A system, method, and computer-readable medium are disclosed for performing automated, cloud-based migrations of entitled digital assets. A set of entitlement data corresponding to a set of digital assets installed on a first system is processed with a set of digital asset source data to generate an equivalent set of digital assets. A first identifier associated with the source system is then cross-referenced to a second identifier associated with a target system. The second identifier and the set of entitlement data are processed to generate a second set of digital asset entitlements entitling the target system to use the set of equivalent digital assets. A migration request and the second identifier are then processed to provide the set of equivalent digital assets to the target system.