An example method of entitling endpoint software in a multi-cloud environment having a public cloud in communication through a messaging fabric with a data center includes: determining, by an entitlement service executing as a cloud service in the public cloud, deployment information for the endpoint software executing on virtualized hosts of the data center; generating, by the entitlement service in response to an entitlement request, an entitlement task in response to verifying the entitlement request against the deployment information; sending, through the messaging fabric, the entitlement task from the entitlement service to an entitlement agent of an agent platform appliance executing in the data center; and applying, by the entitlement agent in cooperation with a licensing service of the endpoint software, a subscription entitlement as indicated in the entitlement task.