As an uncelebrated prose writer, Huang Tingjian’s prose writing techniques fell into oblivion. However, his theory of prose writing had far reaching impact on the establishment of writing studies in the Southern Song dynasty. Huang Tingjian systematically discussed prose writing methods based on the classic works of the ancients, and applied these methods to the teaching of his apprentices. His instructions on prose writing involved two dimensions: the primary techniques for beginners and the ultimate objective of being unique. In addition, Huang Tingjian taught scholars to study ancient prose to acquire writing techniques useful for the imperial examination, which anticipated the practice of using ancient proses for pedagogy. He introduced the general rules of writing, but also made great attempts to free himself from his predecessors’ conventions, which later gave rise to Lü Benzhong’s theory of huofa (unfixed method). Huang Tingjian’s compositional purport, mediated by Lü’s theory, developed into resources that could resist the conventionalization of the prose writing methods in the Southern Song Dynasty.