A system, method, and computer-readable medium are disclosed for automatically migrating entitled digital assets from a source system to the target system. A first personalization agent is installed on a target system. A first set of digital assets entitlement data is provided along with an associated first set of digital assets data, which is then installed on the target system by the first personalization agent. A second set of digital assets entitlement data associated with a second set of digital assets data installed on a source system is determined by a second personalization agent. The second set of digital assets entitlement data is disassociated from the second set of system identifier data and then associated with the first set of system identifier data. The second set of digital assets is then installed the target system by the first personalization agent.