This research explores the learning of Islamic Arabic literary works ("Al-Adab Al-'Arabi") typical of "Pesantren" (Islamic boarding schools) and the role of Kyai in the cultural transformation of the teachings of piety in Arabic literature. This study used a phenomenological design and applied qualitative approach for the data analysis. The qualitative studies are focused on three research themes, namely (a) learning Arabic literature; (b) cultural transformation in "pesantren," and (c) teaching "pesantren," a qualitative approach that aims to understand cultural transformation in "Pesantren," interpret the Arabic literature learning typical of the "pesantren," interpret the behavior of "Kyai" and "santri," and connect meanings based on empirical reality. This research was conducted by involving 20 Santris and 7 Kyaisat the Pesantren of Darussalam Ciamis and Pesantren Miftahul Huda II Bayasari as participants. Data collection was carried out by in-depth interviews, observation, and documentation. The data accuracy was checked by digging and collecting data from phenomena and contexts from the cultural transformation of the teachings of truth in a typical Islamic boarding school experienced by the students in accordance with their belief level. Researchers describe data in patterned language about what the individual has seen and felt. Furthermore, the fundamental integration of the collected data's descriptions into one statement is the essence of the Arabic literary learning experience in the scope of cultural transformation. The results showed that the students had the experience of learning Arabic literature typical of "pesantren," which influenced their behavior. "Kyai" and center made Arabic literature as a way of life. Interestingly, these characteristics make Arabic literary works typical of "pesantren" capable of fostering a sense of language and literary sensitivity ("Al-Tadzawwuq Al-Adabi"), building character education for "santri" (students), encouraging the growth of "tasamuh" (tolerance) and culture. This finding would likely serve as a reference to increase the development of traditional "pesantren." The government should support any efforts attempted to preserve Islamic culture by examining "Pesantren"-specific Arabic literature for the archipelago's Islamic community.