An image processing system includes a data acquisition unit and a position specifying unit. The data acquisition unit acquires a captured image showing a drop target of a work machine in which a transport object is dropped. The position specifying unit specifies a position of a predetermined part of the drop target shown in the captured image based on the captured image and a position specifying model. The position specifying model is a trained model, which outputs a position of a predetermined part of a drop target shown in an image when the image is input. A display device may display information regarding the position of the predetermined part of the drop target of the transport object specified by the image processing system.