From the prospective traveler surfing the web for cheap vacations to executives analyzing market trends with a data warehouse, at home and at work, people are confronted with increasingly richer information environments. This study is an attempt at modeling the behavior over time of the “information consumer” (web surfer or executive) in such environments. The objective is to gain a better understanding of how to design the technologies that support and enhance the interaction with these information environments. Two key design variables for information environments are examined: content quality and structural quality. Drawing on research in human-computer interaction and ecological psychology, a behavioral model is developed in which it is postulated that the importance of structural quality will diminish with time, whereas content quality will increaseinimportance. Atwo-stagemethodologyisemployedwhichcombinesalongitudinalexperimentwith a cross-sectional survey. Both the survey and experiment are conducted in the context of informational websites. The experiment provided 178 undergraduates with repeated exposure over several weeks to eight custom-built websites, manipulated to vary in content quality and structural quality for which their preferences (and associated rationales) were elicited at three time points over the course of the experiment. Additionally, 163 of the undergraduates also completed a survey providing data about the effect of content and structure on usage behavior for sites for which they had mature experience. Preliminary results of the experimental data support the hypotheses. The research has potentially significant implications for the design of information environments.