As contemporary organizational life is increasingly rule governed, organizational actors, most notably professionals, perform their work by complying with institutional rules, stemming from regulatory bodies external and internal to organizations. This begs a question of the role of agency in compliance with institutions that is largely ignored within organization theory. A weak form of agency in compliance is found in practice theory and practice-driven institutionalism, in terms of actors mindful enactments of institutions on the basis of mastering shared practices for applying institutional rules. These are characterized as first-order practices of compliance with institutions. Extending the Wittgensteinian-inspired philosophical foundation of practice theory, modes of compliance in so-called “hard cases,” where shared practices do not apply as a basis for agreement in following institutional rules, is conceptualized as second-order compliance practices, involving a strong mode of agency. In these cases, the aim is to reach agreement on how rules are to be applied beyond established first-order practices by engaging larger frameworks of shared forms of life and more open and explorative attitudes to move institutions forward for a common good. It is argued that second-order compliance can be understood as a politico-ethical mode of agency in the Kantian tradition, supplementing prevalent notions within organizational institutionalism of agency as primarily political.