The main purpose of this research is to analyze and explain of some issues and challenges of Iran’s educational system based on Rule-Following argument in Wittgenstein's later philosophy. This qualitative research utilized a descriptive, analytical, and interpretive method to review the related literature. Based on results, it can be concluded that, according to Rule-Following argument, the root of some of the challenges in Iran’s educational system is creating a gap between school and society and disregarding the needs of each other. Transferring knowledge and information to student's minds and ignoring the teaching of “how to learn” along with ineffectiveness of graduates, the same look at all disciplines regardless of the essential differences between them, lack of opportunity for learners to participate in a form of life, catching up on the routine, habit and a pivotal degree and earning the power are some of the challenges of the Iranian educational system as a result of a gap between schools and society. The nature of governing rules in educational institutions and societies require that effective relationships between school and community be established, and the environmental and social requirements be considered. Moreover, learning to see things from new angles in order to get rid of the sense of daily routine and overcoming the sense of the urge to essentialism to see the applications and rules of games should be considered as an important matter by authorities in various educational systems. Ultimately, the overcoming of presuppositions and urge to essentialism in order to verify and assess the real affairs will be possible for people when they feel themselves as an exile.