A system and method of sharing digital literary works while protecting against an illegal reproduction through a communication network is disclosed. The system comprises a data communication network, a list providing server, at least one agent server, at least one user terminal, a main server, at least one sub-server, a premise communication network, and a network interface unit. The system is advantageous in that it enables users to share digital literary works produced for publicity, works having a low quality, or encrypted digital literary works through the network against a distribution of illegally reproduced digital literary works having the same quality as original literary works through a Sharing Web, thus preventing a reduction of sales amounts of original literary works due to such illegal reproductions.