Systems and methods for automatic self-configuration of deployments of sets of enterprise software applications to users are disclosed. Exemplary implementations may: store information, including executable code for a set of enterprise software applications and a configuration database including deployment-specific configuration settings and corresponding setting values; monitor and quantify operations of a deployment of the set of enterprise software applications; assess whether a system-initiated modification of the deployment is likely to improve a particular monitored and quantified operation; automatically generate a system-initiated modification database based on the system-initiated modification; and modify the deployment in accordance with the system-initiated modification database.