A system is provided for generating real-time regulatory compliance alerts using taxonomy based classifications of regulatory obligations. The system may comprise a database storing taxonomy based classifications of regulatory obligation data comprising a plurality of categories, modules, subjects, and rules within the regulatory obligation data. The system may also comprise a plurality of processors that monitor user activity associated with the system and monitoring circuitry that receives data corresponding to the monitored user activity and identifies at least one of the plurality of categories, modules, subjects, and rules as related to the received data. The system may further comprise alert circuitry that issues a compliance alert corresponding to the identified at least one of the plurality of categories, modules, subjects, and rules within the regulatory obligation data.