There is provided an information processing apparatus including a communication unit which communicates with a distribution server that contains content data for streaming delivery, a buffer unit which temporarily stores stream data obtained from the distribution server, a storage unit which stores an inserting content, a reproduction unit which reproduces the content inserted by the storage unit, and a control unit which measures a bandwidth of the network, determines whether it is possible to reproduce until the end of a next chapter defined by a chapter point set in the content based on a buffer volume of the buffer unit and the bandwidth, and when determined it is impossible, switches the content to be produced by the reproduction unit to the inserting content.