Given the place of Chan Buddhism within Song Dynasty literati culture, a Chan master during the Song Dynasty found excellence in literary expression a major asset. Dahui Zonggao (1089~1163) was arguably the Song Dynasty's most important Chan monk. A valuable part of his education as a future Chan master took place when he visited several times the already famous Chan poet and literatus Juefan Huihong (1071~1128); Juefan assisted him on at least two literary projects. Juefan Huihong (also known as Dehong) was a member of a circle of monks and laymen belonging to the Huanglong school of Chan centering on Baofeng Monastery at Mt. Shimen in the northern part of Jiangxi province to which Dahui also belonged for a number of years. Dahui's writings include a number of comments about Juefan Huihong's enlightenment, his expulsion from the Zhenjing Kewen's (1025~1102) monastery immediately following his awakening, and understanding of Chan. These are helpful in understanding Huihong's complex relation to the Chan school, as well as in illuminating Dahui's view of Chan enlightenment and training.