High Nature Value (HNV) farmlands currently retain most of the biodiversity associated with agricultural landscapes in Europe. In a time of globalized food systems, the social-ecological conditions to maintain these low-intensity and thus less productive HNV farming systems are difficult to meet. Halting the loss of HNV farmland requires fostering the socioeconomic viability of HNV farming systems that is compatible with social, cultural, and ecological values. Pursuing such viability calls for tailored actions to steer the development of HNV farming systems based on the strength of their local assets. Such a transformational learning process involves changing the territorial dynamic towards better integration of biodiversity at several levels of management (from farm to territorial level). Based on the description and analysis of ten HNV territories distributed across Europe, we explore how HNV innovation brokers can strategically engage with local actors to preserve the environmental characteristics of HNV farmland areas while improving their socioeconomic viability. The aim of this research is to improve the understanding of the range of approaches and strategies of innovation brokers to meet the challenges of HNV farmland conservation. The study analyzes the different innovation processes that took place in each area, concentrating on the engagement phase. Our results demonstrate that HNV farming situations across Europe are quite diverse from an agroecological and socioeconomic point of view. There are distinct conservation challenges and associated risks for each HNV farming context. The need for a strategic approach to HNV conservation at landscape-territory level is discussed. The key role of innovation brokers is highlighted, together with the need for a strategic approach to innovation brokerage, which is explicit in relation to territorial needs and the changes required. We demonstrate the importance of the landscape-territorial vision as an entry point for shaping HNV farming systems towards socially desirable scenarios.