A server and a method of operating the same are provided. The method includes receiving metadata corresponding to printing data from a printing data storage device that stores the printing data, receiving, from an image forming apparatus, a request to transmit printing job information, determining a transmission route of the printing data based on whether the printing data storage device and the image forming apparatus are capable of communicating with each other, generating printing job information including the metadata and the transmission route, and transmitting the printing job information to the image forming apparatus.