A comparative case study design is used to investigate the online strategies of five Iowa newspapers, including Web content, policy, and how the company evaluates success. The influence of the organization on strategy and Web model is also considered. The corporate structure of the cases ranges from a rural privately held weekly (circulation 4,212) to a regional employee-owned daily (circulation 64,062), to a statewide, chain-owned daily (circulation 154,268). Findings indicate that the newspapers investigated are transitioning from the early stages of online news delivery to more formal tactics regarding their online presence with early integration of the online product into company policy and newsroom practices. Multiple business models are in development, while newsrooms struggle with added demands for Web-specific content placed on current staff, stagnant personnel resources, and ethical ambiguities when dealing with online reader feedback. These general themes are discussed in the context of organizational and technological change.