A system and method for determining performance of connections between an endpoint device and a Cloud region is disclosed. A Cloud based host server communicates with the endpoint device operated by a user through a network. A data collection module is coupled to the Cloud server and the endpoint device. The data collection module periodically collects connection data associated with the endpoint device and collects context data of the endpoint device. An analysis engine compares a connection data metric derived from the connection data to a baseline value of the connection data metric associated with the context data of the endpoint device and determines substandard performance. The analysis engine provides an alert when a substandard performance is determined.