This paper attempts to identify paths by which women can break the political glass ceiling of executive power in Asia. In doing so, it aims to answer the following question: Which conditions have been necessary and/or sufficient for women to break the political glass ceiling in Asia since 1998? This paper evaluates existing theories on women’s participation in executive power by applying those theories to Asia through qualitative comparative analysis (QCA). Overall, we find that there are three alternative paths to office and two different configurations that keep women away from office. Conditions that were previously necessary, such as liberal regimes or family ties to political dynasties, are no longer necessary, but, in combination with new conditions, they are still helping some women to reach office. Women in non-democratic regimes with no family ties to political dynasties are now reaching the highest positions of government as a result of specific personal and political junctures.