Purpose: This study is an attempt to examine the role of pesantren (Islamic boarding schools) on social status of "santri" in Indonesia. The study aimed to find out what social class the "santri" in pesantren are viewed by the society; to what extent they enjoy being a part of historical and cultural legacy and social setting; and how pesantren acted as a social agent to transform the social status of "Kiyai" and "santri." Research Methodology: This research used a quantitative approach to data analysis by using questionnaires. This study has used the Smart-PLS to analyze the relations among variables. A close observation of their lifestyle and contribution to society further shows how pesantren have contributed to improving the socioeconomic status of students who had attended the pesantren. Findings: The support system and facilities at pesantren help the "santri" to achieve a respectable position in the society. Pesantren act as social reformers, and such educational institutions that can serve as cornerstones for bringing a change in the society. Implications for Research and Practice: Such change is compatible to scientific and ICT enabled modern infrastructural and technology-based systems. The study recommends not to consider pesantren merely as a religious school, but as a modernized institution that gives competitive knowledge, scientific approach, positive attitude and a cultural value rooted in Islamic ideology.