Using case studies from the Web site redesigns of The Museum of Modern Art, New York (MoMA), the National Gallery of Art, Washington, DC (NGA), the National Gallery, London, and the San Francisco Museum of Modern Art (SFMOMA), this paper considers the changing role of museum Web sites, outlines the goals of the respective projects, compares and contrasts the different approaches taken, and presents valuable insights from the four institutions.As of publication, the museums represent the different cycles of a Web site redesign initiative: NGA is in the discovery and strategy phase, the National Gallery and MoMA are in the development stage, and the new SFMOMA site is live. Together the authors of this paper explore the shared challenges we faced in planning, developing, and deploying new and improved Web sites, and present some of the valuable, and painful, lessons learned.These lessons