A terminal insertion quality monitoring system includes an acceleration sensor disposed on a gripper of a terminal insertion equipment and configured to detect a dynamic acceleration of the gripper while using the gripper to insert a terminal into a housing, a control parameter acquisition device configured to acquire a plurality of control parameters of the terminal insertion equipment while inserting the terminal into the housing, and an artificial intelligence system adapted to classify the detected dynamic acceleration and the acquired control parameters into a plurality of different insertion modes by analyzing and calculating the detected dynamic acceleration and the acquired control parameters. The different insertion modes have a plurality of different grades of terminal insertion quality. The artificial intelligence system is configured to monitor a terminal insertion quality of the terminal according to the insertion mode to which the detected dynamic acceleration and the acquired control parameters correspond.