The Dublin Core "1:1 Principle" asserts that "related but conceptually different entities, for example a painting and a digital image of the painting, are described by separate metadata records" (Woodley et al., 2005). While this seems to be a simple requirement, studies of metadata quality have found that cultural heritage metadata frequently does not conform to the "Principle." Instead, representations commonly appear to make statements about multiple related resources, such as a painting and a digital surrogate that depicts the painting. Although these "violations" of the "Principle" are assumed to reduce metadata quality, they are widespread in cultural heritage metadata, and metadata creators indicate "a great deal of confusion" about what the "Principle" means and what constitutes a violation (Park & Childress, 2009). A conceptual analysis of the "1:1 Principle" reveals that it is the product of an encounter between two different paradigms, with distinct approaches to how descriptions function, that have dominated the development of Dublin Core. The "knowledge organization (KO) paradigm" draws from a century of practice developing bibliographic representations and rules for description in libraries, archives, and museums (LAMs). This paradigm is primarily concerned with the organization and classification of document surrogates. It does not provide a formal account of how bibliographic languages describe and reference the resources they represent. In contrast, the "knowledge representation (KR) paradigm" is influenced by recent computer science, linguistics, and philosophy. This paradigm is primarily concerned with supporting automatic inference and data integration, mobilizing formal semantic theories to provide descriptions with grammatical structures that can be computationally modeled. It provides an explicit and formal, although not untroubled, account of reference and description. Further analysis of how discussion of the "1:1 Principle" has been shaped by these two different approaches to description shows that "1:1 Principle" problems are as much about the design and function of representation languages as they are about errors made by metadata creators. The "Principle" is most directly derived from the formal theories of description and reference that use proper names (or identifiers like URIs) to refer directly to resources. Bibliographic records with fixed syntaxes, but informal, colloquial semantics, can successfully communicate descriptions that are meaningful to human interpreters and enable syntactic interoperability between systems. However, when viewed through the lens of formal semantics, bibliographic representations may appear incoherent--as failing to unambiguously reference any resource, or provide a single, shared semantic interpretation of descriptions. These problems are exacerbated by the need to make subtle ontological choices about descriptions of resources involved in equivalent, derivative, or descriptive relationships. Because knowledge organization representations rely on relatively informal semantics, often not more than a sentence or two of natural-language prose, the heuristics for identifying "1:1 Principle" violations depend heavily on the implicit and informal, shared conceptual framework of cultural heritage professionals. A formal interpretation of these heuristics, therefore, requires more than operational definitions of the "Principle"; it requires highly expressive ontologies that make that understanding logically explicit. Moreover, even formalizing traditional ontological distinctions will fail to identify violations when contingent historical facts play a role in interpretations of metadata records. While these difficulties make fully reliable methods for automatic detection of "1:1 Principle" violations impossible in principle, they usefully reveal obstacles that will require attention as the cultural heritage community moves towards adopting more formal representation practices that are the basis of the Semantic Web and Linked Data. Recognition of the fundamental differences between the knowledge organization paradigm and the knowledge representation paradigm can lay the groundwork for reconceptualizing how we represent related resources. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]