This article reflects the confluence of two contradictory streams of thought regarding language theory and knowledge organization. While linguists, philosophers, and cognitive scientists have turned away from structuralism and the notion of determinacy, knowledge engineers and specialists in information technology have embraced the semantic/semiotic triangle in their efforts to model information and knowledge for use in computerized environments, particularly to support the Semantic Web. The discussion begins with a view of traditional terminological concept systems and goes on to analyze a full range of knowledge representation resources, examining each with a view to its potential for distortion as a result of inherent indeterminacy. Crosswalks and interoperability play a role in linking critical resources.