Abstract: A digital asset tracking system comprises one or more Client Machine (CM) being installed with an Agent; wherein the Agent determines digital asset to be armed and selects arming method to arm the to-be-armed digital asset; an Asset Management Platform (AMP) managed by a System Administrator; wherein the AMP allows the System Administrator to make informed decisions on which assets are to be armed for monitoring; and a Callback Server being installed in a server, hosted either by cloud service provider or in an enterprise network on an internet facing interface; wherein the Callback Server listens-in and logs all communications received from armed assets; and when an armed asset is being opened and viewed, the arming on the armed asset triggers a communication back to the Callback Server that logs all communications received. A digital asset tracking method is also provided.