The presently disclosed subject matter aims to a system and method directed to provide a remote session user experience analysis. The system and method includes Remote Desktop Protocol (RDP) server comprising a processing circuitry configured to: obtain connection information from a Remote Desktop Protocol (RDP) client, remote from the Remote Desktop Protocol (RDP) server, associated with a connection between the Remote Desktop Protocol (RDP) client and a networking device directly communicating with the Remote Desktop Protocol (RDP) client; and, generate, based on the connection information, a user experience score indicative of the quality of the connection during the remote session.