If work routines function smoothly within organizations, they often do so not because of formal decision programs and communication channels, but despite the (well-intentioned) formal structure. The basis for success lies more in informal expectations, because they offer much more freedom to react flexibly to unexpected situations. This is all the more true in comparison to the strict if-then rules of conditional programs, which define all relevant events (the “if” component) and reactions to them (the “then” component) in advance. This dilemma—in which measures aimed at ensuring compliance with rules simultaneously threaten and restrict the flexibility of specialist departments—is well known in principle. Some of the illuminating contributions to the debate on compliance management therefore point out that the strict formal orientation of compliance management and the delegitimization of informal practices can have dysfunctional consequences for the organization.