This paper examines the policymaking process and contents of the two major social security policies of Taiwan in the 1990s. The National Health Insurance (NHI), which was introduced in 1995, was a mixture of success and failure. While it brought about universal health insurance, part of the original objective of creating a comprehensive welfare system through the NHI initiative was not realized. The attempt to introduce a National Pension Program (NPP) in 2000 went through dramatic turns in both policy contents and the prospects for implementation. Though it was originally designed as a modified form of social insurance, a general tax revenue‐funded defined‐benefit scheme was added as an alternative when a new government came into power. The bill, however, was withdrawn before the actual deliberations began. The author argues that policy legacies and actors, and the interactions of these variables within different policy phases, determined the policy contents and changes.