A licensing manager server enables distribution of multiple software licenses from multiple separately located and/or different types of licensing server sources. Based on communications with the licensing manager server, a customer can control how a group of purchased software licenses can be distributed to members in a corresponding organization (e.g., company). For example, upon receiving a query about the order from a customer, a web portal of a vendor managed server provides a notification to the customer that the multiple software licenses can be selectively apportioned for distribution by multiple different licensing server sources. In response to the notification, the licensing manager server receives customer input indicating to allocate one portion of the multiple software licenses for distribution by a first licensing server source and to allocate another portion of the multiple software licenses for distribution by a second licensing server source.