Similarly to other European mountain areas, in Serra da Estrela the grazing pressure has been reducing due to social and economic drivers that have pushed shepherds and sheep to the foothill, or plainly out of the sector. Shrub encroachment on commons and other previously grazed land is one of the most tangible effects of pastoral abandonment in Serra de Estrela. The impacts of the resulting increase in landscape continuity and biomass availability were made clear in the severe fires of 2017 and 2022. As fire risk is likely to increase with climate change, it becomes urgent to understand what strategies can be deployed to keep fragmentation in these landscapes. Key actors such as shepherds should be involved in this discussion to understand their perceptions, points of view and reasons for abandoning upland pastures. In this study, we use fuzzy cognitive mapping to identify the key variables and mechanisms affecting the pastoral system according to local shepherds. In our study, we developed with local stakeholders a framework outlining the local pastoral system. Based on that, we carried out the fuzzy cognitive mapping collecting 14 questionnaires. We found that shepherds' income is a central issue, but that it is highly dependent on many factors. Increasing the Common Agricultural Policy payments alone is not enough to incentivise the use of upland pastures. More targeted strategies, such as more support for shrub clearing, and direct payments conditional to transhumance are more impactful. Despite a contentious discourse between conservation and shepherding values in Serra da Estrela, we find that shepherd's values are aligned with biodiversity conservation and a potential nature-based solution for minimizing fire risk through woody fuel management. This opens up possibilities for new governance strategies, that put Serra da Estrela's social, environmental and cultural values at its core.