Although prosocial rule-breaking (PSRB) is motivated by honorable intentions to help rather than harm the organization or its stakeholders, relatively little is known about how people interpret and judge the prosocial rule-breaker’s behavior. We propose that PSRB poses a trust dilemma for other organizational members because it pits different values, especially integrity and benevolence, against each other. In four complementary studies, we investigated how observers perceived the tradeoff between integrity and benevolence when they decided whether to trust the prosocial rule-breaker. Studies 1 and 2 experimentally revealed that although observers appreciated the prosocial rule-breaker’s benevolent intentions, their concerns about the person’s integrity dominated their judgments, leading to reduced trust in the rule-breaker. Study 3 extended the first two studies by investigating the effect of PSRB on trust in a unique organizational context where PSRB significantly benefitted the organization and/or the participant. Study 4 replicated the experimental results in a field study, suggesting that coworkers trusted prosocial rule-breakers less in the workplace because they were concerned about the rule-breakers’ integrity. We discuss theoretical and practical implications for prosocial behavior, trust, and rule compliance in organizations.