Currently, most of the Web is designed from the viewpoint of helping people who know what they want but need help accomplishing it. User goals may range from buying a new computer to making vacation plans. Yet, these are simple tasks that can be accomplished with a linear sequence of events. With information-rich sites, the linear sequence breaks down, and a straightforward process to provide users with information in a useful format does not exist. Users come to information-rich sites with complex problems they want to solve. Reaching a solution requires meeting goals and subgoals by finding the proper information. Complex problems are often ill-structured; realistically, the complete sequence can’t even be defined because of users’ tendencies to jump around within the data and to abandon the sequence at varying points (Klein, 1999). To reach the answer, people need the information properly positioned within the situation context (Albers, 2003; Mirel, 2003a). System support for such problems requires users to be given properly integrated information that will assist in problem solving and decision making. Complex problems normally involve high-level reasoning and open-ended problem solving. Consequently, designer expectations of stable requirements and the ability to perform an exhaustive task analysis fall short of reality (Rouse & Valusek, 1993). While conventional task analysis works for well-defined domains, it fails for the ill-structured domains of information-rich sites (Albers, 2004). Instead of exhaustive task analysis, the designer must shift to an analysis focused on providing a clear understanding of the situation from the user’s point of view and the user’s goals and information needs.