There is individual variation in the extent to which individuals believe it is acceptable to violate legal rules. However, we lack a specific measure that assesses this key internal element of legal decision-making and offending. This article describes the development, validation, and testing of the Rule Orientation scale. At its core, the construct captures the extent to which one thinks about rules in a rigid, rule-oriented manner or in a manner that recognizes exceptions. In the first study, we develop the Rule Orientation scale, demonstrate its convergent and divergent validity with key legal and moral reasoning scales, and find that Rule Orientation relates to hypothetical offending behavior across a variety of low-level crimes. In the second study, we examine whether Rule Orientation predicts the propensity to engage in digital piracy both with and without the explicit threat of punishment. The results indicate that Rule Orientation plays a crucial role in predicting offending behavior and, importantly, does so across enforcement contexts. The findings suggest that an individual with low Rule Orientation may be able to justify offending regardless of whether a system explicitly declares an enforcement campaign, regardless of how the individual perceives the severity of the threatened sanction, and regardless of whether the individual believes social norms support law violation. In understanding ethical decision-making, criminal decision-making, and other strands of legal decision-making, identifying such individual variation is crucial.