We apply the concept of liminality to the analysis of legality and illegality in organizations. Considering the centrality of rules to modern organizations and the potential discrepancy between general rules and specific situations, people are often confronted with a dilemma: apply the rules even when they should not be applied or bend the rules to improve their applicability. If they do what they should do (adapt the rules to the circumstances), they will be doing what they should not do (disrespecting the rules). This double binding situation forces people to slip into a liminal space, betwixt and between, accepting the structure while, at the same time, challenging it. The situation of liminality must eventually be solved, but it confronts individuals with the limits of legality. The relationship between liminality and illegality is explored, and some implications for the control legal and illegal networks extracted.