The turnarounds from decrease to expansion in forest areas that took place during the last century have been examined through the lens of forest transition theory (FTT). Among temperate and Mediterranean European countries that have seen an expansion of forest cover, Portugal stands out as the only case in which this trend has recently been reverted. In this study, we explicitly map and document the forest transition (FT) in the country over the period 1907–2006, and investigate when and where forest transition happened de facto, and which were the land use transition pathways that resulted from the shrublands, agriculture, and forest interplay dynamics. After thematic and geometric harmonization of land cover maps from 1907, 1955, 1970, 1990, and 2006, a cluster analysis established four typologies, and a transition matrix was constructed to assess land cover dynamics. We found that up to 1955, FT occurred simultaneously with agricultural expansion, as shrubland areas diminished. Afterwards, with the retraction of agricultural area and the consequential decoupling of forest management from local actors, FT gained momentum and expanded up to the 1990s. While during the first half of the 20th century, forest expansion followed the “Scarcity” and “State Policy” pathways fostered by local socio-ecological feedback loops, throughout the second half of the century forest transition was driven by exogenous socio-economic forces, following “Economic Development” and “Globalization” pathways. We show how, despite these forces, FT can be derailed by endogenous factors such as wildfires, which limited and in some areas even reverted the afforestation process, initiating a deforestation phase. Since the necessary conditions for FT (technology shift, urbanization, agriculture retraction and public afforestation programs) were available in mainland Portugal, we advance the hypothesis that critical wildfire risk governance deficits may have been responsible for arresting FT. Considering the critical role of forests and other wooded areas in supporting climate change mitigation and sustainable development, our work provides useful evidence and insights for public decision makers on previously unaddressed dimensions of FTT.