This study investigates the intricate dynamics of student–faculty interactions in asynchronous online communication, focusing in particular on professors’ responses to non-native English-speaking students’ (NNSs’) favor-asking during online exchanges. Through qualitative analysis of email exchanges, this research examines how students articulate their concerns and requests for grade reassessment, and how professors respond to such instances of favor-asking. This study indicates that politeness is a more critical issue in asynchronous email communication than whe face-to-face interactions. The findings reveal that students often challenge professors’ authority by questioning assessment fairness, whereas professors employ disaffiliative strategies to maintain academic rigor and uphold their authority. This study highlights the role of cultural norms and politeness strategies in shaping these interactions, suggesting that a lack of awareness regarding these norms can lead to misunderstanding and escalate tensions. Furthermore, this research underscores the necessity of teaching pragmatic communication skills to non-native speakers to enhance their engagement and effectiveness in academic discourse. This study illuminates the complexities of these exchanges, this study contributes to a deeper understanding of the challenges faced by both students and faculty in the context of assessment and communication in higher education.