A management device of a license management system acquires a usage request of a content from an SD card or a printer via a relay device, analyzes the acquired usage request, acquires usage environment information of the SD card or the printer from the relay device, analyzes the acquired usage environment information, generates license information including a usage rule corresponding to the analysis results of the usage request and the usage environment information, generates instruction information indicating how to handle the license information in the relay device based on the analysis result of the usage environment information, embeds the generated instruction information in the license information, and sends the license information to the relay device. The relay device receives the license information in which the instruction information is embedded, and transfers the received license information to the SD card or the printer according to the instruction information which is embedded in the license information with performing certain processing or without performing any processing to the license information.