Being a professional is associated with having a significant degree of freedom in performing one’s work; but social workers, like many professional workers, tend to be employed within organisations in which they are bound by policies and rules. An influential analysis of the relationship between social workers and the organisations within which they work has argued that there has been a proliferation of managerial organisational rules and that these have eliminated social workers’ discretion. However, this article argues that, even in rule-saturated organisations, social workers retain significant freedom in their work, and that the ways in which professionals relate to organisational rules is a key dimension of understanding discretion. This article employs Oakeshott’s idea of a dialectic of two attitudes to rules to explore the relationship between organisational rules and professional freedom in adult social work in local authorities. It presents the findings of a qualitative study that explores social workers’ attitudes to the formal organisational rules that structure their practice in an English local authority. The study suggests that, while workers split in how they approach organisations in line with Oakeshott’s approach, these perspectives are not mutually exclusive, but are adapted and changed for reasons of pragmatism and principled commitments.