The olive trees cultivation and the olive oil production in Portugal are two fundamental agriculture sectors with high economic impact, providing employment and local development, mainly in the interior of Portugal despite they are deprived regions, involve a combination of strategies, including few investments in infrastructure, job creation programmes, access to education and healthcare, and community development initiative. But these activities have always been centred on small farmers, often on a subsistence basis. The olive oil production grows, with high level of investment and the production focus on strong commercial sense, with large, modern, intensive olive groves and highly mechanised production processes. Methodologically, this research deals with two different analyses. The first is the theoretical analysis based on the literature review to contextualise the olive oil sector, in general, and its sustainability, in detail. The second analysis is empirical analysis based on the qualitative and quantitative analysis, with data collected from Portuguese statistical database published by official bodies that enable to understand the challenges of agriculture sustainability in rural areas with focus on the olive oil production. The results of this research show that the agriculture sustainability applied to olive oil in Portugal is based on the stability principle between production, biodiversity, protection of natural and cultural heritage, and social concerns as strategies to promote the accountability that can be highly beneficial.