoretical perspective for the literature, I develop an interactionist model that depicts the employees who engage in these behaviors in a more positive light as well as provides the first examination of any contextual antecedents. Central to the dispositional factors of the employees, I suggest that those with salient empowerment role identities are more likely to engage in pro-social rule breaking, behaviors that are congruent with their role identities, as well as provide a collection of more distal antecedents. Additionally, I further suggest that employees who perceive their organization to be highly political, as impacted by the hypothesized causes for these perceptions, will also be more likely to engage in pro-social rule breaking. Finally, I also consider the first boundary condition by assessing how relational factors, as measured by leaders’ behaviors, impact employees’ engagement in pro-social rule breaking before developing a hypothesis for a three-way interaction between the individual, relational and organizational factors and their effect on the enactment of such constructively deviant behaviors. A largely unexplored but critical aspect of pro-social rule breaking requires attention to the implications or outcomes of these behaviors. While the construct was conceptualized to focus on the intentionality behind the behaviors as independent of the outcomes, intentionality is difficult to assess by observers and, as such, responses to the behaviors and the subsequent outcomes may be driven by the behaviors themselves. I seek to advance this understanding by developing a multi-stakeholder perspective of the outcomes of such behaviors. In doing so, I examinee how the reactions from various stakeholders can provide feedback which either confirms or disconfirms the employee’s role identity. Further, I consider whether the same behavior may be perceived differently by various stakeholders such that the categorization as either destructive of constructive deviance may be in the eye of the beholder. I also create a series of hypotheses regarding these perceptions and their implications on future behaviors as well as key organizational attitudes. Through a multi-wave, multi-source field study of 270 employees, I test the hypothesized relationships. Support is found for the majority of the hypotheses which suggest that my adapted conceptualization of the focal construct warrants additional consideration such that pro-social rule breaking may be an outcry by employees who desire empowerment and want to make a meaningful impact but feel restricted by organizational rules within an organization that is perceived to be highly political and under the supervision of a leader who does not support creativity. Additionally, I find support for several important implications of pro-social rule breaking and their subsequent responses from multiple stakeholders. While customers and coworkers generally look favorably on an employee engaging in such behaviors, the organization has the opposite response and these responses guide future behaviors. However, regardless of the direction or source of feedback, having to break rules in order to be more efficient or provide a greater service is likely to lead to perceptions of psychological contract violations and, in turn, low satisfaction and perceptions of fit within the organization. Finally, through the inclusion of a post-hoc exploratory set of analyses I find that other-rated measures may be an acceptable solution in seeking to reduce common method bias in deviance research and that observers are able to distinguish between various forms of prosocial behaviors although biases may still exist in such responses. I then conclude by discussing the implications of the findings for researchers and practitioners as well as how the limitations of the current study provide directions for future research.