This study aims to describe and analyze the relationship between the principles of language politeness and the cooperative principle in the digital communication of students in the WhatsApp group of Al Hasan Islamic Boarding School. The background of this study is based on the importance of using polite, clear, relevant, and context-appropriate language in digital communication to create effective interaction while maintaining social harmony. Based on this background, the study focuses on presenting data systematically and clearly in accordance with the research focus, namely the relationship between the principles of language politeness and the cooperative principle in the WhatsApp chats of the male students’ group at Al Hasan Islamic Boarding School. This study employs a descriptive qualitative approach within a pragmatic framework, referring to Geoffrey Leech’s politeness theory and H. P. Grice’s cooperative principle. The data consist of utterances in WhatsApp group conversations collected over three months, from December 2025 to February 2026. The data were purposively selected based on utterances containing the application of the principles of language politeness and the cooperative principle, as well as having clear and relevant conversational contexts. From the conversations obtained, five conversation scripts containing 11 utterance data were selected for analysis. Data were collected through digital observation and documentation in the form of screenshots of conversations, then transcribed and classified using coding techniques based on Leech’s six politeness maxims and Grice’s four cooperative principle maxims. Data analysis was conducted through data reduction, data presentation, and conclusion drawing based on the Miles, Huberman, and Saldaña model, while data validity was examined through triangulation. The results show that the maxim of tact and the maxim of relevance are the most dominant. Their relationship is considered qualitatively strong because the 11 data demonstrate a consistent connection between the fulfillment of politeness and the cooperative principle in the utterances. These findings confirm that students’ digital communication prioritizes clarity, contextual appropriateness, and social harmony.