Systems and methods provide at least one software application to users from a software monitor computer server. The software application requires a license grant for use. The software monitor computer server tracks usage of the software application to develop historical use patterns. The software monitor computer server also receives calendar input from electronic calendars of the users and analyzing the calendar input to identify future calendared uses of the software application. This allows the software monitor computer server to predict the future license grant needs of the software application based on the historical use patterns and the future calendared uses of the software application. The software monitor computer server also provides substitute software applications to the users when an insufficient number of license grants are available to meet the future calendared uses of the software application.