More than ten years of experience with the web has allowed us to understand what the medium does well and what it does poorly, and how we may improve online historical efforts so they capitalize on the web’s strengths while avoiding its weaknesses. This essay explores three possible ways to advance digital history: interaction between historians and their subjects, interoperation of dispersed historical archives, and the analysis of online resources using computational methods. Thinking about such possibilities raises important, age-old questions about how we should preserve and chronicle the past.