Forestry as an important industry has both direct as well as indirect effects on the Estonian economy. It is therefore essential that it is sustainably managed so that it can continue to contribute to the economy in the future. The first aim of this article is to establish the situation regarding felling and regeneration in Estonia. As the available forestry statistics display discrepancies and lack consistency, it was as a necessary first step to gather information about and analyze the validity and reliability of the prime data to make the data sets useful for comparison over time and establish the current trends in Estonian forestry. However, with the help of interviews we are able to show that economic instability in Estonia brings with it increased logging rates and hinders investments into regeneration and maintenance. The problems are particularly pronounced in private forestry. Second, the article seeks to explain the socioeconomic reasons behind this situation. Economic problems among private owners, a liberal forestry policy, together with rapid land reform and weak enforcement of forestry legislation are some of the reasons that can explain the forestry trends in Estonia.