Abstract: There is disclosed a system and method for real time server side per stream insertion of strategic media and per-stream delivery. In one aspect of the invention the system comprises a media server for modifying a plurality of live media sub-streams based upon the categorizations of a group of connected media clients. In a further aspect of the invention, the live source media sub-streams are modified by overlaying delimited media content segments within the plurality of sub-streams with media assets, inserting media assets into the plurality of sub-streams, removing one or more of the media content segments from the sub-streams, and adjusting encoded markers within the plurality of sub-streams to compensate for the modifications.