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This article examines the relationship between environmental and cognitive structure. One of the key tasks for any agent interacting in the real world is the management of uncertainty; because of this the cognitive structures which interact with real environments, such as would be used in navigation, must effectively cope with the uncertainty inherent in a constantly changing world. Despite this uncertainty, however, real environments usually afford structure that can be effectively exploited by organisms. The article examines environmental characteristics and structures that enable humans to survive and thrive in a wide range of real environments. The relationship between these characteristics and structures, uncertainty, and cognitive structure is explored in the context of PLAN, a proposed model of human cognitive mapping, and R-PLAN, a version of PLAN that has been instantiated on an actual mobile robot. An examination of these models helps to provide insight into environmental characteristics which impact human performance on tasks which require interaction with the world. Copyright 1999 International Society for Adaptive Behavior.