This paper addresses one of the fundamental problems of the philosophy of information: How does semantic information emerge within the underlying dynamics of the world?—the dynamical semantic information problem. It suggests that the canonical approach to semantic information that defines data before meaning and meaning before use is inadequate for pre-cognitive information media. Instead, we should follow a pragmatic approach to information where one defines the notion of information system as a special kind of purposeful system emerging within the underlying dynamics of the world and define semantic information as the currency of the system. In this way, systems operating with semantic information can be viewed as patterns in the dynamics—semantic information is a dynamical system phenomenon of highly organized systems. In the simplest information systems, the syntax, semantics, and pragmatics of the information medium are co-defined. It proposes a new more general theory of information semantics that focuses on the interface role of the information states in the information system—the interface theory of meaning. Finally, with the new framework, it addresses the debate between weakly semantic and strongly semantic accounts of information, siding with the strongly semantic view because the pragmatic account developed here is a better generalization of it.