A program transfer system includes: a communication unit communicating with a robot and outputting a result of the communication; a determination unit checking a work program provided in the robot, based on the result of the communication, and determining whether to import a different target work program from the work program or not; a program import unit importing the target work program to the robot when the determination unit determines the importing; a collection unit collecting work data of complete work from the robot; and a program update unit performing machine learning using the work data collected by the collection unit, and updating the target work program, based on a result of the machine learning.