Amid the web series boom, a few programs—The Guild, Lonelygirl15, Dorm Life, What the Buck, Fred—have been able to achieve popularity by marshalling zealous fan bases. Experts in online serials—editors of blogs, directors, producers—agree that making a “connection” with viewers is the key to success. Viewer engagement has always been important in media, but new media has made this aspect of serialized production more pronounced, they claim. When Todd Gitlin wrote Inside Prime Time, he described a world where TV network executives had little clue what the audience wanted or who they were. Online, the consensus now seems to be, the producers should know. But what does connection look like? How and why is it created and sustained? This paper seeks to use the rise of the web series and the discourse around its production and distribution to answer these critical questions.