Ensuring local and sustainable food security is gaining an important role in rural development strategies at national and regional scales in Europe. This relies to an important degree upon the implementation of new, or old, agri-environmental policy, namely, policies at the intersection of agriculture and the environment. Yet, the incorporation of agri-environmental policy in rural development strategies at the regional level creates, and often accelerates, contradictions between existing rural development paths and the structural changes needed to achieve both environmental objectives and economically viable agricultural development. Within this context, agroecological transitions are framed as key for transformations of national food systems. However, understanding the prospects and barriers for agroecological transitions and food security at the regional level requires a much deeper understanding of how national and international food policies shape and are shaped by long political economic trajectories of rural development with competing interests. In this paper, we explore these contradictions of rural development in Europe by comparatively analyzing the political nature of potential agroecological transitions in Europe and how these transitions interact with agri-environmental policies and rural development strategies at the regional level.