Abstract: A system and method of providing ancillary on-line content for a literary work provides up-to-date and multi-media content, increasing the value to a user of a copy of the literary work, such as a printed textbook. In return, an author or publisher of the literary work has additional opportunities for revenues after the initial sale of copies of the literary work. The on-line ancillary content is restricted to users who have a password subject to an access limit such as an expiration date. The system characterizes the literary work and locates on-line updates based on the characterization. In addition, The ancillary distribution content system and method facilitates communication between users of the literary work, evaluators considering use of the literary work, publishers, and interactive classroom environments that utilize the literary work.