Systems and methods for packaging, delivery, and use of digital content. In one embodiment, a license matrix is created and used for evaluating the license rights applicable to a requested use of a content item. The license matrix can comprise a plurality of licenses grouped in license chains, and each license can include a set of entitlement rules and a set of grants. A license chain can be associated with an identifier corresponding to a use of content. In another embodiment, it is provided a method of packaging unsecured content for secured delivery over a computer network. In yet another embodiment, a system and method are provided for applying digital management rules to a content item at the time a user requests a use of the content item. In some embodiments, systems and methods allow evaluation of a requested use against a group of licenses to determine the applicable license rights for the requested use.