Entrepreneurship has gained increasing attention as a strategic area for rural development. Addressing environmental, demographic, and gender inequality challenges in rural areas requires contextualizing entrepreneurship. Moreover, applying contextualization as a critical lens provides a deeper understanding of how and why entrepreneurship happens in rural areas. This thesis examines the interplay between entrepreneurship and gender within the rural context and is situated in the growing body of literature expanding the knowledge on entrepreneurship in rural contexts. Thus, the thesis responds to the calls to contextualize rural entrepreneurship (McElwee & Atherton, 2021) and gender in entrepreneurship (Welter, 2011; Baker & Welter, 2020; Welter 2020). The thesis is based on a qualitative study on the life stories of women and men entrepreneurs engaged in their family businesses in the rural province of Småland in southern Sweden. The thesis further contributes with a systematic literature review describing the “state of the art” in rural entrepreneurship as well as the intertwinement between the rural, gender, and entrepreneurship fields. Methodologically, the thesis contributes to the operationalization of a rural proofing concept. To theorize on the intersection of these three, often separately studied, fields (Webster 2017), the thesis illustrates the dyadic influence of the rural context on entrepreneurship and gender relations. The thesis also provides theoretical contributions concerning the interdependence of the rural context, agency, and entrepreneurship, including the implications of this interdependence for policymakers, and practitioners. Contextualizing rural entrepreneurship and gender in entrepreneurship is crucial in the development of policies able to address the needs and capabilities of rural entrepreneurs to explore the impact of different policies on rural enterprise development (Smith & McElwee, 2014). Rural proofing policies that take into account the particularities of the rural milieu, such as gender, ethnicity, and traditions within the rural community, can increase the resilience of rural enterprises in the face of challenges arising from local and global contexts.