A system and method for automatically detecting issues during screensharing in an online meeting. The system and method allow automatic status notification of screensharing, which facilitates efficient and convenient use of virtual meetings. The system and method also use a live status indicator to provide constant and continuous data about the health of the ongoing screensharing session, which prevents computer and network resources waste on status inquiries. The system and method also recognize a problem/issue of the content-sharing and provide virtual meeting participants real-time action guidance to optimize the quality of content-sharing.