The last billion people to join the online world, are likely to face at least one of two obstacles: Part I: Rural Internet Access Rural, sparsely populated, areas make conventional infrastructure investments unfeasible: Big corporations attempt to address this challenge via the launch of Low-Earth-Orbiting (LEO) satellite constellations, fleets of high-altitude balloons, and giant solar-powered drones; although these grandiose initiatives hold potential, they are costly and risky. At the same time, small local operators, Wireless Internet Service Providers (WISPs), are growing in numbers, in subscribe base and in territory covered. WISPs can play a major role in serving a growing number of rural communities, as well as offer real competition to incumbent operators in urban and semi-urban markets, leading to better service at reduced costs. The key motivation for this work is to lower the barriers-to-entry for small rural WISPs, and to sustainably grow their operation — this has been my research focus for over 15 years. The core of this work is based on a case-study of a WISP, FurtherReach — which we have built from the ground up. This WISP brings broadband Internet service to hundreds of subscribers at the south coast of Mendocino county in California. Through designing, deploying and operating this venture, we learn about the real challenges faced by WISPs, develop technical solutions as well as business models, operational methodologies and deployment strategies. The FurtherReach case study is presented in chapter 2. Chapter 1 introduces the overall WISP ecosystem. In chapter 3 we discuss the potential of Software Defined Networks (SDN) to aid in WISP operations. Finally, chapter 4 discusses the often overlooked computer-security concerns that are unique to rural communities, especially in developing countries. Part II: Dissent Networking Oppressive regimes censor and restrict information flow. Sadly, Internet censorship, in some countries, does not seem to be going away, and presents a growing challenge. The degree and effectiveness of censorship varies greatly, as does the risk of getting caught circumventing it. Similarly, the technologies to aid dissenters vary accordingly. My work in this field predates smart-phones, which I believe could be made to offer safe and effective solutions even in the most dangerous of countries. Should we consider these technologies Internet access? Once again the degree of connectivity, and especially interactivity, from behind a censoring firewall, varies greatly. In chapter 5, I present our attempt at defining the threats and narrating the exceptionally challenging problem space. I find this chapter quite discouraging as it dictates exceptional restrictions on the design space, yet ignoring these constraints may put users of the technology in greater risks than without it. It makes us question if technology can help at all? I continue in chapter 6, to present Rangzen, our initial attempt at designing a solution that adheres to the strict constraints presented in 5. While limited in functionality, especially given its delay-tolerant approach, which is incompatible with many Internet applications that expect real-time interactivity, it does successfully follow our design guidelines for dissent technologies as presented in chapter 5. We have built an Android app, Rangzen, based on these design specifications, which undergoes a beta testing program at the time of this writing. The app will be distributed freely on the Android store in January 2016, and the code is open source and available to the public.