Topic maps provide exciting opportunities not just to make information easier to find, but to increase the usability of software. In order to provide users with the information that applies to their particular situations, in forms that they can use, software must be aware of a user’s context (in a broad, multi-dimensional sense). Topic maps can serve as the language for linking information to software applications and for sharing information about context among applications. Using topic maps in the design of user-centered software applications for the U.S. Social Security Administration, we have encountered several interesting issues that are not necessarily found in the design of stand-alone information resources. In the future, there is an increasing potential role for topic maps in the design of flexible applications. The infrastructural investments required to achieve richly contextual applications can be made gradually, over the course of many small and successful projects, as the role and benefits of Topic Maps becomes increasingly visible.