In dryland pastoral environments, political and geographical marginalization has historically led to development strategies that poorly account for individual and communities’ spatial and socio-economic realities. These development legacies, including long-standing epistemic biases in defining what should be adapted, are often insufficiently considered within adaptation research and practice. This article sets out to analyze the historical emergence and enactment of formal education as a contested adaptation pathway in southern Kenya. For this, I combine the strengths of the historically situated analyses of the pathways scholarship and feminist political ecology’s attention to the performance of intersectional relations of power in everyday livelihood practices. I bring together both archival data and qualitative primary data from focus group discussions (n = 16) and individual interviews (n = 122) conducted in three pastoral communities. The results exemplify the ways that non-climatic factors, such as increased formal school enrolment, (re)shape everyday livelihood practices and social aspirations, molding the current adaptation space. Notably, enacting formal education as an adaptation pathway requires one to navigate increasing cash pressures, mobility, and labor constraints. Wealth disparities, gendered norms, and geographies intersect to shape patterns of vulnerability, with poorer pastoralists residing further away from school centers facing difficult trade-offs on their time and resources. Understanding pathways enactments contributes to problematizing current logics of development and adaptation needs, while yielding important information on socio-spatial differentiation processes in pastoral systems. It also opens the space for further research to use these critical insights to identify alternative adaptation pathways that support more just transformations towards sustainability.