Teaching and education are processes of communication. Educational theory is concerned with the communication process itself as well as with the cognitive changes brought about by this process. By far the greatest part of this communication is conveyed through speech and writing. Here we take the term “written language” to include mathematical, technical and similar symbols, also drawings and diagrams. In this chapter, the measurement of the information in written language is emphasized for two reasons: A) The transmission of information via printed texts plays a large part in teaching, study and education. Textbooks, handbooks, sourcebooks and reference works are used for this purpose. Today, on an increasing scale, programmed teaching texts are being introduced with the aim of making teaching objective. Besides instruction in reading, the traditional cultural skill—and for our purposes reading is the ability to code phonetic symbols into written symbols and vice versa—there is also instruction in the symbolic languages of mathematics, the natural sciences, technology and other areas of life. The application of information theory to written language opens up a defined and bounded set of pedagogical problems. B) At present there are still difficulties in attempting a differentiated and direct analysis of the written language by information theory. However, it is feasible to transcribe into written language the verbal communications which occur in the course of educational processes. Compared with direct communication, transcribed speech represents a loss, since it cannot express that part of the information flow between teacher and student which is conveyed by intonation, emphasis, and dynamics, or by gestures and mime. Nevertheless, a large proportion of the information survives transcription. Thus, teaching protocols can be used in the science of education for the analysis of instructional strategies, processes, and situations. If we can apply information theory to the study of written language, we can also gain indirect access to spoken communication via transcription.