This chapter employs the MCELE framework’s Historical-Sociocultural dimension as a primary lens to trace the evolution of Iran’s educational system across three transformative eras: the Qajar dynasty, the Pahlavi regime, and the post-Islamic Revolution period. It analyzes the pendulum swing from early selective Western imitation to state-enforced secular modernization, and finally to the current focus on Islamization. The analysis reveals how shifting political ideologies—from nationalism to religious fundamentalism—have continuously reshaped English Language Teaching (ELT) policies. By prioritizing historical context, the chapter illuminates the deep-seated roots of current pedagogical challenges, showing how centuries of “imitative” reform and authoritarian control continue to constrain contemporary efforts toward effective language education.