Previous research has largely assumed that organizational culture and leadership influence counterproductive work behaviors (CWB), however, the main empirical focus has excluded these macro-level, contextual predictors, focusing instead on easy to test antecedents (e.g., individual differences and justice perceptions) of CWB. The present study theoretically and methodologically challenged these trends and built upon current CWB, cooperation, and reciprocity theories within an interactional psychology framework that emphasized the importance of context. The current study theoretically built upon and empirically tested a multi-level model explaining how various interactions between organizational culture types, transformational leadership, interpersonal justice, and individual differences specifically influence organizationally-targeted counterproductive work behaviors. Data was collected within subunits of numerous large, national organizations across multiple sites. Surveys were distributed and collected electronically. Hierarchical linear modeling results demonstrated significant interrelationships between organizational culture types, conscientiousness, and organizationally-targeted counterproductive work behaviors.