In accordance with the present approach, a license analysis system may receive user activity data for a software program from an enterprise or client, including a client-specific association between license types and user assignments. The user assignments may include roles, profiles, and/or authorization objects assigned to each user within the software program. The license analysis system may analyze the user activity data to generate one or more 1:m relationships of each license type to a number of user assignments within the enterprise. The license analysis system may then compare the 1:m relationships to the user activity data to identify an acceptable license type assignment for each user that provides appropriate software authorizations according to their historic software usage. By providing the acceptable license type assignments to the enterprise, the license analysis system enables the enterprise to improve or optimize its license distribution by closely matching users with appropriate license types.