For decades, proponents of the Internet have promised that it would one day provide a seamless way for everyone in the world to communicate with each other, without introducing new boundaries, gatekeepers, or power structures. What happened? This article explores the system-level characteristics of a key design feature of the Internet that helped it to achieve widespread adoption, as well as the system-level implications of certain patterns of use that have emerged over the years as a result of that feature. Such patterns include the system-level acceptance of particular authorities, mechanisms that promote and enforce the concentration of power, and network effects that implicitly penalize those who do not comply with decisions taken by privileged actors. We provide examples of these patterns and offer some key observations, toward the development of a general theory of why they emerged despite our best efforts, and we conclude with some suggestions on how we might mitigate the worst outcomes and avoid similar experiences in the future.