We present an approach to combining three areas of research which we claim are all based on information theory: knowledge representation in Artificial Intelligence and Cognitive Science using prototypes, plans, or schemata; formal semantics in natural language, especially the semantics of the `if-then' conditional construct; and the logic of subjunctive conditionals first developed using a possible worlds semantics by Stalnaker and Lewis. The basic premise of the paper is that both schema-based inference and the semantics of conditionals are based on Dretske's notion of information flow and Barwise and Perry's notion of a constraint in situation semantics. That is, the connection between antecedent A and consequent B of a conditional `if A were the case then B would be the case' is an informational relation holding with respect to a pragmatically determined utterance situation. The bridge between AI and conditional logic is that a prototype or planning schema repres...