Load safety is a critical component of successful logistic operations. Different influencing factors can affect the necessity of intensive load securing methods. The most dominant factor is the friction characteristics of the intended cargo. A cargo with special requirements on load safety is debarked roundwood. Due to modern forestry challenges, larger amounts of debarked roundwood assortments are now being produced within German forest operations. To assess the influence of debarking onto the static and sliding frictions of Norway spruce, pulling tests were performed and compared to barked assortments. Results showed that a significant difference in both static and sliding frictions exists between barked and debarked assortments within the first seven days after harvesting. However, this significant difference became less prominent after the logs continued to dry out and no difference was detected after 21 days. Over the monitored period, debarked assortments presented a 40%–45% faster drying rate than barked assortments. This resulted in a calculated 11%–28% additional transportable net load (m3) of debarked roundwood assortments for long trailer systems. Hence, debarked roundwood can be treated similarly to barked roundwood if stored long enough prior to road transportation, while having the potential of increased savings within the wood logistic chain.