A surroundings monitoring system includes: a detection device that is disposed in a work vehicle and configured to be able to detect an object around the work vehicle; an acquisition unit that acquires a command signal indicating an operation checking mode for inspecting the detection device; a determining unit that determines a quality of an operating state of the detection device based on a detection result of the detection device after the command signal is acquired; and a display device that displays identification information of the detection device of which the operating state is determined to be not good by the determining unit.