Gender mainstreaming (GM) is a strategy used by governments to promote gender equality. It entails integrating gender and intersectional considerations into all aspects of policy work, including policy formulation, implementation, and evaluation. However, its success in achieving gender equality and social transformation has been limited. Drawing on implementation research and narrative analysis, this article explores the micro-level dynamics and the local actors that help shape the character and outcome of gender mainstreaming. Using narrative analysis, we explore how GM specialists within the Canadian public service make sense of their role, and we identify the strategies they use to make gender matter in policy work. By examining their stories of isolation, disempowerment, and resistance, we uncover the administrative and political forces that shape not only the “space” for gender work but also the opportunities for individual activism and resistance. These stories convey how, by engaging in these micro-level strategies, GM specialists both challenge and reinscribe, at the macro level, technocratic representations of GM and of policy work in general. We conclude with some reflections on the insights that micro-level analysis and implementation research can bring to the study of gender mainstreaming.