A content transport security system includes a computing platform having processing hardware and a memory storing software code and a database including one or more business rule(s). The processing hardware executes the software code to intercept a content file including a content asset, during a file transfer of the content file between a client device and a destination device, determine an authorization status of the destination device, and decrypt the content file, using a decryption key corresponding to an encryption key available to the client device. The processing hardware further executes the software code to search the content asset for a forensic identifier, assign a classification to the file transfer, based on the authorization status and a result of the searching, the classification being one of allowable, forbidden, or suspicious, and allow or block the file transfer to the destination device, based on the classification and the business rule(s).