A work assisting server 10 includes a first assisting process element 121 and a second assisting process element 122 and communicates with a plurality of facility cameras 30 when an operator OP remotely operates a work machine 40 while viewing a captured image displayed on an image output device 221. The first assisting process element 121 extracts, as candidates, the facility cameras 30 including the work machine 40 in imaging ranges. The second assisting process element 122 selects the facility camera 30 that is able to obtain the imaging range including an optimal direction or size on the basis of movement of the work machine 40 and causes the selected facility camera 30 to output a captured image to the image output device 221.