This chapter goes back to the arguments about the importance of context for design-oriented research on women’s work. It addresses questions such as: What are the most relevant aspects of context, how much do designers need to know about them, and what are the methods that can help them understand and deal with contextual elements in their work? The chapter revisits concepts that help understand contexts and their epistemological roots and discusses approaches to dealing with context in practical terms: learning about the history of a place and its culture; understanding politics, policymaking, and the institutional/organizational context; getting a hold on working conditions and skills; making space for intersectionality. The chapter includes a retrospective analysis of two of the authors’ own design/research projects, looking into how they dealt with context. It formulates a set of questions intended to help designers develop strategies that will maintain a sensitivity towards gender issues.