To provide a content distribution system with advertisement capable of surely reproducing the advertisement in a user terminal.

This content distribution system with advertisement is composed of: a user terminal and a content distribution server with advertisement; and an advertisement server. In the system, the user terminal transmits content ID, and the content distribution server with advertisement receives the content ID, and transfers it to the advertisement instruction server, and the advertisement instruction server acquires advertisement insertion schedule information based on the content ID, and transmits it to the content distribution server with advertisement, and the content distribution server with advertisement transmits the content with advertisement to the user terminal based on the received advertisement insertion schedule.