A system and method of generating index information for electronic documents. The system includes a client, one or more information retrieval (IR) engines, such as a search engine, which are each in communication with each other via a network. In one embodiment of the invention, the server maintains a plurality or data objects that are protected by digital rights management (DRM) software. Upon receiving a network request from one of the IR systems, the server dynamically generates an electronic document that provides index information that is associated with one of the data objects. In one embodiment of the invention, the server dynamically generates the contents of the electronic document based upon the indexing characteristics of the IR system. Furthermore, upon receiving a network request from one of the client, the server determines whether the client is authorized to access the data object that is associated with the network request. If the client is authorized to access the data object, the server transmits the data object to the user. Alternatively, if the client is not authorized to access the data object, the server dynamically prepares instructions to the client, the instructions describing additional steps the user at the client may perform to get authorized to access the data object.