This article traces the influences of hypertext theory throughout the various genres of online publication in technical communication. It begins with a look back at some of the important concepts and theorists writing about hypertext theory from the post-World War II era, to the early years of the World Wide Web 2.0, and the very differing notions of its potential. A significant challenge during this formative period was the fact that limitations in technology and infrastructure placed limitations on the potential envisioned by these scholars. The ways in which we look at early scholarship differ even a decade or more later, in terms of some of the information technologies and tools we use today. In the Web 2.0 era, we see a trend of blending and extension beyond principles found within hypertext theory in the tools we use and user experiences we create with them.