Forest management is a complex topic at the interface between sustainability and the resilience of socioeconomic and environmental systems. The influence of market forces, supranational, country and regional policies, as well as climate change, on forest goods and services, is expected to increase in the near future. Such a complex interplay between economic and environmental forces is common to most European countries. The aim of this study is to operationally delineate and discuss the transition of the environmental sustainability and economic viability of forestry in Italy. This country encompasses the typical Mediterranean ecosystems with broad forest coverage in mountainous and hilly areas, where expanding woodland areas have been observed in the last decades mainly as a consequence of the decline of agropastoral activities, especially in disadvantaged and marginal areas. The consequent increase in wood biomass was frequently conceived as an element of environmental criticality, exposing woods to high vulnerability to wildfires and a consequent reduction in their economic value, possibly exacerbated by local warming. These dynamics usually took place in contexts where only a part of the overall forest heritage was subjected to regular management, despite the efforts made through various policies such as the Constitutional Law 3/2001 and the recent Law on Forests and Forestry Supply Chains. The latter policy tool, enhancing the concept of “active forest management” aimed to establish a sustainable approach to forest resources, leading to a broader forest area for formal planning and controlled harvesting. These dynamics took place in parallel with the inherent expansion in forest certification schemes formally promoting long-term environmental sustainability and a wider spectrum of forest ecosystems. Timber and non-wood materials and products are key elements from the perspective of achieving sustainable (climate-neutral) development in advanced economies.