An information processing apparatus 14 includes a reception unit 22 that receives information based on a captured image obtained by an imaging device, an extraction unit 28 that extract a plurality of image data of which a degree of similarity with a subject specified by the information received by the reception unit 22 is equal to or greater than a predetermined value from a first image data group obtained by the bracket imaging and/or a second image data group obtained by non-bracket imaging which are accumulated in advance, a generation unit 30 that generates the imaging condition of the bracket imaging by using the plurality of image data extracted by the extraction unit 28, and a transmission unit 32 that transmits the imaging condition of the bracket imaging generated by the generation unit 30 to the imaging device.