The Sustainability Window -analysis is a method to evaluate the drivers and driven variables of sustainability. Sustainability Window is an analysis tool for assessing the sustainability of development simultaneously in all of its three pillars: environmental, economic, and social. The SW analysis method provides information of the maximum and minimum economic development that is required to maintain the direction of social and environmental development towards more sustainable targets. With the Sustainability Window method, it is possible to easily analyse the sustainability using different indicators and different time periods making comparative analyses easy. The new method makes it also possible to analyse the dynamics of the sustainability and the changes over time in the width of the window. This study provides a comparative Sustainability Window analysis of the eight ASEAN countries. Thus, the study covers eight ASEAN countries in the time frame of 2010-2016 except Singapore and Brunei. The data of the study is the database of the Sustainable Society Index (SSI) database, which provides comprehensive data set for key dimensions of sustainability. This study reveals key challenges and successful developments of sustainable development in eight ASEAN -countries. The study reports all key results in the terms of strong and weak sustainability. The results can be used in the formulation of strategic sustainability policies in the ASEAN country group. Probably the ASEAN countries can learn more from their experiences in the formulation of sustainability policies. This study can be seen as a part of such mutual learning process among the ASEAN countries.