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What kind of impact did social networks of Song literati have on their lives in exile? This paper focuses on Sun Di 孫覿 (1081–1169), a prominent literary figure in the Northern to Southern Song transition, and studies his epistolary writings in connection with his banishment to Xiangzhou 象州 in the years 1133 and 1134. Through an in-depth analysis of the contents of his letters, the paper shows how Sun Di established ties with officials in different localities and how he responded to the humiliation of banishment. I argue that Sun Di’s reputation as a literary stylist among his contemporaries helped him to develop a good rapport with local officials, particularly in the Guangnan West circuit, which was essential to creating a relatively comfortable exile journey and a pleasant life during his confinement. This study highlights the value of letters as historical sources pertaining to Song political and literati culture and sheds light on literati responses to life’s many challenges.