This chapter explores the common history shared by semiotics and educational theory. By looking at some of the major moments in the history of semiotics, the chapter elucidates the co-evolution of education and semiotics. The entanglement of education and semiotics, due to their common roots in the hermeneutics of medieval mystical theology, later effectuated some anthropological and ecological bearings that edusemiotics takes into consideration. If we, humans, are the interpreters of the world, we can co-create, "read' and "write' the semiotic reality, the reality of signs, both linguistic and extralinguistic. The chapter critically examines some important texts in the history of philosophy from the perspective of semiotics and in view of the relational dynamics between man and cosmos and their co-evolution. Reading and interpreting the texts by St. Augustine, Ibn Arabi and others elucidates the holistic approach to educational philosophy in conjunction with metaphysics. The chapter contrasts the rich semiotic legacy through history with the non-semiotic dualist philosophy of modernity that oriented education toward utilitarian curriculum thus dismissing the relevance of the body and material environment for the learning process. The chapter stresses the ecological bearing of edusemiotics and considers its present position as a proper continuation of the medieval liberal education project while also acknowledging the importance of contemporary research across biosemiotics and edusemiotics.