The success of the Republic of Estonia in the Program for International Student Assessment (PISA) was a surprise both nationally and internationally and has led to several important questions. What are the reasons for these results? Which historical developments and recent decisions have allowed a small and not particularly rich country to build an education system that offers cutting-edge knowledge and skills in both the European and global contexts? This study attempts to answer those questions by distilling insights into the Estonian learning system. First, the authors outline key qualities of the system that may have impacted the PISA results; next, they analyze six different parts of the system (goals, standards, curriculum, assessment, teachers, governance, and equity) providing a more detailed picture of Estonian education; finally, the report discusses the current challenges of the Estonian learning system, mapping the debates about future options and possible changes to teaching and learning practices. The report reflects the opinions and understanding of the authors, but the proposed key qualities of the Estonian learning system (see Figure 1 on the next page) were determined through a series of conversations among top educators across the country, as well as scientific analysis and research evidence.