The global society is becoming a reality. Inevitably this leads onto questions around the generation and exploitation of knowledge. Education systems grow to be more complex and interdependent. The Web makes a large number of learning resources within reach of anyone with Internet access. However, many valuable resources are difficult to use due to the lack of interoperability among various education systems. In this chapter, the fundamental principles of interoperability of complex and dynamic global education system are presented. The contemporary approaches to systems theory, entropy and autopoietic theory, social system theory, sociocybernetics, the strengths and limitations of these approaches, and their potential applications in education are examined. The nature of educational systems can be linked to biological concepts. When education principles and cybernetics are combined, the resulting theory turns on scientific principles instead of philosophical speculations. Proper utilization of such principles provides methodology that increases the effectiveness of web-based education systems.