The history of anonymous communications on the Internet dates back to the early 80's but since then there have been dramatic changes in how anonymous communication systems have been built and how they have been used. In this talk I will describe some of these key changes, and what has motivated them. These include the web taking over from email as the major means of communications, and users of anonymous communication systems prioritising censorship-resistance over privacy. The growing popularity of anonymous communication systems has also led to commercial and political realities effecting how projects are run and software is designed. In particular, I will discuss how the Tor software has changed, and the Tor project evolved in this environment. I will conclude by summarising what might be the future for anonymous communication systems and how they may have to adapt themselves to changing circumstances.