Abstract: A delivery box stores a delivery item and can be moved to a delivery destination. A management server manages delivery of the delivery item using the delivery box. The delivery box includes a power supply, a temperature adjustment unit adjusting temperature of the delivery item with a power supplied from the power supply, and a transmission/reception unit transmitting/receiving information to/from the management server via a communication network. The management server includes a delivery possibility determination unit executing delivery possibility determination of determining whether temperature of the delivery item can be maintained at a predetermined temperature by the temperature adjustment unit until the delivery item is delivered to the delivery destination. The delivery possibility determination unit executes the delivery possibility determination based on at least the power supply information relating to power supplied from the power supply acquired from the delivery box.