In-forest drying of roundwood and biomass (residues) can result in more efficient transport operations from an economical and environmental perspective. On the negative side, in-forest drying may result in dry matter losses (DML), impacting the quantity and quality of residues delivered to energy plants. This paper investigated the impact of roundwood and residues in-forest drying and DML on supply chain costs and Greenhouse Gas (GHG) emissions. For the assessment, a short-term optimization planning tool was applied to a supply chain located in Asturias, Spain, consisting of fourteen supply points and two demand points: A pulp mill (demanding roundwood) and a power plant (demanding residues). Four scenarios were included in the analysis comprising different combinations of DML for roundwood and residues resulting from in-forest drying. Our results indicate that in scenarios that include in-forest drying and DML, the negative economic effects are offset by the substantial reductions in transport costs and GHG emissions. In-forest drying of roundwood and residues without DML can result in a 6.5% reduction in supply chain costs, 14.9% fewer truckloads to destination points, and 18.1% less fuel consumption and GHG emissions.