This paper presents a new paradigm for information theory which is a synthesis of Barwise-Seligman’s qualitative theory and Shannon’s quantitative theory. The new paradigm is best viewed as a meta-theory for Shannon information theories and allows different probability theories, and subsequently, new Shannon information theories, to work within a common framework. The resulting Shannon theories conform to a qualitative structure and decorate it with measures of information. This approach is useful for analyzing assurance problems where there the analysis must contend with incomplete and even contradictory information. In particular, the mathematical constructs of the theory allow one to use just about any logic which admits a companion measure theory. Keywords Barwise-Seligman Information Theory, Shannon Information Theory