A simple discussion of compliance suggests that organizations either comply with or disobey the prescript of the legal norm, on the basis of a cost-benefit calculation. The literature on compliance has already demonstrated that this simple model of compliance does not fully capture the gamut of incentives for compliance, or the continuum of behaviours that ranges from defiance to compliance. Drawing on a case study of an Israeli legal norm that requires employers to reinstate workers after postpartum parental leave for sixty days, we seek to further unpack the notion of compliance along two axes. First, the duty to reinstate is ‘ambitious’ because it seeks to affect managerial bias and educate for virtue within organizations. Second, the study of compliance must open the fictitious black box of organizations, and reveal internal negotiations over the extent and form of compliance. Based on a qualitative study, we demonstrate that even a seemingly strict norm is applied and perceived differently, between and within the same organization. Findings identify the strengths as well as the shortcomings of the legal ambition to induce an educational experience in organizations.