A large portion of content on the Internet today is delivered to clients from hosting services and distribution networks. In sharing the ‘CDN’ label, it is natural to regard the underlying systems and operations as equivalent, and yet they are vastly different. An understanding of their similarities, their differences, and their motivations, can help not only to explain observations, but also inform opportunities. Cloudflare, for example, serves content on behalf of millions, and yet hosts virtually none of it. The Cloudflare network is among the most, if not the most, connected on the Internet, and uses anycast at scales that can defy understanding. In this talk I will cover some of the aspects of Cloudflare and its architecture that shape operations, some that are unique among content services. We’ll get hints of the interactions between business decisions and technological innovation in ways that, just maybe, help open avenues of investigation in the research community.