Studies of repair and maintenance work have pointed to a gap between the way repair and maintenance work is prescribed and the way it is done in practice. This article seeks to contribute an empirical and conceptual account of what transpires in this gap. It focuses on repair and maintenance team supervisors who are both trained repair workers and managers. The article argues that supervisors use their knowledge of the organization alongside their knowledge of materials, people, and objects. To do their work, they articulate and negotiate competing interests and values, drawing on their experience as repair workers and on their managerial autonomy. In developing the concept of “working knowledge,” existing studies have tended to focus on the triangular relationship between customers, repair workers, and machines. This article contributes another dimension to “working knowledge,” arguing that supervisors and repair workers strive to unpack and interpret, to the best of their ability, not only what constitutes a breakdown or a repair but also what is desirable and beneficial for the organization. By closely tracing three cases in which team supervisors engage in organizational work and interpret managerial preferences, the article shows that repair and maintenance work is shaped not only from below, by interactions with materials, environments, and people, but also from above, by repeated attempts to order, organize, and manage it.