A system and method for content aware monitoring of an output of a media channel by a media system is provided herein. In at least one embodiment, the method comprises: receiving a media assertion schedule comprising a schedule of assertion checks which allow validating that the output of the media channel, by the media system, is synchronized with an expected media channel output; receiving, from a signature generating module, at least one observed signature file; determining that the timestamp data, in each of the at least one received observed signature file, aligns with at least one timecode included in an assertion check in the media assertion schedule; identifying an assertion condition included in the assertion check; and validating the assertion condition using the observed media frame signatures included in each of the at least one received observed signature file.