Abstract: A system and method for contextually understanding and analyzing system use and misuse are described. In one preferred embodiment, one or more trigger events are detected and information related to the events is received. One or more exception rules are retrieved from exception rules tables within a database and the exception rules are applied to the received information. If a valid exception is identified, an exception notification is created and stored in oversight record tables within the database for further processing. Appropriate recipient users to receive the exception notification are identified from the actions, transactions, and contextual information tables within the database and the exception notification is further transmitted to the identified recipient users.