A data leak protection system and methods thereof are described that identify and analyze a digital fingerprint for a data package, the digital fingerprint characterizing the data package based on a corpus of data within the data package. In one embodiment, an asset descriptor is configured to identify one or more assets within the corpus of data while a contextual analyzer frames the one or more assets into the prevailing contextual environment. Then, a domain identifier further identifies a data perimeter based on the assets identified for the prevailing contextual environment. A comparison of the digital fingerprint to a collection of domain specific identifiers allows further actions responsive to a digital fingerprint falling outside of the data perimeter for an identified contextual environment. In one example, a data leak triggers quarantining of the data package for further manual processing.