Carboxymethyl chitosan (CMCS) is a useful polysaccharide with potential applications in food, cosmetic and biomedical industries. Nonetheless, CMCS is unfavorable for maintaining intestinal flora balance. In this study, gallic acid (GA) was grafted with CMCS through ascorbic acid/hydrogen peroxide initiated graft copolymerization reaction, producing GA grafted CMCS (GA-g-CMCS). The digestive and fermentative behavior of CMCS and GA-g-CMCS were investigated by using in vitro simulated gastrointestinal digestion and colonic fermentation models. Results showed that the average molecular weight (Mw) of CMCS gradually decreased during salivagastro-intestinal digestion, changing from original sheet-like morphology to porous and rod-like fragments. However, the Mw and morphology of GA-g-CMCS were almost unchanged under saliva-gastro-intestinal digestion. Meanwhile, the grafted GA moiety was not released from GA-g-CMCS during saliva-gastro-intestinal digestion. As compared with CMCS fermentation, GA-g-CMCS fermentation significantly suppressed the relative abundance of Escherichia-Shigella, Paeniclostridium, Parabacteroides, Lachnoclostridium, Clostridium_sensu_stricto_1, UBA1819 and Butyricimonas, while facilitated the relative abundance of Enterobacter, Enterococcus, Fusobacterium and Lachnospira. In addition, GA-g-CMCS fermentation significantly enhanced the production of short-chain fatty acids. These findings suggested that the digestive stability and prebiotic effect of CMCS were improved by grafting with GA.