A monitoring system for a working machine includes a boarding detector to detect boarding and alighting of an operator, the boarding detector being provided in the working machine, a position detector to detect a position based on a signal sent from a positioning satellite when the boarding detector detects the alighting of the operator, a transmitter to transmit, to a management machine, positional information representing the position detected by the position detector, and a controller to move the management machine based on the positional information when the boarding detector detects the alighting, the controller being provided in the management machine.