Systems and methods for upgrading from one or more digital media assets to a set of digital media assets over a network are described. A potential purchaser can be notified of available upgrade opportunities that are available for purchase. The potential purchaser can elect to pursue an upgrade opportunity so as to purchase a set of digital media assets. Upon upgrading to the set of digital media assets, the digital media assets within the set of digital media assets are made available to the purchaser. Typically, on upgrading from one or more of the digital media assets in the set of digital media assets to the entire set of digital media assets, the purchaser pays a lower cost than would be otherwise charged if the purchaser were to purchase the set of digital media assets in a non-upgrade manner. The cost associated with an upgrade opportunity can be based on prior purchases of digital media assets in the set of digital media assets. The cost associated with an upgrade opportunity can also be dynamically adjusted if other digital media assets in the set of digital media assets are subsequently purchased.