Conversational language instructors as defined by the Korean Immigration Service’s E-2 visa category have become a hallmark of foreign language instruction in South Korea, particularly for English. Intended to supplement deficiencies in the language skills and curriculum of local Korean instructors, these instructors are a key source of exposure to the English-speaking cultures of countries such as the United States and Canada. Over the twenty-four year history of the formal categorization of conversation teachers, employment numbers have ranged into the tens of thousands, but have also fluctuated significantly. While factors like the global economic climate and changes of the ruling party in Seoul have impacted demand for teachers, relatively little formal scholarship has evaluated the process of education policy making in this area. This paper identifies the split between public and private education, socio-economic divisions, urban/rural dichotomies, devolution of political authority, and Korea’s modernization experience as key factors in the development of conversational education policy. This is combined with analysis of Korean Immigration Service annual reports on registered foreigners to indicate overall trends in visa issuance to evaluate trends over the course of the program and to discuss the relationship between foreign language education and policy in recent years. As the newly inaugurated Moon Jae-in administration begins to implement its new policy priorities in education, these key factors will continue to influence the success or failure of new policies and will illustrate the continued importance of language education policy in South Korean society.