This dissertation is an investigation of the gendered dynamics of sustainable agriculture practiced by women operating commercial-scale, sustainable farms in Jaffna, Sri Lanka, with a focus on women's agency and freedoms within the agricultural sector. Women operate 26% of farms in Jaffna, yet women are notably absent from agricultural development policies. As climate change threatens the livelihoods and security of farmers in Jaffna, establishing data on the opportunities, barriers, and experiences of women as farmers is crucial for developing an accurate contextual understanding necessary to inform effective policies that ensure sustained food production and livelihood security. Using the capabilities approach as a conceptual framework and 50 individual interviews of with women farm operators in 2021, during COVID, this research examines the socio-cultural, economic, and policy-driven barriers that constrain women's agency and freedoms as primary farm operators. The study identifies a duality in women's experiences: while they demonstrate remarkable agency in sustainable agricultural practices within their farms, they face significant systemic barriers in engaging with external economic systems. A central insight of the research is the contrasting roles played by middle operators, who exploit women’s dependency to access external markets, and cooperatives, which serve as transformative bridges by fostering collective empowerment and expanding women's capabilities across both spheres. The study further highlights the innovative localized strategies women employ to adapt to climate vulnerabilities and systemic constraints. By blending traditional ecological knowledge with modern agricultural technologies, women have developed integrated farm management systems that optimize productivity, enhance biodiversity, and build resilience to environmental shocks. These findings challenge the conventional image of farmers as solely men battling nature and instead position women as central agents of ecological stewardship and sustainability.