This article reports our experiences in developing a work-oriented design practice. We sketch our general approach to relating work practice studies and design, including our use of case-based prototypes. We go on to describe our entry into the law firm that was the setting for this project and our decision to focus our design efforts on two forms of work at the firm. We discuss our experiences in developing a case-based prototype to support the work of document search and retrieval. We then describe our encounters with organizational politics at the firm in the context of a joint exploration of image analysis technologies in relation to the work of litigation support. We conclude with findings on the practices of working with document collections, the value of case-based prototypes, and recommendations for combining work practice studies and design interventions.