Khāqānī, a prominent poet of the sixth century, besides his Divan and the masnavi Tohfat al-ʿIrāqayn, has a less-studied work entitled Monshaat, which is significant for understanding his thought, language, and worldview. Many scholars believe that a precise understanding of Khāqānī’s odes is not possible without recognizing the linguistic and intellectual layers of his Monshaat. The present study, using a descriptive–analytical method and a critical stylistic approach, examines three types of letters in religious, political, and popular contexts within the Monshaat and analyzes them on four levels—lexical, syntactic, pragmatic, and rhetorical—in order to uncover the dominant discourses of Khāqānī’s era and his mode of engagement with them. The findings indicate that Khāqānī lived in a context where knowledge and virtue did not hold a stable position within the power structure, and flattery had become a tool for attaining governmental positions. Among religious, political, philosophical, theological, and mystical discourses, his intellectual orientation is most closely aligned with the philosophical discourse, though it was not compatible with the preferences of the rulers of his time, and he consequently did not gain an appropriate social and political status. The study further shows that the concept of fate in Khāqānī’s Monshaat represents a compelled intellectual and emotional response to his social and political failures.