A strategy is described for assessing and mitigating vulnerabilities within a data processing environment. The strategy collects access data that reflects actual log-in behavior exhibited by users in the environment. The strategy also collects rights data that reflects the rights possessed by one or more administrators within the environment. Based on the access data and rights data, the strategy identifies how a user or other entity that gains access to one part of the environment can potentially compromise additional parts of the environment. The strategy can recommend and implement steps aimed at reducing any identified vulnerabilities.