In many places around the world, the continuing expansion of agricultural land into forested areas is a context which urgently needs transformative change towards more sustainable pathways. Defining and implementing such transformations requires critical reflection to avoid reproducing business-as-usual practices. Transformative alternatives need to be capable of challenging detrimental power structures underlying social injustices and environmental degradation. Implementing such alternatives therefore needs a deeper and plural understanding of the historical processes underpinning the interrelation between social and environmental dynamics. In this paper we focus on the northeastern Nicaraguan agricultural frontier to analyze the historical emergence and consequences of a dominant cattle-based territorial pathway and to unveil local actors’ practices and perspectives on possible transformative change. We thereby aim to enrich the debates on Transformations to Sustainability and the identification of alternatives capable of challenging hegemonic dynamics. Our methodological contribution lies in adopting an original mixed-methods strategy based on the joint use of agrarian diagnoses and Q-method. First, our results provide an in-depth understanding of the historical evolution of agricultural practices and processes of social differentiation, and how these processes relate to techno-economic conditions influencing farmers' strategies. Second, we identify four perspectives within a specific network of actors regarding the processes of social-environmental change and analyze the perceived opportunities and limitations of actual and imagined alternatives. Based on these insights, we show that certain alignment of practices and motivations generally reinforces the dominant cattle-based territorial pathway. We also indicate that the most commonly promoted alternative strategies (often by external organizations) tend to reinforce the incumbent pathway rather than addressing the related social and environmental concerns. Yet, we also identified a subaltern niche of perspectives and practices from which a bottom-up actor coalition could emerge, addressing power imbalances and re-assembling ideas and practices towards transformative change.