This article describes the outcomes of research that examined the practice of web information architecture (IA) in large organizations. Using a grounded theory approach, seven large organizations were investigated and the data were analyzed for emerging themes and concepts. The research finds that the practice of web IA is characterized by unpredictability, multiple perspectives, and a need for responsiveness, agility, and negotiation. This article claims that web IA occurs in a complex environment and has emergent, self-organizing properties. There is value in examining the practice as a complex adaptive system. Using this metaphor, a pre-determined, structured methodology that delivers a documented, enduring, information design for the web is found inadequate – dominant and traditional thinking and practice in the organization of information are challenged.