In an age of widespread background checks, we ask how managers in different organizational contexts navigate legal ambiguity in assessing applicants' criminal history information, based on interview data obtained in a recent field experiment. The study builds on institutional analyses of the social sources of workplace legality to describe how employers consider applicants with criminal histories. We find that some organizations set explicit standards to guide hiring decisions, providing concrete policies on how to treat applicants with records. Where such procedural mandates are lacking, however, hiring managers turn to a micro-rational decision process to evaluate potential risk and liability. These individualized approaches create inconsistencies in how the law is interpreted and applied across organizations, as evidenced by actual hiring behavior in the field experiment.